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Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

$670,000

Spacious Claiborne Fields Home with Beautiful Views & Convenient Centreville Location! Welcome home to this spacious and beautifully situated 4-bedroom, 3-bath home in the established and highly sought-after community of Claiborne Fields. With a 2-car garage and plenty of room both inside and out, this home offers the space and setting you've been looking for. The property sits on a beautiful lot with expansive views of open fields, mature trees, and a peaceful pond. The outdoor spaces are truly a highlight, with a wonderful sunroom and patio with a permanent umbrella—perfect for morning coffee, afternoon relaxation, or gathering with family and friends while enjoying the scenery. Inside, the generous floor plan offers comfortable living spaces, original hardwood floors, and plenty of room for everyday living and entertaining. The home has been thoughtfully maintained and features numerous updates and improvements, including a newer roof, newer heat pumps and furnace, Anderson 400 Series windows, granite countertops, Rinnai tankless hot water, water treatment system, and an encapsulated crawl space. Enjoy the best of both worlds—a peaceful neighborhood setting with beautiful open views, while being just minutes from downtown Centreville. Shopping, restaurants, parks, schools, and local amenities are all conveniently close by. A wonderful opportunity to enjoy space, privacy, beautiful surroundings. Come see why this one is special!

Spacious Claiborne Fields Home with Beautiful Views & Convenient Centreville Location! Welcome home to this spacious and beautifully situated 4-bedroom, 3-bath home in the established and highly sought-after community of Claiborne Fields. With a 2-car garage and plenty of room both inside and out, this home offers the space and setting you've been looking for. The property sits on a beautiful lot with expansive views of open fields, mature trees, and a peaceful pond. The outdoor spaces are truly a highlight, with a wonderful sunroom and patio with a permanent umbrella—perfect for morning coffee, afternoon relaxation, or gathering with family and friends while enjoying the scenery. Inside, the generous floor plan offers comfortable living spaces, original hardwood floors, and plenty of room for everyday living and entertaining. The home has been thoughtfully maintained and features numerous updates and improvements, including a newer roof, newer heat pumps and furnace, Anderson 400 Series windows, granite countertops, Rinnai tankless hot water, water treatment system, and an encapsulated crawl space. Enjoy the best of both worlds—a peaceful neighborhood setting with beautiful open views, while being just minutes from downtown Centreville. Shopping, restaurants, parks, schools, and local amenities are all conveniently close by. A wonderful opportunity to enjoy space, privacy, beautiful surroundings. Come see why this one is special!

306 Old Line Dr, Centreville

Listing courtesy of Taylor Properties. Contact:

$599,000

PROFESSIONAL INTERIOR PHOTOS COMING SOON! Exceptional value in the water-privileged Kent Island Estates community! This well-loved home has been thoughtfully improved and beautifully maintained by its current owners, offering approximately 2,300 sq. ft. of finished living space and an impressive list of indoor and outdoor improvements. Enjoy the best of Eastern Shore living with nearby waterfront dining, some of the area’s best local seafood, coffee shops, marinas and dockside destinations in Kent Narrows—all just minutes from home. With so much already completed, this home is truly move-in ready and an incredible opportunity to enjoy the Kent Island lifestyle. Inside, the former garage has been fully finished and transformed into an expansive bonus living space, perfect for a playroom, home office, gym, media room or additional family room. Outside is where this property really shines! Enjoy a large enclosed deck and screened porch overlooking the fully fenced backyard, an expansive brick patio, extensive landscaping and hardscaping, a paved driveway and an oversized shed offering exceptional storage with additional space currently used for workout equipment. Located in Kent Island Estates, enjoy community water access and the laid-back Eastern Shore lifestyle with nearby opportunities for boating, kayaking, fishing and crabbing. Convenient to the South Island Trail, Romancoke Pier, Kent Narrows, local dining and shopping, with easy access to the Bay Bridge. With approximately 2,300 sq. ft. of finished living space and so many improvements already completed, 212 Oregon Road is an exceptional opportunity to enjoy the best of Kent Island living!

PROFESSIONAL INTERIOR PHOTOS COMING SOON! Exceptional value in the water-privileged Kent Island Estates community! This well-loved home has been thoughtfully improved and beautifully maintained by its current owners, offering approximately 2,300 sq. ft. of finished living space and an impressive list of indoor and outdoor improvements. Enjoy the best of Eastern Shore living with nearby waterfront dining, some of the area’s best local seafood, coffee shops, marinas and dockside destinations in Kent Narrows—all just minutes from home. With so much already completed, this home is truly move-in ready and an incredible opportunity to enjoy the Kent Island lifestyle. Inside, the former garage has been fully finished and transformed into an expansive bonus living space, perfect for a playroom, home office, gym, media room or additional family room. Outside is where this property really shines! Enjoy a large enclosed deck and screened porch overlooking the fully fenced backyard, an expansive brick patio, extensive landscaping and hardscaping, a paved driveway and an oversized shed offering exceptional storage with additional space currently used for workout equipment. Located in Kent Island Estates, enjoy community water access and the laid-back Eastern Shore lifestyle with nearby opportunities for boating, kayaking, fishing and crabbing. Convenient to the South Island Trail, Romancoke Pier, Kent Narrows, local dining and shopping, with easy access to the Bay Bridge. With approximately 2,300 sq. ft. of finished living space and so many improvements already completed, 212 Oregon Road is an exceptional opportunity to enjoy the best of Kent Island living!

212 Oregon Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$650,000

This is a lovely 3 bedroom, 2.5 bath, waterfront home with panoramic views of the Chester River. It was built in 2001. It features: 9' ceilings, 2"x6" exterior wall construction, crown molding in every room, family room with wood burning fireplace, dining room with vaulted ceiling and skylight, kitchen with quartz countertops and all ;major appliances,ensuite bedroom on first floor and a large screened porch overlooking the river. Upstairs are two bedrooms, one has a cathedral ceiling overlooking the river. The other has two walk-in closets. There is a large bathroom on the second floor. There is plenty of additional storage including an outdoor storage shed with electricity, There is a new well pump and pressure tank installed in '26 , the house has dual heating a/c systems- the downstairs was replaced in '24. The house was professionally landscaped in '22 with a new irrigation system and outdoor lights were installed by the drive and in the trees for night time safety. A new roof was installed in '24. There is a dock that offers approximately 3' to 3 1/2' of water at mean high tide for kayaking, waterboarding, canoeing. The property is close to Chestertown and convenient to Rt. 301 making it an easy drive to DE, Phila, and D.C. Lovely old shade trees and being close to nature at the river's edge add to this wonderful home.

This is a lovely 3 bedroom, 2.5 bath, waterfront home with panoramic views of the Chester River. It was built in 2001. It features: 9' ceilings, 2"x6" exterior wall construction, crown molding in every room, family room with wood burning fireplace, dining room with vaulted ceiling and skylight, kitchen with quartz countertops and all ;major appliances,ensuite bedroom on first floor and a large screened porch overlooking the river. Upstairs are two bedrooms, one has a cathedral ceiling overlooking the river. The other has two walk-in closets. There is a large bathroom on the second floor. There is plenty of additional storage including an outdoor storage shed with electricity, There is a new well pump and pressure tank installed in '26 , the house has dual heating a/c systems- the downstairs was replaced in '24. The house was professionally landscaped in '22 with a new irrigation system and outdoor lights were installed by the drive and in the trees for night time safety. A new roof was installed in '24. There is a dock that offers approximately 3' to 3 1/2' of water at mean high tide for kayaking, waterboarding, canoeing. The property is close to Chestertown and convenient to Rt. 301 making it an easy drive to DE, Phila, and D.C. Lovely old shade trees and being close to nature at the river's edge add to this wonderful home.

209 Shoals Rd, Crumpton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,450,000

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the outlets, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This home features more than 4,400 square feet on three finished levels, with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that's upscale and comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook and a redesigned island perfect for gathering. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a second primary. The second level features three additional bedrooms and a large bonus room perfect for a home office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water and glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River and Chesapeake for day trips or sunset cruises. Recent improvements include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

5 Beds ⋅ 5 Baths

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the outlets, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This home features more than 4,400 square feet on three finished levels, with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that's upscale and comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook and a redesigned island perfect for gathering. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a second primary. The second level features three additional bedrooms and a large bonus room perfect for a home office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water and glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River and Chesapeake for day trips or sunset cruises. Recent improvements include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321

$595,000

Rare opportunity to own in sought after Creek Point Estates with NO HOA. You will fall in love with this amazing colonial on 1.6 acres with gleaming hardwood floors, great room with build in bookcases, fireplace, HUGE primary bedroom with 2 WICs, deck, screened in porch, large garage and room to play and expand. Owners have updated many important things including a new roof last year, newer HVAC, appliance and so much more. There is a 1 year warranty to top it off. Only minutes from a public boat ramp/docks, parks, shopping, doctors, historic Centreville and more. Come get this one before its gone!

Rare opportunity to own in sought after Creek Point Estates with NO HOA. You will fall in love with this amazing colonial on 1.6 acres with gleaming hardwood floors, great room with build in bookcases, fireplace, HUGE primary bedroom with 2 WICs, deck, screened in porch, large garage and room to play and expand. Owners have updated many important things including a new roof last year, newer HVAC, appliance and so much more. There is a 1 year warranty to top it off. Only minutes from a public boat ramp/docks, parks, shopping, doctors, historic Centreville and more. Come get this one before its gone!

112 Creek Point Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

$574,900

Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails.

4 Beds ⋅ 4 Baths

Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails.

118 Amanda Frances Ln, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$920,000

Elizabeth A. Turpin House c.1872 -Purchased in 2016, (fully renovated 2019-2022) Turpin House is a beautiful, 1872 Victorian, listed on the National Register of Historic Homes, featuring an “Empire” design interior with soaring 12-foot ceilings, elegant chandeliers and handmade original plaster medallions. Recent renovations include original heartwood floors, plaster moldings, medalions and walls meticulously restored by expert craftsman. Modern upgrades include new electric, plumbing and high efficiency HVAC with, room by room, controllable mini-splits and programmable remotes making all of the spaces wonderfully comfortable, year round. Turpin House grounds include a rustic Victorian garden with fruit trees and raised vegetable beds, an outdoor kitchen for hosting garden parties, a woodworking shop and a "Carriage house" modernized with electric for off-street parking. The Turpin House features a main house with 6 bedrooms, 5 bathrooms, 5 fireplaces (3 marble), and a mother-in-law suite (2 bedrooms-2 bathrooms) that offers its own private exterior garden entrance. This home is 2 blocks from Centreville's 1782 town square, an historic town wharf, restaurants and community events including local wine & jazz festivals. One mile away is a brand new community center including indoor and outdoor pools, extensive workout gyms, an indoor track, saunas and community classes & events. Income Apartment: In addition, the Turpin property includes a garden-level one bedroom income suite with a private exterior entrance. Fully renovated and continuously leased since 2020, this space is legally permitted under R2 zoning and provides a substantial financial offset to mortgage expenses without compromising owner privacy. Ideal for commuters, Turpin is 15 minutes to the Bay Bridge and Chestertown and 38 to Annapolis, including daily commuter buses to Washington DC. Elizabeth A Turpin House is a dream home with the wonderful warm vibe of the large Victorian family who built it. This stunning home is truly a “move-in ready and an historic work of art”

8 Beds ⋅ 7 Baths

Elizabeth A. Turpin House c.1872 -Purchased in 2016, (fully renovated 2019-2022) Turpin House is a beautiful, 1872 Victorian, listed on the National Register of Historic Homes, featuring an “Empire” design interior with soaring 12-foot ceilings, elegant chandeliers and handmade original plaster medallions. Recent renovations include original heartwood floors, plaster moldings, medalions and walls meticulously restored by expert craftsman. Modern upgrades include new electric, plumbing and high efficiency HVAC with, room by room, controllable mini-splits and programmable remotes making all of the spaces wonderfully comfortable, year round. Turpin House grounds include a rustic Victorian garden with fruit trees and raised vegetable beds, an outdoor kitchen for hosting garden parties, a woodworking shop and a "Carriage house" modernized with electric for off-street parking. The Turpin House features a main house with 6 bedrooms, 5 bathrooms, 5 fireplaces (3 marble), and a mother-in-law suite (2 bedrooms-2 bathrooms) that offers its own private exterior garden entrance. This home is 2 blocks from Centreville's 1782 town square, an historic town wharf, restaurants and community events including local wine & jazz festivals. One mile away is a brand new community center including indoor and outdoor pools, extensive workout gyms, an indoor track, saunas and community classes & events. Income Apartment: In addition, the Turpin property includes a garden-level one bedroom income suite with a private exterior entrance. Fully renovated and continuously leased since 2020, this space is legally permitted under R2 zoning and provides a substantial financial offset to mortgage expenses without compromising owner privacy. Ideal for commuters, Turpin is 15 minutes to the Bay Bridge and Chestertown and 38 to Annapolis, including daily commuter buses to Washington DC. Elizabeth A Turpin House is a dream home with the wonderful warm vibe of the large Victorian family who built it. This stunning home is truly a “move-in ready and an historic work of art”

201 S Liberty St, Centreville

Listing courtesy of Cottage Street Realty LLC. Contact:

$439,000

Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water views and an impressive collection of community amenities. Neutral paint, wide-plank luxury vinyl plank flooring, new carpeting, and updates to the kitchen and bathrooms create a fresh, cohesive feel throughout. Step inside to a spacious living and dining room combination designed for easy everyday living and entertaining. The dining area flows into the updated kitchen, with a breakfast bar providing a natural transition between the spaces. Quartz countertops, stainless steel appliances, and a subway tile backsplash give the kitchen a polished look, while its open connection to the adjacent family room keeps the layout inviting and functional. A sliding glass door leads from the family room to the deck, where views of Lake Amletto create a peaceful backdrop for dining or unwinding outdoors. Upstairs, all three bedrooms feature vaulted ceilings that enhance the sense of space. The primary bedroom includes two closets and a stylish vanity area, along with a private water closet featuring a tiled tub and shower surround with a soaking tub. Two additional bedrooms share the hall bath, where a vaulted ceiling and statement light fixture lend an elevated feel. The lower level adds valuable flexibility with a recreation room and sliding glass door opening to the backyard. A separate laundry room is also located on this level, along with interior access to the attached one-car garage. Just inside the garage, a convenient drop zone helps keep everyday essentials organized, while the painted garage offers additional storage space. Beyond the home, Queen’s Landing delivers a true waterfront lifestyle along the Chester River on Kent Island. Residents enjoy a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. With Lake Amletto just outside and access to Kent Narrows, Eastern Bay, and the Chesapeake Bay nearby, this inviting home offers an ideal blend of updated comfort, water views, and resort-style living. Please note: photos depicting furniture have utilized virtual staging.

3 Beds ⋅ 4 Baths

Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water views and an impressive collection of community amenities. Neutral paint, wide-plank luxury vinyl plank flooring, new carpeting, and updates to the kitchen and bathrooms create a fresh, cohesive feel throughout. Step inside to a spacious living and dining room combination designed for easy everyday living and entertaining. The dining area flows into the updated kitchen, with a breakfast bar providing a natural transition between the spaces. Quartz countertops, stainless steel appliances, and a subway tile backsplash give the kitchen a polished look, while its open connection to the adjacent family room keeps the layout inviting and functional. A sliding glass door leads from the family room to the deck, where views of Lake Amletto create a peaceful backdrop for dining or unwinding outdoors. Upstairs, all three bedrooms feature vaulted ceilings that enhance the sense of space. The primary bedroom includes two closets and a stylish vanity area, along with a private water closet featuring a tiled tub and shower surround with a soaking tub. Two additional bedrooms share the hall bath, where a vaulted ceiling and statement light fixture lend an elevated feel. The lower level adds valuable flexibility with a recreation room and sliding glass door opening to the backyard. A separate laundry room is also located on this level, along with interior access to the attached one-car garage. Just inside the garage, a convenient drop zone helps keep everyday essentials organized, while the painted garage offers additional storage space. Beyond the home, Queen’s Landing delivers a true waterfront lifestyle along the Chester River on Kent Island. Residents enjoy a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. With Lake Amletto just outside and access to Kent Narrows, Eastern Bay, and the Chesapeake Bay nearby, this inviting home offers an ideal blend of updated comfort, water views, and resort-style living. Please note: photos depicting furniture have utilized virtual staging.

41 Queen Catherine Ct, Chester

Listing courtesy of Northrop Realty. Contact: 4104651770

$569,900

Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

233 Cross Creek Ct, Chester

Listing courtesy of Rory S. Coakley Realty, Inc.. Contact:

$345,000

Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

217 Edmore Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$459,000

Perfect location for an afternoon walk to the pool and clubhouse! New roof with a warranty that conveys with the purchase of this lovely home. The updated kitchen is one of the highlights with the light cherry cabinetry and Cambria Quartz counters, show off nicely against the mahogany flooring that extends thru out this home. Plantation shutters add character to the family room while the formal living and dining area reflect a more formal setting for entertaining. Owners suite in the rear of the home while a guest suite is in the front allows plenty of privacy for company or family. Enjoy relaxing outside on a large paver patio with a motorized retractable awning with new Sunbrella fabric. Overall, this is a lovely, well maintained home waiting for a new occupant to enjoy! Symphony Village is a community of 395 houses, with mature trees, lush landscaping, and a magnificent clubhouse where myriad activities are available, including frequent social gatherings, holiday picnics, card games, mahjong, dance classes, billiards, a vibrant artisan group with classes and shows, plus a quarterly reception for residents and friends to view the latest art creations. There are bocce courts, tennis and pickle ball courts, and a putting green with many keen players. The outdoor pool is open from May to September, and you can find several shady seating spots if you wish. The indoor heated pool is open year-round, and features a lift chair for those who need it. Water aerobics classes are offered weekdays indoors or outdoors depending on the season. Centreville is the Queen Anne County seat, with a historic courthouse, several restaurants, grocery stores, and other essential services. Easy drive to Easton, St. Michaels, Annapolis and Chestertown, and the beach is not too far away.

2 Beds ⋅ 2 Baths

Perfect location for an afternoon walk to the pool and clubhouse! New roof with a warranty that conveys with the purchase of this lovely home. The updated kitchen is one of the highlights with the light cherry cabinetry and Cambria Quartz counters, show off nicely against the mahogany flooring that extends thru out this home. Plantation shutters add character to the family room while the formal living and dining area reflect a more formal setting for entertaining. Owners suite in the rear of the home while a guest suite is in the front allows plenty of privacy for company or family. Enjoy relaxing outside on a large paver patio with a motorized retractable awning with new Sunbrella fabric. Overall, this is a lovely, well maintained home waiting for a new occupant to enjoy! Symphony Village is a community of 395 houses, with mature trees, lush landscaping, and a magnificent clubhouse where myriad activities are available, including frequent social gatherings, holiday picnics, card games, mahjong, dance classes, billiards, a vibrant artisan group with classes and shows, plus a quarterly reception for residents and friends to view the latest art creations. There are bocce courts, tennis and pickle ball courts, and a putting green with many keen players. The outdoor pool is open from May to September, and you can find several shady seating spots if you wish. The indoor heated pool is open year-round, and features a lift chair for those who need it. Water aerobics classes are offered weekdays indoors or outdoors depending on the season. Centreville is the Queen Anne County seat, with a historic courthouse, several restaurants, grocery stores, and other essential services. Easy drive to Easton, St. Michaels, Annapolis and Chestertown, and the beach is not too far away.

139 Harmony Way, Centreville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$899,000

Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

148 Elinor St, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

$1,025,000

Nestled in the serene enclave of Mallard Pond, this exquisite manor-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Spanning an impressive 3,300 square feet, this home is designed to cater to both relaxation and entertainment, featuring five spacious bedrooms and two full and two half elegantly appointed bathrooms. Step inside to discover a thoughtfully crafted interior that radiates warmth and sophistication. The open floor plan seamlessly connects the family room to the gourmet kitchen, where culinary dreams come to life. Outfitted with stainless steel appliances, including a built-in microwave and range, the kitchen boasts upgraded countertops and a charming breakfast area, ideal for casual dining. The formal dining room invites memorable gatherings, while the cozy family room off the kitchen provides a perfect retreat for everyday living. Natural light floods the home through skylights and large windows, while the newly finished 400 sq. ft. three season room adds to enhancing the inviting atmosphere. Luxurious touches abound, from the rich hardwood and ceramic tile flooring to the plush carpeting in the bedrooms. The master suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, creating a personal oasis for relaxation. The exterior of the property is equally impressive, set on a sprawling 0.96-acre lot that offers beautifully landscaped grounds and a tranquil pond view. Enjoy the outdoors with a personal saltwater pool, perfect for summer days, and a spacious rear yard that invites outdoor activities and gatherings. The property also includes a shed for additional storage and an oversized attached garage with ample space for vehicles and hobbies and offering an EV50 amp charger (28MPH). Experience the peace of mind that comes with owned solar energy, enhancing the home's efficiency while reducing environmental impact. The location is a hidden gem, situated on a no-thru street, ensuring privacy and tranquility while still being conveniently close to local amenities. This residence is more than just a home; it's a lifestyle choice that embodies luxury, comfort, and the beauty of nature. Embrace the opportunity to make this exceptional property your own and enjoy the exclusive lifestyle it offers. Must provide financial qualifications to view this property

5 Beds ⋅ 4 Baths

Nestled in the serene enclave of Mallard Pond, this exquisite manor-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Spanning an impressive 3,300 square feet, this home is designed to cater to both relaxation and entertainment, featuring five spacious bedrooms and two full and two half elegantly appointed bathrooms. Step inside to discover a thoughtfully crafted interior that radiates warmth and sophistication. The open floor plan seamlessly connects the family room to the gourmet kitchen, where culinary dreams come to life. Outfitted with stainless steel appliances, including a built-in microwave and range, the kitchen boasts upgraded countertops and a charming breakfast area, ideal for casual dining. The formal dining room invites memorable gatherings, while the cozy family room off the kitchen provides a perfect retreat for everyday living. Natural light floods the home through skylights and large windows, while the newly finished 400 sq. ft. three season room adds to enhancing the inviting atmosphere. Luxurious touches abound, from the rich hardwood and ceramic tile flooring to the plush carpeting in the bedrooms. The master suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, creating a personal oasis for relaxation. The exterior of the property is equally impressive, set on a sprawling 0.96-acre lot that offers beautifully landscaped grounds and a tranquil pond view. Enjoy the outdoors with a personal saltwater pool, perfect for summer days, and a spacious rear yard that invites outdoor activities and gatherings. The property also includes a shed for additional storage and an oversized attached garage with ample space for vehicles and hobbies and offering an EV50 amp charger (28MPH). Experience the peace of mind that comes with owned solar energy, enhancing the home's efficiency while reducing environmental impact. The location is a hidden gem, situated on a no-thru street, ensuring privacy and tranquility while still being conveniently close to local amenities. This residence is more than just a home; it's a lifestyle choice that embodies luxury, comfort, and the beauty of nature. Embrace the opportunity to make this exceptional property your own and enjoy the exclusive lifestyle it offers. Must provide financial qualifications to view this property

201 Mallard Dr, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,200,000

COMING SOON - Rare opportunity to own TWO homes, an impressive 4,800+ sq. ft. shop, additional pole barn, and 25+ acres—all just minutes from Route 301! The heated and insulated 120' x 40' shop is fully equipped for a mechanic, contractor, trucking operation, or other business use. It features two separate bays with an office, break room, and bathroom between them, plus additional loft storage. A 30' x 50' pole barn with electric and water offers even more possibilities and is ideal for horses, equipment, or agricultural use. Main Home – 2321 Millington Rd: Approximately 1,527 sq. ft. with 3 bedrooms and 2 baths. Features include hardwood floors, a spacious living area open to the dining room and kitchen, split-bedroom floor plan with private primary suite, laundry room, attached 2-car garage, front and rear covered porches, and hot tub. Neat as a pin and move-in ready! Guest House – 2327 Millington Rd: Approximately 1,142 sq. ft. with 3 bedrooms and 2 full baths, hardwood floors, open living and dining areas, rear covered porch, fenced area, and attached 1-car garage. Also in excellent condition! Whether you're looking for a small farm, trucking operation, contractor headquarters, mechanic's shop, multi-generational property, or simply room to spread out, this property offers an exceptional combination of residential, business, and agricultural possibilities. You couldn't source the land and recreate this collection of homes and buildings for less. A rare find and superb value for everything it has to offer—come see it! Updated exterior photos coming next week.

6 Beds ⋅ 5 Baths

COMING SOON - Rare opportunity to own TWO homes, an impressive 4,800+ sq. ft. shop, additional pole barn, and 25+ acres—all just minutes from Route 301! The heated and insulated 120' x 40' shop is fully equipped for a mechanic, contractor, trucking operation, or other business use. It features two separate bays with an office, break room, and bathroom between them, plus additional loft storage. A 30' x 50' pole barn with electric and water offers even more possibilities and is ideal for horses, equipment, or agricultural use. Main Home – 2321 Millington Rd: Approximately 1,527 sq. ft. with 3 bedrooms and 2 baths. Features include hardwood floors, a spacious living area open to the dining room and kitchen, split-bedroom floor plan with private primary suite, laundry room, attached 2-car garage, front and rear covered porches, and hot tub. Neat as a pin and move-in ready! Guest House – 2327 Millington Rd: Approximately 1,142 sq. ft. with 3 bedrooms and 2 full baths, hardwood floors, open living and dining areas, rear covered porch, fenced area, and attached 1-car garage. Also in excellent condition! Whether you're looking for a small farm, trucking operation, contractor headquarters, mechanic's shop, multi-generational property, or simply room to spread out, this property offers an exceptional combination of residential, business, and agricultural possibilities. You couldn't source the land and recreate this collection of homes and buildings for less. A rare find and superb value for everything it has to offer—come see it! Updated exterior photos coming next week.

2321 Millington, Millington

Listing courtesy of Village Real Estate Company LLC. Contact:

$849,000

NEW PRICE! Won't last long! From the moment you arrive, this exceptional home is sure to impress. Beautifully renovated and impeccably maintained, it feels fresh, modern, and anything but 28 years old. Located in the sought-after Prospect Bay community, this remarkable property offers water access, amenities galore, and the relaxed atmosphere of country-club living on Maryland’s Eastern Shore. A brick walkway and steps lead to the beautiful front porch and an impressive foyer with soaring ceilings, designer paint, and elegant board-and-batten detailing. The dramatic sightline extends through the great room to a wall of windows and two sets of glass French doors opening to the inviting screened porch. The modern eat-in chef’s kitchen is a showstopper, featuring quartz countertops, glass-front cabinetry, abundant storage, and a charming bay-window dining area. Wide-plank, wood-look, porcelain tile flooring flows throughout the main living areas, offering the beauty of wood with exceptional durability. Just off the kitchen, the spacious mudroom includes front-loading laundry machines, a utility sink, cabinetry, generous counter space, and convenient access to the two-car side-load garage. At the heart of the home, the breathtaking great room features soaring ceilings, board-and-batten walls, a wood-burning fireplace, and a dramatic wall of windows overlooking the lush backyard. Glass French doors lead to the expansive screened porch with wood flooring and high ceilings—an idyllic setting for morning coffee, relaxed dinners, and effortless entertaining. Beyond the porch, a spacious paver patio overlooks the peaceful, beautifully landscaped yard, enclosed by a newer white picket fence. The main level also offers an elegant formal dining room and three generously sized bedrooms, including the luxurious primary suite. The primary retreat features a walk-in closet and spa-inspired bath with dual vanities, porcelain tile flooring, a frameless glass walk-in shower with marble walls, and on-trend lighting and hardware. Gorgeous hardwood stairs lead to the upper-level overlook, where wide-plank engineered hardwood flooring continues throughout two additional bedrooms and a beautifully renovated full bath with a glass-enclosed walk-in shower and porcelain tile flooring. The flexible five-bedroom layout provides exceptional space for guests, home offices, hobbies, and/or multigenerational living. Outside, the private and beautifully landscaped lot is equally impressive. A charming backyard shed has been customized with an automatic garage-style door to accommodate a golf cart, while the expansive driveway provides parking for four or more vehicles in addition to the two-car garage. Peaceful, private, and polished from top to bottom, this extraordinary home offers gracious indoor-outdoor living in a community designed for recreation, relaxation, and life near the water. This is more than a home—it is the Eastern Shore lifestyle you have been waiting for.

5 Beds ⋅ 3 Baths

NEW PRICE! Won't last long! From the moment you arrive, this exceptional home is sure to impress. Beautifully renovated and impeccably maintained, it feels fresh, modern, and anything but 28 years old. Located in the sought-after Prospect Bay community, this remarkable property offers water access, amenities galore, and the relaxed atmosphere of country-club living on Maryland’s Eastern Shore. A brick walkway and steps lead to the beautiful front porch and an impressive foyer with soaring ceilings, designer paint, and elegant board-and-batten detailing. The dramatic sightline extends through the great room to a wall of windows and two sets of glass French doors opening to the inviting screened porch. The modern eat-in chef’s kitchen is a showstopper, featuring quartz countertops, glass-front cabinetry, abundant storage, and a charming bay-window dining area. Wide-plank, wood-look, porcelain tile flooring flows throughout the main living areas, offering the beauty of wood with exceptional durability. Just off the kitchen, the spacious mudroom includes front-loading laundry machines, a utility sink, cabinetry, generous counter space, and convenient access to the two-car side-load garage. At the heart of the home, the breathtaking great room features soaring ceilings, board-and-batten walls, a wood-burning fireplace, and a dramatic wall of windows overlooking the lush backyard. Glass French doors lead to the expansive screened porch with wood flooring and high ceilings—an idyllic setting for morning coffee, relaxed dinners, and effortless entertaining. Beyond the porch, a spacious paver patio overlooks the peaceful, beautifully landscaped yard, enclosed by a newer white picket fence. The main level also offers an elegant formal dining room and three generously sized bedrooms, including the luxurious primary suite. The primary retreat features a walk-in closet and spa-inspired bath with dual vanities, porcelain tile flooring, a frameless glass walk-in shower with marble walls, and on-trend lighting and hardware. Gorgeous hardwood stairs lead to the upper-level overlook, where wide-plank engineered hardwood flooring continues throughout two additional bedrooms and a beautifully renovated full bath with a glass-enclosed walk-in shower and porcelain tile flooring. The flexible five-bedroom layout provides exceptional space for guests, home offices, hobbies, and/or multigenerational living. Outside, the private and beautifully landscaped lot is equally impressive. A charming backyard shed has been customized with an automatic garage-style door to accommodate a golf cart, while the expansive driveway provides parking for four or more vehicles in addition to the two-car garage. Peaceful, private, and polished from top to bottom, this extraordinary home offers gracious indoor-outdoor living in a community designed for recreation, relaxation, and life near the water. This is more than a home—it is the Eastern Shore lifestyle you have been waiting for.

330 Prospect Bay Dr W, Grasonville

Listing courtesy of Samson Properties. Contact: 3017602136

$315,000

Bay City - Opportunity Knocking for Investor! This 3 Bedroom 1.5 Bath rancher features a new roof 2020, Siding and Windows in 2017. The property is .42 of an acre with a nice backyard. The blacktop drive and one car garage are some other nice features. The home needs TLC and updating inside. The property is being sold in AS-IS condition, inspections are for information purposes only. Solar panels are owned and not leased.

Bay City - Opportunity Knocking for Investor! This 3 Bedroom 1.5 Bath rancher features a new roof 2020, Siding and Windows in 2017. The property is .42 of an acre with a nice backyard. The blacktop drive and one car garage are some other nice features. The home needs TLC and updating inside. The property is being sold in AS-IS condition, inspections are for information purposes only. Solar panels are owned and not leased.

303 Charl Ct, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$375,000

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

2 Beds ⋅ 2 Baths

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

224 Ewingtown Rd, Church Hill

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$695,000

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

458 Eagle Manor Dr, Church Hill

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183

$1,150,000

NEW PRICE! Don't miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there's plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can't replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house — it's a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home.

2 Beds ⋅ 3 Baths

NEW PRICE! Don't miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there's plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can't replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house — it's a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home.

408 Butlers Lndg, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$545,000

Open House, Saturday, 9/12, 11:00am - 1:00pm; Welcome to 639 Poplar School Road, Centreville, where beautifully updated, move-in ready living meets the peace and privacy of a picturesque country setting—all just 20 minutes from the Chesapeake Bay Bridge. Lovingly maintained by the same owner for the past 26 years, this 3-bedroom, 2-full-bath home is situated on a beautifully landscaped 1-acre lot surrounded by mature trees. Step inside to a freshly and professionally painted interior filled with thoughtful updates and quality craftsmanship. The kitchen and bathrooms feature granite countertops and custom cabinetry, while additional improvements include replacement windows (2018), four new storm doors, updated lighting and ceiling fans, a 3-year-old heat pump, 1-year-old water heater, and a high-end water treatment and softener system. The spacious primary suite is enhanced by a beautifully designed custom Amish-built walk-in closet system, providing exceptional storage and organization. Looking for even more space? The upper level features a finished office/den, while the remaining unfinished area offers tremendous potential for future living space—whether you envision additional bedrooms, a recreation room, home gym, or hobby space. Outdoor living is equally impressive. Relax on the inviting screened porch, entertain on the expansive paver patio, or enjoy the fenced area surrounded by a classic white picket fence—ideal for children and pets. Beyond the patio, the expansive yard provides plenty of room to garden, play, entertain, or simply enjoy the peaceful Eastern Shore setting. The finished side-entry two-car garage features epoxy flooring and built-in shelving, providing excellent storage and workspace. For even more versatility, the impressive 29' x 28' Amish-built pole barn features electricity and is pre-plumbed, making it ideal for a workshop, hobbies, equipment, recreational vehicles, or additional storage. Beautifully updated and meticulously maintained, 639 Poplar School Road offers the acreage, privacy, outdoor living, abundant storage, and room to grow that make country living so appealing—without sacrificing convenience. You're just minutes from Historic Centreville, where you'll find local restaurants, shops, parks, the Centreville Wharf & Public Landing, and everyday conveniences, while remaining only 20 minutes from the Chesapeake Bay Bridge.

Open House, Saturday, 9/12, 11:00am - 1:00pm; Welcome to 639 Poplar School Road, Centreville, where beautifully updated, move-in ready living meets the peace and privacy of a picturesque country setting—all just 20 minutes from the Chesapeake Bay Bridge. Lovingly maintained by the same owner for the past 26 years, this 3-bedroom, 2-full-bath home is situated on a beautifully landscaped 1-acre lot surrounded by mature trees. Step inside to a freshly and professionally painted interior filled with thoughtful updates and quality craftsmanship. The kitchen and bathrooms feature granite countertops and custom cabinetry, while additional improvements include replacement windows (2018), four new storm doors, updated lighting and ceiling fans, a 3-year-old heat pump, 1-year-old water heater, and a high-end water treatment and softener system. The spacious primary suite is enhanced by a beautifully designed custom Amish-built walk-in closet system, providing exceptional storage and organization. Looking for even more space? The upper level features a finished office/den, while the remaining unfinished area offers tremendous potential for future living space—whether you envision additional bedrooms, a recreation room, home gym, or hobby space. Outdoor living is equally impressive. Relax on the inviting screened porch, entertain on the expansive paver patio, or enjoy the fenced area surrounded by a classic white picket fence—ideal for children and pets. Beyond the patio, the expansive yard provides plenty of room to garden, play, entertain, or simply enjoy the peaceful Eastern Shore setting. The finished side-entry two-car garage features epoxy flooring and built-in shelving, providing excellent storage and workspace. For even more versatility, the impressive 29' x 28' Amish-built pole barn features electricity and is pre-plumbed, making it ideal for a workshop, hobbies, equipment, recreational vehicles, or additional storage. Beautifully updated and meticulously maintained, 639 Poplar School Road offers the acreage, privacy, outdoor living, abundant storage, and room to grow that make country living so appealing—without sacrificing convenience. You're just minutes from Historic Centreville, where you'll find local restaurants, shops, parks, the Centreville Wharf & Public Landing, and everyday conveniences, while remaining only 20 minutes from the Chesapeake Bay Bridge.

639 Poplar School Rd, Centreville

Listing courtesy of Compass. Contact: (410) 429-7425

$575,000

Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

4 Beds ⋅ 4 Baths

Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

624 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$924,000

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

214 Bayberry Dr, Chester

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$315,000

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$599,999

Welcome to the Country - this beautifully maintained custom-built 3-bedroom, 2.5-bath home, perfectly situated on 3.34 picturesque acres with mature landscaping and plenty of room to relax, entertain, or operate a home-based business. Enjoy peaceful mornings on the inviting front porch or unwind on the cozy screened rear porch while taking in the beauty of nature. Inside, you'll find a warm and welcoming interior featuring a completely renovated kitchen with white cabinetry, quartz countertops, top-of-the-line stainless steel appliances, and stunning new luxury vinyl plank flooring throughout the house. The entire interior has new paint in Sherwin-Williams Agreeable Gray, creating a fresh, timeless feel. The spacious primary suite has an oversized walk-in closet and a luxurious private bath with a spa tub and separate shower. The partially finished basement offers additional heated and air-conditioned living space, perfect for a recreation room, home gym, additional bedroom or office. Recent updates and improvements include: Newer 3.5-ton HVAC system, new Lifetime Luxury Vinyl Plank flooring throughout, new, well pump with continuous pressure system, the tankless water heater professionally serviced, and the chimney professionally cleaned and serviced, Additional attic insulation has been added for improved energy efficiency. Outside, the property continues to impress with two exceptional outbuildings. A detached two-car garage is connected to the home by a convenient breezeway. The impressive 30' x 60' detached building offers endless possibilities with a workshop, 220-volt electric service, storage loft, office, and an expansive gathering/party room—ideal for entertaining, hobbies, car enthusiasts, or a small business. Conveniently located just 18 miles from Chestertown, Centreville, Dover, and Middletown, this one-of-a-kind property offers the perfect blend of country living and accessibility. If you've been searching for privacy, quality, and versatility, this exceptional property is one you won't want to miss!

Welcome to the Country - this beautifully maintained custom-built 3-bedroom, 2.5-bath home, perfectly situated on 3.34 picturesque acres with mature landscaping and plenty of room to relax, entertain, or operate a home-based business. Enjoy peaceful mornings on the inviting front porch or unwind on the cozy screened rear porch while taking in the beauty of nature. Inside, you'll find a warm and welcoming interior featuring a completely renovated kitchen with white cabinetry, quartz countertops, top-of-the-line stainless steel appliances, and stunning new luxury vinyl plank flooring throughout the house. The entire interior has new paint in Sherwin-Williams Agreeable Gray, creating a fresh, timeless feel. The spacious primary suite has an oversized walk-in closet and a luxurious private bath with a spa tub and separate shower. The partially finished basement offers additional heated and air-conditioned living space, perfect for a recreation room, home gym, additional bedroom or office. Recent updates and improvements include: Newer 3.5-ton HVAC system, new Lifetime Luxury Vinyl Plank flooring throughout, new, well pump with continuous pressure system, the tankless water heater professionally serviced, and the chimney professionally cleaned and serviced, Additional attic insulation has been added for improved energy efficiency. Outside, the property continues to impress with two exceptional outbuildings. A detached two-car garage is connected to the home by a convenient breezeway. The impressive 30' x 60' detached building offers endless possibilities with a workshop, 220-volt electric service, storage loft, office, and an expansive gathering/party room—ideal for entertaining, hobbies, car enthusiasts, or a small business. Conveniently located just 18 miles from Chestertown, Centreville, Dover, and Middletown, this one-of-a-kind property offers the perfect blend of country living and accessibility. If you've been searching for privacy, quality, and versatility, this exceptional property is one you won't want to miss!

620 Baxter Rd, Sudlersville

Listing courtesy of Taylor Properties. Contact:

$868,000

A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$1,250,000

Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

5 Beds ⋅ 3 Baths

Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$749,000

PRICED TO SELL - RARE OPPORTUNITY - Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful Golf Course Views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Brookhaven cabinets, Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida ( or four seasons) room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Select spaces have been refreshed with new interior paint and elegant crown molding (2025), adding a touch of sophistication and style. Recent improvements include Dual-Zone Hybrid HVAC (2024/2026): Customized upstairs/downstairs comfort with two brand-new 2026 Lennox HVAC units with heat pumps and smart thermostats, backed by a Navien tankless combi-boiler Installed in 2024 for ultra-efficient, multi-zone hydronic heating. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026). Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. The monthly HOA Fees INCLUDE Golf Membership and Greens Fees. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

PRICED TO SELL - RARE OPPORTUNITY - Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful Golf Course Views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Brookhaven cabinets, Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida ( or four seasons) room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Select spaces have been refreshed with new interior paint and elegant crown molding (2025), adding a touch of sophistication and style. Recent improvements include Dual-Zone Hybrid HVAC (2024/2026): Customized upstairs/downstairs comfort with two brand-new 2026 Lennox HVAC units with heat pumps and smart thermostats, backed by a Navien tankless combi-boiler Installed in 2024 for ultra-efficient, multi-zone hydronic heating. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026). Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. The monthly HOA Fees INCLUDE Golf Membership and Greens Fees. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$1,275,000

WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$549,000

Huge price reduction.... 130 Opera Court in the sought after community of Symphony Village at Centreville. If you've been waiting for that home resting on an exceptional lot backing to an open area and woods, then this is the home you've been waiting for. The beautiful 4 bedroom, 3 full bath home is exceptional, move in ready and just waiting for you. As you enter the home, your eyes will be drawn to the bright open floorplan and the rear windows overlooking the large deck that expands across the entire rear of the home. On the right, you'll find the front guest bedroom/office, a second guest bedroom, full bath, laundry room and access to the garage and lower level of the home. Moving through the home, you'll pass through the large living area with double sided propane fireplace, mounted TV that conveys with the home and the relaxing area and dining area on the rear overlooking the large lot backing to beautiful woods. To the right is the gourmet kitchen with granite counters, appliances including a gas stove and under cabinet lighting. The expansive primary suite is a must see with French Doors leading to the balcony, his and her walk-in closets and the primary bath with a large walk-in corner shower. Moving to the lower level, you'll find a large family area, another guest bedroom, full bath, a massive amount of storage area and a workshop leading to the rear exterior of the home. This home rests on a premium wooded lot for your relaxation while enjoying the wildlife that the area has to offer.