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A short stroll from the Eastern Bay front community center, this brand new home is complete and ready for you to move in before the holidays! One level living with LVP flooring throughout the entire home! Quartz countertops on classic white shaker cabinets and stainless steel appliances complete the modern farmhouse feel of this kitchen. Split floor plan gives flexibility to the two guest rooms which could be used as an office or sitting room as well. Master suite is on the rear of the home with a spacious walk in closet and luxurious bathroom with double vanities, tiled shower, and more. Two car garage and full front porch bring the perfect blend of utility and charm.

214 Penny Ln, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$135,000

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly renovated bathrooms, light fixtures, fresh paint, trim, new wall to wall carpet, and LVP flooring. Buyers should independently verify achievable rents, however it should be noted recently rented townhomes in the area have ranged from $1,800-$2,000. Conveniently located near Washington College, Chestertown's shops, restaurants, and local amenities. Independent appraisal on file showing strong ARV potential. Property is being sold strictly as-is.

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly renovated bathrooms, light fixtures, fresh paint, trim, new wall to wall carpet, and LVP flooring. Buyers should independently verify achievable rents, however it should be noted recently rented townhomes in the area have ranged from $1,800-$2,000. Conveniently located near Washington College, Chestertown's shops, restaurants, and local amenities. Independent appraisal on file showing strong ARV potential. Property is being sold strictly as-is.

403 Calvert St, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$559,900

Welcome to 200 Anchor Lane, where the charm of an established Kent Island neighborhood meets the convenience of a nearly new home! Situated on a spacious 0.42-acre corner lot with NO HOA, this 3-bedroom, 2-bath rancher offers approximately 1,650 square feet of thoughtfully redesigned living space. Originally built in 1977, the home underwent an extensive renovation in 2025, taken down to the studs and rebuilt with modern finishes and systems while preserving its original textured masonry façade and chimney. Step inside to discover a bright, open-concept layout where the dining area flows seamlessly into the kitchen and family room. The beautifully appointed kitchen features Samsung Bespoke appliances, a gas range, generous cabinetry and an oversized island offering plenty of space for meal preparation, gathering and entertaining. The spacious primary suite includes a walk-in closet, additional closet and private bath with a walk-in shower and double vanity. Two additional bedrooms offer generous closet space and share a thoughtfully updated hall bath. Beyond the cosmetic improvements, nearly every major component has been updated, including electrical, plumbing, HVAC, roof, insulation, windows and doors! Additional features include smart lighting, whole-home audio, an EV charger, generator hookup, interior fire sprinkler system, conditioned and encapsulated crawlspace, and a NEW well installed in 2026. Enjoy outdoor living on the covered patio with plenty of yard space for gardening, recreation or simply relaxing. Located in the desirable Castle Marina area of Chester, this property puts the Eastern Shore lifestyle within easy reach! Just a few houses down from Castle Marina and Freedom Boat Club, boating enthusiasts will appreciate the convenient proximity to the water. Enjoy nearby dining, the Cross Island Trail and easy access to Route 50 for commuting to Annapolis, Baltimore and beyond. An exceptional opportunity to enjoy the benefits of extensive modern renovations in an established Kent Island location!

Welcome to 200 Anchor Lane, where the charm of an established Kent Island neighborhood meets the convenience of a nearly new home! Situated on a spacious 0.42-acre corner lot with NO HOA, this 3-bedroom, 2-bath rancher offers approximately 1,650 square feet of thoughtfully redesigned living space. Originally built in 1977, the home underwent an extensive renovation in 2025, taken down to the studs and rebuilt with modern finishes and systems while preserving its original textured masonry façade and chimney. Step inside to discover a bright, open-concept layout where the dining area flows seamlessly into the kitchen and family room. The beautifully appointed kitchen features Samsung Bespoke appliances, a gas range, generous cabinetry and an oversized island offering plenty of space for meal preparation, gathering and entertaining. The spacious primary suite includes a walk-in closet, additional closet and private bath with a walk-in shower and double vanity. Two additional bedrooms offer generous closet space and share a thoughtfully updated hall bath. Beyond the cosmetic improvements, nearly every major component has been updated, including electrical, plumbing, HVAC, roof, insulation, windows and doors! Additional features include smart lighting, whole-home audio, an EV charger, generator hookup, interior fire sprinkler system, conditioned and encapsulated crawlspace, and a NEW well installed in 2026. Enjoy outdoor living on the covered patio with plenty of yard space for gardening, recreation or simply relaxing. Located in the desirable Castle Marina area of Chester, this property puts the Eastern Shore lifestyle within easy reach! Just a few houses down from Castle Marina and Freedom Boat Club, boating enthusiasts will appreciate the convenient proximity to the water. Enjoy nearby dining, the Cross Island Trail and easy access to Route 50 for commuting to Annapolis, Baltimore and beyond. An exceptional opportunity to enjoy the benefits of extensive modern renovations in an established Kent Island location!

200 Anchor Ln, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$1,285,000

Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset views. Pier has a boat lift, water and electric. 4 MLW with an option to extend the pier 50' to get over 5 MLW. Plenty of room to expand the footprint or add a pool. Professional Photos to Come.

Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset views. Pier has a boat lift, water and electric. 4 MLW with an option to extend the pier 50' to get over 5 MLW. Plenty of room to expand the footprint or add a pool. Professional Photos to Come.

8710 Cummings Rd, Wittman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$375,000

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

4 Beds ⋅ 3 Baths

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

201 Garland Way, Chestertown

Listing courtesy of ERA Martin Associates. Contact:

$675,000

Designed for effortless, low-maintenance living, this beautifully appointed three-bedroom, 2.5-bath condominium offers approximately 2,600 square feet of thoughtfully designed living space, combining comfort, elegance, and an exceptional collection of resort-style amenities. The open-concept living, dining, and kitchen areas create a welcoming flow, ideal for both everyday living and entertaining. Expansive windows fill the home with natural light, while the inviting walk-out porch provides a peaceful setting overlooking ponds on two sides, with seasonal glimpses of the Chester River. The spacious primary suite is privately situated on one side of the residence and features a generous sitting room, two walk-in closets, and a comfortable retreat-like atmosphere. On the opposite side of the condominium, two additional private bedrooms, each with a walk-in closet, share a full bath, offering an ideal layout for family and guests. The well-appointed kitchen features 42-inch cabinetry, beautiful white quartz countertops with subtle gray veining, and a timeless neutral palette that provides the perfect canvas for your personal style. Located within the highly desirable Four Seasons community, residents enjoy an exceptional lifestyle with an impressive array of amenities. Highlights include indoor and outdoor swimming pools, tennis courts, playgrounds, fire pits, a community pier, kayak park with launch, and water access. The community also offers a spectacular 22,000-square-foot clubhouse, fitness facilities, inviting gathering rooms within each building, and multiple spaces designed for entertaining and socializing, including bar areas with televisions. Whether enjoying the peaceful pond views from your porch, taking advantage of the outstanding community amenities, or simply appreciating the ease of condominium living, this residence offers a wonderful opportunity to enjoy comfort, convenience, and a resort-inspired lifestyle. Walking trails bot in the community and right outside of community. Close commute to the bay bridge, shopping, churches and doctors and much more....

Designed for effortless, low-maintenance living, this beautifully appointed three-bedroom, 2.5-bath condominium offers approximately 2,600 square feet of thoughtfully designed living space, combining comfort, elegance, and an exceptional collection of resort-style amenities. The open-concept living, dining, and kitchen areas create a welcoming flow, ideal for both everyday living and entertaining. Expansive windows fill the home with natural light, while the inviting walk-out porch provides a peaceful setting overlooking ponds on two sides, with seasonal glimpses of the Chester River. The spacious primary suite is privately situated on one side of the residence and features a generous sitting room, two walk-in closets, and a comfortable retreat-like atmosphere. On the opposite side of the condominium, two additional private bedrooms, each with a walk-in closet, share a full bath, offering an ideal layout for family and guests. The well-appointed kitchen features 42-inch cabinetry, beautiful white quartz countertops with subtle gray veining, and a timeless neutral palette that provides the perfect canvas for your personal style. Located within the highly desirable Four Seasons community, residents enjoy an exceptional lifestyle with an impressive array of amenities. Highlights include indoor and outdoor swimming pools, tennis courts, playgrounds, fire pits, a community pier, kayak park with launch, and water access. The community also offers a spectacular 22,000-square-foot clubhouse, fitness facilities, inviting gathering rooms within each building, and multiple spaces designed for entertaining and socializing, including bar areas with televisions. Whether enjoying the peaceful pond views from your porch, taking advantage of the outstanding community amenities, or simply appreciating the ease of condominium living, this residence offers a wonderful opportunity to enjoy comfort, convenience, and a resort-inspired lifestyle. Walking trails bot in the community and right outside of community. Close commute to the bay bridge, shopping, churches and doctors and much more....

190 Harrier Way Unit 24, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$1,775,000

Exceptional Wye River Waterfront Living – A Boater’s Paradise! An extraordinary opportunity to enjoy the very best of Wye River waterfront living! Perfectly positioned atop a bluff, this beautifully maintained home captures breathtaking panoramic water views and offers an exceptional setting for boating enthusiasts and those who appreciate the beauty of waterfront living. With approximately 6 feet of water at the pier and a boat lift with a 12,000-pound capacity, this property is ready for your boating adventures. The southeast-facing orientation provides beautiful natural light and stunning water views throughout the home. Spend your days fishing and crabbing on the Wye, cruising to St. Michaels, or taking your boat to one of the area's wonderful waterfront restaurants for a memorable lunch or dinner. Conveniently located approximately six miles from Route 50, the property offers the perfect balance of a peaceful waterfront setting and accessibility. There is living space of 3,990 of finished sq. feet and an additional 350 unfinished sq. footage for a total of 4,340 sq. ft. Inside, the home is thoughtfully designed across three levels, offering generous living spaces and exceptional flexibility. There are two primary suites, one on the main level and another on the second floor. Hardwood flooring extends throughout much of the first floor, where expansive, open living areas take full advantage of the beautiful water views. The updated kitchen, spacious sunroom, three fireplaces, and abundant natural light create a warm and inviting atmosphere. Many rooms enjoy beautiful water views, making the river a constant backdrop to everyday living. An especially desirable feature for the area is the full basement, approximately three-quarters finished. This versatile space offers excellent possibilities for a home office or business setup, recreation room, home gym, or additional entertainment space. The third level provides three additional bedrooms and two full bathrooms, with all three bedrooms enjoying water views. A walkout deck overlooking the water creates another wonderful place to relax and take in the peaceful surroundings. Outdoor living is equally impressive. A large brick patio along the waterfront offers an ideal setting for entertaining and is ready for your vision of an outdoor kitchen. The expansive, open lawn and beautifully maintained landscaping provide plenty of room to enjoy the outdoors, gather with family and friends, or simply appreciate the privacy and natural beauty of this exceptional property. Meticulously maintained and thoughtfully designed for both comfortable everyday living and gracious entertaining, this Wye River waterfront home offers an exceptional combination of panoramic views, boating amenities, generous living spaces, and a convenient location. Experience the Wye River lifestyle—where boating, entertaining, and spectacular waterfront living come together!

Exceptional Wye River Waterfront Living – A Boater’s Paradise! An extraordinary opportunity to enjoy the very best of Wye River waterfront living! Perfectly positioned atop a bluff, this beautifully maintained home captures breathtaking panoramic water views and offers an exceptional setting for boating enthusiasts and those who appreciate the beauty of waterfront living. With approximately 6 feet of water at the pier and a boat lift with a 12,000-pound capacity, this property is ready for your boating adventures. The southeast-facing orientation provides beautiful natural light and stunning water views throughout the home. Spend your days fishing and crabbing on the Wye, cruising to St. Michaels, or taking your boat to one of the area's wonderful waterfront restaurants for a memorable lunch or dinner. Conveniently located approximately six miles from Route 50, the property offers the perfect balance of a peaceful waterfront setting and accessibility. There is living space of 3,990 of finished sq. feet and an additional 350 unfinished sq. footage for a total of 4,340 sq. ft. Inside, the home is thoughtfully designed across three levels, offering generous living spaces and exceptional flexibility. There are two primary suites, one on the main level and another on the second floor. Hardwood flooring extends throughout much of the first floor, where expansive, open living areas take full advantage of the beautiful water views. The updated kitchen, spacious sunroom, three fireplaces, and abundant natural light create a warm and inviting atmosphere. Many rooms enjoy beautiful water views, making the river a constant backdrop to everyday living. An especially desirable feature for the area is the full basement, approximately three-quarters finished. This versatile space offers excellent possibilities for a home office or business setup, recreation room, home gym, or additional entertainment space. The third level provides three additional bedrooms and two full bathrooms, with all three bedrooms enjoying water views. A walkout deck overlooking the water creates another wonderful place to relax and take in the peaceful surroundings. Outdoor living is equally impressive. A large brick patio along the waterfront offers an ideal setting for entertaining and is ready for your vision of an outdoor kitchen. The expansive, open lawn and beautifully maintained landscaping provide plenty of room to enjoy the outdoors, gather with family and friends, or simply appreciate the privacy and natural beauty of this exceptional property. Meticulously maintained and thoughtfully designed for both comfortable everyday living and gracious entertaining, this Wye River waterfront home offers an exceptional combination of panoramic views, boating amenities, generous living spaces, and a convenient location. Experience the Wye River lifestyle—where boating, entertaining, and spectacular waterfront living come together!

377 Hemsley Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

$27,000

Ocean Gtwy, Trappe

Listing courtesy of Meredith Fine Properties. Contact:

$550,000

Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

709 Chesapeake Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

$1,125,000

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

5 Beds ⋅ 4 Baths

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$550,000

AN EXCEPTIONAL OPPORTUNITY IN PROSPECT BAY! Discover an attractively priced opportunity to enjoy the exceptional lifestyle of this sought-after waterfront and golf community. Offered at $550,000, this distinctive contemporary home is nestled on approximately one acre surrounded by mature trees and peaceful natural surroundings. Offering nearly 2,850 square feet of living space, the residence features three bedrooms, two-and-a-half baths, and a versatile floor plan with two main-level bedrooms. The impressive great room showcases soaring vaulted ceilings, a dramatic brick fireplace, and expansive glass doors opening to a spacious deck and tranquil wooded setting. Abundant natural light fills the interior, creating a wonderful connection between indoor and outdoor living. Overlooking the great room, a generously sized loft offers wonderful flexibility for a home office, creative studio, additional gathering space, or the potential for a fourth bedroom with appropriate modifications and approvals. The generously sized kitchen features abundant cabinetry, a center island, and an adjoining breakfast area, offering plenty of space and possibilities for personalization. Significant improvements include a roof and HVAC system replaced in 2021. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own.

AN EXCEPTIONAL OPPORTUNITY IN PROSPECT BAY! Discover an attractively priced opportunity to enjoy the exceptional lifestyle of this sought-after waterfront and golf community. Offered at $550,000, this distinctive contemporary home is nestled on approximately one acre surrounded by mature trees and peaceful natural surroundings. Offering nearly 2,850 square feet of living space, the residence features three bedrooms, two-and-a-half baths, and a versatile floor plan with two main-level bedrooms. The impressive great room showcases soaring vaulted ceilings, a dramatic brick fireplace, and expansive glass doors opening to a spacious deck and tranquil wooded setting. Abundant natural light fills the interior, creating a wonderful connection between indoor and outdoor living. Overlooking the great room, a generously sized loft offers wonderful flexibility for a home office, creative studio, additional gathering space, or the potential for a fourth bedroom with appropriate modifications and approvals. The generously sized kitchen features abundant cabinetry, a center island, and an adjoining breakfast area, offering plenty of space and possibilities for personalization. Significant improvements include a roof and HVAC system replaced in 2021. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own.

24 Fairway Is, Grasonville

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

$499,900

Welcome to this lovely corner-lot home in desirable Easton Club East, offering 2,342 square feet of thoughtfully designed living space in Del Webb’s popular two-story Wittman model. A welcoming entry introduces beautiful architectural details and a spacious, well-appointed floor plan designed for comfortable everyday living and effortless entertaining. The elegant formal dining room features a tray ceiling, providing a wonderful setting for gatherings and special occasions. The bright, spacious kitchen offers a center island, pantry, abundant cabinetry, and a generous casual dining area. Just beyond, the inviting great room showcases a soaring vaulted ceiling, solar tubes that fill the space with natural light, and a cozy gas fireplace. A lovely sun room provides additional space to relax and unwind, while a dedicated main-level office offers the convenience of working from home. The first-floor primary suite features a spacious walk-in closet and private bath complete with dual vanities, a walk-in shower, and a soaking tub. A second bedroom, full hall bath, and convenient laundry room complete the main level. Upstairs, a fabulous loft-style family room provides a versatile second living area, perfect for relaxing, entertaining, or accommodating guests. A third bedroom and full bath offer additional privacy and flexibility, making this level ideal for extended family or multi generational living. Outside, mature landscaping creates a lovely sense of privacy around the patio, offering a peaceful setting for outdoor enjoyment. Additional highlights include a two-car rear-loading garage, generous driveway, and a new roof installed in 2023. Residents of Easton Club East enjoy an exceptional collection of community amenities, including a clubhouse with fitness room, library, and entertainment space; outdoor swimming pool; tennis and pickleball courts; bocce ball; putting green; picnic areas; gazebos; and scenic walking trails. The community also offers a convenient location for commuting, shopping, dining, and enjoying all that the Eastern Shore has to offer. An Important Distinction: This home is located in the non-age-restricted section of Easton Club East, meaning buyers are not required to be 55 or older. Residents enjoy the same community amenities and are subject to the same HOA dues and regulations.ties.

Welcome to this lovely corner-lot home in desirable Easton Club East, offering 2,342 square feet of thoughtfully designed living space in Del Webb’s popular two-story Wittman model. A welcoming entry introduces beautiful architectural details and a spacious, well-appointed floor plan designed for comfortable everyday living and effortless entertaining. The elegant formal dining room features a tray ceiling, providing a wonderful setting for gatherings and special occasions. The bright, spacious kitchen offers a center island, pantry, abundant cabinetry, and a generous casual dining area. Just beyond, the inviting great room showcases a soaring vaulted ceiling, solar tubes that fill the space with natural light, and a cozy gas fireplace. A lovely sun room provides additional space to relax and unwind, while a dedicated main-level office offers the convenience of working from home. The first-floor primary suite features a spacious walk-in closet and private bath complete with dual vanities, a walk-in shower, and a soaking tub. A second bedroom, full hall bath, and convenient laundry room complete the main level. Upstairs, a fabulous loft-style family room provides a versatile second living area, perfect for relaxing, entertaining, or accommodating guests. A third bedroom and full bath offer additional privacy and flexibility, making this level ideal for extended family or multi generational living. Outside, mature landscaping creates a lovely sense of privacy around the patio, offering a peaceful setting for outdoor enjoyment. Additional highlights include a two-car rear-loading garage, generous driveway, and a new roof installed in 2023. Residents of Easton Club East enjoy an exceptional collection of community amenities, including a clubhouse with fitness room, library, and entertainment space; outdoor swimming pool; tennis and pickleball courts; bocce ball; putting green; picnic areas; gazebos; and scenic walking trails. The community also offers a convenient location for commuting, shopping, dining, and enjoying all that the Eastern Shore has to offer. An Important Distinction: This home is located in the non-age-restricted section of Easton Club East, meaning buyers are not required to be 55 or older. Residents enjoy the same community amenities and are subject to the same HOA dues and regulations.ties.

29709 Lyons Dr, Easton

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

$425,000

Close to the Beach, Restaurants, and Marinas in Rock Hall This well-loved and nicely cared-for solid brick rancher sits on a quiet street, offering the perfect blend of peaceful living and incredible convenience. The property features excellent curb appeal, mature landscaping, ample parking, and an oversized detached concrete garage built to match the house. It is completely ready for its next owner to move right in and make it their own. Comfortable Living & Layout • Open Kitchen & Dining: The heart of the home features a generous open kitchen and dining area, creating a wonderful space for meals and gathering. • All-Season Room: Located right off the dining area, the sun-filled all-season room expands your living space year-round. • Living Room: A cozy living room features a classic wood-burning fireplace that provides warmth and charm for the fall and winter seasons, along with a roomy bow window that lets in plenty of natural light and offers great space for plant lovers. • Bedrooms & Baths: The single-level floor plan includes three bedrooms, one full bathroom, and one half bath. • Den & Mudroom: A separate den offers flexible space, while a large utility room serves as a functional laundry, mudroom, and extra storage area. • Flooring: Beautiful hardwood floors run throughout most of the home, complemented by durable tile in select areas. Perfect Rock Hall Location Situated on a quiet, low-traffic street, this location is ideal for enjoying everything the area has to offer: • Walking distance to the beach, quaint shops, local restaurants, and marinas. Community pool is only minutes away if you choose to get a quick cool-down. • An easy, flat area for riding bikes and getting your daily walks in. • A spacious yard featuring mature landscaping. Whether you are looking for a full-time residence or a cozy, low-maintenance getaway for weekends and holidays, this solid brick home is a must-see. Additional Note Home is being sold as is. The backyard features an established concrete pool that has been in place for years and well-enjoyed. For informational purposes, the seller has a current estimate for you to repair the concrete pool or, if a pool isn't on your list, an estimate to fill it in.

Close to the Beach, Restaurants, and Marinas in Rock Hall This well-loved and nicely cared-for solid brick rancher sits on a quiet street, offering the perfect blend of peaceful living and incredible convenience. The property features excellent curb appeal, mature landscaping, ample parking, and an oversized detached concrete garage built to match the house. It is completely ready for its next owner to move right in and make it their own. Comfortable Living & Layout • Open Kitchen & Dining: The heart of the home features a generous open kitchen and dining area, creating a wonderful space for meals and gathering. • All-Season Room: Located right off the dining area, the sun-filled all-season room expands your living space year-round. • Living Room: A cozy living room features a classic wood-burning fireplace that provides warmth and charm for the fall and winter seasons, along with a roomy bow window that lets in plenty of natural light and offers great space for plant lovers. • Bedrooms & Baths: The single-level floor plan includes three bedrooms, one full bathroom, and one half bath. • Den & Mudroom: A separate den offers flexible space, while a large utility room serves as a functional laundry, mudroom, and extra storage area. • Flooring: Beautiful hardwood floors run throughout most of the home, complemented by durable tile in select areas. Perfect Rock Hall Location Situated on a quiet, low-traffic street, this location is ideal for enjoying everything the area has to offer: • Walking distance to the beach, quaint shops, local restaurants, and marinas. Community pool is only minutes away if you choose to get a quick cool-down. • An easy, flat area for riding bikes and getting your daily walks in. • A spacious yard featuring mature landscaping. Whether you are looking for a full-time residence or a cozy, low-maintenance getaway for weekends and holidays, this solid brick home is a must-see. Additional Note Home is being sold as is. The backyard features an established concrete pool that has been in place for years and well-enjoyed. For informational purposes, the seller has a current estimate for you to repair the concrete pool or, if a pool isn't on your list, an estimate to fill it in.

5705 Walnut St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$365,000

Welcome to Stoney Ridge Farm in Easton, Maryland! This 4-bedroom, 2-full-bath split-level home presents an excellent opportunity for buyers looking to make a home their own while building equity through improvements. Offering a versatile split-level floor plan, this property provides a great starting point for those ready to bring their ideas and personal touches to life. While the home could benefit from updating and cosmetic improvements, it offers the opportunity for the next owner to customize the property to their preferences and potentially reap the benefits of their own sweat equity. Whether making improvements over time or planning a more extensive renovation, the possibilities are worth exploring. Located in the established Stoney Ridge Farm neighborhood, the property offers convenient access to Easton's shopping, dining, and local amenities. For buyers seeking an opportunity to enter the Easton housing market and create value through thoughtful improvements, this home is certainly worth considering. Bring your vision and explore the potential this property has to offer!

4 Beds ⋅ 2 Baths

Welcome to Stoney Ridge Farm in Easton, Maryland! This 4-bedroom, 2-full-bath split-level home presents an excellent opportunity for buyers looking to make a home their own while building equity through improvements. Offering a versatile split-level floor plan, this property provides a great starting point for those ready to bring their ideas and personal touches to life. While the home could benefit from updating and cosmetic improvements, it offers the opportunity for the next owner to customize the property to their preferences and potentially reap the benefits of their own sweat equity. Whether making improvements over time or planning a more extensive renovation, the possibilities are worth exploring. Located in the established Stoney Ridge Farm neighborhood, the property offers convenient access to Easton's shopping, dining, and local amenities. For buyers seeking an opportunity to enter the Easton housing market and create value through thoughtful improvements, this home is certainly worth considering. Bring your vision and explore the potential this property has to offer!

29430 Corbin Pkwy, Easton

Listing courtesy of Sid Sells Maryland Realty. Contact:

$320,000

***COMING SOON*** Freshly painted, new kitchen cabinets, new carpet throughout. This spacious 3 bedroom, 2.5 bath, 2 story condo is move in ready and available immediately. More info to come.

***COMING SOON*** Freshly painted, new kitchen cabinets, new carpet throughout. This spacious 3 bedroom, 2.5 bath, 2 story condo is move in ready and available immediately. More info to come.

55 Queen Caroline Ct, Chester

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

$1,895,000

Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Martingham community. This exquisite residence has been freshly painted and boasts 5 spacious bedrooms and 5.5 totally updated bathrooms. The primary bath has an expansive steam shower, soaker tub and heated floors for those chilly mornings. The heart of the home features a spacious gourmet kitchen equipped with stainless steel appliances, including a Kitchen Aid refrigerator, Wolf double oven, Wolf 5 burner gas cooktop and Cove dishwasher. Major renovations completed in 2026 include new roof with exposed copper valleys, copper gutters, windows and doors on the back of the house of the 1st floor have been replaced, new air handler on the 3rd floor, attic vent foam insulation, crawlspace has been encapsulated with sump pump and dehumidifier, irrigation and landscaping all have elevated this property to new heights, ensuring modern amenities while preserving its classic charm. Enjoy the ambience of two brick fireplaces, the convenience of an upper-floor laundry, and the tranquility of newly finished hardwood flooring throughout. The expansive private 2.34-acre lot faces the 14th hole of The Links at Perry Cabin picturesque golf course, offering a serene backdrop for outdoor gatherings. Step outside to your personal oasis, complete with a saltwater gunite pool, perfect for summer relaxation. The community enhances your lifestyle with well-maintained common areas and a waterfront picnic area for homeowners. This home is not just a residence; it's a lifestyle. There is nothing left to do but move your furniture in. Don't miss your chance to own this exceptional property!

5 Beds ⋅ 6 Baths

Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Martingham community. This exquisite residence has been freshly painted and boasts 5 spacious bedrooms and 5.5 totally updated bathrooms. The primary bath has an expansive steam shower, soaker tub and heated floors for those chilly mornings. The heart of the home features a spacious gourmet kitchen equipped with stainless steel appliances, including a Kitchen Aid refrigerator, Wolf double oven, Wolf 5 burner gas cooktop and Cove dishwasher. Major renovations completed in 2026 include new roof with exposed copper valleys, copper gutters, windows and doors on the back of the house of the 1st floor have been replaced, new air handler on the 3rd floor, attic vent foam insulation, crawlspace has been encapsulated with sump pump and dehumidifier, irrigation and landscaping all have elevated this property to new heights, ensuring modern amenities while preserving its classic charm. Enjoy the ambience of two brick fireplaces, the convenience of an upper-floor laundry, and the tranquility of newly finished hardwood flooring throughout. The expansive private 2.34-acre lot faces the 14th hole of The Links at Perry Cabin picturesque golf course, offering a serene backdrop for outdoor gatherings. Step outside to your personal oasis, complete with a saltwater gunite pool, perfect for summer relaxation. The community enhances your lifestyle with well-maintained common areas and a waterfront picnic area for homeowners. This home is not just a residence; it's a lifestyle. There is nothing left to do but move your furniture in. Don't miss your chance to own this exceptional property!

9450 Canvasback Way, St Michaels

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

$135,000

One story manufactured mobile home, located in a thriving and active Hyde Park, a 55+ Community With a 8 x 10 shed, handicap ramp, three-season room to relax. Hyde Park amenities include walking trails, dog park, shuffle board and picnic areas, pool, workout room, boat & Rv storage. Buyers must be approved by Hyde Park before any offer.

2 Beds ⋅ 2 Baths

One story manufactured mobile home, located in a thriving and active Hyde Park, a 55+ Community With a 8 x 10 shed, handicap ramp, three-season room to relax. Hyde Park amenities include walking trails, dog park, shuffle board and picnic areas, pool, workout room, boat & Rv storage. Buyers must be approved by Hyde Park before any offer.

17 Downing St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$549,000

Experience the charm of Eastern Shore living at 618 Love Point Road, where timeless farmhouse character meets modern comfort in the heart of Stevensville. Just moments from historic downtown Stevensville, Old Love Point Park, and Kent Island High School, this beautifully restored home offers an inviting combination of character, convenience, and coastal lifestyle. Offering more than 2,300 square feet of thoughtfully updated living space, this three-bedroom, two-and-a-half-bath residence blends classic architectural details with modern finishes. Hardwood floors, abundant natural light, fresh interior paint, and new window treatments create a warm and welcoming atmosphere throughout. The main level flows effortlessly from the inviting living room into the dining area and beautifully appointed kitchen. Designed for both everyday living and entertaining, the kitchen features custom cabinetry, a classic farmhouse sink, and a built-in coffee bar with wine cooler. A newer roof and previously updated major utilities provide additional peace of mind. Upstairs, three comfortable bedrooms and two tastefully renovated bathrooms offer inviting private retreats. Outside, the expansive, level backyard provides a wonderful setting for entertaining, recreation, or simply relaxing. Beautiful landscaping and a charming gazebo create an inviting outdoor retreat, while a detached bonus space offers exceptional versatility for a home office, fitness studio, creative workspace, or additional recreational space. The location is equally appealing. Enjoy morning coffee on the front porch, take a leisurely stroll through Old Love Point Park, or walk or bike into historic downtown Stevensville to explore its restaurants, coffee shops, and boutiques. Convenient access to Route 50 and the Chesapeake Bay Bridge makes commuting to Annapolis and beyond a breeze. With its classic farmhouse appeal, modern updates, generous outdoor space, and desirable Kent Island location, 618 Love Point Road offers an exceptional opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore.

Experience the charm of Eastern Shore living at 618 Love Point Road, where timeless farmhouse character meets modern comfort in the heart of Stevensville. Just moments from historic downtown Stevensville, Old Love Point Park, and Kent Island High School, this beautifully restored home offers an inviting combination of character, convenience, and coastal lifestyle. Offering more than 2,300 square feet of thoughtfully updated living space, this three-bedroom, two-and-a-half-bath residence blends classic architectural details with modern finishes. Hardwood floors, abundant natural light, fresh interior paint, and new window treatments create a warm and welcoming atmosphere throughout. The main level flows effortlessly from the inviting living room into the dining area and beautifully appointed kitchen. Designed for both everyday living and entertaining, the kitchen features custom cabinetry, a classic farmhouse sink, and a built-in coffee bar with wine cooler. A newer roof and previously updated major utilities provide additional peace of mind. Upstairs, three comfortable bedrooms and two tastefully renovated bathrooms offer inviting private retreats. Outside, the expansive, level backyard provides a wonderful setting for entertaining, recreation, or simply relaxing. Beautiful landscaping and a charming gazebo create an inviting outdoor retreat, while a detached bonus space offers exceptional versatility for a home office, fitness studio, creative workspace, or additional recreational space. The location is equally appealing. Enjoy morning coffee on the front porch, take a leisurely stroll through Old Love Point Park, or walk or bike into historic downtown Stevensville to explore its restaurants, coffee shops, and boutiques. Convenient access to Route 50 and the Chesapeake Bay Bridge makes commuting to Annapolis and beyond a breeze. With its classic farmhouse appeal, modern updates, generous outdoor space, and desirable Kent Island location, 618 Love Point Road offers an exceptional opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore.

618 Love Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact:

$698,000

Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanian’s Four Seasons at Kent Island. This highly coveted "Chester" floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views of the Chester River from nearly every vantage point. The view is further enhanced by a serene, fountain-appointed pond surrounded by vibrant seasonal foliage, creating a dramatic, panoramic nature backdrop. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious dining and great room with two tray ceilings anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, a spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by and birds soar. Two walk-in closets plus an additional wardrobe closet bring a sense of order and comfort. Complete with an attached garage and dedicated storage, this lock-and-leave sanctuary offers the effortless Eastern Shore lifestyle you deserve. Living here feels like a permanent vacation. Enjoy world-class community amenities, including 24,000 sq. ft. clubhouse, indoor and outdoor pools and jacuzzis with tiki huts, a state-of-the-art fitness center, game rooms, tennis, basketball, pickleball, and bocce courts, a dog park, a playground, an outdoor concert arena, and a community pier.

2 Beds ⋅ 3 Baths

Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanian’s Four Seasons at Kent Island. This highly coveted "Chester" floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views of the Chester River from nearly every vantage point. The view is further enhanced by a serene, fountain-appointed pond surrounded by vibrant seasonal foliage, creating a dramatic, panoramic nature backdrop. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious dining and great room with two tray ceilings anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, a spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by and birds soar. Two walk-in closets plus an additional wardrobe closet bring a sense of order and comfort. Complete with an attached garage and dedicated storage, this lock-and-leave sanctuary offers the effortless Eastern Shore lifestyle you deserve. Living here feels like a permanent vacation. Enjoy world-class community amenities, including 24,000 sq. ft. clubhouse, indoor and outdoor pools and jacuzzis with tiki huts, a state-of-the-art fitness center, game rooms, tennis, basketball, pickleball, and bocce courts, a dog park, a playground, an outdoor concert arena, and a community pier.

121 Switchgrass Way Unit 42, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

$459,900

Welcome to 8496 Colony Circle in the desirable Matthewstown Run neighborhood! This well-maintained 4-bedroom, 2.5-bath home offers a great combination of comfortable living space and outdoor amenities. The home features an updated kitchen with stainless steel appliances, a newer roof, and a welcoming front porch. Out back, you'll find a spacious rear yard with a large deck and above-ground pool, providing plenty of room for entertaining friends and family or enjoying the warmer months. Conveniently located just minutes from downtown Easton, with easy access to local shops, restaurants, schools, and other amenities. Don't miss this great opportunity to own a home in the established Matthewstown Run community!

4 Beds ⋅ 3 Baths

Welcome to 8496 Colony Circle in the desirable Matthewstown Run neighborhood! This well-maintained 4-bedroom, 2.5-bath home offers a great combination of comfortable living space and outdoor amenities. The home features an updated kitchen with stainless steel appliances, a newer roof, and a welcoming front porch. Out back, you'll find a spacious rear yard with a large deck and above-ground pool, providing plenty of room for entertaining friends and family or enjoying the warmer months. Conveniently located just minutes from downtown Easton, with easy access to local shops, restaurants, schools, and other amenities. Don't miss this great opportunity to own a home in the established Matthewstown Run community!

8496 Colony Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$429,900

This charming ranch-style home, built in 1978, offers a serene retreat on a spacious 0.33-acre lot, perfect for those who appreciate the beauty of nature. With three cozy bedrooms and two full bathrooms, this residence is designed for comfort and ease. The inviting screened porch and deck provide ideal spaces for morning coffee or evening gatherings, allowing you to soak in the tranquil surroundings. The driveway accommodates four or more vehicles, ensuring convenience for you and your guests. Imagine evenings spent enjoying the gentle sounds of nature, or hosting barbecues on the deck. This home is not just a place to live it's where memories are made. Embrace the lifestyle you've always wanted in this delightful property that beautifully blends comfort with the allure of outdoor living. Updated Kitchen Cabinets and appliances. Fresh painting throughout and new carpeting in primary bedroom.

This charming ranch-style home, built in 1978, offers a serene retreat on a spacious 0.33-acre lot, perfect for those who appreciate the beauty of nature. With three cozy bedrooms and two full bathrooms, this residence is designed for comfort and ease. The inviting screened porch and deck provide ideal spaces for morning coffee or evening gatherings, allowing you to soak in the tranquil surroundings. The driveway accommodates four or more vehicles, ensuring convenience for you and your guests. Imagine evenings spent enjoying the gentle sounds of nature, or hosting barbecues on the deck. This home is not just a place to live it's where memories are made. Embrace the lifestyle you've always wanted in this delightful property that beautifully blends comfort with the allure of outdoor living. Updated Kitchen Cabinets and appliances. Fresh painting throughout and new carpeting in primary bedroom.

206 Penny Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

$729,900

**Chesapeake Bay views, nearly new construction, and an opportunity to turn your coastal getaway into a potential income-producing investment!** Welcome to 335 South Carolina Road in Stevensville, where modern comfort meets the laid-back lifestyle of Maryland's Eastern Shore. Offering 4 bedrooms, 3.5 bathrooms, multiple living spaces, and THREE decks - 2 with expansive views of the Chesapeake Bay, this nearly new home delivers the perfect combination of space, comfort, and coastal charm. Step inside to discover luxury vinyl plank flooring throughout the main living areas and a beautifully appointed kitchen featuring quartz countertops, a spacious island with seating and additional storage, and plenty of room for gathering and entertaining. Multiple living spaces provide flexibility for relaxing, hosting overnight guests, working from home, or accommodating extended stays. But the real magic happens outside! Imagine starting your mornings with coffee overlooking the Chesapeake Bay, spending afternoons at the community beach, and ending your evenings gathered around the fire pit beneath the stars. With three decks, a spacious yard, and a storage shed, there's plenty of room to enjoy the outdoors and embrace the waterfront lifestyle. **Looking for a home that could work for you even when you're not there?** With its desirable Chesapeake Bay setting, generous accommodations, multiple outdoor entertaining areas, and access to the community beach, this property presents an exciting opportunity for buyers interested in exploring short-term rental income through platforms such as Airbnb or VRBO, subject to applicable regulations and approvals. Whether you're searching for a year-round residence, a weekend escape, a second home with potential rental income, or an investment opportunity, 335 South Carolina Road offers the flexibility to make your Eastern Shore dreams a reality. **Why just dream about life at the Bay when you could be living it—and potentially earning income from it, too?**Short-term rental use and income potential are subject to buyer verification of all applicable county regulations, licensing requirements, and community restrictions.

**Chesapeake Bay views, nearly new construction, and an opportunity to turn your coastal getaway into a potential income-producing investment!** Welcome to 335 South Carolina Road in Stevensville, where modern comfort meets the laid-back lifestyle of Maryland's Eastern Shore. Offering 4 bedrooms, 3.5 bathrooms, multiple living spaces, and THREE decks - 2 with expansive views of the Chesapeake Bay, this nearly new home delivers the perfect combination of space, comfort, and coastal charm. Step inside to discover luxury vinyl plank flooring throughout the main living areas and a beautifully appointed kitchen featuring quartz countertops, a spacious island with seating and additional storage, and plenty of room for gathering and entertaining. Multiple living spaces provide flexibility for relaxing, hosting overnight guests, working from home, or accommodating extended stays. But the real magic happens outside! Imagine starting your mornings with coffee overlooking the Chesapeake Bay, spending afternoons at the community beach, and ending your evenings gathered around the fire pit beneath the stars. With three decks, a spacious yard, and a storage shed, there's plenty of room to enjoy the outdoors and embrace the waterfront lifestyle. **Looking for a home that could work for you even when you're not there?** With its desirable Chesapeake Bay setting, generous accommodations, multiple outdoor entertaining areas, and access to the community beach, this property presents an exciting opportunity for buyers interested in exploring short-term rental income through platforms such as Airbnb or VRBO, subject to applicable regulations and approvals. Whether you're searching for a year-round residence, a weekend escape, a second home with potential rental income, or an investment opportunity, 335 South Carolina Road offers the flexibility to make your Eastern Shore dreams a reality. **Why just dream about life at the Bay when you could be living it—and potentially earning income from it, too?**Short-term rental use and income potential are subject to buyer verification of all applicable county regulations, licensing requirements, and community restrictions.

335 S Carolina Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

$495,000

Welcome to 7311 Madaline Avenue in desirable Easton Club East, a Chesapeake by Del Webb community. Built by Pulte Builders, the popular Vanderbilt model offers a wonderfully flexible floor plan, generous living spaces, and a beautiful park-like setting, all of this in a well maintained home featuring a newer roof create an inviting Eastern Shore retreat. Thoughtfully designed for comfortable everyday living and entertaining, this home features nine-foot ceilings, an adaptable living and dining area, and an additional flexible living space with built-in shelving, ideal for a home office, music room, or quiet retreat. The inviting family room features a gas fireplace, built-in cabinetry, and recessed lighting, opening to a cheerful breakfast area and well-appointed kitchen with granite countertops, gas cooking, and convenient pantry storage. One of the home’s most outstanding features is its beautiful new screened-in porch, extending the living space outdoors and providing a peaceful place to relax, entertain, or simply enjoy the natural surroundings. Overlooking a picturesque, park-like setting framed by mature trees and walking path, this delightful outdoor retreat offers wonderful opportunities to appreciate the changing seasons from many areas within the home. The spacious primary suite features a tray ceiling, private bath with soaking tub and separate shower, and an exceptionally generous walk-in closet with thoughtfully designed organizers, abundant shelving, and pull-out drawers. An additional bedroom, full hall bath, and versatile office or music room provide flexibility for guests, hobbies, or working from home. A convenient laundry and mudroom area, abundant storage, and attached two-car garage complete the home’s practical amenities. Easton Club East is a beautifully established 55+ community offering an exceptional array of amenities, including an impressive clubhouse with fitness center, outdoor swimming pool, tennis and pickleball courts, bocce, walking paths, scenic ponds, and attractively maintained common areas. A full-time lifestyle director coordinates a variety of clubs, social gatherings, recreational activities, and special events, creating a welcoming and engaging community atmosphere. Lawn maintenance and snow removal add to the appeal of easy, low-maintenance living. Just minutes away, historic downtown Easton offers an outstanding selection of restaurants, charming boutiques, art galleries, and cultural attractions, including the renowned Avalon Theatre and Academy Art Museum. Quality medical facilities, shopping, and everyday conveniences are nearby, while the picturesque waterfront villages of St. Michaels and Oxford, the Chesapeake Bay, and the many recreational opportunities of Maryland’s Eastern Shore are within easy reach. Discover the wonderful combination of comfort, flexibility, natural beauty, and community at 7311 Madaline Avenue—a delightful place to enjoy your next chapter of Eastern Shore living.

2 Beds ⋅ 2 Baths

Welcome to 7311 Madaline Avenue in desirable Easton Club East, a Chesapeake by Del Webb community. Built by Pulte Builders, the popular Vanderbilt model offers a wonderfully flexible floor plan, generous living spaces, and a beautiful park-like setting, all of this in a well maintained home featuring a newer roof create an inviting Eastern Shore retreat. Thoughtfully designed for comfortable everyday living and entertaining, this home features nine-foot ceilings, an adaptable living and dining area, and an additional flexible living space with built-in shelving, ideal for a home office, music room, or quiet retreat. The inviting family room features a gas fireplace, built-in cabinetry, and recessed lighting, opening to a cheerful breakfast area and well-appointed kitchen with granite countertops, gas cooking, and convenient pantry storage. One of the home’s most outstanding features is its beautiful new screened-in porch, extending the living space outdoors and providing a peaceful place to relax, entertain, or simply enjoy the natural surroundings. Overlooking a picturesque, park-like setting framed by mature trees and walking path, this delightful outdoor retreat offers wonderful opportunities to appreciate the changing seasons from many areas within the home. The spacious primary suite features a tray ceiling, private bath with soaking tub and separate shower, and an exceptionally generous walk-in closet with thoughtfully designed organizers, abundant shelving, and pull-out drawers. An additional bedroom, full hall bath, and versatile office or music room provide flexibility for guests, hobbies, or working from home. A convenient laundry and mudroom area, abundant storage, and attached two-car garage complete the home’s practical amenities. Easton Club East is a beautifully established 55+ community offering an exceptional array of amenities, including an impressive clubhouse with fitness center, outdoor swimming pool, tennis and pickleball courts, bocce, walking paths, scenic ponds, and attractively maintained common areas. A full-time lifestyle director coordinates a variety of clubs, social gatherings, recreational activities, and special events, creating a welcoming and engaging community atmosphere. Lawn maintenance and snow removal add to the appeal of easy, low-maintenance living. Just minutes away, historic downtown Easton offers an outstanding selection of restaurants, charming boutiques, art galleries, and cultural attractions, including the renowned Avalon Theatre and Academy Art Museum. Quality medical facilities, shopping, and everyday conveniences are nearby, while the picturesque waterfront villages of St. Michaels and Oxford, the Chesapeake Bay, and the many recreational opportunities of Maryland’s Eastern Shore are within easy reach. Discover the wonderful combination of comfort, flexibility, natural beauty, and community at 7311 Madaline Avenue—a delightful place to enjoy your next chapter of Eastern Shore living.

7311 Madaline Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$199,900

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

406 Dominion Rd, Chester

Listing courtesy of Sell Your Home Services. Contact:

$1,650,000

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

5 Beds ⋅ 4 Baths

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

312 Greenwood Point Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

$280,000

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

2 Beds ⋅ 2 Baths

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

411 Merganser Ct, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$679,990

Welcome to the Franklin, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3.5 baths, and a 2.5-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with a walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

3 Beds ⋅ 4 Baths

Welcome to the Franklin, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3.5 baths, and a 2.5-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with a walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

29488 Mason Ln, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$396,900

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

1837 Harbor, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$589,900

Welcome to 305 N Brook Drive, where beautiful upgrades, thoughtful details, and a premium wooded setting come together in one of North Brook's most desirable locations! Situated on just under half an acre and backing to the woods, this exceptional home offers the perfect combination of privacy, space, and elevated living. Step inside to discover rich chocolate-toned, 5¼-inch wide plank engineered hardwood flooring throughout the main level, custom moldings, plantation shutters, and upgraded lighting and fixtures. The stunning white kitchen features premium Cambria quartz countertops, a subway tile backsplash, and stylish finishes that bring both elegance and functionality to the heart of the home. Upstairs, you'll find three spacious bedrooms, including a beautiful primary suite featuring a walk-in closet and double sink vanity. The outdoor living space is equally impressive! Enjoy relaxing evenings on the expansive 600 sqft paver patio featuring a gas fire pit. The fenced in yard, peaceful wooded backdrop, and storage shed add even more to this incredible property. The fully finished basement, completed in 2024, offers additional living space, a fourth bedroom, a full bathroom with a walk-in shower, and extra storage. A whole home water softener was also installed, providing added comfort and convenience. With its premium lot, extensive upgrades, and incredible indoor and outdoor living spaces, 305 N Brook Drive truly stands apart. Opportunities like this in North Brook don't come along often. Come experience everything this beautiful home has to offer!