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$400,000
3 Beds ⋅ 2 Baths
This is not your average rancher! Welcome to 119-A Rebel Road in Grasonville, featuring a hard-to-find detached two-car garage with A/C and room for a woodstove. This renovated 3-bedroom, 2-bath home sits on nearly half an acre with space for boat storage. PICTURES COMING SOON! Enjoy a huge eat-in kitchen with brand-new stainless appliances, XL sink, new fixtures, lighting and flooring. Fresh paint, new carpet, upgraded baths, and an owner’s suite with private bath and walk-in closet. Peaceful rural setting near waterfront parks, beaches, trails, kayaking, boating, restaurants and shopping.

119-A Rebel Rd, Grasonville

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$435,000
3 Beds ⋅ 1 Baths
Beautifully renovated and move-in ready in the heart of Stevensville! This 3-bedroom, 1-bath rancher has been thoughtfully updated throughout, featuring brand-new LVP flooring, a completely renovated kitchen, updated bathroom, new fixtures, fresh paint, and modern finishes throughout. Enjoy the convenience of being just blocks from downtown Stevensville, with local shops, restaurants, schools, and parks nearby. The Cross Island Trail is just a short walk around the corner, offering miles of paved walking and biking trails across Kent Island, while the Chesapeake Bay Bridge is just minutes away for an easy commute to the western shore. Served by public water and sewer, this beautifully updated home combines modern finishes with a convenient Kent Island location. Nothing left to do but move in and enjoy!

126 State St, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,450,000
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
$920,000
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:

$415,000
3 Beds ⋅ 2 Baths
Grasonville - Property is zoned GVC, this gives you opportunity to own your own home and business. Well maintained property and home located on a corner lot with garage and extra storage sheds. Plenty of room for parking, open floor plan featuring 3 bedrooms 2 baths with luxury vinyl flooring with wonderful kitchen with upgraded commercial size refrigerator/freezer. The decks make it nice for outside entertaining with custom retractable awning and screen/shades.

101 King Store Rd, Grasonville

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

$512,000
3 Beds ⋅ 2 Baths
Welcome to 224 Wye Knot Court, a charming 3-bedroom, 2-bath home situated on a spacious lot in the peaceful Wye Knot Farms community. Step inside to a bright and inviting layout filled with natural light and comfortable, functional living spaces. This well-maintained home offers the perfect opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore. Wye Knot Farms is known for its quiet setting, generous lots, and welcoming neighborhood feel, while still providing convenient access to Route 50, shopping, dining, and the beautiful Wye River. Whether you’re purchasing your first home, looking to downsize, or simply searching for a little more space and tranquility, 224 Wye Knot Court is a must-see! Professional photographs coming soon!

224 Wye Knot Ct, Queenstown

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

$1,025,000
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:

$1,150,000
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
$1,675,000
3 Beds ⋅ 4 Baths
105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer lighting that is included in the sale. A bar and billiards room has custom cabinetry, a pool table and seating area with fireplace, and views of Eastern Bay. Also on this floor is a formal living room with fireplace, a home office with Bay views, and a large mud-laundry room with adjoining powder room. The large primary suite has 3 closets in the bedroom area as well as a walk in closet and dressing room with custom cabinetry and natural light. The large primary bath has custom cabinetry with lots of storage, a separate tub and shower, dual sinks, limestone floors and a separate water closet. The second floor loft opens to two more bedrooms and a shared bath. One of the bedrooms leads to a veranda with stone fireplace and sweeping views of Eastern Bay. Appliances include a Miele refrigerator and freezer, Viking gas range, dishwasher, microwave, warming drawer, beverage and wine coolers, washer and dryer, garage refrigerator and beverage station and a Napoleon outdoor grill. Televisions and sound bars located in the bar area, club room, second floor loft and kitchen are included in the sale. The garage includes two Lift Master garage door openers, two SunPro motorized screens and RaceDeck flooring. Cove Creek Club is situated on 334 acres of large home sites with beautiful landscaping and views of Eastern Bay. Amenities include a USGA rated golf course, a private marina with direct access to Eastern Bay, boat ramp and storage yard, a private sandy beach, tennis, basketball and bocce ball courts, a club house and event facility, pro shop, walking and biking trails, and an exercise facility. It is conveniently located to Annapolis, Baltimore, Washington DC and Philadelphia.

105 Night Heron Ct, Stevensville

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

$862,750
3 Beds ⋅ 2 Baths
THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478
$414,989
3 Beds ⋅ 3 Baths
NEW PRICE—NEW OPPORTUNITY IN ELLENDALE! Tucked away in the back of the community overlooking the peaceful pastures of Kent Manor Inn and the community pond, this beautifully maintained townhome offers low-maintenance Kent Island living in a premium location. The open floor plan features 9’ ceilings, abundant natural light and a two-car garage. Upstairs are two spacious bedrooms, while the finished lower-level flex space is perfect for a home office, gym, media room or guest space. Fresh paint and a newer roof make this home move-in ready! Enjoy community amenities including an outdoor pool, clubhouse, playground, fishing pier with floating dock, walking trails and boat storage. Less than a mile to Route 50 and the Bay Bridge, with shopping, dining and marinas just minutes away. Vacant and available for a quick settlement—come enjoy the Kent Island lifestyle!

111 Ryan Dorsey Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$725,000
5 Beds ⋅ 4 Baths
Nestled on a private peninsula jutting into the tranquil waters of the Wye Mills lake, 132 Denny Lake Road in Wye Mills, MD, is a breathtaking Dutch Colonial gem. Boasting over 3000 square feet of living space, with a fully finished walk-out basement adding a fourth bedroom and two and a half baths in total, this home offers spectacular lake views from every level. Outside, the bulk headed shoreline was completed within the last 30 years, ensuring stability and charm. Perfectly situated for both tranquility and convenience, this home is centrally located—just 15 minutes to Kent Island or Centreville and only a short drive to Easton. Whether commuting to Annapolis (approx. 30 min) or exploring the Eastern Shore, you’ll find every destination within easy reach—making this the ideal blend of serenity and accessibility. A standout feature is the large detached garage with a workshop and a one-bedroom apartment above, complete with a deck overlooking the water—an idyllic retreat. And with its rare Village Commercial zoning, this property is a standout—offering a special mixed-use designation from Queen Anne’s County. It’s ideal for a home-based business, an Airbnb, or other commercial ventures—a truly one-of-a-kind opportunity to live, work, and play in this iconic setting. Cedar roof is about 20 years old w/ a typical life expectance of 40 years. Well and septic were installed in the late 2000's

132 Denny Lake Rd, Wye Mills

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$524,999
2 Beds ⋅ 3 Baths
NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITH ACCEPTABLE OFFER! Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows like new, offering over 2,000 square feet of single-level living in the highly sought-after Four Seasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of direct outdoor patio access and beautiful views from every window. The thoughtfully designed open-concept features two spacious bedrooms, each boasting a full bath and walk-in closet, plus direct patio access from the primary suite. The gourmet kitchen centers around a massive seating island with pendant lighting and a stylish dry bar. French doors open to a dedicated home office, while double sliding doors in the living room provide the entire space with natural light. Quartz countertops and seamless luxury vinyl plank flooring are found throughout the home. Complete with a private guest powder room, laundry room, climate-controlled storage, a one-car garage, and a beautifully appointed community room on the second floor, this condo delivers the low-maintenance lifestyle the community is known for. The award-winning 24,000 square foot Chester House clubhouse is the heart of the community, with indoor and outdoor pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom. Outside, enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and miles of walking and biking trails connecting to the Cross Island Trail. The 450-foot community pier on the Chester River, with boat slips plus canoe and kayak launch and storage, is a favorite for anyone who loves the water. Year-round clubs, classes, live entertainment and events can be found at the community clubhouse, and you’ll be minutes from Kent Island, shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for Annapolis, Baltimore, and Washington D.C. Schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$525,000
5 Beds ⋅ 3 Baths
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$1,400,000
5 Beds ⋅ 4 Baths
Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to create an exceptional waterfront retreat. Offering over 3,500 square feet of living space, this custom-built home is perfectly positioned to capture endless water views from nearly every room. High ceilings and expansive windows fill the home with natural light while framing the ever-changing waterfront backdrop. Designed for both everyday living and effortless entertaining, the main level features an open floor plan that seamlessly connects the living, dining, and kitchen spaces. The gourmet kitchen is equipped with gas cooking, abundant cabinetry, and generous workspace, allowing you to prepare meals while enjoying stunning views of the water. With five bedrooms and three-and-a-half baths, there is plenty of room for family and guests. Thoughtful design elements throughout the home maximize both functionality and comfort while keeping the focus on the incredible waterfront setting. Step outside and discover a boater's dream. The private pier is equipped with electric, water, three boat lifts, including a 20,000-pound lift, 10,000-pound lift, and 2,500-pound lift, offering exceptional flexibility for multiple vessels and watercraft. Spend your days on the water and return home to breathtaking sunsets over the Chester. Additional features include a NEW roof, 2 - 1 year old HVAC systems, tankless hot water heater, attached two-car garage with excellent storage, 50 amp RV hook up, and the quality craftsmanship expected in a custom-built waterfront residence. Whether you're searching for a year-round residence or the ultimate waterfront getaway, 952 Chester Beach Road offers a rare opportunity to enjoy unmatched views, premier boating access, and the relaxed lifestyle that makes Maryland's Eastern Shore so special.

952 Chester River Dr, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,275,000
4 Beds ⋅ 3 Baths
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:

$510,000
3 Beds ⋅ 2 Baths
Welcome to 103 Opera Court in the sought-after, active 55+ community of Symphony Village at Centerville. This expanded Vivaldi model features three bedrooms and two full bathrooms on an oversized corner lot across from parklands and with no home behind the paver patio. Pull up to your side loading garage and take the short path to the front door, with a quaint covered porch for slow evenings and watching nature go by. Once inside, the spacious foyer offers a dry bar with mini-fridge and architectural pillars lead to an open concept living space. You’re invited in by unobstructed views from the dining area through the living area into the family room extension with a vaulted ceiling and fireplace with marble surround. There is beautiful, engineered hardwood flooring throughout the public spaces. Unmatched natural light drenches the entire space which centers on the cozy gas fireplace for ease of use on the few chilly winter nights. The gourmet, open style kitchen features gorgeous cabinetry, granite countertops, stainless steel appliances, including double wall ovens that are sure to please any chef. The primary bedroom suite has brand new carpeting, a sitting area with vaulted ceiling, a tray ceiling above the bed for added drama, and double walk-in closets. The primary bath features separate vanities, a jetted soaking tub and a custom, walk-in tub. The second bedroom is down the hall from the entry and is adjacent to the second well-appointed full bath. The third bedroom, at the front of the home, is a perfect flex space and could be a bedroom, office, or studio. It also has wood floors and plenty of natural light. Tucked away at the center of the home is the laundry which is on the way to the two-car garage. The garage features a “sky basement” above, which is partially finished and can be used for storage. Outside the French doors in the family room is a paver patio, perfect for entertaining, dining alfresco or taking your morning coffee. For peace of mind and low utilities, this home also has solar panels and a whole house generator. The community takes care of the grounds, leaving you more time to relax and enjoy the peace and quiet and the many amenities! There are paths for walking or biking, including one leading to the local shopping center, pickleball and tennis courts, putting green, bocce ball courts and a resort style outdoor pool. The clubhouse features a concert hall, billiards room, fitness room, bar, party rooms, dining room, and an indoor heated pool open every day. Activities include classes to learn a variety of skills, social hour, arts and crafts, game and card nights, an artist guild with quarterly art shows and much more for the low HOA fee. The historic and charming town of Centerville is minutes away with wonderful restaurants and shops, and a wharf for boating, paddling or a picnic. Enjoy the slower pace of the eastern shore while remaining close to the ocean beaches and the city life across the Chesapeake Bay. This home has SO MANY UPGRADES and beautiful views – it’s a very special property.

103 Opera Ct, Centreville

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

$375,000
3 Beds ⋅ 2 Baths
Opportunity meets location at this charming 1891 farmhouse situated on a spacious ¾-acre lot just a few short miles off 301 . Located within the Village Center District, this unique property offers the flexibility and visibility that entrepreneurs, tradespeople, hobbyists, and investors have been searching for. And NO TOWN TAXES. The home features 3 bedrooms and 2 full baths, blending historic character with thoughtful updates including granite countertops and stainless steel appliances. Outside, the standout feature is the impressive 32' x 24' detached garage with two 10' x 10' doors, providing ample space for a workshop, storage, equipment, vehicles, or business operations. Whether you're looking for a place to call home, a property with room to grow your business, or a combination of both, the possibilities here are hard to find. Enjoy the convenience of being just minutes from downtown Centreville, schools, shopping, dining, and major commuter routes while maintaining the space and flexibility that only a property like this can provide. Bring your vision and explore the potential of this rare Village Center opportunity. Buyers to complete their own due diligence for permitted use of the property and fees.

1645 Ruthsburg Rd, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810
$850,000
4 Beds ⋅ 3 Baths
Nestled within the serene enclave of Goose Point Estates, this exquisite one level living home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This residence boasts a modern aesthetic while retaining its timeless charm. Step inside to discover a spacious 2,141 square feet of meticulously designed living space. The interior features a warm palette complemented by rich hardwood flooring and plush carpeting, creating an inviting atmosphere throughout. Crown moldings and chair railings add a touch of elegance, while recessed lighting and skylights bathe the space in natural light. The heart of the home is undoubtedly the gourmet kitchen, equipped with upgraded countertops and ample table space for casual dining. High-end appliances, including a self-cleaning oven, built-in microwave, and energy-efficient dishwasher, make cooking a delight. The adjacent family room, complete with a charming wood-burning fireplace, provides a perfect retreat for relaxation. This residence features four generously sized bedrooms, including a main-level bedroom for convenience. The luxurious master suite offers a walk-in closet and a spa-like bathroom with a stall shower included with a hot tub, ensuring a private oasis for unwinding after a long day. Outside, the property is equally impressive, set on a sprawling 2.4-acre lot surrounded by lush trees and serene woods, providing a tranquil backdrop for outdoor living. Enjoy evenings under the stars in the hot tub or host gatherings with friends in the beautifully landscaped yard. The exterior is adorned with thoughtful features such as bump-outs, exterior lighting, and flood lights, enhancing both functionality and aesthetics. Additional highlights include a spacious attached garage with extra storage, main-floor laundry for added convenience, and a water treatment system for peace of mind. This home is not just a residence; it's a lifestyle choice, offering a perfect blend of luxury, comfort, and nature. Experience the best of both worlds in this exceptional property, where modern amenities meet the tranquility of nature, creating a perfect sanctuary to call home. Roof is 10 years old. Goose Point Estates is just minutes away from route 50 and the Chesapeake Bay Bridge but far enough away from all the traffic.

121 Eareckson Ln, Stevensville

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

$595,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$598,500
4 Beds ⋅ 3 Baths
**Price Improvement** OVER 5 ACRES. NO HOA. JUST MINUTES FROM US301. That’s a combination that’s becoming increasingly difficult to find. Welcome to 913 Clark Corners Rd, where 5.42 ACRES of partially wooded land offer the freedom to live your way! Whether you’re dreaming of horses, chickens, gardening, recreational activities, frequent sightings of deer, birds, owls, and other wildlife, or simply room to breathe, this property delivers the space and flexibility today’s buyers are searching for. Inside, you’ll find a thoughtfully updated home featuring a fully renovated kitchen with quartz countertops, 42” soft-close white cabinetry, stainless steel appliances, recessed lighting, a large center island with seating, and luxury vinyl plank flooring that flows seamlessly into the spacious family room with a gas fireplace. The main level also boasts engineered hardwood floors and offers formal living and dining rooms, an updated powder room, and a renovated laundry/mud room with additional cabinetry, countertop workspace, and valuable pantry storage. Upstairs, the spacious primary suite includes a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide room for family, guests, hobbies, or a home office. Outside, enjoy a welcoming wraparound front porch that’s perfect for relaxing and taking in the peaceful surroundings, along with a rear deck, partially fenced backyard, large storage shed, mature landscaping, permanent Govee front exterior lighting, and a blend of open yard and wooded acreage that creates a setting rarely found at this price point. Above the garage, the unfinished attic space provides exceptional storage and potential future possibilities, subject to buyer verification of county requirements and approvals. Whether you’re looking for room to grow, room to roam, or simply room to breathe, this property delivers. To make this opportunity even more appealing, sellers are offering a 2-YEAR HOME WARRANTY (up to $2,000) with an acceptable offer—adding extra peace of mind to a property that already offers space, flexibility, and freedom.

913 Clark Corners Rd, Centreville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$575,000
4 Beds ⋅ 3 Baths
Motivated Seller!! Spanning nearly 2,800 sq. ft., this Colonial style home is perfectly nestled on a private 1 acre corner lot in the highly desirable community of Lently Farms. Framed by mature shade trees and beautiful lush landscaping, this property offers peace, privacy, and plenty of outdoor space to enjoy. Relax or entertain on the hardscaped rear patio, perfect for grilling and soaking up the sun and appreciate the convenience of the double entrance paved driveway. Step inside to a welcoming foyer that leads to a spacious main level, featuring a kitchen with breakfast nook and coffee/bar station, adjoining family room with a custom raised hearth wood-burning fireplace, and easy access to the bright four season room. The first floor also offers a formal living room and dining room, private office with separate entrance, laundry/mudroom with utility sink and storage cabinets and a half bath. Upstairs you’ll find four generously sized bedrooms, including a primary suite with walk-in closet and private bath featuring a double vanity. An additional full guest bath includes a tiled shower and double vanity. Don’t miss the versatile bonus space above the garage, ideal for a hobby room, studio, or additional storage. A spacious 2-car insulated garage completes the home. With some updates and your own personal touches, this home could easily become the home you’ve been searching for. Conveniently located just minutes from historic Centreville, a charming waterfront town known for its courthouse square and town wharf. Enjoy quick access to MD Route 301, the Chesapeake Bay Bridge, outlet shopping, waterfront restaurants, marinas, and an easy commute to Easton, Annapolis, and the MD/DE beaches. Experience all the Eastern Shore has to offer—fishing, crabbing, parks, bike and walking trails, farmers markets and so much more!

122 Lently Farm Ln, Centreville

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183
$549,900
3 Beds ⋅ 2 Baths
Symphony Village a premier 55 plus active adult community which is well desired and nicely located just on the edge of Centreville. If you are looking for the perfect 55 plus community this is it! Active adults loving life and enjoying the community this neighborhood provides from Happy Hours, Pools, events, pickleball, the gym and more. You will always see neighbors walking, riding bikes and enjoying life in the Village! This home is one of the few which gives you privacy out back backing to the woods offering you complete peace. Relax on your back patio and watch the wildlife, listen to the birds, drink your coffee, grill or have nice gatherings with your friends. This amazing and well kept home is ready for a new owner and you will not be disappointed! Offering 3 nice sized bedrooms an d2 full bathrooms with a nice open concept this floor plan allows you the option to set it up how you choose. Offering a ton of natural lighting with all of the windows this home exudes fresh and airy feelings. The kitchen has a ton of cabinets perfect for the person who loves to cook and plenty of space for your kitchen table. You will enjoy the gas fireplace all winter long as it is a great feature. The garage offers 2 parking spaces and a huge room above the garage with ample storage. This neighborhood's HOA includes lawn care, trash, snow removal, and the FANTASTIC Club house! Come and take a look and see why everyone loves Symphony Village! You will want to live here too!

126 Encore Ct, Centreville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$4,700,000
6 Beds ⋅ 6 Baths
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

200 Wye Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$699,000
4 Beds ⋅ 3 Baths
Highly motived sellers enjoyed Prospect Bay and want you to as well--they just reduced again making it super attractive. Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$529,000
4 Beds ⋅ 4 Baths
NEW PRICE ....Welcome to 142 Harmony and this beautiful Beethoven model home featuring 4 bedrooms and 3 and one half bath. Situated on a lot that is just a short walk to the community club house, pools and all amenities, this home is designed with a beautiful brick front. As you enter, the floor inviting floor plan welcomes you with the living and dining area on the front of the home and stairs to the side to the upper level. Moving through you'll enter the very large family room with fireplace and the oversized gourmet kitchen with additional cabinets. The breakfast area off of the kitchen allows for relaxing views of the rear patio. The master suite is also located on the main level with master bath featuring a walk-in shower and a walk-in jetted tub. This suite also has two walk-in closets and additional stairs to the upper level. To complete the main level of the home is a half bath and laundry room with access to the garage which includes a sky basement for storage above. The second level of the home offers a very large additional area that can be utilized in many ways along with a carpeted walk-in storage area that can be utilized as a closet or utility room. To complete the upper level is a sitting room overlooking the family room below along with another bedroom and full bath. This home is move in ready and available for a quick settlement.

142 Harmony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$675,000
3 Beds ⋅ 5 Baths
Open House July 21, 2026, 4 PM to 7 PM. Welcome to 371 Overture Way, nestled in the serene 55+ active adult community of Symphony Village in Centreville, where comfort, convenience, and connection come together beautifully. This thoughtfully maintained home offers over 6,000 square feet of living and storage space, featuring 3 spacious bedrooms, 4 full baths, and 1 half bath, along with a new roof installed in 2023 for added peace of mind. The attached two-car garage includes a durable epoxy-coated floor and stairs to generous overhead storage, perfect for keeping everything organized without sacrificing living space. Designed with ease and everyday enjoyment in mind, the bright, open main level showcases a gourmet kitchen with extended granite countertops, stainless steel appliances, and a Jenn Air gas stove, ideal for both casual meals and entertaining. The adjoining breakfast nook provides ample cabinetry and prep space, while the flowing layout includes hardwood floors, custom plantation shutters, and inviting living and dining areas. A sun-filled sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious deck, perfect for relaxing or hosting guests while enjoying the private wooded backdrop. The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower, offering comfort and convenience all in one space. Upstairs, a versatile loft provides the perfect setting for a sitting area or home office, along with a guest bedroom complete with its own full bath and walk-in closet - ideal for visiting family and friends. The fully finished lower level expands your living space even further, with a family room featuring a fireplace, room for a game table, and a walkout to a beautifully paved patio. Two additional bonus rooms, a full bath, and an oversized storage area with a workbench, refrigerator, and freezer make this level both functional and flexible. Life in Symphony Village means more than just a beautiful home, it's a vibrant, welcoming community. Residents enjoy access to a clubhouse with social spaces, indoor and outdoor pools, a fitness center, pickleball and bocce courts, walking and hiking trails, and a full calendar of activities designed to keep you as active and engaged as you would like to be. Conveniently located near Queenstown Premium Outlets and the charming downtown area of Centreville, you will also find yourself just a short drive from the waterfront towns of Chestertown, Easton, St. Michaels, and Annapolis. This is more than a home, it is a lifestyle designed for comfort, connection, and ease. Come experience all that 371 Overture Way has to offer!

371 Overture Way, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,325,000
4 Beds ⋅ 5 Baths
BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR GARAGE AND A MONSTROUS DETACHED GARAGE WITH ROOM FOR 6 MORE CARS. PLENTY OF STORAGE. BEAUTIFUL, PRIVATE INGROUND GUNITE POOL. CALL LISTING AGENT FOR MANY MORE AMENITIES. READ HOA DOCS IN DISCLOSURES. TRY TO GIVE 1-2 DAYS SHOWING NOTICE, PLEASE.

105 Port Ct, Grasonville

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690