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252 Harbor Ln, Queenstown
$749,000
4 Beds ⋅ 3 Baths
PRICE REDUCTION!! Discover the charm of Queenstown, where neighbors know your name and community is more than a word - it's a way of life! Enjoy a lifestyle filled with small town local traditions and nearby community events. Welcome to a VERY well-maintained 4 bedroom, 2.5 bathroom home located in the coveted Queenstown Harbor waterfront community. This beautiful waterfront home features a main-level primary suite with hardwood floors and a private en-suite bath, plus 3 additional bedrooms on the upper level. The Gourmet chef's kitchen is equipped with stainless steel appliances, marble countertops, and opens to comfortable living spaces ideal for entertaining. Enjoy the front-row seat to nature and the water in the outdoor three-season covered porch and a patio featuring newer composite decking. This offers ultimate backyard privacy! The property is surrounded by mature landscaping and low-maintenance river rock along the perimeter of the home. Launch your kayak or paddle board right behind your home with boat slips available in the community. IDEALLY located next to Queenstown Harbor Golf Course, featuring the new Toptracer partially heated driving range and the recently renovated Tavern restaurant. Convenient access to Route 50 makes commuting to Annapolis, Washington DC, and the beaches a breeze! Here, life moves at just the right pace - relaxed, welcoming, and connected. Come see why Queenstown is more than a place to live; it's a place to belong! LOW HOA FEE OF $43/MONTH COMMUNITY OWNED AND OPERATED MARINA! BOAT SLIPS AVAILABLE! $650 YEARLY FOR INSIDE SLIP AND $785 YEARLY FOR OUTSIDE SLIP!

252 Harbor Ln, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

524 Church Hill Rd, Centreville
$699,900
5 Beds ⋅ 5 Baths
This stunning Victorian home, built in 1911, exudes timeless charm and modern comfort. With 5 spacious bedrooms and 3 full bathrooms, this residence offers a perfect blend of classic craftsmanship and contemporary design. The heart of the home features a gourmet kitchen with upgraded countertops, a built-in range, and a cozy breakfast area, ideal for gatherings. Elegant details like chair railings, built-ins, and hardwood floors enhance the inviting atmosphere throughout. The home's unique architectural features include a double staircase that adds a touch of drama and elegance, leading to the upper levels where the primary suite awaits. Step outside to enjoy the expansive 1.56-acre lot, complete with beautifully crafted stone retaining walls and a personal in-ground pool, perfect for summer relaxation. The expansive wrap-around porch and screened patio provide serene outdoor spaces for entertaining or unwinding. The fully finished basement includes a workshop area and convenient access to the outdoors. This home is designed for both functionality and style, making it a true sanctuary for those seeking comfort and elegance. This captivating property is conveniently located a short walk to historic downtown Centreville yet combines serene privacy with easy access to area dining and shopping.

524 Church Hill Rd, Centreville

Listing courtesy of Century 21 Downtown. Contact:

403 Chesterfield Ave, Centreville
$699,000
4 Beds ⋅ 4 Baths
Step into a piece of Centreville's history with this distinctive Victorian, originally built in 1875, where timeless architectural charm meets thoughtful modern updates! Situated on approximately half an acre in the heart of town, this one-of-a-kind property welcomes you with a massive wraparound front porch and charming porch swing, the perfect place to relax and take in the beauty of your surroundings. Inside, you'll find impressive 10-foot ceilings on the main level, classic built-ins, beautiful wood floors, and character-filled spaces that reflect the home's historic roots. Offering 4 bedrooms, 3 full baths, and 1 half bath, plus a massive bonus room with the potential for a 5th bedroom, there is plenty of space to accommodate a variety of needs and lifestyles. This home blends its historic character with extensive improvements made over the years. The galley kitchen was fully renovated in 2024 with new cabinetry, countertops, flooring, and appliances, including a gas range, followed by a substantial kitchen expansion in 2025 that added a 12x12 breakfast nook, additional cabinetry and countertops, a second sink and refrigerator, and a wine cooler. A full bathroom on the main level was also part of the expansion, including tile flooring & radiant floor heat. Additionally, the primary bathroom on the second floor was renovated with a full-size tiled shower, new vanity, and toilet, with additional bathroom upgrades enhancing the secondary bathroom as well. Important system updates include a new high-efficiency furnace/boiler, mini-split systems serving all three second-floor bedrooms and the primary bathroom, removal of the original knob-and-tube wiring, a metal chimney liner, and replacement of the second-floor windows. The chimneys have been converted to gas logs, offering the ambiance of a fire with added convenience, while still keeping the character of the stunning fireplaces. Additional improvements include refinished wood floors, updated third-floor flooring and carpeting, and numerous other enhancements. A full list of improvements is available. Step outside and discover an enchanting setting with extensive, lush landscaping reminiscent of finding yourself strolling through a peaceful English garden, creating a beautiful backdrop for relaxing and entertaining. The fully fenced in-ground concrete, saltwater pool, less than four years old, provides a wonderful place to enjoy warm summer days, while the hardscape walkway connects the outdoor spaces. A distinctive carriage house, originally dating to 1906 and thoughtfully modified with a more modern feel, adds even more character and versatility. Featuring two garage doors with openers and a wide staircase leading to the second floor, this separate structure offers valuable garage and additional space. And the location? It's hard to beat! Enjoy a short walk to the Wharf, Doc's, and the heart of downtown Centreville, where local destinations and small-town charm are right outside your door. Historic character, extensive updates, enchanting gardens, a new pool, and a unique carriage house come together to create a truly special Eastern Shore property unlike anything else on the market!

403 Chesterfield Ave, Centreville

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

407 Five Farms Dr, Stevensville
$699,000
4 Beds ⋅ 3 Baths
KENT ISLAND LIVING, UPGRADED. Welcome to Queen Anne Colony, where coastal lifestyle meets a home that has already had the big-ticket work DONE. Offering over 2,100 sq ft, a private pool, beautifully renovated interior, and access to a community marina, this is the kind of home that lets you move in and immediately start enjoying everything Kent Island has to offer. Inside, the showstopper is the fully renovated kitchen featuring gorgeous quartz countertops, abundant cabinetry, and a layout made for entertaining. Hardwood floors bring warmth and character throughout, while updated bathrooms and TWO fireplaces create a home that feels both elevated and inviting. And the upgrades go far beyond what you can see. A new roof (2023), siding (2026), garage door (2025), water heater and water softener (2024), HVAC (2018), brand-new washer and dryer (2026), pool liner (2021), and an encapsulated crawlspace mean many of the expensive projects buyers worry about have already been handled. Outside, your own private backyard retreat is waiting. Spend summer days by the pool, entertain friends, or simply unwind after a day on the water. Then there’s Queen Anne Colony itself. With a community marina offering convenient boating access and a community park, you’re not simply buying a home—you’re buying into the Kent Island lifestyle. Renovated. Upgraded. Pool. Marina access. Kent Island. This one checks the boxes buyers are looking for, and it’s ready for its next owner.

407 Five Farms Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

120 Pathfinder Cir, Grasonville
$659,950
4 Beds ⋅ 4 Baths
Welcome home to 120 Pathfinder Circle in Perry's Retreat! Built in 2023 and meticulously maintained, this 4 -bedroom , 3.5 bath home offers approximately 3,010 sf of beautify designed living space, where thoughtful upgrades,custom touches,and everyday functionality come together. From the moment you walk in, the attention to detail is impossible to miss. The main level showcases a stunning three-sided fireplace topped with a custom walnut mantel - an eye catching centerpiece that makes the living space feel warm, inviting, and distinctly your own. The kitchen is made for gathering, cooking and entertaining, featuring two ovens and custom -made pendant lighting that adds both function and personality. Throughout the home, an upgraded Craftsman trim package recessed lighting , luxury vinyl plank flooring, and ceiling fans in every room create a polished, comfortable feel. With Ethernet wiring throughout , this home is ready for everything from work from home days to movie nights and streaming marathons. Upstairs, the spacious primary suite feels like a retreat, complete with two walk in closets and a generous shower with dual showerheads. A secondary bedroom with its own ensuite bath offers a private space for guests or family. Two additional flex spaces give you the freedom to create dedicated offices, home gym, playroom or whatever your lifestyle demands. A separate loft adds even additional room to spread out. The back yard is where this property really shines. The 16x40 patio provides an incredible outdoor living and entertaining space, while the privacy fence creates a comfortable, secluded setting. The meticulously maintained landscaping and lush lawn are true standouts and add exceptional curb appeal. With a three car garage, there's plenty of room for vehicles and storage. This is more than a newer home - it's a home that has been thoughtfully enhanced and lovingly maintained. The custom details and flexible spaces truly make it feel special. Come see why 120 Pathfinder Circle is the home you have been looking for.

120 Pathfinder Cir, Grasonville

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

1351 Calvert Rd, Chester
$645,000
6 Beds ⋅ 3 Baths
A rare financing opportunity: qualified buyers may be able to assume the seller’s existing loan at an interest rate of approximately 3%, and VA eligibility is not required. From the welcoming front porch overlooking the bay to the spacious backyard with two storage sheds, this home offers room to live, work and unwind. The kitchen features stainless steel appliances and granite countertops with abundant workspace, making it ideal for everyday living and entertaining. Upstairs, the primary suite feels like a true retreat with a separate sitting area, walk-in closets, dual vanities and an impressive oversized shower. A flexible water-view room on the main level provides the perfect setting for a home office or sixth bedroom. The paved driveway leads to an expansive garage with exceptional storage and workshop space, along with a 30-amp hookup for RV or boat shore power that can also accommodate EV charging. Located on beautiful Kent Island, Marling Farms is an amenity-rich waterfront community offering four beaches, a pavilion, community docks, playground and swing areas, a baseball field and a basketball court.

1351 Calvert Rd, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

118 Broadwater Dr, Chester
$645,000
2 Beds ⋅ 2 Baths
Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult neighborhoods. Designed with both elegance and everyday comfort in mind, this home features a stunning Gourmet Kitchen highlighted by a large Quartz Island, premium Gourmet Appliance Package with Double Oven, and abundant workspace—perfect for everything from casual breakfasts to holiday entertaining. The open-concept Great Room creates an inviting gathering place, centered around a warm Gas Fireplace, while upgraded lighting throughout the home adds a sophisticated touch. The Luxury Spa Bath offers a private retreat after a busy day, and Quartz vanities in every bathroom provide both beauty and durability. The thoughtfully designed floor plan includes first-floor bedrooms, allowing comfortable one-level living. A dedicated home office on the main level provides an ideal workspace, hobby room, or can easily function as a third bedroom for visiting family and friends. Additional premium features include elegant Plantation Shutters, an oversized two-car garage with generous storage space, and an underground irrigation system that helps keep your lawn lush while minimizing maintenance. With approximately $89,000 in builder upgrades and options, this home offers exceptional quality and value that would be costly to duplicate today. Come experience the carefree lifestyle of Four Seasons at Kent Island, where resort-style amenities, beautiful surroundings, and a vibrant social atmosphere make every day feel like a vacation. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle.

118 Broadwater Dr, Chester

Listing courtesy of RE/MAX Executive. Contact:

144 Wye Knot Rd, Queenstown
$634,900
4 Beds ⋅ 3 Baths
**WE HAVE A KICK OUT CLAUSE** Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

144 Wye Knot Rd, Queenstown

Listing courtesy of RE/MAX Leading Edge. Contact:

102 Boatswain Way Unit 2911, Chester
$619,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. 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.

102 Boatswain Way Unit 2911, Chester

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

242 Perrys Retreat Blvd, Grasonville
$619,900
4 Beds ⋅ 3 Baths
Discover the perfect blend of modern elegance and comfort in this stunning Colonial-style home located in the desirable Perry's Retreat. Built in 2024, this residence boasts a pristine condition and an array of features designed to enhance your lifestyle. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen, dining area, and family room, creating an ideal space for entertaining and everyday living. The kitchen is a chef's dream, equipped with upgraded countertops, a double oven, built-in microwave, and ample pantry space. With four generous bedrooms and 2.5 baths, this home offers plenty of space for relaxation and privacy. The upper floor laundry adds convenience to your daily routine, while the elegant luxury vinyl plank flooring and tasteful window treatments throughout elevate the aesthetic. Outside, the property features a well-maintained exterior with sidewalks and a concrete driveway leading to a two-car attached garage, ensuring ample parking and easy access. The 0.14-acre lot provides a manageable outdoor space for gardening or leisure activities. This home is not just a place to live; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this exquisite property your own!

242 Perrys Retreat Blvd, Grasonville

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

157 Fawn Ln, Grasonville
$619,900
5 Beds ⋅ 3 Baths
New Construction, Ready September, this new home features 4 bedrooms, 2.5 bathrooms, and the builder’s highly sought-after 3rd Floor Sky-Basement. This home combines comfort, style, and versatility. The main level boasts an open floor plan with luxury vinyl plank flooring and crown molding throughout. A flex room off the foyer is ideal for a home office or formal living area. The gourmet kitchen features granite countertops, white shaker cabinets, stainless steel appliances, and a large breakfast bar, seamlessly connecting to a bright and airy sunroom—perfect for casual dining and entertaining. The spacious family room offers a cozy retreat for relaxing evenings. A stylish mudroom with a barn door and built-in bench leads to the attached 2-car garage. Upstairs, the owner’s suite includes a spacious walk-in closet and a spa-inspired bath with double vanities. Three additional bedrooms and a full hall bath offer plenty of room for family or guests. The third-floor Sky-Basement is fully finished with its own HVAC system—ideal for a rec room, gym, media space, or extra storage. Located in a quiet, neighbor-friendly community with convenient access to commuter routes, including US-50, this home is a perfect blend of luxury and accessibility. Sales price reflects builder promotion with the use of a preferred lender and title company. See the sales agent for details. Photos are for illustrative purposes and may show optional features. Home is under construction.

157 Fawn Ln, Grasonville

Listing courtesy of Island Realty, LLC. Contact:

105 Symphony Way, Centreville
$619,000
3 Beds ⋅ 3 Baths
Welcome to 105 Symphony Way in the sought after community of Symphony Village at Centreville. This is a rare find in the community, a Wagner Model located just steps from the community club house. This 3 bedroom 3 full bath home is move in ready and awaiting it's next lucky owner. As you arrive you'll be greeted by the beautiful stone front and welcoming porch on this home. Entering you'll immediately notice the bright and open floorplan and your eyes will be drawn through the home to the gorgeous rear feature wall and fireplace. Proceeding through you'll find a front bedroom/office and full bath. Moving forward the Gourmet Kitchen and island featuring granite counters, stainless appliances, tile backsplash, under cabinet lighting and one of the largest pantries in the community. The large laundry room with new washer and dryer includes interior stairs leading to the finished, heated and cooled sky basement. As you make your way through the home, the main level also includes the oversized master suite, his and her closets, master bath with walk-in shower and split vanity sinks. The extended master suite also allows for entry to the rear screened patio. The open feel of the main living area, dining area and family room makes this home perfect for social gatherings. The second level of the home features a large seating area including a sink, 3rd bedroom and Jack and Jill bathroom. You won't want to miss the rear outdoor living space of this beautiful home. Passing through the screened patio, you'll enter an incredible paver patio along with a Zen garden and multi light water fall and rock garden. Please ask your agent for the full list of upgrades to this property.

105 Symphony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact:

102 Boatswain Way Unit 2912, Chester
$609,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. 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.

102 Boatswain Way Unit 2912, Chester

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

102 Boatswain Way Unit 2912, Chester
$599,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and stylish workspace. The kitchen is designed for everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. 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.

102 Boatswain Way Unit 2912, Chester

Listing courtesy of KOVO Realty. Contact:

371 Overture Way, Centreville
$595,000
3 Beds ⋅ 5 Baths
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:

208 Widgeon Way, Chester
$590,000
3 Beds ⋅ 4 Baths
Direct Marina Views of Castle Harbor Marina * Watch the Boats and Sunsets from your Deck & Balcony * One-of-a-Kind View * END-UNIT with Garage * Nestled in the prestigious Bayside community, this exquisite end-of-row townhouse offers a harmonious blend of contemporary coastal design and luxurious living. With three spacious bedrooms and three and a half elegantly appointed bathrooms, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The heart of the home features upgraded countertops, a generous kitchen island, and an eat-in space, perfect for casual gatherings. The family room, adorned with a cozy gas fireplace framed by glass doors, creates an intimate atmosphere for relaxation. Recessed lighting and ceiling fans enhance the ambiance, while large windows drench the space in natural light, showcasing the beautiful luxury vinyl plank and ceramic tile flooring. Retreat to the primary suite, where a walk-in closet and a spa-like bathroom with a walk-in shower await, offering a private oasis for unwinding after a long day. Additional bedrooms are equally spacious, ensuring comfort for all. The exterior of the property is equally impressive, featuring a wrap-around porch and a balcony that invite you to enjoy the serene surroundings. The community amenities are unparalleled, including a sparkling outdoor pool, tennis and volleyball courts, and a clubhouse that serves as a hub for social gatherings. With meticulously maintained common areas and professional management, the association fee covers everything from lawn care to snow removal, allowing you to enjoy a carefree lifestyle. Situated on a corner lot, this home offers easy access to the Chester River, perfect for those who appreciate water-oriented living. The nearby recreational facilities and common grounds provide ample opportunities for outdoor activities and relaxation. With an attached garage and secure parking, convenience is at your fingertips. Located just minutes from the airport and local attractions, this property embodies the essence of luxury living in a vibrant community. Experience the perfect blend of comfort, style, and convenience in this stunning Bayside townhouse, where every detail has been thoughtfully curated for an exclusive lifestyle.

208 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

7121 Main St, Queenstown
$590,000
4 Beds ⋅ 4 Baths
THE ASSUMABLE 3 1/8% MORTGAGE ON THIS HOUSE WOULD SAVE A BUYER SEVERAL HUNDRED DOLLARS ON EACH MONTHLY MORTGAGE PAYMENT. A historic home made new again! Recent improvements include a brand new HVAC system installed in 2023, a water heater replaced in 2022, a new roof and gutters completed in April 2026, refinished butcher block countertops, freshly painted kitchen cabinets, updated stainless steel appliances, added storm windows for comfort and efficiency, newly added ceiling fans on the covered front veranda, and thoughtful renovations throughout that help blend historic charm with everyday modern living. Steeped in history and full of soul, the historic Queenstown School House, known as Double School House Number 6 and built in 1834, feels less like a house and more like a story carefully carried through generations. Expanded, renovated, and thoughtfully updated over the years, it still holds onto the details that make historic homes unforgettable. Original wavy glass window panes catch the sunlight beautifully while added storm windows help preserve comfort and efficiency. Look closely and you’ll even spot square nails still visible in portions of the flooring, quiet reminders of craftsmanship from another era. Exposed beams, wide plank hardwood floors, brick accents, enchanting natural light, and inviting living spaces give the home a feeling that’s difficult to recreate. Every room seems to catch sunlight differently throughout the day, giving each space its own personality. It’s rare to find a home that blends modern farmhouse comfort, country living, vintage style, and historic schoolhouse character in a way that feels this natural and instantly like home. Just off the kitchen, the dining room creates an easy flow for everyday meals or gatherings with friends and family. Near the front of the home, a cozy study offers the perfect spot for reading or quiet moments, while the family room beside it feels welcoming for game nights and long conversations. The main level also includes two half baths along with a practical laundry and pantry area that helps everyday living stay organized. In the kitchen, refinished butcher block countertops, a farmhouse sink with an unlacquered brass faucet, freshly painted cabinets, stainless steel appliances, and a pellet stove tie everything together beautifully while adding supplemental heat in the kitchen during colder months. Upstairs, you’ll find four bedrooms, two full bathrooms, and a flexible recreation area that can easily become an art studio, hobby room, workout space, reading area, or whatever fits your lifestyle best. Outside, the property unfolds beautifully in every direction. The covered front veranda, complete with a hanging porch swing and newly added ceiling fans, feels like the kind of place where coffee lasts longer and neighbors stop to wave while walking their dogs or heading through town on errands. That’s part of what makes Queenstown feel so special. It’s welcoming, connected, and the kind of small town where people still genuinely know one another. A classic picket fence surrounds the property while the gardens come alive throughout the seasons with raised beds, David Austin roses, mature elderberries, gooseberries, thornless blackberries, hydrangeas, lilacs, evergreen jasmine, and four varieties of peonies that bloom for nearly a month every spring. Just outside the sunroom, a classic English pea gravel gardenscape creates a beautiful outdoor dining area for holidays, celebrations, or evenings under the stars. Located in historic Queenstown, this home is close to Queenstown Pizzeria, Salt Wellness, Queenstown Harbor Golf Course, the town boat ramp, a hidden beach, waterfront dining, outlet shopping, and nearby parks. Nearly two centuries old, it still feels comfortable, loved, and full of life.

7121 Main St, Queenstown

Listing courtesy of EXP Realty, LLC. Contact:

101 Orchestra Pl, Centreville
$589,000
3 Beds ⋅ 3 Baths
Photos coming soon... Welcome to 101 Orchestra Place in Symphony Village at Centreville 55+ Active Adult Community. This beautiful, move in ready Wagner model home is impressive from the moment that you arrive at the home. The stone front on this home is just the beginning of the upgrades on the home. The Wagner is a unique model in the community and you'll be amazed at the open but cozy feeling of the layout. Upgrades in this home include hardwood plank flooring, crown moldings, plantation shutters, granite counters, stainless appliances, gas cooktop, under cabinet lighting, stainless hood, subway tile backsplash, floor to ceiling stone fireplace and much more. As you enter the home, you'll find the front office/bedroom along with a full bath to your right. Just past this area, is the gourmet kitchen with large island and the largest pantry of any model in the community. The oversized laundry room leading to the garage, also features the interior carpeted stairs leading to the fully finished heated and cooled sky basement. The dining and living area off the kitchen leads to the rear screened area and large outdoor paver patio. The master suite with extension and master bath complete the main level of the home. The second level features a oversized sitting area, bedroom and 3rd full bath. Updates on the home include one new HVAC system and a new roof.

101 Orchestra Pl, Centreville

Listing courtesy of RE/MAX Executive. Contact:

129 Wheelhouse Way Unit 11, Chester
$585,000
2 Beds ⋅ 3 Baths
Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

227 Gibson Cir, Chester
$559,900
3 Beds ⋅ 3 Baths
**OPEN HOUSE CANCELLED!!** Under Contract. Come discover Eastern Shore living in the sought-after Waterfront Community of Gibson's Grant! Tucked away on a peaceful cul-de-sac, this charming end-of-row townhouse offers 3 spacious Bedrooms, 2.5 Bathrooms, Office/Den and an inviting blend of comfort and refined style! Stunning Hardwood floors, extensive Crown Moldings and recessed lighting set an elegant tone throughout. The Gourmet Kitchen features upgraded Granite countertops, NEW Stainless Steel Refrigerator, Cooktop, Double Oven, 42"Cabinets and a generous Granite Island... opening seamlessly to the Family Room for effortless entertaining! A Fireplace creates a cozy gathering place, while the Primary Suite provides a private retreat with a walk-in closet and luxurious en-suite Bath. New washer and dryer in the laundry room and brand new carpet in 2 bedrooms and stairs. Two car garage for extra storage and a driveway for off street parking, makes life easier. Outside boasts an extensive brick patio which provides an attractive setting for alfresco dining, grilling and relaxation. The association handles lawn care and maintenance, leaving more time to enjoy Gibson's Grant's exceptional amenities, including a Clubhouse, Pool, Fitness Room, Fishing/Crabbing Pier, Pavilion, Trails, Kayak Storage and Playground! Convenient access to Macum Creek for canoeing and kayaking, plus nearby parks, beaches, boat ramps, boutique shopping, restaurants, outlets and highly regarded schools! This home delivers the ideal combination of water-oriented recreation, low-maintenance living and neighborhood charm!

227 Gibson Cir, Chester

Listing courtesy of RE/MAX Executive. Contact:

201 Larch Pl, Stevensville
$559,000
3 Beds ⋅ 4 Baths
Welcome to 201 Large Place, a unique 3-bedroom home in the desirable Cloverfields community offering exceptional versatility, generous living space, and an incredible outdoor setup. Situated on an oversized corner lot, this property delivers the space, functionality, and flexibility today’s buyers are looking for, both inside and out. Inside, you’ll find generously sized bedrooms, beautifully maintained carpeting, luxury vinyl plank flooring throughout the first floor, and classic hardwood stairs. The kitchen and adjoining dining area flow seamlessly together, creating a welcoming space for everyday living and entertaining. The kitchen also features a convenient pantry and opens through sliding glass doors to an enormous, newly refaced rear deck with durable RDI vinyl railings, providing an outstanding space for outdoor dining, gatherings, and relaxing. The home’s flexible layout offers exciting possibilities for multigenerational living, extended guests, or a home-based business. The primary bedroom suite features ample closet space and a convenient Jack-and-Jill-style full bathroom with custom tile work and a full tiled walk-in shower. The bathroom configuration offers the opportunity to reconfigure the space to create a more traditional private primary suite. An additional full bathroom features a tub-and-shower combination with porcelain tile, while a main-level half bath adds everyday convenience. One of the home’s standout features is the additional first-floor kitchenette and bonus room that is , currently utilized as a daycare, complete with its own full bathroom. This flexible space offers excellent potential for conversion into a first-floor primary suite, guest quarters, or an in-law-style living area with a kitchenette, subject to applicable approvals and modifications. Upstairs, a walk-up staircase leads to a spacious attic with standing-height clearance and abundant storage, along with an additional bonus room offering even more possibilities for hobbies, recreation, or additional flexible use. Step outside and discover a backyard that truly sets this property apart. The fully enclosed yard features six-foot privacy fencing, a massive newly refaced deck, a paver patio and walkways, a fire pit, and outdoor electrical service. A dedicated children’s play area features playground mulch, artificial turf, and its own separate black metal fencing, creating a distinct space for play while keeping it separated from the remainder of the backyard. At the rear of the property, you’ll find an oversized detached garage with approximately 18-foot ceilings, offering exceptional space for vehicles, storage, hobbies, or workshop use. But that’s not all! Adjacent bonus space provides a separate, heated, all-electric retreat with the potential for a man cave, hobby room, recreation area, or private workspace. Its separate structure and unique setup offer a rare opportunity to create a space all your own. Additional features include energy-efficient windows, vinyl siding, a roof replaced within the last 6 years, a convenient side entrance, and paver walk access connecting the rear of the home to the detached garage and bonus space. With four bedrooms, multiple full bathrooms, flexible living arrangements, abundant storage, an oversized detached garage, and an incredible outdoor entertainment area, 201 Large Place offers a combination of space and possibilities that’s hard to find. Whether you’re looking for room to spread out, accommodate extended family, work from home, enjoy your hobbies, or entertain in style, this Cloverfields property deserves a closer look!

201 Larch Pl, Stevensville

Listing courtesy of Samson Properties. Contact:

157 Greenwood Creek Rd, Queenstown
$549,900
3 Beds ⋅ 2 Baths
Price improvement on this beautiful expanded Brick Front Rancher with upgrades galore. Owner has found their home of choice and is currently under contract. This beautiful home is professionally landscaped and situated on a 1+ acre level lot. Upgrades Include...New roof 5/22, New HVAC system 11/23, New Heat Pump located in the back Sunroom 11/23, New Water Heater 9/26, New Washer/Dryer 11/24 & New Stove 3/25. Please note; Septic System was pumped 4/28/26 and included a full service check of the system. This outstanding country rancher offers so many areas to entertain friends or just find a quiet spot to sit and enjoy the peaceful surroundings and wildlife. This home shows pride of ownership throughout the property. 2hr notice on showings is requested.

157 Greenwood Creek Rd, Queenstown

Listing courtesy of Cummings & Co. Realtors. Contact:

Baltimore Drive, Stevensville
$549,000
3 Beds ⋅ 2 Baths
Coming soon — brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction. Get in early and make this upcoming new construction home yours before it’s built!

Baltimore Drive, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

151 Fox Den Rd, Church Hill
$540,500
4 Beds ⋅ 4 Baths
Discover an exceptional opportunity in the desirable Church Hill Hunt subdivision. This stunning Colonial-style residence, built in 2007, offers a spacious 3,720 square feet of thoughtfully designed living space. Featuring four generously sized bedrooms and three and a half bathrooms, this home is perfect for both entertaining and everyday living. The heart of the home boasts a cozy gas fireplace with glass doors, creating an inviting atmosphere for gatherings. The partially finished basement provides additional space for recreation or storage, with both interior access and a convenient outside entrance. Enjoy the ease of upper-floor laundry and the comfort of an attached two-car garage with front entry. Set on a generous 0.86-acre lot, this property offers ample outdoor space for relaxation and activities. With no pool to maintain, you can focus on enjoying your surroundings. This residence combines modern convenience with classic charm, making it an ideal choice for discerning buyers seeking a blend of comfort and style.

151 Fox Den Rd, Church Hill

Listing courtesy of Real Estate Professionals, Inc.. Contact:

205 Anchor Ln, Chester
$500,000
4 Beds ⋅ 3 Baths
SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing connection. Outside, the possibilities continue! Enjoy morning coffee on the screened porch, entertain on the spacious deck, or take advantage of the large backyard for play, pets, gardening and gatherings. Car enthusiasts, hobbyists and anyone needing serious storage will LOVE the impressive detached 4-car garage—an increasingly hard-to-find feature on Kent Island. And the best part? NO HOA! Enjoy the freedom to make the property your own without the added monthly community expense. With 5 bedrooms, two levels of flexible living space, updated baths, multiple outdoor living areas, a huge backyard and an exceptional 4-car detached garage, 205 Anchor Lane delivers an incredible amount of home and versatility for the money. If you've been searching for true VALUE on Kent Island, this one deserves a look! 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:

114 Bayview, Grasonville
$499,000
3 Beds ⋅ 4 Baths
Open Saturday 10am-12pm! WOW! Reduced over $40,000 - Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $509,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact:

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