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$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: 4102083500
$645,000
5 Beds ⋅ 3 Baths
Your private resort awaits. From the moment you arrive, this stunning home commands attention with its timeless curb appeal, oversized corner lot, and impressive presence. Offering over 5,000 square feet across three levels, this is the perfect blend of luxury, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open floor plan designed for both entertaining and daily living. The spacious two-story family room with a cozy fireplace flows seamlessly into the heart of the home, a beautifully appointed kitchen featuring a large center island, granite countertops, stainless steel appliances, abundant cabinetry, beverage refrigerator, and an oversized breakfast area overlooking the backyard. Whether you're hosting holiday dinners in the formal dining room, enjoying quiet mornings in the sun-filled living spaces, or gathering with friends around the kitchen island, every room has been thoughtfully designed for making memories. Upstairs, the expansive primary suite offers a true retreat with a spa-inspired ensuite bath, generous walk-in closet, and plenty of room to unwind. Spacious secondary bedrooms provide flexibility for family, guests, or a home office. The basement level adds even more living space with endless possibilities for a recreation room, fitness area, media room, or additional guest accommodations. Then step outside... The backyard is where this home truly shines. Imagine summer afternoons spent in the sparkling in-ground pool, evenings under the custom pavilion complete with an outdoor kitchen and bar, relaxing around the fire pit, and entertaining on the expansive paver patio, all surrounded by a fully fenced backyard offering privacy and space to enjoy. This isn't just a backyard, it's your own private vacation destination. Conveniently located near shopping, dining, parks, schools, and major commuter routes, this exceptional home offers the lifestyle you've been waiting for. Luxury. Space. Resort-style living. Welcome home.

122 Fair Brook Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$379,000
2 Beds ⋅ 1 Baths
Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

3801 Main St, Grasonville

Listing courtesy of Fairfax Realty Select. Contact: 7035932381
$1,250,000
5 Beds ⋅ 3 Baths
Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$929,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, 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 elegant workspace. The kitchen is designed for both 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 #2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, 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 elegant workspace. The kitchen is designed for both 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 #2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$2,850,000
5 Beds ⋅ 5 Baths
Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$999,990
3 Beds ⋅ 3 Baths
Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, 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.

110 Boatswain Way Unit #3044, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$629,990
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: 4102083500
$649,900
4 Beds ⋅ 3 Baths
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:

$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, 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 elegant workspace. The kitchen is designed for both 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 #2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$749,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, 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 seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. 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.

110 Boatswain Way Unit #3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$1,500,000
4 Beds ⋅ 3 Baths
Waterfront on the Corsica River—opportunities like this don't come along every day! Proudly positioned on a spectacular 2-acre lot with approximately 540 feet of shoreline, this exceptional 4-bedroom, 3-bath home offers breathtaking panoramic views and an unmatched waterfront lifestyle. Located at the end of a quiet cul-de-sac in the established community of Corsica Landing Estates, just outside Centreville town limits, you'll enjoy the benefits of no town taxes or HOA fees. Mature landscaping and thoughtfully designed hardscaping create a private setting that perfectly complements the expansive river views. Designed for entertaining, the backyard is truly a waterfront oasis. Enjoy the in-ground concrete pool with diving board, a spacious hot tub housed in its own versatile room for year-round enjoyment, and a 145-foot private dock with approximately 6 feet of mean low water, complete with electric, water, two boat lifts, and a floating dock. Whether you prefer relaxing in the sun or unwinding in the shade, the beautifully landscaped outdoor living spaces have something for everyone, including an expansive 47.5' x 18' Trex deck with two pergola-like covered cooking and dining areas and a spacious waterside patio. Inside, the home offers comfortable living with generous spaces throughout. The eat-in kitchen features granite countertops, stainless steel appliances, including a new oversized refrigerator, and a separate wet bar with wine refrigerator and wine rack. The main level also includes a spacious living room with a wood-burning fireplace, an oversized formal dining room, a home office with custom built-ins and a large bay window, a full bath, and a convenient laundry/mudroom. One of the home's standout features is the incredible waterside sunroom, filled with natural light from walls of windows and offering spectacular views of the pool and river. Complete with a beautiful stone propane fireplace and ceiling fans, it's the perfect place to relax in every season. The spacious primary suite includes hardwood flooring, a walk-in closet, dual vanities, a walk-in shower, and direct access to a large 18.5' x 24' bonus room above the garage. With its own private staircase from the attached two-car garage, this flexible space is ideal for a guest suite, recreation room, fitness area, studio, or additional home office. Next to the garage is an attached exterior storage/utility room which provides even more convenience. THE FINISHED LIVING AREA SQUARE FOOTAGE FOR THIS HOME IS LARGER THAN THE ASSESSMENT OFFICE REPRESENTS AND THE GOOGLE SATELLITE IMAGE MAP DOES NOT REFLECT ALL OF THE PROPERTY. PLEASE SEE DEEDS AND MAPS ATTACHED IN THE DOCUMENTS. Numerous updates have been completed over the years, including the HVAC system and ductwork, roof, triple-pane windows and sunroom doors with a lifetime warranty. The pool was renovated in 2016, with a new pool pump and skimmer pipe installed in 2023 and a new pool motor in 2026. The well pump was replaced and lowered in 2007, offering additional peace of mind. Whether you're searching for a full-time waterfront residence, the ultimate family gathering place, or a home designed for entertaining, this remarkable property delivers. With boating, fishing, kayaking, swimming, and unforgettable sunsets right from your backyard—and a county boat ramp, playground, and pavilion just minutes away—there's still plenty of summer left to enjoy. Schedule your private tour today and experience everything this extraordinary Corsica River property has to offer. Located within an hour to Baltimore, Washington, DC or Delaware. Stay Tuned For Professional Photos Coming Soon !

405 Quail Run Dr, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$625,000
4 Beds ⋅ 4 Baths
Govern Grason - This home is ready for you to move in. The house has been freshly painted inside and outside; you will appreciate the hardwood floor throughout. The home features 4 bedrooms 3.5 baths and additional space for home office and Walkin storage area that would be finished for more living space if needed. Partial basement, as well as a nice garage with new doors and openers. All located on 2.17 acres. This house is a must see!

109 Governors Way, Queenstown

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

$449,000
3 Beds ⋅ 2 Baths
Immaculately maintained and tucked away on a quiet street, this charming home offers the perfect blend of privacy and convenience with easy access to Route 50—ideal for commuters. Thoughtfully designed as an elevated residence, the home is built above grade to help reduce flood risk while providing a versatile lower level complete with a hobby room and attached garage. The main living level boasts a bright, open-concept floor plan where the kitchen, dining, and living areas flow seamlessly together, creating an inviting space for both everyday living and entertaining. A beautiful sunroom, surrounded by windows, fills the home with abundant natural light and opens to a wraparound balcony, extending the living space outdoors. Also on the main level is a flexible bonus room that can easily serve as a home office, den, studio, or other space to suit your lifestyle. Upstairs, you'll find two spacious bedrooms, a full bath, and a conveniently located laundry area. Large windows throughout the home create a warm, light-filled atmosphere, while the fully fenced yard provides a secure space for pets, play, or outdoor enjoyment. Combining comfort, versatility, and an excellent location, this delightful property is a must-see for buyers seeking a peaceful setting with convenient access to shopping, dining, and major commuter routes.

121 Marshy Creek Rd, Grasonville

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$549,987
4 Beds ⋅ 3 Baths
Nestled on a peaceful country setting, this well-maintained colonial offers the perfect blend of privacy and comfort. Featuring 4 bedrooms, 2.5 baths, and soaring cathedral ceilings, the home is filled with natural light and spacious living areas. Enjoy cozy evenings by the fireplace or entertain outdoors in your private backyard oasis complete with a saltwater in-ground pool and a large fenced rear yard. The attached 2-car garage and expansive driveway provide plenty of parking. Conveniently located just a short drive from shopping, dining, schools, and major commuter routes, this home offers the tranquility of country living without sacrificing convenience. Electric solar panels to reduce your monthly energy cost. Don’t miss this exceptional opportunity!

611 Clark Corners Rd, Centreville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$549,900
4 Beds ⋅ 3 Baths
Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

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

$525,000
2 Beds ⋅ 3 Baths
Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$825,000
4 Beds ⋅ 3 Baths
Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful golf course views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535
$1,350,000
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:

$669,900
3 Beds ⋅ 2 Baths
Welcome to your private Eastern Shore oasis at 116 Mallard Drive, Stevensville, MD 21666! This beautifully maintained and recently updated Cape Cod home sits on a rare 1.1-acre lot in a quiet, private neighborhood on Kent Island — one of the hardest-to-find lot sizes in this desirable area. Enjoy serene, protected views of Mallard Pond, where you can watch ducks glide across the water, sip morning coffee on the screened porch, and truly experience peaceful Kent Island living at its finest. Boasting 1,976 square feet of above-grade living space (built in 2000), this 3-bedroom, 2-bath home features thoughtful updates throughout. Enjoy new LVP flooring and carpet, a bright open-concept main level perfect for everyday living and entertaining, and a stunning kitchen with granite countertops and all new appliances. The spacious primary suite includes a luxurious soaking tub and walk-in closet, while two additional bedrooms and a full bath complete the main level. A 2-car garage and newer furnace add convenience and peace of mind. The standout feature is the large unfinished attic with electrical wiring and HVAC already extended — substantial, flexible space ready for your vision. Easily finish into additional bedrooms, a home office, playroom, or family suite. Outside, the expansive 1.1-acre lot delivers exceptional privacy and natural beauty, bordered by community-owned preserved woodlands and Mallard Pond that ensure your views remain undisturbed for years to come. Enjoy the screened porch overlooking the pond, low-maintenance exterior, low HOA fees of only $17 per month, and the incredible location on Kent Island — walk or bike to the public golf course, Kent Island Trail, waterfront parks, piers, and just minutes from Chesapeake Bay adventures, shopping, and dining. This updated home combines solid construction, modern finishes, low monthly costs, and a truly rare 1.1-acre private setting. Whether you’re looking for a peaceful full-time residence or a lifestyle property with room to grow, 116 Mallard Drive is a standout opportunity on Kent Island. Don’t miss it!

116 Mallard Dr, Stevensville

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

$559,000
4 Beds ⋅ 3 Baths
Welcome to Symphony Village in Centreville a 55+ Active Adult Community that HAS IT ALL! DON'T MISS THIS OPPORTUNITY! This thoughtfully maintained home offers over 3,190 square feet of living space as well a Sky Basement w/ 520 (approx.) square feet of additional storage space, Featuring 4 Bedrooms, 3 full baths, Roof 2019, Water Heater 2026, Washer/Dryer 2023, New Front Porch, Sidewalk plus drainage 2023, HVAC Units 2012, The Bright open main level includes Kitchen with extended granite countertops, stainless steel appliances, while the flowing layout includes hardwood floors, custom Blinds & Shades, and inviting living and dining areas. A GLORIOUS sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious Professionally Landscaped Patio, perfect for relaxing or hosting guests! The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower Plus a fabulous Sitting Room/Office, Upstairs, a versatile loft provides the perfect setting for a Sports Bar area Etc., along with a guest bedroom complete with its own full bath and walk-in closet, 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. Community HOA fee includes Partial Sprinkler system on your property! 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, Oxford and Annapolis. also, UMMS and UM Shore Regional Health are building a state-of-the-art medical center in Easton, set to open in 2028, This is more than a home, it is a LIFESTYLE .

510 Symphony Way, Centreville

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

$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. 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:

$650,000
3 Beds ⋅ 3 Baths
Contemporary home in Prospect Bay offering approximately 2,850 square feet of living space and available for the first time since 1999. Features 3 bedrooms, including 2 on the main level, and 2.5 baths. The family room includes a fireplace and triple sliders leading to the deck. Spacious primary suite. Loft overlooking the family room, ideal for a home office, sitting area, or additional living space. Separate dining room and dedicated mudroom with laundry. Complete with a 2-car garage and deck overlooking the backyard. Located in Prospect Bay Golf and Country Club. Club amenities include: golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

24 Fairway Is, Grasonville

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
$569,000
4 Beds ⋅ 3 Baths
Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

223 Overlook Dr, Queenstown

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$610,000
4 Beds ⋅ 3 Baths
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 TLC and your own personal touches and updates, 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! Motivated Seller!!

122 Lently Farm Ln, Centreville

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