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$856,000
3 Beds 3 Baths
Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

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

$599,999
4 Beds 3 Baths
Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

200 Ackerman Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact: 2025569721

$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

$998,000
3 Beds 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living.

111 Marshgrass Way Unit #41, Chester

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

$989,800
5 Beds 4 Baths
Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$749,000
4 Beds 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186

$349,000
3 Beds 2 Baths
Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

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

$600,000
3 Beds 3 Baths
Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

222 Moorings Cir Unit #126, Stevensville

Listing courtesy of The KW Collective. Contact: 4435741600

$2,400,000
4 Beds 4 Baths
Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$600,000
5 Beds 4 Baths
$10,000 Buyer Credit with an Acceptable Offer! Use it to Buy Down Your Rate! Use it to Build a Deck! Like new and loaded with upgrades, this stunning end-unit Baldwin townhome is just three years young and offers the perfect blend of style, space, and convenience. Featuring 4 bedrooms, 4 full baths, and 1 half bath, this spacious home was thoughtfully designed for modern living. The heart of the home is the bright white gourmet kitchen complete with quartz countertops, abundant cabinetry, a large center island, and an expanded kitchen/dining bump-out that creates an open and inviting space for entertaining. The adjoining living areas boasts a shiplap focal wall with fireplace and is filled with natural light thanks to the premium end-unit location. Retreat to the luxurious owner's suite with a private bath, while additional bedrooms and baths provide flexibility for family, guests, or a home office. Take outdoor living to the next level on the incredible rooftop deck, perfect for relaxing, entertaining, or enjoying sunset views. Additional features include an attached garage, modern finishes throughout, and the peace of mind that comes with newer construction. Conveniently located in the Ellendale community that offers an outdoor pool, community center, playground, ponds and fishing pier with kayak launch. Close to shopping, dining, commuter routes, and everyday amenities, this turnkey home offers low-maintenance living without sacrificing space or style.

310 Allison Jane Dr Unit #H-1, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$459,900
3 Beds 3 Baths
Welcome to 102 Sophie Lane in the sought-after Ellendale community of Stevensville! This beautiful end-unit townhome offers 3 bedrooms, 2 full baths, 1 half bath, and a lower level flex room, combining comfort, style, and convenience. Inside, you’ll find a functional layout that’s perfect for everyday living and entertaining, with inviting living spaces, a seamless flow throughout, and natural light that enhances the home’s warm and welcoming feel. The living room is highlighted by a stylish shiplap accent wall with an electric fireplace, creating a warm and inviting focal point. The kitchen features granite countertops and an island, while the composite rear deck provides the perfect space to relax, entertain, or enjoy your morning coffee. The bedroom closets are thoughtfully outfitted with custom California Closets® organization systems, offering both style and exceptional storage. Located in the amenity-rich Ellendale community, residents enjoy access to a community pool, piers, walking trails, playgrounds, and beautifully maintained common areas, creating the perfect setting for an active lifestyle and family-friendly living. Conveniently located just minutes from shopping, dining, schools, and with easy access to Route 50, this home offers the ideal balance of neighborhood charm and convenience. Don’t miss your opportunity to own this beautiful home in one of Kent Island’s most desirable communities!

102 Sophie Ln, Stevensville

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

$424,989
3 Beds 3 Baths
Welcome to Ellendale! This beautifully maintained townhome offers the perfect blend of comfort, convenience, and low-maintenance living.*Nestled in the back of the community overlooking the pastures of Kent Manor Inn and Community Pond. * The open floor plan features 9’ ceilings, abundant natural light, a cozy gas fireplace, and two-car garage. Upstairs you’ll find two spacious bedrooms, while the finished lower-level flex space is ideal for a home office, gym, media room, or guest retreat. Enjoy peace of mind with a newer roof and a premium location directly across from the community pond. Amenities include pool, clubhouse, walking paths, and located just minutes from the Bay Bridge. , Close to shopping, dining, marinas, and all that Kent Island has to offer. Vacant and available for a quick settlement—move in and start enjoying Ellendale community amenities include pool, club house, playground, community pier with floating dock, walking trails / side walks, and boat storage. With less than a mile to Route 50 and the Bay Bridge this home allows for quick access to Annapolis, Washington DC, Baltimore, Easton, Saint Michaels, and beyond! Community Fishing Pier**Boat Lot**Outdoor Pool**Close to Rt 50***Fresh Paint**Lots of Shopping And Plenty of Sunsets**What Are You Waiting For?

111 Ryan Dorsey Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

$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:

$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

$584,999
3 Beds 2 Baths
Have you been waiting for your own slice of paradise to come on the market? Well, the wait is over. This home offers over 2,000 sqft of living space. The open concept gives you plenty of space to entertain or areas to have seperate quiet time. Step out back and an inviting pool is waiting for you to dive into. The liner is approx 3 years old so you should have years of worry free enjoyment. This home sits on nearly an acre with mature trees that give you plenty of privacy but with plenty of open space to host large gatherings. There is a great little tiki bar that gives you the feeling of being miles from home and on vacation every day. The community offers 2 waterside areas with great sunrises and sunsets. The Eastern Bay side has the best sunrises around with a picinic area in a park like setting, a place to launch your water toys and a playground for the young ones. The Chesapeake Bay side has a great beach area for launching your (fishing)kayak, paddleboard, etc or just chiil in the sand with your feet in the surf. If you're into fishing this is the spot. Some of the best sunsets you'll ever see. If this sounds like a place you would vacation to once a year just keep in mind this is the Kent Island lifestyle you can enjoy everyday. The epoxy floored garage has an interior entrace to the home to protect you from the elements. The gourmet kitchen has a workspace, an island and a countertop bar area that give guests space to be included in the kitchen activities but out of the way of the cook. There are 3 rooms to hang out in. One is a large sunroom that leads to the backyard with an inviting ingound pool . Another has a gas fireplace and the other has a woodstove that you can cozy up to in the winter months. There is a back up generator that is included just in case. There is an active community clubhouse that offers plenty of things to do. Including but not limited to parades, cook-offs, cook-outs, santa visits, Easter egg hunts, Halloween booths, yoga classes and much more. Volunteers are always appreciated so come and be part of something special. It does the psyche good.... The South Island Trail and Romancoke Pier are just outside the community. Shopping. public schools, multiple waterside resaurants and Bay Bridge access is very convenient. Well, what are you waiting for??? Make your appointment today!!!!!

342 Wicomico Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact: 4107580333

$490,000
2 Beds 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

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

952 Chester River Dr, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

$1,350,000
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:

$575,000
5 Beds 5 Baths
Beautiful Upgraded Townhome in a Prime Location Enjoy the perfect blend of space, style, and convenience in this exceptional four-level townhome, ideally located for easy commuting and close to shopping, dining, and everyday essentials. This spacious home features numerous upgrades, including a stunning oversized kitchen island, quartz countertops, designer backsplash, stainless steel appliances, and luxury vinyl plank flooring throughout the main living areas. The open-concept layout offers abundant living space, with a large living room and dining area that comfortably accommodates six or more guests. A unique fourth-floor level provides incredible flexibility, making it ideal for a home office, guest suite, or potential fifth bedroom. This level includes its own full bathroom, living area, and walkout deck, creating the perfect private retreat. At entry level this town house has a finished bedroom and bath which is unique, most units don't have a finished bedroom and bath. With 4.5 bathrooms, this home is designed for comfort and convenience. The laundry room is thoughtfully located on the bedroom level, making everyday living easier. Additional highlights include: - Four level of living space that feels more like a single-family home. -Spacious primary suite and generously sized bedrooms. -Two car Garage plus, two car parking pads. - Modern finishes and upgrade throughout. Residence enjoys outstanding community amenities, including a community pool, kayak storage, and a pier for water enthusiasts. Conveniently located near target, food lion, and Starbucks, restaurants, and other popular retailers, this home offers everything you need just minutes away. Don't miss the opportunity to own this beautifully upgraded townhome with exceptional space, flexibility, and amenities in a highly desirable location.

212 Jessica Lyn Ave Unit #G3, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$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:

$1,990,000
6 Beds 5 Baths
The location of this property is fabulous! One of the most beautiful spots on the bay, it features a panoramic view across the bay to Annapolis! Watch the ships going in and out of Baltimore, magnificent sunsets, and the Blue Angels, when they perform! In a small neighborhood, just minutes from the Bay Bridge, the property has all you need for a year-round home or for a week-end or vacation retreat! The cement, heated in-ground pool adjoins the deck and porch areas . A small kitchen and full bath are poolside for coming in from the pool, cleaning your "catch of the day" or steaming crabs! The private pier accommodates a boat lift and two jet-ski lifts. There is rip-rap and bulk heading, and depending on the tide, there is a beach! This uniquely-designed home offers multiple living and dining areas, as well as main and second level bedrooms and a separate office. With its many three-season and screened-in porch areas and outside decks, you can entertain rain or shine! And, by the way, the golfers in the family, need not leave the neighborhood as it abuts the Blue Heron Golf Course! Instead of commuting from your primary home to a vacation home, save yourself the trip...this house has it all! There is a video security system at the property.

206 Queen Anne Club Dr, Stevensville

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

$599,000
4 Beds 3 Baths
Welcome to 130 Opera Court in the sought after community of Symphony Village at Centreville. If you've been waiting for that home resting on an exceptional lot backing to an open area and woods, then this is the home you've been waiting for. The beautiful 4 bedroom, 3 full bath home is exceptional, move in ready and just waiting for you. As you enter the home, your eyes will be drawn to the bright open floorplan and the rear windows overlooking the large deck that expands across the entire rear of the home. On the right, you'll find the front guest bedroom/office, a second guest bedroom, full bath, laundry room and access to the garage and lower level of the home. Moving through the home, you'll pass through the large living area with double sided propane fireplace, mounted TV that conveys with the home and the relaxing area and dining area on the rear overlooking the large lot backing to beautiful woods. To the right is the gourmet kitchen with granite counters, appliances including a gas stove and under cabinet lighting. The expansive primary suite is a must see with French Doors leading to the balcony, his and her walk-in closets and the primary bath with a large walk-in corner shower. Moving to the lower level, you'll find a large family area, another guest bedroom, full bath, a massive amount of storage area and a workshop leading to the rear exterior of the home. This home rests on a premium wooded lot for your relaxation while enjoying the wildlife that the area has to offer.

130 Opera Ct, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$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:

$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

$1,700,000
7 Beds 6 Baths
Set on more than six private acres in one of Kent Island’s most desirable locations, this exceptional estate offers a rare blend of luxury, scale, and refined livability. Encompassing approximately 5,680 square feet, the residence has been thoughtfully elevated through extensive improvements, resulting in a truly turnkey offering in a setting defined by privacy, presence, and the freedom of no HOA restrictions, including the ability to keep livestock. At the heart of the home, a spectacular chef’s kitchen sets the tone for both everyday living and elevated entertaining. Custom cabinetry frames a suite of premium Viking and Miele appliances, complemented by an oversized refrigerator and freezer, multiple ovens, dual dishwashers, beverage refrigeration, a dedicated ice maker, and a walk-in pantry. This is a space designed to perform just as well for quiet evenings as it does for large gatherings. A soaring two-story family room anchors the main level, filled with natural light and centered around a newly installed pellet stove insert. The main-level primary suite serves as a private retreat, featuring a fully reimagined spa-inspired bath with a steam shower, soaking tub, and bespoke cabinetry. Across three finished levels, seven bedrooms provide remarkable flexibility for multi-generational living, guests, home offices, or creative pursuits. Throughout the home, refreshed interiors, custom built-ins, and thoughtful updates contribute to a cohesive sense of comfort and refinement. Outdoors, the property unfolds like a private resort. An expansive patio, gazebo, curated landscaping, and swimming pool create an effortless setting for entertaining or quiet relaxation. The surrounding acreage enhances the sense of seclusion, with space for recreation, gardening, livestock, or simply enjoying the quiet rhythm of estate living. The detached two-story garage extends the property’s versatility, with a dedicated fitness studio above and generous space below for vehicles, equipment, hobbies, or future expansion. What truly distinguishes the property is the quiet confidence of what has already been accomplished. Comprehensive improvements to core systems and infrastructure ensure a level of reliability and peace of mind rarely found in homes of this scale, allowing the next owner to simply arrive and enjoy. Despite its private and pastoral setting, the estate remains just minutes from Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Eastern Shore. Positioned near the highly regarded Matapeake school campus, it offers a rare combination of seclusion, accessibility, and everyday convenience. Rarely does a property combine acreage, scale, and refinement in such a complete way. This is more than a home. It is a private Kent Island estate designed for living well, entertaining effortlessly, and enjoying space without compromise.

102 Little Neck Rd, Stevensville

Listing courtesy of HomeSource Pro Real Estate. Contact: (443) 454-1470

$565,900
2 Beds 3 Baths
Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

115 Gibson Cir, Chester

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