Grasonville Homes with Colonial Style

Grasonville Homes with Colonial Style

Welcome to Grasonville, Maryland – a hidden gem nestled in the heart of Queen Anne’s County, where history and modern living blend seamlessly. This charming town, situated along the picturesque shores of the Chesapeake Bay, offers a unique blend of serene waterfront views and vibrant community life. With its rich maritime heritage and welcoming atmosphere, Grasonville is an ideal place for those seeking a tranquil retreat without sacrificing convenience.

One of the defining features of Grasonville is its stunning array of Colonial-style homes. These elegant residences, characterized by their classic symmetry, brick facades, and inviting front porches, evoke a sense of timeless charm that appeals to both history enthusiasts and modern homeowners alike. The Colonial architecture found throughout the area reflects the region’s storied past while providing spacious interiors and modern amenities that cater to today’s lifestyle.

Living in Grasonville means enjoying the best of both worlds: a peaceful suburban environment with easy access to the bustling towns of Easton and Annapolis. Residents can indulge in outdoor activities, from boating and fishing on the bay to hiking the nearby trails. The local community is vibrant and friendly, with numerous events and gatherings that foster connections among neighbors.

Whether you’re a first-time homebuyer or looking to invest in a Colonial-style property, Grasonville offers a welcoming community that feels like home. Explore the charm of this delightful town, where every street tells a story, and every home is a piece of history waiting for you to discover.

Newest Grasonville Homes with Colonial Style

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

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

4 Beds ⋅ 3 Baths

PRICE IMPROVEMENT! $10K REDUCTION! Why wait for new construction when this barely lived-in home in the desirable community of Perry’s Retreat is available now? Welcome to 128 Perry’s Retreat Boulevard, offering a bright, open-concept main level with LVP flooring throughout and a layout designed for everyday living and easy entertaining. The spacious kitchen features an oversized island, stainless steel appliances, pantry, quartz countertops, soft-close cabinetry, and plenty of room to gather. The main level also includes a convenient half bathroom, office space, garage access, an oversized coat closet, and a walkout to the spacious backyard. Upstairs, you’ll find four carpeted bedrooms, two full bathrooms, and a conveniently located laundry area. The beautiful primary suite features a tray ceiling, spacious walk-in closet with natural light, and an upgraded en-suite bathroom with LVP flooring, a dual vanity, and a shower with built-in seating and dual showerheads. Outside, enjoy a covered front porch with space for seating, a spacious backyard, and a maintenance-free vinyl privacy fence. Perry’s Retreat offers sidewalks throughout the community, playgrounds, and additional parking for boats, RVs, and extra vehicles. The location is another major bonus, with quick access to Route 50 and close proximity to Kent Island, the Narrows, Annapolis, Easton, St. Michaels, local dining, shopping, golf, boat launches, and Chesapeake Bay favorites. This move-in ready home offers the benefits of newer construction, a convenient Eastern Shore location, and no wait!

128 Perrys Retreat Blvd, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

4 Beds ⋅ 3 Baths

Beautifully maintained home tucked away in a small enclave of just 46 homes, conveniently located just off Route 50 in Chester. This spacious property offers a 2-car garage complete with a utility tub and whole-house water softener system. Major updates provide peace of mind, including a newer roof and HVAC system. The encapsulated crawlspace features a dehumidifier and sump pump for added efficiency and protection. Step outside and enjoy your private backyard retreat featuring a deck, patio area, fire pit, hot tub, sunshade awning, storage shed, and fully fenced yard—perfect for entertaining or relaxing. Inside, the kitchen is designed for gathering with abundant cabinet and counter space, a custom island, granite countertops, and an open, functional layout. The main level features LVP flooring, an updated powder room, spacious living room with a cozy wood-burning stove, dining area, and dedicated office/flex space. Upstairs you’ll find four generously sized bedrooms and an updated hall bath. The oversized primary suite offers a beautifully updated bathroom featuring a separate soaking tub and stand-up shower, walk-in closet, and a unique niche room located between the bedroom and closet. This versatile bonus space offers endless possibilities—nursery, sewing room, reading nook, fitness area, office, or private retreat. Need even more space? On the upper level ,A possible fifth bedroom with closet, fresh paint, and new carpet provides flexibility as a bedroom, media room, playroom, home gym, or bonus space. Convenient Eastern Shore living with quick access to Route 50, shopping, dining, and commuting routes. Located in an intimate community of just 46 homes, this property combines space, flexibility, and thoughtful updates both inside and out.

324 Loblolly Way, Grasonville

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

4 Beds ⋅ 3 Baths

Welcome to 336 Timber Lane—a beautifully maintained Colonial offering the space, comfort, and lifestyle today's buyers are looking for, all in a convenient Grasonville location just minutes from Kent Island and the Bay Bridge. With over 2,100 square feet, this move-in ready home features 4 bedrooms, 2.5 baths, hardwood flooring, a cozy fireplace, and a spacious, flowing floor plan designed for everyday living and effortless entertaining. The bright kitchen overlooks the family room, creating the perfect gathering place for holidays, game nights, or simply spending time together. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet and private en-suite bath, while three additional bedrooms provide flexibility for family, guests, a home office, or fitness space. Step outside and enjoy a generous backyard with plenty of room for entertaining, gardening, play, or simply relaxing after a day on the water. One of Grasonville's best-kept secrets is the lifestyle. You'll enjoy quick access to marinas, waterfront restaurants, boating, fishing, shopping, and Route 50—all while experiencing less congestion than many neighboring communities. Best of all, this home offers an incredible opportunity to enjoy the Eastern Shore lifestyle while getting more home for your investment than many comparable properties on Kent Island. Whether you're commuting, raising a family, or looking for a place to enjoy everything the Chesapeake Bay has to offer, 336 Timber Lane delivers the perfect blend of space, value, and location.

336 Timber Ln, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

2 Beds ⋅ 3 Baths

Tucked away in a peaceful community on the Chesapeake Bay, this 2 bedroom, 2.5 bathroom townhouse with a loft offers the perfect mix of comfort, charm, and bay living. Situated on a desirable corner lot, the home features beautiful hardwood floors, a spacious kitchen with plenty of room to cook and gather, and a cozy fireplace that makes the living space feel warm and inviting on a winter day. **Boat Slip Included & Dredging has been started!** Step outside onto the large deck and take in the views — the perfect spot for morning coffee or relaxing evenings by the Bay. The loft adds extra flexible space for a home office, guest area, or additional lounge space. Residents also enjoy access to a private community pool, making it easy to enjoy everything this lifestyle has to offer.

118 Bayview, Grasonville

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

4 Beds ⋅ 5 Baths

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

105 Port Ct, Grasonville

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

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Joseph Ciganek

As an Eastern Shore Realtor, I know that a real estate transaction is built on trust. I pride myself on my honesty and integrity in providing the highest quality representation for my clients. I have spent my entire life in Chestertown and on the Chesapeake Bay and have a deep respect and understanding for why life here is so special. You can rely on my deep knowledge of the eastern shore and its waterways when buying a home. As an Eastern Shore native, full-time Realtor and licensed Attorney, I have the skill set to help you navigate any real estate transaction; waterfront, farms, commercial, you name it. Buying or selling real estate requires an experienced and trustworthy advocate. Let me be your guide. Growing up on the banks of the Chester River, I was fortunate enough to enjoy everything the Chesapeake Bay has to offer, whether crabbing, fishing or just about every water-sport you can think of. After graduating from Washington College with a B.A. in Economics and Finance, I attended University of Baltimore School of Law. Working full time and going to school at night, I graduated cum laude and proceeded to clerk for the Honorable Harris P. Murphy, Circuit Court of Kent County, Md. That’s when I decided to make a drastic career shift to practicing full time as a Realtor in 2021. Since then I have enjoyed showing others why life on the shore really is the land of pleasant living. Outside of real estate, I enjoy getting exercise with my black lab, playing pickleball, soccer and racing the historic log canoe sail boats up and down the Chesapeake Bay.

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