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$299,999
Tenant occupied, income producing two unit property in downtown Grasonville now available! The front house (B) rents for $1200 per month to a month to month tenant. The house (B) has 3 bedrooms and 2 baths. The 2 bed 1 bath second floor garage apt rents for $1378 per month to month to month tenants. All tenant spay their own utilities.

106 Phyllis Ct, Grasonville

Listing courtesy of Alberti Realty, LLC. Contact: 4439818000
$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
$569,900
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:

$640,000
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:

$499,000
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
$994,000
5 Beds ⋅ 3 Baths
Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level.  Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

14 Fairway Is, Grasonville

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

$599,000
4 Beds ⋅ 3 Baths
Offering a 2-1 rate buydown Built in 2024, this beautifully maintained 4-bedroom, 2.5-bath home offers all the benefits of a brand-new home without the wait, construction delays, or additional upgrade expenses. Step inside to a light-filled, open-concept floor plan designed for today's lifestyle. The spacious kitchen serves as the heart of the home, seamlessly connecting to the dining and living areas—perfect for entertaining friends, hosting holiday gatherings, or simply enjoying everyday life. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with room to relax and recharge. The conveniently located second-floor laundry room makes everyday living just a little easier. Step outside to your private, fully fenced backyard featuring a covered patio/gazebo—an ideal space for morning coffee, summer cookouts, evening conversations, or simply unwinding after a busy day. A two-car garage and thoughtfully designed floor plan provide the storage and functionality today's buyers appreciate. Perry's Retreat offers a true neighborhood feel with sidewalks, a community playground, and plenty of opportunities to enjoy the outdoors. Located just minutes from the Chesapeake Bay, Chesapeake Bay Environmental Center, marinas, shopping, dining, and Route 50, you'll enjoy convenient access to Annapolis, Kent Island, and the entire Eastern Shore while coming home to a peaceful community.

612 Pathfinder Cir Unit #BALLENGER, Grasonville

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

$525,000
3 Beds ⋅ 4 Baths
Save up to $320/month with a Lender Paid 1 Point Buy Down with accepted offer by 6/30/26 - Ask Lender for details! Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $540,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810
$425,000
3 Beds ⋅ 4 Baths
Waterfront Lifestyle with Included Boat Slip – Bayview at Kent Narrows Experience the best of Eastern Shore living in this beautifully renovated 3-bedroom, 3.5-bath contemporary townhouse with garage, ideally located just over the Kent Narrows Bridge in the sought-after Bayview waterfront community. Waterview's from second and third floor bedrooms. This move-in-ready home features a stunning new kitchen with stylish gray shaker cabinetry, granite countertops, and stainless-steel appliances. The open-concept living and dining areas are enhanced by new luxury vinyl plank flooring, creating a modern, inviting space perfect for everyday living and entertaining. The spacious primary suite offers vaulted ceilings, abundant natural light, a ceiling fan, double closet plus walk-in closet, and a dressing area. The completely renovated spa-inspired primary bath is a true showstopper, featuring a luxurious oversized double shower with dual shower heads, built-in benches, niches, and sleek glass doors. Two additional generously sized bedrooms provide excellent flexibility, including one with a private en-suite bath, plus a third full hall bathroom for guests. Step outside and embrace the water-privileged lifestyle this community offers. Your assigned boat slip is in the private community marina, complete with water and electricity, and included in the monthly condo fee. Launch directly into Muddy Creek, which leads straight to the Chester River—putting you just minutes by boat from Red Eye Dock Bar, Harris’ Crab House, and The Dock House Restaurant. Additional highlights include: •

109 Bayview, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$1,215,000
3 Beds ⋅ 4 Baths
Perfectly positioned along the living shoreline of the Chester River, this waterfront residence in the gated community of Narrows Pointe offers breathtaking, million-dollar water views and a lifestyle centered around the beauty of the Eastern Shore. One of the few wide units in the community, the home is thoughtfully designed to maximize its remarkable setting. Three-panel sliding glass doors invite in abundant natural light while framing sweeping water views, and decks on two levels with retractable electric screens create inviting spaces to relax while overlooking the shoreline. A spectacular arrangement of windows throughout the home continually draws your eye to the tranquil river setting. Another plus- Seller has paid the current $10,000 assessment, so the buyer will not be obligated to that. Inside, hardwood flooring, recessed lighting, and a neutral color palette welcome you upon entry. The gourmet kitchen serves as the heart of the home and features granite countertops, a center island with breakfast bar, tile backsplash, wine refrigerator, and 42-inch cabinetry with under-mount lighting and convenient roll-out drawers for easy organization. High-end stainless steel appliances complete the space, and the adjacent dining room provides a bright setting for everyday meals or entertaining. Just off the kitchen, a walk-in pantry and laundry room add everyday convenience and extra storage. Also on the kitchen level is a bedroom suite currently used as an office, enhanced with built-ins that create a comfortable workspace while still offering flexible guest accommodations. The living room showcases a dramatic angled ceiling, a striking stone fireplace, and custom built-ins, creating a warm gathering space while keeping the focus on the surrounding water views. Upstairs, generously sized bedrooms each include en-suite baths with granite-topped vanities. The primary suite offers a peaceful retreat with a walk-in closet featuring built-in organization, a private deck overlooking the river, and a luxurious bath with remote blinds, double vanity, jetted self-cleaning tub, and Toto toilet. Both of the upper-level bedrooms were enhanced with updated hardwood flooring in 2020. The lower-level recreation room adds another versatile living area with a custom bar and cabinetry, making it an ideal space for entertaining. The finished garage features a granite flake floor and storage cabinetry, and the home also includes a whole-house speaker system. Architectural plans are available for the future addition of an elevator. Recent improvements include whole-house interior painting completed in 2020, replacement of the living room sliding glass door, updated electric screens, a 75-gallon water heater, built-ins throughout, professional installation of a TV mount above the fireplace, finished garage upgrades, carpeting and stair runner, water softener, and more. Located near the heart of Kent Narrows, the home offers easy access to a casual waterfront lifestyle with marinas, boating activities, community piers, a kayak launch, and a variety of waterfront restaurants and tiki bars. The Cross Island Trail begins just outside the Narrows Pointe entrance, while shops, hotels, and multiple fitness centers, some with pools, are all within a convenient 10-minute drive. Nearby outdoor destinations such as the local dog park and Terrapin Nature Park add even more ways to enjoy the natural beauty of Maryland’s Eastern Shore.

350 Narrows Pointe Dr, Grasonville

Listing courtesy of Northrop Realty. Contact: 4102956579
$662,550
4 Beds ⋅ 3 Baths
Welcome to The Corsica, a beautifully designed two-story home offering 1,664 square feet of well-planned living space. With 4 bedrooms and 2.5 bathrooms, this layout is ideal for anyone seeking both functionality and modern style. Step inside to an inviting open-concept Kitchen, Eating, & Great Room, perfect for entertaining or relaxing with loved ones. The kitchen features an attached large island overlooking the spacious living area, ensuring you’re always part of the conversation. Natural light fills the space, creating a warm and welcoming atmosphere for everyday living. Convenience meets practicality with the Mud/Laundry Room located just off the garage, providing a seamless transition from outdoor activity to the home’s main living areas which is perfect for busy mornings or returning from weekend adventures. Upstairs, you’ll find four comfortable bedrooms, including a private primary suite with a full bath and walk-in closet. Three additional bedrooms share a second full bathroom, offering flexibility for guests, family, or a home office. An optional 16' x 12' rear deck expands your living space outdoors and is ideal for dining or enjoying quiet evenings surrounded by nature. Charming curb appeal, efficient design, and thoughtful flow make The Corsica the perfect place to call home. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, an open concept floor plan, and a convenient mud room. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit #LOT 2, Grasonville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$664,650
4 Beds ⋅ 2 Baths
Welcome to the Syberry, a thoughtfully designed single-story home offering 1,710 square feet of modern comfort and convenience. This 4-bedroom, 2-bathroom layout blends open-concept living with functional flow, perfect for today’s lifestyle. At the heart of the home, the spacious Kitchen, Eating, & Great Room create an inviting open area ideal for entertaining and family gatherings. Large windows fill the space with natural light, while the kitchen’s central island provides plenty of prep and seating space to keep everyone connected. The private primary suite offers a peaceful retreat, complete with a generous walk-in closet and en-suite bath. Three additional bedrooms provide flexible options for family, guests, or a home office. From the one car garage, a convenient Mud/Laundry Room connects directly to the main living area, keeping daily routines organized and tidy. An optional 16' x 12' rear deck expands your living space outdoors, perfect for morning coffee or evening relaxation. With its timeless exterior, open interior design, and practical layout, the Syberry delivers the ideal balance of comfort, efficiency, and charm all in a single-level home built for the way you live. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, open concept floor plan, garage with shop/storage, convenient Mud Room, and a covered front porch. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit #LOT 1, Grasonville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,275,000
3 Beds ⋅ 4 Baths
REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AND a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. The result was a wider Dining Room adding more natural light, wider decks, and more WATERVIEWS! Inside you'll find an open floor plan that's perfect for entertaining! It has hardwood floors, a dramatic floor to ceiling stone fireplace, a gourmet kitchen with high end newer stainless steel appliances & finishes, granite countertops, and ensuite bathrooms in all the bedrooms! Enjoy Beautiful Water Views from nearly every room thanks to thoughtfully designed architectural windows. Two covered decks with remote controlled screens invite you to relax and take in the breathtaking views over the Chester River. You also have a 2 car attached garage! Located in an exclusive gated community on a private peninsula, this home backs up to the renowned Safe Harbor Marina that offers a pool, fitness center, and over 600 slips, making it a boaters dream! Narrows Pointe is just around the corner from many great ( docking) restaurants, tiki bars, coffee and dessert spots! Golf enthusiasts will love being just 5 minutes from Queenstown Golf Links, close to other courses too! Outlet shopping is nearby for convenience. Only 20 minutes from Annapolis and Easton, 45 minutes from BWI Airport, 55 minutes from Washington, DC & Baltimore, and 1 1/2 hours away from Ocean City ! Whether you're looking for a year-round residence or a weekend retreat, this home offers the ultimate Chesapeake Bay lifestyle !

346 Narrows Pointe Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535
$1,375,000
4 Beds ⋅ 5 Baths
BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR GARAGE AND A MONSTROUS DETACHED GARAGE WITH ROOM FOR 6 MORE CARS. PLENTY OF STORAGE. BEAUTIFUL, PRIVATE INGROUND GUNITE POOL. CALL LISTING AGENT FOR MANY MORE AMENITIES. READ HOA DOCS IN DISCLOSURES. TRY TO GIVE 1-2 DAYS SHOWING NOTICE, PLEASE.

105 Port Ct, Grasonville

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