Refine Search
Map
Sort by
$199,900
3 Beds ⋅ 2 Baths
Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$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:

$997,000
5 Beds ⋅ 4 Baths
WELCOME to the Eastern Shore -- This charming Nantucket style waterfront home offers unique privacy with the advantage of being in a wonderful water privilege community. Rare 1.5-acre lot offers a 5 bedroom, 3.5 bath renovated beauty that offers upgrades to include: true handsome hardwood floors, stunning renovated Coastal kitchen and baths, new windows, siding and doors. There are scenic wrap-around water views from almost every room. The water depth is low and small craft is advised in the creek.... which does exit into the bay.... The community boat ramp is directly across the street for easy boating. There are a couple of garage options available for this property: The garage option is " TO BE BUILT.... County has said OK to pool and garage addition, permit process has started...

101 Beachside Dr, Stevensville

Listing courtesy of Coastal Realty Maryland. Contact:

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

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$675,000
3 Beds ⋅ 3 Baths
High End & High Efficiency! Sustainable living meets timeless craftsmanship in this incredible custom-built Nexus home. If you’ve been dreaming of a property that blends luxury, efficiency, privacy, and intentional design… this is it. Situated on an acre with NO HOA, this craftsman-style beauty was thoughtfully designed for both comfort and energy efficiency with features rarely found together in one home: Owned Solar Panels Brand New Geothermal Heating System Electric Vehicle Charging Plug-Ins Hardiboard Plank Siding for durability and timeless curb appeal Inside, the details shine: ✨ Beautiful custom moldings ✨ Updated kitchen with high-end appliances & countertops ✨ Warm, elevated finishes throughout ✨ Spaces that feel both elegant and grounded Outside is where this home truly becomes a lifestyle: 🌿 Covered porches for slow mornings and evening unwinds 🔥 Hardscaped patios perfect for entertaining ⚽️ Wide open green space for gardening, soccer games, pets, or simply breathing a little deeper An almost net-zero home with privacy, style, and functionality like this is incredibly rare.

103 Beech Tree Ln, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810
$5,900,000
7 Beds ⋅ 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, 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, lighted pickle ball courts, 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, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$149,990
HUGE PRICE ADJUSTMENT! REDUCED $47K!! Rare opportunity to own a beautiful double lot (Lots 49 & 50) overlooking the peaceful marsh of Prices Creek in the sought-after Kent Island Estates community. This oversized homesite offers the perfect setting to build your dream home surrounded by nature, wildlife, and endless water-oriented recreation. Current flood mapping indicates the proposed homesite is not located in a flood zone (buyer to verify), providing added confidence as you plan your build. Enjoy the relaxed, coastal lifestyle that makes Kent Island Estates so special. Developed in the 1950s around the opening of the first Bay Bridge, this established community now features more than 600 homes stretching from the Chesapeake Bay to the Eastern Bay along Rt. 8 toward Romancoke Pier. Residents of all ages appreciate the peaceful setting, friendly atmosphere, and abundant outdoor amenities. The South Kent Island Trail runs directly through the neighborhood, offering miles of scenic biking, walking, and jogging from Matapeake Beach to Romancoke Pier. Spend your days fishing, crabbing, kayaking, or picnicking at the pier, or simply soaking in the bay breezes. Community gatherings, social events, yoga classes, and neighborhood activities create a true sense of connection, with the community hall available for private events and celebrations. Water privileges on the Chesapeake Bay, nearby dining and shopping, and a short drive to the Bay Bridge, historic Annapolis, and St. Michaels make this an exceptional location for both full-time living and a weekend retreat. See uploaded documents for important disclosures regarding sewer costs. Build the home you’ve been dreaming of in a community where every day feels like a getaway. THIS LOT IS DIRECTLY TO THE LEFT OF 336 OREGON ROAD, STEVENSVILLE, MD (IF YOU'RE FACING THE HOUSE), SO WE SUGGEST USING YOUR GPS TO THAT ADDRESS. Contact listing agent for questions.

Lot 49-50 Bay Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$2,495,000
5 Beds ⋅ 4 Baths
Price improvement. Welcome home to this stunning waterfront property in Cove Creek Club on Kent Island. Cove Creek is a Golfer's Paradise! This remarkable five bedroom, four bathroom home offers an unparalleled blend of privacy, elegance, and panoramic coastal beauty all located on your very own private peninsula. With an impressive 566 feet of protected shoreline where Tanner’s Creek converges with Cove Creek, opening directly to the Eastern Bay, this southern-facing residence offers breathtaking water views from nearly every room. Upon entering, you’re greeted by a dramatic two-story foyer with soaring vaulted and coffered ceilings that set an immediate tone of refinement, drawing the eye straight through to the large backyard and shimmering water views beyond. The thoughtfully designed main level features high ceilings throughout and a serene primary suite with views of the pool and waterfront. The primary retreat offers a custom walk-in closet with built-ins, tray ceiling, and a spa-inspired bath with dual vanities, private water closet, soaking tub, expansive walk-in shower, and plantation shutters for added privacy. Upstairs, enjoy a recreation room with wide angle water views and balcony perfect for enjoying sunsets while playing a game of pool or darts. Four additional bedrooms can be found here as well, two on either side of the home sharing jack-and-jill style bathrooms with private closets. Designed for effortless entertaining and elevated everyday living, the open-concept living and dining spaces flow seamlessly from the beautifully updated kitchen. Here, refined finishes include soft-close cabinetry, granite countertops, a marble backsplash, center island, walk-in pantry, stainless-steel appliances, gas cooktop, wine refrigerator, and warming drawer. The kitchen opens to an inviting living room with sliding doors to access the outdoor living area. Outside you’ll find extensive hardscaping with a built-in grill, granite countertops, and a granite dining table seating eight, perfect for hosting refined waterfront gatherings. The resort-style backyard is a private sanctuary, featuring a sparkling pool and a private pier equipped with three boat lifts—ideal for boating, paddle boarding, crabbing, or simply enjoying sunsets accompanied by visits from blue herons and bald eagles. Professionally designed landscaping offers year-round color with mature plantings all complemented by a lush, level lawn maintained by a multi-zone irrigation system. Additional highlights include a spacious three-car garage with room for vehicles, golf carts, and storage, along with premium finishes throughout that reflect timeless craftsmanship and meticulous attention to detail. As a resident of Cove Creek, enjoy access to an exceptional array of private amenities including a USGA-rated golf course, deep-water marina, private beach, clubhouse, fitness center, tennis, pickleball, and bocce courts, boat ramp and storage yard, as well as miles of scenic walking and biking trails - all located on Kent Island, just minutes from the Chesapeake Bay Bridge and Route 50.

137 Tanners Point Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$530,000
2 Beds ⋅ 3 Baths
Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 20,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$949,500
5 Beds ⋅ 3 Baths
Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This room could also be used as an office, or second living area. The huge plus is the conveniently located laundry room located on the first floor. Upstairs, find three spacious bedrooms, two full baths, and a bonus room over the garage that can serve as a fifth bedroom, media room, or office. The unfinished walkout basement provides plenty of storage and potential for future living space. Outside, enjoy your private backyard with an in-ground pool, hot tub, patio, pool shed, and sweeping water views. You are surrounded by trees for tons of privacy. As a resident of Kennersley Farm, you’ll also have access to the community marina with pool and boat slips. Conveniently located near Centreville, Chestertown, beaches, restaurants, and shopping, this home offers so much and more. Your waterfront dream home awaits!!

530 Kennersley Farm Ln, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact: (717) 735-8400
$287,000
HERE IS THE CHANCE YOU HAVE BEEN WAITING FOR. WATERFRONT LOT FOR SALE WITH NO BUILDER TIE IN. NOT MANY LOTS REMAINING FOR SALE. TOWER GARDENS HAS SO MUCH TO OFFER. BOAT RAMP, PLAYGROUND ANDA RARE CHANCE TO BEING ABLE TO BUILD THAT DREAM HOUSE YOU HAVE BEEN WAITING FOR. PUBLIC SEWER ASSESSMENT IS TO BE TRANSFERRED TO BUYER.

114 N Lake Dr, Stevensville

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

$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
$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $837.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Mill Corner - E&W Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact:

$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $836.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Corner Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact: