Refine Search
Map
Sort by
$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
$989,000
5 Beds ⋅ 4 Baths
Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

2702 Sherman Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$2,850,000
5 Beds ⋅ 5 Baths
Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$60,000
Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

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

$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
$2,840,000
3 Beds ⋅ 2 Baths
Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

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

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$4,158,000
9 Beds ⋅ 8 Baths
Nestled within the prestigious Wolf Farm community, this exquisite residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This property is one of few on Kent Island that has unobstructed views of Annapolis, Baltimore and the Chesapeake Bay Bridge. Guests are welcomed with a gated circular drive adorn with stone pillars, lush flower beds and a professionally manicured lawn. The neoclassical architectural style mimics that of Thomas Jeffersons home Monticello. Spanning an impressive 10,152 square feet, the kitchen has been meticulously renovated in 2026, ensuring convenience of use while gazing at the Bay. Step inside to discover an open floor plan that invites natural light to dance across the stunning marble and luxury vinyl plank flooring. The eat-in kitchen and separate formal dining room provide ample space for entertaining, while the pantry ensures that all your culinary needs are met. The primary suite is a true sanctuary, boasting a bay-front view, a lavish primary bath, and expansive walk-in closets. Each of the nine bedrooms is designed with comfort in mind, offering generous space and thoughtful details. With eight full bathrooms, morning routines are a breeze, ensuring privacy and convenience for all. The heart of the home is complemented by three elegant fireplaces, creating cozy nooks for relaxation. Recessed lighting and upgraded countertops throughout add a touch of sophistication, while the wet/dry bar and custom wine cellar elevate your entertaining experience. Step outside to your personal oasis, where a stunning in-ground pool awaits, surrounded by multiple terraces and balconies that overlook the serene Chesapeake Bay. With 500 feet of waterfrontage, this property offers unparalleled access to the water, complete with a private composite dock that accommodates multiple slips for your boating adventures. Whether you enjoy power boating or kayaking, the navigable waters provide endless opportunities for exploration. Additional features include a full daylight basement with outside access, perfect for guests or recreational activities, and an attached side-entry garage with ample driveway space for up to 15 vehicles. This home is not just a residence; it's a lifestyle. Experience the tranquility of waterfront living combined with the luxury of modern amenities, all within the embrace of a warm and inviting atmosphere. Embrace the exclusive lifestyle that awaits you in this remarkable property.

319 Blue Bay Rd, Stevensville

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

$850,000
1 Beds ⋅ 2 Baths
This Tidewater Cape sits on the point of 13.78 acres and is surrounded by the tidal waters of the Chester River. Built to be a summer home by a father and son in 1950, this home is filled with character and charm. Drive through the woods and catch glimpses of the river to your left. Moments later, the trees open to the homesite, and then notice there is water to your right as well, showcasing the point setting. Cute and cozy from the moment you see it, but this home’s full presence is best appreciated from the rear, where the three-story Tidewater elevation stands proud and timeless. Loved and enjoyed by several generations, the home offers hardwood floors throughout the main and second levels, beautiful built-ins and gorgeous hardwood details throughout. Outdoor living includes a main-level porch and lower-level patio, perfect for taking in the peaceful surroundings. Two outbuildings are located along the shoreline: a one-car garage and a workshop with electric, they offer flexible storage and workspace. There could be potential for subdividing a lot, but buyers to verify all possibilities with the county. Pier/dock conveys As-Is — do not walk on dock. Do Not Enter Property without an appointment.

200 Powers Ln, Millington

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

$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
$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