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$695,000
4 Beds ⋅ 3 Baths
Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz countertops, GE Café appliances, brand-new Bosch high-efficiency inverter heat pumps, new luxury vinyl plank flooring and a large waterfront deck perfect for entertaining or simply relaxing while taking in the scenic water views. Additional features include an attached two-car garage, detached garage/storage building, private deep well and county sewer. Enjoy boating, fishing, kayaking, biking and running right outside your door. Located near Blackwater National Wildlife Refuge and public hunting lands, this property is ideal for outdoor enthusiasts and nature lovers. Conveniently located near the Madison public boat ramp, volunteer fire company and just 15 minutes from Route 50 and Cambridge, with shopping, restaurants and Emily's Produce nearby. Whether you are looking for a full-time residence or private waterfront retreat, this property offers the very best of Maryland's Eastern Shore lifestyle.

4825 Madison Canning House Rd, Madison

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$349,990
4 Beds ⋅ 4 Baths
Beautifully positioned backing to the golf course, this move-in ready luxury 4-level end-unit townhome is located in Lennar's premier waterfront community of Tides at River Marsh on Maryland's scenic Eastern Shore. Offering 3 bedrooms, 3 full baths, 1 half bath, and a 2-car garage, this home features luxury vinyl plank flooring, a spacious kitchen with a large quartz island, stainless steel appliances, and stylish cabinetry. The finished walk-out lower level provides additional living space with direct outdoor access, while the expansive fourth-level loft opens to a private rooftop deck, perfect for relaxing or entertaining. Adjacent to the Hyatt Regency Chesapeake Bay Resort, residents enjoy resort-style amenities including a clubhouse, swimming pool, walking and biking trails, tennis and pickleball courts, championship golf, and nearby marina access. Conveniently located just minutes from downtown Cambridge's shopping, dining, and waterfront attractions, with easy access to Annapolis and Delaware beaches.

2206 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$249,900
2 Beds ⋅ 2 Baths
Experience the best of Eastern Shore living in this beautifully appointed, fully furnished condo located in a gated waterfront community. This turnkey home offers 2 spacious bedrooms, 2 full bathrooms, and 1,610 square feet of thoughtfully designed living space. Designer furnishings throughout create an elegant, move-in-ready retreat, making it perfect as a full-time residence, weekend retreat or investment. Enjoy the relaxed waterfront lifestyle with the comfort, security, and amenities of this exceptional community.

700 Cattail Cove Unit #411, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$324,900
2 Beds ⋅ 3 Baths
Welcome to 329 Shipyard Drive, a spacious townhome in one of Cambridge's most convenient waterfront communities. Offering over 2,400 square feet of living space, this home features an open, functional floor plan with generous room sizes, abundant natural light, and plenty of space for everyday living or weekend getaways. The main living area flows nicely into the kitchen and dining space, making it easy to entertain family and friends. Upstairs, you'll find comfortable bedrooms, including a spacious primary suite with its own private bath and ample closet space. Located in a gated, water-oriented community, residents enjoy access to a community pool and the convenience of being just minutes from downtown Cambridge's restaurants, shops, marina, and waterfront parks. Whether you're looking for a full-time residence, a low-maintenance second home, or an investment opportunity, this property offers the perfect combination of space, location, and easy living on Maryland's Eastern Shore.

329 Shipyard Dr, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$439,900
3 Beds ⋅ 2 Baths
Whether you're dreaming of a peaceful country lifestyle or ready to bring your horses home, this picturesque farmette on nearly 5.5 acres is ready for you. The property is already set up with established pastures, a barn featuring four stalls and a feed room and plenty of space for horses and other animals. The updated 3 bedroom, 2 full bath farmhouse blends modern updates with timeless charm and features newer mini-split heating and cooling systems, a cozy pellet stove and a convenient first-floor primary bedroom. A detached two car garage includes a 1 bedroom, 1 bath apartment above, ideal for guests, extended family, rental income, or a private home office.

5125 Rhodesdale Rd, Rhodesdale

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$349,990
3 Beds ⋅ 3 Baths
Welcome to Tides at River Marsh, an exceptional community adjacent to the renowned River Marsh Golf Club and Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina along the scenic Choptank River. Residents enjoy resort-style amenities, including a clubhouse, swimming pool, and walking and biking trails, with convenient access to historic downtown Cambridge's waterfront dining, shopping, museums, and marinas. Annapolis, Easton, and Ocean City are all within easy reach. This move-in ready villa offers 3 bedrooms, 2.5 bathrooms, and a 2-car garage. The gourmet kitchen is beautifully appointed with quartz countertops, a designer tile backsplash, stainless steel appliances, double wall ovens, and a vented range hood. Wide-plank flooring flows throughout the main living areas, complementing the open-concept design. Relax year-round on the screened porch or entertain on the paver patio while enjoying peaceful open-space views and added backyard privacy. Experience low-maintenance living with luxury finishes in one of Maryland's premier Eastern Shore communities.

2129 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$362,000
4 Beds ⋅ 2 Baths
Calling nature lovers; the private Eastern Shore retreat you've been searching for. This potential AIr BnB home set in the heart of Maryland's Lower Eastern Shore offers the peace, privacy, and wide-open space that outdoor enthusiasts value most. Surrounded by natural habitat and abundant wildlife, the area is well known for frequent sitka deer sightings and exceptional opportunities to enjoy the outdoors right from your own backyard. Whether you're looking for a hunting retreat, recreational property, or full-time residence with room to roam, this property delivers. The home features 4 bedrooms, a dedicated office, and 2 full bathrooms, along with a remodeled kitchen that serves as the perfect gathering place after a day outdoors. Additional amenities include a spacious floore attic, a fenced yard with an above-ground pool, a barn with multiple stalls, and a storage shed, and a brand-new generator, providing both convenience and functionality for country living. Located in Toddville, a community known for its rich watermen's heritage, scenic marshlands, and unspoiled landscapes, you'll enjoy easy access to the outdoor lifestyle the Eastern Shore is famous for. Spend your days hunting, fishing, crabbing, boating, kayaking, birdwatching, or simply enjoying the quiet beauty that surrounds you. Whether you're searching for a basecamp for outdoor adventures, a weekend getaway, or a peaceful place to call home, 1511 Crocheron Road offers the space, privacy, and natural setting to make it all possible.

1511 Crocheron Rd, Bishops Head

Listing courtesy of A Squared Realty. Contact: 804-432-8149
$650,000
4 Beds ⋅ 3 Baths
Welcome to 4657 Maiden Forest Road! This is a wonderful compound surrounded by beautiful country farms! 4657 is a uniquely-built, lovely, brick home with gorgeous flagstone porches & great one level living! This house boasts over 3000 SF of living space with 4 BR's and 2.5 BA's. The highlight of the house is a 27' by 22' great room with a magnificent cathedral wood ceiling and floor to ceiling brick fireplace with a gas log insert. The loft above offers endless potential but currently serves as a great pool hall & it has walk-in attic storage. The spacious kitchen has a breakfast bar in addition to a generous array of cabinets & an adjacent dining area with a wood cook stove. The living room has beautiful custom-built bookcases and a brick fireplace with a top-notch pellet stove insert. The primary ensuite, complete with skylight, is located conveniently just off the great room. There are 3 additional bedrooms and 1.5 additional baths. The powder room, near the spacious laundry room, is easily accessd from the wonderful in-ground saltwater pool. The 48' X 32' metal outbuilding has 12' ceilings, is fully insulated and has two 10' OHDs with garage door openers, propane heater, 220 electric service, running water, a plethora of workspace and even a series of dog kennels! The detached garage 28' X 24' has 2 bays wih automatic door openers. The 3rd bay, closest to the poo,l has been converted to a pool house/crab room complete with a brick bbq, a mini split and ample room for a crab picking crowd! 4657 boasts an ample-sized patio with gazebo, brick entrance pillars and walkway and 1.27 acres of land surrounded by acres and acres of farmfields. Country living at its best!

4657 Maiden Forest Rd, Rhodesdale

Listing courtesy of Compass. Contact: (410) 429-7425
$324,900
3 Beds ⋅ 3 Baths
Move right into this beautiful home in Cambridge’s historic district! It features a fully updated kitchen and baths, a new HVAC system, and a picture-perfect front porch. The attic and crawlspace have been improved for optimum energy efficiency. For a fun, modern twist, head up the cool spiral staircase to a fully finished third-floor space. Outside, enjoy a fantastic backyard with raised garden beds already in place, a storage shed, and alleyway access. Off-street parking. Love the look? The owner will even consider parting with some of the furnishings!

109 Willis St, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$434,900
2 Beds ⋅ 2 Baths
Welcome to Penthouse #302 at Oakley Beach, one of Cambridge’s most desirable waterfront condominium communities. Perched on the top floor, this beautifully appointed 2-bedroom, 2-bath residence offers breathtaking panoramic views of the Choptank River and the convenience of low-maintenance waterfront living. Inside, you'll find an open and inviting floor plan featuring 9-foot ceilings, gleaming hardwood floors, and a well-appointed kitchen with granite countertops, quality cabinetry, and ample workspace. The spacious living area is accented by a cozy gas fireplace and opens directly to a covered balcony where you can relax and take in the stunning river vistas. A rare and highly desirable bonus, the sale includes a deeded boat slip, providing direct access to the Choptank River and making it easy to enjoy boating, fishing, and waterfront adventures right from your community. Located within Cambridge’s Historic District, Oakley Beach is just minutes from downtown shops, restaurants, galleries, and waterfront attractions. This thoughtfully designed penthouse is ideal as a full-time residence, weekend retreat, or vacation getaway. With only 24 residences spread across four elevator-served buildings, residents enjoy a peaceful and private setting along with exceptional community amenities, including a swimming pool, common pier, beautifully maintained grounds, and abundant guest parking. If spectacular water views, upscale finishes, and turnkey living are what you're seeking, Penthouse #302 at Oakley Beach deserves your attention.

3 Oakley St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$359,990
3 Beds ⋅ 4 Baths
Located in Lennar’s premier waterfront community of Tides at River Marsh on Maryland’s scenic Eastern Shore, this move-in ready luxury 4-level end-unit townhome offers the perfect blend of coastal living and modern convenience. Nestled in Cambridge adjacent to the Hyatt Regency Chesapeake Bay Resort, residents enjoy resort-style amenities including a clubhouse, swimming pool, walking and biking trails, tennis and pickleball courts, and access to a nearby marina. Surrounded by championship golf, boating, nature trails, and wildlife preserves, the community is also just minutes from downtown Cambridge’s shops, restaurants, and waterfront attractions, with convenient access to Annapolis and Delaware beaches. This beautifully designed home features a 2-car garage, 3 bedrooms, 3 full baths, and 1 half bath, luxury vinyl plank flooring, a spacious kitchen with a large quartz island, stainless steel appliances, and stylish cabinetry. The finished walk-out lower level provides additional living space with direct outdoor access, while the expansive 4th-level loft offers flexible living space and opens to a private rooftop deck, perfect for relaxing or entertaining. Agents must accompany buyers on their first visit.

2198 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$249,990
3 Beds ⋅ 3 Baths
Lennar’s Tides at River Marsh is a premier resort-style community on Maryland’s scenic Eastern Shore in Cambridge, surrounded by the natural beauty of the Choptank River and the acclaimed River Marsh Golf Club. Residents enjoy a relaxed waterfront lifestyle with exceptional amenities, including a clubhouse, swimming pool, walking and biking trails, tennis and pickleball courts, and nearby marina access. Conveniently located adjacent to the Hyatt Regency Chesapeake Bay Resort and just minutes from downtown Cambridge, Blackwater National Wildlife Refuge, and Route 50, the community offers easy access to shopping, dining, recreation, Annapolis, and Ocean City. This move-in ready luxury end-unit townhome features a 2-car garage, 3 bedrooms, 2 full baths, and 1 half bath. The gourmet kitchen showcases stainless steel appliances, quartz countertops, a decorative backsplash, and wide-plank flooring throughout the main living areas. The spacious owner’s suite includes upgraded tile in the bath, while the finished walkout lower level provides additional living and entertaining space. Enjoy private wooded views from this desirable homesite. Photos are for illustrative purposes only. Agent must accompany first visit.

2185 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$359,900
4 Beds ⋅ 3 Baths
From the inviting front porch, upgraded stone-accented exterior, to the to the fully fenced backyard, this beautifully maintained 4BR/2.5BA is ready to impress. Natural light fills the open living spaces, highlighted by a cozy gas fireplace and a stylish kitchen featuring granite countertops, stainless steel appliances, a pantry, and a center island perfect for gathering. The main level also offers a private office, or an additional welcome area, while upstairs you’ll find four spacious bedrooms, convenient second-floor laundry, and a generous primary suite with a walk-in closet and dual-sink vanity. Solar panels provide added efficiency, and community amenities including a pool and docks offer the perfect setting for enjoying the Eastern Shore lifestyle. Simply unpack and start enjoying everything this beautiful home and amenity-rich community have to offer.

502 Regulator Dr S, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$179,900
2 Beds ⋅ 2 Baths
New price reduction! This charming 2-bedroom, 2-bathroom, top floor unit in the desirable Deep Harbour gated community offers a blend of comfort and convenience. Enjoy access to the community pool, Cambridge Creek and many local amenities such as shopping, dining, and recreational activities. Available for purchase or lease.

900 Marshy Cv Unit #401, Cambridge

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

$370,990
4 Beds ⋅ 4 Baths
Enjoy stunning golf course views from the backyard of this beautifully designed two-story villa featuring a spacious paver patio and attached two-car garage. Designed for comfortable main-level living, the home offers a luxurious first-floor owner’s suite and an open-concept layout perfect for everyday living and entertaining. The gourmet kitchen flows seamlessly into the dining area and expansive Great Room, creating a bright and inviting gathering space. Upstairs, an open loft overlooks the Great Room and provides additional flexible living space. Three secondary bedrooms surround the loft, including a second owner’s suite—ideal for multi-generational living, extended guests, or added privacy. The additional bedrooms offer plenty of room for family, visitors, a home office, or hobby space. Combining elegant finishes, thoughtful design, and picturesque golf course views, this exceptional home delivers both comfort and versatility.

2125 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$395,000
4 Beds ⋅ 3 Baths
Built just one year ago and barely lived in, this spacious 4-bedroom, 2.5-bath home in Longboat Estates offers modern comfort and an unbeatable Eastern Shore lifestyle. The open-concept floor plan features luxury vinyl plank flooring, a beautifully appointed kitchen with granite countertops, stainless steel appliances, and a large center island, all flowing into a bright family room with a gas fireplace. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bath with dual vanities and an oversized tiled shower. An attached two-car garage, generous living spaces, and a private backyard backing to trees complete the package. Enjoy access to community amenities including a pool, boat ramp, and dock. Conveniently located just minutes from downtown Cambridge, waterfront dining, marinas, the Choptank River, Blackwater National Wildlife Refuge, and the Harriet Tubman Underground Railroad Visitor Center. Enjoy the benefits of nearly new construction without the wait!

178 Regulator Dr N, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$359,990
4 Beds ⋅ 3 Baths
Enjoy stunning golf course views from this brand-new construction villa featuring a desirable main-level owner’s suite and a low-maintenance lifestyle. Thoughtfully designed, this two-story home offers an open-concept layout with soaring ceilings, a gourmet kitchen, spacious family room, versatile flex space, and a luxurious primary suite on the first floor. Upstairs, a central loft provides additional living space and is surrounded by three secondary bedrooms, along with an unfinished storage area for added convenience. Outdoor living is equally impressive with a screened porch and private paver patio overlooking the golf course—perfect for relaxing or entertaining while taking in the scenic views.

2131 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$305,000
3 Beds ⋅ 4 Baths
Beautiful End-Unit Townhome Loaded with Upgrades – Move-In Ready! Welcome home to this stunning 3-bedroom, 2.5-bath end-unit townhome located in the desirable gated community of Deep Harbour. Offering modern upgrades and spacious living across three levels, this home combines comfort, style, and convenience. The first floor features wood flooring, a large recreation room or home office, complete with a convenient half bath and access to the attached one-car garage. On the second level, you'll also find wood flooring throughout with an open and inviting floor plan featuring a spacious kitchen with Corian countertops, upgraded cabinetry, stainless steel appliances, and a dining area with access to a generous 10' x 20' deck—perfect for entertaining or relaxing outdoors. The large living room provides ample space for gathering, while the stylish shiplap accent wall in the half bath adds a touch of charm. Enjoy the amazing cross breeze when the windows are open. The third level features a spacious primary suite with a tray ceiling, walk-in closet, and an elegant en-suite bath offering a double vanity and a large tiled walk-in shower. Two additional bedrooms and a full bath complete this level. Residents of Deep Harbour enjoy gated community amenities, including a community pool, marina, and scenic jogging and walking paths. Conveniently located near downtown entertainment, dining, shopping, and grocery stores, you'll have everything you need just minutes from your doorstep. Don't miss the opportunity to own this beautifully maintained townhome in one of the area's most desirable waterfront communities. Schedule your private showing today! Tenant occupied -available for ownership on or after August 17, 2027

301 Shipyard Dr Unit #59, Cambridge

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265
$429,900
3 Beds ⋅ 2 Baths
Luxury waterfront living awaits in this updated 3-bedroom (rare) Oakley Beach condo! Enjoy sweeping views of the Choptank River from the deck and a beautifully modernized kitchen featuring sleek quartz countertops ,custom island, and updated cabinet fronts. New LVP flooring. Gas fireplace, Hunter Douglas blinds including insulated, mechanized shade for as much or little view as you want ! Recent HVAC and hot water heater.(2023) Boat enthusiasts will love the included deeded boat slip equipped with a boat lift. Take advantage of fantastic community amenities like the pool, all just steps from your door. Truly worry free and move in ready! Schedule your tour today!

3 Oakley St Unit #202, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$895,000
4 Beds ⋅ 3 Baths
Welcome to 6011 Sunnyside Court...a true destination! This waterfront sanctuary has been completely refreshed with fabulous interior paint and a brand new 30 year roof! It is complimented by a sparkling saltwater pool and wide-open views of the Warwick River -your own resort! Moreover, this property provides great supplemental income for the astute investor. Enjoy the river-front complex when time allows yet rent "the resort" easily while you are otherwise engaged. This listing is unique in that it is sited on land that provides great views of the river which makes it a very popular airbnb property yet no flood insurance is required. It was designed with generously-sized rooms, a beautiful pool side leisure area and ample gardens. In sum, it is a splendidly built, upscale oasis in East New Market. The house is perfectly sited on a spacious 1.2 acre parcel in which to enjoy all seasons. This stylish hide-a-way has it all. Five bedrooms, upscale finishes and room to play. The first floor is fantastic with a wide open floor plan, 2 full bedrooms, a powder room, covered porch and views galore! A gracious living room has French doors overlooking and leading to the pool area. A modern white kitchen has island seating, tons of counterspace and opens to a large dining space with river and pool views. The sunroom has walls of windows and steps to an inviting patio area. The second floor is upscale with room for friends and family. A private primary suite has wonderful views, a stylish bath and great closet space. Two additional bedrooms and bath and laundry complete this light-filled floor. The third floor has great potential with a soaring ceiling and large windows promising future fun! The waterfront pool, inviting patios, riverfront dock and green gardens await your arrival. The saltwater pool is surrounded by a wrought iron fence, secure, yet allows views from all points. The patio has room for games and lounging. Garden areas and game playing lawns are ready for fun. An uncovered pergola and a top of the line dock is ready for your toys and boats. Parking for everyone and the best view in East New Market can be yours! Restaurants and shopping are close by too.

6011 Sunnyside Ct, East New Market

Listing courtesy of Compass. Contact: (410) 429-7425
$399,900
4 Beds ⋅ 4 Baths
Experience resort-style living at an exceptional value in the Residences at River Marsh. Perfectly positioned between the Hyatt Chesapeake Bay Golf Resort, Spa & Marina and the award-winning River Marsh Golf Club, this beautifully maintained 4-bedroom, 3.5-bath townhome offers the ideal blend of waterfront recreation, golf course views, and luxury amenities on Maryland's Eastern Shore. Located just a short stroll from the marina on the Choptank River, boaters will appreciate the opportunity for annual marina memberships with slips available to keep your boat in the water and ready for your next adventure. Golf enthusiasts will enjoy front-row views of the 2nd fairway and 3rd hole from multiple outdoor living spaces, including a ground-level patio, screened porch, and private balcony off the primary suite. Inside, the thoughtfully designed three-level floorplan features hardwood flooring, a spacious center-island kitchen with stainless steel appliances, breakfast bar seating, dining area, and an inviting living room ideal for entertaining family and friends. A front porch overlooking the Hyatt grounds offers glimpses of the marina and resort atmosphere that makes River Marsh one of the Eastern Shore's premier destinations. The upper-level primary suite serves as a private retreat with balcony access, customized California Closets, and an upgraded spa-inspired shower featuring body sprays, handheld wand, and traditional  shower head. Additional custom California Closets throughout the upper-level bedrooms and pantry provide exceptional organization, while updated lighting fixtures add a fresh, sophisticated touch throughout the home. The attached one-car garage provides ample storage for golf clubs, bicycles, boating equipment, beach gear, and everything needed to enjoy the River Marsh lifestyle. Optional memberships are available for golf, community amenities, and select Hyatt resort privileges, allowing owners to tailor their experience to their interests. Enjoy the convenience of walking to the marina, Blue Point Provision Company, golf course, resort amenities, and scenic waterfront trails. Whether you're seeking a full-time residence, weekend getaway, or vacation property, this is an outstanding opportunity to own in one of Cambridge's most desirable resort communities. Best of all, it is currently the best-priced townhome opportunity in River Marsh.

2820 Persimmon Pl Unit #B4, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$359,900
3 Beds ⋅ 2 Baths
Now featuring a brand-new roof and a $15,000 price improvement! Welcome to 7112 E. New Market Ellwood Road, a versatile 3-bedroom, 2-bath home situated on nearly 2 acres in a quiet country setting. This great small farmette is already equipped with fenced areas, a run-in stable, and a large storage shed, offering an excellent setup for horses, livestock, or hobby farming. The converted garage is currently set up as a pet-grooming space and offers plenty of possibilities. Continue using it as a home-based business, transform it into a den or family room, or convert it back into a garage. Outside, enjoy the above-ground pool with deck, plenty of usable yard space, and room for a future pole building or additional outbuildings. Conveniently located within a short drive of Cambridge and Easton, this property offers country living with easy access to shopping, dining, and everyday conveniences. With a brand-new roof, a significant price improvement, and a motivated seller, this farmette is ready for its next owner. Schedule your showing today!

7112 E New Market Ellwood Rd, Hurlock

Listing courtesy of Taylor Properties. Contact:

$367,000
2 Beds ⋅ 2 Baths
WATER VIEWS THROUGHOUT * 1841 sq ft * CORNER CONDOMINIUM HOME * GATED PRIVATE * OPEN CONCEPT * 2 BEDROOMS * 2 FULL BATHS * GARAGE PARKING * 2 ELEVATORS * POOL * PET FRIENDLY* Imagine waking up to water views from every window in your *1841 sq ft* corner condominium home! This gated, private property boasts an open concept, perfect for entertaining. With two bedrooms and two full baths, plus a garage and two elevators, you’ll have plenty of space to enjoy. Plus, it’s pet-friendly! This unit is bright and airy, and you’ll be amazed by the size and volume of the Easton Model floor plan. The 9 ft tall ceilings and lots of large windows fill the space with natural light and offer beautiful views of Cambridge Creek and Trenton St. Marina. The kitchen has a classic, timeless look with stainless appliances, maple cabinetry, and solid surface countertops. The kitchen, which includes a breakfast nook, opens up to the dining, living, and sunroom areas, creating a seamless flow. The sunsets are truly spectacular! This fenced, gated property is secure with security cameras. The condo includes one assigned garage parking spot, plus plenty of overflow parking for you and your guests. Relax and cool off at the onsite pool, pool house with bathrooms and shower amenities, or simply enjoy the sun. The condo is freshly painted in neutral tones, clean, and ready to move in. You’ll also find newer high-traffic laminate flooring and an AC unit with powerful airflow. The energy-saving Aqua Therm combination furnace with a 50-gallon hot water tank system makes heating and cooling efficient. Plus, there’s a convenient locked individual storage room on the main floor. All appliances, including the washer and dryer, are included. This is a second home for the seller, gently used and never rented out. The HOA takes care of the roof, exterior siding, exterior lighting, landscaping, and snow removal. There’s a one-time capitalization fee, a post-settlement fee, and two monthly HOA fees required by the buyer at settlement. This is an outstanding unit, one of the largest available, and a great choice!

700 Cattail Cv Unit #104, Cambridge

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$349,900
4 Beds ⋅ 3 Baths
Beautifully maintained and newly refreshed 4BR/2.5BA Colonial in sought after Longboat Estates. Park in the double-wide driveway or attached two-car garage and enter through the covered front entry into a light-filled interior featuring fresh paint, luxury flooring, carpeting, and recessed lighting. The main level offers a welcoming living room, convenient half bath, and an open-concept layout perfect for everyday living and entertaining. The spacious family room with gas fireplace flows seamlessly into the dining area with sliding door access to the backyard. The kitchen features ample cabinetry with under cabinet lighting, granite countertops, tiled backsplash, stainless steel sink, a pantry, and a movable island with a wood top. A stylish mudroom with barn doors provides access to the garage, complete with a custom epoxy floor. Upstairs, enjoy the convenience of second-floor laundry, three generously sized bedrooms, a full bath, and a private primary suite featuring a walk-in closet and en suite bath with double vanity and a large walk-in shower. From the main floor's sliding doors, step outside to a newly installed paver patio overlooking expansive green space and backing to woods, perfect for relaxing or entertaining. This move-in ready home also includes an in-home sprinkler system and is located in a community offering a fenced pool, boat ramp, and piers. Conveniently located near shopping, dining, and major commuter routes.

138 Regulator Dr N, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$1,399,000
6 Beds ⋅ 5 Baths
Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property designed for gathering generations of family and friends. A long private approach welcomes you to a setting where nature and waterfront living take center stage. Inside, hardwood floors, timeless architecture, and expansive Bay views create a warm yet elegant atmosphere. The waterfront family room features a striking stone fireplace with wood-burning insert and opens seamlessly to both the screened porch and covered deck, creating effortless indoor-outdoor living. The spacious kitchen was designed with entertaining in mind, offering a center island, breakfast bar, abundant cabinetry, stainless steel appliances, double wall ovens, pantry storage, and an oversized breakfast room ideal for casual mornings by the water. Formal living and dining rooms provide additional space for hosting holidays and special occasions. The first-floor primary suite serves as a private waterfront sanctuary with direct access to the covered porch and peaceful Chesapeake Bay views. Upstairs, five spacious guest bedrooms and three full baths—including a private en-suite—offer flexibility for large families, guests, or vacation rental potential. Vaulted ceilings and dormer windows add architectural charm and natural light throughout the second level. Outside, the lifestyle only gets better. Spend summer days around the inground pool, rinse off in the outdoor shower after boating or kayaking, enjoy crab feasts on the screened porch, or gather around the waterside fire pit as the sun sets across the Bay. The partially wooded acreage provides exceptional privacy while attracting an abundance of wildlife including bald eagles, deer, ducks, geese, and shorebirds—an everyday reminder of the natural beauty that surrounds you. Located on Ragged Point with Eastern Shore favorites like Soft & Salty Seafood and Danny's Seafood, this property offers easy access to fresh seafood, marinas, boating, and some of the finest fishing and crabbing waters on the Chesapeake Bay. The nearby Neck District Grill is a great spot for breakfast, lunch or weekend dinner. Whether you are searching for a full-time waterfront residence, luxury weekend escape, or investment opportunity with proven vacation rental appeal, this extraordinary property delivers the privacy, waterfront lifestyle, and authentic charm that buyers are seeking on Maryland’s Eastern Shore.

5332 Ragged Point Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$419,000
4 Beds ⋅ 3 Baths
Think you have seen this home?...better LOOK AGAIN!! This home has been refreshed inside and out and is simply stunning! From the moment you step inside you will notice the fresh, coastal design that welcomes you home. You will find light, airy hardwood floors throughout the home and a beautiful kitchen featuring furniture-finished cabinetry and upgraded counter tops, and ceramic tile floor. The breakfast bar has seating for up to five plus there's an additional breakfast area that is drenched in sunlight. The kitchen blends seamlessly into the family room featuring high ceilings, a gas fireplace, and custom built-in server cabinetry. This home features a spacious first floor owner's bedroom suite with soaking tub and walk in shower, plus a second bedroom with full bath and even a separate den/office. First floor laundry. Relax in the sun room overlooking the backyard or step out onto the covered rear porch and patio. Take the staircase up to the second floor to find 2 more huge bedrooms with a connecting "Jack and Jill style" full bath #3. This exceptional home features over 3700 Sq ft of quality built, craftsman style living space! The community of Longboat Estates is everything shore life should be! It is a beautiful community! An active, yet relaxing place to call home offering homeowners exclusive amenities to enjoy shore life... you will find the beautiful dock with 2 piers on Jenkins Creek leading out to the Choptank River. Bring your boat, kayak, fishing and crabbing gear. You and your family will love it here! Quality construction by Lennar.

123 Regulator Dr N, Cambridge

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$250,000
3 Beds ⋅ 3 Baths
Charming 3-Level Townhome in a Gated Waterfront Community with Pool, Clubhouse & Marina Access! Welcome to this beautifully maintained 3-bedroom, 2 full-bath townhome located in a sought-after gated community Deep Harbour. This spacious three-level home features a first-floor expanded rec/ family room with new plank flooring, 1/2 bath and direct access to the community pool area. Second floor offers spacious Livingroom, a bright and inviting Kitchen with an abundant cabinet space, Corian countertops, additional built-in cabinets and bar, stainless appliances and a dining area filled with natural light overlooking the pool. Private side deck, also overlooking the pool — perfect for relaxing or entertaining. Third floor Spacious primary ensuite includes a soaking tub, separate shower, double sink vanity, sitting room and walk-in closet. Two additional generously sized bedrooms provide comfort and flexibility for family, guests, or a home office. Attached 1-car garage also includes Extra guest parking. Access to marina walking areas and community amenities. Convenient location just minutes from downtown shopping, grocery stores, fine dining, and entertainment. Enjoy low-maintenance living in a waterfront-inspired community with exceptional convenience and amenities.

324 Shipyard Dr Unit #83, Cambridge

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265
$1,195,000
4 Beds ⋅ 4 Baths
Welcome to a rare Eastern Shore offering where privacy, income potential, and waterfront lifestyle come together on 23± acres along the Little Choptank River. Currently a successful vacation rental, this property presents an exceptional opportunity for a second home that works for you—enjoy it when you want and generate income when you’re away. The expansive acreage provides a peaceful, private setting with endless possibilities—gardening, small-scale farming, hunting, or enhancing the land with an impoundment or pond to attract waterfowl. The waterfront is fully equipped for enjoying life on the water with a partially rip-rapped shoreline, private pier and approximately 2.5 feet of mean low water depth—ideal for boating, fishing, and crabbing, with easy access to Fishing Creek and the Chesapeake Bay beyond. Outdoor living truly shines with an in-ground pool overlooking the water, offering a serene setting for both quiet relaxation and entertaining. The spacious wooden deck provides ample room for dining and gatherings, while taking full advantage of the surrounding views. An outdoor shower adds a practical touch, making it easy to rinse off after time spent on the water or enjoying the outdoors. The 4-bedroom, 3.5-bath residence is designed for comfort and gatherings, offering an open floor plan with two primary suites, each with private baths. The spacious kitchen is a true centerpiece, featuring a large island with breakfast bar, double wall ovens, cooktop, refrigerator, dishwasher, beverage refrigerator, and separate ice maker—fully equipped to handle everything from intimate dinners to large-scale entertaining. The adjacent dining room easily accommodates gatherings, while the family room, just off the kitchen, captures serene water views and opens to a spacious screened porch for seamless indoor-outdoor living. A sunroom adds additional living space, also overlooking the pool and waterfront, creating the perfect spot to unwind year-round. The home’s low-maintenance brick exterior, attached two-car garage with automatic opener, and thoughtful layout make it as practical as it is inviting. Conveniently located approximately 2 hours from Washington, DC and 1.5 hours from Baltimore, this property offers the perfect escape without sacrificing accessibility. Whether you’re seeking a private retreat, an income-producing investment, or a place to fully embrace the Eastern Shore lifestyle—boating, fishing, crabbing, kayaking, paddleboarding, and more—this property delivers. Don’t miss the opportunity to own a truly unique waterfront estate with everything in place for summer enjoyment—schedule your private tour today and start living the lifestyle you’ve been waiting for.

1661 Town Point Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$427,104
4 Beds ⋅ 3 Baths
This well-maintained home offers approximately 3,772± sq. ft. with 4 bedrooms and 3 full baths, featuring an open floor plan, 9-foot ceilings, hardwood flooring, and bright living spaces throughout. The main level includes a spacious primary suite with a spacious walk in closets, and a large bath featuring double vanities, soaking tub, and separate shower. Additional first-floor spaces include a formal dining room with tray ceiling, living room with gas fireplace, study/office, family room, sunroom, guest bedroom, full bath, and laundry room with wash tub. The kitchen is designed for entertaining with an open connection to the main living areas, upgraded cabinetry and stainless appliances, granite countertops, tile backsplash, gas cooktop, and breakfast bar seating, The sunroom leads directly to the screened porch and fenced backyard, creating comfortable indoor-outdoor living space. The second floor offers two oversized guest bedrooms, an updated full bath, walk-in attic access, and substantial storage areas. One upstairs bedroom is additionally equipped with a mini-split system for enhanced comfort and efficiency. Additional interior features include a large conditioned crawl space accessed from inside the home by a dedicated staircase tucked within a closet. The space is well-lit, spans beneath the entire residence, and offers extensive storage and access to major utility components including the water heater and air handler. Exterior improvements include a welcoming brick front porch with column detail, attached garage, screened rear porch, fenced backyard, and solar panels. Longboat Estates is a 162-home waterfront community conveniently located near downtown Cambridge restaurants, shops, marinas, parks, wildlife areas, and Route 50 for easy access across the Eastern Shore. Community amenities include a private pool, pier/dock area, and boat launch on Jenkins Creek with access to the Choptank River and Chesapeake Bay.

119 Regulator Dr N, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$259,990
3 Beds ⋅ 3 Baths
Beautiful corner homesite offering a private backyard that backs to a scenic golf course, delivering exceptional, million-dollar views. This home presents an incredible value with a desirable setting and special financing opportunities available.

2203 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact: