Dorchester County Public Schools Homes with Pool - Outdoor Amenities

Dorchester County Public Schools Homes with Pool - Outdoor Amenities

Welcome to the vibrant community of Cambridge, Maryland, where the charm of small-town living meets the allure of picturesque landscapes. Nestled in Dorchester County, this area is not only known for its stunning waterfront views and rich history but also boasts an exceptional educational system: the Dorchester County Public Schools. This district is dedicated to fostering a nurturing environment for students, offering a wide range of programs designed to inspire and engage learners of all ages. With a focus on academic excellence, innovative teaching methods, and community involvement, parents can feel confident that their children are receiving a top-notch education.

For those seeking a home in this idyllic region, you’ll find an array of properties that cater to your lifestyle, particularly those with outdoor amenities such as private pools. Imagine relaxing on a warm summer day, lounging by your own sparkling pool, or hosting memorable gatherings with family and friends in your spacious backyard. Homes with pools in Cambridge not only provide a refreshing retreat but also enhance your outdoor living experience, allowing you to fully embrace the beauty of Maryland’s seasons.

Whether you’re looking for a cozy single-family home or a luxurious estate, the real estate options in Cambridge are as diverse as its residents. With the added benefit of being part of the esteemed Dorchester County Public Schools district, you’ll find that this community is perfect for families, professionals, and anyone looking to enjoy the best of Maryland living. Explore your options today and discover your dream home in Cambridge!

Newest Dorchester County Public Schools Homes with Pool - Outdoor Amenities

$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
$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
$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:

$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
$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
$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
$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
$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
$399,000
3 Beds ⋅ 4 Baths
Experience elevated coastal living in this exceptional three-level townhome in the sought-after Deep Harbor community on Cambridge Creek. Unlike anything else in the neighborhood, this residence showcases over $100,000 in post-purchase custom upgrades and curated designer finishes; crafted for the buyer who expects the very best. From the moment you step inside, the attention to detail is unmistakable. Custom wainscoting, 6" crown molding, luxury wallpaper, and bespoke drapery and window treatments create a refined, cohesive aesthetic that carries throughout the home. The entry level offers a comfortable family room, powder room, and access to a beautifully designed paver patio, perfect for relaxing or entertaining. The main living level is both stylish and functional, centered around a stunning gourmet kitchen featuring stainless steel appliances, quartz countertops, ceramic tile backsplash, and an oversized island ideal for gathering. The showstopping Ortal Wilderness gas fireplace, framed by soapstone and shiplap, adds a level of sophistication and warmth rarely found, which is truly a signature feature that sets this home apart. A dining area and private balcony provides seamless options for indoor or outdoor dining. Upstairs, the primary suite is a serene retreat, complete with tray ceiling, private balcony, and a spa-inspired bath featuring tempered tile, a frameless walk-in shower, and thoughtful luxury finishes. The walk-in closet is outfitted with a custom California Closet system for optimal organization. The second bedroom is equally impressive with custom California Closets and a built-in window seat that would be ideal as a beautifully appointed home office or guest space. The third bedroom continues the theme of quality and comfort. Outdoor living has been thoughtfully enhanced across three separate spaces, with added privacy elements including strategic landscaping, separation from neighboring homes, outdoor lighting, irrigation, and improved drainage...creating peaceful, usable environments at every level. Even the garage has been elevated with a custom cabinetry system and overhead storage solutions. Located within walking distance to downtown Cambridge, you’ll enjoy easy access to local restaurants, shops, and the brewery, all while residing in a waterfront community offering amenities such as a pool, walking paths, and direct water access on Cambridge Creek. Perfectly positioned for convenience, this home is approximately 2 hours from Washington, D.C. and just 1.5 hours from Baltimore, making it an ideal primary residence or weekend retreat. Opportunities like this are rare. Schedule your private showing today and discover what it means to own one of Deep Harbor’s most distinctive and refined homes.

416 S Seaway Ct Unit #142, Cambridge

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

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