Dorchester County Real Estate Search

Dorchester County Homes with a Pool for Sale

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Newest Dorchester County Homes with a Pool for Sale

$349,000
3 Beds ⋅ 3 Baths

106 Markley Ct, Cambridge

Listing courtesy of Eastern Shore Properties, ESP Inc.. Contact:

$550,000
3 Beds ⋅ 3 Baths
If you’re looking for space, privacy, and a touch of country living, this charming 2011 3-bedroom, 2.5-bath Cape style home has it all! Set on 6.52 +/- acres, this property offers a perfect blend of comfort, convenience, and outdoor living, with endless opportunities for expansion and recreation. Step inside to enjoy the spacious layout, ideal for both everyday living and entertaining. The kitchen features elegant granite countertops and flows seamlessly into large living and dining areas. With 2-zoned A/C, you'll stay comfortable throughout the seasons. Outside, the possibilities are endless! There's a concrete pad-approx. 34.5'x63', already prepared for your future pole building or garage, a fenced-in area for horses or farm animals, includes a chicken coop and stable. Love nature? Take advantage of the private walking path to the water, perfect for launching a kayak or simply soaking in the serene surroundings. Whether you're relaxing on the front porch, enjoying the rear deck, or cooling off in the above-ground pool, this property offers the perfect blend of indoor comfort and outdoor adventure. This home is a must-see to truly appreciate the room, privacy, and potential it offers. Don’t miss out—schedule your showing today!

4270 Beulah Rd, Hurlock

Listing courtesy of Keller Williams Select Realtors. Contact: (410) 972-4000
$1,350,000
4 Beds ⋅ 2 Baths
Welcome to the ideal Eastern Shore hideaway, where breathtaking views of the Chesapeake Bay meet serene countryside living. This expansive 22+/-acre property offers a cohesive blend of comfort, natural beauty, and wide-open space. The main house offers 4 generously sized bedrooms and 2 bathrooms, complemented by a charming detached guest suite with an additional 2 bedrooms and 1 bathroom. The detached garage offers ample space for outdoor equipment. This stunning property features a private dock, a heated 10-foot-deep pool, and two scenic ponds—all set amidst serene woodlands teeming with turkeys, deer, geese, and ducks for the avid hunter or wildlife enthusiasts. Recent upgrades to the property include a fully paved driveway, new second floor deck on the main house, and upgraded vinyl in the heated pool.

5476 Ragged Point Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$470,000
4 Beds ⋅ 3 Baths
Welcome to quiet, peaceful living in this 4 bedroom, 2.5 bathroom home in the Clifton Woods neighborhood. Beautiful inground pool surrounded by trees provides privacy for you and your family to enjoy swimming, and hanging out on the large patio deck overlooking the pool. Home has a first floor master bedroom and full bathroom. There is also a detached in-law suite on the property, that was being rented for $1,000/month. Also used as an Air BnB during the summer and for Iron Man events.

5609 Bayberry Way, Cambridge

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

$799,900
3 Beds ⋅ 2 Baths
Welcome to 3804 Robinson Neck Road, your secluded sanctuary nestled on Maryland's picturesque Eastern Shore. Whether you are an enthusiastic sportsman or simply seeking the ideal retreat, this property caters to a wide array of desires. Spanning approximately 5.85 acres along the serene St. Johns Creek, it offers breathtaking westerly views across the Chesapeake Bay and the iconic Calvert Cliffs. In 2022, a significant 1,200 square-foot addition was seamlessly integrated into the home, showcasing a magnificent great room with a soaring cathedral ceiling, a primary suite on the first floor, and a luxurious 15'x8' indoor swim spa. The kitchen, remodeled in 2023 features stainless steel appliances, recessed lighting, granite countertops, and a cozy wood stove insert. It opens into a charming breakfast room, an ideal spot to savor the stunning views. The original section of the house retains elements from its 1920s construction, adding a touch of historic charm. The inviting living room, adorned with wood floors and exposed beams, features another wood stove, creating a warm and welcoming ambiance. Upstairs, two bedrooms each offer captivating water views. The enclosed porch off the kitchen is another tranquil spot, perfect for observing deer and other wildlife gathering by the pond. Step outside, and the adventure begins! On the waterside, you'll find an L-shaped pier equipped with a 10,000-pound boat lift, a boat ramp for personal watercraft, canoes, kayaks, and paddleboards. The pier also includes a fish cleaning station, as well as water and electric hookups. A short boat ride brings you to the bay, where you can fish for drum, rockfish, flounder, and other native species, or cast a line and set a crab pot right from the pier. The deck offers panoramic views and breathtaking sunsets, while the protected waters of St. Johns Creek are perfect for canoeing, kayaking, and paddleboarding. Beyond the water, the property features a wooded area with two heated deer stands, making it a prime location for hunting Sika and Whitetail deer, turkey, and a variety of waterfowl. Additional amenities include a 21kW Generac generator, an outdoor shower with hot and cold water, a partially fenced and irrigated lawn, and a pole barn with 14-foot ceilings and 12-foot doors. A separate electric panel in the pole building supplies power to the pier, pond, and deer stands. Following Hurricane Isabelle in 2003, the original home was elevated and placed on a new foundation, with a new well installed in the same year and a new septic system in 2005. This unique property is truly a blend of modern comfort and rustic charm, ready to be your personal haven. Please do not enter lane or property without an appointment!

3804 Robinson Neck Rd, Taylors Island

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

$379,900
4 Beds ⋅ 3 Baths
Two years young and move-in ready 4BR/2.5BA Colonial located in the desirable community of Longboat Estates. Park just outside the attached two car garage, make your way past lush landscaping, and step up to the covered front entry into your forever home. Step into a home filled with tons of natural light, a two story entry hall, luxury flooring, and an open floor plan. The main floor offers a large dining room that opens to the kitchen, breakfast area, and family room. The family room boasts vaulted ceilings with a view of the second floor landing, and a gas fireplace surrounded by a stone facade. The kitchen is amazing, offering plenty of cabinets, a separate pantry closet, stainless steel appliances, and sleek quartz countertops. This home offers a main floor primary suite featuring a large walk-in closet, and private ensuite boasting a double sink vanity and walk-in shower. In addition to all this is a half bath, access to the two car garage, and laundry room. On the second floor are three large bedrooms and a full bath. From the breakfast room step through sliding doors onto a large wood deck that overlooks a yard filled with tons of green space and room for entertaining family and friends. This home is ideal for any new homeowner and offers an interior sprinkler system throughout, and is located in a community offering a community dock and inground pool. Imagine all this and in close proximity to shopping, restaurants, and commuter routes.

168 Regulator Dr N, Cambridge

Listing courtesy of VYBE Realty. Contact: 4102204648
$1,395,000
5 Beds ⋅ 5 Baths
Stunning Classic Greek Revival Architecture Home on Jenkins Creek, just minutes from Downtown Cambridge. Enter the extended blacktop lane off Horns Point Rd until you arrive at the circular drive of this beautifully appointed 5 Bedroom, 4 1/2 Bath, waterfront home with water views from almost every room. The home sits on 3.3+/- acres with approximately three miles of unobstructed water views, a 60'+/- pier with 3+/- water depth, and over 500’+/- of Shoreline on Jenkins Creek, a tributary of the Choptank River. This meticulously maintained turn of the century waterfront home has water views from every vantage point. Whether it's sitting around the pool or on the wrap around porch, there's nothing like watching the endless flow of wildlife from this property. The location of this home provides easy access either by boat or car to the many amenities the Shore has to offer. Go by land to the many resturants in Downtown Cambridge and the surrounding areas, as well as, go by boat to Cambridge, Oxford, Secretary, and Saint Michaels. If you love fishing and crabbing, leave your dock and within minutes you will be in the majestic Choptank River ready to fish and/or crab. You can also put a crab pot off the dock in the early AM and possibly have dinner before nighfall. The property has an oversized five car garage, as well as, storage for all your water toys! The oversized garage second floor is waiting for the new owners to make it their own. The Sellers are leaving the area, so many of the furnishing could be purchased separately with the sale of the home. Come check out this gem of a home, we think you will love it!

2208 Horns Point Road, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$259,900
2 Beds ⋅ 1 Baths
Nice 2 bedroom 1 bath farmhouse located on the edge of town. This home has 3 rooms that could be used as bedrooms but technically only 2 bedrooms. This serene property consists of 2 parcels, the main house is in the city limits and the other parcel is in the county. House has plenty of character and wood trim throughout. In ground pool with patio area that is great for entertaining with plenty of privacy. Garden area in the rear with a large workshop and an RV carport as well. This one will not last long!!

525 Academy St, Hurlock

Listing courtesy of McClain-Williamson Realty, LLC. Contact:

$434,888
4 Beds ⋅ 3 Baths
ONLY 2 HOMES REMAIN!!!! Longboat Estates provides the ideal community for residents looking for an incredible Chesapeake lifestyle in a lovely residential area of historic Cambridge, Maryland with water access. Longboat Estates community amenities include private use of a pool, boat ramp, and pier on Jenkins Creek. Located on the shores of the Choptank River, the idyllic town of Cambridge offers countless waterfront spots for picnics, meanderings, and time with friends and family. Proximity to great local dining, shopping, parks, waterways, and more make Longboat Estates a convenient place to call home. Come experience it for yourself! Offering close proximity to Route 50 and located halfway between the Chesapeake Bay Bridge and Ocean City, MD. Longboat Estates offers the opportunity to explore incredible nearby destinations, offering a truly unique living experience. This Bristol II stands proud with its classic colonial facade with a modern floor plan inside. The first floor features a formal Living Room and dining room that are large and designed with the potential for use beyond their intention. These rooms could be converted for use as an office, playroom, or library. Beyond that, to the rear of the home, the combined Great Room, Breakfast Room, and Kitchen space offer multiple windows and a glass sliding door that allows you to take in the backyard with the boundless potential for outdoor entertainment. The Kitchen features a plethora of cabinet and pantry space. The Great Room makes the perfect space for entertaining and spending time with family and friends. The second floor features a large Owner's Bedroom with a private ensuite bathroom with double vanity sinks that provides ample private space for partners. The Owner's Suite amenities include a large private walk-in and linen closet. The second floor also features 3 additional bedrooms and a laundry closet, centrally located for convenience and ease. Explore more of what this splendid home has to offer!

178 Regulator Drive North, Cambridge

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565
$179,500
3 Beds ⋅ 2 Baths
BACK TO ACTIVE WITH REDUCED PRICE. This property is nestled in the historic town of Vienna, MD, The location was first reported by by Capt. John Smith while sailing the adjoining Nanticoke River in 1608. The town settlement was created in 1706, and remnants of times gone by still exist. Vienna is superbly located with short commutes to Salisbury and Cambridge. less than an hour from ocean beaches, and Western Shore attractions are not too distant. Vienna's mainstay is the river, with 65+ miles of navigable water having abundant seafood and water sports to enjoy. On the Nanticoke in town are a public park, boat ramp and riverside boardwalk. 106 Market St is an ideal choice as to price and location for first time home buyers with children to raise. The house consists of a front hallway, living room, formal dining room , kitchen, laundry room with half bath on the main first level, and three bedrooms and full bath on the second level. The rear yard goes deep with mature trees, flower garden and large inground pool.

106 Market St, Vienna

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

$535,000
3 Beds ⋅ 3 Baths
Price Drop! Motivated Seller!! Excellent Opportunity! Visit Today!! Take a second look - recent improvements and the pool is open!! Indian Cove, Church Creek-experience exceptional Eastern Shore living! 6.13 +/- acres offering privacy and the opportunity to watch bald eagles, deer, osprey and other wildlife. Spectacular sunrises and sunsets! A Church Creek tributary running along the property offers a place to launch your kayaks, canoes and to fish and crab. The 3 bedroom, 2 1/2 bath home offers an upgraded granite kitchen with large center island and stainless appliances- 2 refrigerators and 2 dishwashers make entertaining a dream. Charming living room with wood floors. Game room. Tile bathrooms. New windows and new roof. Recent HVAC. The swimming pool boast a new liner and pump plus there is a pool house. New well pump. Paved driveway with at least 5 parking spaces. An additional building offers space for crafts, storage or whatever you can imagine. Large pole barn and room for pasture. A truly peaceful property - and just minutes from Cambridge!

1748 Taylors Island Rd, Woolford

Listing courtesy of Powell REALTORS. Contact:

$379,888
4 Beds ⋅ 3 Baths
ONLY 2 HOMES REMAIN!!! As you walk into the beautiful Roosevelt you are greeted by a large, welcoming foyer with an open formal living room and dining room to either side. The hallway flows to the rear of the home where you are met with an open floorplan of the kitchen, informal breakfast area, and an extensive Great Room. The Kitchen is spacious, allowing ease of mobility and allowing for it to be a comfortable gathering place. The first floor also features a powder room at the two-car garage entry and a hallway closet. The second floor includes the Owner's Suite, three additional bedrooms, a full bath, and a spacious laundry room. As you move through, The Owner's Suite is accessed by double doors to an open and expansive Owner's Bedroom. The Owner's Suite features two walk-in closets and an Owner's Bath. Longboat Estates provides the ideal community for residents looking for an incredible Chesapeake lifestyle in a lovely residential area of historic Cambridge, Maryland with water access. Longboat Estates community amenities include private use of a pool, boat ramp, and pier on Jenkins Creek. Located on the shores of the Choptank River, the idyllic town of Cambridge offers countless waterfront spots for picnics, meanderings, and time with friends and family. Proximity to great local dining, shopping, parks, waterways, and more make Longboat Estates a convenient place to call home. Come experience it for yourself! Offering close proximity to Route 50 and located halfway between the Chesapeake Bay Bridge and Ocean City, MD. Longboat Estates offers the opportunity to explore incredible nearby destinations, offering a truly unique living experience.

172 Regulator Drive North, Cambridge

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565
$425,000
5 Beds ⋅ 2 Baths
Welcome to 109 Mill Street...a classic example of a proudly-built 1918 home on one of the finest streets in historic Cambridge, Maryland! This 2,520 SF home, sited on .2790 acres, features beautiful hardwood floors throughout the spacious downstairs entertaining rooms as well as throughout the 4 second-floor bedrooms. The beautiful front room showcases a gracious staircase which leads to a lovely second floor landing, sparkling with afternoon sun. The library/study and dining room off the front room are large and well-lit and offer a versatile array of uses. The kitchen and utility room are located in the back of the house and are well-sized. The sun porch on the river side of the house is drenched in sunlight, while providing a "snug" gathering space for intimate conversations. The lovely back deck affords ample opportunity for outdoor entertaining, just 5 doors away from the banks of the mighty Choptank, yet not in the flood zone. There is an incredible "borrowed landscape opportunity" on this property as the specimen house to the left of 109 enjoys a bountiful lawn of 2.33 acres, providing a park-like atmosphere for the owners of 109 to enjoy but not to maintain. Conveniently located just 5 doors from the Cambridge Yacht Club and marina and a stone's throw from the historic downtown, residents can enjoy restaurants, pubs, shops and museums after a full day of sailing, fishing, hunting or playing tennis or pickle ball at nearby courts. Cambridge is enjoying a robust renaissance after having held the spot as the second most prosperous city in Maryland in 1900. Cambridge was second only to Baltimore in 1900 due to its deep water and long legacy of oystering, crabbing, fishing and canning enterprises. Please come join us and be a part of the exciting renaissance of this historically-significant eastern shore city!

109 Mill St, Cambridge

Listing courtesy of Compass. Contact: (301) 304-8444
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