Homes with Pools for Sale in Dorchester County, MD

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ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Charming country rancher on 1.33 acres! Welcome to this fully remodeled home (2025) nestled at the end of a cul‑de‑sac surrounded by mature trees. Enjoy increased living space with the addition of a bedroom and bathroom for a total of 4BR and 2BA, plus a spacious laundry room and a separate dining area. Features LVP flooring throughout, modernized kitchen with plenty of cabinet space, and a storage shed in the back yard. You'll want to see all that this lovely, move-in ready home has to offer!!

$349,900

4 beds2 baths1,700 sq ft

6006 Corey Way, Hurlock, MD 21643

Fully remodeled home • Modernized kitchen • Storage shed

(302) 629-4514

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Welcome to 127 N Regulator Drive — a bright and inviting 4 bedroom, 3 bath home nestled in a sought-after waterfront community with access to a neighborhood pool and amenities. This home offers a spacious first-floor primary suite, an additional main-level bedroom or office, and two generously sized bedrooms upstairs — perfect for family, guests, or flex space. The main level features an open floorplan with hardwood floors throughout the living, dining, kitchen, and sunroom areas, creating a warm and cohesive feel. Enjoy outdoor living on the recently added bi-level deck overlooking the nicely landscaped yard. Amenities include pool, community dock, and boat ramp.

$425,000

4 beds3 baths2,927 sq ft

127 Regulator Dr N, Cambridge, MD 21613

Main-level bedroom • Open floorplan • Waterfront community

(410) 822-6665

READY TO BUILD

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Welcome to Pine Top Village-where small-town charm meets modern comfort. Discover spacious single-family homes and 1+ acre homesites, all tucked in the heart of Hurlock, MD. With top-rated schools nearby and everyday conveniences just a short drive away in Easton and Cambridge, Pine Top Village offers the perfect blend of space, value, and Eastern Shore living. Discover all the style you desire inside The Dogwood. A beautiful great room invites friends and family to gather. The adjoining gourmet kitchen features an optional island for added counter space. Add a half bath to the main level for extra convenience. Upstairs, your luxurious owner's suite includes a private en suite with an optio

$299,990

3 beds2 baths1,307 sq ft

Dogwood Plan, Hurlock, MD 21643

Gourmet kitchen • Half bath main level • 1 acre homesites

Listing provided by Zillow

READY TO BUILD

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Welcome to Pine Top Village-where small-town charm meets modern comfort. Discover spacious single-family homes and 1+ acre homesites, all tucked in the heart of Hurlock, MD. With top-rated schools nearby and everyday conveniences just a short drive away in Easton and Cambridge, Pine Top Village offers the perfect blend of space, value, and Eastern Shore living. The Hazel. This 2-car garage single-family home is highlighted by a large great room adjoining a gourmet kitchen with an island overlooking the dining area. Just off the garage, a first-floor guest suite means you don't have to sacrifice your flex room at the front of the home, which makes an ideal office or play space. Upstairs, thr

$379,990

5 beds3 baths2,541 sq ft

Hazel Plan, Hurlock, MD 21643

Gourmet kitchen • 1 acre homesites • Large great room

Listing provided by Zillow

READY TO BUILD

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Welcome to Pine Top Village-where small-town charm meets modern comfort. Discover spacious single-family homes and 1+ acre homesites, all tucked in the heart of Hurlock, MD. With top-rated schools nearby and everyday conveniences just a short drive away in Easton and Cambridge, Pine Top Village offers the perfect blend of space, value, and Eastern Shore living. The Fairview is a new two-story ranch design in the 30' Simply Ryan lineup, offering efficient, value-oriented features for buyers. It features an open-concept main level with abundant natural light, a convenient first-floor owner's suite, and a flexible second bedroom. The upper level includes a versatile loft and additional bedroom

$350,990

3 beds3 baths1,927 sq ft

Fairview Plan, Hurlock, MD 21643

1 acre homesites • 2 parking spots • Listed 53 days

Listing provided by Zillow

Property at 900 Marshy Cv #401, Cambridge, MD 21613, 2 beds, 2 baths

$219,999

2 beds2 baths— sq ft

900 Marshy Cv #401, Cambridge, MD 21613

(410) 221-8000

Property at 405 Leonards Ln, Cambridge, MD 21613, 4 beds, 2 baths

$234,000

4 beds2 baths1,608 sq ft

405 Leonards Ln, Cambridge, MD 21613

(410) 271-1265

Property at 2631 Rebecca Ln, Cambridge, MD 21613, 3 beds, 2 baths

$119,500

3 beds2 baths1,456 sq ft

2631 Rebecca Ln, Cambridge, MD 21613

(410) 745-0415

Property at 4445 Rolling Acres Dr, Hurlock, MD 21643, 3 beds, 2.5 baths

$345,000

3 beds2.5 baths1,606 sq ft

4445 Rolling Acres Dr, Hurlock, MD 21643

(410) 770-3600

Property at Marsh Elder Dr #51, Cambridge, MD 21613, 4 beds, 3 baths

$509,990

4 beds3 baths1,816 sq ft

Marsh Elder Dr #51, Cambridge, MD 21613

Listing provided by Zillow

Property at Marsh Elder Dr #68, Cambridge, MD 21613, 4 beds, 2.5 baths

$645,990

4 beds2.5 baths2,600 sq ft

Marsh Elder Dr #68, Cambridge, MD 21613

Listing provided by Zillow

Property at HOMESITE 68 Marsh Elder Rd, Cambridge, MD 21613, 4 beds, 2.5 baths

$645,990

4 beds2.5 baths2,600 sq ft

HOMESITE 68 Marsh Elder Rd, Cambridge, MD 21613

(240) 457-9391

Property at 178 Regulator Dr N, Cambridge, MD 21613, 4 beds, 2.5 baths

$399,999

4 beds2.5 baths2,220 sq ft

178 Regulator Dr N, Cambridge, MD 21613

(443) 225-9975

Property at HOMESITE 51 Marsh Elder Rd, Cambridge, MD 21613, 4 beds, 3 baths

$509,990

4 beds3 baths1,816 sq ft

HOMESITE 51 Marsh Elder Rd, Cambridge, MD 21613

(240) 457-9391

Property at 11 Shawnee Rd, Cambridge, MD 21613, 3 beds, 2.5 baths

$530,000

3 beds2.5 baths2,686 sq ft

11 Shawnee Rd, Cambridge, MD 21613

(410) 543-4545

Property at 128 Mariners Way, Cambridge, MD 21613, 4 beds, 2.5 baths

$300,000

4 beds2.5 baths1,903 sq ft

128 Mariners Way, Cambridge, MD 21613

(888) 838-9044

Property at 301 Old Squaw Ct, Cambridge, MD 21613, 3 beds, 2.5 baths

$228,000

3 beds2.5 baths1,960 sq ft

301 Old Squaw Ct, Cambridge, MD 21613

(410) 822-2152

Property at 1318 Bell Ln, Woolford, MD 21677, 3 beds, 2 baths

$875,000

3 beds2 baths2,120 sq ft

1318 Bell Ln, Woolford, MD 21677

(410) 673-3344

Property at 109 Gay St, Vienna, MD 21869, 2 beds, 1 bath

$224,900

2 beds1 bath1,615 sq ft

109 Gay St, Vienna, MD 21869

(855) 204-2400

Property at 4904 Ravenwood Rd, Vienna, MD 21869, 3 beds, 2 baths

$449,900

3 beds2 baths2,098 sq ft

4904 Ravenwood Rd, Vienna, MD 21869

(410) 822-6665

Property at 210 Race St, Vienna, MD 21869, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths1,440 sq ft

210 Race St, Vienna, MD 21869

(302) 539-1777

Property at 2189 Winterberry Ln, Cambridge, MD 21613, 3 beds, 2.5 baths

$259,990

3 beds2.5 baths1,762 sq ft

2189 Winterberry Ln, Cambridge, MD 21613

Listing provided by Zillow

Property at 123 Teal Ln, Cambridge, MD 21613, 4 beds, 2.5 baths

$369,900

4 beds2.5 baths2,994 sq ft

123 Teal Ln, Cambridge, MD 21613

(443) 225-9975

Property at 1301 Broadview Dr, Cambridge, MD 21613, 4 beds, 3.5 baths

$2,500,000

4 beds3.5 baths4,736 sq ft

1301 Broadview Dr, Cambridge, MD 21613

(410) 228-2525

Property at 610 Washington St, Cambridge, MD 21613, 3 beds, 2 baths

$125,000

3 beds2 baths1,088 sq ft

610 Washington St, Cambridge, MD 21613

(410) 228-2525

Property at 1005 Willowmere Ln, Cambridge, MD 21613, 3 beds, 2 baths

$274,900

3 beds2 baths1,504 sq ft

1005 Willowmere Ln, Cambridge, MD 21613

(443) 225-4100

Property at 1529 Deep Water Rd, Woolford, MD 21677, 4 beds, 2.5 baths

$480,000

4 beds2.5 baths2,072 sq ft

1529 Deep Water Rd, Woolford, MD 21677

(240) 456-0016

Property at 5332 Ragged Point Rd, Cambridge, MD 21613, 6 beds, 4.5 baths

$1,500,000

6 beds4.5 baths4,488 sq ft

5332 Ragged Point Rd, Cambridge, MD 21613

(410) 228-2525

Property at 3844 Wrights Wharf Rd, Hurlock, MD 21643, 3 beds, 2.5 baths

$399,900

3 beds2.5 baths2,016 sq ft

3844 Wrights Wharf Rd, Hurlock, MD 21643

(410) 228-9333

Property at 6132 Palmers Mill Rd, Hurlock, MD 21643, 3 beds, 2 baths

$399,900

3 beds2 baths1,404 sq ft

6132 Palmers Mill Rd, Hurlock, MD 21643

(410) 543-4545

Property at 11 Saddle Bill Cir, Cambridge, MD 21613, 4 beds, 2.5 baths

$349,990

4 beds2.5 baths2,198 sq ft

11 Saddle Bill Cir, Cambridge, MD 21613

(410) 260-2800

Property at Elder Plan, Dilokq Hurlock, MD 21643, 4 beds, 2.5 baths

$364,990

4 beds2.5 baths2,203 sq ft

Elder Plan, Dilokq Hurlock, MD 21643

Listing provided by Zillow

Property at 5751 Thompsontown, East New Market, MD 21631, 5 beds, 3 baths

$449,000

5 beds3 baths3,216 sq ft

5751 Thompsontown, East New Market, MD 21631

(410) 228-9333

Property at 5611 Galestown Rd, Seaford, MD 19973, 3 beds, 2 baths

$132,000

3 beds2 baths1,716 sq ft

5611 Galestown Rd, Seaford, MD 19973

(410) 228-2525

Property at 935 Susquehanna Rd, Madison, MD 21648, 3 beds, 2.5 baths

$305,000

3 beds2.5 baths2,512 sq ft

935 Susquehanna Rd, Madison, MD 21648

(443) 660-9229

Property at 2 Arbutus Ter, Cambridge, MD 21613, 3 beds, 2.5 baths

$329,900

3 beds2.5 baths1,677 sq ft

2 Arbutus Ter, Cambridge, MD 21613

(410) 228-2525

Property at 700 Cattail Cv #202, Cambridge, MD 21613, 2 beds, 2 baths

$199,000

2 beds2 baths— sq ft

700 Cattail Cv #202, Cambridge, MD 21613

(410) 871-2600

Property at 400 Robbins St, Cambridge, MD 21613, 3 beds, 2 baths

$160,000

3 beds2 baths1,248 sq ft

400 Robbins St, Cambridge, MD 21613

(410) 822-9000

Property at 131 Mariners Way, Cambridge, MD 21613, 3 beds, 2 baths

$320,000

3 beds2 baths1,272 sq ft

131 Mariners Way, Cambridge, MD 21613

(410) 479-3993

Property at 309 S Main St, Hurlock, MD 21643, 6 beds, 2 baths

$225,000

6 beds2 baths6,970 sq ft

309 S Main St, Hurlock, MD 21643

(410) 220-5745

Property at 112 Mariners Way, Cambridge, MD 21613, 5 beds, 2.5 baths

$390,000

5 beds2.5 baths2,226 sq ft

112 Mariners Way, Cambridge, MD 21613

(410) 228-9333

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Homes with Pools for Sale in Dorchester County

There are currently 311 homes with pools for sale in Dorchester County at a median listing price of $325K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dorchester County stay on the market for 85 days and receive 1 offers. This map is refreshed with the newest listings in Dorchester County every 15 minutes.

In the past month, 40 homes have been sold in Dorchester County. In addition to houses in Dorchester County, there were also 13 condos, 35 townhouses, and 3 multi-family units for sale in Dorchester County last month. Find your dream home in Dorchester County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Dorchester County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dorchester County. If you're looking to sell your home in the Dorchester County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dorchester County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Homes with Pools for Sale in Dorchester County, MD

Homes with Pools for Sale in Dorchester County

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