Homes with Pools for Sale in Dorchester County, MD

311 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Tired of searching for the perfect water-privileged home? Look no further! This newly listed brick rancher in Algonquin is your answer. Boasting a community pier, boat ramp, and trailer storage, enjoy seamless access to boating adventures on the Choptank River and beyond. For a quieter pace, paddleboard or kayak on Jenkins Creek's serene waters. Step inside to a home designed for both comfort and function. Hardwood floors lead to generous spaces, including a living room, dining room, and family room featuring a cozy brick fireplace right off the kitchen. Retreat to the primary suite, complete with a tiled full bathroom for ultimate convenience. The bright and airy sunroom and charming front

$345,000

3 beds2 baths1,780 sq ft

2 & 4 Algonquin Rd, Cambridge, MD 21613

Charming front porch • Trailer storage • Tiled full bathroom

(410) 228-2525

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Charming fully renovated 2 bedroom, 2 full bath home on nearly 1 acre on Hoopers Island. This spacious newly remodeled historic Hoopers Island home features new HVAC, kitchen and baths, new flooring and modern upgrades throughout. Large deep lot offers room for gardens, outdoor living and storage. Perfect as a year-round residence, weekend retreat or vacation rental - experience Hoopers Island lifestyle at its finest. Bring your bikes, golf cart - Hooper’s Island has it all - a general store, restaurant and bar, seafood houses for fresh catch and oysters, local stores, marinas, sport fishing, festivals, local music, the blackwater wildlife refuge close by! Crabbing, boating, kayaking,

$299,000

2 beds2 baths1,104 sq ft

2527 Old House Point Rd, Fishing Creek, MD 21634

0.78 acre lot • Garage • Built 1930

(410) 822-6272

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Cambridge - This beautiful home is situated on a corner lot in the Longboat Estates community. Soaring ceilings and hardwood floors offer a bright living space featuring a primary bedroom with bath on the first floor, an additional bedroom and full bath , living room with fireplace, study/office, dining room, family room and a sunroom. Large country kitchen. Lots of living space! The second floor features 2 huge bedrooms and a full bath, and storage areas. Attached garage. Brick front porch, plus back deck and patio area. Lots of upgrades. Custom built; one owner. Community pool and dock. The best of Eastern Shore living!

$439,900

4 beds3 baths3,772 sq ft

123 Regulator Dr, Cambridge, MD 21613

Study office • Corner lot • Hardwood floors

(410) 543-4545

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
Welcome to this recently built home in lovely Heron Point, where comfort and convenience unite! Step in to the wide open floor plan where gathering with friends and family comes easy. Whether hosting game night or preparing your fave dish in the bright, airy kitchen. Need some quiet time/work space, private OFFICE conveniently located on the main level. Upper level features spacious primary suite with walk in closets and 3 additional bedrooms where the walk ins continue. Plenty of natural light and comfortable design gives one a warm and welcome experience. Ready to head out? Enjoy morning coffee to evenings out, being just a few minutes from all the shops and eateries in charming downtow

$349,990

4 beds2.5 baths2,198 sq ft

11 Saddle Bill Cir, Cambridge, MD 21613

7,000 sq ft lot • 2 garage spots • Built 2023

(410) 260-2800

ABOUT THIS HOME
Home with a Pool for sale in Dorchester County, MD:
This is a lovely single-family home located on a nice corner lot.

$179,000

3 beds1 bath1,642 sq ft

201 Washington St, Cambridge, MD 21613

7,250 sq ft lot • Built 1920 • Listed 172 days

(410) 429-7425

Property at 5 Willis St, Cambridge, MD 21613, 3 beds, 2 baths

$309,000

3 beds2 baths1,863 sq ft

5 Willis St, Cambridge, MD 21613

(410) 822-1415

Property at 1826 Hoopersville, Fishing Creek, MD 21634, 2 beds, 2 baths

$870,000

2 beds2 baths1,200 sq ft

1826 Hoopersville, Fishing Creek, MD 21634

(410) 304-2011

Property at 601 Edlon Park Dr, Cambridge, MD 21613, 3 beds, 2.5 baths

$290,000

3 beds2.5 baths1,860 sq ft

601 Edlon Park Dr, Cambridge, MD 21613

(410) 271-1265

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 604 Edlon Park Dr, Cambridge, MD 21613, 4 beds, 2 baths

$327,500

4 beds2 baths2,426 sq ft

604 Edlon Park Dr, Cambridge, MD 21613

(410) 228-9333

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

Property at 401 N Main St, Hurlock, MD 21643, 6 beds, 4 baths

$390,000

6 beds4 baths3,854 sq ft

401 N Main St, Hurlock, MD 21643

(443) 992-4990

Property at 2197 Winterberry Ln, Cambridge, MD 21613, 3 beds, 2.5 baths

$318,940

3 beds2.5 baths1,762 sq ft

2197 Winterberry Ln, Cambridge, MD 21613

Listing provided by Zillow

Property at 2539 Old House Point Rd, Fishing Creek, MD 21634, 2 beds, 1.5 baths

$189,000

2 beds1.5 baths1,152 sq ft

2539 Old House Point Rd, Fishing Creek, MD 21634

(410) 673-3344

Property at Hazel Plan, Hurlock, MD 21643, 5 beds, 3 baths

$379,990

5 beds3 baths2,541 sq ft

Hazel Plan, Hurlock, MD 21643

Listing provided by Zillow

Property at 638 Douglas St, Cambridge, MD 21613, 4 beds, 2 baths

$230,000

4 beds2 baths1,942 sq ft

638 Douglas St, Cambridge, MD 21613

(443) 225-9975

Property at 3 Talbot Ave, Cambridge, MD 21613, 3 beds, 2 baths

$390,999

3 beds2 baths1,508 sq ft

3 Talbot Ave, Cambridge, MD 21613

(703) 242-0005

Property at 6802 Pine Bark Dr, Hurlock, MD 21643, 3 beds, 2 baths

$354,990

3 beds2 baths1,517 sq ft

6802 Pine Bark Dr, Hurlock, MD 21643

Listing provided by Zillow

Property at 26571 Line Rd, Seaford, DE 19973, 4 beds, 2.5 baths

$437,990

4 beds2.5 baths1,785 sq ft

26571 Line Rd, Seaford, DE 19973

(302) 360-0300

Property at 405 Osprey Cir, Cambridge, MD 21613, 4 beds, 2.5 baths

$349,000

4 beds2.5 baths2,032 sq ft

405 Osprey Cir, Cambridge, MD 21613

(410) 228-0800

Property at 1008 Phillips St, Cambridge, MD 21613, 3 beds, 1 bath

$110,000

3 beds1 bath976 sq ft

1008 Phillips St, Cambridge, MD 21613

(410) 228-2525

Property at 2700 Willow Oak Dr Unit 411B, Cambridge, MD 21613, 2 beds, 2 baths

$349,900

2 beds2 baths— sq ft

2700 Willow Oak Dr Unit 411B, Cambridge, MD 21613

(410) 822-6665

Property at Tupelo Plan, Zb9bn8 Hurlock, MD 21643, 3 beds, 2 baths

$329,990

3 beds2 baths1,517 sq ft

Tupelo Plan, Zb9bn8 Hurlock, MD 21643

Listing provided by Zillow

Property at 5302 River Dr, Cambridge, MD 21613, 3 beds, 2 baths

$324,900

3 beds2 baths1,491 sq ft

5302 River Dr, Cambridge, MD 21613

(410) 543-4545

Property at 408 Bayly Ave, Cambridge, MD 21613, 2 beds, 1 bath

$249,000

2 beds1 bath1,004 sq ft

408 Bayly Ave, Cambridge, MD 21613

(410) 429-7425

Property at 202 Muir St #202, Cambridge, MD 21613, 3 beds, 3.5 baths

$599,000

3 beds3.5 baths3,000 sq ft

202 Muir St #202, Cambridge, MD 21613

(703) 229-8935

Property at 9 Merryweather Dr, Cambridge, MD 21613, 4 beds, 2 baths

$364,900

4 beds2 baths1,748 sq ft

9 Merryweather Dr, Cambridge, MD 21613

(410) 543-4545

Property at 600 Red Bill Ln, Cambridge, MD 21613, 3 beds, 2.5 baths

$283,150

3 beds2.5 baths1,580 sq ft

600 Red Bill Ln, Cambridge, MD 21613

(410) 871-2600

Property at 900 Marshy Cv #103, Cambridge, MD 21613, 2 beds, 2 baths

$269,900

2 beds2 baths1,579 sq ft

900 Marshy Cv #103, Cambridge, MD 21613

(410) 721-0103

Property at 317 Shipyard Dr #67, Cambridge, MD 21613, 3 beds, 3 baths

$295,000

3 beds3 baths2,484 sq ft

317 Shipyard Dr #67, Cambridge, MD 21613

(855) 450-0442

Property at 101 Main St #119, Secretary, MD 21664, 3 beds, 2.5 baths

$345,000

3 beds2.5 baths— sq ft

101 Main St #119, Secretary, MD 21664

(301) 774-5900

Property at 2613 Hoopers Island Rd, Fishing Creek, MD 21634, 4 beds, 3 baths

$899,900

4 beds3 baths4,752 sq ft

2613 Hoopers Island Rd, Fishing Creek, MD 21634

(410) 864-5750

Property at 1609 Heliport Rd, Woolford, MD 21677

$337,900

— beds— baths— sq ft

1609 Heliport Rd, Woolford, MD 21677

(410) 677-0909

Property at 101 Thompson St, Hurlock, MD 21643, 3 beds, 2 baths

$339,000

3 beds2 baths— sq ft

101 Thompson St, Hurlock, MD 21643

(443) 358-0578

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 722 Glasgow St, Cambridge, MD 21613, 3 beds, 2 baths

$185,000

3 beds2 baths1,592 sq ft

722 Glasgow St, Cambridge, MD 21613

(410) 304-2011

Property at 1105 Holland Ave, Cambridge, MD 21613, 2 beds, 1 bath

$215,000

2 beds1 bath752 sq ft

1105 Holland Ave, Cambridge, MD 21613

(410) 822-6665

Property at 2 South Main St, East New Market, MD 21631, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,178 sq ft

2 South Main St, East New Market, MD 21631

(410) 228-9333

Property at 212 S Main St, Hurlock, MD 21643, 4 beds, 2 baths

$150,000

4 beds2 baths1,732 sq ft

212 S Main St, Hurlock, MD 21643

(410) 543-4545

Property at 6803 Pine Bark Dr, Hurlock, MD 21643, 4 beds, 2.5 baths

$338,990

4 beds2.5 baths1,658 sq ft

6803 Pine Bark Dr, Hurlock, MD 21643

Listing provided by Zillow

Property at 2700 Willow Oak Dr Unit 206D, Cambridge, MD 21613, 2 beds, 2 baths

$399,900

2 beds2 baths1,540 sq ft

2700 Willow Oak Dr Unit 206D, Cambridge, MD 21613

(410) 770-9255

Viewing page 5 of 8

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.

More real estate resources for Dorchester County, MD

More to explore in Dorchester County, MD

How to buy a house in Dorchester County, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Homes with Pools for Sale in Dorchester County, MD

Homes with Pools for Sale in Dorchester County

More real estate resources for Dorchester County, MD

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Dorchester County, MD

How to buy a house in Dorchester County, MD

Popular Markets in Maryland