Homes with Pools for Sale in Dukes County, MA

137 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Perched on 2.7 acres in one of Aquinnah’s most stunning settings, this coastal retreat captures sweeping views over the Atlantic and Noman’s Land. The main level offers an open living/dining/kitchen wrapped in windows and opening to a wraparound mahogany deck—ideal for sunrise coffee and sunset dinners. A Viking-equipped kitchen and a spacious ocean-facing primary suite complete this floor. The lower level includes two bedrooms, a large flex room with walkout stone patio, plus a full bath, laundry, and storage. Beautiful grounds feature custom stonework, garden beds, and multiple outdoor seating areas. A two-level workshop/studio with plumbing, electricity, and a wood stov

$3,350,000

3 beds2.5 baths2,686 sq ft

4 Noman's Watch Rd, Aquinnah, MA 02535

Garden beds • Custom stonework • Walkout stone patio

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and abundant natural light throughout, this move-in-ready home blends comfort and style. Ideal for year-round living or seasonal retreat.

$1,095,000

3 beds1.5 baths1,487 sq ft

12 Wheelhouse Way, Oak Bluffs, MA 02557

8,861 sq ft lot • Built 1999 • Listed 24 days

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining room. The kitchen is at the back of the house with the mudroom and side entrance beyond. Enjoy the beautiful natural light in the spacious sun room at the front of the house with French doors leading to the side yard. The property offers charm and potential in a sought-after location. Several updates w

$875,000

2 beds1 bath861 sq ft

24 School St, Oak Bluffs, MA 02557

Spacious sun room • 0.24 acre lot • Garage

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Country Living so close to Town! Lovely 3 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. Living Room with additional nook. Half bath. Interior stairs to lower level with private exterior entrance and garage. 2nd floor has large primary bedroom with cathedral ceilings, walk through double closet and generous private bath with jacuzzi, separate shower and laundry facilities. Two additional bedrooms. two full baths. Attic. Grassy areas on front and side of property. Small association off West Spring St. R10 Zoning. Propane FHW Heat Pump A/C Radiant Heat on lower level Town Water , T

$1,495,000

3 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Large side deck • Cathedral ceilings • Jacuzzi

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
West Tisbury Farmhouse with all of the Historic Charm! 1743/1850, once owned by the renowned sailor & author Joshua Slocum. Located on a lush 1.27 acres, this property has all the makings of a perfect family compound with a 4 bedroom, 2 Bathroom Main House and a 1 Bedroom, 1 Bathroom Guest Cottage. From the patio entry you will arrive into the bright, custom kitchen with new appliances, vaulted ceilings, a generous center island and sizable Verona gas range. Enjoy plenty of work space and additional storage in the walk-in pantry. From there the kitchen then opens up to the dining area and additional sitting area, with exposed beams, period plaster walls, wide wooden floorboards and on

$1,892,500

5 beds3 baths2,552 sq ft

10 Dan'ls Way, West Tisbury, MA 02575

Custom kitchen • Period plaster walls • New appliances

Property at 51 Lantern Ln, Vineyard Haven, MA 02568, 2 beds, 1 bath

$835,000

2 beds1 bath768 sq ft

51 Lantern Ln, Vineyard Haven, MA 02568

Property at 7 South Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 3 baths

$1,825,000

4 beds3 baths3,142 sq ft

7 South Meadow Ln, Oak Bluffs, MA 02557

Property at 22 Old Lighthouse Rd, Vineyard Haven, MA 02568, 5 beds, 3 baths

$1,650,000

5 beds3 baths1,811 sq ft

22 Old Lighthouse Rd, Vineyard Haven, MA 02568

Property at 25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575, 2 beds, 2 baths

$1,100,000

2 beds2 baths1,583 sq ft

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Property at 2 Lincoln Ave, Oak Bluffs, MA 02557, 1 bed, 1 bath

$640,000

1 bed1 bath354 sq ft

2 Lincoln Ave, Oak Bluffs, MA 02557

Property at 18 Spruce Gate Rd, Chilmark, MA 02535, 5 beds, 3.5 baths

$12,500,000

5 beds3.5 baths3,700 sq ft

18 Spruce Gate Rd, Chilmark, MA 02535

Property at 47 Tiffany Dr, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$2,499,000

4 beds2.5 baths2,544 sq ft

47 Tiffany Dr, Oak Bluffs, MA 02557

Property at 10 Dory Cir, Edgartown, MA 02539, 4 beds, 3 baths

$1,600,000

4 beds3 baths1,738 sq ft

10 Dory Cir, Edgartown, MA 02539

Property at 400 Barnes Rd, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$6,395,000

6 beds5.5 baths7,000 sq ft

400 Barnes Rd, Oak Bluffs, MA 02557

Property at 344 Greenwood Ave, Vineyard Haven, MA 02568, 4 beds, 2 baths

$1,300,000

4 beds2 baths1,566 sq ft

344 Greenwood Ave, Vineyard Haven, MA 02568

Property at 14 Twenty First St N, Edgartown, MA 02539, 3 beds, 1.5 baths

$1,200,000

3 beds1.5 baths1 sq ft

14 Twenty First St N, Edgartown, MA 02539

Property at 151 Tashmoo Ave, Tisbury, MA 02468, 4 beds, 3.5 baths

$2,295,000

4 beds3.5 baths2,690 sq ft

151 Tashmoo Ave, Tisbury, MA 02468

Property at 1 Saddle Club Rd, Edgartown, MA 02539, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths1,822 sq ft

1 Saddle Club Rd, Edgartown, MA 02539

Property at 67 12th St S, Edgartown, MA 02539, 3 beds, 1 bath

$969,000

3 beds1 bath960 sq ft

67 12th St S, Edgartown, MA 02539

Property at 35 Double Ox Rd, Oak Bluffs, MA 02557, 3 beds, 3.5 baths

$2,250,000

3 beds3.5 baths2,475 sq ft

35 Double Ox Rd, Oak Bluffs, MA 02557

Property at 825 Main St, Vineyard Haven, MA 02568, 6 beds, 5 baths

$14,500,000

6 beds5 baths5,867 sq ft

825 Main St, Vineyard Haven, MA 02568

Property at 61 Butlers Cove Rd, Edgartown, MA 02539, 9 beds, 10 baths

$33,000,000

9 beds10 baths7,190 sq ft

61 Butlers Cove Rd, Edgartown, MA 02539

Property at 2 Lincoln Ave Ave, Oak Bluffs, MA 02557, 1 bath

$640,000

0 beds1 bath354 sq ft

2 Lincoln Ave Ave, Oak Bluffs, MA 02557

Property at 50 Canonicus Ave, Oak Bluffs, MA 02557, 2 beds, 0.5 baths

$970,000

2 beds0.5 baths953 sq ft

50 Canonicus Ave, Oak Bluffs, MA 02557

Property at 27 Chapde Ln, Vineyard Haven, MA 02568, 3 beds, 2.5 baths

$1,615,000

3 beds2.5 baths1,740 sq ft

27 Chapde Ln, Vineyard Haven, MA 02568

Property at 187 Lagoon Pond Rd, Tisbury, MA 02575, 5 beds, 2 baths

$2,825,000

5 beds2 baths2,386 sq ft

187 Lagoon Pond Rd, Tisbury, MA 02575

Property at 34 Davis St, Vineyard Haven, MA 02568, 3 beds, 3.5 baths

$2,195,000

3 beds3.5 baths2,453 sq ft

34 Davis St, Vineyard Haven, MA 02568

Property at 52 S Summer Street South, Edgartown, MA 02539, 6 beds, 6 baths

$9,795,000

6 beds6 baths6,135 sq ft

52 S Summer Street South, Edgartown, MA 02539

Property at 7 Clay Pit Ln, Aquinnah, MA 02535, 5 beds, 4.5 baths

$7,450,000

5 beds4.5 baths5,000 sq ft

7 Clay Pit Ln, Aquinnah, MA 02535

Property at 128 Spring St, Vineyard Haven, MA 02568, 5 beds, 3.5 baths

$1,575,000

5 beds3.5 baths2,436 sq ft

128 Spring St, Vineyard Haven, MA 02568

Property at 136 Spring St, Vineyard Haven, MA 02568, 1 bed, 1 bath

$850,000

1 bed1 bath534 sq ft

136 Spring St, Vineyard Haven, MA 02568

Property at 46 Tercel Ln, Chilmark, MA 02535, 2 beds, 1 bath

$1,650,000

2 beds1 bath716 sq ft

46 Tercel Ln, Chilmark, MA 02535

Property at 8 Paddock Rd, Oak Bluffs, MA 02557, 4 beds, 5.5 baths

$5,450,000

4 beds5.5 baths3,300 sq ft

8 Paddock Rd, Oak Bluffs, MA 02557

Property at 46 Tiercel Ln, Chilmark, MA 02535, 2 beds, 1 bath

$1,650,000

2 beds1 bath716 sq ft

46 Tiercel Ln, Chilmark, MA 02535

Property at 24 Katama Bay View Rd, Edgartown, MA 02539, 4 beds, 5 baths

$8,500,000

4 beds5 baths3,497 sq ft

24 Katama Bay View Rd, Edgartown, MA 02539

Property at 124 Skiff Ave Unit D10, Vineyard Haven, MA 02568, 3 beds, 2 baths

$725,000

3 beds2 baths1,356 sq ft

124 Skiff Ave Unit D10, Vineyard Haven, MA 02568

Property at 56 N Neck Rd, Edgartown, MA 02539, 4 beds, 3 baths

$3,995,000

4 beds3 baths4,920 sq ft

56 N Neck Rd, Edgartown, MA 02539

Property at 159 Lake St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,595,000

5 beds4 baths3,329 sq ft

159 Lake St, Vineyard Haven, MA 02568

Property at 9 Brunswick Ave, Oak Bluffs, MA 02557, 3 beds, 1 bath

$1,449,000

3 beds1 bath1,033 sq ft

9 Brunswick Ave, Oak Bluffs, MA 02557

Property at 6 Brewster Ave, Oak Bluffs, MA 02557, 4 beds, 3 baths

$3,250,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Property at 60 -R Carol Ln, Oak Bluffs, MA 02557, 2 beds, 1 bath

$799,000

2 beds1 bath624 sq ft

60 -R Carol Ln, Oak Bluffs, MA 02557

Viewing page 1 of 4

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Wed Dec 03 2025. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Pools for Sale in Dukes County

There are currently 137 homes with pools for sale in Dukes County at a median listing price of $2.19M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dukes County stay on the market for 126 days. This map is refreshed with the newest listings in Dukes County every 15 minutes.

In the past month, 13 homes have been sold in Dukes County. In addition to houses in Dukes County, there were also 10 condos, 2 townhouses, and 6 multi-family units for sale in Dukes County last month. Find your dream home in Dukes 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 Dukes County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dukes County. If you're looking to sell your home in the Dukes County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dukes 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 Dukes County, MA

More to explore in Dukes County, MA

How to buy a house in Dukes County, MA

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 Massachusetts

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 Dukes County, MA

Homes with Pools for Sale in Dukes County

More real estate resources for Dukes County, MA

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Dukes County, MA

How to buy a house in Dukes County, MA

Popular Markets in Massachusetts