Homes with Pools for Sale in Dukes County, MA

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ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcoming setting for enjoying the Vineyard lifestyle. The pool features a sun shelf and built-in seating and is surrounded by an expansive stone terrace with generous room for lounging and entertaining. Two pergola pavilions create a stylish open-air living area with dedicated lounge and dining spaces, while an outdoor show

$2,395,000

4 beds3 baths1,968 sq ft

105 Whalers Walk, Edgartown, MA 02539

Sun shelf • Built-in seating • Outdoor shower

OPEN WED, 10AM TO 12PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Katama at its best! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach, with the bike path, Katama General Store, and Edgartown Village close by, this updated, move-in-ready home puts the best of the Island within easy reach. A newly installed pool and expansive yard create a private setting for summer days and long afternoons outdoors. Inside, the kitchen features an inviting banquet dining area and opens to a spacious cathedral-ceilinged family room with sliders to the back deck, outdoor shower, pool, and yard. A separate liv

$3,075,000

3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

First-floor bedroom • Newly installed pool • Expansive yard

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up an

$2,200,000

4 beds3 baths3,771 sq ft

99 Oak Ln, West Tisbury, MA 02575

Private acres • Gunite swimming pool • Future expansion

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

$725,000

2 beds1 bath703 sq ft

124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568

Picnic tables • Common grounds • Walk to the ferry

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspir

$7,950,000

4 beds4.5 baths7,766 sq ft

2 Lexington Ave, Edgartown, MA 02539

Edible garden • Butler's pantry • Heated gunite pool

Property at 31 Josiah Sachem Way, West Tisbury, MA 02575, 7 beds, 4.5 baths

$4,125,000

7 beds4.5 baths3,313 sq ft

31 Josiah Sachem Way, West Tisbury, MA 02575

Property at 10 & 12 Boldwater Rd, Edgartown, MA 02539, 11 beds, 12 baths

$14,500,000

11 beds12 baths9,500 sq ft

10 & 12 Boldwater Rd, Edgartown, MA 02539

Property at 18 Point Inner Way, Chilmark, MA 02535, 7 beds, 12 baths

$45,000,000

7 beds12 baths11,200 sq ft

18 Point Inner Way, Chilmark, MA 02535

Property at 56 North Summer St, Edgartown, MA 02539, 10 beds, 12.5 baths

$21,500,000

10 beds12.5 baths7,598 sq ft

56 North Summer St, Edgartown, MA 02539

Property at 29 Slough Cove Rd, Edgartown, MA 02539, 4 beds, 5 baths

$9,495,000

4 beds5 baths4,605 sq ft

29 Slough Cove Rd, Edgartown, MA 02539

Property at 131 North Water St-huxford Cottage #96, Edgartown, MA 02539, 3 beds, 3 baths

$2,875,000

3 beds3 baths1,061 sq ft

131 North Water St-huxford Cottage #96, Edgartown, MA 02539

Property at 7 Katama Dr, Edgartown, MA 02539, 3 beds, 3.5 baths

$5,795,000

3 beds3.5 baths3,116 sq ft

7 Katama Dr, Edgartown, MA 02539

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 131 North Water St-huxford Cottage #94, Edgartown, MA 02539, 2 beds, 2 baths

$1,975,000

2 beds2 baths730 sq ft

131 North Water St-huxford Cottage #94, Edgartown, MA 02539

Property at 124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568, 2 beds, 1 bath

$550,000

2 beds1 bath725 sq ft

124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

Property at 131 North Water St-collins Cottage #22, Edgartown, MA 02539, 2 beds, 2 baths

$2,595,000

2 beds2 baths960 sq ft

131 North Water St-collins Cottage #22, Edgartown, MA 02539

Property at 8 Snail Rd, Chilmark, MA 02535, 6 beds, 8 baths

$15,400,000

6 beds8 baths6,967 sq ft

8 Snail Rd, Chilmark, MA 02535

Property at 9 Thaxter Ln, Edgartown, MA 02539, 3 beds, 3.5 baths

$3,695,000

3 beds3.5 baths3,056 sq ft

9 Thaxter Ln, Edgartown, MA 02539

Property at 131 North Water St -rowley Cottage #62, Edgartown, MA 02539, 2 beds, 2 baths

$2,425,000

2 beds2 baths895 sq ft

131 North Water St -rowley Cottage #62, Edgartown, MA 02539

Property at 43 Peases Point Way S, Edgartown, MA 02539, 4 beds, 6 baths

$9,000,000

4 beds6 baths5,902 sq ft

43 Peases Point Way S, Edgartown, MA 02539

Property at 114 North Water St, Edgartown, MA 02539, 8 beds, 7.5 baths

$16,900,000

8 beds7.5 baths6,041 sq ft

114 North Water St, Edgartown, MA 02539

Property at 31 Lambert's Cove Rd, Vineyard Haven, MA 02568, 6 beds, 7.5 baths

$5,800,000

6 beds7.5 baths5,732 sq ft

31 Lambert's Cove Rd, Vineyard Haven, MA 02568

Property at 58 Road To The Plns, Edgartown, MA 02539, 4 beds, 2 baths

$1,625,000

4 beds2 baths1,342 sq ft

58 Road To The Plns, Edgartown, MA 02539

Property at 261 Sandpiper Ln #12, Tisbury, MA 02539, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,682 sq ft

261 Sandpiper Ln #12, Tisbury, MA 02539

Property at 20 James Pond Way, West Tisbury, MA 02575, 5 beds, 3 baths

$3,600,000

5 beds3 baths2,701 sq ft

20 James Pond Way, West Tisbury, MA 02575

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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 Tue Aug 25 2026. 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. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Pools for Sale in Dukes County

There are currently 25 homes with pools for sale in Dukes County at a median listing price of $2.4M. 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 74 days. This map is refreshed with the newest listings in Dukes County every 15 minutes.

In the past month, 9 homes have been sold in Dukes County. In addition to houses in Dukes County, there were also 12 condos, 1 townhouse, and 3 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.

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Homes with Pools for Sale in Dukes County, MA

Homes with Pools for Sale in Dukes County

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