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:
Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J. G. Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite. The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additio

$8,900,000

8 beds8 baths8,560 sq ft

150 East Chop Dr, Oak Bluffs, MA 02557

0.64 acre lot • 2 garage spots • Built 2017

OPEN SUN, 11AM TO 1PM

$1,099,000

4 beds2 baths1,306 sq ft

113 Leonard Cir, Vineyard Haven, MA 02568

0.23 acre lot • 4 parking spots • Built 1997

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious p

$2,400,000

3 beds3.5 baths1,883 sq ft

27 7th St, Edgartown, MA 02539

New construction • Bosch appliances • Gas fireplace

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Experience the quintessential Martha's Vineyard lifestyle at this charming residence nestled in a private, convenient Katama location. This inviting 3 BR plus loft, 2 BA home is on a . 52-acre lot, providing ample privacy and outdoor enjoyment. Step inside the light-filled interior featuring multiple windows and skylights that invite the sunshine in. Convenience is key with two well-appointed bathrooms inside, plus the highly coveted outdoor shower, perfect for rinsing off after a day at the beach! Savor the peace and tranquility of a very private spot, yet enjoy the convenience of being just 1.5 miles from the charming center of Edgartown with its picturesque harbor, vibrant shops, and del

$1,950,000

3 beds2 baths2,238 sq ft

10 Duende Ln, Edgartown, MA 02539

Outdoor shower • Private location • 0.52 acre lot

ABOUT THIS HOME
Home with a Pool for sale in Dukes County, MA:
Katama ~ Turnkey Retreat in Edgartown Estates. Located on a quiet, paved road in sought-after Edgartown Estates, this meticulously maintained home offers the perfect blend of privacy, space, and convenience. Ideally positioned equidistant to South Beach and downtown Edgartown, and just moments from the bike path. The home features a bright vaulted-ceiling living room with a gas fireplace and an open eat-in kitchen that leads seamlessly to a spacious back deck. Don’t miss the fabulous outdoor shower, a true Vineyard essential. The first-floor primary suite offers privacy and ease with cathedral ceilings, a walk-in closet, and an en-suite bath. Upstairs, two large bedrooms with generous

$2,490,000

3 beds3 baths2,830 sq ft

42 Deacon Vincent Way, Edgartown, MA 02539

Open eat in kitchen • Quiet paved road • Gas fireplace

Property at 111 Charles Neck Way, West Tisbury, MA 02575, 3 beds, 2 baths

$1,599,000

3 beds2 baths1,562 sq ft

111 Charles Neck Way, West Tisbury, MA 02575

Property at 50 Lantern Ln, Vineyard Haven, MA 02568, 3 beds, 1.5 baths

$1,193,000

3 beds1.5 baths1,040 sq ft

50 Lantern Ln, Vineyard Haven, MA 02568

Property at 40 Scotchmans Ln, West Tisbury, MA 02575, 4 beds, 2 baths

$1,495,000

4 beds2 baths1,332 sq ft

40 Scotchmans Ln, West Tisbury, MA 02575

Property at 76 Washque Ave, Edgartown, MA 02539, 4 beds, 2.5 baths

$2,575,000

4 beds2.5 baths1,910 sq ft

76 Washque Ave, Edgartown, MA 02539

Property at 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 3 beds, 3 baths

$2,150,000

3 beds3 baths1,680 sq ft

33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Property at 25 Lelands Path, Edgartown, MA 02539, 6 beds, 7.5 baths

$9,995,000

6 beds7.5 baths7,205 sq ft

25 Lelands Path, Edgartown, MA 02539

Property at 70 Carol Ln, Oak Bluffs, MA 02557, 2 beds, 2.5 baths

$1,200,000

2 beds2.5 baths1,500 sq ft

70 Carol Ln, Oak Bluffs, MA 02557

Property at 174 Middle Road Rd, Chilmark, MA 02535, 4 beds, 3.5 baths

$1,895,000

4 beds3.5 baths2,061 sq ft

174 Middle Road Rd, Chilmark, MA 02535

Property at 31 Lamberts Cove Rd, Vineyard Haven, MA 02568, 6 beds, 7.5 baths

$6,250,000

6 beds7.5 baths5,732 sq ft

31 Lamberts Cove Rd, Vineyard Haven, MA 02568

Property at 6 Janes Cove Rd, Edgartown, MA 02539, 6 beds, 6.5 baths

$8,250,000

6 beds6.5 baths6,927 sq ft

6 Janes Cove Rd, Edgartown, MA 02539

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

$5,325,000

6 beds4 baths2,890 sq ft

4 Canonicus Ave, Oak Bluffs, MA 02557

Property at 15 Old Farm Rd, Chilmark, MA 02535, 3 beds, 5 baths

$4,250,000

3 beds5 baths3,171 sq ft

15 Old Farm Rd, Chilmark, MA 02535

Property at 47 Winemack St, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,199,000

2 beds1 bath742 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Property at 1/3/5 Louis Field Rd, Edgartown, MA 02539, 11 beds, 8.5 baths

$8,995,000

11 beds8.5 baths6,289 sq ft

1/3/5 Louis Field Rd, Edgartown, MA 02539

Property at 108 Bay View Ave, Edgartown, MA 02539, 2 beds, 0.5 baths

$1,700,000

2 beds0.5 baths601 sq ft

108 Bay View Ave, Edgartown, MA 02539

Property at 14 Trapps Pond Rd, Edgartown, MA 02539, 7 beds, 7 baths

$10,850,000

7 beds7 baths12,051 sq ft

14 Trapps Pond Rd, Edgartown, MA 02539

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

$599,000

2 beds1 bath725 sq ft

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

Property at 157 Ben Chase Rd, West Tisbury, MA 02575, 4 beds, 2.5 baths

$2,250,000

4 beds2.5 baths2,982 sq ft

157 Ben Chase Rd, West Tisbury, MA 02575

Property at 71 Sixth St N, Edgartown, MA 02539, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths2,236 sq ft

71 Sixth St N, Edgartown, MA 02539

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

$1,750,000

4 beds2 baths1,342 sq ft

58 Road to The Plns, Edgartown, MA 02539

Property at 8 Old Purchase Way, Edgartown, MA 02539, 4 beds, 2.5 baths

$2,150,000

4 beds2.5 baths2,547 sq ft

8 Old Purchase Way, Edgartown, MA 02539

Property at 15 Tamarack Ln, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$4,999,000

6 beds5.5 baths3,214 sq ft

15 Tamarack Ln, Oak Bluffs, MA 02557

Property at 71 Stoney Hill Road Rd, Vineyard Haven, MA 02568, 5 beds, 5 baths

$4,500,000

5 beds5 baths5,598 sq ft

71 Stoney Hill Road Rd, Vineyard Haven, MA 02568

Property at 33 Goethals Way, Vineyard Haven, MA 02568, 5 beds, 2.5 baths

$12,500,000

5 beds2.5 baths2,794 sq ft

33 Goethals Way, Vineyard Haven, MA 02568

Property at 5 Pinetree Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,999,999

4 beds3 baths2,730 sq ft

5 Pinetree Ln, Vineyard Haven, MA 02568

Property at 16 Atlantic Ave, Oak Bluffs, MA 02557, 5 beds, 2.5 baths

$2,495,000

5 beds2.5 baths2,577 sq ft

16 Atlantic Ave, Oak Bluffs, MA 02557

Property at 139 Main St, Vineyard Haven, MA 02568, 5 beds, 6.5 baths

$3,750,000

5 beds6.5 baths4,372 sq ft

139 Main St, Vineyard Haven, MA 02568

Property at 12 & 14 Maple Ave, Oak Bluffs, MA 02557, 4 beds, 4 baths

$1,830,000

4 beds4 baths1,600 sq ft

12 & 14 Maple Ave, Oak Bluffs, MA 02557

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

$9,499,000

4 beds6 baths5,458 sq ft

43 Peases Point Way S, Edgartown, MA 02539

Property at 108 Bay Vw, Edgartown, MA 02539, 2 beds, 0.5 baths

$1,700,000

2 beds0.5 baths601 sq ft

108 Bay Vw, Edgartown, MA 02539

Property at 21 Woodlawn Ave, Vineyard Haven, MA 02568, 4 beds, 3 baths

$2,495,000

4 beds3 baths2,562 sq ft

21 Woodlawn Ave, Vineyard Haven, MA 02568

Property at 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535, 5 beds, 4.5 baths

$4,950,000

5 beds4.5 baths3,413 sq ft

124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

Property at 68 N Water St, Edgartown, MA 02539, 6 beds, 7.5 baths

$15,500,000

6 beds7.5 baths1,320 sq ft

68 N Water St, Edgartown, MA 02539

Property at 7 Upper Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$1,850,000

4 beds2.5 baths3,268 sq ft

7 Upper Meadow Ln, Oak Bluffs, MA 02557

Property at 96 Hammett Ln, Chilmark, MA 02535, 3 beds, 3 baths

$3,995,000

3 beds3 baths3,426 sq ft

96 Hammett Ln, Chilmark, MA 02535

Property at 5 Pip'n Rd, Edgartown, MA 02539, 3 beds, 2 baths

$1,395,000

3 beds2 baths1,800 sq ft

5 Pip'n Rd, Edgartown, MA 02539

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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 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.

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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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