Dukes County, MA homes for sale & real estate

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
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
Dukes County, MA Homes for Sale
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

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Tucked away in a private, beautifully landscaped setting, this charming Vineyard farmhouse offers a wonderful blend of privacy, space, and in-town convenience. Just moments from town, the ferry, and shopping, the four-bedroom, three-bath home sits on a spacious 30,000-square-foot lot with a five-bedroom septic system. Inside, sun-filled spaces, warm wood floors, built-ins, and a welcoming layout create an easy, comfortable feel. The first floor includes a private bedroom with en suite bath, while upstairs offers three additional bedrooms, two full baths, and laundry. The spacious living room opens to an enormous screened porch and back deck overlooking the beautifully landscaped yard--perfe

$2,250,000

4 beds3 baths1,938 sq ft

88 Franklin St, Vineyard Haven, MA 02568

Spacious back deck • Built in shelving • Charming window seat

FLOOR PLAN

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Set on over a half an acre in Edgartown’s desirable Island Grove neighborhood, this three-bedroom, two-bath classic Cape offers an exceptional expansion opportunity in a convenient Katama location. The existing 1,560-square-foot home can be enjoyed as-is while plans are developed for a renovation, expansion, or new construction. With a connection to town sewer, the property can support up to seven bedrooms, creating potential for a substantial residence, pool, and accessory dwelling unit. Association tennis courts are located nearby, with Edgartown Village, South Beach, shops, restaurants, and the harbor all within easy reach. A rare opportunity to create a custom Vineyard retreat in

$1,595,000

3 beds2 baths1,560 sq ft

9 Martha's Rd, Edgartown, MA 02539

0.59 acre lot • 4 parking spots • Built 1978

NEW CONSTRUCTIONFLOOR PLAN

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

$2,678,000

4 beds3.5 baths2,363 sq ft

31 Temahigan Ave, Oak Bluffs, MA 02557

0.27 acre lot • Built 2026 • Listed 6 days

Property at 59 Hagerty Dr, Vineyard Haven, MA 02568, 6 beds, 6 baths

$6,150,000

6 beds6 baths5,034 sq ft

59 Hagerty Dr, Vineyard Haven, MA 02568

Property at 49 The Blvd, Edgartown, MA 02539, 6 beds, 1 bath

$2,850,000

6 beds1 bath1,957 sq ft

49 The Blvd, Edgartown, MA 02539

Property at 27 Beach Rd, Oak Bluffs, MA 02557, 4 beds, 1.5 baths

$2,995,000

4 beds1.5 baths3,462 sq ft

27 Beach Rd, Oak Bluffs, MA 02557

Property at 41 Cook Rd, Vineyard Haven, MA 02568, 3 beds, 2.5 baths

$1,285,000

3 beds2.5 baths2,347 sq ft

41 Cook Rd, Vineyard Haven, MA 02568

Property at 2 Winemack St, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,095,000

3 beds2 baths2,173 sq ft

2 Winemack St, Oak Bluffs, MA 02557

Property at 99 Oak Ln, West Tisbury, MA 02575, 4 beds, 3 baths

$2,200,000

4 beds3 baths3,771 sq ft

99 Oak Ln, West Tisbury, MA 02575

Property at 9 Codman Spring Rd, Edgartown, MA 02539, 4 beds, 2.5 baths

$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

Property at Undisclosed address, Vineyard Haven, MA 02568, 3 beds, 2 baths

$1,895,000

3 beds2 baths1,864 sq ft

Undisclosed address, Vineyard Haven, MA 02568

Property at 139 Chappaquiddick Rd, Edgartown, MA 02539, 7 beds, 4 baths

$12,250,000

7 beds4 baths4,855 sq ft

139 Chappaquiddick Rd, Edgartown, MA 02539

Property at 11 Stanley St, Oak Bluffs, MA 02557, 3 beds, 1.5 baths

$1,255,000

3 beds1.5 baths912 sq ft

11 Stanley St, Oak Bluffs, MA 02557

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

$725,000

2 beds1 bath703 sq ft

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

Property at 36 Hines Point Rd, Vineyard Haven, MA 02568, 3 beds, 1 bath

$3,100,000

3 beds1 bath973 sq ft

36 Hines Point Rd, Vineyard Haven, MA 02568

Property at 8 Woodhaven Dr, Edgartown, MA 02539, 3 beds, 4.5 baths

$3,225,000

3 beds4.5 baths3,219 sq ft

8 Woodhaven Dr, Edgartown, MA 02539

Property at 174 Middle Rd, Chilmark, MA 02535, 3 beds, 3 baths

$1,695,000

3 beds3 baths3,702 sq ft

174 Middle Rd, Chilmark, MA 02535

Property at 25 Brickyard Rd, Chilmark, MA 02535, 6 beds, 7 baths

$16,250,000

6 beds7 baths8,648 sq ft

25 Brickyard Rd, Chilmark, MA 02535

Property at 149 Litchfield Rd, Edgartown, MA 02539, 3 beds, 4 baths

$4,725,000

3 beds4 baths2,969 sq ft

149 Litchfield Rd, Edgartown, MA 02539

Property at 8 Pip'n Cir, Edgartown, MA 02539, 3 beds, 2 baths

$1,500,000

3 beds2 baths1,717 sq ft

8 Pip'n Cir, Edgartown, MA 02539

Property at 43 Sengekontacket Rd, Oak Bluffs, MA 02557, 3 beds, 3 baths

$5,495,000

3 beds3 baths2,234 sq ft

43 Sengekontacket Rd, Oak Bluffs, MA 02557

Property at 59 Tuckernuck Ave, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$2,650,000

4 beds2.5 baths1,858 sq ft

59 Tuckernuck Ave, Oak Bluffs, MA 02557

Property at 528 Main St, Vineyard Haven, MA 02568, 4 beds, 4 baths

$1,800,000

4 beds4 baths2,670 sq ft

528 Main St, Vineyard Haven, MA 02568

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

$794,000

2 beds1 bath624 sq ft

60R Carol Ln, Oak Bluffs, MA 02557

Property at 2 Lexington Ave, Edgartown, MA 02539, 4 beds, 4.5 baths

$7,950,000

4 beds4.5 baths7,766 sq ft

2 Lexington Ave, Edgartown, MA 02539

Property at 323 County Rd, Oak Bluffs, MA 02557, 1 bed, 2 baths

$1,225,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

Property at 124 Main St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,695,000

5 beds4 baths2,374 sq ft

124 Main St, Vineyard Haven, MA 02568

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 29 Scotchmans Ln, West Tisbury, MA 02575, 2 beds, 2 baths

$1,350,000

2 beds2 baths1,996 sq ft

29 Scotchmans Ln, 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 30 Water Gate Rd, Vineyard Haven, MA 02568, 5 beds, 4.5 baths

$3,995,000

5 beds4.5 baths4,816 sq ft

30 Water Gate Rd, Vineyard Haven, MA 02568

Property at 44 Prices Way, Edgartown, MA 02539, 3 beds, 2 baths

$1,450,000

3 beds2 baths1,588 sq ft

44 Prices Way, Edgartown, MA 02539

Property at 150 Field View Ln, West Tisbury, MA 02575, 4 beds, 2.5 baths

$1,600,000

4 beds2.5 baths2,334 sq ft

150 Field View Ln, West Tisbury, MA 02575

Property at 21 & 25 Fulling Mill Rd, Chilmark, MA 02535, 4 beds, 3 baths

$2,250,000

4 beds3 baths1,918 sq ft

21 & 25 Fulling Mill Rd, Chilmark, MA 02535

Property at 135 Mayflower Ln, Vineyard Haven, MA 02568, 5 beds, 3 baths

$1,995,000

5 beds3 baths3,480 sq ft

135 Mayflower Ln, Vineyard Haven, MA 02568

Property at 26 Winthrop Ave, Oak Bluffs, MA 02557, 1 bed, 1 bath

$839,000

1 bed1 bath804 sq ft

26 Winthrop Ave, Oak Bluffs, MA 02557

Property at 41 Edgartown Rd, Vineyard Haven, MA 02568, 5 beds, 2 baths

$1,399,000

5 beds2 baths1,968 sq ft

41 Edgartown Rd, Vineyard Haven, MA 02568

Property at 205 Meetinghouse Way, Edgartown, MA 02539, 3 beds, 3 baths

$2,700,000

3 beds3 baths2,844 sq ft

205 Meetinghouse Way, 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

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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.

Average home prices near Dukes County, MA

Cities

Chilmark homes for sale
$3,795,000
Oak Bluffs homes for sale
$1,255,000
Woods Hole homes for sale
$2,150,000
West Tisbury homes for sale
$1,800,000
Vineyard Haven homes for sale
$1,800,000
Edgartown homes for sale
$2,875,000
Tisbury homes for sale
$1,895,000
Aquinnah homes for sale
$5,000,000
Oak Bluffs homes for sale
$1,800,000
Falmouth homes for sale
$950,000

Counties

Plymouth County homes for sale
$729,950
Barnstable County homes for sale
$899,000
Bristol County homes for sale
$589,000

Dukes County, MA real estate trends

$1.89M

Sale price

-22.3%
since last year

$1.04K

Sale $/sq ft

-0.096%
since last year

Under list price

3.8%

Days on market

Down payment

—

Total homes sold

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