Dukes County, MA homes for sale & real estate

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms,

$1,499,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

Open floor plan • Front porch • Screened porch

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces includi

$1,875,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

Private balcony • Gourmet kitchen • Separate suite

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first floor features three bedrooms, a family room, full bath with laundry, and generous storage. Upstairs, the sun-filled living area includes a gourmet kitchen with Thermador® appliances, Silestone® counters, a gas fireplace, and an open layout that frames stunning Lagoon views. The private primary

$3,675,000

4 beds2.5 baths1,800 sq ft

28 Beach Rd, Oak Bluffs, MA 02557

Covered decks • Gourmet kitchen • Gas fireplace

ABOUT THIS HOME
Dukes County, MA Homes for Sale
“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering swimming, kayaking, and paddleboarding from your backyard. The main house features a welcoming sun porch, living room with a stone fireplace, light-filled primary bedroom with water views, and an updated kitchen and dining area with brick floors and a built-in

$2,195,000

3 beds3 baths1,425 sq ft

312 East Chop Dr, Oak Bluffs, MA 02557

Sun porch • Dining area • Stone fireplace

ABOUT THIS HOME
Dukes County, MA Homes for Sale
GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10’ stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL la

$1,750,000

3 beds3.5 baths2,376 sq ft

28 Grovedale Rd, Oak Bluffs, MA 02568

Wrap around porch • Separate entrance • Gas fireplace

Property at 68 Front St, Oak Bluffs, MA 02557, 3 beds, 3 baths

$1,755,000

3 beds3 baths2,695 sq ft

68 Front St, Oak Bluffs, MA 02557

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 40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557, 3 beds, 3.5 baths

$1,595,000

3 beds3.5 baths2,739 sq ft

40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557

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

$1,295,000

3 beds2 baths1,863 sq ft

3 Troy St, Oak Bluffs, MA 02557

Property at 312 E Chop Dr, Vineyard Haven, MA 02568, 3 beds, 2 baths

$2,195,000

3 beds2 baths1,425 sq ft

312 E Chop Dr, Vineyard Haven, MA 02568

Property at 21 W Spring St, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,450,000

4 beds3 baths1,270 sq ft

21 W Spring St, Vineyard Haven, MA 02568

Property at 19 Perkins Ave, Oak Bluffs, MA 02557, 2 beds, 1 bath

$825,000

2 beds1 bath985 sq ft

19 Perkins Ave, Oak Bluffs, MA 02557

Property at 27 Double Ox Rd, Oak Bluffs, MA 02557, 3 beds, 4.5 baths

$3,400,000

3 beds4.5 baths3,260 sq ft

27 Double Ox Rd, Oak Bluffs, MA 02557

Property at 11 Beach Rd, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,745,000

2 beds1 bath561 sq ft

11 Beach Rd, Oak Bluffs, MA 02557

Property at 19 Llewellyn Way, Edgartown, MA 02539, 4 beds, 5 baths

$3,200,000

4 beds5 baths3,428 sq ft

19 Llewellyn Way, 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 33 Alyssa Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,395,000

4 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Property at 48 Plantingfield Way, Edgartown, MA 02539, 2 beds, 1.5 baths

$3,495,000

2 beds1.5 baths1,388 sq ft

48 Plantingfield Way, Edgartown, MA 02539

Property at 28 Black Point Rd, Chilmark, MA 02535, 3 beds, 3 baths

$2,950,000

3 beds3 baths1,469 sq ft

28 Black Point Rd, Chilmark, MA 02535

Property at 132 South Rd, Chilmark, MA 02535, 3 beds, 3 baths

$1,600,000

3 beds3 baths2,155 sq ft

132 South Rd, Chilmark, MA 02535

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 218 Upper Main St, Edgartown, MA 02539, 1 bed, 1.5 baths

$2,495,000

1 bed1.5 baths1,236 sq ft

218 Upper Main St, 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 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 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557, 2 beds, 1 bath

$899,000

2 beds1 bath990 sq ft

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

Property at 47 Winemack St, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,199,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

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 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 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 35 South Bowl Rd, Chilmark, MA 02535, 3 beds, 2 baths

$4,995,000

3 beds2 baths2,710 sq ft

35 South Bowl Rd, Chilmark, MA 02535

Property at 0 Bayberry Hill Rd, Cuttyhunk, MA 02713, 3 beds, 2 baths

$1,195,000

3 beds2 baths1,472 sq ft

0 Bayberry Hill Rd, Cuttyhunk, MA 02713

Property at 22 Old Harbor Ln, Oak Bluffs, MA 02557, 4 beds, 2 baths

$1,850,000

4 beds2 baths1,833 sq ft

22 Old Harbor Ln, Oak Bluffs, MA 02557

Property at 81 Whalers Walk, Edgartown, MA 02539, 3 beds, 2.5 baths

$2,225,000

3 beds2.5 baths2,630 sq ft

81 Whalers Walk, Edgartown, MA 02539

Property at 44 Tiffany Dr, Oak Bluffs, MA 02557, 4 beds, 4.5 baths

$2,800,000

4 beds4.5 baths3,927 sq ft

44 Tiffany Dr, Oak Bluffs, MA 02557

Property at 7 Pip'n Cir, Edgartown, MA 02539, 5 beds, 3.5 baths

$2,195,000

5 beds3.5 baths2,628 sq ft

7 Pip'n Cir, Edgartown, MA 02539

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

$7,850,000

4 beds5 baths5,884 sq ft

24 Katama Bay View Rd, Edgartown, MA 02539

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

$4,600,000

6 beds5.5 baths3,998 sq ft

15 Tamarack Ln, Oak Bluffs, MA 02557

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

$5,225,000

6 beds4 baths2,890 sq ft

4 Canonicus Ave, Oak Bluffs, MA 02557

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 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 29 and 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 5 beds, 4 baths

$3,295,000

5 beds4 baths2,330 sq ft

29 and 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

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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 Aug 26 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
$1,895,000
Edgartown homes for sale
$2,875,000
Tisbury homes for sale
$1,975,000
Aquinnah homes for sale
$5,000,000
Oak Bluffs homes for sale
$1,800,000
Falmouth homes for sale
$972,450

Counties

Plymouth County homes for sale
$735,000
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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