Dukes County, MA homes for sale & real estate

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking prism skylight that fills the interior with warmth and natural light. An expansive, open living area is anchored by a floor-to-ceiling, double-sided fieldstone fireplace, creating a welcoming gathering space with a strong connection to the surrounding landscape. A remarkable two-story screened porch captures the water

$3,995,000

4 beds5 baths4,904 sq ft

4 Garrett Way, Edgartown, MA 02539

Finished lower level • 3.37 acre lot • 2 garage spots

OPEN SAT, 10:30AM TO 12:30PMFLOOR PLAN

ABOUT THIS HOME
Dukes County, MA Homes for Sale
THE COMPOUND AT INDIAN HILL Three dwellings. One price. One house decides how you live. Three let you change your mind. More than three private acres in West Tisbury. 4,464 square feet across three buildings, each with its own front door. The Main House holds the center. Glass doors & generous windows pull the meadow inside. A stone fireplace anchors the room. The kitchen was built for dinners that run long. The Studio Barn is the open question. Four sets of French doors swing wide to a wildflower meadow, & the room goes with them. Artist's studio. Wellness space. Whatever you have been missing. The Guest House earns its keep. Three bedrooms, a loft-inspired living space, &

$3,790,000

7 beds4.5 baths4,464 sq ft

31 Josiah Sachem Way, West Tisbury, MA 02575

Private acres • Wildflower meadow • Artist's studio

FLOOR PLAN

ABOUT THIS HOME
Dukes County, MA Homes for Sale
PHOTOS COMING SOON-Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining. Set on . 5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceil

$4,195,000

5 beds3.5 baths3,594 sq ft

32 Marthas Rd, Edgartown, MA 02539

Expansive windows • Warm gas fireplace • Gourmet kitchen

ABOUT THIS HOME
Dukes County, MA Homes for Sale
The one you have been waiting for! Originally reimagined to be the owners forever home, this turnkey Katama gem is now ready for its next chapter. No expense or detail was spared in the magnificent, top-to-bottom transformation of this comfortable 3-bedroom, 4-full-bath Cape. From the thoughtful finishes to the seamless layout, every inch of this home has been lovingly updated to offer the ultimate blend of comfort and modern living. A spectacular custom built three season room --complete with a cozy fireplace--is the perfect place to entertain or just unwind and enjoy the incredible professionally landscaped grounds. The 37,000 ft, lot is surrounded by serene conservation land, ensuring p

$3,200,000

3 beds4 baths2,370 sq ft

16 Old Dunhams Corner Way, Edgartown, MA 02539

Blooming views • 0.86 acre lot • Garage

VIDEO TOUR

$7,250,000

4 beds4.5 baths2,961 sq ft

8 Beach Plum Mdws, Edgartown, MA 02539

1.65 acre lot • 2 garage spots • Built 2005

Property at 42 Bold Meadow Rd, Edgartown, MA 02539, 4 beds, 3 baths

$1,875,000

4 beds3 baths2,068 sq ft

42 Bold Meadow Rd, Edgartown, MA 02539

Property at 32 Norton Orchard Rd, Edgartown, MA 02539, 4 beds, 5 baths

$1,850,000

4 beds5 baths2,518 sq ft

32 Norton Orchard Rd, Edgartown, MA 02539

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

$1,755,000

3 beds3 baths2,815 sq ft

68 Front St, Oak Bluffs, MA 02557

Property at 24 Myober Ln, Edgartown, MA 02539, 4 beds, 4.5 baths

$2,995,000

4 beds4.5 baths2,348 sq ft

24 Myober Ln, Edgartown, MA 02539

Property at 7 Fawndale Rd, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,150,000

4 beds3 baths1,924 sq ft

7 Fawndale Rd, Vineyard Haven, MA 02568

Property at 98 Edgartown Bay Rd, Edgartown, MA 02539, 4 beds, 4.5 baths

$4,995,000

4 beds4.5 baths3,348 sq ft

98 Edgartown Bay Rd, Edgartown, MA 02539

Property at 12 Boldwater Rd, Edgartown, MA 02539, 8 beds, 10 baths

$9,950,000

8 beds10 baths7,585 sq ft

12 Boldwater Rd, Edgartown, MA 02539

Property at 72 Chappaquiddick, Edgartown, MA 02539, 8 beds, 6 baths

$2,950,000

8 beds6 baths3,770 sq ft

72 Chappaquiddick, Edgartown, MA 02539

Property at 234 County Rd, Oak Bluffs, MA 02557, 5 beds, 2 baths

$1,375,000

5 beds2 baths1,952 sq ft

234 County Rd, Oak Bluffs, MA 02557

Property at 20 Hidden Cv, Oak Bluffs, MA 02557, 4 beds, 3 baths

$1,595,000

4 beds3 baths1,898 sq ft

20 Hidden Cv, Oak Bluffs, MA 02557

Property at 61 Canonicus Ave, Oak Bluffs, MA 02557, 3 beds, 2.5 baths

$2,200,000

3 beds2.5 baths2,420 sq ft

61 Canonicus Ave, Oak Bluffs, MA 02557

Property at 74 Chase Lane & 25 Norton Ave, Vineyard Haven, MA 02568, 3 beds, 1.5 baths

$905,000

3 beds1.5 baths2,208 sq ft

74 Chase Lane & 25 Norton Ave, Vineyard Haven, MA 02568

Property at 4 Farm Way, Edgartown, MA 02539, 7 beds, 4 baths

$1,825,000

7 beds4 baths2,597 sq ft

4 Farm Way, Edgartown, MA 02539

Property at 8 Jeffers Way, Aquinnah, MA 02535, 3 beds, 3.5 baths

$2,490,000

3 beds3.5 baths3,579 sq ft

8 Jeffers Way, Aquinnah, MA 02535

Property at 125 Mayflower Ln, Vineyard Haven, MA 02568, 4 beds, 3.5 baths

$2,295,000

4 beds3.5 baths3,056 sq ft

125 Mayflower Ln, Vineyard Haven, MA 02568

Property at 148 Katama Rd, Edgartown, MA 02539, 5 beds, 3 baths

$4,100,000

5 beds3 baths3,654 sq ft

148 Katama Rd, Edgartown, MA 02539

Property at 62 Schoolhouse Rd, Edgartown, MA 02539, 5 beds, 4 baths

$3,400,000

5 beds4 baths3,095 sq ft

62 Schoolhouse Rd, Edgartown, MA 02539

Property at 43 N Slope Ln, Chilmark, MA 02535, 3 beds, 2 baths

$1,649,900

3 beds2 baths1,540 sq ft

43 N Slope Ln, Chilmark, MA 02535

Property at 99 The Blvd, Edgartown, MA 02539, 4 beds, 4.5 baths

$2,455,000

4 beds4.5 baths3,039 sq ft

99 The Blvd, Edgartown, MA 02539

Property at 1 Mariners Way Unit A, Edgartown, MA 02539, 0.5 baths

$1,399,000

Studio0.5 baths1,992 sq ft

1 Mariners Way Unit A, Edgartown, MA 02539

Property at 31 Temahigan Ave, Oak Bluffs, MA 02557, 4 beds, 3.5 baths

$2,678,000

4 beds3.5 baths2,363 sq ft

31 Temahigan Ave, Oak Bluffs, MA 02557

Property at 27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02557, 1 bed, 1 bath

$287,500

1 bed1 bath388 sq ft

27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02557

Property at 10 Woodhaven Dr, Edgartown, MA 02539, 3 beds, 2.5 baths

$2,500,000

3 beds2.5 baths2,876 sq ft

10 Woodhaven Dr, Edgartown, MA 02539

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

$785,000

2 beds1 bath624 sq ft

60R Carol Ln, Oak Bluffs, MA 02557

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

$1,995,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Property at 267 Barnes Rd, Oak Bluffs, MA 02557, 3 beds, 5.5 baths

$4,395,000

3 beds5.5 baths4,046 sq ft

267 Barnes Rd, Oak Bluffs, MA 02557

Property at 49 The Blvd, Edgartown, MA 02539, 6 beds, 2 baths

$2,850,000

6 beds2 baths1,957 sq ft

49 The Blvd, Edgartown, MA 02539

Property at 21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02557, 1 bed, 1.5 baths

$389,000

1 bed1.5 baths590 sq ft

21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02557

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

$10,750,000

7 beds4 baths4,855 sq ft

139 Chappaquiddick Rd, Edgartown, MA 02539

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

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

Property at 30 Water Gate Rd, Vineyard Haven, MA 02568, 5 beds, 4.5 baths

$3,495,000

5 beds4.5 baths4,816 sq ft

30 Water Gate Rd, Vineyard Haven, MA 02568

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

$1,289,000

2 beds2 baths1,996 sq ft

29 Scotchmans Ln, West Tisbury, MA 02575

Property at 18 Sylvan Ave, Vineyard Haven, MA 02568, 4 beds, 4 baths

$2,095,000

4 beds4 baths2,876 sq ft

18 Sylvan Ave, Vineyard Haven, MA 02568

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

$2,595,000

4 beds2.5 baths1,858 sq ft

59 Tuckernuck Ave, Oak Bluffs, MA 02557

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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 Fri Oct 09 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
$2,195,000
Oak Bluffs homes for sale
$1,315,000
Woods Hole homes for sale
$3,950,000
West Tisbury homes for sale
$3,495,000
Vineyard Haven homes for sale
$1,600,000
Edgartown homes for sale
$2,510,000
Tisbury homes for sale
$1,895,000
Aquinnah homes for sale
$3,050,000
Oak Bluffs homes for sale
$1,595,000
Falmouth homes for sale
$949,000

Counties

Plymouth County homes for sale
$725,000
Barnstable County homes for sale
$899,000
Bristol County homes for sale
$580,000

Dukes County, MA real estate trends

$1.38M

Sale price

-7.8%
since last year

$1.06K

Sale $/sq ft

+15.2%
since last year

Under list price

6.1%

Days on market

Down payment

—

Total homes sold

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