Waterfront homes for sale & real estate in Dukes County, MA

102 homes

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NEW 12 HRS AGO

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry. The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-

$2,875,000

4 beds4.5 baths2,900 sq ft

91 Litchfield Rd, Edgartown, MA 02539

Ensuite baths • High-end appliances • Cathedral ceilings

NEW 8 HRS AGOFLOOR PLAN

$1,075,000

3 beds2 baths948 sq ft

21 Flamingo Dr, Edgartown, MA 02539

0.5 acre lot • 3 parking spots • Built 1985

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
Thought to have been moved from the Campgrounds to the Highlands in the early 1900's, the Mary E. Gilkes house has been transformed into a sophisticated and easy-living Island abode. The thoughtful, intentional design and execution of this renovation/addition pays homage to its Victorian roots while adding every modern amenity for year-round or summer use. Every detail has been carefully considered from the mahogany front porch with Vineyard-blue ceilings that typifies the Oak Bluffs cottage history, to the "bonus" room/loft, to infrastructure which meets HERS requirements for energy efficiency. There isn't an inch of wasted space in this little powerhouse and the property offers

$1,950,000

2 beds2 baths1,459 sq ft

25 Oak Ave, Oak Bluffs, MA 02557

Mahogany front porch • Bonus room • Energy efficiency

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths between the main house and detached 1 bedroom guest suite. In the main house, the spacious great room boasts cathedral ceilings, wood-burning fireplace, and glass doors that seamlessly connect the interior to the outdoors. The custom kitchen is outfitted with an expansive granite center island, stainless steel appliances and a generous dining area. The private primary retreat includes a cu

$3,950,000

5 beds4.5 baths4,125 sq ft

6 Hollow Way, Edgartown, MA 02539

Custom kitchen • Fully furnished • 0.93 acre lot

$6,500,000

6 beds6 baths4,753 sq ft

16 Red Coat Hl, West Tisbury, MA 02575

4.85 acre lot • 2 garage spots • Pool

Property at 41 Hagerty Dr, Vineyard Haven, MA 02568, 6 beds, 6.5 baths

$5,750,000

6 beds6.5 baths5,424 sq ft

41 Hagerty Dr, Vineyard Haven, MA 02568

Property at 78 Plantingfield Way, Edgartown, MA 02568, 4 beds, 5.5 baths

$6,125,000

4 beds5.5 baths4,107 sq ft

78 Plantingfield Way, Edgartown, MA 02568

Property at 4 Garrett Way, Edgartown, MA 02539, 4 beds, 5 baths

$3,995,000

4 beds5 baths4,904 sq ft

4 Garrett Way, Edgartown, MA 02539

Property at 26 Pulpit Ln, Edgartown, MA 02539, 3 beds, 3 baths

$3,295,000

3 beds3 baths2,701 sq ft

26 Pulpit Ln, Edgartown, MA 02539

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

$9,500,000

8 beds10 baths7,585 sq ft

12 Boldwater 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 16 Old Dunhams Corner Way, Edgartown, MA 02539, 3 beds, 4 baths

$3,200,000

3 beds4 baths2,370 sq ft

16 Old Dunhams Corner Way, 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 8 Beach Plum Mdws, Edgartown, MA 02539, 4 beds, 4.5 baths

$6,900,000

4 beds4.5 baths2,961 sq ft

8 Beach Plum Mdws, 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 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 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 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 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 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 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 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 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 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 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 41 & 0 Cook Rd, Vineyard Haven, MA 02568, 3 beds, 2.5 baths

$1,570,000

3 beds2.5 baths2,347 sq ft

41 & 0 Cook Rd, Vineyard Haven, MA 02568

Property at 7 Ploughshare Ln, Oak Bluffs, MA 02557, 3 beds, 2.5 baths

$1,399,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

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

$1,395,000

4 beds4 baths2,670 sq ft

528 Main St, Vineyard Haven, MA 02568

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

$1,895,000

5 beds3 baths3,480 sq ft

135 Mayflower Ln, Vineyard Haven, MA 02568

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 33 Vineyard Ave, Oak Bluffs, MA 02557, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

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

$2,125,000

3 beds2.5 baths2,630 sq ft

81 Whalers Walk, Edgartown, MA 02539

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 299 Daggett Ave Unit A, Vineyard Haven, MA 02568, 3 beds, 1 bath

$1,095,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

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

$1,995,000

4 beds3 baths1,918 sq ft

21 & 25 Fulling Mill Rd, Chilmark, MA 02535

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 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

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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 Sun Oct 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.

Waterfront Homes for Sale in Dukes County

There are currently 102 waterfront homes for sale in Dukes County at a median listing price of $2.3M. 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 91 days. This map is refreshed with the newest listings in Dukes County every 15 minutes.

In the past month, 16 homes have been sold in Dukes County. In addition to houses in Dukes County, there were also 15 condos, 1 townhouse, and 4 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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