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

105 homes

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ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
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

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
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

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated custom kitchen by French Accent, with a walk-in pantry, opens to the dining area, while a first-floor powder room with laundry adds everyday convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additiona

$1,285,000

3 beds2.5 baths2,347 sq ft

41 Cook Rd, Vineyard Haven, MA 02568

Landscaped grounds • Walk-in pantry • 0.32 acre lot

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in chara

$2,995,000

4 beds1.5 baths3,462 sq ft

27 Beach Rd, Oak Bluffs, MA 02557

Dock • Harbor views • Waterfront

ABOUT THIS HOME
Waterfront Home for sale in Dukes County, MA:
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval,

$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

Wood stove • Codman spring road • 0.88 acres

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 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 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 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 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 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 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 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 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 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 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 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 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 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 52 Oak Knl, West Tisbury, MA 02575, 3 beds, 2 baths

$1,225,000

3 beds2 baths1,800 sq ft

52 Oak Knl, West Tisbury, MA 02575

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

$1,499,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

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

$1,875,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

Property at 28 Beach Rd, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$3,675,000

4 beds2.5 baths1,800 sq ft

28 Beach Rd, Oak Bluffs, MA 02557

Property at 312 East Chop Dr, Oak Bluffs, MA 02557, 3 beds, 3 baths

$2,195,000

3 beds3 baths1,425 sq ft

312 East Chop Dr, Oak Bluffs, MA 02557

Property at 28 Grovedale Rd, Oak Bluffs, MA 02568, 3 beds, 3.5 baths

$1,750,000

3 beds3.5 baths2,376 sq ft

28 Grovedale Rd, Oak Bluffs, MA 02568

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 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 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 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 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

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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.

Waterfront Homes for Sale in Dukes County

There are currently 105 waterfront homes for sale in Dukes County at a median listing price of $2.4M. 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 74 days. This map is refreshed with the newest listings in Dukes County every 15 minutes.

In the past month, 9 homes have been sold in Dukes County. In addition to houses in Dukes County, there were also 12 condos, 1 townhouse, and 3 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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