Homes with Basements for Sale in Dukes County, MA

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ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. Inside, the unit has been tastefully renovated with new hardwood floors, an updated bathroom, updated kitchen appliances, and a freshly painted interior. Being sold furnished, this true gem is ready for immediate occupancy.

$550,000

2 beds1 bath725 sq ft

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

Swimming pool • New roof • Colorful landscaping

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic vi

$899,000

2 beds1 bath990 sq ft

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

Custom wood features • Roof top deck • Panoramic views

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system.

$1,199,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Open floor plan • Recent upgrades • New roofs

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living are

$15,400,000

6 beds8 baths6,967 sq ft

8 Snail Rd, Chilmark, MA 02535

Sport court • Outdoor living areas • Protected views

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft. , second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners

$2,595,000

2 beds2 baths960 sq ft

131 North Water St-collins Cottage #22, Edgartown, MA 02539

Concierge services • Outdoor shower • Turnkey residence

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 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 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 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 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 103 Edgartown Bay Rd, Edgartown, MA 02539, 4 beds, 3 baths

$6,995,000

4 beds3 baths2,624 sq ft

103 Edgartown Bay Rd, Edgartown, MA 02539

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

Property at 131 North Water St -rowley Cottage #62, Edgartown, MA 02539, 2 beds, 2 baths

$2,425,000

2 beds2 baths895 sq ft

131 North Water St -rowley Cottage #62, Edgartown, MA 02539

Property at 17 Chapman Ln, Edgartown, MA 02539, 3 beds, 1 bath

$1,395,000

3 beds1 bath1,066 sq ft

17 Chapman Ln, Edgartown, MA 02539

Property at 29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 5 beds, 4 baths

$3,295,000

5 beds4 baths2,330 sq ft

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

Property at 96 Hammett Ln, Chilmark, MA 02535, 3 beds, 3 baths

$3,795,000

3 beds3 baths3,426 sq ft

96 Hammett Ln, Chilmark, MA 02535

Property at 5 Pinetree Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,999,000

4 beds3 baths2,730 sq ft

5 Pinetree Ln, Vineyard Haven, MA 02568

Property at 31 Lambert's Cove Rd, Vineyard Haven, MA 02568, 6 beds, 7.5 baths

$5,800,000

6 beds7.5 baths5,732 sq ft

31 Lambert's Cove Rd, Vineyard Haven, MA 02568

Property at 18 Wood Duck Way, Edgartown, MA 02539, 4 beds, 3 baths

$1,800,000

4 beds3 baths2,864 sq ft

18 Wood Duck Way, Edgartown, MA 02539

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

$1,175,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

Property at 64 Christiantown, West Tisbury, MA 02575, 4 beds, 4 baths

$3,495,000

4 beds4 baths3,200 sq ft

64 Christiantown, West Tisbury, MA 02575

Property at 261 Sandpiper Ln #12, Tisbury, MA 02539, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,682 sq ft

261 Sandpiper Ln #12, Tisbury, MA 02539

Property at 159 Lake St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,195,000

5 beds4 baths3,328 sq ft

159 Lake St, Vineyard Haven, MA 02568

Property at 99 Old Purchase Rd, Edgartown, MA 02539, 4 beds, 2.5 baths

$1,850,000

4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, Edgartown, MA 02539

Property at 20 James Pond Way, West Tisbury, MA 02575, 5 beds, 3 baths

$3,600,000

5 beds3 baths2,701 sq ft

20 James Pond Way, West Tisbury, MA 02575

Property at 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557, 1 bed, 1 bath

$869,000

1 bed1 bath797 sq ft

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

Property at 9 Suttons Way, Edgartown, MA 02539, 7 beds, 6.5 baths

$7,999,000

7 beds6.5 baths7,133 sq ft

9 Suttons Way, Edgartown, MA 02539

Property at 94 Weaver Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$3,999,999

4 beds3 baths2,715 sq ft

94 Weaver Ln, Vineyard Haven, MA 02568

Property at 49 Gosnolds Way, Chilmark, MA 02535, 5 beds, 3.5 baths

$5,200,000

5 beds3.5 baths4,044 sq ft

49 Gosnolds Way, Chilmark, MA 02535

Property at 111 Charles Neck Way, West Tisbury, MA 02575, 3 beds, 2 baths

$1,499,000

3 beds2 baths1,562 sq ft

111 Charles Neck Way, West Tisbury, MA 02575

Property at 23 Beetle Swamp Rd, Edgartown, MA 02539, 8 beds, 5 baths

$3,995,000

8 beds5 baths4,651 sq ft

23 Beetle Swamp Rd, Edgartown, MA 02539

Property at 85 North Reservoir Rd, West Tisbury, MA 02575, 5 beds, 6 baths

$7,500,000

5 beds6 baths4,531 sq ft

85 North Reservoir Rd, West Tisbury, MA 02575

Property at 33 Goethals Way, Vineyard Haven, MA 02568, 5 beds, 2.5 baths

$7,950,000

5 beds2.5 baths2,794 sq ft

33 Goethals Way, Vineyard Haven, MA 02568

Property at 205 South Rd, Chilmark, MA 02575, 4 beds, 4.5 baths

$4,995,000

4 beds4.5 baths5,402 sq ft

205 South Rd, Chilmark, MA 02575

Property at 26 Union Ct #7, Vineyard Haven, MA 02568, 2 beds, 2.5 baths

$1,625,000

2 beds2.5 baths1,532 sq ft

26 Union Ct #7, 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.

Homes with Basements for Sale in Dukes County

There are currently 93 homes with basements 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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