Homes with Basements for Sale in Dukes County, MA

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NEW 19 HRS AGO

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

NEW 9 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
Set on over an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the property enjoys a peaceful pastoral setting with vibrant flower gardens and expansive outdoor living spaces. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound offers the best of both worlds. With more than 4,000 square feet of living space across the main house, guest house, and detached garage with office above, there is ample room for both gatheri

$5,820,000

6 beds5 baths4,359 sq ft

29 Llewellyn Way, Edgartown, MA 02539

Downtown edgartown • Landscaped grounds • 1.04 acre lot

FLOOR PLAN

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

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

FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Dukes County, MA:
A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & picklebal

$1,875,000

4 beds3 baths2,068 sq ft

42 Bold Meadow Rd, Edgartown, MA 02539

Kitchenette • Walkout basement • New kitchen

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 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 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 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 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 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 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 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 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 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 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 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 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

Property at 99 Oak Ln, West Tisbury, MA 02575, 4 beds, 3 baths

$2,200,000

4 beds3 baths2,631 sq ft

99 Oak Ln, West Tisbury, MA 02575

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 2 Lexington Ave, Edgartown, MA 02539, 4 beds, 4.5 baths

$7,695,000

4 beds4.5 baths7,766 sq ft

2 Lexington Ave, Edgartown, MA 02539

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 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 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 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 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 21 Vickers St, Edgartown, MA 02539, 3 beds, 2 baths

$3,075,000

3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

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

$1,495,000

3 beds3.5 baths2,739 sq ft

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

Property at 8 Pip'n Cir, Edgartown, MA 02539, 3 beds, 2 baths

$1,500,000

3 beds2 baths1,717 sq ft

8 Pip'n Cir, Edgartown, MA 02539

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

$1,775,000

4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, 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 261 Sandpiper Ln #12, Tisbury, MA 02539, 3 beds, 3 baths

$1,175,000

3 beds3 baths1,682 sq ft

261 Sandpiper Ln #12, Tisbury, MA 02539

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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 Sat Oct 10 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 83 homes with basements 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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