Dukes County, MA homes for sale & real estate

145 homes

Sort:

Recommended

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club, this property offers unparalleled convenience paired with a sense of seclusion. At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, expansive counter space, a generous pantry room, and window-lined separate dining room ideal for both casual or formal dining. Step out

$2,495,000

4 beds3 baths2,562 sq ft

21 Woodlawn Ave, Vineyard Haven, MA 02568

Private deck • Generous pantry room • Screened-in porch

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Welcome to this delightful Cape-style home offering easy access to Vineyard Haven shopping and the Island's bike paths. Nestled on just under an acre of land, this inviting residence features three spacious bedrooms and two full bathrooms, providing ample space for year-round living or weekend getaways. Inside, you'll find a warm and welcoming open concept, perfect for both relaxing and entertaining. The home boasts a sun-filled living room, a kitchen, and a dining area ideal for gatherings. With one bedroom and bath on the main floor and two additional bedrooms and full bath upstairs, there's room for everyone. Enjoy the tranquility of the expansive yard--ideal for gardening, outdoor play,

$1,045,000

3 beds2 baths1,469 sq ft

12 Park Ave, Vineyard Haven, MA 02568

Access to bike paths • Ideal for gardening • Expansive yard

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J. G. Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite. The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additio

$8,900,000

8 beds8 baths8,560 sq ft

150 East Chop Dr, Oak Bluffs, MA 02557

0.64 acre lot • 2 garage spots • Built 2017

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the thoughtfully curated interiors and unique floor plan, every detail reflects impeccable craftsmanship and intentional design. The outdoor living space is equally remarkable, featuring a heated saltwater pool, a sunken fire pit, and a show stopping custom glass wall feature. With a strong, proven rental

$9,499,000

4 beds6 baths5,458 sq ft

43 Peases Point Way S, Edgartown, MA 02539

Tranquil courtyard • Unique floor plan • Gated arbor entry

ABOUT THIS HOME
Dukes County, MA Homes for Sale
3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full kitchen, full bathroom and a loft. Year built 2017. interior photos to come. Also 12X10 post and beam shead.

$1,795,000

3 beds3.5 baths2,311 sq ft

7 Candle Maker Cir, Edgartown, MA 02539

0.51 acre lot • 2 garage spots • Built 1985

Property at 96 Machester Ave, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,149,000

3 beds2 baths1,596 sq ft

96 Machester Ave, Oak Bluffs, MA 02557

Property at 7 Clark Dr, Edgartown, MA 02539, 4 beds, 5 baths

$4,800,000

4 beds5 baths4,280 sq ft

7 Clark Dr, 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 25 Lelands Path, Edgartown, MA 02539, 6 beds, 7.5 baths

$9,995,000

6 beds7.5 baths7,205 sq ft

25 Lelands Path, Edgartown, MA 02539

Property at 71 Sixth St N, Edgartown, MA 02539, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths2,236 sq ft

71 Sixth St N, Edgartown, MA 02539

Property at 113 Leonard Cir, Vineyard Haven, MA 02568, 4 beds, 2 baths

$1,099,000

4 beds2 baths1,306 sq ft

113 Leonard Cir, Vineyard Haven, MA 02568

Property at 16 Atlantic Ave, Oak Bluffs, MA 02557, 5 beds, 2.5 baths

$2,495,000

5 beds2.5 baths2,577 sq ft

16 Atlantic Ave, Oak Bluffs, MA 02557

Property at 50 Lantern Ln, Vineyard Haven, MA 02568, 3 beds, 1.5 baths

$1,193,000

3 beds1.5 baths1,040 sq ft

50 Lantern Ln, Vineyard Haven, MA 02568

Property at 385 Barnes Rd, Oak Bluffs, MA 02557, 3 beds, 4.5 baths

$5,995,000

3 beds4.5 baths3,608 sq ft

385 Barnes Rd, Oak Bluffs, MA 02557

Property at 23 Circuit Ave Ext, Oak Bluffs, MA 02557, 3 beds, 1 bath

$2,700,000

3 beds1 bath1 sq ft

23 Circuit Ave Ext, Oak Bluffs, MA 02557

Property at 47 E East Chop Dr #5, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath650 sq ft

47 E East Chop Dr #5, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #4, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,995,000

2 beds1 bath879 sq ft

47 E Chop Dr #4, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #2, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath736 sq ft

47 E Chop Dr #2, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #3, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,995,000

2 beds1 bath802 sq ft

47 E Chop Dr #3, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #1, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath731 sq ft

47 E Chop Dr #1, Oak Bluffs, MA 02557

Property at 135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$5,999,000

4 beds3.5 baths2,995 sq ft

135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539

Property at 9 Sampson Ave, Edgartown, MA 02539, 3 beds, 2 baths

$1,095,000

3 beds2 baths2,046 sq ft

9 Sampson Ave, Edgartown, MA 02539

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

Property at 150 Cove Rd #10, Vineyard Haven, MA 02568, 2 beds, 3 baths

$1,699,000

2 beds3 baths1,737 sq ft

150 Cove Rd #10, Vineyard Haven, MA 02568

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

$1,895,000

4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, Edgartown, MA 02539

Property at 47 E Chop Dr, Oak Bluffs, MA 02557, 8 beds, 6 baths

$10,500,000

8 beds6 baths3,888 sq ft

47 E Chop Dr, Oak Bluffs, MA 02557

Property at 357 W Tisbury Rd, Edgartown, MA 02539, 5 beds, 4.5 baths

$2,650,000

5 beds4.5 baths4,115 sq ft

357 W Tisbury Rd, Edgartown, MA 02539

Property at 5 Pip'n Rd, Edgartown, MA 02539, 3 beds, 2 baths

$1,395,000

3 beds2 baths1,800 sq ft

5 Pip'n Rd, Edgartown, MA 02539

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

$2,395,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Property at 261 Sandpiper Ln #12, Vineyard Haven, MA 02568, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,628 sq ft

261 Sandpiper Ln #12, 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 4 Somerset Ln, Edgartown, MA 02539, 4 beds, 4.5 baths

$5,750,000

4 beds4.5 baths3,643 sq ft

4 Somerset Ln, Edgartown, MA 02539

Property at 63 Bayes Hill Rd Rd, Oak Bluffs, MA 02557, 4 beds, 4 baths

$3,150,000

4 beds4 baths5,165 sq ft

63 Bayes Hill Rd Rd, Oak Bluffs, MA 02557

Property at 72 Chappaquiddick Ave, Edgartown, MA 02539, 8 beds, 7.5 baths

$2,999,000

8 beds7.5 baths3,770 sq ft

72 Chappaquiddick Ave, Edgartown, MA 02539

Property at 30 Franklin Ave, Oak Bluffs, MA 02557, 2 beds, 2.5 baths

$2,150,000

2 beds2.5 baths2,137 sq ft

30 Franklin Ave, Oak Bluffs, MA 02557

Property at 157 Ben Chase Rd, West Tisbury, MA 02575, 4 beds, 2.5 baths

$2,250,000

4 beds2.5 baths2,982 sq ft

157 Ben Chase Rd, West Tisbury, MA 02575

Property at 4 High Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 3.5 baths

$2,260,000

4 beds3.5 baths2,810 sq ft

4 High Meadow Ln, Oak Bluffs, MA 02557

Property at 68 N Water St, Edgartown, MA 02539, 6 beds, 7.5 baths

$15,500,000

6 beds7.5 baths1,320 sq ft

68 N Water St, Edgartown, MA 02539

Property at 4 Boldwater Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$4,150,000

4 beds3.5 baths3,552 sq ft

4 Boldwater Rd, Edgartown, MA 02539

Property at 1 Field Club Dr, Edgartown, MA 02539, 5 beds, 4 baths

$9,250,000

5 beds4 baths3,550 sq ft

1 Field Club Dr, Edgartown, MA 02539

Property at 25 Dock St, Edgartown, MA 02539, 4 beds, 4.5 baths

$25,000,000

4 beds4.5 baths2,347 sq ft

25 Dock St, Edgartown, MA 02539

Viewing page 3 of 4

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 Mon Nov 24 2025. 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. © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Average home prices near Dukes County, MA

Cities

Chilmark homes for sale
$3,195,000
Oak Bluffs homes for sale
$1,495,000
Woods Hole homes for sale
$1,940,000
West Tisbury homes for sale
$2,072,500
Vineyard Haven homes for sale
$1,650,000
Edgartown homes for sale
$6,947,500
Tisbury homes for sale
$1,674,500
Aquinnah homes for sale
$7,450,000
Oak Bluffs homes for sale
$1,995,000
Falmouth homes for sale
$874,450

Counties

Plymouth County homes for sale
$705,000
Barnstable County homes for sale
$849,900
Bristol County homes for sale
$575,000

Dukes County, MA real estate trends

All Home Types trends in Dukes County, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,475,000

-2.0% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Dukes County, MA

$1,475,000

-2.0%

See more Dukes County, MA market insights

More to explore in Dukes County, MA

How to buy a house in Dukes County, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.