Dukes County, MA homes for sale & real estate

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and basement with stylish finishes throughout. Originally crafted in the Victorian era and thoughtfully restored for contemporary living, this home enjoys an unbeatable setting and is steps to beaches, ferries, restaurants, galleries, and all the conveniences of downtown Oak Bluffs. Whether cherished a

$2,950,000

3 beds2.5 baths1,845 sq ft

33 Ocean Ave, Oak Bluffs, MA 02557

New kitchen • Updated baths • Historic oak bluffs

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Downtown Oak Bluffs located in the Copeland District this Victorian home combines historic charm with modern comfort. Offering 6 spacious bedrooms and 3.5 bathrooms, this home provides ample living space for family and guests. Also making an ideal rental property Sleeping 12 comfortably just a block to the restaurants and shops of Circuit Ave. and a couple of blocks to the beach it's the perfect location for leaving your car behind and enjoy the best the Island has to offer at your doorstep. With a three-sided porch overlooking Hartford Park, one of the many grassy parks throughout the historic Copeland district perfect for entertaining, dining al fresco or just relaxing outdoors on the man

$1,650,000

6 beds3.5 baths1,617 sq ft

34 Massasoit Ave, Oak Bluffs, MA 02557

Three-sided porch • Modern comfort • Perfect location

ABOUT THIS HOME
Dukes County, MA Homes for Sale
3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout, radiating a clean and brigh

$1,445,000

4 beds2.5 baths1,739 sq ft

22 Oklahoma Ave, Vineyard Haven, MA 02568

Spacious lot • Two decks • Full dry basement

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an expansive lawn perfect for entertaining or relaxing. Connected to town sewer, the property is approved for up to seven bedrooms--offering exceptional flexibility for future expansion and added value. The location affords both privacy and convenience, with all downtown amenities and South Beach within

$2,495,000

4 beds3 baths1,968 sq ft

105 Whalers Walk, Edgartown, MA 02539

Multiple patios • Expansive lawn • Backyard oasis

ABOUT THIS HOME
Dukes County, MA Homes for Sale
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passe

$1,575,000

2 beds1 bath924 sq ft

47 Quenames Rd, Chilmark, MA 02535

3.02 acre lot • Built 1992 • Listed 24 days

Property at 44 Plantingfield Way, Edgartown, MA 02539, 4 beds, 2.5 baths

$3,895,000

4 beds2.5 baths2,243 sq ft

44 Plantingfield Way, Edgartown, MA 02539

Property at 10 Dan'ls Way, West Tisbury, MA 02575, 5 beds, 3 baths

$1,845,000

5 beds3 baths2,552 sq ft

10 Dan'ls Way, West Tisbury, MA 02575

Property at 45 Quenames Rd, Chilmark, MA 02535, 2 beds, 1 bath

$1,575,000

2 beds1 bath896 sq ft

45 Quenames Rd, Chilmark, MA 02535

Property at 24 School St, Oak Bluffs, MA 02557, 2 beds, 1 bath

$875,000

2 beds1 bath861 sq ft

24 School St, Oak Bluffs, MA 02557

Property at 2 Lincoln Ave, Oak Bluffs, MA 02557, 1 bed, 1 bath

$640,000

1 bed1 bath354 sq ft

2 Lincoln Ave, Oak Bluffs, MA 02557

Property at 10 Peases Point Rd, Edgartown, MA 02539, 3 beds, 2 baths

$3,250,000

3 beds2 baths1,528 sq ft

10 Peases Point Rd, Edgartown, MA 02539

Property at 22 Old Lighthouse Rd, Vineyard Haven, MA 02568, 5 beds, 3 baths

$1,595,000

5 beds3 baths1,811 sq ft

22 Old Lighthouse Rd, Vineyard Haven, MA 02568

Property at 18 Spruce Gate Rd, Chilmark, MA 02535, 5 beds, 3.5 baths

$12,500,000

5 beds3.5 baths3,700 sq ft

18 Spruce Gate Rd, Chilmark, MA 02535

Property at 1 Saddle Club Rd, Edgartown, MA 02539, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths1,822 sq ft

1 Saddle Club Rd, Edgartown, MA 02539

Property at 4 Noman's Watch Rd, Aquinnah, MA 02535, 3 beds, 2.5 baths

$3,350,000

3 beds2.5 baths2,686 sq ft

4 Noman's Watch Rd, Aquinnah, MA 02535

Property at 12 Wheelhouse Way, Oak Bluffs, MA 02557, 3 beds, 1.5 baths

$1,095,000

3 beds1.5 baths1,487 sq ft

12 Wheelhouse Way, Oak Bluffs, MA 02557

Property at 112 Third Street North, Edgartown, MA 02539, 3 beds, 2 baths

$1,250,000

3 beds2 baths1,196 sq ft

112 Third Street North, Edgartown, MA 02539

Property at 344 Greenwood Ave, Vineyard Haven, MA 02568, 4 beds, 2 baths

$1,300,000

4 beds2 baths1,566 sq ft

344 Greenwood Ave, Vineyard Haven, MA 02568

Property at 50 Canonicus Ave, Oak Bluffs, MA 02557, 2 beds, 0.5 baths

$925,000

2 beds0.5 baths953 sq ft

50 Canonicus Ave, Oak Bluffs, MA 02557

Property at 52 S Summer Street South, Edgartown, MA 02539, 6 beds, 6 baths

$9,403,000

6 beds6 baths6,135 sq ft

52 S Summer Street South, Edgartown, MA 02539

Property at 10 Dory Cir, Edgartown, MA 02539, 4 beds, 3 baths

$1,600,000

4 beds3 baths1,738 sq ft

10 Dory Cir, Edgartown, MA 02539

Property at 33 Alyssa Ln, Vineyard Haven, MA 02568, 3 beds, 3 baths

$1,495,000

3 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Property at 7 South Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 3 baths

$1,825,000

4 beds3 baths3,142 sq ft

7 South Meadow Ln, Oak Bluffs, MA 02557

Property at 47 Tiffany Dr, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$2,499,000

4 beds2.5 baths2,544 sq ft

47 Tiffany Dr, Oak Bluffs, MA 02557

Property at 51 Lantern Ln, Vineyard Haven, MA 02568, 2 beds, 1 bath

$835,000

2 beds1 bath768 sq ft

51 Lantern Ln, Vineyard Haven, MA 02568

Property at 15 Old Farm Rd, Chilmark, MA 02535, 3 beds, 5 baths

$3,990,000

3 beds5 baths3,171 sq ft

15 Old Farm Rd, Chilmark, MA 02535

Property at 9 Brunswick Ave, Oak Bluffs, MA 02557, 3 beds, 1 bath

$1,395,000

3 beds1 bath1,033 sq ft

9 Brunswick Ave, Oak Bluffs, MA 02557

Property at 35 Double Ox Rd, Oak Bluffs, MA 02557, 3 beds, 3.5 baths

$2,250,000

3 beds3.5 baths2,475 sq ft

35 Double Ox Rd, Oak Bluffs, MA 02557

Property at 150 East Chop Dr, Oak Bluffs, MA 02557, 8 beds, 8 baths

$8,900,000

8 beds8 baths8,560 sq ft

150 East Chop Dr, Oak Bluffs, MA 02557

Property at 400 Barnes Rd, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$6,395,000

6 beds5.5 baths7,000 sq ft

400 Barnes Rd, Oak Bluffs, MA 02557

Property at 25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575, 2 beds, 2 baths

$1,100,000

2 beds2 baths1,583 sq ft

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Property at 56 N Neck Rd, Edgartown, MA 02539, 4 beds, 3 baths

$3,995,000

4 beds3 baths4,920 sq ft

56 N Neck Rd, Edgartown, MA 02539

Property at 187 Lagoon Pond Rd, Tisbury, MA 02575, 5 beds, 2 baths

$2,825,000

5 beds2 baths2,386 sq ft

187 Lagoon Pond Rd, Tisbury, MA 02575

Property at 46 Tiercel Ln, Chilmark, MA 02535, 2 beds, 1 bath

$1,650,000

2 beds1 bath716 sq ft

46 Tiercel Ln, Chilmark, MA 02535

Property at 6 Janes Cove Rd, Edgartown, MA 02539, 6 beds, 6.5 baths

$7,950,000

6 beds6.5 baths6,927 sq ft

6 Janes Cove Rd, Edgartown, MA 02539

Property at 60 -R Carol Ln, Oak Bluffs, MA 02557, 2 beds, 1 bath

$799,000

2 beds1 bath624 sq ft

60 -R Carol Ln, Oak Bluffs, MA 02557

Property at 7 Upper Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$1,799,000

4 beds2.5 baths3,268 sq ft

7 Upper Meadow Ln, Oak Bluffs, MA 02557

Property at 14 Twenty First St N, Edgartown, MA 02539, 3 beds, 1.5 baths

$1,200,000

3 beds1.5 baths1 sq ft

14 Twenty First St N, Edgartown, MA 02539

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 14 Trapps Pond Rd, Edgartown, MA 02539, 7 beds, 7 baths

$10,850,000

7 beds7 baths12,051 sq ft

14 Trapps Pond Rd, Edgartown, MA 02539

Property at 40 Scotchmans Ln, West Tisbury, MA 02575, 4 beds, 2 baths

$1,495,000

4 beds2 baths1,332 sq ft

40 Scotchmans Ln, West Tisbury, MA 02575

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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 Fri Jan 02 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.

Average home prices near Dukes County, MA

Cities

Chilmark homes for sale
$3,192,500
Oak Bluffs homes for sale
$1,495,000
Woods Hole homes for sale
$1,695,000
West Tisbury homes for sale
$1,845,000
Vineyard Haven homes for sale
$1,812,000
Edgartown homes for sale
$4,900,000
Tisbury homes for sale
$1,625,000
Aquinnah homes for sale
$5,400,000
Oak Bluffs homes for sale
$1,830,000
Falmouth homes for sale
$875,000

Counties

Plymouth County homes for sale
$710,000
Barnstable County homes for sale
$859,000
Bristol County homes for sale
$578,950

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)

$1,900,000

+2.8% YoY | Nov 2025

1 year
3 year
5 year

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

Location

Data

Nov 2025

Growth

% YoY

Dukes County, MA

$1,900,000

+2.8%

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