Dukes County, MA homes for sale & real estate

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ABOUT THIS HOME
Dukes County, MA Homes for Sale
This classic New England waterview home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The fren

$8,500,000

4 beds5 baths3,497 sq ft

24 Katama Bay View Rd, Edgartown, MA 02539

Large windows • Wine cellar • Open concept layout

ABOUT THIS HOME
Dukes County, MA Homes for Sale
PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED INSIDE AND OUT. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new heat/AC systems for year-round comfort. Recently installed professionally landscaped grounds offer curb appeal and outdoor enjoyment, complete with shower and patio furniture for al fresco dining and relaxing. Also included are ALL FURNISHINGS and a handy

$1,449,000

3 beds1 bath1,033 sq ft

9 Brunswick Ave, Oak Bluffs, MA 02557

New water line • New siding • Upgraded plumbing

ABOUT THIS HOME
Dukes County, MA Homes for Sale
This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper level is anchored by a cathedral-ceiling great room, where a wood-burning stone fireplace and three sets of French doors set the stage for cozy evenings and panoramic vistas. A chef’s kitchen equipped with high-end appliances and a comfortable dining area complements the open-concept design&mda

$4,695,000

5 beds5.5 baths4,003 sq ft

97 Longview Rd, West Tisbury, MA 02575

High-end appliances • Generous decks • Chef's kitchen

ABOUT THIS HOME
Dukes County, MA Homes for Sale
Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property, affords a private retreat or additional space for family and friends. Nestled in the heart of East Chop--a close-knit, sought-after community--this property is just a short distance from pristine beaches, the active harbor front, and vibrant downtown Oak Bluffs. A happy home, ready to welcome new memorie

$3,250,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Active harbor front • Guest cottage • Updated bathrooms

ABOUT THIS HOME
Dukes County, MA Homes for Sale
This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3-bedroom, 3-bathroom property checks all the boxes. With numerous bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval), this is a truly exceptional find. Just steps from Edgartown’s shops, restaurants, and harbor, the home sits in one of Martha’s Vineyard’s most desirable locations.

$1,350,000

3 beds3 baths1,959 sq ft

48 West Tisbry Rd, Edgartown, MA 02539

Expansion potential • Off-street parking • 3,920 sq ft lot

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 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 97 Longview Road Rd, West Tisbury, MA 02575, 5 beds, 5.5 baths

$4,695,000

5 beds5.5 baths4,003 sq ft

97 Longview Road Rd, West Tisbury, MA 02575

Property at 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 3 beds, 3 baths

$2,150,000

3 beds3 baths1,680 sq ft

33 Lagoon Pond Rd, Vineyard Haven, MA 02568

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

Property at 76 Washque Ave, Edgartown, MA 02539, 4 beds, 2.5 baths

$2,575,000

4 beds2.5 baths1,910 sq ft

76 Washque Ave, Edgartown, MA 02539

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 10 Duende Ln, Edgartown, MA 02539, 3 beds, 2 baths

$1,950,000

3 beds2 baths2,238 sq ft

10 Duende Ln, 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 108 Bay View Ave, Edgartown, MA 02539, 2 beds, 0.5 baths

$1,700,000

2 beds0.5 baths601 sq ft

108 Bay View Ave, Edgartown, MA 02539

Property at 58 Road to The Plns, Edgartown, MA 02539, 4 beds, 2 baths

$1,750,000

4 beds2 baths1,342 sq ft

58 Road to The Plns, Edgartown, MA 02539

Property at 139 Main St, Vineyard Haven, MA 02568, 5 beds, 6.5 baths

$3,750,000

5 beds6.5 baths4,372 sq ft

139 Main St, Vineyard Haven, MA 02568

Property at 1/3/5 Louis Field Rd, Edgartown, MA 02539, 11 beds, 8.5 baths

$8,995,000

11 beds8.5 baths6,289 sq ft

1/3/5 Louis Field Rd, Edgartown, MA 02539

Property at 8 Old Purchase Way, Edgartown, MA 02539, 4 beds, 2.5 baths

$2,150,000

4 beds2.5 baths2,547 sq ft

8 Old Purchase Way, Edgartown, MA 02539

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

$4,250,000

3 beds5 baths3,171 sq ft

15 Old Farm Rd, Chilmark, MA 02535

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 31 Lamberts Cove Rd, Vineyard Haven, MA 02568, 6 beds, 7.5 baths

$6,250,000

6 beds7.5 baths5,732 sq ft

31 Lamberts Cove Rd, Vineyard Haven, MA 02568

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

$1,475,000

3 beds2.5 baths1,822 sq ft

1 Saddle Club Rd, Edgartown, MA 02539

Property at 70 Carol Ln, Oak Bluffs, MA 02557, 2 beds, 2.5 baths

$1,200,000

2 beds2.5 baths1,500 sq ft

70 Carol Ln, Oak Bluffs, MA 02557

Property at 174 Middle Road Rd, Chilmark, MA 02535, 4 beds, 3.5 baths

$1,895,000

4 beds3.5 baths2,061 sq ft

174 Middle Road Rd, Chilmark, MA 02535

Property at 4 Canonicus Ave, Oak Bluffs, MA 02557, 6 beds, 4 baths

$5,325,000

6 beds4 baths2,890 sq ft

4 Canonicus Ave, Oak Bluffs, MA 02557

Property at 47 Winemack St, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,199,000

2 beds1 bath742 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Property at 15 Tamarack Ln, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$4,999,000

6 beds5.5 baths3,214 sq ft

15 Tamarack Ln, Oak Bluffs, MA 02557

Property at 108 Bay Vw, Edgartown, MA 02539, 2 beds, 0.5 baths

$1,700,000

2 beds0.5 baths601 sq ft

108 Bay Vw, Edgartown, MA 02539

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

$1,599,000

3 beds2 baths1,562 sq ft

111 Charles Neck Way, West Tisbury, MA 02575

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

$1,999,999

4 beds3 baths2,730 sq ft

5 Pinetree Ln, Vineyard Haven, MA 02568

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 43 Peases Point Way S, Edgartown, MA 02539, 4 beds, 6 baths

$9,499,000

4 beds6 baths5,458 sq ft

43 Peases Point Way S, Edgartown, MA 02539

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

$12,500,000

5 beds2.5 baths2,794 sq ft

33 Goethals Way, Vineyard Haven, MA 02568

Property at 124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568, 2 beds, 1 bath

$650,000

2 beds1 bath725 sq ft

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

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 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 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 71 Stoney Hill Road Rd, Vineyard Haven, MA 02568, 5 beds, 5 baths

$4,500,000

5 beds5 baths5,598 sq ft

71 Stoney Hill Road Rd, 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

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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 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%

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