Vintage homes for sale & real estate in Martha's Vineyard, MA

36 homes

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ABOUT THIS HOME
Vintage Home for sale in Martha's Vineyard, MA:
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
Vintage Home for sale in Martha's Vineyard, MA:
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
Vintage Home for sale in Martha's Vineyard, MA:
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
Vintage Home for sale in Martha's Vineyard, MA:
NEWLY LISTED l PRIME 1.14 ACRE PROPERTY IN EDGARTOWN -This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Ideally situated just minutes from Edgartown Village, with Katama and South Beach only a short distance away, the location blends convenience with coastal appeal. Dual access from Pease's Point Road and Mill Hill enhances the property's versatility. Please note that the listing agent or a representative must be present for all showings.

$3,250,000

3 beds2 baths1,528 sq ft

10 Peases Point Rd, Edgartown, MA 02539

Elevated parcel • R-20 lot • 1.14 acre property

ABOUT THIS HOME
Vintage Home for sale in Martha's Vineyard, MA:
HOUSE + GUEST HOUSE: Historic 4-Bedroom 2-Bathroom Main House & 1-Bedroom 1-Bathroom Cottage. Located on a lush 1.27 acres and just a short distance from Alley's General Store, 7a Foods + North Tisbury, this property has all the makings of a perfect family compound. With plenty of space for lawn games and gardens and no shortage of history & charm. There has been so much care put into its thoughtful layout, updates and additions over the years. From the patio entry you will arrive into the bright, custom kitchen with vaulted ceilings, a generous center island and sizable Verona gas range. Enjoy plenty of work space and additional storage in the walk-in pantry. From there the kit

$1,845,000

5 beds3 baths2,552 sq ft

10 Dan'ls Way, West Tisbury, MA 02575

Custom kitchen • Period plaster walls • New appliances

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 825 Main St, Vineyard Haven, MA 02568, 6 beds, 5 baths

$14,500,000

6 beds5 baths5,867 sq ft

825 Main St, Vineyard Haven, MA 02568

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

$9,795,000

6 beds6 baths6,135 sq ft

52 S Summer Street South, 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 50 Canonicus Ave, Oak Bluffs, MA 02557, 2 beds, 0.5 baths

$970,000

2 beds0.5 baths953 sq ft

50 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 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 124 Skiff Ave Unit D10, Vineyard Haven, MA 02568, 3 beds, 2 baths

$725,000

3 beds2 baths1,356 sq ft

124 Skiff Ave Unit D10, 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 124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568, 2 beds, 1 bath

$599,000

2 beds1 bath725 sq ft

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

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 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 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 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 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 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535, 5 beds, 4.5 baths

$4,950,000

5 beds4.5 baths3,413 sq ft

124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

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 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 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 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 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 12 & 14 Maple Ave, Oak Bluffs, MA 02557, 4 beds, 4 baths

$1,830,000

4 beds4 baths1,600 sq ft

12 & 14 Maple Ave, Oak Bluffs, MA 02557

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 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 #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 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 East Chop Dr, Oak Bluffs, MA 02557, 7 beds, 6 baths

$10,500,000

7 beds6 baths3,888 sq ft

47 East Chop Dr, 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

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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 Dec 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.

Vintage Homes for Sale in Martha's Vineyard

There are currently 36 vintage homes for sale in Martha's Vineyard at a median listing price of $2.19M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Martha's Vineyard stay on the market for 146 days. Popular neighborhoods include Edgartown Village Historic District, Chappaquiddick, Upper Cape, and East Chop. This map is refreshed with the newest listings in Martha's Vineyard every 15 minutes.

In the past month, 24 homes have been sold in Martha's Vineyard. In addition to houses in Martha's Vineyard, there were also 8 condos, 1 townhouse, and 5 multi-family units for sale in Martha's Vineyard last month. Find your dream home in Martha's Vineyard 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 Martha's Vineyard are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Martha's Vineyard. If you're looking to sell your home in the Martha's Vineyard area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Martha's Vineyard with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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