Luxury homes for sale & real estate in Vineyard Haven, MA

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ABOUT THIS HOME
Luxury Home for sale in Vineyard Haven, MA:
Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and abundant natural light throughout, this move-in-ready home blends comfort and style. Ideal for year-round living or seasonal retreat.

$1,095,000

3 beds1.5 baths1,487 sq ft

12 Wheelhouse Way, Oak Bluffs, MA 02557

8,861 sq ft lot • Built 1999 • Listed 23 days

ABOUT THIS HOME
Luxury Home for sale in Vineyard Haven, MA:
An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining room. The kitchen is at the back of the house with the mudroom and side entrance beyond. Enjoy the beautiful natural light in the spacious sun room at the front of the house with French doors leading to the side yard. The property offers charm and potential in a sought-after location. Several updates w

$875,000

2 beds1 bath861 sq ft

24 School St, Oak Bluffs, MA 02557

Spacious sun room • 0.24 acre lot • Garage

ABOUT THIS HOME
Luxury Home for sale in Vineyard Haven, MA:
Country Living so close to Town! Lovely 3 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. Living Room with additional nook. Half bath. Interior stairs to lower level with private exterior entrance and garage. 2nd floor has large primary bedroom with cathedral ceilings, walk through double closet and generous private bath with jacuzzi, separate shower and laundry facilities. Two additional bedrooms. two full baths. Attic. Grassy areas on front and side of property. Small association off West Spring St. R10 Zoning. Propane FHW Heat Pump A/C Radiant Heat on lower level Town Water , T

$1,495,000

3 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Large side deck • Cathedral ceilings • Jacuzzi

ABOUT THIS HOME
Luxury Home for sale in Vineyard Haven, MA:
West Tisbury Farmhouse with all of the Historic Charm! 1743/1850, once owned by the renowned sailor & author Joshua Slocum. Located on a lush 1.27 acres, this property has all the makings of a perfect family compound with a 4 bedroom, 2 Bathroom Main House and a 1 Bedroom, 1 Bathroom Guest Cottage. From the patio entry you will arrive into the bright, custom kitchen with new appliances, 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 kitchen then opens up to the dining area and additional sitting area, with exposed beams, period plaster walls, wide wooden floorboards and on

$1,892,500

5 beds3 baths2,552 sq ft

10 Dan'ls Way, West Tisbury, MA 02575

Custom kitchen • Period plaster walls • New appliances

ABOUT THIS HOME
Luxury Home for sale in Vineyard Haven, MA:
Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs' most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood's peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and

$1,825,000

4 beds3 baths3,142 sq ft

7 South Meadow Ln, Oak Bluffs, MA 02557

Third floor den • Exterior decks • 0.66 acre lot

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

$1,650,000

5 beds3 baths1,811 sq ft

22 Old Lighthouse Rd, Vineyard Haven, MA 02568

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 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 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 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 151 Tashmoo Ave, Tisbury, MA 02468, 4 beds, 3.5 baths

$2,295,000

4 beds3.5 baths2,690 sq ft

151 Tashmoo Ave, Tisbury, MA 02468

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 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 26 Hampson Ave, Oak Bluffs, MA 02557, 2 beds, 2 baths

$999,999

2 beds2 baths1,078 sq ft

26 Hampson Ave, Oak Bluffs, MA 02557

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 27 Chapde Ln, Vineyard Haven, MA 02568, 3 beds, 2.5 baths

$1,615,000

3 beds2.5 baths1,740 sq ft

27 Chapde Ln, Vineyard Haven, MA 02568

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 34 Davis St, Vineyard Haven, MA 02568, 3 beds, 3.5 baths

$2,195,000

3 beds3.5 baths2,453 sq ft

34 Davis St, Vineyard Haven, MA 02568

Property at 128 Spring St, Vineyard Haven, MA 02568, 5 beds, 3.5 baths

$1,575,000

5 beds3.5 baths2,436 sq ft

128 Spring St, Vineyard Haven, MA 02568

Property at 136 Spring St, Vineyard Haven, MA 02568, 1 bed, 1 bath

$850,000

1 bed1 bath534 sq ft

136 Spring St, Vineyard Haven, MA 02568

Property at 8 Paddock Rd, Oak Bluffs, MA 02557, 4 beds, 5.5 baths

$5,450,000

4 beds5.5 baths3,300 sq ft

8 Paddock Rd, Oak Bluffs, MA 02557

Property at 159 Lake St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,595,000

5 beds4 baths3,329 sq ft

159 Lake St, Vineyard Haven, MA 02568

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

$1,449,000

3 beds1 bath1,033 sq ft

9 Brunswick 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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

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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 Tue Dec 02 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.

Luxury Homes for Sale in Vineyard Haven

There are currently 65 luxury homes for sale in Vineyard Haven at a median listing price of $2.07M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Vineyard Haven stay on the market for 122 days. Popular neighborhoods include Martha's Vineyard. This map is refreshed with the newest listings in Vineyard Haven every 15 minutes.

In the past month, 1 home has been sold in Vineyard Haven. In addition to houses in Vineyard Haven, there were also 3 condos, 0 townhouses, and 1 multi-family unit for sale in Vineyard Haven last month. Find your dream home in Vineyard Haven 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 Vineyard Haven are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Vineyard Haven. Our Vineyard Haven real estate stats and trends will give you more information about home buying and selling trends in Vineyard Haven. If you're looking to sell your home in the Vineyard Haven area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Vineyard Haven with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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