34 Windemere Road, Oak Bluffs, MA 02557

bedrooms 4
bathrooms 2
|House
AUD $3,716,674
USD $2,579,000
Published on: 13 Apr 2026
Last updated on: 16 Sep 2026
34 Windemere Road, Oak Bluffs, MA 02557
34 Windemere Road, Oak Bluffs, MA 02557
34 Windemere Road, Oak Bluffs, MA 02557
+64
34 Windemere Road, Oak Bluffs, MA 02557
  • 64
Property ID: 110107243571
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1 Family, Oak Bluffs, MA

34 Windemere Road, Oak Bluffs, MA 02557
Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together a combined total of just over an acre of land. Included is Deeded Access, via a boardwalk to Brush Pond, with more wonderful views. Directly in front of the property lies a sandy beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf & a host of activities. This property offers both tranquility and convenience in one of Martha's Vineyard's most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for purchase separately. Excellent Rental History.

Property Details

Basic Info

Property Type
House
Listing Status
Active
Land Size
4,273.89 m2
Building Size
129.97 m2
Year Built
1910
Rooms
4 bedroom(s), 2 bathroom(s)
Provider
LINK Martha’s Vineyard
Brokerage Office Name
Alisan Lohan-Conway Properties
Brokerage Office Phone
(508) 627-1858
Neighbourhoods
3
Address
34 Windemere Road, Oak Bluffs, MA 02557

Tax History

YearTax amount
2026USD $8303AUD $11,966*

*Converted price in your currency provided by Open Exchange Rates. Exchange rates are subject to continuous change. Neither realestate.com.au nor its affiliates guarantee that the conversion reflects current conversion rates and are not responsible for any inaccuracies. realestate.com.au recommends that you independently verify any information before relying on it.

Contact Agent
Alisan Lohan-Conway
Alisan Lohan-Conway Properties
Post Office Box 2670 , Edgartown, MA 02539
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Alisan Lohan-Conway
Post Office Box 2670 , Edgartown, MA 02539
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      Property ID: 110107243571

      Original Property ID: 3yd-LNKMVMA-44300
      Data provided by LINK Martha’s Vineyard, MLS #: 44300
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