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4 Beds
2 Baths
1,399 sqft

$2,495,000

34 Windemere Road, Oak Bluffs MA, 02557

Price per sqft$1,783.42
Built in1910
Property size1,399 sqft
Property typeResidential

Overview

Active

Listed Apr 12, 2026

Updated 38 min ago

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, dining room 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 meets 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 may be purchased separately.

$16,599/mo

Est. mortgage payment based on a $2,495,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
44300

Interior Features

Bedrooms
4
Bathrooms
2
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.06 Acres

Other Property Details

Taxes
$8,303
Tax Frequency
Annually
View
Yes

 

Courtesy of Alisan Lohan-Conway Properties, Alisan Lohan-Conway

Based on information from LINK Martha's Vineyard as of 10/18/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 12:21 AM UTC, 10/18/2026

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