Oak Bluffs, MA 0255734 Windemere Road

$2,579,000

34 Windemere Road Oak Bluffs, MA - Image 134 Windemere Road Oak Bluffs, MA - Image 234 Windemere Road Oak Bluffs, MA - Image 334 Windemere Road Oak Bluffs, MA - Image 4
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Presented By: Alisan Lohan-Conway with Alisan Lohan-Conway Properties
  • MLS# 44300
  • 04/12/2026
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  • Beds • 4
  • Full/Half Baths • 2 / 0
  • Acres • 1.0561

Home Details

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.
Presented By: Alisan Lohan-Conway with Alisan Lohan-Conway Properties

Interior Features for 34 Windemere Road

Total Bedrooms4
Full Baths2
Half Baths0
BasementFull basement with utilities and plenty of room for storage.
FlooringHardwood
HeatingHeat Pump
AppliancesStove: Yes - Frigidaire® Stainless Streel - Electric, Washer: Yes - Maytag® front loader

General for 34 Windemere Road

Property Type1 Family
Property SubtypeSingle Family Residence
StatusActive
Year Built1910
Total Rooms7
SewerSeptic Tank
MLS Area3
Tax Annual Amount8303
Tax Assessed Value613700
Tax Year2026

Exterior for 34 Windemere Road

Lot Size Acres1.0561
Lot Size Square Feet46005
Exterior FeaturesPubBch, Deck, WViews, ScrPorch
Parking FeaturesYes - Off Street
Water SourceTown
ViewD/Hrb

Additional Details

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Listing information is provided by LINK MLS and is deemed reliable but not guaranteed. Listing courtesy of Alisan Lohan-Conway Properties.