MLS #44300
Oak Bluffs Real Estate

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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 groundvfloor 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 they are a combined total of just over an acre of land. Included is Deeded Access via a boardwalk leading to Brush Pond, with wonderful views. Directly in front of the property lies a sandy State 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 separate purchase. Excellent Rental History. Rentals in place for 2026 Summer Season!
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Price:  $2,579,000
34 Windemere Road
Oak Bluffs, 02568
Type: Single Family
Water Frontage: Pondfront
Beds: 4
Baths: 2.0
Lot Size: 1.06 acres
Square Footage: 1399 sqft.
Area
Oak Bluffs
Subdivision
Lagoon/Harbor
Waterfrontage
Pondfront
Zoning
R1
Water
Town
Sewer
Septic
Year Built
1910
Year Renovated
2019
Second Dwelling
Potential
Furnished
Un-Furnished
Rooms
7
First Floor Bedrooms
1
Fireplaces
1
Flooring
Hardwood
Heating
Heat Pump
Yard
Large - 1+acre of land over 4 lots - 3 contiguous, 1 across the street
Foundation
Block
Outdoor Spaces
Beach Access - Public
Parking
Yes - Off Street
Dishwasher
Yes - Stainless Steel
Dryer
Yes - Maytag® front loader
Refrigerator
Yes - Stainless Steel
Stove
Yes - Frigidaire® Stainless Streel - Electric
TV
Cable
Washer
Yes - Maytag® front loader
Listing Agent
Lohan-Conway, Alisan
Listing Office
Alisan Lohan-Conway Properties