Single Family Home For Sale in Oak Bluffs #44300

Single Family Homes - Oak Bluffs, East Chop Lagoon/Harbor Oak Bluffs | 34 Windemere Road, Oak Bluffs MA 02557
  • Rooms/BD
    7/4
  • Bath(s)
    2
  • SqF
    1,399 ft²
  • Price
    $2,579,000

Property For Sale Description

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. Rentals in place for 2026 Summer Season!

Floor 1: Kitchen with laundry area, living room with fireplace, water view dining room leading to huge deck with views, ground floor bedroom, shared full bathroom, large enclosed porch used for additional dining and sitting room/tv area.

Floor 2: Primary bedroom with views over The Lagoon and distant view of Vineyard Haven Harbor with private bathroom. Two guest bedrooms with a full shared bathroom.

Basement: Full basement with utilities and plenty of room for storage.

Other Buildings:

Second Dwelling: PSd

Lot: Yes - Easement on Lot #4 (Map: 6/ Lot:12) of 256sq.ft. for parking/fence for 45 Windemere Road. View Easement for 34 Windemere Road over 00 & 38 Windemere Road.,Large - 1+acre of land over 4 lots - 3 contiguous, 1 across the street

Amenities

Kitchen amenities
Stove / Oven
Indoor amenities
A/C - Units/Splits
Washer / Dryer
Outdoor amenities
Deck
Irrigation
Outdoor Shower
Porch

©2026 LINK, All Rights Reserved. Not responsible for misinformation or typographical errors. Prices are subject to change without notice. Listed by: Alisan Lohan-Conway Properties

Inquire about this property

  • Listing ID: 44300
  • Year Built: 1910
  • Flooring:
  • Foundation: Block
  • Water: Town
  • Heating: Heat Pump