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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 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!

FIRST FLOOR DESCRIPTION
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.

SECOND FLOOR DESCRIPTION
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 DESCRIPTION
Full basement with utilities and plenty of room for storage.

OTHER BUILDINGS
Shed. Gazebo. Mahogany outdoor shower. Boardwalk - Deeded access via boardwalk to Brush Pond.

SECOND DWELLING
P/Sd

PARKING
Yes - Off Street

Single Family Residence
Oak Bluffs
34 Windemere Road
$2,579,000.00

LINK ID: 44300
Bedrooms: 4
Baths: 2
Rooms: 7
Living Space: 1399
Acreage: 1.0561
Water Frontage: Pnd
1st Floor Bedrooms 1

TO INQUIRE ABOUT THIS LISTING CLICK HERE.

Outdoor Spaces: Beach Access - Public, Deck, Water Views, Porch Screen,
Features: Cental A/C, Insulation, Irrigation, Outdoor Shower
Year Built: 1910
Year Renovated: 2019
Second Dwelling: Existing
Zoning: R1
Water: Town
Sewer: Septic Tank
Lead Paint: Unknown
Foundation : Block
Heat: Heat Pump
Fireplaces: 1
Yard Type: 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
Flooring: Hardwood
Stove: Yes - Frigidaire® Stainless Streel - Electric
Washer: Yes - Maytag® front loader
TV: Cable
©2026 LINK, All Rights Reserved
Not responsible for misinformation or typographical errors. Prices are subject to change without notice.
 

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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals

PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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