34 Windemere Rd

Oak Bluffs, MA 02557

$2,579,000
Price
4
Beds
1,399 Sq. Ft.
$1,843 / Sq. Ft.
1,399
Sq. Ft.
$1,843
per Sq. Ft.
Get preapproved with Rocket Mortgage1
a front view of a house with a yard
a kitchen with stainless steel appliances granite countertop a stove and a white cabinets
a kitchen with stainless steel appliances granite countertop a stove top oven a sink and a refrigerator
a living room with furniture and a fireplace
a living room with furniture a couch and a bookshelf
a dining room with furniture a chandelier and wooden floor
a living room with furniture and floor to ceiling windows
a view of a dining room with furniture window and wooden floor
a bedroom with a bed and a view of bedroom
a white toilet sitting next to a bath tub
a bathroom with a sink a bathtub and a shower
a bedroom with a bed and wooden floor
a view of a livingroom with wooden floor and stairs
a view of a room with wooden floor staircase and a bathroom
a bed sitting in a bedroom next to a window
a bedroom with a bed and a couch
a bedroom with a bed and couch
a bathroom with a granite countertop toilet sink and mirror
a living room with furniture and a large window
a bathroom with a sink and a mirror
a living room with a bed and a painting on the wall
a view of swimming pool with an ocean view
a view of a house with a yard
a view of a house with backyard and sitting area
a view of a two chairs in the patio
a view of a house with a large window
a view of a backyard with lawn chairs and a fireplace
a view of a balcony with wooden floor
a view of a garden and lake view
a front view of a house with garden
a view of a house with a yard

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...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!
  1. Listed by Alisan Lohan-Conway • Alisan Lohan-Conway Properties

Property Details for 34 Windemere Road

Zoning
R1
View
D/Hrb
LISTING UPDATED: 04/13/2026 01:09 PM

Property Details for 34 Windemere Road

StatusActive
MLS #44300
Days on Market22
Taxes$8,303 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1910
Lot Size1.06 AC / 46,005 SF
CountyDukes County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Alisan Lohan-Conway Properties, Alisan Lohan-Conway
Add your commute

Building Information for 34 Windemere Road

Stories-Year Built1910Building Size-Lot Size1.06 AC / 46,005 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$13,679 per month

30 year fixed, 6.46% Interest

Principal and Interest

$12,987

Property Taxes

$692

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 34 Windemere Road

Summary
Location and General Information
  • Latitude: 41.4598791
  • Longitude: -70.5813219
  • Listing ods: PubBch, Deck, WViews, ScrPorch
  • MLS Area Major: 3
Taxes and HOA Information
  • Tax Assessed Value: $613,700.00
  • Tax Lot: 46.1, 46.2, 9 & 12
  • Tax Map Number: 6
  • Tax Other Annual Assessment Amount: $1,212,400.00
  • Tax Year: 2026
Parking
  • Parking Features: Yes - Off Street
Property
Lot Information
  • Lot Features: 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
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 64
  • Deed No: 1542
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2019
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town
Interior and Exterior Features
Exterior Features
  • Exterior Features: PubBch, Deck, WViews, ScrPorch
Interior Features
  • Main Level Bedrooms: 1
  • Other Structures: Shed. Gazebo. Mahogany outdoor shower. Boardwalk - Deeded access via boardwalk to Brush Pond.
  • Rooms Total: 7
  • Appliances: Stove: Yes - Frigidaire® Stainless Streel - Electric, Washer: Yes - Maytag® front loader
  • Fireplace Features: 1
  • Fireplace: No
  • Flooring: Hardwood
  • Foundation Details: Block
  • Furnished: Unfurnished
  • Heating: Heat Pump
  • Interior Features: AC,Ins,Irr,OSh, 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.

Property History for 34 Windemere Road

DateEvent & SourcePriceAppreciation
Apr 12, 2026

Listed (Active)

LINK #44300

$2,579,000—
Apr 10, 2026

Canceled

LINK #40654

$2,700,000—
Apr 3, 2023

Listed (Active)

LINK #40654

$2,950,000—
DateEvent & SourcePrice
04/12/2026

Listed (Active)

LINK #44300

$2,579,000
04/10/2026

Canceled

LINK #40654

$2,700,000
04/03/2023

Listed (Active)

LINK #40654

$2,950,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 34 Windemere Road

Taxable ValueLand$956,200Additions$607,300Total$1,563,500
Tax Record2025$7,896 ($658 / month)
Home Facts
Beds4Baths1.5Total Finished SqFt1,399 SqFtAbove Grade Finished SqFt1,399 SqFtStories2Lot Size10,020 SqFtStyleSingle Family ResidenceYear Built1910Year Renovated2005CountyDUKESAPNOAKB M:0006 B:0046 L:001

Schools near 34 Windemere Road

This home is within Oak Bluffs School District.
Rating
School
Type
Grades
Distance
Oak Bluffs Elementary School
Public - PK to 8
Martha's Vineyard Regional High School
Public - 9 to 12
Vineyard Montessori School
Private - PK to 7
Rating
School
Distance
Oak Bluffs Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

Vineyard Montessori School
PrivatePK to 7

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 34 Windemere Road, Oak Bluffs, MA 02557

34 Windemere Road is a single family home for sale in Oak Bluffs, MA 02557. This property was listed for sale on April 12, 2026 by Alisan Lohan-Conway Properties, it's currently listed at $2,579,000. It has been on the market for a total of 22 days and was last sold on June 15, 2018. This listing's school districts are Oak Bluffs School District, Marthas Vineyard School District. Nearby schools include Oak Bluffs Elementary School, Martha's Vineyard Regional High School and Vineyard Montessori School. 34 Windemere Road is a 4-bed, 2-bath, 1,399 sqft single family home built in 1910.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.