34 Windemere Rd

$2,700,000
Price
4
Beds
1,399 Sq. Ft.
$1,930 / Sq. Ft.
1,399
Sq. Ft.
$1,930
per Sq. Ft.

Description

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor...Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2026 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.
  1. Listed by JoJo Lambert • Island Home Realty Inc.

Property Details for 34 Windemere Road

Zoning
R1
View
None, D/Pnd
LISTING UPDATED: 12/11/2025 02:42 AM

Property Details for 34 Windemere Road

StatusActive
MLS #40654
Days on Market946
Taxes$8,297 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1910
Lot Size0.72 AC / 31,363 SF
CountyDukes County

Location

Listing Courtesy of Island Home Realty Inc., JoJo Lambert
Add your commute

Building Information for 34 Windemere Road

Stories-Year Built1910Building Size-Lot Size0.72 AC / 31,363 SF

Payment Calculator

$14,033 per month

30 year fixed, 6.28% Interest

Principal and Interest

$13,342

Property Taxes

$691

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 34 Windemere Road

Summary
Location and General Information
  • Latitude: 41.4598608
  • Longitude: -70.5813158
  • GeoLocked: No
  • Listing ods: Deck, PubBch, WViews
  • MLS Area Major: 3
Taxes and HOA Information
  • Tax Assessed Value: $600,000.00
  • Tax Lot: 46-1 46-2 & 9-0,
  • Tax Map Number: 6
  • Tax Other Annual Assessment Amount: $971,400.00
  • Tax Year: 2023
Parking
  • Parking Features: Yes Off street
Property
Lot Information
  • Loft: 0
  • Lot Features: Deeded Access is over the next door neighbors yard to the boardwalk to the Lagoon/beach, Expansive Front yard Waterviews with access to the water
  • Number Of Lots: 0
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 44
  • 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: Deck, PubBch, WViews
Interior Features
  • Septic Bedrooms: 0
  • Main Level Bedrooms: 1
  • Other Structures: Shed & Gazebo
  • Rooms Total: 7
  • Appliances: Stove: Yes, Washer: Yes
  • Fireplace Features: 1
  • Fireplace: No
  • Flooring: 2
  • Foundation Details: Yes concrete blocks
  • Furnished: Partially
  • Heating: Heat Pump
  • Interior Features: AC,Ins,Irr,Media,OSh, Floor 1: Open floor plan living/dining room. Sunroom, Kitchen, Queen bedroom, a full bath, and a Laundry section in the kitchen. Living/Dining/Sunroom/kitchen all have waterviews., Floor 2: Second floor, Three bedrooms and 2 full bath. Master is a Queen suite with water view, Bunk bed guest bedroom waterview, and the other guest bedroom is Twins which share the guest bath.
  • Beds Plus: 0

Property History for 34 Windemere Road

DateEvent & SourcePriceAppreciation
Apr 3, 2023

Listed (Active)

LINK #40654

$2,950,000—
Dec 15, 2022

Canceled

LINK #39595

$3,200,000—
May 13, 2022

Listed (Active)

LINK #39595

$3,200,000—
Jan 22, 2022

Canceled

LINK #38803

$3,999,000—
Oct 7, 2021

Listed (Active)

LINK #38803

$3,999,000—
Jun 15, 2018

Sold

Martha's Vineyard MLS #21804849

$1,075,000—
Jun 15, 2018

Sold

LINK #33914

$1,075,000—
Nov 16, 2017

Expired

MLS PIN #72221830

—
Sep 1, 2017

Listed (Active)

MLS PIN #72221830

—
May 23, 2017

Canceled

LINK #30531

$2,000,000—
Dec 19, 2016

Canceled

MLS PIN #72033596

$1,690,000—
Jul 6, 2016

Listed (Active)

MLS PIN #72033596

$1,690,000—
Jul 6, 2016

Listed (Active)

LINK #30531

$1,690,000—
Feb 25, 2014

Canceled

LINK #18453

$1,395,000—
Mar 5, 2011

Expired

Cape Cod & Islands Multiple Listing Service #21005101

$2,100,000—
Mar 5, 2011

Expired

Martha's Vineyard MLS #21005101

—
Mar 9, 2009

Listed (Active)

LINK #18453

$2,100,000—
Mar 5, 2009

Listed (Active)

Martha's Vineyard MLS #21005101

$2,100,000—
Mar 5, 2009

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21005101

$2,100,000—
Dec 11, 2006

Sold (Public Record)

Public Record #326419764

$1—
Dec 11, 2006

Sold (Public Record)

Public Record #326419766

$1

-75.9% / yr

Jan 20, 1998

Sold (Public Record)

Public Record #89171553

$309,500—
DateEvent & SourcePrice
04/03/2023

Listed (Active)

LINK #40654

$2,950,000
12/15/2022

Canceled

LINK #39595

$3,200,000
05/13/2022

Listed (Active)

LINK #39595

$3,200,000
01/22/2022

Canceled

LINK #38803

$3,999,000
10/07/2021

Listed (Active)

LINK #38803

$3,999,000
06/15/2018

Sold

Martha's Vineyard MLS #21804849

$1,075,000
06/15/2018

Sold

LINK #33914

$1,075,000
11/16/2017

Expired

MLS PIN #72221830

—
09/01/2017

Listed (Active)

MLS PIN #72221830

—
05/23/2017

Canceled

LINK #30531

$2,000,000
12/19/2016

Canceled

MLS PIN #72033596

$1,690,000
07/06/2016

Listed (Active)

MLS PIN #72033596

$1,690,000
07/06/2016

Listed (Active)

LINK #30531

$1,690,000
02/25/2014

Canceled

LINK #18453

$1,395,000
03/05/2011

Expired

Cape Cod & Islands Multiple Listing Service #21005101

$2,100,000
03/05/2011

Expired

Martha's Vineyard MLS #21005101

—
03/09/2009

Listed (Active)

LINK #18453

$2,100,000
03/05/2009

Listed (Active)

Martha's Vineyard MLS #21005101

$2,100,000
03/05/2009

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21005101

$2,100,000
12/11/2006

Sold (Public Record)

Public Record #326419764

$1
12/11/2006

Sold (Public Record)

Public Record #326419766

$1

-75.9% / yr

01/20/1998

Sold (Public Record)

Public Record #89171553

$309,500

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
Public - PK to 8
Public - 9 to 12
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

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34 Windemere Road is a single family home for sale in Oak Bluffs, MA 02557. This property was listed for sale on April 3, 2023 by Island Home Realty Inc., it's currently listed at $2,700,000. It has been on the market for a total of 946 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, 3-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.

Listing Courtesy of Island Home Realty Inc., JoJo Lambert

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.