Last Sold Price
2 beds2 baths2,192 sqft$0/sqft
27 Windemere Rd, Oak Bluffs, MA 02557

Property Details for 27 Windemere Road

Status
MLS #
-
Days on Market
-
Taxes
-
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
Single Family
Year Built
1974
Lot Size
-

Recent comparable sales

Median sold price

$1,310,000

Avg days on market

89

Sale-to-list ratio

89.8%

Oak Bluffs, MA

9 comparable properties found

$1,150,000 | 66 Barnes Road, Oak Bluffs, MA 02557
1/31
1

$1,150,000

Sold 07/20/26

2
Bedrooms
1,752
Square Feet
0.11
Acres
a front view of a house with a yard and garage
1/27
2

$1,900,000

Sold 02/09/26

2
Bedrooms
2,137
Square Feet
0.30
Acres
a front view of a house with swimming pool
1/42
3

$1,310,000

Sold 08/18/25

3
Bedrooms
1,964
Square Feet
0.36
Acres
a view of a house with swimming pool and a yard
1/43
4

$1,530,000

Sold 01/13/26

3
Bedrooms
2,015
Square Feet
0.25
Acres
$1,270,000 | 60 Prospect Avenue, Oak Bluffs, MA 02557
1/29
5

$1,270,000

Sold 05/23/25

3
Bedrooms
2,192
Square Feet
0.34
Acres
a front view of house with yard and green space
1/2
6

$2,000,000

Sold 10/25/24

2
Bedrooms
1,507
Square Feet
1.2
Acres
a view of a house with a street
1/27
7

$1,875,000

Sold 05/13/26

3
Bedrooms
2,215
Square Feet
0.43
Acres
a view of lake
1/2
8

$1,100,000

Sold 06/17/25

2
Bedrooms
2,912
Square Feet
0.27
Acres
an aerial view of a house with yard swimming pool and outdoor seating
1/48
9

$1,162,500

Sold 01/10/25

3
Bedrooms
2,356
Square Feet
0.29
Acres

Location

Add your commute

Building Information for 27 Windemere Road

Stories1Year Built1974Building Size-Lot Size-

Payment Calculator

$509 per month

30 year fixed, 6.55% Interest

Principal and Interest

$0

Property Taxes

$509

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property History for 27 Windemere Road

DateEvent & SourcePriceAppreciation
Mar 1, 2011

Sold (Public Record)

Public Record #326418936

$1
DateEvent & SourcePrice
03/01/2011

Sold (Public Record)

Public Record #326418936

$1

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

Public Records for 27 Windemere Road

Taxable ValueLand$812,400Additions$396,100Total$1,208,500
Tax Record2025$6,103 ($509 / month)
Home Facts
Beds2Baths2Total Finished SqFt2,192 SqFtAbove Grade Finished SqFt2,192 SqFtStories1Lot Size7,863 SqFtStyleSingle Family ResidenceYear Built1974Year Renovated1998CountyDUKESAPNOAKB M:0006 B:0042 L:000

Schools near 27 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.

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Listed By Compass

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 27 Windemere Road, Oak Bluffs, MA 02557
$1
2
2
2,192
3
2,761
12,079
3
2,897
12,197
5
2
2,125
5,227
5,227
2,614

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

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.