52 Windsor Dr

1,410 Sq. Ft.
$848 / Sq. Ft.
1,410
Sq. Ft.
$848
per Sq. Ft.

Description

Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The full basement offers generous storage and in-home laundry. BOH says four bedrooms are possible if septic...Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The full basement offers generous storage and in-home laundry. BOH says four bedrooms are possible if septic is upgraded. Current three bedroom septic passed Title V. Easy access to multiple towns and Island beaches, this home puts the best of Martha's Vineyard at your doorstep.
  1. Listed by Emma Kennedy • Sandpiper Realty, Inc.

Property Details for 52 Windsor Drive

Town
Edgartown
MLS Area
Edgartown
Area
MA-Edgartown-Edgartown, MA-Edgartown
Architectural Style
Colonial
Style
Colonial
Garage Spaces
0
Open Parking Spaces
3.00
Parking Spaces Total
3
LISTING UPDATED: 03/25/2026 10:58 AM

Property Details for 52 Windsor Drive

StatusActive
MLS #73489622
Days on Market9
Taxes$2,541 / year
HOA Fees$175 / year
Compass TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1985
CountyDukes County

Location

Listing Courtesy of Sandpiper Realty, Inc., Emma Kennedy
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Building Information for 52 Windsor Drive

Stories-Year Built1985Building Size-Lot Size0.50 AC / 21,859 SF

Payment Calculator

$6,026 per month

30 year fixed, 6.11% Interest

Principal and Interest

$5,799

Property Taxes

$212

HOA Dues

$15

The Payment Calculator is for illustrative purposes only.

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Property Information for 52 Windsor Drive

General Details
Property Details
  • Building Area Units: Square Feet
  • Living Area: 1410.0
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Electric Water Heater, Range, Dishwasher, Refrigerator, Washer, Dryer
  • Basement Features: Full
  • Num of Baths: 2.0
  • Num of Full Baths: 2
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Integer: 2
  • FireplaceFeatures: 0
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Wood, Carpet
  • Interior Features: OSh, Floor 1: Bright open living, kitchen, dining area, leading to a private back deck. One bedroom and full bath complete the first floor., Floor 2: The second floor has two bedrooms and one full bath.
  • Main Level Bedrooms: 1
  • SpaYN: No
Exterior Features
  • Exterior Features: Deck - Wood, Outdoor Shower
  • Exterior Features: Outdoor Shower, Deck - Wood
  • Lot Description: Wooded
  • Patio And Porch Features: Deck - Wood
  • Roof Material: Shingle
  • View: None
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Parking Features: Yes
Utilities
  • Cooling: None
  • Cooling: No
  • Heating: Electric Baseboard
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: Cbl
  • Water: Public
Property Information
Property Info
  • UFFI: Unknown
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
Tax Information
  • Tax ID: 10/99.63,3768358
  • Assessments: $1,084,800
  • Block: 99.63
  • Book: 64
  • Lot: 99.63
  • Map: 10
  • Tax Year: 2026
  • Zoning: R60
Building / Association Information
Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
Complex & Association Information
  • Association Fee Frequency: Annually
  • Adult Community: No

Property History for 52 Windsor Drive

DateEvent & SourcePriceAppreciation
Mar 21, 2026

Listed (Active)

LINK #44183

$1,195,000
Mar 20, 2026

Listed (Active)

MLS PIN #73489622

$1,195,000
Apr 27, 2022

Canceled

LINK #18840

Nov 5, 2020

Price Change

LINK #10809

$575,000
Jul 3, 2009

Listed (Active)

LINK #18840

Dec 28, 2005

Sold (Public Record)

Public Record #190603123

$565,000

+26.9% / yr

Dec 28, 2005

Sold

LINK #10809

$565,000
Dec 15, 2005

Expired

Cape Cod & Islands Multiple Listing Service #20507839

$575,000
Dec 15, 2005

Expired

Martha's Vineyard MLS #20507839

Jul 18, 2005

Listed (Active)

LINK #10809

$575,000
Jul 15, 2005

Listed (Active)

Cape Cod & Islands Multiple Listing Service #20507839

$559,000
Jul 15, 2005

Listed (Active)

Martha's Vineyard MLS #20507839

$559,000
Sep 27, 2002

Sold (Public Record)

Public Record #105064991

$260,455
DateEvent & SourcePrice
03/21/2026

Listed (Active)

LINK #44183

$1,195,000
03/20/2026

Listed (Active)

MLS PIN #73489622

$1,195,000
04/27/2022

Canceled

LINK #18840

11/05/2020

Price Change

LINK #10809

$575,000
07/03/2009

Listed (Active)

LINK #18840

12/28/2005

Sold (Public Record)

Public Record #190603123

$565,000

+26.9% / yr

12/28/2005

Sold

LINK #10809

$565,000
12/15/2005

Expired

Cape Cod & Islands Multiple Listing Service #20507839

$575,000
12/15/2005

Expired

Martha's Vineyard MLS #20507839

07/18/2005

Listed (Active)

LINK #10809

$575,000
07/15/2005

Listed (Active)

Cape Cod & Islands Multiple Listing Service #20507839

$559,000
07/15/2005

Listed (Active)

Martha's Vineyard MLS #20507839

$559,000
09/27/2002

Sold (Public Record)

Public Record #105064991

$260,455

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

Public Records for 52 Windsor Drive

Taxable ValueLand$333,500Additions$538,700Total$872,200
Tax Record2025$2,311 ($193 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,410 SqFtAbove Grade Finished SqFt1,410 SqFtStories2Lot Size21,859 SqFtStyleSingle Family ResidenceYear Built1985CountyDUKESAPNEDGA M:0010 B:0099 L:63

Schools near 52 Windsor Drive

This home is within Edgartown School District.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Rating
School
Distance
Edgartown Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

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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52 Windsor Drive is a single family home for sale in Edgartown, MA 02539. This property was listed for sale on March 20, 2026 by Sandpiper Realty, Inc., it's currently listed at $1,195,000. It has been on the market for a total of 9 days and was last sold on December 28, 2005. This listing's school districts are Edgartown School District, Marthas Vineyard School District. Nearby schools include Edgartown Elementary School and Martha's Vineyard Regional High School. 52 Windsor Drive is a 3-bed, 2-bath, 1,410 sqft single family home built in 1985.

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 Sandpiper Realty, Inc., Emma Kennedy

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.