52 Windsor Dr, Edgartown, MA 02539
Property image
Property image
SOLD
MAY 7, 2026

$1,132,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,410 sqft (on 0.50 acres)

52 Windsor Dr, Edgartown, MA 02539

Est. Refi. Payment $6,617/mo*
Refinance Your Home
Currently Off Market - Sold May 7, 2026 for $1,125,000 (6% below list price)

Home Value

Trulia Estimate
$1.13M
Since last month
Decreased$600 (-0.1%)
Since last year
Increased$43K (+3.9%)
Since last sale
Increased$8K (+0.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +115% in the last 10 years
MonthEstimated value
2026
September 2026$1.13M
August 2026$1.13M
July 2026$1.13M
June 2026$1.13M
May 2026$1.13M
April 2026$1.15M
March 2026$1.18M
February 2026$1.09M
January 2026$1.09M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
60 Windsor Dr, Edgartown, MA
0.08
Single-Family Home
$1,575,000
11/24/25
4
2
1,666
18 Windsor Dr, Edgartown, MA
0.31
Single-Family Home
$1,150,000
05/08/26
3
2
1,294
1 Dodgers Hole Road, Edgartown, MA
0.52
Single-Family Home
$1,050,000
09/11/26
4
2
1,513
11 Flamingo Dr, Edgartown, MA
0.57
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
16 Majors Cove Ln, Edgartown, MA
0.55
Single-Family Home
$1,350,000
11/20/25
3
2
1,965
2 Flamingo Dr, Edgartown, MA
0.47
Single-Family Home
$995,000
11/06/25
3
1
990
1 Edgewood Dr, Edgartown, MA
0.27
Single-Family Home
$1,280,000
12/12/25
3
2
1,604
30 Teaberry Ln, Edgartown, MA
0.96
Single-Family Home
$1,135,000
10/31/25
3
2
1,344
112 3rd St N, Edgartown, MA
0.88
Single-Family Home
$1,175,000
04/22/26
3
2
1,196

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
73 Dodgers Hole Rd, Edgartown, MA 02539
0.03
$1,440,400
3
2.5
2,019
Off Market
1 Thames Ct, Edgartown, MA 02539
0.05
$1,941,600
4
3
3,270
Off Market
55 Windsor Dr, Edgartown, MA 02539
0.05
$1,409,400
3
2
1,568
Off Market
60 Windsor Dr, Edgartown, MA 02539
0.08
$1,575,000
4
2
1,666
Recently Sold
46 Windsor Dr, Edgartown, MA 02539
0.08
$1,255,900
3
2
1,520
Off Market
61 Dodgers Hole Road, Edgartown, MA 02539
0.08
$1,521,500
3
2
2,311
Off Market
38 Edgewood Dr, Edgartown, MA 02539
0.12
$1,803,800
3
2.5
2,576
Off Market
40 Edgewood Dr, Edgartown, MA 02539
0.13
$2,996,700
3
4.5
2,912
Off Market
72 Windsor Dr, Edgartown, MA 02539
0.17
-
-
-
-
Off Market
23 Edgewood Dr, Edgartown, MA 02539
0.16
$1,350,100
3
1.5
1,439
Off Market
41 Dodgers Hole Rd, Edgartown, MA 02539
0.25
$1,583,400
3
2
1,326
Off Market

Local Information

  • Map ViewExplore the area around 52 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1985
0.5 acre lot
1,410 sqft
$798/sqft
HOA $15/mo

About this House

What's unique:Private deckBright open-plan main levelFirst-floor bedroom and bathWooded lot
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.
52 Windsor Dr, Edgartown, MA 02539 is a 3 bedroom, 2 bathroom, 1,410 sqft single-family home built in 1985. It last sold for $1,125,000 on May 7, 2026 (6% below the $1,195,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,132,400, with a rent estimate of $4,641/month.
Last check for updates: about 3 hours ago
Listed by Emma Kennedy
Sandpiper Realty
Bought with: Compass | The O'Hanlon Group
Source: LINK, MLS#44183

Home Details for 52 Windsor Dr

Interior Features

Interior Details
Basement: Full BasementNumber of Rooms: 5
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 1Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1410 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: 0
Windows, Doors, Floors & Walls
Flooring: 2
Levels, Entrance, & Accessibility
Floors: 2
View
No ViewView: None

Exterior Features

Exterior Home Features
Exterior: PubBchFoundation: Full Basement
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Yes
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $1,195,000Price Per Sqft: $798/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Edgartown

Building

Building Area
Building Area: 1410 Square Feet

HOA

Has an HOAHOA Fee: $175/Annually

Lot Information

Lot Area: 0.50 acres

Offer

Listing Agreement Type: E

Rental Terms, Policies & Fees

Furnished

Miscellaneous

BasementMls Number: 44183

Price and Tax history

DateEventPrice
May 7, 2026
Source: LINK #44183
Sold
$1,125,000
Apr 11, 2026
Source: LINK #44183
Pending
$1,195,000
Mar 20, 2026
Source: MLS PIN #73489622
Listed For Sale
$1,195,000
Dec 28, 2005
Source: LINK #10809
Sold
$565,000
Sep 27, 2002
Source: N/A
Sold
$260,455

Market trends in Edgartown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
68
1MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Edgartown

At least 17 Trulia users voted on each feature.

  • 89 % Say they plan to stay for at least 5 years

  • 85 % Say people would walk alone at night

  • 81 % Say it's dog friendly

  • 76 % Say yards are well-kept

  • 75 % Say car is needed

  • 70 % Say it's quiet

  • 68 % Say there's wildlife

  • 67 % Say kids play outside

  • 60 % Say it's walkable to restaurants

  • 59 % Say neighbors are friendly

  • 56 % Say there's holiday spirit

  • 52 % Say it's walkable to grocery stores

  • 52 % Say parking is easy

  • 46 % Say there are sidewalks

  • 46 % Say streets are well-lit

  • 36 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Some restaurants are dog-friendly but many are not. During the summer months, many shops provide water bowls outside "
    0
    Flag
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
    2
    Flag
  • Adriannen1114
    "Beautiful place! Lovely neighborhoods and very safe. The kind of place you want to live and or visit. Absolutely lovely. Everywhere you go there is another amazing fun spot. "
    0
    Flag
  • Olivia G.
    "I live in Edgartown and I work in OB. I work 7 miles from my home and I drive down one of the most beautiful roads I’ve ever seen. "
    0
    Flag
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
    0
    Flag
  • Megan S.
    "I leave close to e everything summer time is a cool time to enjoy it bad Martha’s live music winter very quiet and private "
    0
    Flag
  • Megan S.
    "I live in good neighborhoods very close to donoramas peaceful location very close to everything I need I don’t know much about people round but This is my opinion about it "
    5
    Flag
  • Mvrock17
    "My neighborhood is really great and has bike path beautiful roads in trees laying it all the way down into town it seems like every year improvements are made to make it better right now so"
    4
    Flag
  • Unspecified
    "Business area but after five gets quiet. Very close to everything you need is walking distance. Busses are near to go to the other towns. Short walk to a beach. "
    0
    Flag
  • Frank M. M.
    "I live and work in Edgartown and know this to be one of the top areas vacationers like to rent in. Edgartown Estates is well managed, clean, and known to be a "go to" place for vacationers wanting the Beach and In-town experience with easy access."
    0
    Flag

LGBTQ Local Legal Protections

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-23 10:09:46 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 52 Windsor Dr

  • What is 52 Windsor Dr estimated to be worth?
    Trulia's estimated value for 52 Windsor Dr in Edgartown, MA is $1,132,400.
  • What is the price history for 52 Windsor Dr?
    52 Windsor Dr in Edgartown, MA last sold for $1,125,000 in May 2026.
  • Is Edgartown a buyer's or seller's market?
    Edgartown is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Edgartown?
    Residents describe Edgartown, MA as established, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Edgartown, MA.
  • How big is the lot at 52 Windsor Dr?
    The lot at 52 Windsor Dr in Edgartown, MA is about 0.50 acres (21,859 sq ft).
  • Does 52 Windsor Dr have parking?
    Yes, 52 Windsor Dr in Edgartown, MA has on-site parking.

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