60 Windsor Dr, Edgartown, MA 02539
Property image
Property image
SOLD
NOV 24, 2025

$1,616,500

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,666 sqft (on 0.51 acres)

60 Windsor Dr, Edgartown, MA 02539

Est. Refi. Payment $9,353/mo*
Refinance Your Home
Currently Off Market - Sold Nov 24, 2025 for $1,575,000 (5% below list price)

Home Value

Trulia Estimate
$1.62M
Since last month
Increased$14K (+0.9%)
Since last year
Increased$63K (+4%)
Since last sale
Increased$42K (+2.6%)
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 +164% in the last 10 years
MonthEstimated value
2026
September 2026$1.62M
August 2026$1.61M
July 2026$1.6M
June 2026$1.6M
May 2026$1.6M
April 2026$1.59M
March 2026$1.6M
February 2026$1.59M
January 2026$1.58M
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
52 Windsor Dr, Edgartown, MA
0.08
Single-Family Home
$1,125,000
05/07/26
3
2
1,410
18 Windsor Dr, Edgartown, MA
0.39
Single-Family Home
$1,150,000
05/08/26
3
2
1,294
11 Flamingo Dr, Edgartown, MA
0.64
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
1 Dodgers Hole Road, Edgartown, MA
0.59
Single-Family Home
$1,050,000
09/11/26
4
2
1,513
63 Saddle Club Rd, Edgartown, MA
0.58
Single-Family Home
$1,550,000
04/09/26
4
2.5
2,291
68 20th St S, Edgartown, MA
0.57
Single-Family Home
$1,500,000
03/30/26
4
3
1,975
16 Majors Cove Ln, Edgartown, MA
0.62
Single-Family Home
$1,350,000
11/20/25
3
2
1,965
32 Flamingo Dr, Edgartown, MA
0.54
Single-Family Home
$1,817,500
02/27/26
5
3
2,432
1 Edgewood Dr, Edgartown, MA
0.32
Single-Family Home
$1,280,000
12/12/25
3
2
1,604

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
0.06
$1,440,400
3
2.5
2,019
Off Market
55 Windsor Dr, Edgartown, MA 02539
0.05
$1,394,400
3
2
1,568
Off Market
52 Windsor Dr, Edgartown, MA 02539
0.08
$1,125,000
3
2
1,410
Recently Sold
72 Windsor Dr, Edgartown, MA 02539
0.09
-
-
-
-
Off Market
1 Thames Ct, Edgartown, MA 02539
0.10
$1,941,600
4
3
3,270
Off Market
38 Edgewood Dr, Edgartown, MA 02539
0.10
$1,796,900
3
2.5
2,576
Off Market
40 Edgewood Dr, Edgartown, MA 02539
0.10
$2,996,700
3
4.5
2,912
Off Market
46 Windsor Dr, Edgartown, MA 02539
0.15
$1,262,300
3
2
1,520
Off Market
61 Dodgers Hole Road, Edgartown, MA 02539
0.16
$1,522,300
3
2
2,311
Off Market
23 Edgewood Dr, Edgartown, MA 02539
0.20
$1,345,700
3
1.5
1,439
Off Market
10 Woodhaven Drive, Edgartown, MA 02539
0.22
$2,650,000
3
2.5
2,876
For Sale

Local Information

  • Map ViewExplore the area around 60 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
0.51 acre lot
1,666 sqft
$945/sqft
HOA $14/mo

About this House

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.
60 Windsor Dr, Edgartown, MA 02539 is a 4 bedroom, 2 bathroom, 1,666 sqft single-family home built in 1996. It last sold for $1,575,000 on Nov 24, 2025 (5% below the $1,650,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,616,500, with a rent estimate of $5,277/month.
Last check for updates: about 3 hours ago
Listed by Alyssa Halisky
Wallace & Co. Sotheby's
Bought with: Peyton Wallace, Studio Realty
Source: LINK, MLS#43007

Home Details for 60 Windsor Dr

Interior Features

Interior Details
Basement: Full unfinished basement with laundryNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1666 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: 5 Burner - Electric Frigidaire Stove, Washer: Yes - Lower Level
Heating & Cooling
Heating: GFHWNo CoolingHas HeatingHeating Fuel: GFHW
Fireplace & Spa
Fireplace: Yes
Windows, Doors, Floors & Walls
Flooring: 3
Levels, Entrance, & Accessibility
Floors: 3
View
Has a ViewView: None, Res

Exterior Features

Exterior Home Features
Other Structures: Outdoor ShowerExterior: Deck, Garden, PubBchFoundation: Full concrete foundationGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Stone driveway
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1996Year Renovated: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $1,650,000Price Per Sqft: $945/sqft

Active Status

MLS Status: S

Media

Location

Direction & Address
City: Edgartown

Building

Building Area
Building Area: 1666 Square Feet

HOA

HOA Fee Includes: Road AssociationHas an HOAHOA Fee: $165/Annually

Lot Information

Lot Area: 0.51 acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 43007

Price and Tax history

DateEventPrice
Nov 24, 2025
Source: LINK #43007
Sold
$1,575,000
Oct 28, 2025
Source: Martha's Vineyard MLS #32500079
Pending
$1,650,000
Oct 9, 2025
Source: Martha's Vineyard MLS #32500079
Contingent
$1,650,000
Mar 19, 2025
Source: Martha's Vineyard MLS #32500079
Listed For Sale
$1,650,000
Jan 6, 2025
Source: LINK #41963
ListingRemoved
$1,725,000

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: 2026-09-16 01:28:26 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 60 Windsor Dr

  • What is 60 Windsor Dr estimated to be worth?
    Trulia's estimated value for 60 Windsor Dr in Edgartown, MA is $1,616,500.
  • What is the price history for 60 Windsor Dr?
    60 Windsor Dr in Edgartown, MA last sold for $1,575,000 in November 2025.
  • 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.
  • Does 60 Windsor Dr have laundry facilities?
    Yes, 60 Windsor Dr in Edgartown, MA has laundry facilities.
  • How big is the lot at 60 Windsor Dr?
    The lot at 60 Windsor Dr in Edgartown, MA is about 0.51 acres (22,215 sq ft).

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