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

60 Windsor Dr
Edgartown, MA 02539

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

$1,575,000

Last Sold: Nov 24, 2025
5% below list $1.65M
$945/sqft
Est. Refi. Payment $8,571/mo*

$1,575,000

Last Sold: Nov 24, 2025
5% below list $1.65M
$945/sqft
Est. Refi. Payment $8,571/mo*
4 Beds
2 Baths
1,666 sqft
(on 0.51 acres)

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

Description

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). It is currently off market. The Trulia Estimate is $1,596,800, with a rent estimate of $5,214/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
$14/Monthly
Price/Sqft
$945/sqft
Listed
180+ days ago

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

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
Last check for updates: about 2 hours ago
Listed by Alyssa Halisky
Wallace & Co. Sotheby's
Bought with: Peyton Wallace, Studio Realty
Source: LINK, MLS#43007

Price History for 60 Windsor Dr

DatePriceEventSource
11/24/2025$1,575,000Sold
LINK #43007
10/28/2025$1,650,000PendingMartha's Vineyard MLS #32500079
10/09/2025$1,650,000ContingentMartha's Vineyard MLS #32500079
03/19/2025$1,650,000Listed For SaleMartha's Vineyard MLS #32500079
01/06/2025$1,725,000ListingRemovedLINK #41963
08/07/2024$1,725,000PriceChange
Martha's Vineyard MLS #32400124
10/19/2023$1,875,000Listed For SaleMLS PIN #73172283
10/12/2019$839,000ListingRemovedAgent Provided
06/14/2019$839,000PriceChange
Agent Provided
11/06/2018$849,000Listed For SaleN/A
03/01/1993$34,000Sold
N/A

Market trends in Edgartown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
64
1
MoM
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Property Tax and Assessment

Year2025
Tax$2,829
Assessment$1,067,600
Home facts updated by county records

Comparable Sales for 60 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Single-Family Home
$1,125,000
05/07/26
3
2
1,410
0.15
Single-Family Home
$1,450,000
08/26/25
3
2
2,311
0.10
Single-Family Home
$1,890,000
08/29/25
4
3
3,270
0.41
Single-Family Home
$1,320,000
08/29/25
3
2
1,450
0.39
Single-Family Home
$1,150,000
05/08/26
3
2
1,294
0.64
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
0.58
Single-Family Home
$1,550,000
04/09/26
4
2.5
2,291
0.57
Single-Family Home
$1,500,000
03/30/26
4
3
1,975
0.62
Single-Family Home
$1,350,000
11/20/25
3
2
1,965

Nearby homes

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Assigned Schools

These are the assigned schools for 60 Windsor Dr.
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 "
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
  • 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. "
  • 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. "
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
  • 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 "
  • 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 "
  • 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"
  • 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. "
  • 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."

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Apartments for Rent

Homes for sale near 60 Windsor Dr

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Off Market Homes Near 60 Windsor Dr

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-07-13 00:13:53 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.