55 Windsor Dr, Edgartown, MA 02539
OFF MARKET

55 Windsor Dr
Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,568 sqft (on 0.50 acres)

$1,422,400

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $7,950/mo*

$1,422,400

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $7,950/mo*
3 Beds
2 Baths
1,568 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 55 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Lot Size
0.5 acres
Living Area
1,568 sqft
Price/Sqft
$907
HOA
None

About this House

Not listed in LINK.
55 Windsor Dr, Edgartown, MA 02539 is a 3 bedroom, 2 bathroom, 1,568 sqft single-family home built in 1985. It last sold for the $1,100,000 asking price on Jul 31, 2023. It is currently off market. The Trulia Estimate is $1,422,400, with a rent estimate of $4,975/month.

Home Details for 55 Windsor Dr

Interior Features

Interior Details
Basement: FullNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1568 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: OFHWNo CoolingHas HeatingHeating Fuel: OFHW
Fireplace & Spa
Fireplace: Yes
View
Has a ViewView: None, Res

Exterior Features

Exterior Home Features
Exterior: PubBch
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: $1,100,000

Active Status

MLS Status: S

Location

Direction & Address
City: Edgartown

Building

Building Area
Building Area: 1568 Square Feet

Lot Information

Lot Area: 0.50 acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 41153
Last check for updates: about 4 hours ago
Listed by LINK
LINK
Source: LINK, MLS#41153

Price History for 55 Windsor Dr

DatePriceEventSource
07/31/2023$1,100,000Sold
LINK #41153
07/20/2022$1,009,000Sold
LINK #39079
12/20/2021$799,000PendingLINK #39079
12/13/2021$799,000Listed For SaleLINK #39079

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$3,369
Assessment$1,271,300
Home facts updated by county records

Comparable Sales for 55 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.05
Single-Family Home
$1,125,000
05/07/26
3
2
1,410
0.05
Single-Family Home
$1,575,000
11/24/25
4
2
1,666
0.13
Single-Family Home
$1,450,000
08/26/25
3
2
2,311
0.38
Single-Family Home
$1,320,000
08/29/25
3
2
1,450
0.35
Single-Family Home
$1,150,000
05/08/26
3
2
1,294
0.06
Single-Family Home
$1,890,000
08/29/25
4
3
3,270
0.62
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
0.59
Single-Family Home
$1,350,000
11/20/25
3
2
1,965
0.83
Single-Family Home
$965,000
09/04/25
3
2
1,512
0.51
Single-Family Home
$995,000
11/06/25
3
1
990

Nearby homes

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Assigned Schools

These are the assigned schools for 55 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 55 Windsor Dr

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Off Market Homes Near 55 Windsor Dr

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-08-02 01:11:47 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.