55 Windsor Dr
Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 1,568 sqft (on 0.50 acres)
3 Beds
2 Baths
1,568 sqft
(on 0.50 acres)
Local Information
-- mins to
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
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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 |
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Exterior Home Features Exterior: PubBch |
Parking & Garage No CarportNo GarageNo Attached GarageParking: Yes |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Year Built Year Built: 1985 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
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Price List Price: $1,100,000 |
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MLS Status: S |
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Direction & Address City: Edgartown |
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Building Area Building Area: 1568 Square Feet |
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Lot Area: 0.50 acres |
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Listing Agreement Type: E |
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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
| Date | Price | Event | Source |
|---|---|---|---|
| 07/31/2023 | $1,100,000 | Sold | LINK #41153 |
| 07/20/2022 | $1,009,000 | Sold | LINK #39079 |
| 12/20/2021 | $799,000 | Pending | LINK #39079 |
| 12/13/2021 | $799,000 | Listed For Sale | LINK #39079 |
Market trends in Edgartown
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
1MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 55 Windsor Dr.
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.
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Off Market Homes Near 55 Windsor Dr
© 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.