2 Windsor Dr
Edgartown, MA 02539
- 4 Beds
- 2 Baths
- 1,828 sqft (on 0.55 acres)
4 Beds
2 Baths
1,828 sqft
(on 0.55 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1986
Lot Size
0.55 acres
Living Area
1,828 sqft
Price/Sqft
$705
About this House
Attractive four bedroom Colonial in Westminster Acres. This lovely house has been recently updated with new kitchen cabinets, appliances and granite counter tops. The first floor features an open kitchen/dining area, living room, a home office/den as well as a large, bright three season room. There are four large bedrooms on the second floor with a full bath. A third floor room could easily be finished for additional living space. The large deck wraps around the side of the house to the back, where there is a nice private yard. Just some of the improvements in 2013 include a new roof, new shingles, interior paint throughout and a new front porch. Excellent location, close to all down Island towns.
Neighborhood Description
Beautiful family orientated neighborhood.
Neighborhood Description
Beautiful family orientated neighborhood.
2 Windsor Dr, Edgartown, MA 02539 is a 4 bedroom, 2 bathroom, 1,828 sqft single-family home built in 1986. It last sold for $554,000 on Jun 16, 2015. More recently, it was listed as a rental in July 2012 with an asking price of $2,000 per month. That rental listing was removed on September 3, 2012. It is currently off market. The Trulia Estimate is $1,289,300, with a rent estimate of $5,296/month.
Home Details for 2 Windsor Dr
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Interior Details BasementAtticNumber of Rooms: 9Types of Rooms: Breakfast Nook, Family Room, Sun Room |
Heating & Cooling Heating: Baseboard, ElectricHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood |
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
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Exterior Home Features Roof: AsphaltDeckExterior: WoodGardenLawnPorch |
Parking & Garage Parking: Off Street |
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Year Built Year Built: 1986Year Updated: 2013 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Furnished |
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Units in Building: 1 |
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Lot Area: 0.55 acres |
Price History for 2 Windsor Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 06/16/2015 | $554,000 | Sold | LINK #26273 |
| 11/16/2014 | $599,000 | ListingRemoved | Agent Provided |
| 05/23/2014 | $599,000 | Listed For Sale | Agent Provided |
| 09/03/2012 | $2,000 | ListingRemoved | N/A |
| 07/05/2012 | $2,000 | Listed For Rent | N/A |
| 03/31/2011 | $370,000 | Sold | LINK #21031 |
| 04/21/2010 | $408,000 | Sold | LINK #19682 |
| 12/30/2004 | $530,000 | Sold | LINK #9716 |
Market trends in Edgartown
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
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Available listings
64
1MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $2,570 |
| Assessment | $969,700 |
Home facts updated by county records
Comparable Sales for 2 Windsor Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.23 | Single-Family Home | $1,260,000 | 11/03/25 | 4 | 2 | 1,820 | |
0.07 | Single-Family Home | $1,350,000 | 11/20/25 | 3 | 2 | 1,965 | |
0.17 | Single-Family Home | $1,320,000 | 08/29/25 | 3 | 2 | 1,450 | |
0.17 | Single-Family Home | $1,150,000 | 05/08/26 | 3 | 2 | 1,294 | |
0.13 | Single-Family Home | $995,000 | 11/06/25 | 3 | 1 | 990 | |
0.41 | Single-Family Home | $1,450,000 | 08/26/25 | 3 | 2 | 2,311 | |
0.49 | Single-Family Home | $1,125,000 | 05/07/26 | 3 | 2 | 1,410 | |
0.56 | Single-Family Home | $1,575,000 | 11/24/25 | 4 | 2 | 1,666 | |
0.19 | Single-Family Home | $1,817,500 | 02/27/26 | 5 | 3 | 2,432 | |
0.23 | Single-Family Home | $2,495,000 | 11/20/25 | 4 | 5 | 2,694 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 2 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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