21 Windsor Dr
Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 1,468 sqft (on 0.51 acres)
3 Beds
2 Baths
1,468 sqft
(on 0.51 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1985
Lot Size
0.51 acres
Living Area
1,468 sqft
Price/Sqft
$871
About this House
Classic Cape-Style Three Bedroom Home located in Westminster Acres neighborhood in Edgartown. Walk through this classic cape into an open floor plan that features a living room with fireplace, dining area and kitchen. The kitchen has an abundance of cabinets. A room and a full bath finish the first level. The second floor has a full dormer off of the back which makes the bedrooms generous in size. The second floor features three bedrooms and one full bath. Enjoy the spacious deck and sitting area that overlook the private backyard. Full basement. A paved road allows for easy access to the bike path. Air conditioning. Three bedroom septic in place. This lot will support a four bedroom system per Board of Health.
21 Windsor Dr, Edgartown, MA 02539 is a 3 bedroom, 2 bathroom, 1,468 sqft single-family home built in 1985. It last sold for $785,000 on Oct 14, 2020. It is currently off market. The Trulia Estimate is $1,278,500, with a rent estimate of $4,733/month.
Home Details for 21 Windsor Dr
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Heating & Cooling Heating: Baseboard, ElectricAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Hardwood |
Interior Details Number of Rooms: 7 |
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Exterior Home Features Roof: AsphaltExterior: Wood |
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Year Built Year Built: 1985 |
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod |
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Units in Building: 1 |
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Lot Area: 0.51 acres |
Price History for 21 Windsor Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 10/14/2020 | $785,000 | Sold | LINK #36157 |
| 08/12/2020 | $785,000 | Pending | Agent Provided |
| 06/05/2020 | $785,000 | PriceChange | Agent Provided |
| 04/11/2020 | $769,000 | PriceChange | Agent Provided |
| 01/13/2020 | $795,000 | PriceChange | Agent Provided |
| 12/02/2019 | $825,000 | Listed For Sale | N/A |
| 04/07/2017 | $679,000 | Sold | LINK #31508 |
| 01/30/2017 | $679,000 | Pending | Agent Provided |
| 01/25/2017 | $679,000 | Listed For Sale | Agent Provided |
| 05/14/2004 | $517,500 | Sold | LINK #9780 |
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 | $3,101 |
| Assessment | $1,170,000 |
Home facts updated by county records
Comparable Sales for 21 Windsor Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $1,150,000 | 05/08/26 | 3 | 2 | 1,294 | |
0.14 | Single-Family Home | $1,320,000 | 08/29/25 | 3 | 2 | 1,450 | |
0.31 | Single-Family Home | $1,125,000 | 05/07/26 | 3 | 2 | 1,410 | |
0.24 | Single-Family Home | $1,450,000 | 08/26/25 | 3 | 2 | 2,311 | |
0.25 | Single-Family Home | $1,350,000 | 11/20/25 | 3 | 2 | 1,965 | |
0.24 | Single-Family Home | $995,000 | 11/06/25 | 3 | 1 | 990 | |
0.37 | Single-Family Home | $1,260,000 | 11/03/25 | 4 | 2 | 1,820 | |
0.38 | Single-Family Home | $1,575,000 | 11/24/25 | 4 | 2 | 1,666 | |
0.16 | Single-Family Home | $1,280,000 | 12/12/25 | 3 | 2 | 1,604 | |
0.74 | Single-Family Home | $1,175,000 | 04/22/26 | 3 | 2 | 1,196 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 21 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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Apartments for Rent
Homes for sale near 21 Windsor Dr
Off Market Homes Near 21 Windsor Dr
Frequently asked questions about 21 Windsor Dr
- What is 21 Windsor Dr estimated to be worth?Trulia's estimated value for 21 Windsor Dr in Edgartown, MA is $1,278,500.
- What is the price history for 21 Windsor Dr?21 Windsor Dr in Edgartown, MA last sold for $785,000 in October 2020.
- Is Edgartown a buyer's or seller's market?Edgartown is currently a seller'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 21 Windsor Dr have air conditioning?Yes, 21 Windsor Dr in Edgartown, MA has air conditioning.
- How big is the lot at 21 Windsor Dr?The lot at 21 Windsor Dr in Edgartown, MA is about 0.51 acres (22,215 sq ft).

