21 Windsor Dr, Edgartown, MA 02539
Property image
Property image
OFF MARKET

21 Windsor Dr
Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,468 sqft (on 0.51 acres)

$1,278,500

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $7,174/mo*

$1,278,500

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $7,174/mo*
3 Beds
2 Baths
1,468 sqft
(on 0.51 acres)

Local Information

  • Map ViewExplore the area around 21 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
0.51 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

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 7

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.51 acres

Price History for 21 Windsor Dr

DatePriceEventSource
10/14/2020$785,000Sold
LINK #36157
08/12/2020$785,000PendingAgent Provided
06/05/2020$785,000PriceChange
Agent Provided
04/11/2020$769,000PriceChange
Agent Provided
01/13/2020$795,000PriceChange
Agent Provided
12/02/2019$825,000Listed For SaleN/A
04/07/2017$679,000Sold
LINK #31508
01/30/2017$679,000PendingAgent Provided
01/25/2017$679,000Listed For SaleAgent Provided
05/14/2004$517,500Sold
LINK #9780

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$3,101
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

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Assigned Schools

These are the assigned schools for 21 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 21 Windsor Dr

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Off Market Homes Near 21 Windsor Dr

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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).