2 Windsor Dr, Edgartown, MA 02539
OFF MARKET

2 Windsor Dr
Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,828 sqft (on 0.55 acres)

$1,321,300

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $7,134/mo*

$1,321,300

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $7,134/mo*
4 Beds
2 Baths
1,828 sqft
(on 0.55 acres)

Local Information

  • Map ViewExplore the area around 2 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2 Windsor Dr

Interior Features

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

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1986Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 0.55 acres

Price History for 2 Windsor Dr

DatePriceEventSource
06/16/2015$554,000Sold
LINK #26273
11/16/2014$599,000ListingRemovedAgent Provided
05/23/2014$599,000Listed For SaleAgent Provided
09/03/2012$2,000ListingRemovedN/A
07/05/2012$2,000Listed For RentN/A
03/31/2011$370,000Sold
LINK #21031
04/21/2010$408,000Sold
LINK #19682
12/30/2004$530,000Sold
LINK #9716

Market trends in Edgartown

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
63
14
MoM
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Property Tax and Assessment

Year2025
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
0.51
Single-Family Home
$1,400,000
07/10/25
3
2.5
2,019

Nearby homes

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Assigned Schools

These are the assigned schools for 2 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 2 Windsor Dr

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Off Market Homes Near 2 Windsor Dr

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2 Windsor Dr, Edgartown, MA 02539 is a 4 bedroom, 2 bathroom, 1,828 sqft single-family home built in 1986. This property is not currently available for sale. 2 Windsor Dr was last sold on Jun 16, 2015 for $554,000. The current Trulia Estimate for 2 Windsor Dr is $1,321,300.