52 Windsor Dr, Edgartown, MA 02539
SOLD
MAY 7, 2026

52 Windsor Dr
Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,410 sqft (on 0.50 acres)

$1,125,000

Last Sold: May 7, 2026
6% below list $1.2M
$798/sqft
Est. Refi. Payment $6,132/mo*

$1,125,000

Last Sold: May 7, 2026
6% below list $1.2M
$798/sqft
Est. Refi. Payment $6,132/mo*
3 Beds
2 Baths
1,410 sqft
(on 0.50 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The full basement offers generous storage and in-home laundry. BOH says four bedrooms are possible if septic is upgraded. Current three bedroom septic passed Title V. Easy access to multiple towns and Island beaches, this home puts the best of Martha's Vineyard at your doorstep.
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. This description is from May 13, 2026

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
$15/Monthly
Price/Sqft
$798/sqft
Listed
58 days ago

Home Details for 52 Windsor Dr

Interior Features

Interior Details
Basement: Full BasementNumber of Rooms: 5
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 1Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1410 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: 0
Windows, Doors, Floors & Walls
Flooring: 2
Levels, Entrance, & Accessibility
Floors: 2
View
No ViewView: None
Room & Shared Space
Shared space is furnished

Exterior Features

Exterior Home Features
Exterior: PubBchFoundation: Full Basement
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Yes
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $1,195,000Price Per Sqft: $798/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Edgartown

Building

Building Area
Building Area: 1410 Square Feet

HOA

Has an HOAHOA Fee: $175/Annually

Lot Information

Lot Area: 0.50 acres

Offer

Listing Agreement Type: E

Rental Terms, Policies & Fees

Furnished

Miscellaneous

BasementMls Number: 44183
Last check for updates: about 9 hours ago
Listed by Emma Kennedy
Sandpiper Realty
Bought with: Compass | The O'Hanlon Group
Source: LINK, MLS#44183

Price History for 52 Windsor Dr

DatePriceEventSource
05/07/2026$1,125,000Sold
LINK #44183
04/11/2026$1,195,000PendingLINK #44183
03/20/2026$1,195,000Listed For SaleMLS PIN #73489622
12/28/2005$565,000Sold
LINK #10809
09/27/2002$260,455Sold
N/A

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$2,311
Assessment$872,200
Home facts updated by county records

Homeowner tools

Estimated monthly rent$6,223/mo

Homes for rent near 52 Windsor Dr

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Comparable Sales for 52 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Single-Family Home
$1,450,000
08/26/25
3
2
2,311
0.08
Single-Family Home
$1,575,000
11/24/25
4
2
1,666
0.03
Single-Family Home
$1,400,000
07/10/25
3
2.5
2,019
0.34
Single-Family Home
$1,320,000
08/29/25
3
2
1,450
0.31
Single-Family Home
$1,150,000
05/08/26
3
2
1,294
0.31
Single-Family Home
$1,299,000
06/25/25
3
2
1,512
0.05
Single-Family Home
$1,890,000
08/29/25
4
3
3,270
0.57
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
0.55
Single-Family Home
$1,350,000
11/20/25
3
2
1,965

Nearby homes

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Assigned Schools

These are the assigned schools for 52 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 52 Windsor Dr

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Off Market Homes Near 52 Windsor Dr

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-06-19 00:42:40 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.
52 Windsor Dr, Edgartown, MA 02539 is a 3 bedroom, 2 bathroom, 1,410 sqft single-family home built in 1985. This property is not currently available for sale. 52 Windsor Dr was last sold on May 7, 2026 for $1,125,000 (6% lower than the asking price of $1,195,000). The current Trulia Estimate for 52 Windsor Dr is $1,125,200.