18 Windsor Dr, Edgartown, MA 02539
Property image
Property image
SOLD
MAY 8, 2026

$990,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,294 sqft (on 0.64 acres)

18 Windsor Dr, Edgartown, MA 02539

Est. Refi. Payment $5,756/mo*
Refinance Your Home
Currently Off Market - Sold May 8, 2026 for $1,150,000 (15% above list price)

Home Value

Trulia Estimate
$991K
Since last month
Increased$1K (+0.1%)
Since last year
Decreased$19K (-1.9%)
Since last sale
Decreased$159K (-13.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +88% in the last 10 years
MonthEstimated value
2026
September 2026$991K
August 2026$991K
July 2026$990K
June 2026$990K
May 2026$990K
April 2026$990K
March 2026$996K
February 2026$1.06M
January 2026$1.06M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
52 Windsor Dr, Edgartown, MA
0.31
Single-Family Home
$1,125,000
05/07/26
3
2
1,410
16 Majors Cove Ln, Edgartown, MA
0.23
Single-Family Home
$1,350,000
11/20/25
3
2
1,965
1 Dodgers Hole Road, Edgartown, MA
0.20
Single-Family Home
$1,050,000
09/11/26
4
2
1,513
2 Flamingo Dr, Edgartown, MA
0.18
Single-Family Home
$995,000
11/06/25
3
1
990
11 Flamingo Dr, Edgartown, MA
0.31
Single-Family Home
$1,260,000
11/03/25
4
2
1,820
60 Windsor Dr, Edgartown, MA
0.39
Single-Family Home
$1,575,000
11/24/25
4
2
1,666
112 3rd St N, Edgartown, MA
0.81
Single-Family Home
$1,175,000
04/22/26
3
2
1,196
32 Flamingo Dr, Edgartown, MA
0.22
Single-Family Home
$1,817,500
02/27/26
5
3
2,432
1 Edgewood Dr, Edgartown, MA
0.22
Single-Family Home
$1,280,000
12/12/25
3
2
1,604

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
10 Eagles Nest, Edgartown, MA 02539
0.07
$1,356,000
3
2
1,450
Off Market
37 Dodgers Hole Rd, Edgartown, MA 02539
0.07
$1,225,000
3
2
1,338
For Sale
12 Eagles Nest, Edgartown, MA 02539
0.07
$1,409,200
4
2
1,404
Off Market
41 Dodgers Hole Rd, Edgartown, MA 02539
0.07
$1,591,400
3
2
1,326
Off Market
31 Dodgers Hole Rd, Edgartown, MA 02539
0.08
$1,625,000
3
2.5
1,960
For Sale
39 Flamingo Dr, Edgartown, MA 02539
0.14
$1,306,000
3
2
1,420
Off Market
2 Flamingo Dr, Edgartown, MA 02539
0.18
$1,022,200
3
1
990
Off Market
1 Dodgers Hole Road, Edgartown, MA 02539
0.20
$1,050,000
4
2
1,513
Recently Sold
16 Majors Cove Ln, Edgartown, MA 02539
0.24
$1,350,000
3
2
1,965
Recently Sold
4 Mockingbird Dr, Edgartown, MA 02539
0.23
$1,174,000
3
1.5
1,200
Off Market
1 Edgewood Dr, Edgartown, MA 02539
0.22
$1,280,000
3
2
1,604
Recently Sold

Local Information

  • Map ViewExplore the area around 18 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1981
0.64 acre lot
1,294 sqft
$889/sqft
HOA $15/mo

About this House

Welcome to this light-filled Vineyard Cape brimming with potential, offering an open layout and abundant natural light. Vaulted ceilings enhance the spacious living and dining area, creating an airy setting for relaxing or entertaining. The kitchen has direct access to the outdoor deck, ideal for summer gatherings and al fresco dining. Two bedrooms and a full bathroom with laundry complete the first floor. Upstairs, you’ll find a generous primary bedroom with abundant closet space, an additional full bathroom, and a cozy loft-style den overlooking the main living area. Centrally located just moments from the bike path, with easy access to Edgartown, nearby beaches, and all down-Island amenities, this property presents a wonderful opportunity to make it your own. With a 4-bedroom septic in place, there is potential for expansion. The property is being sold “AS IS”.
18 Windsor Dr, Edgartown, MA 02539 is a 3 bedroom, 2 bathroom, 1,294 sqft single-family home built in 1981. It last sold for $1,150,000 on May 8, 2026 (15% above the $999,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $990,800, with a rent estimate of $4,583/month.
Last check for updates: about 19 hours ago
Listed by Stephanie Roache
Donnelly + Co
Bought with: Paul Thoutsis, Dockside Real Estate
Source: LINK, MLS#44102

Home Details for 18 Windsor Dr

Interior Features

Interior Details
Basement: Crawl spaceNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1294 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: GE, Washer: Yes
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: None
Windows, Doors, Floors & Walls
Flooring: Laminate, carpeting
Levels, Entrance, & Accessibility
Floors: Laminate, Carpeting
View
Has a ViewView: None, Res

Exterior Features

Exterior Home Features
Exterior: DeckFoundation: Crawl space
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1981Year Renovated: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 46

Price & Status

Price
List Price: $999,000Price Per Sqft: $889/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Edgartown

Building

Building Area
Building Area: 1294 Square Feet

HOA

HOA Fee Includes: Road maintenanceHas an HOAHOA Fee: $175/Annually

Lot Information

Lot Area: 0.64 acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 44102

Price and Tax history

DateEventPrice
May 8, 2026
Source: LINK #44102
Sold
$1,150,000
Apr 15, 2026
Source: LINK #44102
Pending
$999,000
Mar 25, 2026
Source: MLS PIN #73489567
Contingent
$999,000
Mar 20, 2026
Source: LINK #44102
Listed For Sale
$999,000

Market trends in Edgartown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
68
1MoM

Around this home

View nearby schools on GreatSchools
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 "
    0
    Flag
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
    2
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
    0
    Flag
  • 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 "
    0
    Flag
  • 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 "
    5
    Flag
  • 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"
    4
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-16 03:28:24 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.

Frequently asked questions about 18 Windsor Dr

  • What is 18 Windsor Dr estimated to be worth?
    Trulia's estimated value for 18 Windsor Dr in Edgartown, MA is $990,800.
  • What is the price history for 18 Windsor Dr?
    18 Windsor Dr in Edgartown, MA last sold for $1,150,000 in May 2026.
  • Is Edgartown a buyer's or seller's market?
    Edgartown is currently a buyer'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.
  • How big is the lot at 18 Windsor Dr?
    The lot at 18 Windsor Dr in Edgartown, MA is about 0.64 acres (27,878 sq ft).

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 18 Windsor Dr

Skip to last item
Skip to first item

Homes for sale near 18 Windsor Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item