18 Windsor Dr
Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 1,294 sqft (on 0.64 acres)
$1,150,000
Last Sold: May 8, 2026
15% over list $999K
$889/sqft
Est. Refi. Payment $6,454/mo*
$1,150,000
Last Sold: May 8, 2026
15% over list $999K
$889/sqft
Est. Refi. Payment $6,454/mo*
3 Beds
2 Baths
1,294 sqft
(on 0.64 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1981
Lot Size
0.64 acres
Living Area
1,294 sqft
Price/Sqft
$889/sqft
HOA
$15/Monthly
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). It is currently off market. The Trulia Estimate is $987,900, with a rent estimate of $4,778/month.
Home Details for 18 Windsor Dr
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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 |
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Exterior Home Features Exterior: DeckFoundation: Crawl space |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Year Built Year Built: 1981Year Renovated: 2022 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Property Information Parcel Number: 46 |
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Price List Price: $999,000Price Per Sqft: $889/sqft |
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MLS Status: S |
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Direction & Address City: Edgartown |
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Building Area Building Area: 1294 Square Feet |
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HOA Fee Includes: Road maintenanceHas an HOAHOA Fee: $175/Annually |
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Lot Area: 0.64 acres |
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Listing Agreement Type: E |
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BasementMls Number: 44102 |
Last check for updates: 24 minutes ago
Listed by Stephanie Roache
Donnelly + Co
Bought with: Paul Thoutsis, Dockside Real Estate
Source: LINK, MLS#44102
Price History for 18 Windsor Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 05/08/2026 | $1,150,000 | Sold | LINK #44102 |
| 04/15/2026 | $999,000 | Pending | LINK #44102 |
| 03/25/2026 | $999,000 | Contingent | MLS PIN #73489567 |
| 03/20/2026 | $999,000 | Listed For Sale | LINK #44102 |
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 | $2,533 |
| Assessment | $955,700 |
Home facts updated by county records
Comparable Sales for 18 Windsor Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | 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 | |
0.23 | Single-Family Home | $1,350,000 | 11/20/25 | 3 | 2 | 1,965 | |
0.24 | Single-Family Home | $1,450,000 | 08/26/25 | 3 | 2 | 2,311 | |
0.18 | Single-Family Home | $995,000 | 11/06/25 | 3 | 1 | 990 | |
0.31 | Single-Family Home | $1,260,000 | 11/03/25 | 4 | 2 | 1,820 | |
0.39 | Single-Family Home | $1,575,000 | 11/24/25 | 4 | 2 | 1,666 | |
0.81 | Single-Family Home | $1,175,000 | 04/22/26 | 3 | 2 | 1,196 | |
0.22 | Single-Family Home | $1,817,500 | 02/27/26 | 5 | 3 | 2,432 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 18 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 18 Windsor Dr
Off Market Homes Near 18 Windsor Dr
© 2026 LINK, All Rights Reserved. Data last updated: 2026-08-02 21:42:30 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.

