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”.
Sold for $1,150,000
$1,150,000
18 Windsor Dr, Edgartown, MA 02539
3beds
1,294sqft
Single Family Residence
Built in 1981
0.64 Acres Lot
$990,800 Zestimate®
$889/sqft
$4,583 Estimated rent
Home value
$990,800
$941,000 - $1.04M
$4,583/mo
Zestimate® history
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List your homeWhat's special
Open layoutLight-filled vineyard capeAbundant natural lightVaulted ceilings
Zillow last checked:
Listing updated:
Listed by:
Stephanie Roache,
Donnelly + Co
Bought with:
Paul Thoutsis
Dockside Real Estate
Source: LINK,MLS#: 44102
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
- Main level bedrooms: 2
Heating
- Electric
Appliances
- Included: Stove: GE, Washer: Yes
Features
- Floor 1: Enjoy the open-concept living and dining areas, which flow seamlessly into the kitchen. Two sets of sliding glass doors lead to a spacious deck, perfect for extended outdoor entertaining. Two bedrooms and a full bathroom with laundry complete the first floor., Floor 2: The second floor offers a spacious primary bedroom with an abundance of closet space, an open den, and a full bathroom.
- Flooring: Laminate, carpeting
- Basement: Crawl space
- Fireplace features: None
Interior area
- Total structure area: 1,294
- Total interior livable area: 1,294 sqft
Property
Features
- Exterior features: Deck
- Has view: Yes
- View description: None, Res
- Frontage type: None
Lot
- Size: 0.64 Acres
- Features: Yes
Details
- Parcel number: 46
- Zoning: R60
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Crawl space
Condition
- Year built: 1981
- Major remodel year: 2022
Utilities & green energy
- Sewer: Septic Tank
- Water: Town
- Utilities for property: Cbl
Community & HOA
HOA
- Has HOA: Yes
- Services included: Road maintenance
- HOA fee: $175 annually
Location
- Region: Edgartown
Financial & listing details
- Price per square foot: $889/sqft
- Tax assessed value: $1,121,900
- Annual tax amount: $2,782
- Date on market: 3/20/2026
- Listing agreement: E
Price history
| Date | Event | Price |
|---|---|---|
| 5/8/2026 | Sold | $1,150,000+15.1%$889/sqft |
Source: LINK #44102 Report a problem | ||
| 4/15/2026 | Pending sale | $999,000$772/sqft |
Source: LINK #44102 Report a problem | ||
| 3/25/2026 | Contingent | $999,000$772/sqft |
Source: MLS PIN #73489567 Report a problem | ||
| 3/20/2026 | Listed for sale | $999,000$772/sqft |
Source: LINK #44102 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,533 +13.6% | $955,700 +9.3% |
| 2024 | $2,230 +9.1% | $874,500 +7.8% |
| 2023 | $2,044 +7% | $811,200 +28.6% |
| 2022 | $1,911 -4.2% | $630,800 +3.7% |
| 2021 | $1,995 +5.7% | $608,300 +7.9% |
| 2020 | $1,888 -13.5% | $563,700 |
| 2019 | $2,182 +17.3% | $563,700 +17.3% |
| 2018 | $1,860 +9% | $480,500 |
| 2017 | $1,706 +4.2% | $480,500 +6.2% |
| 2016 | $1,638 +2.8% | $452,400 -1.5% |
| 2015 | $1,593 -6% | $459,100 +0.2% |
| 2014 | $1,695 +3.4% | $458,000 -0.8% |
| 2013 | $1,639 +3.5% | $461,800 |
| 2012 | $1,584 +3.4% | $461,800 +2.5% |
| 2011 | $1,532 +2.3% | $450,500 -7% |
| 2010 | $1,497 +5.6% | $484,600 -0.5% |
| 2009 | $1,417 -0.2% | $486,900 -6.4% |
| 2008 | $1,420 -4.6% | $520,100 -0.4% |
| 2007 | $1,488 +0.5% | $522,100 +6.9% |
| 2006 | $1,480 +18.4% | $488,300 +19.2% |
| 2005 | $1,250 +7.6% | $409,700 +23.8% |
| 2004 | $1,162 +9% | $331,000 +14.2% |
| 2003 | $1,066 -3.5% | $289,800 +34.8% |
| 2001 | $1,105 +4.4% | $215,000 +26.8% |
| 2000 | $1,058 | $169,500 |
Find assessor info on the county website
Neighborhood: 02539
Nearby homes
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Nearby schools
GreatSchools rating
- 7/10Edgartown Elementary SchoolGrades: PK-8Distance: 3 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 1.3 mi
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$990,800
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$1,010,616
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$990,800
2% more
+$19,816
With Zillow Showcase(estimated)
$1,010,616
- Massachusetts
- Dukes County
- Edgartown
- 02539
- 18 Windsor Dr
