Date
Details
Price
Change
Source
3/20/2026
Listed
$999,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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 flows seamlessly to an 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 room for expansion. The property is being sold "AS IS".
Full Property Details
Full Property Details for 18 Windsor Dr
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General
- Price: $999,000
- Taxes: $2,782 (2026)
- Status: Active
- Type: Single Family
- MLS ID: 73489567
- Updated: 3/20/2026
- Added to Site: 2 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Bathroom 1: Second
- Bathroom 2: First
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Second
- Bedroom 2: Main, First
- Bedroom 3: Main, First
Other Rooms
- Living Room: Main, First
- Kitchen: Main, First
- Dining Room: Main, First
Parking
- Parking Features: Unpaved
Location
- County: Dukes
Structural Information
- Architectural Style: Cape
- Square Feet: 1,294
- Year Built: 1981
Lot Features
- Lot Size (Acres): 0.64
Financial Considerations
- Tax Amount: $2,782
- Tax Year: 2026
Disclosures and Reports
- Disclosures/Rstr.: The property is being sold “AS ISâ€.
- Property ID: 3768339
- Block/Lot/Section: 99
Listed by Donnelly + Co., Stephanie Roache
We Value Your Privacy
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Listing agent
— 18 Windsor Dr —
Stephanie Roache
Donnelly + Co.
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 18 Windsor Dr
School Districts:Martha's Vineyard School District, Edgartown School District
| Name | Grades | Distance |
|---|---|---|
Edgartown Elementary School 35 Robinson Road, Edgartown, MA 02539 | PK-8 | 3 mi |
Marthas Vineyard Regional High School 100 Edgartown-Vineyard Haven R, Oak Bluffs, MA 02557 | 9-12 | 1.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 18 Windsor Dr
Tax History
Tax History for 18 Windsor Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,533
14%
$955,700
9%
2024
$2,230
9%
$874,500
8%
2023
$2,044
7%
$811,200
29%
2022
$1,911
-4%
$630,800
4%
2021
$1,995
6%
$608,300
8%
2020
$1,888
-13%
$563,700
—
2019
$2,182
17%
$563,700
17%
2018
$1,860
9%
$480,500
—
2017
$1,706
4%
$480,500
6%
2016
$1,638
3%
$452,400
-1%
2015
$1,593
-6%
$459,100
—
2014
$1,695
—
$458,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 18 Windsor Dr
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- Single Family
- Active
- Updated 7 days ago
- 2Beds
- 2Total Baths
- 1,583Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,236Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 1Sq. Ft.
- Single Family
- Active
- Updated 16 hours ago
- 4Beds
- 6Total Baths
- 4,802Sq. Ft.
Listed by The Quirk Group (617) 266-4430
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 3Total Baths
- 1,954Sq. Ft.
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- Single Family
- Active
- Updated 5 days ago
- 5Beds
- 6Total Baths
- 5,598Sq. Ft.
- Duplex
- Active
- Updated 6 days ago
- 3Beds
- 3Total Baths
- 2,440Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 3Total Baths
- 2,064Sq. Ft.
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18 Windsor Drive, Edgartown, MA 02539 (MLS# 73489567) is a Single Family property with 3 bedrooms and 2 full bathrooms. 18 Windsor Drive is currently listed for $999,000 and was received on March 20, 2026. Want to learn more about 18 Windsor Drive? Do you have questions about finding other Single Family real estate for sale in Edgartown? You can browse all Edgartown real estate or contact a Coldwell Banker agent to request more information.