69 Windsor Dr
Edgartown, MA 02539
- 2 Beds
- 2 Baths
- 1,365 sqft (on 0.54 acres)
2 Beds
2 Baths
1,365 sqft
(on 0.54 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1986
Lot Size
0.54 acres
Living Area
1,365 sqft
Price/Sqft
$980
About this House
This single-family home is located at 69 Windsor Dr, Edgartown, MA. 69 Windsor Dr is in Edgartown, MA and in ZIP code 02539. This property has 2 bedrooms, 2 bathrooms and approximately 1,365 sqft of floor space. This property has a lot size of 0.50 acres and was built in 1986.
69 Windsor Dr, Edgartown, MA 02539 is a 2 bedroom, 2 bathroom, 1,365 sqft single-family home built in 1986. It last sold for $1,160,000 on Oct 3, 2022. It is currently off market. The Trulia Estimate is $1,337,400, with a rent estimate of $4,262/month.
Home Details for 69 Windsor Dr
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Heating & Cooling Heating: Other, OilHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 5 |
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Exterior Home Features Roof: AsphaltExterior: Wood |
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Year Built Year Built: 1986 |
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod |
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Units in Building: 1 |
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Lot Area: 0.54 acres |
Price History for 69 Windsor Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 10/03/2022 | $1,160,000 | Sold | LINK #39678 |
| 08/15/2022 | $1,250,000 | Pending | LINK #39678 |
| 07/21/2022 | $1,250,000 | PriceChange | LINK #39678 |
| 07/18/2022 | $1,295,000 | PriceChange | LINK #39678 |
| 06/10/2022 | $1,300,000 | Listed For Sale | LINK #39678 |
Market trends in Edgartown
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
64
1MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $2,971 |
| Assessment | $1,121,200 |
Home facts updated by county records
Comparable Sales for 69 Windsor Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $1,125,000 | 05/07/26 | 3 | 2 | 1,410 | |
0.09 | Single-Family Home | $1,575,000 | 11/24/25 | 4 | 2 | 1,666 | |
0.24 | Single-Family Home | $1,450,000 | 08/26/25 | 3 | 2 | 2,311 | |
0.47 | Single-Family Home | $1,150,000 | 05/08/26 | 3 | 2 | 1,294 | |
0.50 | Single-Family Home | $1,320,000 | 08/29/25 | 3 | 2 | 1,450 | |
0.17 | Single-Family Home | $1,890,000 | 08/29/25 | 4 | 3 | 3,270 | |
0.77 | Single-Family Home | $965,000 | 09/04/25 | 3 | 2 | 1,512 | |
0.84 | Single-Family Home | $1,135,000 | 10/31/25 | 3 | 2 | 1,344 | |
0.73 | Single-Family Home | $1,260,000 | 11/03/25 | 4 | 2 | 1,820 | |
0.48 | Single-Family Home | $1,550,000 | 04/09/26 | 4 | 2.5 | 2,291 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 69 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.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 69 Windsor Dr
Off Market Homes Near 69 Windsor Dr
Frequently asked questions about 69 Windsor Dr
- What is 69 Windsor Dr estimated to be worth?Trulia's estimated value for 69 Windsor Dr in Edgartown, MA is $1,337,400.
- What is the price history for 69 Windsor Dr?69 Windsor Dr in Edgartown, MA last sold for $1,160,000 in October 2022.
- Is Edgartown a buyer's or seller's market?Edgartown is currently a seller'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 69 Windsor Dr?The lot at 69 Windsor Dr in Edgartown, MA is about 0.50 acres (21,780 sq ft).

