55 Windsor Dr
Edgartown, MA 02539
3 bd 2 ba 1,568 sqft Built 1985 Lot 21,780 sqft single_family
Most recent sale
$1,009,000
Jul 20, 2022
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Jul 20, 2022 | Sold | $1,009,000 | MLS #32100563 |
| Dec 13, 2021 | Listed | $799,000 | MLS #39079 |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $937,500 | $333,800 | $1,271,300 | $3,369 |
| 2024 | $943,700 | $333,800 | $1,277,500 | $3,258 |
| 2023 | $747,300 | $302,800 | $1,050,100 | $2,646 |
| 2022 | $483,900 | $302,800 | $786,700 | $2,384 |
| 2020 | $384,500 | $275,300 | $659,800 | $2,210 |
| 2019 | $384,500 | $275,300 | $659,800 | $2,553 |
| 2018 | $358,400 | $275,300 | $633,700 | $2,452 |
| 2017 | $307,000 | $275,300 | $582,300 | $2,067 |
| 2016 | $281,300 | $275,200 | $556,500 | $2,015 |
| 2015 | $242,800 | $275,200 | $518,000 | $1,797 |
| 2014 | $243,800 | $283,300 | $527,100 | $1,950 |
| 2006 | $392,200 | $274,700 | $666,900 | $2,021 |
| 2005 | $341,700 | $217,900 | $559,600 | $1,707 |
| 2004 | $307,100 | $177,300 | $484,400 | $1,700 |
| 2003 | $260,400 | $148,600 | $409,000 | $1,505 |
Property facts
Year built
1985
Property type
single_family
Stories
1
Beds
3
Baths
2
Living area
1,568 sqft
Lot size
21,780 sqft
ZIP code
02539
City
Edgartown
Street
Windsor Dr
Coordinates
41.40361, -70.57300
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsInvestment analysis
Estimates based on local averages — not personalized adviceEstimated monthly rent
$4,547
Gross rental yield
5.41%
Implied cap rate
3.52%
Trend-extrapolated value
—
Frequently asked questions
When did 55 Windsor Dr last sell?
55 Windsor Dr most recently sold on Jul 20, 2022 for $1,009,000.
What is the current tax assessment for 55 Windsor Dr?
The most recent total assessment for 55 Windsor Dr (year 2025) is $1,271,300 with $3,369 in property tax.
How does 55 Windsor Dr's assessment compare to its last sale price?
The current assessment is 26.0% above the last sale price of $1,009,000.
When was 55 Windsor Dr built?
55 Windsor Dr was built in 1985.
How does 55 Windsor Dr compare to others on Windsor Dr?
We track 8 other properties on Windsor Dr. Browse the list under "Other properties on Windsor Dr" to compare beds, baths, and sale history.
What are the property facts for 55 Windsor Dr?
55 Windsor Dr is a 3 bed, 2 bath, 1,568 sqft, 21,780 sqft lot single_family.
Is 55 Windsor Dr a flip candidate?
No — 55 Windsor Dr does not appear in our flips dataset.
Is 55 Windsor Dr a tax-appeal candidate?
No — 55 Windsor Dr is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
+9.8%
Implied 1-yr
+39.2%
2026 Q2
$5.96M
2026 Q3
$6.21M
ZIP 02539 — Median Price History + Forecast
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Geography
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