20 Winchester St
Brookline, MA 02446
3 bd 2 ba 1,296 sqft Built 1895 condos
Most recent sale
$995,000
Apr 21, 2022
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Apr 23, 2026 | Sold | $1,029,000 | MLSPIN |
| Mar 3, 2026 | Listed | $1,029,000 | MLSPIN |
| Oct 1, 2025 | Listing removed | $1,095,000 | MLSPIN |
| Aug 13, 2022 | Listing removed | $925,000 | MLSPIN |
| Apr 21, 2022 | Sold | $995,000 | MLS #72952815 |
| Mar 28, 2022 | Relisted | $859,000 | MLS #72952815 |
| Mar 15, 2022 | Listed | $859,000 | MLS #72952815 |
| Feb 13, 2021 | Listing removed | $992,000 | MLSPIN |
| Jul 15, 2016 | Sold | $805,000 | MLS #72002164 |
| May 10, 2016 | Listed | $715,000 | MLS #72002164 |
| Aug 29, 2013 | Sold | $575,000 | MLS #71462631 |
| Dec 5, 2012 | Listed | $559,000 | MLS #71462631 |
| Sep 3, 2004 | Sold | $490,000 | Public Record |
| Jun 18, 2001 | Sold | $365,000 | Public Record |
| Sep 3, 1998 | Sold | $230,000 | Public Record |
| Sep 15, 1992 | Sold | $148,000 | Public Record |
| Jul 24, 1987 | Sold | $165,000 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $884,500 | — | $884,500 | $8,730 |
| 2024 | $867,200 | — | $867,200 | $8,473 |
| 2023 | $839,900 | — | $839,900 | $8,374 |
| 2022 | $823,500 | — | $823,500 | $8,391 |
| 2021 | $815,400 | — | $815,400 | $7,991 |
| 2020 | $807,300 | — | $807,300 | $7,629 |
| 2019 | $768,900 | — | $768,900 | $7,205 |
| 2018 | $700,600 | — | $700,600 | $6,628 |
| 2017 | $648,700 | — | $648,700 | $6,409 |
| 2016 | $589,800 | — | $589,800 | $6,146 |
| 2015 | $536,100 | — | $536,100 | $5,726 |
| 2014 | $486,100 | — | $486,100 | $5,537 |
| 2006 | — | — | $446,300 | $4,262 |
| 2005 | — | — | $413,200 | $4,227 |
| 2004 | — | — | $372,900 | $3,964 |
| 2003 | — | — | $348,500 | $3,907 |
Property facts
Year built
1895
Property type
condos
Stories
1
Beds
3
Baths
2
Living area
1,296 sqft
Lot size
—
ZIP code
02446
City
Brookline
Street
Winchester St
Coordinates
42.34181, -71.12540
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
$3,758
Gross rental yield
4.53%
Implied cap rate
2.95%
Trend-extrapolated value
—
Frequently asked questions
When did 20 Winchester St last sell?
20 Winchester St most recently sold on Apr 21, 2022 for $995,000.
What is the current tax assessment for 20 Winchester St?
The most recent total assessment for 20 Winchester St (year 2025) is $884,500 with $8,730 in property tax.
How does 20 Winchester St's assessment compare to its last sale price?
The current assessment is 11.1% below the last sale price of $995,000.
When was 20 Winchester St built?
20 Winchester St was built in 1895.
How does 20 Winchester St compare to others on Winchester St?
We track 8 other properties on Winchester St. Browse the list under "Other properties on Winchester St" to compare beds, baths, and sale history.
What are the property facts for 20 Winchester St?
20 Winchester St is a 3 bed, 2 bath, 1,296 sqft condos.
Is 20 Winchester St a flip candidate?
No — 20 Winchester St does not appear in our flips dataset.
Is 20 Winchester St a tax-appeal candidate?
No — 20 Winchester St is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
-3.6%
Implied 1-yr
-14.3%
2026 Q3
$1.05M
2026 Q4
$1M
ZIP 02446 — Median Price History + Forecast
Explore nearby
Geography
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