66 Winchester St
Brookline, MA 02446
2 bd 2 ba 1,197 sqft Built 1983 condo
Most recent sale
$595,000
Aug 31, 2012
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Jun 1, 2025 | Listing removed | $4,400 | MLSPIN |
| Apr 22, 2025 | Sold | $1,100,000 | Public Record |
| Oct 10, 2022 | Listing removed | $1,100,000 | MLSPIN |
| Aug 13, 2022 | Listing removed | $1,100,000 | MLSPIN |
| Jul 12, 2022 | Listing removed | $3,975 | MLSPIN |
| Jun 25, 2022 | Listed for rent | $3,975 | MLSPIN |
| May 11, 2022 | Listed | $1,100,000 | MLS #72980018 |
| May 6, 2022 | Listed | $1,100,000 | MLS #72977762 |
| Apr 5, 2021 | Listing removed | $3,100 | MLSPIN |
| Oct 1, 2020 | Price changed for rent | $3,100 | AppfolioUnits |
| Sep 16, 2020 | Price changed for rent | $3,250 | AppfolioUnits |
| Aug 27, 2020 | Listed for rent | $3,450 | AppfolioUnits |
| Jul 16, 2020 | Listed for rent | $3,500 | AppfolioUnits |
| Jul 6, 2018 | Listing removed | $3,350 | MLSPIN |
| Jul 3, 2018 | Listing removed | $3,350 | AppfolioUnits |
| Jun 25, 2018 | Listed for rent | $3,350 | MLSPIN |
| Jun 22, 2018 | Price changed for rent | $3,350 | AppfolioUnits |
| Jun 11, 2018 | Listed for rent | $3,600 | AppfolioUnits |
| Jul 15, 2017 | Listing removed | $3,250 | MLSPIN |
| Jul 13, 2017 | Listing removed | $3,300 | AppfolioUnits |
| Jun 29, 2017 | Listed for rent | $3,300 | MLSPIN |
| Jun 16, 2017 | Listed for rent | $3,300 | AppfolioUnits |
| Dec 15, 2016 | Listing removed | $2,995 | AppfolioUnits |
| Sep 22, 2016 | Listing removed | $2,995 | MLSPIN |
| Sep 18, 2016 | Listing removed | $2,995 | MLSPIN |
| Aug 30, 2016 | Price changed for rent | $2,995 | AppfolioUnits |
| Aug 29, 2016 | Price changed for rent | $2,995 | MLSPIN |
| Aug 25, 2016 | Price changed for rent | $3,200 | MLSPIN |
| Aug 18, 2016 | Listed for rent | $3,300 | MLSPIN |
| Aug 17, 2016 | Price changed for rent | $3,200 | AppfolioUnits |
| Aug 11, 2016 | Listed for rent | $3,300 | MLSPIN |
| Aug 4, 2016 | Price changed for rent | $3,300 | AppfolioUnits |
| Jul 21, 2016 | Listed for rent | $3,500 | AppfolioUnits |
| Aug 31, 2012 | Sold | $595,000 | MLS #71384101 |
| Aug 1, 2012 | Price changed | $629,000 | MLS #71384101 |
| Jul 9, 2012 | Price changed | $649,000 | MLS #71384101 |
| May 16, 2012 | Listed | $675,000 | MLS #71384101 |
| Jul 28, 2008 | Sold | $590,000 | MLS #70733302 |
| Mar 27, 2008 | Listed | $629,000 | MLS #70733302 |
| Jul 29, 2005 | Sold | $580,000 | MLS #70169169 |
| Apr 7, 2005 | Listed | $569,000 | MLS #70169169 |
| Feb 23, 1990 | Sold | $206,000 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $1,110,900 | — | $1,110,900 | $10,965 |
| 2024 | $1,089,100 | — | $1,089,100 | $10,641 |
| 2023 | $1,053,000 | — | $1,053,000 | $10,498 |
| 2022 | $1,032,300 | — | $1,032,300 | $10,519 |
| 2021 | $1,022,200 | — | $1,022,200 | $10,018 |
| 2020 | $1,012,100 | — | $1,012,100 | $9,564 |
| 2019 | $963,900 | — | $963,900 | $9,032 |
| 2018 | $883,500 | — | $883,500 | $8,358 |
| 2017 | $818,100 | — | $818,100 | $8,083 |
| 2016 | $743,700 | — | $743,700 | $7,749 |
| 2015 | $676,100 | — | $676,100 | $7,221 |
| 2014 | $616,800 | — | $616,800 | $7,025 |
| 2006 | — | — | $499,100 | $4,766 |
| 2005 | — | — | $454,700 | $4,652 |
| 2004 | — | — | $425,000 | $4,518 |
| 2003 | — | — | $397,200 | $4,453 |
Property facts
Year built
1983
Property type
condo
Stories
1
Beds
2
Baths
2
Living area
1,197 sqft
Lot size
—
ZIP code
02446
City
Brookline
Street
Winchester St
Coordinates
42.34255, -71.12718
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsFrequently asked questions
When did 66 Winchester St last sell?
66 Winchester St most recently sold on Aug 31, 2012 for $595,000.
What is the current tax assessment for 66 Winchester St?
The most recent total assessment for 66 Winchester St (year 2025) is $1,110,900 with $10,965 in property tax.
How does 66 Winchester St's assessment compare to its last sale price?
The current assessment is 86.7% above the last sale price of $595,000.
When was 66 Winchester St built?
66 Winchester St was built in 1983.
How does 66 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 66 Winchester St?
66 Winchester St is a 2 bed, 2 bath, 1,197 sqft condo.
Is 66 Winchester St a flip candidate?
No — 66 Winchester St does not appear in our flips dataset.
Is 66 Winchester St a tax-appeal candidate?
No — 66 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
Other properties on Winchester St