166 Chestnut St
-13.1%vs the Brookline ZIP median sale $/ft² ($777)
Sales Performance
7 arms-length sales on record for this building.
Unit Mix & Floor PlansThe building's recurring floor plans, found by grouping units with identical beds, baths and square footage in county records. Larger groups are the building's standard layouts; leftover units have one-off sizes.
Value DistributionHow the building's units spread across value ranges by our current estimates. A wide spread usually means big differences in size, floor or view.
Ownership & Financing
Recent SalesThe latest recorded arms-length sales in the building, newest first.
Values are TopHap estimates, not appraisals. Sales, ownership and tax figures come from recorded county documents via ATTOM and can lag by several weeks.
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Brookline School District
Neighborhood · ZIP 02445These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
All UnitsEvery property record the county has at this street address, such as the units in a condo building. Prices shown are our estimates, not asking prices.
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
About 166 Chestnut St
How many units are in 166 Chestnut St, Brookline, MA?
166 Chestnut St, Brookline, MA has 3 residential units across built in 1920, according to county assessor records.
What is a unit at 166 Chestnut St, Brookline, MA worth?
The median TopHap Estimate across the 3 units at 166 Chestnut St, Brookline, MA is $668,540. That works out to $675 per square foot. Units run from 948 to 1,146 square feet. Estimates are modelled from recorded sales and assessments, not appraisals.
Is 166 Chestnut St, Brookline, MA expensive for Brookline?
Units at 166 Chestnut St, Brookline, MA carry a median of $675 per square foot, 13% below the Brookline median of $777 per square foot.
How often do units sell at 166 Chestnut St, Brookline, MA?
0 units at 166 Chestnut St, Brookline, MA sold in the last 12 months, out of 7 recorded arms-length sales all time. That is a turnover rate of 0.0% of the building per year.
Have units at 166 Chestnut St, Brookline, MA appreciated?
Across 3 repeat sales of the same unit, 166 Chestnut St, Brookline, MA returned a median 11.5% per year. Because each pair is the same unit bought and sold, the figure is not distorted by which units traded. The median owner held for 4.1 years.
More homes on Chestnut St
- 124 Chestnut St # 2$897K3 bd · 1 ba · 1,232 ft² · Sold $900K · Apr 2026
- 91 Chestnut St # 4$570K2 bd · 1 ba · 718 ft² · Sold $580K · Aug 2025
- 70 Chestnut St # 3$1.1M3 bd · 2 ba · 1,660 ft² · Sold $1.2M · Aug 2024
- 91 Chestnut St # 3$467K2 bd · 1 ba · 718 ft² · Sold $475K · Jun 2024
- 91 Chestnut St # 62 bd · 1 ba · 718 ft² · Sold $525K · Apr 2024
- 92 Chestnut St$1.3M3 bd · 2.5 ba · 1,679 ft² · Sold $1.4M · Feb 2024
- 133 Chestnut St # 2$1.6M3 bd · 3.5 ba · 1,821 ft² · Sold $1.7M · Aug 2023
- 124 Chestnut St # 1$859K3 bd · 1.5 ba · 1,243 ft² · Sold $900K · Jul 2023
- 112 Chestnut St # 3$824K3 bd · 1 ba · 1,342 ft² · Sold $806K · Feb 2023
- 80 Chestnut St9 bd · 6 ba · 4,326 ft² · Sold $1.9M · Jul 2022
- 60 Chestnut St # 2$633K2 bd · 1 ba · 995 ft² · Sold $770K · Jun 2022
- 40 Chestnut St$1.2M3 bd · 1.5 ba · 1,272 ft² · Sold $337K · May 2022
Closest homes
- 166 Chestnut St$669K0 ft · 2 bd · 1 ba · 1,146 ft² · Sold $125K · Jul 1996
- 166 Chestnut St$640K0 ft · 2 bd · 1 ba · 948 ft² · Sold $167K · Jun 1998
- 162 Chestnut St33 ft · 8 bd · 3 ba · 3,588 ft² · Sold $175K · Sep 1987
- 231 High St55 ft · 9 bd · 4 ba · 5,233 ft² · Sold Jan 1900
- 229 High St50 ft · 8 bd · 4 ba · 3,482 ft² · Sold $975K · Aug 2013
- 225 High St64 ft · 5 bd · 3 ba · 3,057 ft² · Sold $290K · Oct 1997
- 160 Chestnut St69 ft · 6 bd · 3 ba · 4,212 ft² · Sold $173K · Oct 1985
- 331 Cypress St78 ft · 5 bd · 3 ba · 2,278 ft² · Sold $1.5M · Jul 2025
More homes in Brookline 02445
- 16 Kennard Rd$2M8 bd · 4 ba · 4,291 ft² · Sold $2M · Aug 2026
- 98 Boylston St$716K3 bd · 1 ba · 966 ft² · Sold $691K · Aug 2026
- 1778 Beacon St$940K2 bd · 1 ba · 1,157 ft² · Sold $940K · Aug 2026
- 56 Garrison Rd$560K1 bd · 1 ba · 767 ft² · Sold $549K · Aug 2026
- 63 Winthrop Rd$1.4M4 bd · 2 ba · 1,346 ft² · Sold $1.4M · Aug 2026
- 1731 Beacon St$765K2 bd · 1 ba · 985 ft² · Sold $765K · Aug 2026
- 168 Gardner Rd$2.9M4 bd · 3 ba · 2,868 ft² · Sold $2.9M · Aug 2026
- 1896 Beacon St$1.3M3 bd · 3 ba · 1,142 ft² · Sold $1.2M · Aug 2026
- 7 Regent Cir$706K1 bd · 1 ba · 940 ft² · Sold $705K · Jul 2026
- 11 Goodwin Pl$2.9M5 bd · 4 ba · 2,914 ft² · Sold $2.6M · Jul 2026
- 114 Davis Ave$1.3M3 bd · 2 ba · 1,247 ft² · Sold $1.3M · Jul 2026
- 38 Juniper St$501K2 bd · 1 ba · 822 ft² · Sold $502K · Jul 2026
Assigned schools
Explore the area
See this home in context
Open 166 Chestnut St on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map