166 Chestnut St
-9.9%vs the Brookline ZIP median sale $/ft² ($749)
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, 10% below the Brookline median of $749 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$640K0 ft · 2 bd · 1 ba · 948 ft² · Sold $167K · Jun 1998
- 166 Chestnut St$669K0 ft · 2 bd · 1 ba · 1,146 ft² · Sold $125K · Jul 1996
- 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
- 331 Goddard Ave$1.8M3 bd · 2.5 ba · 2,552 ft² · Sold $1.6M · Aug 2026
- 23 Strathmore Rd$1.3M3 bd · 2 ba · 1,600 ft² · Sold $1.3M · Aug 2026
- 38 Kilsyth Rd$500K1 bd · 1 ba · 554 ft² · Sold $500K · Aug 2026
- 77 Pond Ave$475K1 bd · 1 ba · 710 ft² · Sold $475K · Aug 2026
- 157 Cypress St$1.8M4 bd · 3.5 ba · 2,075 ft² · Sold $1.8M · Aug 2026
- 54 Regent Cir2 bd · 2.5 ba · 1,928 ft² · Sold $1.4M · Aug 2026
- 231 Rawson Rd$780K2 bd · 1 ba · 947 ft² · Sold $780K · Aug 2026
- 24 Juniper St$295K1 bd · 1 ba · 638 ft² · Sold $221K · Aug 2026
- 71 Avon St$4.4M4 bd · 3.5 ba · 2,402 ft² · Sold $3.1M · Aug 2026
- 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
Assigned schools
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