For sale

$799,000

166 Chestnut St #1, Brookline, MA 02445

3beds

1,079sqft

Est.:

Condominium

Built in 1920

-- sqft lot

$785,400 Zestimate^®

$741/sqft

$250/mo HOA

What's special

Dine-in kitchenHardwood floorsRich period detailsTimeless appealUpdated appliancesHigh ceilingsBeautiful window moldings

Spacious 3-bed, 2-bath condo with one off-street parking space, ideally located near Brookline Village. This updated unit is a true gem in an exceptional location! The dine-in kitchen features updated appliances, while rich period details throughout—including beautiful window moldings, ceiling medallions, hardwood floors, and high ceilings—enhance the home’s gracious layout and timeless appeal. Additional highlights include an oversized finished storage unit in the basement. The pet-friendly building adds even more convenience and appeal.Exceptional commuter location just moments from Brookline Village and Brookline Hills with convenient Green Line access for an easy commute to Fenway, downtown Boston, and beyond. MBTA 60 Bus to Longwood Medical Area is at your door step. Enjoy nearby shops, cafés, parks, and neighborhood amenities right outside your door.

1 day

316

15

Tour with a local agent

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Primary bedroom

Level: First

Bedroom 2

Level: First

Bedroom 3

Level: First
Length: 16

Bathroom 1

Level: First

Bathroom 2

Level: First

Dining room

Level: First

Kitchen

Level: First

Living room

Level: First
Length: 15

Heating

Baseboard, Natural Gas

Cooling

Window Unit(s)

Appliances

Laundry: First Floor, In Unit

Features

Entry Hall
Has basement: Yes
Has fireplace: No

Interior area

Total structure area: 1,079
Total interior livable area: 1,079 sqft
Finished area above ground: 1,079

Property

Parking

Total spaces: 1
Uncovered spaces: 1

Features

Patio & porch: Porch
Exterior features: Porch

Lot

Size: 2,295.68 Acres

Details

Parcel number: 34709404,40575
Zoning: 102

Construction

Type & style

Home type: Condo
Property subtype: Condominium

Materials

Frame
Roof: Shingle

Condition

Year built: 1920

Utilities & green energy

Sewer: Public Sewer
Water: Public

Community & HOA

Community

Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Highway Access, House of Worship, Private School, Public School, T-Station, University

HOA

Services included: Water, Sewer, Insurance, Maintenance Grounds, Snow Removal
HOA fee: $250 monthly

Location

Region: Brookline

Financial & listing details

Price per square foot: $741/sqft
Tax assessed value: $747,100
Annual tax amount: $7,650
Date on market: 5/14/2026

Estimated market value

$785,400

$746,000 - $825,000

$4,610/mo

Price history

Date	Event	Price
5/14/2026	Listed for sale	$799,000+33.2%$741/sqft
Source: MLS PIN #73518917 Report a problem
2/14/2023	Listing removed	--
Source: Zillow Rentals Report a problem
2/8/2023	Listed for rent	$3,300$3/sqft
Source: Zillow Rentals Report a problem
11/29/2016	Sold	$600,000+2.6%$556/sqft
Source: Public Record Report a problem
9/30/2016	Listed for sale	$585,000$542/sqft
Source: Appraisals Unlimited, Inc #72073407 Report a problem
7/21/2016	Listing removed	$585,000$542/sqft
Source: Hammond Residential R. E. #72033416 Report a problem
7/6/2016	Listed for sale	$585,000+1571.4%$542/sqft
Source: Hammond Residential R. E. #72033416 Report a problem
9/21/2004	Sold	$35,000-87%$32/sqft
Source: Public Record Report a problem
8/31/2000	Sold	$270,000$250/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$7,013 +3.1%	$710,500 +2%
2024	$6,805 +6.6%	$696,500 +8.8%
2023	$6,384 +0.8%	$640,300 +3%
2022	$6,335 +5%	$621,700 +1%
2021	$6,033 +4.7%	$615,600 +1%
2020	$5,760 +5.9%	$609,500 +5%
2019	$5,439 +4%	$580,500 +5%
2018	$5,229 +3.4%	$552,800 +8%
2017	$5,058 +4.3%	$511,900 +10%
2016	$4,848 +7.3%	$465,300 +10%
2015	$4,518 +0.1%	$423,000 +6.7%
2014	$4,515 +2.7%	$396,400 +5%
2013	$4,398 +2.2%	$377,500
2012	$4,304 +1.9%	$377,500 +1%
2011	$4,225 +3%	$373,900
2010	$4,102 +2.6%	$373,900
2009	$3,997 +9.5%	$373,900 +4.3%
2008	$3,651 +1.6%	$358,600 -2.9%
2007	$3,593	$369,300

Find assessor info on the county website

Monthly payment

Est. payment

Payment breakdown

Explore the cost of this home by adjusting the details. Changes won't be saved.

All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

See how much you could borrow to make a competitive offer.

Get pre-qualified