166 Chestnut St #1, Brookline, MA 02445
Property image
Property image
SOLD
JUN 25, 2026

$768,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,079 sqft

166 Chestnut St #1, Brookline, MA 02445

Est. Refi. Payment $4,847/mo*
Refinance Your Home
Currently Off Market - Sold Jun 25, 2026 for $765,000 (2% below list price)

Home Value

Trulia Estimate
$769K
Since last month
Increased$10K (+1.3%)
Since last year
Decreased$59K (-7.2%)
Since last sale
Increased$4K (+0.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +29% in the last 10 years
MonthEstimated value
2026
September 2026$769K
August 2026$759K
July 2026$767K
June 2026$836K
May 2026$813K
April 2026$840K
March 2026$839K
February 2026$824K
January 2026$825K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
124 Chestnut St #2, Brookline, MA
0.10
Condo
$900,000
04/21/26
3
1
1,232
47 Highland Rd #47, Brookline, MA
0.21
Condo
$815,000
11/26/25
3
1
981
20 Rice St #2, Brookline, MA
0.24
Condo
$740,000
05/14/26
3
1
978
30 Cumberland Ave #3W, Brookline, MA
0.29
Condo
$899,000
10/20/25
2
2
1,246
71 Parkton Rd #2, Jamaica Plain, MA
0.37
Condo
$989,000
05/07/26
3
1.5
1,325
60 Glen Rd #108, Brookline, MA
0.31
Condo
$900,000
05/14/26
2
2
1,249
241 Perkins St #C306, Jamaica Plain, MA
0.25
Condo
$1,300,000
02/03/26
3
2
1,876

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
7 Henry St, Brookline, MA 02445
0.02
-
6
2.5
2,328
Off Market
11-13 Henry St, Brookline, MA 02445
0.03
-
5
2
2,136
Off Market
12 Henry St #2, Brookline, MA 02445
0.04
-
3
2
1,283
Off Market
12 Henry St #3, Brookline, MA 02445
0.04
-
3
2
1,913
Off Market
12 Henry St #A, Brookline, MA 02445
0.04
-
2
2
1,155
Off Market
112 Franklin St #3, Brookline, MA 02445
0.06
$916,200
3
1
1,099
Off Market
209 High St, Brookline, MA 02445
0.05
$2,150,000
4
3.5
2,332
Recently Sold
106 Franklin St #2, Brookline, MA 02445
0.06
$823,300
3
1
985
Off Market
106 Franklin St #3, Brookline, MA 02445
0.06
$815,400
3
1
985
Off Market
133 Chestnut St #2, Brookline, MA 02445
0.08
$1,701,500
3
3.5
1,925
Off Market
203 High St, Brookline, MA 02445
0.06
$2,034,000
9
3
3,738
Off Market

Local Information

  • Map ViewExplore the area around 166 Chestnut St #1.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1920
1,079 sqft
$709/sqft
1 Parking Spaces
HOA $250/mo

About this House

What's unique:Dine-in kitchenHardwood floorsRich period detailsTimeless appealUpdated appliancesHigh ceilings
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.
166 Chestnut St #1, Brookline, MA 02445 is a 3 bedroom, 2 bathroom, 1,079 sqft condo built in 1920. It last sold for $765,000 on Jun 25, 2026 (2% below the $779,000 asking price). More recently, it was listed as a rental in February 2023 with an asking price of $3,300 per month. That rental listing was removed on February 14, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $768,500, with a rent estimate of $4,340/month.
Last check for updates: about 2 hours ago
Listed by Jean Fan, (781) 971-3668
Blue Ocean Realty, LLC, (617) 206-5700
Monica Chen, (857) 498-0741
Bought with: Kopman Adler Team, (617) 309-9495, Compass, (617) 206-3333
Source: MLS PIN, MLS#73518917

Home Details for 166 Chestnut St #1

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1079 Square Feet
Appliances & Utilities
Laundry: First Floor,In Unit
Heating & Cooling
Heating: Baseboard,Natural GasHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
No FireplaceNo Spa
Levels, Entrance, & Accessibility
Number of Stories: 1

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PorchExterior: Porch
Parking & Garage
Open Parking Spaces: 1No GarageParking Spaces: 1
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1079

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: ResidentialProperty Subtype: CondominiumStructure Type: Low-RiseArchitecture: Low-Rise
Building
Building Name: 166 Chestnut Street Condo AssociationConstruction Materials: FrameDoes Not Include Home Warranty
Property Information
Parcel Number: 34709404, 40574

Price & Status

Price
List Price: $779,000Price Per Sqft: $709/sqft
Status Change & Dates
Off Market Date: Sun Jun 21 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Brookline
School Information
Elementary School: William H. Lincoln SchoolHigh School: Brookline High School

Building

Building Area
Building Area: 1079 Square Feet

Community

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, UniversityNot Senior Community

HOA

HOA Fee Includes: Water, Sewer, Insurance, Maintenance Grounds, Snow RemovalHOA Fee: $250/Monthly

Lot Information

Lot Area: 2295.6841 Acres

Offer

Contingencies: Inspection

Miscellaneous

BasementMls Number: 73518917Above Grade Unfinished Area: 1079

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsGolfMedical FacilityLaundromatBike PathHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity

Price and Tax history

DateEventPrice
Jun 25, 2026
Source: MLS PIN #73518917
Sold
$765,000
Jun 22, 2026
Source: MLS PIN #73518917
Pending
$779,000
Jun 8, 2026
Source: MLS PIN #73518917
Contingent
$779,000
May 28, 2026
Source: MLS PIN #73518917
PriceChange
$779,000
Price decreased by 3%
May 14, 2026
Source: MLS PIN #73518917
Listed For Sale
$799,000

Market trends in Brookline

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.24M
$23.33KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$811
$6MoM
Available listings
186
30MoM

Around this home

What Locals Say about Brookline

At least 422 Trulia users voted on each feature.

  • 94 % Say there are sidewalks

  • 90 % Say it's dog friendly

  • 87 % Say it's walkable to restaurants

  • 87 % Say it's walkable to grocery stores

  • 84 % Say people would walk alone at night

  • 81 % Say streets are well-lit

  • 67 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 59 % Say there's wildlife

  • 52 % Say parking is easy

  • 51 % Say they plan to stay for at least 5 years

  • 51 % Say it's quiet

  • 48 % Say neighbors are friendly

  • 40 % Say car is needed

  • 39 % Say yards are well-kept

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Rockygranahan
    "A quick and easy walk to the T. Total commute to downtown Boston from Coolidge Corner ranges between 15-25 minutes consistently."
    0
    Flag
  • Kai Hsin Chang
    "Very convenient to do grocery and most people live here use public transportation because there’s no street parking. People who want to do street parking should apply for parking permits."
    0
    Flag
  • Sydney Reitz
    "Events at the Coolidge corner theatre, Brookline day on Harvard street in Coolidge corner, open holiday meals at the United Parish church"
    0
    Flag
  • Sydney Reitz
    "The sidewalks and streets are well-maintained even in inclement weather. Traffic is only bad around the Longwood medical area and major streets around rush hour. Pub trans is easy and safe."
    0
    Flag
  • Austin Wozniak
    "Multiple dog friendly, off-leash parks in the community and many great places to walk a dog. The community is very dog friendly. "
    0
    Flag
  • Loming1986
    "Only limited (a hand-full) dog parks available, I wish there are more. Many neighbors have dogs and it’s a very dog friendly neighborhood."
    0
    Flag
  • Trulia User
    "Clean, safe and quiet. People are very friendly. Access ti public transportation. Love this place very much."
    0
    Flag
  • Trulia User
    "The neighborhood is great environment to raise a family. It’s peaceful, clean and quiet. We would love to be here to raise our kids here. "
    0
    Flag
  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
    0
    Flag
  • Trulia User
    "Near everything. Train across the street, restaurants, coffee shops, etc JP is part of Boston. Vibrant community. Diverse. High incomes mixed with low. "
    1
    Flag
  • Trulia User
    "Yes, the area has many dog parks, both on and off leash. Most apartment buildings are dog friendly and neighbors have been very accepting. "
    0
    Flag
  • Aliana P.
    "It’s a quick commute to downtown, especially if you live on the D line. Very convenient. It’s also a very walkable area with all stores and necessities close by. "
    1
    Flag
  • Juana B.
    "It’s very safe and great school system!! I been leaving here for 11 years and I love it and my kids too"
    2
    Flag
  • Jiyoung W.
    "Lots of other friendly dog owners, plus lots of little parks and green space for pups to run around (especially Amory Park!). Lots of businesses in the area have dog treat jars too!"
    1
    Flag
  • Adriana P.
    "It seems let friendly. Lots of parks and spaces for dogs to run. I don’t have a dog but I have friends with dogs"
    0
    Flag
  • Archana B.
    "Lived here for 5 years. I highly recommend it. It is getting more expensive. Some areas are more family friendly than others. "
    0
    Flag
  • Deiabarroso86
    "Very safe, with a lot of stores around.. Beacon Street is a beautiful street and we have the Reservoir nearby, which is a good place for a walk."
    1
    Flag
  • Josie E.
    "The kids walk to school on a tree-lined street and neighbors know each other. A little oasis in the city "
    4
    Flag
  • Caroline
    "Drive to Watertown or take shuttle provided by my place of employment. Easy access to city via C or D green line. "
    0
    Flag
  • Dma333
    "Diverse, safe, close to everything, friendly neighbors, great schools, playgrounds in walking distance"
    0
    Flag
  • Steve L.
    "Hancock Village in Chestnut Hill is a good place to live overall. Sometimes the management office puts together special functions like handing out cider doughnuts in the fall, or flowers to plant - both gratis. (And more as well but too much to detail)."
    4
    Flag
  • Dma333
    "Block party in September Close to a great school Playgrounds nearby Diverse community Easy access to many communities "
    1
    Flag
  • Szonja.ruppert
    "Lots of greens, parks, even bags for dogpoop is put to parks. Not many pet shops in walking distance"
    0
    Flag
  • Scottcunha311
    "Halloween’s are very popular especially on clark rd. Great location to Cleveland circle and both bu and bc can take train anywhere or easily get a bus there’s no shortsge of things to do"
    0
    Flag
  • Jawaher A.
    "Good schools, no stealing, good neighbors, good place to kids to play, not far away from BU university, there is driving school, all government facilities around us, Uber so expensive but it is available all time, there is ice cream shop and Starbucks around us also a lot of restaurants and malls "
    2
    Flag
  • Courtney C.
    "Safe and homey - education is good but property tax is rising. Commute is perfect - only ten minute drive away from my work site. "
    0
    Flag
  • Luis B.
    "Lots of commerce within walking distance and easier access to the city by public transportation. Also very good public schools"
    0
    Flag
  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
    0
    Flag
  • Jawaher A.
    "I love this area coz its safe and beautiful and the neighbors are nice and kind and there is a lot of great people "
    0
    Flag
  • Oliver L.
    "I walk to work in the medical area. T stops make getting to the center easy. It is quite possible to live without a car."
    0
    Flag
  • Sophie
    "The community center holds a lot of interesting activities like Mahjong, movies, reading, yoga and concerts. Also we have a greeeat library here!"
    0
    Flag
  • Kathy U.
    "Many dog parks around the Coolidge corner area. Many off leash areas too. The dog community it big in this neighborhood "
    0
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  • Heli C.
    "The schools are excellent, and neighbors tend to know each other. We are a ‘suburb’ of Boston but also officially a town with numerous distinct village neighborhoods, most of which are walkable to restaurants and amenities. Brookline has a fairly international mix of people, with families from all over the world coming here to study and work at the nearby Harvard teaching hospitals."
    0
    Flag
  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
    Flag
  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
    1
    Flag

LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 166 Chestnut St #1

  • What is 166 Chestnut St #1 estimated to be worth?
    Trulia's estimated value for 166 Chestnut St #1 in Brookline, MA is $768,500.
  • What is the price history for 166 Chestnut St #1?
    166 Chestnut St #1 in Brookline, MA last sold for $765,000 in June 2026.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.24M. That is up $23.33K from the prior month.
  • Does 166 Chestnut St #1 have air conditioning?
    Yes, 166 Chestnut St #1 in Brookline, MA has air conditioning.
  • Does 166 Chestnut St #1 have a pool?
    Yes, 166 Chestnut St #1 in Brookline, MA has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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