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

166 Chestnut St #1
Brookline, MA 02445

  • 3 Beds
  • 2 Baths
  • 1,079 sqft

$765,000

Last Sold: Jun 25, 2026
2% below list $779K
$709/sqft
Est. Refi. Payment $4,481/mo*
Refinance Your Home

$765,000

Last Sold: Jun 25, 2026
2% below list $779K
$709/sqft
Est. Refi. Payment $4,481/mo*
Refinance Your Home
3 Beds
2 Baths
1,079 sqft

Local Information

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

Description

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. It is currently off market. The Trulia Estimate is $835,700, with a rent estimate of $4,122/month.

Home Highlights

Parking
1 Parking Spaces
Outdoor
Porch
A/C
Heating & Cooling
HOA
$250/Monthly
Price/Sqft
$709/sqft
Listed
45 days ago

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
Last check for updates: about 20 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

Price History for 166 Chestnut St #1

DatePriceEventSource
06/25/2026$765,000Sold
MLS PIN #73518917
06/22/2026$779,000PendingMLS PIN #73518917
06/08/2026$779,000ContingentMLS PIN #73518917
05/28/2026$779,000PriceChange
MLS PIN #73518917
05/14/2026$799,000Listed For SaleMLS PIN #73518917
02/14/2023ListingRemovedZillow Rentals
02/08/2023$3,300Listed For RentZillow Rentals
11/29/2016$600,000Sold
N/A
09/30/2016$585,000Listed For SaleAgent Provided
07/21/2016$585,000ListingRemovedAgent Provided
07/06/2016$585,000Listed For SaleAgent Provided
09/21/2004$35,000Sold
N/A
08/31/2000$270,000Sold
N/A

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333MoM
Sale-to-List Price
99.9%
0.9%MoM
Price per sq ft
$814
$5MoM
Available listings
238
11MoM
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Property Tax and Assessment

Year2025
Tax$7,013
Assessment$710,500
Home facts updated by county records

Comparable Sales for 166 Chestnut St #1

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 W #4, Brookline, MA
0.29
Condo
$895,000
09/03/25
2
2
1,246
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

Nearby homes

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Assigned Schools

These are the assigned schools for 166 Chestnut St #1.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Luis B.
    "Lots of commerce within walking distance and easier access to the city by public transportation. Also very good public schools"
    0
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  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
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  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    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

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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

22 rentals with an outdoor space in Brookline, MA

Homes for sale near 166 Chestnut St #1

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Off Market Homes Near 166 Chestnut St #1

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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.