1 Chestnut Pl, Brookline, MA 02445
FOR SALE
0.57 ACRES

1 Chestnut Pl
Brookline, MA 02445

  • 6 Beds
  • 7 Baths
  • 7,780 sqft (on 0.57 acres)

$7,500,000

Est. Mortgage $42,771/mo*
Get Pre-Qualified

$7,500,000

Est. Mortgage $42,771/mo*
Get Pre-Qualified
6 Beds
7 Baths
7,780 sqft
(on 0.57 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

Home Highlights

Parking
3 Car Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$964
Listed
53 days ago

Home Details for 1 Chestnut Pl

Interior Features

Interior Details
Basement: Full,Finished,Walk-Out AccessNumber of Rooms: 25Types of Rooms: Master BathroomWet Bar
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 8Number of Bathrooms (full): 6Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 7780 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill HookupAppliances: Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Vacuum System, Range Hood, Water Softener, Plumbed For Ice MakerDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Radiant,Humidity Control,Natural Gas,Hydro AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Spa: PrivateHas a FireplaceHas a Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: French DoorsFlooring: Wood
Levels, Entrance, & Accessibility
Floors: Wood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, Deck - Wood, Patio, CoveredFencing: Fenced/Enclosed, FencedExterior: Porch, Deck - Wood, Patio, Covered Patio/Deck, Balcony, Pool - Inground Heated, Rain Gutters, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall, Outdoor Gas Grill HookupFoundation: Concrete PerimeterHas a Private PoolSprinkler System
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 10No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 13Parking: Attached,Garage Door Opener,Heated Garage,Paved Drive,Off Street,Paved
Pool
Pool: Pool - Inground HeatedPool
Frontage
Road Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 6155Finished Area (below surface): 1625

Days on Market

Days on Market: 53

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Shingle
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: B:329 L:0013 S:0000, 41225

Price & Status

Price
List Price: $7,500,000Price Per Sqft: $964

Active Status

MLS Status: Active

Location

Direction & Address
City: Brookline
School Information
Elementary School: LincolnJr High / Middle School: LincolnHigh School: Brookline Hs

Agent Information

Listing Agent
Listing ID: 73487838

Building

Building Area
Building Area: 7780 Square Feet

Community

Community Features: Public Transportation, Shopping, Park, Private School, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.57 acres

Miscellaneous

BasementMls Number: 73487838Above Grade Unfinished Area: 6155

Additional Information

Public TransportationShoppingParkPrivate SchoolPublic SchoolT-Station
Last check for updates: about 14 hours ago
Listing courtesy of Maggie Gold Seelig, (617) 645-4999
MGS Group Real Estate LTD, (617) 714-4544
Source: MLS PIN, MLS#73487838
Also Listed on MLS PIN.

Price History for 1 Chestnut Pl

DatePriceEventSource
03/17/2026$7,500,000Listed For SaleMLS PIN #73487838
10/16/2025$7,500,000ListingRemovedMLS PIN #73429741
09/11/2025$7,500,000Listed For SaleMLS PIN #73429741
08/29/2005$1,200,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$67,511
Assessment$6,840,000
Home facts updated by county records

Comparable Sales for 1 Chestnut Pl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
371 Walnut St, Brookline, MA
0.17
Single-Family Home
$5,250,000
03/02/26
7
5.5
6,193
469 Walnut St, Brookline, MA
0.33
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
125 Lee St, Brookline, MA
0.57
Single-Family Home
$4,650,000
08/18/25
7
7
7,147
235 Warren St, Brookline, MA
0.43
Single-Family Home
$4,300,000
06/27/25
6
5
8,029
21 Sargent Crossway, Brookline, MA
0.31
Single-Family Home
$7,030,000
04/03/26
5
6.5
5,772
80 Dudley St, Brookline, MA
0.44
Single-Family Home
$8,925,000
04/30/26
7
9
7,240
100 Cottage St, Brookline, MA
0.51
Single-Family Home
$5,790,000
12/19/25
6
7.5
9,380
27 Irving St, Brookline, MA
0.43
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
27 Walnut Pl, Brookline, MA
0.27
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
213 Gardner Rd, Brookline, MA
0.58
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507

Assigned Schools

These are the assigned schools for 1 Chestnut Pl.
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 421 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

  • 39 % Say car is needed

  • 39 % Say yards are well-kept

  • 33 % Say there are community events

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
    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
    Flag
  • 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.
    "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

LGBTQ Local Legal Protections

Maggie Gold Seelig, MGS Group Real Estate LTD, (617) 714-4544
Agent Phone: (617) 645-4999
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.
1 Chestnut Pl, Brookline, MA 02445 is a 6 bedroom, 8 bathroom, 7,780 sqft single-family home built in 2006. This property is currently available for sale and was listed by MLS PIN on Mar 17, 2026. The MLS # for this home is MLS# 73487838.