385 Clinton Rd, Brookline, MA 02445
OFF MARKET

385 Clinton Rd
Brookline, MA 02445

Chestnut Hill
  • 5 Beds
  • 4.5 Baths
  • 4,300 sqft (on 0.26 acres)

$3,093,700

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $18,495/mo*
Refinance Your Home

$3,093,700

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $18,495/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,300 sqft
(on 0.26 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This single-family home is located at 385 Clinton Rd, Brookline, MA. 385 Clinton Rd is in the Chestnut Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 5 bedrooms, 5 bathrooms and approximately 4,300 sqft of floor space. This property has a lot size of 0.26 acres and was built in 1930.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 385 Clinton Rd

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 16Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office, Pantry, Recreation Room, Sun RoomStorage
Heating & Cooling
Heating: Baseboard, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: SlateExterior: WoodGardenLawnPatioSprinkler System
Parking & Garage
GarageParking: Garage Detached, Off Street, On Street

Property Information

Year Built
Year Built: 1930Year Updated: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Mobile R/V

RV Parking
Rv Parking

Price History for 385 Clinton Rd

DatePriceEventSource
10/31/2006$1,275,000Sold
N/A
11/29/2004$1,275,000Sold
N/A
04/03/1995$265,000Sold
N/A

Market trends in Brookline

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
Sale-to-List Price
99.0%
Price per sq ft
$809
Available listings
227
28MoM
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Property Tax and Assessment

Year2025
Tax$26,479
Assessment$2,682,800
Home facts updated by county records

Homeowner tools

Estimated monthly rent$8,352/mo
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Homes for rent near 385 Clinton Rd

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Comparable Sales for 385 Clinton Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Penniman Rd, Brookline, MA
0.04
Single-Family Home
$3,085,000
04/29/26
6
5.5
3,907
43 Druce St, Brookline, MA
0.35
Single-Family Home
$3,285,000
05/14/26
5
4.5
3,658
3 Cleveland Rd, Brookline, MA
0.22
Single-Family Home
$4,600,000
05/04/26
5
6.5
4,300
530 Clinton Rd, Brookline, MA
0.33
Single-Family Home
$3,250,000
07/15/25
6
3.5
4,033
167 Willard Rd, Brookline, MA
0.29
Single-Family Home
$3,400,000
09/23/25
4
3.5
3,298
265 Dean Rd, Brookline, MA
0.20
Single-Family Home
$4,500,000
06/11/25
6
4.5
5,744
92 Dean Rd, Brookline, MA
0.38
Single-Family Home
$2,336,000
07/07/25
6
3.5
3,161
218 Reservoir Rd, Brookline, MA
0.40
Single-Family Home
$1,810,000
07/31/25
5
2.5
2,522
333 Clark Rd, Brookline, MA
0.48
Single-Family Home
$2,487,000
12/11/25
5
3.5
3,100
34 Hyslop Rd, Brookline, MA
0.44
Single-Family Home
$4,125,000
05/28/26
5
4.5
4,001

Nearby homes

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Assigned Schools

These are the assigned schools for 385 Clinton Rd.
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.

Neighborhood Overview

Chestnut Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Chestnut Hill

At least 40 Trulia users voted on each feature.

  • 91 % Say there are sidewalks

  • 86 % Say it's dog friendly

  • 81 % Say car is needed

  • 73 % Say they plan to stay for at least 5 years

  • 71 % Say streets are well-lit

  • 70 % Say yards are well-kept

  • 70 % Say there's holiday spirit

  • 65 % Say people would walk alone at night

  • 65 % Say parking is easy

  • 63 % Say it's walkable to restaurants

  • 63 % Say kids play outside

  • 61 % Say it's quiet

  • 57 % Say there's wildlife

  • 55 % Say there are community events

  • 54 % Say it's walkable to grocery stores

  • 44 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • 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
  • 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
  • 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
  • Fish r.
    "Lovely neighborhood that's close to anything and everything -- shopping, restaurants, movies, doctors, gyms, public transportation, Soule recreation center & golf course, etc. Very safe, with lots of places to go for peaceful walks. I have lived here for nearly two decades and love it."
    5
    Flag
  • Jacquizieff
    "It an a upscale and snobby neighborhood where people don’t talk to each other. We never see kids and kids make no friends in the neighborhood. Clean safe closet To Boston. Nothing around. No walking distance to anything. Supermarket and gas is over priced. "
    0
    Flag
  • Robert B.
    "Wooded neighborhood surrounded by open space on 3 sides - farm stand and parks nearby. Safe, easy commute, great schools."
    0
    Flag

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Homes for sale near 385 Clinton Rd

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Off Market Homes Near 385 Clinton Rd

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385 Clinton Rd, Brookline, MA 02445 is a 5 bedroom, 5 bathroom, 4,300 sqft single-family home built in 1930. 385 Clinton Rd is located in Chestnut Hill, Brookline. This property is not currently available for sale. 385 Clinton Rd was last sold on Oct 31, 2006 for $1,275,000. The current Trulia Estimate for 385 Clinton Rd is $3,093,700.