86 Randolph Rd, Brookline, MA 02467
OFF MARKET

86 Randolph Rd
Brookline, MA 02467

Chestnut Hill
  • 5 Beds
  • 6 Baths
  • 4,658 sqft (on 0.72 acres)

$4,268,700

Trulia Estimate
as of Jul 6, 2026

$4,268,700

Trulia Estimate
as of Jul 6, 2026
5 Beds
6 Baths
4,658 sqft
(on 0.72 acres)

Local Information

  • Map ViewExplore the area around 86 Randolph Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This elegant Chestnut Hill home has beautiful garden views from almost every room. The lovely detailing includes French doors and windows, 6 fireplaces, 9' ceilings, solarium and butler?s pantry. The property is on 3/4 acre of private grounds with brick walled garden and mature landscaping. The Pre-War Construction qualities and details found here are not to be had in Recent Construction. From this private enclave, Boston is a short commute and its attractions, museums, symphony, only 15 mins.
86 Randolph Rd, Brookline, MA 02467 is a 5 bedroom, 6 bathroom, 4,658 sqft single-family home in Chestnut Hill, built in 1920. It last sold for $1,825,000 on Jan 20, 2010. It is currently off market. The Trulia Estimate is $4,268,700, with a rent estimate of $8,042/month.

Home Highlights

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

Home Details for 86 Randolph Rd

Interior Features

Interior Details
BasementNumber of Rooms: 13
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick

Property Information

Year Built
Year Built: 1920Year Updated: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.72 acres

Price History for 86 Randolph Rd

DatePriceEventSource
01/20/2010$1,825,000Sold
N/A
07/31/2009$2,275,000ListingRemovedAgent Provided
07/14/2009$2,275,000Listed For SaleAgent Provided

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$39,067
Assessment$3,958,200
Home facts updated by county records

Comparable Sales for 86 Randolph Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
35 Jefferson Rd, Brookline, MA
0.10
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
59 Randolph Rd, Brookline, MA
0.08
Single-Family Home
$2,950,000
06/26/26
4
3.5
3,230
46 Malia Ter, Newton, MA
0.53
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
23 Crafts Rd, Brookline, MA
0.22
Single-Family Home
$5,100,000
10/03/25
7
8
7,140
120 Cabot St, Brookline, MA
0.21
Single-Family Home
$5,700,000
11/25/25
6
7.5
8,849
130 Cabot St, Brookline, MA
0.23
Single-Family Home
$5,700,000
04/23/26
6
8
9,755
76 Norfolk Rd, Brookline, MA
0.21
Single-Family Home
$2,325,000
12/04/25
3
3
2,486
88 Cutler Ln, Brookline, MA
0.42
Single-Family Home
$5,860,000
02/18/26
6
6.5
7,450
335 Heath St, Brookline, MA
0.03
Single-Family Home
$7,650,000
12/11/25
7
8
12,814
27 Suffolk Rd, Newton, MA
0.65
Single-Family Home
$4,400,000
09/10/25
6
4.5
5,520

Nearby homes

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Assigned Schools

These are the assigned schools for 86 Randolph 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 41 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 yards are well-kept

  • 71 % Say streets are well-lit

  • 70 % Say there's holiday spirit

  • 66 % Say parking is easy

  • 66 % Say people would walk alone at night

  • 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

  • 43 % 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 86 Randolph Rd

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Off Market Homes Near 86 Randolph Rd

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