91 Middlesex Rd, Brookline, MA 02467
Property image
Property image
OFF MARKET

91 Middlesex Rd
Brookline, MA 02467

Chestnut Hill
  • 9 Beds
  • 6.5 Baths
  • 8,607 sqft (on 0.28 acres)

$5,393,600

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $32,115/mo*
Refinance Your Home

$5,393,600

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $32,115/mo*
Refinance Your Home
9 Beds
6.5 Baths
8,607 sqft
(on 0.28 acres)

Home Value

Trulia Estimate
$5.39M
Since last month
Increased$14K (+0.3%)
Since last year
Increased$166K (+3.2%)
Since last sale
Increased$2M (+54.8%)
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 +24% in the last 10 years
MonthEstimated value
2026
August 2026$5.42M
July 2026$5.4M
June 2026$5.54M
May 2026$5.53M
April 2026$5.39M
March 2026$5.38M
February 2026$5.11M
January 2026$5.05M
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
23 Crafts Rd, Brookline, MA
0.19
Single-Family Home
$5,100,000
10/03/25
7
8
7,140
27 Suffolk Rd, Newton, MA
0.29
Single-Family Home
$4,400,000
09/10/25
6
4.5
5,520
98 Spooner Rd, Brookline, MA
0.34
Single-Family Home
$3,300,000
06/15/26
4
4.5
3,628
124 Chestnut Hill Rd, Newton, MA
0.33
Single-Family Home
$5,750,000
08/04/26
5
7.5
7,359
35 Jefferson Rd, Brookline, MA
0.28
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
59 Randolph Rd, Brookline, MA
0.32
Single-Family Home
$2,950,000
06/26/26
4
3.5
3,230
46 Malia Ter, Newton, MA
0.28
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
42 Lawrence Rd, Newton, MA
0.53
Single-Family Home
$4,200,000
05/05/26
6
4.5
4,874
3 Cleveland Rd, Brookline, MA
0.62
Single-Family Home
$4,600,000
05/04/26
5
6.5
4,300
9 Woodman Rd, Newton, MA
0.62
Single-Family Home
$5,462,500
09/05/25
6
7
7,016

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
138 Middlesex Rd #2, Chestnut Hill, MA 02467
0.11
$854,900
2
2
1,144
Off Market
142 Middlesex Rd #1, Chestnut Hill, MA 02467
0.12
$1,006,500
3
2
1,405
Off Market
136 Middlesex Rd #1, Chestnut Hill, MA 02467
0.13
$1,002,600
3
2
1,395
Off Market
37 Circuit Rd, Brookline, MA 02467
0.12
$4,764,900
6
5.5
5,382
Off Market
144 Middlesex Rd #2, Brookline, MA 02467
0.13
$895,500
3
2
1,400
Recently Sold
138 Middlesex Rd #3, Chestnut Hill, MA 02467
0.14
$842,200
3
1.5
1,300
Off Market
138 Middlesex Rd #1, Chestnut Hill, MA 02467
0.14
$762,300
3
1
1,350
Off Market
138 Middlesex Rd #B, Chestnut Hill, MA 02467
0.14
-
2
2
1,141
Off Market
10 Spooner Rd, Brookline, MA 02467
0.14
$5,998,200
6
6.5
7,285
Off Market
19 Crafts Rd, Brookline, MA 02467
0.17
$4,555,500
5
5.5
6,995
Off Market
76 Norfolk Rd, Brookline, MA 02467
0.17
$2,325,000
3
3
2,486
Recently Sold
215 Chestnut Hill Rd, Newton, MA 02467
0.19
$2,505,300
5
5.5
4,759
Off Market

Local Information

  • Map ViewExplore the area around 91 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1893
Lot Size
0.28 acres
Living Area
8,607 sqft
Price/Sqft
$627

About this House

One of Chestnut Hill's iconic homes with 9 bedrooms, 6 1/2 baths and 7 fireplaces has been updated for modern living. Offering the grandness of a more leisurely era reminiscent of the Great Gatsby with stunning architectural details throughout, the grand entry hall is flanked by banquet sized living and dining rooms complete with ornate fireplaces and rare millwork. Completing the 1st floor is a fire-placed family room with built ins and an eat in kitchen with custom cabinetry, high end appliances and french doors overlooking the private backyard with glorious perennial gardens and built-in hot tub. The second floor contains 5 fabulous bedrooms and 3 full bathrooms including a master suite with spa bath. Light flows through the etched glass skylights on the 3rd floor with 4 more bedrooms, an elegant office and 2 full baths. A singular offering around the corner from shopping, train, private and public schools in one of Brookline's most established neighborhoods.
91 Middlesex Rd, Brookline, MA 02467 is a 9 bedroom, 7 bathroom, 8,607 sqft single-family home in Chestnut Hill, built in 1893. It last sold for $3,500,000 on Aug 21, 2018. It is currently off market. The Trulia Estimate is $5,393,600, with a rent estimate of $4,955/month.

Home Details for 91 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 14
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1893Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Aug 21, 2018
Source: N/A
Sold
$3,500,000
Jun 12, 2018
Source: Agent Provided
Pending
$3,975,000
Apr 3, 2018
Source: Agent Provided
PriceChange
$3,975,000
Price decreased by 5%
Feb 12, 2018
Source: Agent Provided
Listed For Sale
$4,200,000
Dec 2, 2017
Source: Agent Provided
ListingRemoved
$4,475,000

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

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

  • 62 % Say it's quiet

  • 57 % Say there's wildlife

  • 55 % Say there are community events

  • 53 % 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

LGBTQ Local Legal Protections

Frequently asked questions about 91 Middlesex Rd

  • What is 91 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 91 Middlesex Rd in Brookline, MA is $5,393,600.
  • What is the price history for 91 Middlesex Rd?
    91 Middlesex Rd in Brookline, MA last sold for $3,500,000 in August 2018.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • How big is the lot at 91 Middlesex Rd?
    The lot at 91 Middlesex Rd in Brookline, MA is about 0.28 acres (12,196 sq ft).

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