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)

$5,539,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $31,936/mo*
Refinance Your Home

$5,539,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $31,936/mo*
Refinance Your Home
9 Beds
6.5 Baths
8,607 sqft
(on 0.28 acres)

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

Description

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 $5,539,300, with a rent estimate of $4,296/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 91 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 14
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
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 History for 91 Middlesex Rd

DatePriceEventSource
08/21/2018$3,500,000Sold
N/A
06/12/2018$3,975,000PendingAgent Provided
04/03/2018$3,975,000PriceChange
Agent Provided
02/12/2018$4,200,000Listed For SaleAgent Provided
12/02/2017$4,475,000ListingRemovedAgent Provided
09/11/2017$4,475,000Listed For SaleAgent Provided
08/11/2017$4,475,000ListingRemovedAgent Provided
07/18/2017$4,475,000Listed For SaleAgent Provided
06/22/1998$1,770,000Sold
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$52,679
Assessment$5,337,300
Home facts updated by county records

Comparable Sales for 91 Middlesex Rd

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
530 Clinton Rd, Brookline, MA
0.46
Single-Family Home
$3,250,000
07/15/25
6
3.5
4,033
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 homes

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Assigned Schools

These are the assigned schools for 91 Middlesex Rd.
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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 91 Middlesex Rd

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Off Market Homes Near 91 Middlesex Rd

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