145 Middlesex Rd, Brookline, MA 02467
OFF MARKET

145 Middlesex Rd
Brookline, MA 02467

Chestnut Hill
  • 6 Beds
  • 4.5 Baths
  • 4,848 sqft (on 0.34 acres)

$3,889,000

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $22,484/mo*
Refinance Your Home

$3,889,000

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $22,484/mo*
Refinance Your Home
6 Beds
4.5 Baths
4,848 sqft
(on 0.34 acres)

Local Information

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

Description

Set on a premier street in Brookline, this spectacular residence offers the perfect combination of gorgeous classic architecture and modern amenities. Set on over a third of an acre featuring beautifully landscaped gardens and an expansive deck (added in 2016) adding to the serene home. Substantially renovated, this home exudes quality workmanship and exquisite design that has an exceptional layout for today's lifestyle and formal entertaining. Fourteen rooms, six bedrooms - including a luxurious master bed/bath with a walk-in closet, and four and a half bathrooms The kitchen is appointed with high-end stainless-steel appliances, center island, and a breakfast nook. A detached double garage and a fully finished basement featuring a music room and media room (with 12 ft. motorized screen) were added in 2016. Close to Longwood Cricket Club, train, shops, and more. Heath School and Brookline High School.
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
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 145 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1904Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price History for 145 Middlesex Rd

DatePriceEventSource
08/21/2019$3,015,000Sold
N/A
06/11/2019$2,999,999PendingAgent Provided
06/04/2019$2,999,999Listed For SaleAgent Provided
07/02/2013$1,829,000Sold
N/A
04/16/2013$1,849,000Listed For SaleAgent Provided
03/10/2006$1,000,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$34,383
Assessment$3,483,600
Home facts updated by county records

Comparable Sales for 145 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
530 Clinton Rd, Brookline, MA
0.33
Single-Family Home
$3,250,000
07/15/25
6
3.5
4,033
46 Malia Ter, Newton, MA
0.16
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
401 Heath St, Brookline, MA
0.38
Single-Family Home
$2,750,000
06/11/25
5
3.5
4,028
533 Hammond St, Newton, MA
0.37
Single-Family Home
$3,550,000
06/20/25
5
5.5
5,772
35 Jefferson Rd, Brookline, MA
0.30
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
37 Randolph Rd, Brookline, MA
0.33
Single-Family Home
$2,650,000
06/17/25
5
4.5
3,430
409 Heath St, Brookline, MA
0.37
Single-Family Home
$3,475,000
06/06/25
5
3.5
3,500
10 Spooner Rd, Brookline, MA
0.04
Single-Family Home
$5,825,000
05/21/25
6
6.5
7,285
355 Hammond St, Newton, MA
0.49
Single-Family Home
$4,650,000
06/13/25
6
4.5
5,410
27 Suffolk Rd, Newton, MA
0.36
Single-Family Home
$4,400,000
09/10/25
6
4.5
5,520

Assigned Schools

These are the assigned schools for 145 Middlesex 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

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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Apartments for Rent

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Homes for sale near 145 Middlesex Rd

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Off Market Homes Near 145 Middlesex Rd

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Explore by feature

145 Middlesex Rd, Brookline, MA 02467 is a 6 bedroom, 5 bathroom, 4,848 sqft single-family home built in 1904. 145 Middlesex Rd is located in Chestnut Hill, Brookline. This property is not currently available for sale. 145 Middlesex Rd was last sold on Aug 21, 2019 for $3,015,000. The current Trulia Estimate for 145 Middlesex Rd is $3,889,000.