145 Middlesex Rd, Chestnut Hill, MA 02467
OFF MARKET

$2,652,000

Trulia Estimate
  • 6 Beds
  • 4.5 Baths
  • 4,300 sqft (on 0.39 acres)

145 Middlesex Rd, Chestnut Hill, MA 02467

Chestnut Hill
Est. Refi. Payment $15,759/mo*
Refinance Your Home
Currently Off Market - Sold Aug 21, 2019 for $3,015,000

Home Value

Trulia Estimate
$2.65M
Since last month
Increased$44K (+1.6%)
Since last year
Increased$5K (+0.2%)
Since last sale
Decreased$329K (-10.9%)
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 decreased by -18% in the last 10 years
MonthEstimated value
2026
August 2026$2.69M
August 2026$2.65M
July 2026$2.64M
June 2026$3.05M
May 2026$2.86M
April 2026$3.11M
March 2026$2.84M
February 2026$3.57M
January 2026$2.92M
2025
2024
2023
2021

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
46 Malia Ter, Newton, MA
0.16
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
98 Spooner Rd, Brookline, MA
0.21
Single-Family Home
$3,300,000
06/15/26
4
4.5
3,628
35 Jefferson Rd, Brookline, MA
0.30
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
59 Randolph Rd, Brookline, MA
0.35
Single-Family Home
$2,950,000
06/26/26
4
3.5
3,230
27 Suffolk Rd, Newton, MA
0.36
Single-Family Home
$4,400,000
09/10/25
6
4.5
5,520
8 Penniman Rd, Brookline, MA
0.65
Single-Family Home
$3,085,000
04/29/26
6
5.5
3,907
76 Norfolk Rd, Brookline, MA
0.20
Single-Family Home
$2,325,000
12/04/25
3
3
2,486
520 Clinton Rd, Brookline, MA
0.36
Single-Family Home
$2,394,900
08/21/26
4
3.5
2,996
42 Lawrence Rd, Newton, MA
0.60
Single-Family Home
$4,200,000
05/05/26
6
4.5
4,874
167 Willard Rd, Brookline, MA
0.48
Single-Family Home
$3,400,000
09/23/25
4
3.5
3,298

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
10 Spooner Rd, Brookline, MA 02467
0.04
$6,031,500
6
6.5
7,285
Off Market
138 Middlesex Rd #3, Chestnut Hill, MA 02467
0.03
$786,000
3
1.5
1,300
Off Market
138 Middlesex Rd #1, Chestnut Hill, MA 02467
0.03
$679,100
3
1
1,350
Off Market
142 Middlesex Rd #1, Chestnut Hill, MA 02467
0.02
$934,100
3
2
1,405
Off Market
138 Middlesex Rd #B, Chestnut Hill, MA 02467
0.03
-
2
2
1,141
Off Market
136 Middlesex Rd #1, Chestnut Hill, MA 02467
0.03
$932,600
3
2
1,395
Off Market
144 Middlesex Rd #2, Brookline, MA 02467
0.03
$895,500
3
2
1,400
Recently Sold
138 Middlesex Rd #2, Chestnut Hill, MA 02467
0.03
$771,000
2
2
1,144
Off Market
174 Middlesex Rd, Newton, MA 02467
0.08
$1,311,000
2
2
1,855
Recently Sold
37 Circuit Rd, Brookline, MA 02467
0.10
$4,811,900
6
5.5
5,382
Off Market
195 Middlesex Rd, Brookline, MA 02467
0.12
$5,213,100
6
5
5,822
Off Market
96 Crafts Rd, Brookline, MA 02467
0.12
$5,593,600
6
4.5
6,313
Off Market

Local Information

  • Map ViewExplore the area around 145 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1862
0.39 acre lot
4,300 sqft
$617/sqft

About this House

This single-family home is located at 145 Middlesex Rd, Chestnut Hill, MA. 145 Middlesex Rd is in the Chestnut Hill neighborhood in Chestnut Hill, MA and in ZIP code 02467. This property has 6 bedrooms, 5 bathrooms and approximately 4,300 sqft of floor space. This property has a lot size of 0.39 acres and was built in 1862.
145 Middlesex Rd, Chestnut Hill, MA 02467 is a 6 bedroom, 5 bathroom, 4,300 sqft single-family home in Chestnut Hill, built in 1862. It last sold for $3,015,000 on Aug 21, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,652,000.

Home Details for 145 Middlesex Rd

Property Information

Year Built
Year Built: 1862
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Aug 21, 2019
Source: N/A
Sold
$3,015,000

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 145 Middlesex Rd

  • What is 145 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 145 Middlesex Rd in Chestnut Hill, MA is $2,652,000.
  • What is the price history for 145 Middlesex Rd?
    145 Middlesex Rd in Chestnut Hill, MA last sold for $3,015,000 in August 2019.
  • Is Chestnut Hill a buyer's or seller's market?
    Chestnut Hill is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Chestnut Hill?
    The median sale price in Chestnut Hill is $1.22M. That is down $182K from the prior month.
  • How big is the lot at 145 Middlesex Rd?
    The lot at 145 Middlesex Rd in Chestnut Hill, MA is about 0.39 acres (17,000 sq ft).

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Off Market Homes Near 145 Middlesex Rd

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