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

206 Middlesex Rd
Brookline, MA 02467

Chestnut Hill
  • 3 Beds
  • 3 Baths
  • 2,740 sqft

$2,368,200

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $14,193/mo*
Refinance Your Home

$2,368,200

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $14,193/mo*
Refinance Your Home
3 Beds
3 Baths
2,740 sqft

Local Information

  • Map ViewExplore the area around 206 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
1900
Living Area
2,740 sqft
Price/Sqft
$864
Parking
Garage

About this House

This single-family home is located at 206 Middlesex Rd, Brookline, MA. 206 Middlesex Rd is in the Chestnut Hill neighborhood in Brookline, MA and in ZIP code 02467. This property has 3 bedrooms, 3 bathrooms and approximately 2,740 sqft of floor space. This property has a lot size of 6969 sqft and was built in 1900.
206 Middlesex Rd, Brookline, MA 02467 is a 3 bedroom, 3 bathroom, 2,740 sqft single-family home in Chestnut Hill, built in 1900. More recently, it was listed as a rental in May 2023 with an asking price of $6,600 per month. That rental listing was removed on September 29, 2023. It is currently off market. The Trulia Estimate is $2,368,200, with a rent estimate of $6,681/month.

Home Details for 206 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 8
Appliances & Utilities
Dishwasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stucco, Brick
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1900Year Updated: 1979
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 6969 sqft

Price History for 206 Middlesex Rd

DatePriceEventSource
09/29/2023ListingRemovedZillow Rentals
05/30/2023$6,600Listed For RentZillow Rentals

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
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Property Tax and Assessment

Year2025
Tax$22,874
Assessment$2,317,500
Home facts updated by county records

Comparable Sales for 206 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
98 Spooner Rd, Brookline, MA
0.08
Single-Family Home
$3,300,000
06/15/26
4
4.5
3,628
174 Middlesex Rd, Newton, MA
0.07
Single-Family Home
$1,311,000
12/03/25
2
2
1,855
76 Norfolk Rd, Brookline, MA
0.33
Single-Family Home
$2,325,000
12/04/25
3
3
2,486
25 Chestnut Hill Rd, Newton, MA
0.35
Single-Family Home
$2,200,000
07/29/26
4
3.5
2,800
47 Nancy Rd, Newton, MA
0.44
Single-Family Home
$2,250,000
10/30/25
3
2.5
2,844
167 Willard Rd, Brookline, MA
0.37
Single-Family Home
$3,400,000
09/23/25
4
3.5
3,298
59 Randolph Rd, Brookline, MA
0.46
Single-Family Home
$2,950,000
06/26/26
4
3.5
3,230
35 Jefferson Rd, Brookline, MA
0.41
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
46 Malia Ter, Newton, MA
0.06
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
401 Clinton Rd, Brookline, MA
0.48
Single-Family Home
$2,200,000
06/15/26
5
3.5
3,463

Nearby homes

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Assigned Schools

These are the assigned schools for 206 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 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

Apartments for Rent

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Explore by feature - Pet Friendly

319 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

70 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

540 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

68 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

781 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

24 rentals with an outdoor space in Brookline, MA

Homes for sale near 206 Middlesex Rd

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Off Market Homes Near 206 Middlesex Rd

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Frequently asked questions about 206 Middlesex Rd

  • What is 206 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 206 Middlesex Rd in Brookline, MA is $2,368,200.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.4M. That is down $16.67K from the prior month.
  • What do residents say about the Chestnut Hill neighborhood?
    Residents describe the Chestnut Hill neighborhood in Brookline, MA as pedestrian-friendly, dog-friendly, and established. See recently sold homes in Chestnut Hill, Brookline.
  • How big is the lot at 206 Middlesex Rd?
    The lot at 206 Middlesex Rd in Brookline, MA is about 0.16 acres (6,969 sq ft).
  • Does 206 Middlesex Rd have a garage?
    Yes, 206 Middlesex Rd in Brookline, MA has a garage.