95 Highland Rd, Brookline, MA 02445
OFF MARKET

95 Highland Rd
Brookline, MA 02445

High Street Hill
  • 2 Beds
  • 1 Bath
  • 960 sqft

$1,219,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $7,117/mo*
Refinance Your Home

$1,219,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $7,117/mo*
Refinance Your Home
2 Beds
1 Bath
960 sqft

Local Information

  • Map ViewExplore the area around 95 Highland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Storybook Pill Hill historic district c1920 attached brick 1000+/- sq ft two bedroom, one bathroom single-family house with private deck, perennial and berry gardens, garage and two outdoor parking spaces, abutting a private circle containing joint-ownership association open land. Designed by noted architect Walter Kilham as a model artistic working class housing design, and offering an open floor plan with much charm and architectural interest. Basement offers a family room and areas currently used for office & exercise. Full attic storage and expansion potential. Stellar location near Brookline Village's restaurants, shops, MBTA "D" line & buses and main library, and close to the Longwood medical area and the Lincoln and Brookline High Schools. The lush greenery of Olmsted Park, Downes Field running track and dog park, playgrounds and Jamaica Pond all at your doorstep.
95 Highland Rd, Brookline, MA 02445 is a 2 bedroom, 1 bathroom, 960 sqft single-family home in High Street Hill, built in 1920. It last sold for $786,500 on Nov 15, 2016. It is currently off market. The Trulia Estimate is $1,219,400, with a rent estimate of $3,790/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 95 Highland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1920Year Updated: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 2178 sqft

Price History for 95 Highland Rd

DatePriceEventSource
11/15/2016$786,500Sold
N/A
09/23/2016$789,000PendingAgent Provided
09/13/2016$789,000Listed For SaleAgent Provided
12/30/2003$397,500Sold
N/A
08/01/2003$382,500Sold
N/A
12/14/2000$287,625Sold
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$11,882
Assessment$1,203,800
Home facts updated by county records

Comparable Sales for 95 Highland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Highland Rd, Brookline, MA
0.03
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
39 School St, Brookline, MA
0.65
Single-Family Home
$1,005,000
08/19/25
3
1
1,576
18 Cushing Rd, Brookline, MA
0.42
Single-Family Home
$1,351,000
01/23/26
2
2
1,230
21 Starr Ln, Jamaica Plain, MA
1.00
Single-Family Home
$660,000
02/03/26
3
1
1,292
15 Kent Sq, Brookline, MA
0.89
Single-Family Home
$1,501,000
04/17/26
2
2
1,276
24 Goldsmith St, Jamaica Plain, MA
1.26
Single-Family Home
$640,000
10/30/25
2
1
816
11 Kent Sq, Brookline, MA
0.89
Single-Family Home
$1,405,000
06/23/26
2
1.5
1,276
22 Edge Hill St, Jamaica Plain, MA
0.66
Single-Family Home
$1,175,000
05/13/26
3
2.5
1,235
209 High St, Brookline, MA
0.11
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
14-14A Linden Pl, Brookline, MA
0.66
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380

Nearby homes

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Assigned Schools

These are the assigned schools for 95 Highland 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

High Street Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about High Street Hill

At least 31 Trulia users voted on each feature.

  • 98 % Say there are sidewalks

  • 97 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 89 % Say streets are well-lit

  • 88 % Say it's walkable to restaurants

  • 88 % Say it's walkable to grocery stores

  • 85 % Say kids play outside

  • 63 % Say there's holiday spirit

  • 54 % Say neighbors are friendly

  • 49 % Say they plan to stay for at least 5 years

  • 48 % Say it's quiet

  • 46 % Say there's wildlife

  • 45 % Say parking is easy

  • 42 % Say yards are well-kept

  • 40 % Say car is needed

  • 37 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

355 pet-friendly rentals in Brookline, MA

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

23 rentals with an outdoor space in Brookline, MA

Homes for sale near 95 Highland Rd

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Off Market Homes Near 95 Highland Rd

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