75 Highland Rd, Brookline, MA 02445
OFF MARKET

75 Highland Rd
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 2 Baths
  • 1,000 sqft

$1,377,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,182/mo*
Refinance Your Home

$1,377,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,182/mo*
Refinance Your Home
3 Beds
2 Baths
1,000 sqft

Home Value

Trulia Estimate
$1.38M
Since last month
Decreased$18K (-1.3%)
Since last year
Increased$37K (+2.7%)
Since last sale
Increased$867K (+169.3%)
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 increased by +63% in the last 10 years
MonthEstimated value
2026
August 2026$1.38M
July 2026$1.4M
June 2026$1.4M
May 2026$1.43M
April 2026$1.42M
March 2026$1.39M
February 2026$1.34M
January 2026$1.31M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
71 Highland Rd, Brookline, MA
0.01
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
6 Fisher Ave, Roxbury, MA
0.98
Single-Family Home
$467,120
12/05/25
3
1.5
1,311
14-14A Linden Pl, Brookline, MA
0.66
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
18 Eldora St, Roxbury, MA
0.66
Single-Family Home
$863,000
10/10/25
4
1.5
2,149
27 Round Hill St, Jamaica Plain, MA
0.73
Single-Family Home
$1,070,000
08/28/25
4
1.5
1,569
209 High St, Brookline, MA
0.13
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
22 Edge Hill St, Jamaica Plain, MA
0.63
Single-Family Home
$1,175,000
05/13/26
3
2.5
1,235
18 Cushing Rd, Brookline, MA
0.46
Single-Family Home
$1,351,000
01/23/26
2
2
1,230
11 Kent Sq, Brookline, MA
0.89
Single-Family Home
$1,405,000
06/23/26
2
1.5
1,276
21 Starr Ln, Jamaica Plain, MA
0.98
Single-Family Home
$660,000
02/03/26
3
1
1,293

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
71 Highland Rd, Brookline, MA 02445
0.01
$950,000
3
1.5
1,000
Recently Sold
57-59 Highland Rd, Brookline, MA 02445
0.05
$1,949,000
4
3
1,949
For Sale
57 Highland Rd #2, Brookline, MA 02445
0.05
-
5
3.5
2,000
Off Market
45 Highland Rd #45, Brookline, MA 02445
0.07
-
3
1
911
Off Market
47 Highland Rd #47, Brookline, MA 02445
0.07
$815,000
3
1
981
Recently Sold
19 Edgehill Rd, Brookline, MA 02445
0.07
$3,875,500
5
4
3,538
Off Market
48 Jamaica Rd #3, Brookline, MA 02445
0.08
-
3
2
1,390
Off Market
35-37 Highland Rd, Brookline, MA 02445
0.09
-
6
2
2,152
Off Market
31 Highland Rd #1, Brookline, MA 02445
0.10
$2,320,000
3
3.5
2,500
Recently Sold
29-31 Highland Rd, Brookline, MA 02445
0.10
-
6
2
2,152
Off Market
29-31 Highland Rd, Brookline, MA 02445
0.10
-
3
3.5
2,537
Off Market
91 Glen Rd #1, Brookline, MA 02445
0.10
$1,155,800
3
2
1,520
Off Market

Local Information

  • Map ViewExplore the area around 75 Highland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1912
Living Area
1,000 sqft
Price/Sqft
$1,378

About this House

This single-family home is located at 75 Highland Rd, Brookline, MA. 75 Highland Rd is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 3 bedrooms, 2 bathrooms and approximately 1,000 sqft of floor space. This property has a lot size of 2613 sqft and was built in 1912.
75 Highland Rd, Brookline, MA 02445 is a 3 bedroom, 2 bathroom, 1,000 sqft single-family home in High Street Hill, built in 1912. It last sold for $512,000 on Jan 20, 2006. It is currently off market. The Trulia Estimate is $1,377,500, with a rent estimate of $4,712/month.

Home Details for 75 Highland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Dishwasher

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1912Year Updated: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 2613 sqft

Price and Tax history

DateEventPrice
Jan 20, 2006
Source: N/A
Sold
$512,000
Aug 10, 1993
Source: N/A
Sold
$202,500
Oct 30, 1987
Source: N/A
Sold
$168,000

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

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

Frequently asked questions about 75 Highland Rd

  • What is 75 Highland Rd estimated to be worth?
    Trulia's estimated value for 75 Highland Rd in Brookline, MA is $1,377,500.
  • What is the price history for 75 Highland Rd?
    75 Highland Rd in Brookline, MA last sold for $512,000 in January 2006.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • Does 75 Highland Rd have air conditioning?
    Yes, 75 Highland Rd in Brookline, MA has air conditioning.
  • How big is the lot at 75 Highland Rd?
    The lot at 75 Highland Rd in Brookline, MA is about 0.06 acres (2,613 sq ft).

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Apartments for Rent

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Off Market Homes Near 75 Highland Rd

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