OFF MARKET

Off Market Aug 2022 for $1.4M

$1,195,545

•

2,152

sq ft

29-31 Highland Rd, Brookline, MA 02445

About this home

Located in a very sought-after area of Brookline, this beautiful renovated 2-family home offers convenient access to Downes Field, Brookline Village, and the Jamaica Pond. Both units feature 3 bedrooms, 1 full bathroom, a garage, and additional outside parking. In addition to the newly-renovated kitchens with stone countertops, the living. dining and kitchen are all open to each other, creating a natural flow. You will find the bedrooms are large with spacious closets. Each unit has a private outdoor space in the secluded rear of the property. In the entryway of the home, there is a spacious, newly replaced deck. The basement features laundry facilities, separate systems, and a 2-car garage with extra storage space. Investors and end-users alike will love this property. First open houses are on 5/28 & 5/29.

Multi-familyProperty Type

1960Year Built

6,691 sq ftLot Size

$556Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Matt Montgomery Group • Compass

Bought with Allison Blank • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #72986616

Redfin Estimate

$1,195,545

$254K since sold in August 2022$291K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.1% lower than the average sale price ($1.39M) of 6 comparable homes.

SOLD AUG 7, 2026
$1,107,500
A
3 beds1.5 baths2,140 sq ft
231 Moss Hill Rd, Jamaica Plain, MA 02130
SOLD AUG 14, 2026
$1,459,450
B
3 beds2.5 baths2,576 sq ft
63 Mossdale Rd, Jamaica Plain, MA 02130
SOLD JUL 22, 2026
$1,710,000
C
3 beds2.5 baths2,188 sq ft
299 Pond St, Jamaica Plain, MA 02130
SOLD JAN 28, 2026
$1,700,000
D
4 beds2 baths1,920 sq ft
675 Chestnut Hill Ave, Brookline, MA 02445
SOLD JUL 13, 2026
$1,460,000
E
5 beds2 baths2,894 sq ft
34 Roseway St, Jamaica Plain, MA 02130
SOLD MAR 4, 2026
$910,000
F
5 beds2.5 baths1,943 sq ft
11 Round Hill St, Jamaica Plain, MA 02130

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Earn from this home

Sell

$64,294

Est. take-home

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Market trends in 02445, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

0.1% MoM

Median sale price

$1.2M

$85K MoM

Avg. days on market

30d

9 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN TODAY, 12PM TO 1:30PM
$998,000
2 beds2 baths1,218 sq ft
1731 Beacon St #402, Brookline, MA 02445
OPEN TODAY, 11AM TO 12:30PM
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
OPEN TODAY, 11AM TO 12PM
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway Rd, Brookline, MA 02445
EARLY ACCESS
Unknown
5 beds6 baths3,539 sq ft
291 Tappan St, Brookline, MA 02445
OPEN TODAY, 11AM TO 12:30PM
$1,495,000
3 beds2 baths1,759 sq ft
12 Kilsyth Rd #3, Brookline, MA 02445
$560,000
1 bed1 bath860 sq ft
77 Pond Ave #509, Brookline, MA 02445
$2,999,000
4 beds3.5 baths3,265 sq ft
52 Clinton Rd, Brookline, MA 02445
3D WALKTHROUGH
$6,495,000
9 beds7.5 baths8,619 sq ft
372 Warren St, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 29-31 Highland Rd

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

—

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Multi-Family (2-4 Unit)

County

Norfolk County

APN

40496

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 25, 2025.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 2
AttachedGarageYN: Yes
Parking Features: Paved Drive

Interior

Bedroom #5 Information
Length: 10

Bathroom Information
# of Bathrooms (Full): 2

Kitchen Information
Area: 110
Length: 10
Width: 11
Level: First
Features: Flooring - Hardwood,Countertops - Stone/Granite/Solid

Basement Information
Basement: Full

Interior Features
# of Rooms (Total): 15
Interior Features: Laundry Room

Unit #1 Information
# of Levels: 1
# of Floors: 1
Lease: N

Unit #2 Information
# of Levels: 1
# of Floors: 2
Lease: N

Exterior

Building Information
Building Area (Total): 2,152
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Stories (Total): 3
Year Built Source: Public Records
Year Built Details: Actual
Lead Paint: Certified Treated

Exterior Features
Roof: Shingle

Property Information
PropertySubType: Multi Family

Lot Information
Lot Size (Acres): 0.15
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $2,684.09
Tax Year: 2022

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Central
Heating Units: 2
Cooling: Window Unit(s)

Location

Location Information
Directions: Directions via Google
UnparsedAddress: 29-31 Highland Road, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Highway Access, House of Worship, Public School, T-Station, University

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Multi-Family (2-4 Unit)
Year Built: —
Year Renovated: —
County: Norfolk County
APN: 40496

Home facts updated by county records on Jul 25, 2025

Other

Miscellaneous Information
Heat Zones: 2

Listing Information
StandardStatus: Closed

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.6mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.8mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
2 months ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
152 deals
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Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

60% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Brookline, MA • 02445

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.14M – $1.38M

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Nearby similar homes

$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway Rd, Brookline, MA 02445

$775,000

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3D WALKTHROUGH

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New listings for sale in 02445

OPEN TODAY, 12PM TO 1:30PM

$998,000

2 beds2 baths1,218 sq ft

1731 Beacon St #402, Brookline, MA 02445

OPEN TODAY, 11AM TO 12:30PM

$859,000

3 beds1.5 baths1,233 sq ft

124 Chestnut St #1, Brookline, MA 02445

OPEN TODAY, 11AM TO 12PM

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$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway Rd, Brookline, MA 02445

EARLY ACCESSCOMPASS COMING SOON

Unknown

5 beds6 baths3,539 sq ft

291 Tappan St, Brookline, MA 02445

OPEN TODAY, 11AM TO 12:30PM

$1,495,000

3 beds2 baths1,759 sq ft

12 Kilsyth Rd #3, Brookline, MA 02445

$560,000

1 bed1 bath860 sq ft

77 Pond Ave #509, Brookline, MA 02445

$2,999,000

4 beds3.5 baths3,265 sq ft

52 Clinton Rd, Brookline, MA 02445

3D WALKTHROUGH

$6,495,000

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Home values near 29-31 Highland Rd

Data from public records.

Address	Redfin Estimate
29 Highland Road, Brookline, MA 4 Beds \| 2 Baths \| 2152 Sq. Ft.	$1,517,013
45 Highland Road, Brookline, MA 3 Beds \| 1 Baths \| 911 Sq. Ft.	$720,949

Address	Redfin Estimate
35 Highland Road, Brookline, MA 6 Beds \| 2 Baths \| 2152 Sq. Ft.	$1,327,637
47 Highland Road, Brookline, MA 3 Beds \| 1 Baths \| 950 Sq. Ft.	$723,510

Address	Redfin Estimate
41 Highland Road, Brookline, MA 4 Beds \| 3 Baths \| 2152 Sq. Ft.	$1,540,574
49 Highland Road, Brookline, MA 3 Beds \| 1 Baths \| 1009 Sq. Ft.	$909,782

Property information provided by MLS PIN when last listed in 2022. This data may not match . Learn more.

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