OFF MARKET

Off Market Apr 2023 for $1.5M

$1,433,781

•

2,152

sq ft

35-37 Highland Rd, Brookline, MA 02445

About this home

Wonderfully located on Pill Hill, this lovely two-family residence is within proximity to Brookline Village & Jamaica Pond. Each unit has a private entrance & features three nice sized bedrooms with spacious closets, a full bathroom, an attached garage, additional outside parking, & private outdoor space. The main living area is highlighted by a flexible, open layout for everyday living & entertaining. Beautiful sunlight filters in through picture windows that frame views of Downes Field. The kitchen opens into the dining area appointed with a peninsula with a cooktop & additional cabinetry. The basement offers laundry facilities, separate systems, & a two-car garage with extra storage space. Improvements: 2023 interior painted, bathrooms~tiles & tubs porcelain glazed, 2021 exterior painted, driveway repaved, chimney re-pointed. This property presents an excellent opportunity for investors & end-users alike. Easy access to the D-Line, Longwood Medical Area, bike trails & Olmsted Park.

Multi-familyProperty Type

1960Year Built

7,283 sq ftLot Size

$666Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Concierge Home Sales By the Kerzner Group • Hammond Residential Real Estate

Bought with Victoria Tran Slomiak • Lineage Realty Group

Redfin checked: 3 minutes ago

•Source:MLS PIN #73089650

Redfin Estimate

$1,433,781

$106K since sold in April 2023$194K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.3% lower than the average sale price ($1.60M) 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 JUL 13, 2026
$1,460,000
D
5 beds2 baths2,894 sq ft
34 Roseway St, Jamaica Plain, MA 02130
SOLD JAN 28, 2026
$1,700,000
E
4 beds2 baths1,920 sq ft
675 Chestnut Hill Ave, Brookline, MA 02445
SOLD MAY 15, 2026
$2,150,000
F
5 beds3.5 baths2,616 sq ft
25A Eliot St, Jamaica Plain, MA 02130

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Earn from this home

Sell

$206,723

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

$998,000
2 beds2 baths1,218 sq ft
1731 Beacon St #402, Brookline, MA 02445
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
$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
$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 35-37 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

B:299 L:0005 S:0001,40497

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: 6
Parking Features: Paved Drive, Off Street, Driveway

Interior

Bathroom Information
# of Bathrooms (Full): 2

Basement Information
Basement: Full, Walk-Out Access, Garage Access

Laundry Information
Laundry Features: Washer Hookup

Interior Features
# of Rooms (Total): 12
Flooring: Hardwood
Interior Features: Laundry Room

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

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

Exterior

Building Information
Building Area (Total): 2,152
Foundation Details: Concrete Perimeter
Construction Materials: Frame, Stone
Stories (Total): 2
Year Built Source: Public Records
Year Built Details: Approximate
Color: Gray

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck - Wood, Patio
Exterior Features: Garden

Property Information
PropertySubType: Multi Family

Lot Information
Lot Size (Acres): 0.17
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $14,052
Tax Year: 2023

Utilities

Utility Information
Utilities: for Electric Range, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: Fuses

Heating & Cooling
Has Heating
Heating: Baseboard, Oil
Heating Units: 2

Location

Location Information
Directions: High St to Highland Rd
UnparsedAddress: 35-37 Highland Rd, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Highway Access, Private School, 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: B:299 L:0005 S:0001,40497

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

6/10 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

$1.36M – $1.65M

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Nearby similar homes

$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway Rd, Brookline, MA 02445

$775,000

5 beds3 baths3,159 sq ft

31 Lawrence Ave, Dorchester, MA 02121

$1,549,000

9 beds3 baths3,144 sq ft

177 Chestnut Ave, Jamaica Plain, MA 02130

$5,500,000

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97-103 University Rd, Brookline, MA 02445

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9 beds3 baths4,986 sq ft

22-A Crawford St, Dorchester, MA 02121

3D WALKTHROUGH

$3,250,000

9 beds3 baths4,845 sq ft

52 Paul Gore St, Jamaica Plain, MA 02130

New listings for sale in 02445

$998,000

2 beds2 baths1,218 sq ft

1731 Beacon St #402, Brookline, MA 02445

$859,000

3 beds1.5 baths1,233 sq ft

124 Chestnut St #1, Brookline, MA 02445

$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 ACCESSCOMPASS COMING SOON

Unknown

5 beds6 baths3,539 sq ft

291 Tappan St, Brookline, MA 02445

$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

Home values near 35-37 Highland Rd

Data from public records.

Address	Redfin Estimate
29 Highland Road, Brookline, MA 4 Beds \| 2 Baths \| 2152 Sq. Ft.	$1,517,013
53 Highland Road, Brookline, MA 6 Beds \| 2 Baths \| 2212 Sq. Ft.	$1,532,925

Address	Redfin Estimate
35 Highland Road, Brookline, MA 6 Beds \| 2 Baths \| 2152 Sq. Ft.	$1,327,637
45 Highland Road, Brookline, MA 3 Beds \| 1 Baths \| 911 Sq. Ft.	$720,949

Address	Redfin Estimate
41 Highland Road, Brookline, MA 4 Beds \| 3 Baths \| 2152 Sq. Ft.	$1,540,574
47 Highland Road, Brookline, MA 3 Beds \| 1 Baths \| 950 Sq. Ft.	$723,510

Property information provided by MLS PIN when last listed in 2023. This data may not match . Learn more.

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