Sold
Last Sold Price
6 beds2,152 sqft$716/sqft
35-37 Highland Rd, Brookline, MA 02445
Multi FamilyProperty Type
7,283 sq ftLot Size
1960Year Built
$716/sq ftPrice per sq ft
6 carsParking Spaces

Description

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...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.
Listing closed: 04/28/2023 12:00 AM • Source: MLS PIN, MLS#: 73089650

Recent comparable sales

Median sold price

$1,775,000

Avg days on market

19

Sale-to-list ratio

99.4%

Brookline, MA

9 comparable properties found

a front view of a house
1/36
1

$1,690,000

Sold 08/15/25

5
Bedrooms
2,310
Square Feet
0.10
Acres
a white house that has a small yard and large trees
1/16
2

$1,800,000

Sold 10/31/25

5
Bedrooms
2,252
Square Feet
0.09
Acres
$1,800,000 | 18-20 Cypress Street, Brookline, MA 02445
1/2
3

$1,800,000

Sold 06/13/25

5
Bedrooms
2,318
Square Feet
0.07
Acres
an aerial view of a house
1/41
4

$1,775,000

Sold 02/04/25

4
Bedrooms
2,288
Square Feet
0.09
Acres
a view of an empty room with wooden floor and a window
1/43
5

$1,550,000

Sold 09/01/25

6
Bedrooms
3,377
Square Feet
Unavailable
Acres
a front view of a house with garden
1/24
6

$1,700,000

Sold 01/28/26

4
Bedrooms
1,920
Square Feet
0.15
Acres
$2,200,000 | 126 Westbourne Terrace, Brookline, MA 02446
1/21
7

$2,200,000

Sold 06/10/26

6
Bedrooms
4,369
Square Feet
0.14
Acres
$1,505,000 | 33 Ackers Avenue, Unit 2, Brookline, MA 02445
1/26
8

$1,505,000

Sold 06/30/26

5
Bedrooms
2,549
Square Feet
Unavailable
Acres
$1,900,000 | 18 Milton Road, Brookline, MA 02445
1/23
9

$1,900,000

Sold 08/08/25

6
Bedrooms
3,895
Square Feet
0.16
Acres

Location

Sold By Lineage Realty Group, Victoria Tran

Add your commute

Payment Calculator

$8,999 per month

30 year fixed, 6.55% Interest

Principal and Interest

$7,828

Property Taxes

$1,171

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 35-37 Highland Road

Property Details
  • Taxes: $14,052 / year
  • MLS Type: Multi-family / 2 Family
  • Town: Brookline
  • Area: MA-Brookline
  • Style: Garden
  • Garage Spaces: 2
  • Parking Spaces Total: 6
Building Information
  • Stories: 3
  • Residences: 2
  • Year Built: 1960
  • Lot Size: 0.17 AC / 7,283 SF
General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Swimming Pool, Tennis Court, Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Highway Access, Private School, Public School, T-Station, University
  • Current Financing: Cash
  • Living Area: 2152.0
  • Color: Gray
  • SqFt with Basement: No
  • Total Units: 2
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Location/School
  • Grade School: Lincoln
  • High School: Brookline
  • Middle School: Lincoln
Features
Interior Features
  • Appliances: Oil Water Heater, Utility Connections for Electric Range
  • Basement Features: Full, Walk Out, Garage Access
  • Num of Baths: 2.0
  • Num of Full Baths: 2
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Integer: 2
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Hardwood
  • Laundry Features: Laundry Room, Washer Hookup
Exterior Features
  • Construction: Frame, Stone
  • Exterior Features: Garden
  • Exterior Features: Garden Area, Deck - Wood, Patio
  • Patio And Porch Features: Deck - Wood, Patio
  • Roof Material: Shingle
Parking Features
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Paved Drive, Off-Street, Improved Driveway
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off-Street, Improved Driveway
  • Parking Features: Off-Street, Improved Driveway
Utilities
  • Electric: Fuses
  • Heating: Unit 1(Hot Water Baseboard, Oil), Unit 2(Hot Water Baseboard
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Electric Range, Washer Hookup
  • Water: Public
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Disclosures: Offers,if any,will be reviewed at 2:00 on Monday. Roof & heating is older but well maintained,electrical panel uses Fuses,buyers should do their due diligence prior to submitting offers,ask agent regarding retaining wall
Tax Information
  • Tax ID: B:299 L:0005 S:0001,40497
  • Assessments: $1,447,900
  • Book: 10707
  • Tax Year: 2023
  • Zoning: T-5
Building / Association Information
Living Characteristics
  • Beds Total: 6
  • Total Living Levels: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Heat Units: 2
  • Heat Zones: 2
Complex & Association Information
  • Adult Community: No
Unit Information
Unit 1 Description
  • Floor U1: 1
  • Lease U1: N
  • Levels U1: 1
Unit 2 Description
  • Floor U2: 2
  • Lease U2: N
  • Levels U2: 0
Rental Info
Rental Info
  • Total Actual Rent: $.00
Market and Agent Information
Sale Info
  • Buyer Broker Comp: 2.5
  • Other Agent Compensation: 1.0

Property History for 35-37 Highland Road

DateEvent & SourcePriceAppreciation
Apr 28, 2023

Sold

MLS PIN #73089650

$1,540,000
Mar 27, 2023

Under Agreement

MLS PIN #73089650

Mar 27, 2023

Contingent

MLS PIN #73089650

DateEvent & SourcePrice
04/28/2023

Sold

MLS PIN #73089650

$1,540,000
03/27/2023

Under Agreement

MLS PIN #73089650

03/27/2023

Contingent

MLS PIN #73089650

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 35-37 Highland Road

Taxable ValueLand$1,026,800Additions$514,500Total$1,541,300
Tax Record2024$15,059 ($1,255 / month)
Home Facts
Baths2Total Finished SqFt2,152 SqFtAbove Grade Finished SqFt2,152 SqFtUnfinished Basement SqFt1,020 SqFtStories2Lot Size7,283 SqFtStyleDuplexYear Built1960Year Renovated1969ZoningT-5CountyNORFOLKAPNBROO B:299 L:0005 S:0001

Schools near 35-37 Highland Road

This home is within Brookline School District.
Rating
School
Type
Grades
Distance
Public - K to 8
Public - 9 to 12
Private - PK to 12
Private - 4 to 8
Rating
School
Distance
William H Lincoln School
PublicK to 8

Brookline High School
Public9 to 12

Maimonides School
PrivatePK to 12

Nativity Preparatory School
Private4 to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 02445

Contact Agent | Warren Street, Brookline, MA 02445
1/30
Compass Coming Soon

Contact Agent

5
Bedrooms
2,834
Square Feet
0.92
Acres
$859,000 | 124 Chestnut Street, Unit 1, Brookline, MA 02445
1/27
Listed By CompassOpen: 8/29 11:00AM - 12:30PM

$859,000

3
Bedrooms
1,233
Square Feet
$998,000 | 1731 Beacon Street, Unit 402, Brookline, MA 02445
1/24
Open: 8/30 12:00PM - 01:30PMNew

$998,000

2
Bedrooms
1,218
Square Feet
$2,895,000 | 71 Addington Road, Brookline, MA 02445
1/42
Listed By Coldwell Banker RealtyOpen: 8/28 12:30PM - 02:00PM

$2,895,000

7
Bedrooms
4,805
Square Feet
0.18
Acres
$2,200,000 | 26 Parkway Road, Brookline, MA 02445
1/42
Open: 8/29 12:00PM - 02:00PM

$2,200,000

9
Bedrooms
4,364
Square Feet
0.06
Acres
$2,895,000 | 71 Addington Road, Brookline, MA 02445
1/42
Listed By Coldwell Banker RealtyOpen: 8/28 12:30PM - 02:00PM

$2,895,000

7
Bedrooms
4,805
Square Feet
0.18
Acres
$4,800,000 | 221 Gardner Road, Brookline, MA 02445
1/20
Contingent

$4,800,000

5
Bedrooms
4,324
Square Feet
0.23
Acres
Contact Agent | 291 Tappan Street, Brookline, MA 02445
1/18
Compass Coming Soon

Contact Agent

5
Bedrooms
3,539
Square Feet
$1,495,000 | 12 Kilsyth Road, Unit 3, Brookline, MA 02445
1/23
Open: 8/30 11:00AM - 12:30PM

$1,495,000

3
Bedrooms
1,759
Square Feet

Nearby home values

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.