52 Upland Rd, Brookline, MA 02445
OFF MARKET

52 Upland Rd
Brookline, MA 02445

High Street Hill
  • 8 Beds
  • 4 Baths
  • 4,651 sqft

$3,319,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $19,421/mo*
Refinance Your Home

$3,319,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $19,421/mo*
Refinance Your Home
8 Beds
4 Baths
4,651 sqft

Local Information

  • Map ViewExplore the area around 52 Upland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 52 Upland Rd, Brookline, MA. 52 Upland Rd is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 8 bedrooms, 4 bathrooms and approximately 4,651 sqft of floor space. This property has a lot size of 7405 sqft and was built in 1890.
52 Upland Rd, Brookline, MA 02445 is a 8 bedroom, 4 bathroom, 4,651 sqft single-family home in High Street Hill, built in 1890. It is currently off market. The Trulia Estimate is $3,319,500, with a rent estimate of $7,212/month.

Home Highlights

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

Home Details for 52 Upland Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 12
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1890Year Updated: 1976
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

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$30,892
Assessment$3,129,900
Home facts updated by county records

Comparable Sales for 52 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.09
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.12
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
236 Walnut St, Brookline, MA
0.20
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.57
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
209 High St, Brookline, MA
0.28
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
27 Walnut Pl, Brookline, MA
0.16
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
7 Dana St, Brookline, MA
0.40
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
157 Aspinwall Ave, Brookline, MA
0.57
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
157 Aspinwall Ave, Brookline, MA
0.56
Single-Family Home
$2,800,000
09/22/25
4
4
3,515
9 Greenough St, Brookline, MA
0.54
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104

Nearby homes

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Assigned Schools

These are the assigned schools for 52 Upland 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

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Explore by feature - Outdoor Space

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Homes for sale near 52 Upland Rd

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Off Market Homes Near 52 Upland Rd

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