56 Upland Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

56 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 5 Baths
  • 3,938 sqft

$4,023,400

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $23,523/mo*
Refinance Your Home

$4,023,400

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $23,523/mo*
Refinance Your Home
6 Beds
5 Baths
3,938 sqft

Local Information

  • Map ViewExplore the area around 56 Upland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Spectacular 1890's Shingle-style home on the Philbrick Green in historic Pill Hill.Beautifully maintained and thoughtfully improved home offers 11 generously proportioned rooms filled with light and distinctive architectural detail perfect for grand entertaining and comfortable family living. A welcoming porch invites you to a gracious entry hall and elegant living room.2011 stunning kitchen and mudroom remodel, banquet-size dining room with French doors to large deck with pergola and lush private gardens.Stunning stair tower leads to second and third floor comprising a luxurious master suite, large playroom,4 family bedrooms and an office.Many recent and substantial upgrades include 2008 exterior shingles and roof improvement including lead coated copper valleys,2006 multi-zone hydro air heating and air conditioning and bathroom additions,perimeter French drain.This wonderful home in Lincoln School district is close to Brookline Village,Longwood Medical area and public transportation.
56 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 5 bathroom, 3,938 sqft single-family home in High Street Hill, built in 1890. It last sold for $2,450,000 on Jul 30, 2014. It is currently off market. The Trulia Estimate is $4,023,400, with a rent estimate of $8,300/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 56 Upland Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 10
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1890Year Updated: 1981
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 7840 sqft

Price History for 56 Upland Rd

DatePriceEventSource
07/30/2014$2,450,000Sold
N/A
05/29/2014$2,450,000PriceChange
Agent Provided
05/05/2014$2,595,000Listed For SaleAgent Provided
08/12/2005$2,100,000Sold
N/A
01/10/1989$600,000Sold
N/A

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$32,796
Assessment$3,322,800
Home facts updated by county records

Comparable Sales for 56 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.10
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.13
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
209 High St, Brookline, MA
0.27
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
12 Zamora St, Boston, MA
0.56
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
157 Aspinwall Ave, Brookline, MA
0.58
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
7 Dana St, Brookline, MA
0.41
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
27 Walnut Pl, Brookline, MA
0.15
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
157 Aspinwall Ave, Brookline, MA
0.57
Single-Family Home
$2,800,000
09/22/25
4
4
3,515
50 Waverly St, Brookline, MA
0.36
Single-Family Home
$2,445,000
05/12/26
4
2
2,383

Nearby homes

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Assigned Schools

These are the assigned schools for 56 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

368 pet-friendly rentals in Brookline, MA

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Explore by feature - Air Conditioning

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Explore by feature - Outdoor Space

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Homes for sale near 56 Upland Rd

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Off Market Homes Near 56 Upland Rd

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