57 Upland Rd, Brookline, MA 02445
OFF MARKET

57 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 6 Baths
  • 6,775 sqft

$5,734,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $33,492/mo*
Refinance Your Home

$5,734,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $33,492/mo*
Refinance Your Home
6 Beds
6 Baths
6,775 sqft

Local Information

  • Map ViewExplore the area around 57 Upland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

2009 renovated masterpiece, overlooking Philbrick Green in the Pill Hill Historic District."Lincoln School". Great rooms for entertaining. Fabulous cooks kitchen opens to a family room with fireplace. Beautiful period details throughout.Central air conditioning.2-car garage. Enjoy the tree lined street while also being convenient to shops,restaurants and public transportation.
57 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 6 bathroom, 6,775 sqft single-family home in High Street Hill, built in 1893. It last sold for $2,800,000 on Dec 17, 2009. It is currently off market. The Trulia Estimate is $5,734,000, with a rent estimate of $7,319/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 57 Upland Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 14
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick

Property Information

Year Built
Year Built: 1893Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 9954 sqft

Price History for 57 Upland Rd

DatePriceEventSource
12/17/2009$2,800,000Sold
N/A
06/26/2008$1,462,500Sold
N/A
04/25/2008$1,695,000Listed For SaleAgent Provided

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$53,121
Assessment$5,382,100
Home facts updated by county records

Comparable Sales for 57 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.08
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.15
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
236 Walnut St, Brookline, MA
0.17
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.60
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
157 Aspinwall Ave, Brookline, MA
0.56
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
27 Walnut Pl, Brookline, MA
0.13
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
115 Clark Rd, Brookline, MA
0.66
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182
469 Walnut St, Brookline, MA
0.72
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
232 Kent St, Brookline, MA
0.78
Single-Family Home
$4,000,000
08/01/25
5
4.5
5,296
7 Dana St, Brookline, MA
0.37
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315

Nearby homes

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Assigned Schools

These are the assigned schools for 57 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

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Homes for sale near 57 Upland Rd

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Off Market Homes Near 57 Upland Rd

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