57 Upland Rd, Brookline, MA 02445
OFF MARKET

57 Upland Rd
Brookline, MA 02445

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

$5,488,700

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $32,609/mo*
Refinance Your Home

$5,488,700

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $32,609/mo*
Refinance Your Home
6 Beds
6 Baths
6,775 sqft

Local Information

Map showing home location
© Google
-- 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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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
Skip to last item
  • Results are loading
Skip to first item

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
27 Irving St, Brookline, MA
0.04
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
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
19 Edgehill Rd, Brookline, MA
0.15
Single-Family Home
$3,765,000
05/28/25
5
4
3,538
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
212 Aspinwall Ave, Brookline, MA
0.58
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
115 Clark Rd, Brookline, MA
0.66
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182

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

Skip to last item
Skip to first item

Homes for sale near 57 Upland Rd

Skip to last item
Skip to first item

Homes for rent near 57 Upland Rd

Skip to last item
Skip to first item

Off Market Homes Near 57 Upland Rd

Skip to last item
Skip to first item

Explore by feature

57 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 6 bathroom, 6,775 sqft single-family home built in 1893. 57 Upland Rd is located in High Street Hill, Brookline. This property is not currently available for sale. 57 Upland Rd was last sold on Dec 17, 2009 for $2,800,000. The current Trulia Estimate for 57 Upland Rd is $5,488,700.