57 Upland Rd, Brookline, MA 02445
OFF MARKET

$5,517,400

Trulia Estimate
  • 6 Beds
  • 6 Baths
  • 6,775 sqft

57 Upland Rd, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $34,876/mo*
Refinance Your Home
Currently Off Market - Sold Dec 17, 2009 for $2,800,000

Home Value

Trulia Estimate
$5.52M
Since last month
Increased$54K (+1%)
Since last year
Increased$148K (+2.8%)
Since last sale
Increased$3M (+97%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
October 2026$5.52M
October 2026$5.52M
September 2026$5.46M
August 2026$5.54M
July 2026$5.64M
June 2026$5.65M
May 2026$5.66M
April 2026$5.66M
March 2026$5.58M
February 2026$5.46M
January 2026$5.3M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
36 Allerton St, Brookline, MA
0.15
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
16 Kennard Rd, Brookline, MA
0.41
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
54 Clark Rd, Brookline, MA
0.52
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
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
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
221 Gardner Rd, Brookline, MA
0.74
Single-Family Home
$4,625,000
10/23/26
5
5.5
4,324
213 Gardner Rd, Brookline, MA
0.74
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
209 High St, Brookline, MA
0.29
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
51 Upland Rd, Brookline, MA 02445
0.02
$3,389,100
6
4
4,052
Off Market
65 Upland Rd, Brookline, MA 02445
0.02
$3,483,300
6
4
4,101
Off Market
18 Maple St, Brookline, MA 02445
0.02
$2,496,500
5
4
3,786
Off Market
12 Maple St, Brookline, MA 02445
0.03
$4,195,100
6
4.5
4,827
Off Market
71 Upland Rd, Brookline, MA 02445
0.03
$2,145,400
4
3
1,696
Off Market
43 Upland Rd, Brookline, MA 02445
0.03
$3,575,500
6
4
3,890
Off Market
52 Upland Rd, Brookline, MA 02445
0.03
$3,286,300
8
4
4,651
Off Market
107 Upland Rd, Brookline, MA 02445
0.03
$3,746,300
5
4
4,746
Off Market
56 Upland Rd, Brookline, MA 02445
0.04
$3,910,900
6
5
3,938
Off Market
62 Upland Rd, Brookline, MA 02445
0.04
$3,502,800
5
4
3,604
Off Market
27 Irving St, Brookline, MA 02445
0.04
$3,365,000
7
4
5,244
Off Market
39 Irving St, Brookline, MA 02445
0.04
$5,157,200
5
5
4,959
Off Market
70 Upland Rd, Brookline, MA 02445
0.05
$3,863,700
5
6
5,312
Off Market
44 Irving St #3, Brookline, MA 02445
0.05
-
3
1
1,200
Off Market
60 Irving St #2, Brookline, MA 02445
0.06
-
-
-
-
Off Market
100 Upland Rd, Brookline, MA 02445
0.06
$5,279,100
6
4
5,940
Off Market
5 Maple St, Brookline, MA 02445
0.06
$4,384,300
9
5
7,252
Off Market
94 Upland Rd, Brookline, MA 02445
0.06
$3,082,700
8
4
4,719
Off Market
30 Irving St, Brookline, MA 02445
0.06
$2,528,300
4
3
2,547
Off Market
55 Irving St, Brookline, MA 02445
0.06
$4,427,700
8
7.5
5,483
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1893
6,775 sqft
$814/sqft

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,517,400.

Home Details for 57 Upland Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
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 and Tax history

DateEventPrice
Dec 17, 2009
Source: N/A
Sold
$2,800,000
Jun 26, 2008
Source: N/A
Sold
$1,462,500
Apr 25, 2008
Source: Agent Provided
Listed For Sale
$1,695,000

Market trends in Brookline

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.19M
$50.67KMoM
Sale-to-List Price
98.7%
0.6%MoM
Price per sq ft
$806
$3MoM
Available listings
227
39MoM
Sourced by Trulia Market Trends

Around this home

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

Frequently asked questions about 57 Upland Rd

  • What is 57 Upland Rd estimated to be worth?
    Trulia's estimated value for 57 Upland Rd in Brookline, MA is $5,517,400.
  • What is the price history for 57 Upland Rd?
    57 Upland Rd in Brookline, MA last sold for $2,800,000 in December 2009.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.19M. That is down $50.67K from the prior month.
  • How big is the lot at 57 Upland Rd?
    The lot at 57 Upland Rd in Brookline, MA is about 0.23 acres (9,954 sq ft).

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Apartments for Rent

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