4 Upland Rd #2, Brookline, MA 02445
OFF MARKET

$819,600

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,054 sqft

4 Upland Rd #2, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $5,201/mo*
Refinance Your Home
Currently Off Market - Sold Aug 27, 2004 for $429,000

Home Value

Trulia Estimate
$820K
Since last month
Decreased$3K (-0.4%)
Since last year
Decreased$15K (-1.7%)
Since last sale
Increased$391K (+91%)
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 +21% in the last 10 years
MonthEstimated value
2026
October 2026$820K
September 2026$822K
August 2026$823K
July 2026$832K
June 2026$837K
May 2026$849K
April 2026$849K
March 2026$846K
February 2026$823K
January 2026$813K
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
98 Boylston St #2, Brookline, MA
0.04
Condo
$691,000
08/13/26
3
1
966
6 Juniper St #16, Brookline, MA
0.18
Condo
$656,000
03/20/26
3
1
939
38 Juniper St #108, Brookline, MA
0.15
Condo
$502,000
07/29/26
2
1
822
14 Linden St #8, Brookline, MA
0.27
Condo
$740,000
04/28/26
3
1
987
14 Linden St #7, Brookline, MA
0.27
Condo
$817,000
06/26/26
3
1
1,000
20 Rice St #2, Brookline, MA
0.29
Condo
$740,000
05/14/26
3
1
978
39 Kent St #B, Brookline, MA
0.22
Condo
$712,500
12/23/25
2
1
1,136
386 Riverway #4, Boston, MA
0.40
Condo
$430,000
11/18/25
2
1
1,125
47 Highland Rd #47, Brookline, MA
0.37
Condo
$815,000
11/26/25
3
1
981
14 Linden St #3, Brookline, MA
0.27
Condo
$765,000
05/04/26
2
1
975

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
4 Upland Rd #1, Brookline, MA 02445
0.00
$701,800
2
1
892
Off Market
129 Walnut St, Brookline, MA 02445
0.01
$1,670,100
6
2.5
3,784
Off Market
3 Upland Rd #1, Brookline, MA 02445
0.01
$1,103,100
4
2
1,655
Off Market
3 Upland Rd, Brookline, MA 02445
0.01
$1,155,500
3
2
1,655
Off Market
3 Upland Rd #3, Brookline, MA 02445
0.01
-
4
2
1,655
Off Market
3 Upland Rd #2, Brookline, MA 02445
0.02
$1,090,000
3
2
1,655
Recently Sold
129 Walnut St #1, Brookline, MA 02445
0.02
$1,999,900
3
2.5
2,272
For Sale
137 Walnut St #1, Brookline, MA 02445
0.02
$791,900
2
2
1,196
Off Market
137 Walnut St #2, Brookline, MA 02445
0.02
$581,700
2
1
1,021
Off Market
137 Walnut St #3T, Brookline, MA 02445
0.02
-
2
1
-
Off Market
123 Walnut St #2, Brookline, MA 02445
0.02
$1,623,100
3
3
2,216
Off Market
123 Walnut St #1, Brookline, MA 02445
0.02
$1,657,300
3
3
2,291
Off Market
8 Upland Rd #2, Brookline, MA 02445
0.02
$1,379,300
3
3
1,702
Off Market
8 Upland Rd #1, Brookline, MA 02445
0.02
$1,301,800
3
3
1,613
Off Market
8 Upland Rd, Brookline, MA 02445
0.02
$1,068,300
3
3
1,538
Off Market
148 Walnut St, Brookline, MA 02445
0.02
$2,269,000
9
4
4,002
Off Market
110 Walnut St, Brookline, MA 02445
0.02
$1,735,500
3
1
2,288
Off Market
110 Walnut St #U2, Brookline, MA 02445
0.02
-
3
1
-
Off Market
110 Walnut St #QT2, Brookline, MA 02445
0.02
-
3
1
-
Off Market
110 Walnut St #LR2, Brookline, MA 02445
0.02
-
3
1
-
Off Market

Local Information

  • Map ViewExplore the area around 4 Upland Rd #2.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1920
1,054 sqft
$778/sqft
Garage

About this House

Fab 2+ bed in lovely condition, located on great Pill Hill street.Charming & light filled, this home has a wonderful, flexible floor plan.Nicely sized living room opens to an entertainment sized formal dining room with nice detail.True cook's kitchen has a centre island w/ silestone, double sink, fabulous breakfast bar & an over sized pantry.Off the kitchen there is a large deck which overlooks the superb yard.2 big bedrooms with an additional room as 3rd bed or office. 2 tandem parking spaces.
4 Upland Rd #2, Brookline, MA 02445 is a 3 bedroom, 1 bathroom, 1,054 sqft condo in High Street Hill, built in 1920. It last sold for $429,000 on Aug 27, 2004. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $819,600, with a rent estimate of $3,832/month.

Home Details for 4 Upland Rd #2

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Dec 3, 2010
Source: Agent Provided
ListingRemoved
$465,000
Oct 20, 2010
Source: Agent Provided
Listed For Sale
$465,000
Aug 27, 2004
Source: N/A
Sold
$429,000

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

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

This October

Trick-or-Treat Score

Built from what locals say about High Street Hill.
  • 98% say there are sidewalks
  • 63% say there's holiday spirit
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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 4 Upland Rd #2

  • What is 4 Upland Rd #2 estimated to be worth?
    Trulia's estimated value for 4 Upland Rd #2 in Brookline, MA is $819,600.
  • What is the price history for 4 Upland Rd #2?
    4 Upland Rd #2 in Brookline, MA last sold for $429,000 in August 2004.
  • 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.

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Apartments for Rent

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Off Market Homes Near 4 Upland Rd #2

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