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

4 Upland Rd #2
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 1 Bath
  • 1,054 sqft

$847,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $4,373/mo*

$847,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $4,373/mo*
3 Beds
1 Bath
1,054 sqft

Local Information

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

Description

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. It is currently off market. The Trulia Estimate is $847,800, with a rent estimate of $3,909/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4 Upland Rd #2

Interior Features

Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
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 History for 4 Upland Rd #2

DatePriceEventSource
12/03/2010$465,000ListingRemovedAgent Provided
10/20/2010$465,000Listed For SaleAgent Provided
08/27/2004$429,000Sold
N/A

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333
MoM
Sale-to-List Price
99.9%
0.9%
MoM
Price per sq ft
$814
$5
MoM
Available listings
238
11
MoM
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Property Tax and Assessment

Year2025
Tax$8,205
Assessment$831,300
Home facts updated by county records

Comparable Sales for 4 Upland Rd #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.18
Condo
$656,000
03/20/26
3
1
939
0.13
Condo
$760,000
07/11/25
3
1
892
0.13
Condo
$760,000
07/11/25
3
1
892
0.27
Condo
$740,000
04/28/26
3
1
987
0.27
Condo
$817,000
06/26/26
3
1
1,000
0.29
Condo
$740,000
05/14/26
3
1
978
0.15
Condo
$635,000
08/23/25
2
1
822
0.15
Condo
$650,000
09/02/25
2
1
822
0.22
Condo
$712,500
12/23/25
2
1
1,136
0.40
Condo
$430,000
11/18/25
2
1
1,125

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Upland Rd #2.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

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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Homes for sale near 4 Upland Rd #2

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Off Market Homes Near 4 Upland Rd #2

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