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

8 Upland Rd #2
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 3 Baths
  • 1,702 sqft

$1,400,900

Trulia Estimate
as of Jul 8, 2026

$1,400,900

Trulia Estimate
as of Jul 8, 2026
3 Beds
3 Baths
1,702 sqft

Local Information

  • Map ViewExplore the area around 8 Upland Rd #2.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

2008 CONVERSION OF A 2 FAMILY HOME. GUT REHAB DUPLEX CONDO WITH STATE-OF-THE-ART KITCHEN & BATHS. 3 BEDROOMS,2.5 BATHS & OPEN LIVING ROOM & DINING ROOM AREA. SPECTACULAR LOFT MASTER BEDROOM WITH BATH. FEATURES INCLUDE ALL HIGH END FINISHES. CROWN MOLDING,HARDWOOD FLOORS,AC,WASHER/DRYER IN UNIT,CEDAR CLOSET/EXTRA STORAGE IN BASEMENT,PORCH & TANDEM PARKING.CONVENIENT TO BROOKLINE VILLAGE,PUBLIC TRANSPORTATION & LINCOLN SCHOOL.
8 Upland Rd #2, Brookline, MA 02445 is a 3 bedroom, 3 bathroom, 1,702 sqft condo in High Street Hill, built in 1925. It last sold for $660,000 on Aug 18, 2008. It is currently off market. The Trulia Estimate is $1,400,900, with a rent estimate of $5,428/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 8 Upland Rd #2

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1925
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 1

Price History for 8 Upland Rd #2

DatePriceEventSource
08/18/2008$660,000Sold
N/A

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$12,337
Assessment$1,249,900
Home facts updated by county records

Comparable Sales for 8 Upland Rd #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Upland Rd #2, Brookline, MA
0.03
Condo
$1,090,000
05/04/26
3
2
1,655
48 Kent St #1, Brookline, MA
0.25
Condo
$1,100,000
08/27/25
3
3
1,629
33 Pond Ave #1208, Brookline, MA
0.20
Condo
$970,000
09/15/25
2
2.5
1,840
33 Pond Ave #Penthouse 1207, Brookline, MA
0.24
Condo
$880,000
10/15/25
2
2.5
1,800
33 Pond Ave #Penthouse 1208, Brookline, MA
0.24
Condo
$970,000
09/15/25
2
2.5
1,840
99 Pond Ave, Brookline, MA
0.18
Condo
$900,000
08/08/25
2
2
1,855
99 Pond Ave #804, Brookline, MA
0.19
Condo
$900,000
08/08/25
2
2
1,855
99 Pond Ave #220, Brookline, MA
0.20
Condo
$745,000
08/27/25
2
2
1,300
77 Pond Ave #1506, Brookline, MA
0.19
Condo
$790,000
03/31/26
2
2
1,260
81 Glen Rd #S1, Brookline, MA
0.30
Condo
$1,025,000
07/14/25
2
2.5
1,492

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Upland Rd #2.
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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Homes for sale near 8 Upland Rd #2

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Off Market Homes Near 8 Upland Rd #2

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