8 Upland Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

$1,041,800

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,538 sqft

8 Upland Rd, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $6,500/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.04M
Since last month
Increased$900 (+0.1%)
Since last year
Decreased$59K (-5.5%)
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 decreased by -8% in the last 10 years
MonthEstimated value
2026
September 2026$1.02M
August 2026$1.04M
July 2026$1.02M
June 2026$1.07M
May 2026$1.07M
April 2026$1.08M
March 2026$1.01M
February 2026$1.01M
January 2026$1.03M
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
11 Cameron St #1, Brookline, MA
0.27
Condo
$1,149,000
09/30/25
2
2
1,338
59 Auburn St #2, Brookline, MA
0.58
Condo
$1,700,000
04/30/26
3
2.5
1,529
147 Kent St #1, Brookline, MA
0.49
Condo
$2,640,000
10/15/25
3
3
1,997
3 Upland Rd #2, Brookline, MA
0.03
Condo
$1,090,000
05/04/26
3
2
1,655
24 Evergreen St #2, Jamaica Plain, MA
0.64
Condo
$1,072,000
01/16/26
3
2
1,747
14 Castleton St #1, Jamaica Plain, MA
0.60
Condo
$1,139,000
05/05/26
2
2.5
1,961
148 Kent St, Brookline, MA
0.48
Condo
$2,200,000
08/03/26
4
3.5
2,375
69 Walnut St #4, Brookline, MA
0.07
Condo
$2,850,000
07/21/26
4
4
2,510
70 Day St #3, Boston, MA
0.71
Condo
$1,100,000
04/30/26
4
2
2,093
255 Walnut St #B, Brookline, MA
0.29
Condo
$1,310,000
06/29/26
3
1.5
1,543

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
115 Walnut St #3, Brookline, MA 02445
0.03
$1,793,400
4
2
2,185
Off Market
48 Boylston St, Jamaica Plain, MA 02130
0.05
-
6
6
4,992
Off Market
96 Walnut St, Brookline, MA 02445
0.03
$1,890,300
4
2
2,288
Off Market
88 Walnut St #3, Brookline, MA 02445
0.04
$837,200
2
1
975
Off Market
88 Walnut St #1, Brookline, MA 02445
0.04
$1,015,400
2
2
1,365
Off Market
129 Walnut St, Brookline, MA 02445
0.03
$1,689,800
6
2.5
3,784
Off Market
82 Walnut St #1, Brookline, MA 02445
0.05
$680,200
2
1
970
Off Market
72 Walnut St #1, Brookline, MA 02445
0.06
$1,418,300
3
2.5
1,600
Off Market
69 Walnut St #15, Brookline, MA 02445
0.07
$1,594,900
3
2
1,395
Off Market
69 Walnut St #14, Brookline, MA 02445
0.07
$1,786,400
3
3
1,535
Off Market
20 Boylston St #2, Jamaica Plain, MA 02130
0.07
-
3
2
1,521
Off Market
69 Walnut St #10A, Brookline, MA 02445
0.07
-
2
2
1,175
Off Market

Local Information

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

Home Highlights

Condo
1,538 sqft
$677/sqft

About this House

This condo is located at 8 Upland Rd, Brookline, MA. 8 Upland Rd is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 3 bedrooms, 3 bathrooms and approximately 1,538 sqft of floor space. This property has a lot size of 4005 sqft.
8 Upland Rd, Brookline, MA 02445 is a 3 bedroom, 3 bathroom, 1,538 sqft condo in High Street Hill. More recently, it was listed as a rental in June 2014 with an asking price of $4,500 per month. That rental listing was removed on June 24, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,041,800, with a rent estimate of $5,718/month.

Home Details for 8 Upland Rd

Interior Features

Interior Details
BasementAdditional StorageTypes of Rooms: Walk In Closet, Dining Room, Master Bath, OfficeStorage
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Condo

Exterior Features

Exterior Home Features
DeckExterior: ShingleLawnPatioPorch
Parking & Garage
Parking: Off Street

Lot Information

Lot Area: 4005 sqft

Price and Tax history

DateEventPrice
Jun 24, 2014
Source: Agent Provided
ListingRemoved
$4,500
Jun 9, 2014
Source: Agent Provided
Listed For Rent
$4,500
Sep 14, 2008
Source: Agent Provided
ListingRemoved
$669,000
Jul 25, 2008
Source: Agent Provided
Listed For Sale
$669,000

Market trends in Brookline

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.24M
$23.33KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$811
$6MoM
Available listings
186
30MoM

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

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 8 Upland Rd

  • What is 8 Upland Rd estimated to be worth?
    Trulia's estimated value for 8 Upland Rd in Brookline, MA is $1,041,800.
  • 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 $1.24M. That is up $23.33K from the prior month.
  • What do residents say about the High Street Hill neighborhood?
    Residents describe the High Street Hill neighborhood in Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in High Street Hill, Brookline.
  • Does 8 Upland Rd have air conditioning?
    Yes, 8 Upland Rd in Brookline, MA has air conditioning.
  • Does 8 Upland Rd have parking?
    Yes, 8 Upland Rd in Brookline, MA has on-site parking.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

459 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

46 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

701 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

17 rentals with an outdoor space in Brookline, MA

Apartments for Rent

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Off Market Homes Near 8 Upland Rd

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Homes for sale near 8 Upland Rd

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