4 Upland Rd #1, Brookline, MA 02445
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Property image
OFF MARKET

4 Upland Rd #1
Brookline, MA 02445

High Street Hill
  • 2 Beds
  • 1 Bath
  • 892 sqft

$724,000

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $4,294/mo*
Refinance Your Home

$724,000

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $4,294/mo*
Refinance Your Home
2 Beds
1 Bath
892 sqft

Local Information

  • Map ViewExplore the area around 4 Upland Rd #1.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Exclusive Listing Agents: The Davidson & Giglio Team www/DavidsonBoston.com * richardgiglio@kw.com 617-861-3613 * 617-257-7179 * 617-861-3602 Charming two bedroom condo in established two-unit building ideally situated on tree-lined street in quiet Brookline neighborhood. This well laid out home consists of spacious living room, dining room and two nicely sized bedrooms. The generous kitchen was recently renovated. Gleaming hardwood floors throughout. Delightful private rear porch and landscaped back yard complete this serene setting. Abundant sunlight streams thru many windows. Extras include basement storage and shared driveway. New roof 2012. Conveniently located for quick access to Route 9. Green Line Brookline Village T stop minutes away. Stroll over to Brookline Village to take advantage of the many shops and restaurants. Coolidge Corner and Longwood medical area just a short distance away. Ideal home for first-time buyers.
4 Upland Rd #1, Brookline, MA 02445 is a 2 bedroom, 1 bathroom, 892 sqft condo in High Street Hill, built in 1920. It last sold for $522,000 on Aug 7, 2015. It is currently off market. The Trulia Estimate is $724,000, with a rent estimate of $3,330/month.

Home Highlights

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

Home Details for 4 Upland Rd #1

Interior Features

Interior Details
BasementNumber of Rooms: 5Types of Rooms: Dining Room, Family Room
Heating & Cooling
Heating: Radiant, GasHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodLawn
Parking & Garage
Parking: Off Street

Property Information

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

Community

Units in Building: 2

Price History for 4 Upland Rd #1

DatePriceEventSource
08/07/2015$522,000Sold
N/A
07/15/2015$499,000PendingAgent Provided
06/26/2015$499,000Listed For SaleAgent Provided
04/02/2013$419,000ListingRemovedAgent Provided
03/29/2013$419,000Listed For SaleAgent Provided
09/24/2007$389,000Sold
N/A
03/16/2001$312,000Sold
N/A

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
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Property Tax and Assessment

Year2025
Tax$7,008
Assessment$710,000
Home facts updated by county records

Comparable Sales for 4 Upland Rd #1

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Juniper St #97, Brookline, MA
0.15
Condo
$635,000
08/23/25
2
1
822
32 Juniper St #91, Brookline, MA
0.15
Condo
$650,000
09/02/25
2
1
822
6 Juniper St #16, Brookline, MA
0.18
Condo
$656,000
03/20/26
3
1
939
39 Kent St #B, Brookline, MA
0.22
Condo
$712,500
12/23/25
2
1
1,136
14 Linden St #3, Brookline, MA
0.27
Condo
$765,000
05/04/26
2
1
975
10 Jamaicaway #24, Boston, MA
0.36
Condo
$480,000
12/15/25
2
1
780
10 Jamaicaway #8, Boston, MA
0.36
Condo
$469,000
02/05/26
2
1
790
77 Pond Ave #1207, Brookline, MA
0.21
Condo
$505,000
10/10/25
1
1
860
60 Glen Rd #206, Brookline, MA
0.30
Condo
$815,000
10/30/25
2
1
916
6 Perry St, Brookline, MA
0.35
Condo
$710,000
10/15/25
2
1
890

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Upland Rd #1.
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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Explore by feature - Pet Friendly

355 pet-friendly rentals in Brookline, MA

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Homes for sale near 4 Upland Rd #1

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Off Market Homes Near 4 Upland Rd #1

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