24 Upland Rd, Brookline, MA 02445
OFF MARKET

24 Upland Rd
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 3 Baths
  • 1,887 sqft

$1,909,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $11,204/mo*
Refinance Your Home

$1,909,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $11,204/mo*
Refinance Your Home
3 Beds
3 Baths
1,887 sqft

Local Information

  • Map ViewExplore the area around 24 Upland Rd.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Charming 1920's Colonial sited at the top of Upland Road. Warm rich woods accent this welcoming foyer and entertaining rooms. Sunny living room opens to dining room with built-in china cabinet. A cozy very special enclosed porch with a sky light overloos the lovely level yard surrounded by mature plantings and and a grden with flowers and herbs. there are two bedrooms and two baths on the second floor plus a small office and a treehouse masterbedroom with skylights and a full bath on the third floor. Near transportation Longwood Medical and Brookline Village.
24 Upland Rd, Brookline, MA 02445 is a 3 bedroom, 3 bathroom, 1,887 sqft single-family home in High Street Hill, built in 1926. It last sold for $869,150 on Aug 25, 2010. It is currently off market. The Trulia Estimate is $1,909,700, with a rent estimate of $6,072/month.

Home Highlights

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

Home Details for 24 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1926Year Updated: 1972
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4021 sqft

Price History for 24 Upland Rd

DatePriceEventSource
08/25/2010$869,150Sold
N/A
06/05/2010$929,000Listed For SaleAgent Provided
07/20/2004$244,800Sold
N/A
09/16/1988$312,000Sold
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$15,433
Assessment$1,563,600
Home facts updated by county records

Comparable Sales for 24 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Highland Rd, Brookline, MA
0.27
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
18 Eldora St, Roxbury, MA
0.54
Single-Family Home
$863,000
10/10/25
4
1.5
2,149
14-14A Linden Pl, Brookline, MA
0.40
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
20-20 Linden Pl #R, Brookline, MA
0.38
Single-Family Home
$1,925,000
08/28/25
3
3.5
2,028
43 Waverly St, Brookline, MA
0.33
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676
209 High St, Brookline, MA
0.36
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
14 Irving St, Brookline, MA
0.06
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
50 Waverly St, Brookline, MA
0.33
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
236 Walnut St, Brookline, MA
0.25
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
26 Edge Hill St, Jamaica Plain, MA
0.69
Single-Family Home
$1,195,000
07/24/25
4
2.5
2,100

Nearby homes

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Assigned Schools

These are the assigned schools for 24 Upland Rd.
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 24 Upland Rd

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Off Market Homes Near 24 Upland Rd

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