28 Upland Rd, Brookline, MA 02445
OFF MARKET

28 Upland Rd
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 3 Baths
  • 1,772 sqft

$1,809,300

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $10,800/mo*
Refinance Your Home

$1,809,300

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $10,800/mo*
Refinance Your Home
3 Beds
3 Baths
1,772 sqft

Local Information

Map showing home location
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Commute Destination

Description

This single-family home is located at 28 Upland Rd, Brookline, MA. 28 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 1,772 sqft of floor space. This property has a lot size of 3920 sqft and was built in 1926.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 28 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1926Year Updated: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 3920 sqft

Price History for 28 Upland Rd

DatePriceEventSource
06/03/1988$241,500Sold
N/A
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Property Tax and Assessment

Year2025
Tax$15,513
Assessment$1,571,700
Home facts updated by county records

Comparable Sales for 28 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Highland Rd, Brookline, MA
0.26
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
129 Walnut St, Brookline, MA
0.08
Single-Family Home
$1,150,000
06/04/25
6
2.5
3,784
20-20 Linden Pl #R, Brookline, MA
0.39
Single-Family Home
$1,925,000
08/28/25
3
3.5
2,028
209 High St, Brookline, MA
0.35
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
236 Walnut St, Brookline, MA
0.25
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
50 Waverly St, Brookline, MA
0.33
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
23 Toxteth St, Brookline, MA
0.44
Single-Family Home
$2,201,000
06/23/25
4
2.5
2,634
19 Sunnyside St, Jamaica Plain, MA
0.75
Single-Family Home
$1,231,000
05/22/25
5
2.5
1,664
7 Dana St, Brookline, MA
0.40
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315

Assigned Schools

These are the assigned schools for 28 Upland Rd.
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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

Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 28 Upland Rd

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Homes for rent near 28 Upland Rd

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Off Market Homes Near 28 Upland Rd

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Explore by feature

28 Upland Rd, Brookline, MA 02445 is a 3 bedroom, 3 bathroom, 1,772 sqft single-family home built in 1926. 28 Upland Rd is located in High Street Hill, Brookline. This property is not currently available for sale. 28 Upland Rd was last sold on Jun 3, 1988 for $241,500. The current Trulia Estimate for 28 Upland Rd is $1,809,300.