108 Upland Rd, Brookline, MA 02445
OFF MARKET

108 Upland Rd
Brookline, MA 02445

High Street Hill
  • 7 Beds
  • 5 Baths
  • 6,359 sqft (on 0.25 acres)

$4,509,700

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $26,806/mo*
Refinance Your Home

$4,509,700

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $26,806/mo*
Refinance Your Home
7 Beds
5 Baths
6,359 sqft
(on 0.25 acres)

Local Information

Map showing home location
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Description

This single-family home is located at 108 Upland Rd, Brookline, MA. 108 Upland Rd is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 7 bedrooms, 5 bathrooms and approximately 6,359 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1880.
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 & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 108 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1880Year Updated: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 108 Upland Rd

DatePriceEventSource
07/20/2004$2,500,000Sold
N/A
06/20/1991$625,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$40,315
Assessment$4,084,600
Home facts updated by county records

Comparable Sales for 108 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27 Irving St, Brookline, MA
0.09
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
14 Irving St, Brookline, MA
0.12
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.21
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
19 Edgehill Rd, Brookline, MA
0.18
Single-Family Home
$3,765,000
05/28/25
5
4
3,538
236 Walnut St, Brookline, MA
0.11
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.63
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
212 Aspinwall Ave, Brookline, MA
0.62
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
469 Walnut St, Brookline, MA
0.66
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
27 Walnut Pl, Brookline, MA
0.07
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
115 Clark Rd, Brookline, MA
0.60
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182

Assigned Schools

These are the assigned schools for 108 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

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 108 Upland Rd

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Off Market Homes Near 108 Upland Rd

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Homes for rent near 108 Upland Rd

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108 Upland Rd, Brookline, MA 02445 is a 7 bedroom, 5 bathroom, 6,359 sqft single-family home built in 1880. 108 Upland Rd is located in High Street Hill, Brookline. This property is not currently available for sale. 108 Upland Rd was last sold on Jul 20, 2004 for $2,500,000. The current Trulia Estimate for 108 Upland Rd is $4,509,700.