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

100 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 4 Baths
  • 5,940 sqft (on 0.25 acres)

$5,406,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $31,585/mo*
Refinance Your Home

$5,406,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $31,585/mo*
Refinance Your Home
6 Beds
4 Baths
5,940 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 100 Upland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Situated near Philbrick Square, this stately brick Colonial Revival-style house was designed by Peabody and Stearns in1889. Thoughtfully renovated, it offers updated five-zone hydro-air HVAC and a newer open kitchen with granite counters and stainless steel appliances. A wood paneled foyer with beautiful fireplace leads to an elegant, sun-filled living room and to a cozy front parlor with bay window with window seats. The 19'x16' dining room, separated by pocket doors from the 21'x19' living room, has a door that opens to a well landscaped fenced yard and stone patio. On the second floor, there is a master wing that includes bedroom, sitting area with fireplace, marble bathroom, office and closets. Additional rooms used as bedroom, exercise room, playroom and study with custom built shelves are on the third floor Queen Anne-style architectural details are found throughout the house in its oriel, oval and arched windows. Brookline Village and Lincoln School are close by.
100 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 4 bathroom, 5,940 sqft single-family home in High Street Hill, built in 1889. It last sold for $3,100,000 on Jul 30, 2014. It is currently off market. The Trulia Estimate is $5,406,700, with a rent estimate of $8,159/month.

Home Highlights

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

Home Details for 100 Upland Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 14
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick

Property Information

Year Built
Year Built: 1889Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 100 Upland Rd

DatePriceEventSource
07/30/2014$3,100,000Sold
N/A
04/22/2014$3,100,000ListingRemovedAgent Provided
04/03/2014$3,100,000PendingAgent Provided
04/01/2014$3,100,000Listed For SaleAgent Provided

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$48,924
Assessment$4,956,800
Home facts updated by county records

Comparable Sales for 100 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.13
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
236 Walnut St, Brookline, MA
0.12
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
27 Walnut Pl, Brookline, MA
0.07
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
12 Zamora St, Boston, MA
0.61
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
7 Dana St, Brookline, MA
0.35
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
115 Clark Rd, Brookline, MA
0.61
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182
469 Walnut St, Brookline, MA
0.66
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
209 High St, Brookline, MA
0.25
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
213 Gardner Rd, Brookline, MA
0.71
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507

Nearby homes

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Assigned Schools

These are the assigned schools for 100 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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Explore by feature - Pet Friendly

368 pet-friendly rentals in Brookline, MA

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Explore by feature - Outdoor Space

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Homes for sale near 100 Upland Rd

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Off Market Homes Near 100 Upland Rd

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