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

$5,294,900

Trulia Estimate
  • 6 Beds
  • 4 Baths
  • 5,940 sqft (on 0.25 acres)

100 Upland Rd, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $32,929/mo*
Refinance Your Home
Currently Off Market - Sold Jul 30, 2014 for $3,100,000

Home Value

Trulia Estimate
$5.29M
Since last month
Increased$87K (+1.7%)
Since last year
Increased$249K (+4.9%)
Since last sale
Increased$2M (+70.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +55% in the last 10 years
MonthEstimated value
2026
October 2026$5.29M
September 2026$5.21M
August 2026$5.26M
July 2026$5.4M
June 2026$5.39M
May 2026$5.4M
April 2026$5.41M
March 2026$5.35M
February 2026$5.17M
January 2026$5.01M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
12 Zamora St, Boston, MA
0.61
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
16 Kennard Rd, Brookline, MA
0.36
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
54 Clark Rd, Brookline, MA
0.48
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
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
71 Greenough St, Brookline, MA
0.48
Single-Family Home
$3,019,999
04/03/26
4
3
3,422

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
94 Upland Rd, Brookline, MA 02445
0.02
$3,062,100
8
4
4,719
Off Market
108 Upland Rd, Brookline, MA 02445
0.02
$4,558,200
7
5
6,359
Off Market
71 Upland Rd, Brookline, MA 02445
0.03
$2,145,400
4
3
1,696
Off Market
56 Walnut Pl, Brookline, MA 02445
0.03
$3,879,400
4
5
4,022
Off Market
107 Upland Rd, Brookline, MA 02445
0.03
$3,729,800
5
4
4,746
Off Market
84 Upland Rd, Brookline, MA 02445
0.04
$3,932,100
5
3.5
4,374
Off Market
Walnut Pl, Brookline, MA 02445
0.04
-
-
-
-
Off Market
65 Upland Rd, Brookline, MA 02445
0.04
$3,469,200
6
4
4,101
Off Market
35 Walnut Pl, Brookline, MA 02445
0.05
$7,128,100
7
6
5,549
Off Market
24 Walnut Pl, Brookline, MA 02445
0.05
$3,335,700
1
1
4,200
Off Market
57 Upland Rd, Brookline, MA 02445
0.06
$5,539,900
6
6
6,775
Off Market
18 Maple St, Brookline, MA 02445
0.06
$2,497,400
5
4
3,786
Off Market
78 Upland Rd, Brookline, MA 02445
0.07
$6,061,300
6
5.5
6,767
Off Market
70 Upland Rd, Brookline, MA 02445
0.07
$3,860,500
5
6
5,312
Off Market
9-17 Walnut Pl, Brookline, MA 02445
0.07
$4,677,600
4
3
3,486
Off Market
182 Walnut St, Brookline, MA 02445
0.07
$5,995,500
7
5
7,158
Off Market
51 Upland Rd, Brookline, MA 02445
0.07
$3,398,400
6
4
4,052
Off Market
27 Walnut Pl, Brookline, MA 02445
0.07
$4,146,900
4
3.5
4,232
Off Market
62 Upland Rd, Brookline, MA 02445
0.07
$3,502,800
5
4
3,604
Off Market
12 Maple St, Brookline, MA 02445
0.07
$4,214,400
6
4.5
4,827
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1889
0.25 acre lot
5,940 sqft
$891/sqft

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,294,900.

Home Details for 100 Upland Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
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 and Tax history

DateEventPrice
Jul 30, 2014
Source: N/A
Sold
$3,100,000
Apr 22, 2014
Source: Agent Provided
ListingRemoved
$3,100,000
Apr 3, 2014
Source: Agent Provided
Pending
$3,100,000
Apr 1, 2014
Source: Agent Provided
Listed For Sale
$3,100,000

Market trends in Brookline

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.19M
$50.67KMoM
Sale-to-List Price
98.7%
0.6%MoM
Price per sq ft
$806
$3MoM
Available listings
227
39MoM
Sourced by Trulia Market Trends

Around this home

Neighborhood Overview

High Street Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about High Street Hill

This October

Trick-or-Treat Score

Built from what locals say about High Street Hill.
  • 98% say there are sidewalks
  • 63% say there's holiday spirit
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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

Frequently asked questions about 100 Upland Rd

  • What is 100 Upland Rd estimated to be worth?
    Trulia's estimated value for 100 Upland Rd in Brookline, MA is $5,294,900.
  • What is the price history for 100 Upland Rd?
    100 Upland Rd in Brookline, MA last sold for $3,100,000 in July 2014.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.19M. That is down $50.67K from the prior month.
  • How big is the lot at 100 Upland Rd?
    The lot at 100 Upland Rd in Brookline, MA is about 0.25 acres (10,890 sq ft).

Explore by feature - Pet Friendly

230 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

59 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

427 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

35 homes with a pool in Brookline, MA

Explore by feature - Washer/dryer

712 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

16 rentals with an outdoor space in Brookline, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 100 Upland Rd

Skip to last item
Skip to first item

Homes for sale near 100 Upland Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item