111 High St, Brookline, MA 02445
Property image
Property image
OFF MARKET

$2,052,900

Trulia Estimate
  • 9 Beds
  • 5 Baths
  • 4,927 sqft

111 High St, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $12,746/mo*
Refinance Your Home
Currently Off Market - Sold May 22, 1998 for $640,000

Home Value

Trulia Estimate
$2.05M
Since last month
Decreased$16K (-0.8%)
Since last year
Decreased$126K (-5.8%)
Since last sale
Increased$1M (+220.8%)
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 +11% in the last 10 years
MonthEstimated value
2026
November 2026$2.05M
October 2026$2.09M
September 2026$2.07M
August 2026$2.09M
July 2026$2.18M
June 2026$2.13M
May 2026$2.17M
April 2026$2.18M
March 2026$2.2M
February 2026$2.08M
January 2026$2.08M
2025
2024
2023
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
69 Walnut St #4, Brookline, MA
0.23
Condo
$2,850,000
07/21/26
4
4
2,510
31 Highland Rd #1, Brookline, MA
0.20
Condo
$2,320,000
11/13/25
3
3.5
2,500
57-59 Highland Rd #57, Brookline, MA
0.17
Condo
$1,850,000
07/10/26
4
3
1,835
157 Cypress St #2, Brookline, MA
0.36
Condo
$1,795,000
08/21/26
4
3.5
2,075
3 Upland Rd #2, Brookline, MA
0.17
Condo
$1,090,000
05/04/26
3
2
1,655
99 Pond Ave #222, Brookline, MA
0.23
Condo
$640,000
08/31/26
2
2
1,300
241 Perkins St #G102, Boston, MA
0.53
Condo
$1,780,000
07/14/26
3
3.5
3,856
60 Glen Rd #108, Brookline, MA
0.16
Condo
$900,000
05/14/26
2
2
1,249
166 Chestnut St #1, Brookline, MA
0.28
Condo
$765,000
06/25/26
3
2
1,079
241 Perkins St #C402, Jamaica Plain, MA
0.54
Condo
$1,085,000
04/16/26
3
2.5
3,017

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
107 High St, Brookline, MA 02445
0.00
$1,777,900
3
3
2,350
Off Market
107 High St #6, Brookline, MA 02445
0.00
-
1
1
9,999
Off Market
123 High St, Brookline, MA 02445
0.02
$4,006,800
8
6
5,312
Off Market
99 High St, Brookline, MA 02445
0.02
$5,153,700
7
6
7,621
Off Market
70 Upland Rd, Brookline, MA 02445
0.03
$3,823,800
5
6
5,312
Off Market
112 High St, Brookline, MA 02445
0.04
$7,140,300
7
6.5
8,437
Off Market
112 High St #B, Brookline, MA 02445
0.04
-
1
1
900
Off Market
78 Upland Rd, Brookline, MA 02445
0.04
$6,049,100
6
5.5
6,767
Off Market
62 Upland Rd, Brookline, MA 02445
0.04
$3,462,600
5
4
3,604
Off Market
127 High St, Brookline, MA 02445
0.04
$3,660,300
5
2.5
3,656
Off Market
100 High St, Brookline, MA 02445
0.04
$3,453,900
6
4
5,055
Off Market
100 High St #6, Brookline, MA 02445
0.04
-
1
1
9,999
Off Market
55 Irving St, Brookline, MA 02445
0.05
$4,375,400
8
7.5
5,483
Off Market
56 Upland Rd, Brookline, MA 02445
0.05
$3,858,800
6
5
3,938
Off Market
1 Edgehill Rd, Brookline, MA 02445
0.05
$3,447,200
4
4
3,070
Off Market
131 High St, Brookline, MA 02445
0.06
$2,547,600
2
1
893
Off Market
131 High St #3, Brookline, MA 02445
0.06
-
Studio
-
-
Off Market
Edgehill Rd #CH, Brookline, MA 02445
0.06
-
2
2
1,600
Off Market
52 Upland Rd, Brookline, MA 02445
0.06
$3,246,500
8
4
4,651
Off Market
92 High St, Brookline, MA 02445
0.06
$5,312,800
7
4.5
6,988
Off Market

Local Information

  • Map ViewExplore the area around 111 High St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1906
4,927 sqft
$417/sqft
Garage

About this House

This condo is located at 111 High St, Brookline, MA. 111 High St is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 9 bedrooms, 5 bathrooms and approximately 4,927 sqft of floor space. This property was built in 1906.
111 High St, Brookline, MA 02445 is a 9 bedroom, 5 bathroom, 4,927 sqft condo in High Street Hill, built in 1906. It last sold for $640,000 on May 22, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,052,900, with a rent estimate of $7,502/month.

Home Details for 111 High St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 14
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1906
Property Type / Style
Property Type: Condo

Community

Units in Building: 1

Price and Tax history

DateEventPrice
May 22, 1998
Source: N/A
Sold
$640,000

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

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 111 High St

  • What is 111 High St estimated to be worth?
    Trulia's estimated value for 111 High St in Brookline, MA is $2,052,900.
  • What is the price history for 111 High St?
    111 High St in Brookline, MA last sold for $640,000 in May 1998.
  • 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.

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Apartments for Rent

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Off Market Homes Near 111 High St

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