21 High St #2, Brookline, MA 02445
OFF MARKET

$1,067,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,499 sqft

21 High St #2, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $6,400/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.07M
Since last month
Decreased$13K (-1.2%)
Since last year
Decreased$24K (-2.2%)
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 +32% in the last 10 years
MonthEstimated value
2026
August 2026$1.07M
July 2026$1.08M
June 2026$1.09M
May 2026$1.1M
April 2026$1.09M
March 2026$1.08M
February 2026$1.05M
January 2026$1.03M
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
3 Upland Rd #2, Brookline, MA
0.08
Condo
$1,090,000
05/04/26
3
2
1,655
39 Kent St #4, Brookline, MA
0.19
Condo
$1,200,000
05/26/26
3
2
1,180
48 Kent St #5, Brookline, MA
0.21
Condo
$1,035,000
05/15/26
3
2
1,267
77 Pond Ave #1506, Brookline, MA
0.14
Condo
$790,000
03/31/26
2
2
1,260
33 Pond Ave #905, Brookline, MA
0.14
Condo
$750,000
07/27/26
2
2
1,260
255 Walnut St #B, Brookline, MA
0.34
Condo
$1,310,000
06/29/26
3
1.5
1,543
114 Davis Ave #2, Brookline, MA
0.30
Condo
$1,265,000
07/30/26
3
2
1,247
34 Station St #3, Brookline, MA
0.17
Condo
$950,000
08/03/26
2
2
1,250
33 Pond Ave #419, Brookline, MA
0.18
Condo
$730,000
10/08/25
2
2
1,270
44 Washington St #501, Brookline, MA
0.14
Condo
$720,000
12/19/25
2
2
1,005

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
72 Walnut St #1, Brookline, MA 02445
0.02
$1,411,000
3
2.5
1,600
Off Market
69 Walnut St #15, Brookline, MA 02445
0.04
$1,588,200
3
2
1,395
Off Market
69 Walnut St #14, Brookline, MA 02445
0.04
$1,782,600
3
3
1,535
Off Market
69 Walnut St #10A, Brookline, MA 02445
0.04
-
2
2
1,175
Off Market
69 Walnut St #4, Brookline, MA 02445
0.04
$2,850,000
4
4
2,510
Recently Sold
20 Boylston St #2, Jamaica Plain, MA 02130
0.04
-
3
2
1,521
Off Market
82 Walnut St #1, Brookline, MA 02445
0.02
$678,000
2
1
970
Off Market
88 Walnut St #3, Brookline, MA 02445
0.03
$833,100
2
1
975
Off Market
88 Walnut St #1, Brookline, MA 02445
0.03
$1,014,600
2
2
1,365
Off Market
96 Walnut St, Brookline, MA 02445
0.03
-
4
2
2,288
Off Market
48 Boylston St, Jamaica Plain, MA 02130
0.05
-
6
6
4,992
Off Market
115 Walnut St #3, Brookline, MA 02445
0.06
$1,783,000
4
2
2,185
Off Market

Local Information

  • Map ViewExplore the area around 21 High St #2.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1890
Living Area
1,499 sqft
Price/Sqft
$712
Parking
Garage

About this House

This condo is located at 21 High St #2, Brookline, MA. 21 High St #2 is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 3 bedrooms, 2 bathrooms and approximately 1,499 sqft of floor space. This property was built in 1890.
21 High St #2, Brookline, MA 02445 is a 3 bedroom, 2 bathroom, 1,499 sqft condo in High Street Hill, built in 1890. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,067,000, with a rent estimate of $5,062/month.

Home Details for 21 High St #2

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1890
Property Type / Style
Property Type: CondoArchitecture: Row House

Community

Units in Building: 1

Price and Tax history

YearProperty taxTax assessment
2025
$9,236
$935,800
Home facts updated by county records

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

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

Frequently asked questions about 21 High St #2

  • What is 21 High St #2 estimated to be worth?
    Trulia's estimated value for 21 High St #2 in Brookline, MA is $1,067,000.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • What do residents say about the High Street Hill neighborhood?
    Residents describe the High Street Hill neighborhood in Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in High Street Hill, Brookline.

Explore by feature - Pet Friendly

279 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

64 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

545 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

57 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

816 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

18 rentals with an outdoor space in Brookline, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 21 High St #2

Skip to last item
Skip to first item

Homes for sale near 21 High St #2

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