100 High St, Brookline, MA 02445
OFF MARKET

100 High St
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 4 Baths
  • 5,055 sqft (on 0.33 acres)

$3,606,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $21,090/mo*
Refinance Your Home

$3,606,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $21,090/mo*
Refinance Your Home
6 Beds
4 Baths
5,055 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 100 High St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 100 High St, Brookline, MA. 100 High St is in the High Street Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 6 bedrooms, 4 bathrooms and approximately 5,055 sqft of floor space. This property has a lot size of 0.33 acres and was built in 1887.
100 High St, Brookline, MA 02445 is a 6 bedroom, 4 bathroom, 5,055 sqft single-family home in High Street Hill, built in 1887. It last sold for $103,000 on Aug 1, 1978. It is currently off market. The Trulia Estimate is $3,606,000, with a rent estimate of $8,685/month.

Home Highlights

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

Home Details for 100 High St

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 13
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Wood

Property Information

Year Built
Year Built: 1887Year Updated: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price History for 100 High St

DatePriceEventSource
08/01/1978$103,000Sold
N/A

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$30,141
Assessment$3,053,800
Home facts updated by county records

Comparable Sales for 100 High St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.16
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.13
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
12 Zamora St, Boston, MA
0.50
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
27 Walnut Pl, Brookline, MA
0.20
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
236 Walnut St, Brookline, MA
0.26
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
209 High St, Brookline, MA
0.25
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
469 Walnut St, Brookline, MA
0.78
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
213 Gardner Rd, Brookline, MA
0.84
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
157 Aspinwall Ave, Brookline, MA
0.61
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
7 Dana St, Brookline, MA
0.47
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315

Nearby homes

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Assigned Schools

These are the assigned schools for 100 High St.
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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Homes for sale near 100 High St

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Off Market Homes Near 100 High St

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