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

$5,291,100

Trulia Estimate
  • 7 Beds
  • 6 Baths
  • 7,621 sqft (on 0.58 acres)

99 High St, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $31,438/mo*
Refinance Your Home
Currently Off Market - Sold Sep 18, 2012 for $2,500,000

Home Value

Trulia Estimate
$5.29M
Since last month
Decreased$116K (-2.1%)
Since last year
Increased$95K (+1.8%)
Since last sale
Increased$3M (+112.4%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$5.31M
July 2026$5.43M
June 2026$5.39M
May 2026$5.37M
April 2026$5.36M
March 2026$5.33M
February 2026$5.18M
January 2026$4.99M
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
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
0.14
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
371 Walnut St, Brookline, MA
0.54
Single-Family Home
$5,250,000
03/02/26
7
5.5
6,193
16 Kennard Rd, Brookline, MA
0.45
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
54 Clark Rd, Brookline, MA
0.58
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
469 Walnut St, Brookline, MA
0.75
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
12 Zamora St, Boston, MA
0.53
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
236 Walnut St, Brookline, MA
0.22
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
213 Gardner Rd, Brookline, MA
0.80
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
21 Sargent Crossway, Brookline, MA
0.56
Single-Family Home
$7,030,000
04/03/26
5
6.5
5,772

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
19 Edgehill Rd, Brookline, MA 02445
0.09
$3,875,500
5
4
3,538
Off Market
35 Hawthorn Rd, Brookline, MA 02445
0.09
$2,872,900
5
3
3,245
Off Market
30 Cumberland Ave #W1, Brookline, MA 02445
0.11
$823,900
1
1.5
991
Off Market
30 Cumberland Ave W #4, Brookline, MA 02445
0.11
-
2
2
1,246
Off Market
30 Cumberland Ave #3W, Brookline, MA 02445
0.11
-
2
2
1,246
Off Market
65 Glen Rd #H3, Brookline, MA 02445
0.14
$752,800
2
2
1,010
Off Market
65 Glen Rd #H6, Brookline, MA 02445
0.14
$998,900
2
2
1,282
Off Market
65 Glen Rd #H1, Brookline, MA 02445
0.14
$725,000
2
2
949
For Sale
27 Irving St, Brookline, MA 02445
0.09
$3,314,500
7
4
5,244
Off Market
75 Glen Rd #B-3, Brookline, MA 02445
0.15
$600,500
1
1
792
Off Market
81 Glen Rd #S1, Brookline, MA 02445
0.17
$1,093,000
2
2.5
1,492
Off Market
81 Glen Rd #S2, Brookline, MA 02445
0.17
$967,000
3
2
1,340
Recently Sold

Local Information

  • Map ViewExplore the area around 99 High St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1862
Lot Size
0.58 acres
Living Area
7,621 sqft
Price/Sqft
$694

About this House

Pill Hill Hist. Magnificent & picturesque Tudor Revival enlarged & remodeled in 1907 by architect F. Manton Wakefield. Stone/timber/stucco structure w/stone terrace. Grand central hall & staircase. Exquisite detail of carved oak & cypress fireplaces & moldings. Leaded bullseye glass. Gracious entertaining & living spaces. Renovated kitchen w/doors to patio & pergola, 2 wonderful pantries. Renovated 15 rooms on 2 floors w/renovated baths. 3rd floor in-law/au pair. Exquisitely landscaped grounds
99 High St, Brookline, MA 02445 is a 7 bedroom, 6 bathroom, 7,621 sqft single-family home in High Street Hill, built in 1862. It last sold for $2,500,000 on Sep 18, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,291,100, with a rent estimate of $9,845/month.

Home Details for 99 High St

Interior Features

Interior Details
BasementNumber of Rooms: 20
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Stucco, Brick

Property Information

Year Built
Year Built: 1862Year Updated: 1968
Property Type / Style
Property Type: Single Family HomeArchitecture: Tudor

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price and Tax history

DateEventPrice
Sep 18, 2012
Source: N/A
Sold
$2,500,000
Jun 16, 2012
Source: Agent Provided
PriceChange
$2,600,000
Price decreased by 13%
Mar 19, 2012
Source: Agent Provided
Listed For Sale
$3,000,000

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

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 99 High St

  • What is 99 High St estimated to be worth?
    Trulia's estimated value for 99 High St in Brookline, MA is $5,291,100.
  • What is the price history for 99 High St?
    99 High St in Brookline, MA last sold for $2,500,000 in September 2012.
  • 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.
  • How big is the lot at 99 High St?
    The lot at 99 High St in Brookline, MA is about 0.58 acres (25,264 sq ft).

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Apartments for Rent

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Off Market Homes Near 99 High St

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Homes for sale near 99 High St

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