OFF MARKET

Off market sep 2012 for $2.5M

$4,572,046

Est. refi paymentEst. refi $697/mo

•

7,621

sq ft

99 High St, Brookline, MA 02445

About this home

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

Single-familyProperty Type

1862Year Built

0.58 acresLot Size

$600Est. Price/Sq.Ft.

8 spacesParking

Listed by Susan Rothstein • Hammond Residential R. E.

Bought with Dan Keating • Coldwell Banker Residential Brokerage - Brookline

Redfin checked: 2 minutes ago

•Source:MLS PIN #71353361

Redfin Estimate

$4,572,046

$2.1M since sold in September 2012$28K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 52.5% higher than the average sale price ($3.00M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,000,000
A
8 beds5 baths5,076 sq ft
16 Kennard Rd, Brookline, MA 02445
SOLD JUL 24, 2026
$2,325,000
B
7 beds4 baths4,544 sq ft
54 Clark Rd, Brookline, MA 02445
SOLD SEP 4, 2026
$3,172,425
C
6 beds4.5 baths6,440 sq ft
45 Parley Ave, Jamaica Plain, MA 02130
SOLD SEP 24, 2026
$2,500,000
D
6 beds3.5 baths5,748 sq ft
2 Mason Ter, Brookline, MA 02446
SOLD SEP 25, 2026
$4,368,000
E
6 beds4.5 baths4,060 sq ft
38 Fuller St, Brookline, MA 02446
SOLD DEC 4, 2025
$3,625,000
F
7 beds4 baths6,307 sq ft
469 Walnut St, Brookline, MA 02445

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Earn from this home

Sell

$3,000,455

Est. take-home

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Refinance

Est. cash available

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Rent

$8,934/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

97.3%

1.5% MoM

Median sale price

$1.0M

$142K MoM

Avg. days on market

56d

14 days MoM

Recently sold homes

16 MoM

New listings for sale

OPEN TODAY, 11:30AM TO 1PM
$399,000
Studio1 bath500 sq ft
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VIDEO TOUR
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4 beds4 baths3,498 sq ft
91 University Rd #2, Brookline, MA 02445
OPEN TODAY, 11:30AM TO 1:30PM
$1,700,000
4 beds2 baths2,254 sq ft
146 University Rd #146, Brookline, MA 02445
OPEN TODAY, 12PM TO 1:30PM
$4,250,000
5 beds3.5 baths6,313 sq ft
120 Rawson Rd, Brookline, MA 02445
EARLY ACCESS
$1,595,000
3 beds2 baths1,105 sq ft
69 Walnut St #7, Brookline, MA 02445
OPEN SUN, 1:15PM TO 2:15PM
$495,000
1 bed1 bath655 sq ft
44 Washington St #303, Brookline, MA 02445
EARLY ACCESS
$1,700,000
4 beds2 baths2,254 sq ft
146 University Rd #2, Brookline, MA 02445
$2,350,000
6 beds3 baths5,030 sq ft
309 Buckminster Rd, Brookline, MA 02445
$4,375,000
5 beds5.5 baths3,539 sq ft
291 Tappan St #291, Brookline, MA 02445
$2,399,900
6 beds4 baths3,454 sq ft
101-103 University Rd, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 99 High St

Year

Property tax

Land + Additions

Assessment*

2023

$46,824 (+2.7%)

$1,538,000 + $3,158,500

$4,696,500

2022

$45,577 (+8.1%)

$1,464,600 + $3,008,100

$4,472,700

2021

$42,147 (+7.8%)

$1,408,300 + $2,892,400

$4,300,700

2020

$39,113 (+5.9%)

$1,280,300 + $2,858,600

$4,138,900

2019

$36,935 (+9.1%)

$1,219,300 + $2,722,500

$3,941,800

2018

$33,868 (+1.5%)

$1,110,300 + $2,469,800

$3,580,100

2017

$33,370 (+1.5%)

$1,047,500 + $2,330,000

$3,377,500

2016

$32,891 (+4.1%)

$978,900 + $2,177,600

$3,156,500

2015

$31,604 (+2.6%)

$914,900 + $2,044,300

$2,959,200

2014

$30,789 (−14.5%)

$830,100 + $1,873,100

$2,703,200

2013

$36,016 (+2.2%)

$805,900 + $2,285,600

$3,091,500

2012

$35,243 (+2.5%)

$805,900 + $2,285,600

$3,091,500

2011

$34,389 (+3.7%)

$843,500 + $2,199,800

$3,043,300

2010

$33,174 (+1.9%)

$843,500 + $2,180,600

$3,024,100

2009

$32,544

$843,500 + $2,200,800

$3,044,300

Tax history for 99 High St

Year

Property tax

Land + Additions

Assessment*

2023

$46,824 (+2.7%)

$1,538,000 + $3,158,500

$4,696,500

2022

$45,577 (+8.1%)

$1,464,600 + $3,008,100

$4,472,700

2021

$42,147 (+7.8%)

$1,408,300 + $2,892,400

$4,300,700

2020

$39,113 (+5.9%)

$1,280,300 + $2,858,600

$4,138,900

2019

$36,935 (+9.1%)

$1,219,300 + $2,722,500

$3,941,800

2018

$33,868 (+1.5%)

$1,110,300 + $2,469,800

$3,580,100

2017

$33,370 (+1.5%)

$1,047,500 + $2,330,000

$3,377,500

2016

$32,891 (+4.1%)

$978,900 + $2,177,600

$3,156,500

2015

$31,604 (+2.6%)

$914,900 + $2,044,300

$2,959,200

2014

$30,789 (−14.5%)

$830,100 + $1,873,100

$2,703,200

2013

$36,016 (+2.2%)

$805,900 + $2,285,600

$3,091,500

2012

$35,243 (+2.5%)

$805,900 + $2,285,600

$3,091,500

2011

$34,389 (+3.7%)

$843,500 + $2,199,800

$3,043,300

2010

$33,174 (+1.9%)

$843,500 + $2,180,600

$3,024,100

2009

$32,544

$843,500 + $2,200,800

$3,044,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.58 Acres

Year renovated

1968

Sq. Ft.

7,621

Year built

1890

Style

Single Family Residential

County

Norfolk County

APN

40776

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Apr 3, 2024 • Active

Residential building

Perform an in-kind replacement of slate, rubber, and copper roofs on a residential building. All work must comply with building codes and local zoning bylaws.

Roofing

Dec 12, 2023 • Active

Residential building

Replace the deck flooring and handrails on an existing rear deck. All work must comply with building codes and local zoning bylaws.

Remodel

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Parking

Parking Information
Has Open Parking
Parking Spaces: 8
Parking Features: Driveway, Stone/Gravel

Interior

Master Bedroom Information
Area: 221
Length: 17
Width: 13
Level: Second
Features: Flooring - Hardwood

Bedroom #2 Information
Area: 168
Length: 12
Width: 14
Level: Second
Features: Flooring - Hardwood

Bedroom #3 Information
Area: 168
Length: 12
Width: 14
Level: Second
Features: Fireplace,Flooring - Hardwood

Bedroom #4 Information
Area: 120
Length: 12
Width: 10
Level: Second
Features: Fireplace,Flooring - Hardwood

Bedroom #5 Information
Area: 288
Length: 18
Width: 16
Level: Second

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 2
Master Bathroom Features: Yes

Bathroom #1 Information
Level: Second
Features: Bathroom - Tiled With Tub & Shower,Double Vanity

Bathroom #2 Information
Level: Second
Features: Bathroom - Tiled With Shower Stall

Bathroom #3 Information
Level: Second
Features: Bathroom - With Shower Stall

Living Room Information
Area: 420
Length: 28
Width: 15
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 242
Length: 22
Width: 11
Level: First
Features: Coffered Ceiling(s),Flooring - Hardwood

Dining Room Information
Area: 378
Length: 21
Width: 18
Level: First
Features: Beamed Ceilings,Flooring - Hardwood

Kitchen Information
Area: 216
Length: 18
Width: 12
Level: First
Features: Flooring - Hardwood,Pantry,Countertops - Stone/Granite/Solid,French Doors,Second Dishwasher

Office Room Information
Area: 143
Length: 13
Width: 11
Level: Second
Features: Bathroom - Full

Basement Information
Basement: Full, Partially Finished, Sump Pump, Concrete

Laundry Information
Laundry Dimen: 14X14
Laundry Features: Fireplace, Second Floor, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 7
Fireplace Features: Dining Room, Family Room, Living Room, Master Bedroom, Bedroom

Interior Features
# of Rooms (Total): 21
Door Features: Insulated Doors
Window Features: Insulated Windows, Storm Window(s)
Flooring: Hardwood, Flooring - Hardwood
Interior Features: Bathroom - Full, Bathroom - Half, Bathroom, Office, Library, Study, Inlaw Apt., Walk-Up Attic

Exterior

Building Information
Building Area (Total): 7,621
Foundation Area: 9,999
Foundation Details: Stone
Construction Materials: Stone
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced
Roof: Slate
Patio And Porch Features: Porch, Covered
Exterior Features: Porch, Covered Patio/Deck, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden, Stone Wall

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.58
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $33,353
Tax Year: 2012

Utilities

Utility Information
Utilities: for Gas Oven, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Heating: Hot Water, Radiant, Natural Gas, Fireplace

Location

Location Information
Directions: near Cumberland Ave
UnparsedAddress: 99 High Street, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Tennis Court(s), Walk/Jog Trails, Conservation Area, Public School, T-Station

Public facts

Beds: 6
Baths: 6.0
Sq. Ft.: 7,621
Stories: 2.0
Lot Size: 0.58 acres
Style: Single Family Residential
Year Built: 1890
Year Renovated: 1968
County: Norfolk County
APN: 40776

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
Exclusions: Two Pendant Light Fixt./Kit. Garden Pots
StandardStatus: Closed

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.5mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.6mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
3 weeks ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
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Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

59% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Brookline, MA • 02445

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.34M – $5.26M

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OPEN TODAY, 11:30AM TO 1:30PM

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OPEN TODAY, 12PM TO 1:30PM

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Home values near 99 High St

Data from public records.

Address	Redfin Estimate
107 High St, Brookline, MA 3 Beds \| 2.5 Baths \| 1747 Sq. Ft.	$1,770,909
92 High St, Brookline, MA 7 Beds \| 4.5 Baths \| 6988 Sq. Ft.	$4,215,016

Address	Redfin Estimate
111 High St, Brookline, MA 8 Beds \| 5 Baths \| - Sq. Ft.	$2,494,902
84 High St, Brookline, MA 3 Beds \| 3 Baths \| 5183 Sq. Ft.	$2,968,721

Address	Redfin Estimate
100 High St, Brookline, MA 6 Beds \| 3.5 Baths \| 5055 Sq. Ft.	$2,967,510
112 High St, Brookline, MA 7 Beds \| 6.5 Baths \| 8437 Sq. Ft.	$4,959,062

Property information provided by MLS PIN when last listed in 2012. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02445, MA

Sale history for 99 High St

Tax history for 99 High St

Public record

Property details

Around this home

Schools

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02445

Home values near 99 High St

More real estate resources