99 High St, Brookline, MA 02445
OFF MARKET

99 High St
Brookline, MA 02445

High Street Hill
  • 7 Beds
  • 6 Baths
  • 7,621 sqft (on 0.58 acres)

$5,273,500

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $30,918/mo*
Refinance Your Home

$5,273,500

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $30,918/mo*
Refinance Your Home
7 Beds
6 Baths
7,621 sqft
(on 0.58 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 99 High St

Interior Features

Interior Details
BasementNumber of Rooms: 20
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
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 History for 99 High St

DatePriceEventSource
09/18/2012$2,500,000Sold
N/A
06/16/2012$2,600,000PriceChange
Agent Provided
03/19/2012$3,000,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$50,525
Assessment$5,119,000
Home facts updated by county records

Comparable Sales for 99 High St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27 Irving St, Brookline, MA
0.09
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
14 Irving St, Brookline, MA
0.13
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
27 Walnut Pl, Brookline, MA
0.17
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
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
19 Edgehill Rd, Brookline, MA
0.09
Single-Family Home
$3,765,000
05/28/25
5
4
3,538
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
212 Aspinwall Ave, Brookline, MA
0.60
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
236 Walnut St, Brookline, MA
0.22
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963

Nearby homes

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Assigned Schools

These are the assigned schools for 99 High St.
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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 99 High St

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Off Market Homes Near 99 High St

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Homes for rent near 99 High St

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99 High St, Brookline, MA 02445 is a 7 bedroom, 6 bathroom, 7,621 sqft single-family home built in 1862. 99 High St is located in High Street Hill, Brookline. This property is not currently available for sale. 99 High St was last sold on Sep 18, 2012 for $2,500,000. The current Trulia Estimate for 99 High St is $5,273,500.