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

$6,911,000

Trulia Estimate
  • 7 Beds
  • 6.5 Baths
  • 7,425 sqft (on 0.50 acres)

59 High St, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $41,113/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2022 for $6,675,000

Home Value

Trulia Estimate
$6.91M
Since last month
Decreased$197K (-2.8%)
Since last year
Increased$91K (+1.3%)
Since last sale
Increased$240K (+3.6%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$6.92M
July 2026$7.11M
June 2026$7.08M
May 2026$7.11M
April 2026$7.21M
March 2026$7.01M
February 2026$6.86M
January 2026$6.73M
2025
2024
2023
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
36 Allerton St, Brookline, MA
0.06
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
371 Walnut St, Brookline, MA
0.60
Single-Family Home
$5,250,000
03/02/26
7
5.5
6,193
14 Irving St, Brookline, MA
0.08
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
21 Sargent Crossway, Brookline, MA
0.65
Single-Family Home
$7,030,000
04/03/26
5
6.5
5,772
469 Walnut St, Brookline, MA
0.81
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
54 Clark Rd, Brookline, MA
0.60
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
16 Kennard Rd, Brookline, MA
0.50
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
80 Dudley St, Brookline, MA
0.92
Single-Family Home
$8,925,000
04/30/26
7
9
7,240
100 Cottage St, Brookline, MA
0.89
Single-Family Home
$5,790,000
12/19/25
6
7.5
9,380
213 Gardner Rd, Brookline, MA
0.80
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507

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
36 Allerton St, Brookline, MA 02445
0.06
$4,250,000
5
4.5
4,072
Recently Sold
82 Walnut St #1, Brookline, MA 02445
0.09
$678,000
2
1
970
Off Market
38 Juniper St #108, Brookline, MA 02445
0.09
$502,000
2
1
822
Recently Sold
88 Walnut St #1, Brookline, MA 02445
0.08
$1,010,600
2
2
1,365
Off Market
88 Walnut St #3, Brookline, MA 02445
0.09
$833,100
2
1
975
Off Market
96 Walnut St, Brookline, MA 02445
0.08
$1,861,200
4
2
2,288
Off Market
72 Walnut St #1, Brookline, MA 02445
0.09
$1,411,000
3
2.5
1,600
Off Market
48 Allerton St, Brookline, MA 02445
0.08
$3,438,400
6
2.5
3,748
Off Market
28 Juniper St #79, Brookline, MA 02445
0.11
$517,700
1
1
638
Off Market
32 Juniper St #96, Brookline, MA 02445
0.11
$615,700
2
1
822
Off Market
32 Juniper St #91, Brookline, MA 02445
0.11
$671,900
2
1
822
Off Market
32 Juniper St #97, Brookline, MA 02445
0.11
$655,600
2
1
822
Off Market

Local Information

  • Map ViewExplore the area around 59 High St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1881
Lot Size
0.5 acres
Living Area
7,425 sqft
Price/Sqft
$931
Parking
Garage

About this House

New custom-built home 2020. Elevator & an extra bedroom can be converted from the existing Ipe deck. 3D Matterport in 4k available to view the home. Perfection is the only word to describe this stunning property. Ideal for the urban family who wants a city lifestyle but demands an outdoor experience that is breathtaking. Pool capable. The terrace has a Wolf Grill , ashlar stonewall that exudes quality. Heated garage has a 100 amp Tesla charging station, wifi, cameras & alarms. Second floor has a 600 sq foot heated Ipe private deck with 25 trees in custom cedar planters, cameras and wifi.( Could be converted to additional bedroom) Unlimited hyper luxury interior customizations with over the top features. Radiant heat in entire house, 5 wolf ovens, 2 Sub-Zeros, 3 washers/dryers, 2 dishwashers, all 4 utilities added, new sewer, 2 inch water line, 4 inch gas line, 400 amps electric buried. Option for smart control4 audio/video allowing to run the home from your phone anywhere in the world!
59 High St, Brookline, MA 02445 is a 7 bedroom, 8 bathroom, 7,425 sqft single-family home in High Street Hill, built in 1881. It last sold for $6,675,000 on Sep 16, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $6,911,000, with a rent estimate of $7,091/month.

Home Details for 59 High St

Interior Features

Interior Details
BasementNumber of Rooms: 23Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation RoomWet BarCeiling Fan
Heating & Cooling
Heating: Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 4Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: WoodGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 8Parking: Garage Detached

Property Information

Year Built
Year Built: 1881Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.50 acres

Mobile R/V

RV Parking
Rv Parking

Additional Information

Intercom

Price and Tax history

DateEventPrice
Sep 16, 2022
Source: MLS PIN #73000006
Sold
$6,675,000
Jul 19, 2022
Source: MLS PIN #73000006
PriceChange
$6,900,000
Price decreased by 5%
Jun 18, 2022
Source: MLS PIN #73000006
Listed For Sale
$7,298,000
Feb 17, 2022
Source: N/A
ListingRemoved
Feb 12, 2022
Source: N/A
Listed For Sale
$7,900,000

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

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 59 High St

  • What is 59 High St estimated to be worth?
    Trulia's estimated value for 59 High St in Brookline, MA is $6,911,000.
  • What is the price history for 59 High St?
    59 High St in Brookline, MA last sold for $6,675,000 in September 2022.
  • 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.
  • Does 59 High St have air conditioning?
    Yes, 59 High St in Brookline, MA has air conditioning.
  • Does 59 High St have laundry facilities?
    Yes, 59 High St in Brookline, MA has laundry facilities.

Explore by feature - Pet Friendly

278 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

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Explore by feature - Air Conditioning

539 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

58 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

807 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

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Off Market Homes Near 59 High St

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Homes for sale near 59 High St

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