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

$4,345,600

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 4,703 sqft (on 0.34 acres)

138 High St, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $25,880/mo*
Refinance Your Home
Currently Off Market - Sold Jun 6, 2019 for $3,150,000

Home Value

Trulia Estimate
$4.35M
Since last month
Decreased$138K (-3.1%)
Since last year
Increased$43K (+1%)
Since last sale
Increased$1M (+37.6%)
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 +133% in the last 10 years
MonthEstimated value
2026
August 2026$4.34M
July 2026$4.47M
June 2026$4.46M
May 2026$4.49M
April 2026$4.48M
March 2026$4.42M
February 2026$4.27M
January 2026$4.19M
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
36 Allerton St, Brookline, MA
0.22
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
14 Irving St, Brookline, MA
0.23
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
12 Zamora St, Boston, MA
0.46
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
54 Clark Rd, Brookline, MA
0.61
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
16 Kennard Rd, Brookline, MA
0.47
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
236 Walnut St, Brookline, MA
0.26
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
469 Walnut St, Brookline, MA
0.73
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
209 High St, Brookline, MA
0.16
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
115 Clark Rd, Brookline, MA
0.74
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182
213 Gardner Rd, Brookline, MA
0.85
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
19 Edgehill Rd, Brookline, MA 02445
0.03
$3,875,500
5
4
3,538
Off Market
30 Cumberland Ave #W1, Brookline, MA 02445
0.09
$823,900
1
1.5
991
Off Market
30 Cumberland Ave W #4, Brookline, MA 02445
0.09
-
2
2
1,246
Off Market
30 Cumberland Ave #3W, Brookline, MA 02445
0.09
-
2
2
1,246
Off Market
71 Highland Rd, Brookline, MA 02445
0.06
$950,000
3
1.5
1,000
Recently Sold
65 Glen Rd #H3, Brookline, MA 02445
0.10
$752,800
2
2
1,010
Off Market
65 Glen Rd #H6, Brookline, MA 02445
0.10
$998,900
2
2
1,282
Off Market
65 Glen Rd #H1, Brookline, MA 02445
0.10
$725,000
2
2
949
For Sale
75 Glen Rd #B-3, Brookline, MA 02445
0.11
$600,500
1
1
792
Off Market
57-59 Highland Rd, Brookline, MA 02445
0.10
$1,949,000
4
3
1,949
For Sale
81 Glen Rd #S1, Brookline, MA 02445
0.11
$1,093,000
2
2.5
1,492
Off Market
81 Glen Rd #S2, Brookline, MA 02445
0.11
$967,000
3
2
1,340
Recently Sold

Local Information

  • Map ViewExplore the area around 138 High St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1861
Lot Size
0.34 acres
Living Area
4,703 sqft
Price/Sqft
$924

About this House

c.1860. On Historic Pill Hill, beautifully & recently renovated home with Italianate-style influences. Sun abounds from tall windows, high ceilings. Liv. room with fireplace and gorgeous chandelier. Kitchen with professional grade appliances, white Carrera composite marble counters, dining area and open to family room w/ french doors to charming patios, grape arbor, and gardens with handsome stonework. Also on first floor is a bedroom, full bath, laundry room. The second floor holds Master BR and fabulous bath, two hall bedrooms and bath. There is a fantastic media room with beamed cathedral ceiling, a kitchenette, two more BRs and baths and laundry. All baths are by Restoration Hardware. 3rd Flr has a bonus bedroom. Much flexible-use space in this house. Fresh and bright feel. Restored stone wall,new wrought iron fence. Rebuilt one-car garage w/ lots of extra parking. Close prox. to schools, Brookline Village MBTA, market and restaurants, parks galore, Longwood Medical and Fenway Park
138 High St, Brookline, MA 02445 is a 6 bedroom, 5 bathroom, 4,703 sqft single-family home in High Street Hill, built in 1861. It last sold for $3,150,000 on Jun 6, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,345,600, with a rent estimate of $7,812/month.

Home Details for 138 High St

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 15
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1861Year Updated: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Jun 6, 2019
Source: N/A
Sold
$3,150,000
Apr 22, 2019
Source: Agent Provided
Pending
$3,150,000
Apr 16, 2019
Source: Agent Provided
Listed For Sale
$3,150,000
Nov 2, 2018
Source: Agent Provided
ListingRemoved
$3,150,000
Nov 2, 2018
Source: Agent Provided
PendingToActive
$3,150,000

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 138 High St

  • What is 138 High St estimated to be worth?
    Trulia's estimated value for 138 High St in Brookline, MA is $4,345,600.
  • What is the price history for 138 High St?
    138 High St in Brookline, MA last sold for $3,150,000 in June 2019.
  • 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 138 High St?
    The lot at 138 High St in Brookline, MA is about 0.34 acres (14,810 sq ft).

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Apartments for Rent

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Off Market Homes Near 138 High St

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