138 High St, Brookline, MA 02445
OFF MARKET

138 High St
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 5 Baths
  • 4,703 sqft (on 0.34 acres)

$4,466,400

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $25,732/mo*
Refinance Your Home

$4,466,400

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $25,732/mo*
Refinance Your Home
6 Beds
5 Baths
4,703 sqft
(on 0.34 acres)

Local Information

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

Description

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
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 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 History for 138 High St

DatePriceEventSource
06/06/2019$3,150,000Sold
N/A
04/22/2019$3,150,000PendingAgent Provided
04/16/2019$3,150,000Listed For SaleAgent Provided
11/02/2018$3,150,000ListingRemovedAgent Provided
11/02/2018$3,150,000PendingToActiveAgent Provided
11/02/2018$3,150,000PendingAgent Provided
10/26/2018$3,150,000Listed For SaleAgent Provided
08/21/2013$1,525,000Sold
N/A
05/20/2013$1,750,000ListingRemovedAgent Provided
12/21/2012$1,750,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$38,051
Assessment$3,855,200
Home facts updated by county records

Comparable Sales for 138 High St

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
27 Walnut Pl, Brookline, MA
0.20
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
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
24 Lochstead Ave, Jamaica Plain, MA
0.69
Single-Family Home
$3,100,000
10/07/25
6
5
3,209

Nearby homes

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Assigned Schools

These are the assigned schools for 138 High St.
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

Apartments for Rent

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Homes for sale near 138 High St

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Off Market Homes Near 138 High St

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Homes for rent near 138 High St

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138 High St, Brookline, MA 02445 is a 6 bedroom, 5 bathroom, 4,703 sqft single-family home built in 1861. 138 High St is located in High Street Hill, Brookline. This property is not currently available for sale. 138 High St was last sold on Jun 6, 2019 for $3,150,000. The current Trulia Estimate for 138 High St is $4,466,400.