39 Irving St, Brookline, MA 02445
Property image
Property image
OFF MARKET

39 Irving St
Brookline, MA 02445

High Street Hill
  • 5 Beds
  • 5 Baths
  • 4,959 sqft (on 0.32 acres)

$5,323,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $31,909/mo*
Refinance Your Home

$5,323,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $31,909/mo*
Refinance Your Home
5 Beds
5 Baths
4,959 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 39 Irving St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1875
Lot Size
0.32 acres
Living Area
4,959 sqft
Price/Sqft
$1,073

About this House

This Pill Hill treasure, built in 1875 and extensively renovated and restored in 1999, has been meticulously cared for over the years. Architectural period detail throughout, 11 foot ceilings, custom mahogany cabinets, 16x37 living room with access to patio and gardens. Expansive master suite with sitting room and sleeping porch. Gorgeous, manicured gardens for family entertainment. Five minute walk to Brookline Village and public transportation.
39 Irving St, Brookline, MA 02445 is a 5 bedroom, 6 bathroom, 4,959 sqft single-family home in High Street Hill, built in 1875. It last sold for $3,500,000 on Aug 1, 2016. It is currently off market. The Trulia Estimate is $5,323,000, with a rent estimate of $8,444/month.

Home Details for 39 Irving St

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 13
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick

Property Information

Year Built
Year Built: 1875Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price History for 39 Irving St

DatePriceEventSource
08/01/2016$3,500,000Sold
N/A
05/06/2016$3,100,000PendingAgent Provided
05/02/2016$3,100,000Listed For SaleAgent Provided
04/08/1999$1,070,000Sold
N/A

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$40,612
Assessment$4,114,700
Home facts updated by county records

Comparable Sales for 39 Irving St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
36 Allerton St, Brookline, MA
0.11
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
14 Irving St, Brookline, MA
0.08
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
54 Clark Rd, Brookline, MA
0.56
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
213 Gardner Rd, Brookline, MA
0.78
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
115 Clark Rd, Brookline, MA
0.70
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182
236 Walnut St, Brookline, MA
0.21
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.57
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
157 Aspinwall Ave, Brookline, MA
0.55
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
232 Kent St, Brookline, MA
0.76
Single-Family Home
$4,000,000
08/01/25
5
4.5
5,296

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 39 Irving 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

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

355 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

70 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

559 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

76 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

833 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

24 rentals with an outdoor space in Brookline, MA

Homes for sale near 39 Irving St

Skip to last item
Skip to first item

Off Market Homes Near 39 Irving St

Skip to last item
Skip to first item