44 High St #D, Brookline, MA 02445
Property image
Property image
OFF MARKET

$1,176,400

Trulia Estimate
as of Aug 31, 2026
  • 5 Beds
  • 2.5 Baths
  • 5 Beds
  • 2.5 Baths

44 High St #D, Brookline, MA 02445

High Street Hill

Home Highlights

Property Type
Single-Family Home

Local Information

  • Map ViewExplore the area around 44 High St #D.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Imagine Elegant, fully furnished Victorian rental in Brookline's sought-after Pill Hill neighborhood.

This naturally sunny 5-bedroom, 2.5-bathroom single-family home offers over 3,150 square feet of updated living space, a beautifully landscaped private garden and bluestone terrace, and parking for six vehicles. Near Brookline Village, Coolidge Corner, Jamaica Plain, and Longwood Medical Area.

It's unique. Don't miss it. Text or email right now to learn more!
44 High St #D, Brookline, MA 02445 is a 5 bedroom, 3 bathroom single-family home in High Street Hill. More recently, it was listed as a rental in June 2025 with an asking price of $8,750 per month. That rental listing was removed on November 1, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,176,400, with a rent estimate of $6,544/month.

Home Details for 44 High St #D

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Comparable Sales for 44 High St #D

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.10
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873 sqft
36 Allerton St, Brookline, MA
0.04
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072 sqft
43 Waverly St, Brookline, MA
0.35
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676 sqft
50 Waverly St, Brookline, MA
0.36
Single-Family Home
$2,445,000
05/12/26
4
2
2,383 sqft
236 Walnut St, Brookline, MA
0.30
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963 sqft
71 Highland Rd, Brookline, MA
0.29
Single-Family Home
$950,000
04/30/26
3
1.5
1,000 sqft
61 Toxteth St, Brookline, MA
0.51
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484 sqft
209 High St, Brookline, MA
0.39
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332 sqft
14-14A Linden Pl, Brookline, MA
0.39
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380 sqft
71 Greenough St, Brookline, MA
0.56
Single-Family Home
$3,019,999
04/03/26
4
3
3,422 sqft

Nearby homes

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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

Price and Tax history

DateEventPrice
Nov 1, 2025
Source: Zillow Rentals
ListingRemoved
$8,750
Jun 9, 2025
Source: Zillow Rentals
Listed For Rent
$8,750

Frequently asked questions about 44 High St #D

  • What is 44 High St #D estimated to be worth?
    Trulia's estimated value for 44 High St #D in Brookline, MA is $1,176,400.
  • 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.
  • What do residents say about the High Street Hill neighborhood?
    Residents describe the High Street Hill neighborhood in Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in High Street Hill, Brookline.

Homes for rent near 44 High St #D

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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