44 High St #U, Brookline, MA 02445
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OFF MARKET

44 High St #U
Brookline, MA 02445

High Street Hill
  • 5 Beds
  • 2.5 Baths

$1,261,000

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $7,563/mo*
Refinance Your Home

$1,261,000

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $7,563/mo*
Refinance Your Home
5 Beds
2.5 Baths

Local Information

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

Home Highlights

Property Type
Single-Family Home

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 #U, 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. It is currently off market. The Trulia Estimate is $1,261,000, with a rent estimate of $5,943/month.

Home Details for 44 High St #U

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Price History for 44 High St #U

DatePriceEventSource
11/01/2025$8,750ListingRemovedZillow Rentals
06/09/2025$8,750Listed For RentZillow Rentals

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
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Comparable Sales for 44 High St #U

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

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 44 High St #U.
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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Explore by feature - Pet Friendly

410 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

93 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

694 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

86 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

1006 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

29 rentals with an outdoor space in Brookline, MA

Homes for sale near 44 High St #U

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Off Market Homes Near 44 High St #U

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Frequently asked questions about 44 High St #U

  • What is 44 High St #U estimated to be worth?
    Trulia's estimated value for 44 High St #U in Brookline, MA is $1,261,000.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.4M. That is down $16.67K 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.