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

$3,034,700

Trulia Estimate
as of Oct 29, 2026
  • 5 Beds
  • 2.5 Baths
  • 3,150 sqft

44 High St, Brookline, MA 02445

High Street Hill

Home Highlights

Single-Family Home
3,150 sqft
$963/sqft

Local Information

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

About this House

What's unique:High-speed wi-fi
44 High St, Brookline, MA 02445

$8,500/month | Available July 1, 2026 (flex if earlier start date preferred)
5 Beds | 2.5 Baths | 3,150 Sq Ft
Fully Furnished | Single-Family | Off Street Parking 6 cars

Description
Turnkey, fully furnished and extremely comfortable Victorian home in Brookline's sought-after Pill Hill neighborhood ideally positioned minutes from the Longwood Medical Area and within easy reach of Brookline Village and Coolidge Corner and all of Boston and Cambridge.

Offering over 3,150 square feet across three levels, this sun-filled 5-bedroom residence blends classic architectural detail with modern functionality. The home features a spacious eat-in kitchen with Bosch appliances and a large island, multiple living and entertaining areas, and a seamless connection to a professionally landscaped private garden and bluestone terrace.

The top floor functions as a self-contained suite with its own bath, kitchenette, and living space ideal for guests, live-in help, or extended stays. A dedicated office/gym with Peloton supports work-from-home or executive lifestyles.

Designed for comfort and convenience, the home includes high-speed Wi-Fi, Sonos audio, in-home laundry, and rare off-street parking for up to six vehicles.

Key Features
Fully furnished, move-in ready (like staying at your best friend's house)
5 bedrooms + office/gym
Top-floor private suite with bath + kitchenette
Updated kitchen with Bosch appliances + island seating
Landscaped garden + blue stone patio with dining and grill
Sonos sound system + enterprise-speed Wi-Fi
Washer/dryer + utility sink
Parking for up to 6 cars (rare for Brookline)
Neighborhood Har-Tru tennis court access included

Location
Highly convenient location for medical, biotech, investment and academic professionals:
Minutes to Longwood Medical Area (Harvard Medical, BIDMC, Boston Children's) and MIT / Kendall Square.
Walk to Brookline Village & Coolidge Corner (restaurants, cafes, shops)
Green Line (T) access nearby
One block to Emerald Necklace parks and green space
Easy and pretty walk to Brookline High School & Lincoln School

Lease Details
Available July 1, 2026 (opportunity for earlier start date)
12-month lease preferred (flexible terms considered)
Pets considered on a case-by-case basis

Available July 1, 2026, through June, 2027. Opportunity to begin lease earlier. Pets are considered individually.
Tenants pay for snow removal, heat (oil), electric, gas (stove), and cable / internet.
Owners pay for garbage, landscaping, water, and other costs.

This is a non-smoking home.
44 High St, Brookline, MA 02445 is a 5 bedroom, 3 bathroom, 3,150 sqft single-family home in High Street Hill. It last sold for $2,650,000 on Jun 22, 2022 (31,076% above the $8,500 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $8,500 per month. That rental listing was removed on April 20, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,034,700.

Home Details for 44 High St

Interior Features

Heating & Cooling
Heating: Baseboard, Forced AirAir ConditioningCooling System: Central Air, Wall Unit, Window UnitHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Exterior Home Features
Garden
Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 44 High St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
36 Allerton St, Brookline, MA
0.04
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072 sqft
236 Walnut St, Brookline, MA
0.30
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963 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
61 Toxteth St, Brookline, MA
0.51
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484 sqft
71 Greenough St, Brookline, MA
0.56
Single-Family Home
$3,019,999
04/03/26
4
3
3,422 sqft
209 High St, Brookline, MA
0.39
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332 sqft
21 Hancock Rd, Brookline, MA
0.60
Single-Family Home
$2,385,000
12/17/25
4
3
2,286 sqft
24 Blake Rd, Brookline, MA
0.73
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377 sqft
9 Greenough St, Brookline, MA
0.53
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104 sqft

Nearby homes

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Price and Tax history

DateEventPrice
Apr 20, 2026
Source: Zillow Rentals
ListingRemoved
$8,500
Mar 28, 2026
Source: Zillow Rentals
Listed For Rent
$8,500
Sep 10, 2025
Source: Zillow Rentals
ListingRemoved
$8,750
Jun 26, 2025
Source: Zillow Rentals
Listed For Rent
$8,750
Jun 12, 2025
Source: Zillow Rentals
ListingRemoved
$8,750

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

This October

Trick-or-Treat Score

Built from what locals say about High Street Hill.
  • 98% say there are sidewalks
  • 63% say there's holiday spirit
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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 44 High St

  • What is 44 High St estimated to be worth?
    Trulia's estimated value for 44 High St in Brookline, MA is $3,034,700.
  • What is the price history for 44 High St?
    44 High St in Brookline, MA last sold for $2,650,000 in June 2022.
  • 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 $1.19M. That is down $50.67K from the prior month.
  • Does 44 High St have air conditioning?
    Yes, 44 High St in Brookline, MA has air conditioning.
  • Does 44 High St have laundry facilities?
    Yes, 44 High St in Brookline, MA has in-unit laundry.

Homes for rent near 44 High St

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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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