44 High St, Brookline, MA 02445
OFF MARKET

44 High St
Brookline, MA 02445

High Street Hill
  • 5 Beds
  • 2.5 Baths
  • 3,150 sqft

$3,084,200

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $18,357/mo*
Refinance Your Home

$3,084,200

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $18,357/mo*
Refinance Your Home
5 Beds
2.5 Baths
3,150 sqft

Local Information

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

Description

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.
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. This description is from April 02, 2026

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
49 days ago

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
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: Jul 1st

Exterior Features

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

Price History for 44 High St

DatePriceEventSource
04/20/2026$8,500ListingRemovedZillow Rentals
03/28/2026$8,500Listed For RentZillow Rentals
09/10/2025$8,750ListingRemovedZillow Rentals
06/26/2025$8,750Listed For RentZillow Rentals
06/12/2025$8,750ListingRemovedZillow Rentals
05/01/2025$8,750Listed For RentZillow Rentals
10/14/2024$9,500ListingRemovedZillow Rentals
06/14/2024ListingRemovedZillow Rentals
05/08/2024$9,500Listed For RentZillow Rentals
06/22/2022$2,650,000Sold
MLS PIN #72970039
04/27/2022$2,650,000PendingWilliam Raveis Real Estate, Mortgage & Insurance #72970039
04/26/2022$2,650,000ContingentMLS PIN #72970039
04/21/2022$2,650,000Listed For SaleMLS PIN #72970039
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Property Tax and Assessment

Year2025
Tax$22,252
Assessment$2,254,500
Home facts updated by county records

Comparable Sales for 44 High St

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
129 Walnut St, Brookline, MA
0.10
Single-Family Home
$1,150,000
06/04/25
6
2.5
3,784
19 Edgehill Rd, Brookline, MA
0.21
Single-Family Home
$3,765,000
05/28/25
5
4
3,538
236 Walnut St, Brookline, MA
0.30
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
7 Dana St, Brookline, MA
0.44
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
50 Waverly St, Brookline, MA
0.36
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
27 Irving St, Brookline, MA
0.11
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
23 Toxteth St, Brookline, MA
0.42
Single-Family Home
$2,201,000
06/23/25
4
2.5
2,634
61 Toxteth St, Brookline, MA
0.51
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484

Assigned Schools

These are the assigned schools for 44 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

Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 44 High St

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Homes for rent near 44 High St

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Off Market Homes Near 44 High St

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Explore by feature

44 High St, Brookline, MA 02445 is a 5 bedroom, 3 bathroom, 3,150 sqft single-family home. 44 High St is located in High Street Hill, Brookline. This property is not currently available for sale. 44 High St was last sold on Jun 22, 2022 for $2,650,000 (31,076% higher than the asking price of $8,500). The current Trulia Estimate for 44 High St is $3,084,200.