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

44 High St
Brookline, MA 02445

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

$3,082,300

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $18,038/mo*
Refinance Your Home

$3,082,300

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $18,038/mo*
Refinance Your Home
5 Beds
2.5 Baths
3,150 sqft

Local Information

  • Map ViewExplore the area around 44 High St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- 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.
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. It is currently off market. The Trulia Estimate is $3,082,300, with a rent estimate of $7,922/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
103 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: now

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

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333MoM
Sale-to-List Price
99.9%
0.9%MoM
Price per sq ft
$814
$5MoM
Available listings
238
11MoM
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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
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
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
61 Toxteth St, Brookline, MA
0.51
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484
27 Walnut Pl, Brookline, MA
0.26
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
71 Greenough St, Brookline, MA
0.56
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
157 Aspinwall Ave, Brookline, MA
0.47
Single-Family Home
$2,800,000
09/22/25
4
4
3,515

Nearby homes

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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

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

368 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

80 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

562 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

82 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

948 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

27 rentals with an outdoor space in Brookline, MA

Homes for sale near 44 High St

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Off Market Homes Near 44 High St

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