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

27 High St
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 1 Bath
  • 1,300 sqft
3 Beds
1 Bath
1,300 sqft

Local Information

  • Map ViewExplore the area around 27 High St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Available AUGUST 15th or SEPTEMBER 1st

Virtual tour available upon request

3 bed / 1 bath on the first floor of a two family house

- Heat & hot water included!
- Big Bedrooms
- Separate kitchen w/dishwasher
- Laundry in basement (coin op)
- Parking for rent for $200/mo each. 2 Spots Available

Pets:
- No Cats (Owner is allergic)
- Small Dog OK

Deposits:
- First Months Rent, Last Months Rent & One Month Security Deposit

Broker Fee:
- One month rent due from incoming tenant
27 High St, Brookline, MA 02445 is a 3 bedroom, 1 bathroom, 1,300 sqft apartment in High Street Hill. It last sold for $430,000 on Dec 23, 1999 (12,547% above the $3,400 asking price). More recently, it was listed as a rental in July 2025 with an asking price of $3,400 per month. That rental listing was removed on August 13, 2025. It is currently off market. The Trulia Estimate rent is $3,986/month.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 27 High St

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
Dishwasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price History for 27 High St

DatePriceEventSource
08/13/2025$3,400ListingRemovedZillow Rentals
07/23/2025$3,400Listed For RentZillow Rentals
07/05/2025$3,400ListingRemovedZillow Rentals
06/05/2025$3,400Listed For RentZillow Rentals
03/28/2019$3,400ListingRemovedAgent Provided
03/21/2019$3,400Listed For RentAgent Provided
05/22/2018$3,400ListingRemovedAgent Provided
12/10/2017$3,400PriceChange
Agent Provided
08/21/2017$3,500Listed For RentAgent Provided
12/23/1999$430,000Sold
N/A

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$17,417
Assessment$1,764,600
Home facts updated by county records

Comparable Sales for 27 High St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
13 Linden St #8, Brookline, MA
0.26
Apartment
$714,474
01/23/26
2
1
1,088
77 Pond Ave #308, Brookline, MA
0.15
Apartment
$450,000
04/28/26
1
1
720
33 Pond Ave #1207, Brookline, MA
0.15
Apartment
$880,000
10/15/25
2
2
1,300
36 Saint Paul St #B, Brookline, MA
0.52
Apartment
$470,000
06/12/26
2
1
-
20 Saint Paul St #2, Brookline, MA
0.49
Apartment
$400,000
10/14/25
2
1
703
70 Day St, Jamaica Plain, MA
0.67
Apartment
$697,000
05/18/26
3
1
1,000
28 Saint Paul St #1, Brookline, MA
0.49
Apartment
$663,000
08/12/25
2
1
715
135 Calumet St #2, Roxbury, MA
0.76
Apartment
$685,000
10/24/25
3
1
999
441 Washington St #5, Brookline, MA
0.48
Apartment
$999,999
06/01/26
3
2
1,541
425 S Huntington Ave #9, Jamaica Plain, MA
0.78
Apartment
$525,000
04/30/26
2
1
950
Home facts updated by county records

Nearby homes

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Assigned Schools

These are the assigned schools for 27 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

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

27 rentals with an outdoor space in Brookline, MA

Homes for sale near 27 High St

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Off Market Homes Near 27 High St

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