27 Upland Rd, Brookline, MA 02445
OFF MARKET

$1,770,100

Trulia Estimate
as of Nov 14, 2026
  • 5 Beds
  • 2 Baths
  • 2,000 sqft

27 Upland Rd, Brookline, MA 02445

High Street Hill

Home Highlights

Single-Family Home
2,000 sqft
$885/sqft
Attached Garage

Local Information

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

About this House

What's unique:Central air conditioningForced-air heatingUpdated kitchenImproved patioPrivate patioRecently renovated
Beautifully Renovated 5-Bedroom Home with Finished Attic, Basement & 3-Car Parking in Brookline

Welcome to 27 Upland Road, a spacious and recently renovated 5-bedroom, 2-bathroom home in a highly desirable Brookline neighborhood.

The home offers approximately 2,000 sq. ft. of main living space, plus an additional ~500 sq. ft. finished attic and ~1,000 sq. ft. basement, providing an exceptional amount of flexible space for a large family, professionals working from home, recreation, storage, or a home gym. The house is Lead free since 2020

The home has been thoughtfully updated, including fresh interior paint, an updated kitchen, renovated/finished attic and basement spaces, an improved patio, and refreshed landscaping. Major mechanical systems have also been updated, including the water heater, central air conditioning, and forced-air heating system, providing year-round comfort and peace of mind.

The bright ~300 sq. ft. enclosed patio/sunroom is a wonderful bonus space, featuring abundant windows and natural light and offering plenty of room for relaxing, dining, working, or entertaining.

Property Highlights
5 bedrooms
2 full bathrooms
Approximately 2,000 sq. ft. main living area
Approximately 500 sq. ft. finished attic
Approximately 1,000 sq. ft. basement
Approximately 300 sq. ft. enclosed patio/sunroom
Recently renovated and freshly painted
Updated kitchen
Updated water heater
Central air conditioning
Forced-air heating
Private patio and landscaped outdoor space
1-car indoor garage
2 additional driveway parking spaces
Approximately 3 minutes to the Green Line
Close to shopping, restaurants, hospitals, and everyday amenities
Convenient access to Boston and surrounding communities

The renter is responsible for water, electric and snow removal
27 Upland Rd, Brookline, MA 02445 is a 5 bedroom, 2 bathroom, 2,000 sqft single-family home in High Street Hill. It last sold for $1,280,000 on Mar 27, 2020 (21,233% above the $6,000 asking price). More recently, it was listed as a rental in October 2026 with an asking price of $6,000 per month. That rental listing was removed on October 9, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,770,100, with a rent estimate of $6,372/month.

Home Details for 27 Upland Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Heat PumpAir ConditioningCooling System: Air Conditioner, Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
GarageParking: Attached Garage, On Site

Comparable Sales for 27 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
50 Waverly St, Brookline, MA
0.31
Single-Family Home
$2,445,000
05/12/26
4
2
2,383 sqft
71 Highland Rd, Brookline, MA
0.27
Single-Family Home
$950,000
04/30/26
3
1.5
1,000 sqft
14A Linden Pl, Brookline, MA
0.40
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380 sqft
61 Toxteth St, Brookline, MA
0.54
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484 sqft
209 High St, Brookline, MA
0.35
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332 sqft
18 Cushing Rd, Brookline, MA
0.43
Single-Family Home
$1,351,000
01/23/26
2
2
1,230 sqft
43 Waverly St, Brookline, MA
0.31
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676 sqft
36 Allerton St, Brookline, MA
0.10
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072 sqft
9 Greenough St, Brookline, MA
0.49
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104 sqft
236 Walnut St, Brookline, MA
0.23
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963 sqft

Nearby homes

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Price and Tax history

DateEventPrice
Oct 9, 2026
Source: Zillow Rentals
ListingRemoved
$6,000
Oct 5, 2026
Source: Zillow Rentals
Listed For Rent
$6,000
Mar 27, 2020
Source: N/A
Sold
$1,280,000
Feb 16, 2020
Source: Agent Provided
Pending
$1,590,000
Jan 29, 2020
Source: Agent Provided
PriceChange
$1,590,000
Price decreased by 4%

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

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 27 Upland Rd

  • What is 27 Upland Rd estimated to be worth?
    Trulia's estimated value for 27 Upland Rd in Brookline, MA is $1,770,100.
  • What is the price history for 27 Upland Rd?
    27 Upland Rd in Brookline, MA last sold for $1,280,000 in March 2020.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.25M. That is up $65.53K from the prior month.
  • Does 27 Upland Rd have air conditioning?
    Yes, 27 Upland Rd in Brookline, MA has air conditioning.
  • Does 27 Upland Rd have laundry facilities?
    Yes, 27 Upland Rd in Brookline, MA has in-unit laundry.

Homes for rent near 27 Upland Rd

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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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