14 Upland Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

$2,003,000

Trulia Estimate
as of Nov 13, 2026
  • 3 Beds
  • 1 Bath
  • 1,143 sqft

14 Upland Rd, Brookline, MA 02445

High Street Hill

Home Highlights

Apartment
1,143 sqft
$1,752/sqft

Local Information

  • Map ViewExplore the area around 14 Upland Rd.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Nice back porchHardwood floorsGreen spaceTon of closetsFront area foyerLarge pantry
Available September 1st. Welcome to Upland Road near Brookline Village. A great location, just 4-5 minutes to the Brookline Village Green line MBTA station with great access to the Longwood Medical Center, Fenway/Kenmore and downtown Boston. This property features a large footprint with expansive living and dining rooms, a large pantry, dishwasher, gas stove, hardwood floors and an array of windows allowing an abundance of natural sunlight. Other features include free laundry on site, a nice back porch and green space, 3 large bedrooms, high ceilings, ton of closets and a front area foyer. Gas heat. Cats are negotiable. Multiple car parking for rent at property driveway. Inquire today!
14 Upland Rd, Brookline, MA 02445 is a 3 bedroom, 1 bathroom, 1,143 sqft apartment in High Street Hill. More recently, it was listed as a rental in June 2025 with an asking price of $3,300 per month. That rental listing was removed on June 17, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,003,000, with a rent estimate of $3,812/month.

Home Details for 14 Upland Rd

Interior Features

Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 14 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
13 Linden St #8, Brookline, MA
0.29
Apartment
$714,474
01/23/26
2
1
1,088 sqft
386 Riverway #4, Boston, MA
0.40
Apartment
$430,000
11/18/25
2
1
1,125 sqft
394 Riverway #10, Boston, MA
0.35
Apartment
$445,000
11/14/25
2
1
903 sqft
77 Pond Ave #308, Brookline, MA
0.19
Apartment
$450,000
04/28/26
1
1
720 sqft
238 S Huntington Ave #5, Jamaica Plain, MA
0.53
-
-
-
3
1
907 sqft
70 Day St, Jamaica Plain, MA
0.69
Apartment
$697,000
05/18/26
3
1
1,000 sqft
441 Washington St #5, Brookline, MA
0.47
Apartment
$999,999
06/01/26
3
2
1,541 sqft
49 Harvard Ave #4, Brookline, MA
0.50
Apartment
$974,000
06/15/26
1
1
700 sqft
425 S Huntington Ave #9, Jamaica Plain, MA
0.78
Apartment
$525,000
04/30/26
2
1
950 sqft
45 Longwood Ave #A, Brookline, MA
0.72
Apartment
$1,300,000
01/30/26
1
1
916 sqft
Home facts updated by county records

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Price and Tax history

DateEventPrice
Jun 17, 2025
Source: Zillow Rentals
ListingRemoved
$3,300
Jun 15, 2025
Source: Zillow Rentals
Listed For Rent
$3,300
Apr 22, 2012
Source: Agent Provided
ListingRemoved
$2,800
Jan 23, 2012
Source: Agent Provided
Listed For Rent
$2,800

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 14 Upland Rd

  • What is 14 Upland Rd estimated to be worth?
    Trulia's estimated value for 14 Upland Rd in Brookline, MA is $2,003,000.
  • 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.
  • What do residents say about the High Street Hill neighborhood?
    Residents describe the High Street Hill neighborhood in Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in High Street Hill, Brookline.
  • Does 14 Upland Rd have parking?
    Yes, 14 Upland Rd in Brookline, MA has on-site parking.

Homes for rent near 14 Upland Rd

Skip to last item
Skip to first item

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.
Skip to last item
  • Results are loading
Skip to first item