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

14 Upland Rd
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 1 Bath
  • 1,143 sqft

$2,082,000

Trulia Estimate
as of Jul 11, 2026
Est. Refi. Payment $12,209/mo*
Refinance Your Home

$2,082,000

Trulia Estimate
as of Jul 11, 2026
Est. Refi. Payment $12,209/mo*
Refinance Your Home
3 Beds
1 Bath
1,143 sqft

Local Information

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

Description

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. It is currently off market. The Trulia Estimate is $2,082,000, with a rent estimate of $3,945/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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

Price History for 14 Upland Rd

DatePriceEventSource
06/17/2025$3,300ListingRemovedZillow Rentals
06/15/2025$3,300Listed For RentZillow Rentals
04/22/2012$2,800ListingRemovedAgent Provided
01/23/2012$2,800Listed For RentAgent Provided

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$15,579
Assessment$1,578,400
Home facts updated by county records

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
33 Pond Ave #1207, Brookline, MA
0.19
Apartment
$880,000
10/15/25
2
2
1,300
77 Pond Ave #308, Brookline, MA
0.19
Apartment
$450,000
04/28/26
1
1
720
70 Day St, Jamaica Plain, MA
0.69
Apartment
$697,000
05/18/26
3
1
1,000
36 Saint Paul St #B, Brookline, MA
0.54
Apartment
$470,000
06/12/26
2
1
-
441 Washington St #5, Brookline, MA
0.47
Apartment
$999,999
06/01/26
3
2
1,541
28 Saint Paul St #1, Brookline, MA
0.51
Apartment
$663,000
08/12/25
2
1
715
20 Saint Paul St #2, Brookline, MA
0.51
Apartment
$400,000
10/14/25
2
1
703
135 Calumet St #2, Roxbury, MA
0.80
Apartment
$685,000
10/24/25
3
1
999
49 Harvard Ave #4, Brookline, MA
0.50
Apartment
$974,000
06/15/26
1
1
700
Home facts updated by county records

Nearby homes

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Assigned Schools

These are the assigned schools for 14 Upland Rd.
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

365 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

77 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

557 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

80 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

940 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 14 Upland Rd

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Off Market Homes Near 14 Upland Rd

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