14 Upland Rd #2A, Brookline, MA 02445
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Property image
OFF MARKET

14 Upland Rd #2A
Brookline, MA 02445

High Street Hill
  • 3 Beds
  • 1 Bath
  • 9,999 sqft

$1,362,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $8,017/mo*
Refinance Your Home

$1,362,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $8,017/mo*
Refinance Your Home
3 Beds
1 Bath
9,999 sqft

Local Information

  • Map ViewExplore the area around 14 Upland Rd #2A.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

** Showings Sunday 5/15 at 1:30-1:50 ** Brookline Sun drenched 3 bed with OFF STREET PARKING and free laundry in building within a mile to Coolidge Corner. The unit has a spacious living-room, kitchen, and dining room! Kitchen has dishwasher, gas stove, ample counter space, and good cabinet space. Each room are evenly sized with amazing natural light shining through during the day. Painted with custom colors, along with hardwood floors throughout. There is an amazing private deck on the second level facing the street ! Along with this is another private back deck facing the back yard. Lastly, you will find a shared back yard where you can have ample space space for wonderful gatherings. The unit also includes 1 parking space tandem within the driveway shared with floor 1 tenant. Move in cost is broker fee, first month, last month, and security deposit ! *Photos are from #1 previous tenancy* Units have identical footprints.

Onwer pays for water, pets are negotiable, move in cost if Broker fee, first month, last month, and security deposit
14 Upland Rd #2A, Brookline, MA 02445 is a 3 bedroom, 1 bathroom, 9,999 sqft townhouse in High Street Hill. More recently, it was listed as a rental in May 2022 with an asking price of $3,300 per month. That rental listing was removed on May 24, 2022. It is currently off market. The Trulia Estimate is $1,362,800, with a rent estimate of $3,648/month.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 14 Upland Rd #2A

Property Information

Property Type / Style
Property Type: Townhouse

Interior Features

Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Parking & Garage
Parking: Off Street

Additional Information

On Site Laundry Available

Price History for 14 Upland Rd #2A

DatePriceEventSource
05/24/2022ListingRemovedZillow Rental Manager
05/12/2022$3,300Listed For RentZillow Rental Manager

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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Comparable Sales for 14 Upland Rd #2A

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 White Pl #3, Brookline, MA
0.10
Townhouse
$1,125,000
09/25/25
3
2
1,345
111 Davis Ave #1, Brookline, MA
0.27
Townhouse
$1,200,000
08/04/25
3
2
1,415
81 Glen Rd #S2, Brookline, MA
0.28
Townhouse
$967,000
04/28/26
3
2
1,340
7 Eugene Cir #B, Jamaica Plain, MA
0.54
Townhouse
$650,000
04/27/26
2
1
1,461
100 Lawn St, Roxbury, MA
0.61
Townhouse
$471,492
04/24/26
2
1
1,266
33 Evergreen St #2, Jamaica Plain, MA
0.59
Townhouse
$1,595,000
09/02/25
3
3
2,351
33 Evergreen St #1, Boston, MA
0.59
Townhouse
$1,560,000
11/14/25
3
3
2,222
31 Evergreen St #2, Jamaica Plain, MA
0.60
Townhouse
$1,602,975
10/06/25
3
3
2,261
51 Rawson Rd #51, Brookline, MA
0.72
Townhouse
$2,750,000
07/22/25
3
2.5
3,848
31 Evergreen St #1, Jamaica Plain, MA
0.60
Townhouse
$1,510,000
11/10/25
3
3
2,064

Nearby homes

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Assigned Schools

These are the assigned schools for 14 Upland Rd #2A.
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

561 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

82 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

947 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 #2A

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Off Market Homes Near 14 Upland Rd #2A

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