27 Upland Rd, Brookline, MA 02445
OFF MARKET

27 Upland Rd
Brookline, MA 02445

High Street Hill
  • 5 Beds
  • 2 Baths
  • 1,656 sqft

$1,854,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,885/mo*
Refinance Your Home

$1,854,800

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,885/mo*
Refinance Your Home
5 Beds
2 Baths
1,656 sqft

Local Information

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

Description

Lovely Cape style home in prestigious sought after Brookline neighborhood on a corner lot. Spacious interior featuring an open floor plan and built-in shelves. Perfect for families or those seeking main floor living without stairs. Living space expansion potential in roomy unfinished basement. Ideal quiet location, walking distance to MBTA Green Line, elementary school, and Brookline Village shops. This is your opportunity to make this your perfect home in a special neighborhood where homes don't come on the market very often!
27 Upland Rd, Brookline, MA 02445 is a 5 bedroom, 2 bathroom, 1,656 sqft single-family home in High Street Hill, built in 1930. It last sold for $1,280,000 on Mar 27, 2020. It is currently off market. The Trulia Estimate is $1,854,800, with a rent estimate of $6,324/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, Other, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Concrete, Hardwood
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Wood
Parking & Garage
GarageParking Space: 1Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1930Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

Price History for 27 Upland Rd

DatePriceEventSource
03/27/2020$1,280,000Sold
N/A
02/16/2020$1,590,000PendingAgent Provided
01/29/2020$1,590,000PriceChange
Agent Provided
01/08/2020$1,650,000PriceChange
Agent Provided
12/19/2019$1,690,000Listed For SaleAgent Provided
09/02/1997$383,400Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$14,686
Assessment$1,487,900
Home facts updated by county records

Comparable Sales for 27 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.04
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
50 Waverly St, Brookline, MA
0.31
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
18 Cushing Rd, Brookline, MA
0.43
Single-Family Home
$1,351,000
01/23/26
2
2
1,230
14-14A Linden Pl, Brookline, MA
0.40
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
61 Toxteth St, Brookline, MA
0.54
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484
71 Highland Rd, Brookline, MA
0.27
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
36 Allerton St, Brookline, MA
0.10
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
209 High St, Brookline, MA
0.35
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
18 Eldora St, Roxbury, MA
0.56
Single-Family Home
$863,000
10/10/25
4
1.5
2,149
9 Greenough St, Brookline, MA
0.49
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104

Nearby homes

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

Assigned Schools

These are the assigned schools for 27 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

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

368 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

81 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

564 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 27 Upland Rd

Skip to last item
Skip to first item

Off Market Homes Near 27 Upland Rd

Skip to last item
Skip to first item