51 Upland Rd, Brookline, MA 02445
OFF MARKET

51 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 4 Baths
  • 4,052 sqft

$3,422,200

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $17,423/mo*
Refinance Your Home

$3,422,200

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $17,423/mo*
Refinance Your Home
6 Beds
4 Baths
4,052 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

A chance to experience the magic and serenity of Pill Hill living overlooking the pastoral beauty of Philbrick Green. With warm and inviting rooms this turn of the century home features multiple fireplaces, beautiful period moldings throughout, & original 12-pane windows. Updated kitchen with 6-burner Viking stove, hand-painted Delft tiles and cozy fireplace. Beautiful garden, stone patio and porch offer wonderful outdoor living space. Steps from T, Longwood Medical Center, and Brookline Village
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 51 Upland Rd

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1896Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 8746 sqft

Price History for 51 Upland Rd

DatePriceEventSource
06/08/2011$1,700,000Sold
N/A
04/12/2011$1,695,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$30,038
Assessment$3,043,400
Home facts updated by county records

Comparable Sales for 51 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.07
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
27 Irving St, Brookline, MA
0.03
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
36 Allerton St, Brookline, MA
0.14
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
19 Edgehill Rd, Brookline, MA
0.16
Single-Family Home
$3,765,000
05/28/25
5
4
3,538
129 Walnut St, Brookline, MA
0.12
Single-Family Home
$1,150,000
06/04/25
6
2.5
3,784
236 Walnut St, Brookline, MA
0.18
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.60
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
212 Aspinwall Ave, Brookline, MA
0.56
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
209 High St, Brookline, MA
0.30
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
9 Greenough St, Brookline, MA
0.51
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104

Assigned Schools

These are the assigned schools for 51 Upland Rd.
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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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Homes for sale near 51 Upland Rd

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Off Market Homes Near 51 Upland Rd

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Homes for rent near 51 Upland Rd

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51 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 4 bathroom, 4,052 sqft single-family home built in 1896. 51 Upland Rd is located in High Street Hill, Brookline. This property is not currently available for sale. 51 Upland Rd was last sold on Jun 8, 2011 for $1,700,000. The current Trulia Estimate for 51 Upland Rd is $3,422,200.