100 Upland Rd, Brookline, MA 02445
OFF MARKET

100 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 4 Baths
  • 5,940 sqft (on 0.25 acres)

$5,217,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $31,004/mo*
Refinance Your Home

$5,217,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $31,004/mo*
Refinance Your Home
6 Beds
4 Baths
5,940 sqft
(on 0.25 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Situated near Philbrick Square, this stately brick Colonial Revival-style house was designed by Peabody and Stearns in1889. Thoughtfully renovated, it offers updated five-zone hydro-air HVAC and a newer open kitchen with granite counters and stainless steel appliances. A wood paneled foyer with beautiful fireplace leads to an elegant, sun-filled living room and to a cozy front parlor with bay window with window seats. The 19'x16' dining room, separated by pocket doors from the 21'x19' living room, has a door that opens to a well landscaped fenced yard and stone patio. On the second floor, there is a master wing that includes bedroom, sitting area with fireplace, marble bathroom, office and closets. Additional rooms used as bedroom, exercise room, playroom and study with custom built shelves are on the third floor Queen Anne-style architectural details are found throughout the house in its oriel, oval and arched windows. Brookline Village and Lincoln School are close by.
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 & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 100 Upland Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 14
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick

Property Information

Year Built
Year Built: 1889Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 100 Upland Rd

DatePriceEventSource
07/30/2014$3,100,000Sold
N/A
04/22/2014$3,100,000ListingRemovedAgent Provided
04/03/2014$3,100,000PendingAgent Provided
04/01/2014$3,100,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$48,924
Assessment$4,956,800
Home facts updated by county records

Comparable Sales for 100 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27 Irving St, Brookline, MA
0.09
Single-Family Home
$3,220,000
05/28/25
7
4
5,244
14 Irving St, Brookline, MA
0.13
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.21
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
236 Walnut St, Brookline, MA
0.12
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
27 Walnut Pl, Brookline, MA
0.07
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
12 Zamora St, Boston, MA
0.61
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
212 Aspinwall Ave, Brookline, MA
0.63
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
7 Dana St, Brookline, MA
0.35
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
37 Stanton Rd, Brookline, MA
0.45
Single-Family Home
$2,970,000
06/11/25
5
3
2,676

Assigned Schools

These are the assigned schools for 100 Upland Rd.
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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

Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 100 Upland Rd

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Homes for rent near 100 Upland Rd

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Off Market Homes Near 100 Upland Rd

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Explore by feature

100 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 4 bathroom, 5,940 sqft single-family home built in 1889. 100 Upland Rd is located in High Street Hill, Brookline. This property is not currently available for sale. 100 Upland Rd was last sold on Jul 30, 2014 for $3,100,000. The current Trulia Estimate for 100 Upland Rd is $5,217,900.