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

84 Upland Rd
Brookline, MA 02445

High Street Hill
  • 5 Beds
  • 3.5 Baths
  • 4,374 sqft (on 0.32 acres)

$4,023,400

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $23,523/mo*
Refinance Your Home

$4,023,400

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $23,523/mo*
Refinance Your Home
5 Beds
3.5 Baths
4,374 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 84 Upland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Circa 1885, built by important Boston architects Ware & Van Brunt, this historic property is prominently located on Pill Hill across from Philbrick Green. With over 4,370 sq ft of elegant living space, there are 10 rooms, 5 bedrooms, 3 and one-half bathrooms, & 5 fireplaces. As you enter, the gracious foyer leads to handsome rooms w/exquisite period detail, high ceilings, built-in cabinetry, beautiful wood flooring, & intricate moldings. The layout is well-suited for entertaining. The large eat-in kitchen, w/ granite counters, ss appliances, center island, has access to both a deck & patio. There are 3 bedrooms on the 2nd floor, one w/vaulted ceiling, & 2 bedrooms plus & office on the 3rd floor. There have been renovations over the years, yet many of the fine period detail reminiscent of the era remain intact. The grounds are equally impressive w/spectacular private front & backyards. Amenities: c/a & 2-car garage. Set in a coveted Brookline location, this property is truly special.
84 Upland Rd, Brookline, MA 02445 is a 5 bedroom, 4 bathroom, 4,374 sqft single-family home in High Street Hill, built in 1880. It last sold for $2,860,000 on Sep 15, 2020. It is currently off market. The Trulia Estimate is $4,023,400, with a rent estimate of $8,301/month.

Home Highlights

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

Home Details for 84 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11Wet BarCeiling Fan
Heating & Cooling
Heating: Baseboard, Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: BrickPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1880Year Updated: 1972
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price History for 84 Upland Rd

DatePriceEventSource
09/15/2020$2,860,000Sold
N/A
08/17/2020$3,195,000PendingAgent Provided
07/14/2020$3,195,000Listed For SaleAgent 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$33,041
Assessment$3,347,600
Home facts updated by county records

Comparable Sales for 84 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.15
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
36 Allerton St, Brookline, MA
0.20
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
27 Walnut Pl, Brookline, MA
0.10
Single-Family Home
$3,950,000
08/01/25
4
3.5
4,232
236 Walnut St, Brookline, MA
0.15
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
12 Zamora St, Boston, MA
0.57
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
7 Dana St, Brookline, MA
0.39
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
209 High St, Brookline, MA
0.22
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
115 Clark Rd, Brookline, MA
0.64
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182
71 Greenough St, Brookline, MA
0.52
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
213 Gardner Rd, Brookline, MA
0.74
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507

Nearby homes

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Assigned Schools

These are the assigned schools for 84 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

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

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Explore by feature - Outdoor Space

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Homes for sale near 84 Upland Rd

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Off Market Homes Near 84 Upland Rd

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