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

$3,929,500

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 4,374 sqft (on 0.32 acres)

84 Upland Rd, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $24,435/mo*
Refinance Your Home
Currently Off Market - Sold Sep 15, 2020 for $2,860,000

Home Value

Trulia Estimate
$3.93M
Since last month
Increased$34K (+0.9%)
Since last year
Increased$111K (+2.9%)
Since last sale
Increased$1M (+36.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +70% in the last 10 years
MonthEstimated value
2026
October 2026$3.91M
September 2026$3.88M
August 2026$3.91M
July 2026$4.04M
June 2026$4.02M
May 2026$4.02M
April 2026$4.03M
March 2026$3.98M
February 2026$3.85M
January 2026$3.73M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
36 Allerton St, Brookline, MA
0.20
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
236 Walnut St, Brookline, MA
0.15
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
54 Clark Rd, Brookline, MA
0.51
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
12 Zamora St, Boston, MA
0.57
Single-Family Home
$2,250,000
12/16/25
6
3.5
4,800
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
16 Kennard Rd, Brookline, MA
0.38
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
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
43 Waverly St, Brookline, MA
0.37
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
94 Upland Rd, Brookline, MA 02445
0.02
$3,006,700
8
4
4,719
Off Market
56 Walnut Pl, Brookline, MA 02445
0.03
$3,801,800
4
5
4,022
Off Market
78 Upland Rd, Brookline, MA 02445
0.03
$5,905,100
6
5.5
6,767
Off Market
100 Upland Rd, Brookline, MA 02445
0.04
$5,287,800
6
4
5,940
Off Market
Walnut Pl, Brookline, MA 02445
0.04
-
-
-
-
Off Market
71 Upland Rd, Brookline, MA 02445
0.04
$2,129,700
4
3
1,696
Off Market
76 Walnut Pl, Brookline, MA 02445
0.04
$8,091,500
6
7
8,000
Off Market
76 Walnut Pl #2, Brookline, MA 02445
0.04
-
Studio
-
-
Off Market
70 Upland Rd, Brookline, MA 02445
0.05
$3,764,900
5
6
5,312
Off Market
108 Upland Rd, Brookline, MA 02445
0.06
$4,537,400
7
5
6,359
Off Market
65 Upland Rd, Brookline, MA 02445
0.06
$3,405,600
6
4
4,101
Off Market
62 Upland Rd, Brookline, MA 02445
0.06
$3,489,200
5
4
3,604
Off Market
107 Upland Rd, Brookline, MA 02445
0.06
$3,655,800
5
4
4,746
Off Market
67 Walnut Pl, Brookline, MA 02445
0.06
$5,761,100
6
5
6,338
Off Market
57 Upland Rd, Brookline, MA 02445
0.06
$5,494,700
6
6
6,775
Off Market
123 High St, Brookline, MA 02445
0.07
$4,079,100
8
6
5,312
Off Market
107 High St, Brookline, MA 02445
0.07
$1,791,400
3
3
2,350
Off Market
111 High St, Brookline, MA 02445
0.07
$2,049,400
9
5
4,927
Off Market
107 High St #6, Brookline, MA 02445
0.07
-
1
1
9,999
Off Market
35 Walnut Pl, Brookline, MA 02445
0.07
$7,150,600
7
6
5,549
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1880
0.32 acre lot
4,374 sqft
$898/sqft
Garage

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,929,500.

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 and Tax history

DateEventPrice
Sep 15, 2020
Source: N/A
Sold
$2,860,000
Aug 17, 2020
Source: Agent Provided
Pending
$3,195,000
Jul 14, 2020
Source: Agent Provided
Listed For Sale
$3,195,000

Market trends in Brookline

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.19M
$50.67KMoM
Sale-to-List Price
98.7%
0.6%MoM
Price per sq ft
$806
$3MoM
Available listings
227
39MoM
Sourced by Trulia Market Trends

Around this home

Neighborhood Overview

High Street Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about High Street Hill

This October

Trick-or-Treat Score

Built from what locals say about High Street Hill.
  • 98% say there are sidewalks
  • 63% say there's holiday spirit
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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

Frequently asked questions about 84 Upland Rd

  • What is 84 Upland Rd estimated to be worth?
    Trulia's estimated value for 84 Upland Rd in Brookline, MA is $3,929,500.
  • What is the price history for 84 Upland Rd?
    84 Upland Rd in Brookline, MA last sold for $2,860,000 in September 2020.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.19M. That is down $50.67K from the prior month.
  • Does 84 Upland Rd have air conditioning?
    Yes, 84 Upland Rd in Brookline, MA has air conditioning.
  • How big is the lot at 84 Upland Rd?
    The lot at 84 Upland Rd in Brookline, MA is about 0.32 acres (13,939 sq ft).

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Off Market Homes Near 84 Upland Rd

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