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

30 Upland Rd
Brookline, MA 02445

High Street Hill
  • 6 Beds
  • 3 Baths
  • 3,619 sqft

$2,726,600

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $15,966/mo*
Refinance Your Home

$2,726,600

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $15,966/mo*
Refinance Your Home
6 Beds
3 Baths
3,619 sqft

Local Information

  • Map ViewExplore the area around 30 Upland Rd.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Circa 1879. Prime Pill Hill. Spectacular Victorian-era home offers over 3,600 sq ft of elegant living space. Gracious foyer, lustrous wood, ceiling medallion, sets the tone for interior which has beautiful architectural details. 3 fireplaces, high ceilings, bay windows, French doors, and handsome moldings. Modern eat-in kitchen leads to fenced backyard w/patio and plantings. Many windows allowing natural light. Lincoln School. Convenient to area amenities, Medical Area, and downtown Boston.
30 Upland Rd, Brookline, MA 02445 is a 6 bedroom, 3 bathroom, 3,619 sqft single-family home in High Street Hill, built in 1879. It last sold for $1,360,000 on Aug 15, 2012. It is currently off market. The Trulia Estimate is $2,726,600, with a rent estimate of $7,708/month.

Home Highlights

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

Home Details for 30 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1879Year Updated: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 3920 sqft

Price History for 30 Upland Rd

DatePriceEventSource
08/15/2012$1,360,000Sold
N/A
06/04/2012$1,395,000Listed For SaleAgent Provided
02/21/1992$223,000Sold
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
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Property Tax and Assessment

Year2025
Tax$22,002
Assessment$2,229,200
Home facts updated by county records

Comparable Sales for 30 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.06
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
236 Walnut St, Brookline, MA
0.24
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
43 Waverly St, Brookline, MA
0.33
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676
7 Dana St, Brookline, MA
0.40
Single-Family Home
$3,525,000
08/05/25
5
2.5
3,315
36 Allerton St, Brookline, MA
0.08
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
9 Greenough St, Brookline, MA
0.51
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
8 Wyman St, Jamaica Plain, MA
0.82
Single-Family Home
$1,520,000
07/25/25
5
3
3,198
50 Waverly St, Brookline, MA
0.34
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
157 Aspinwall Ave, Brookline, MA
0.50
Single-Family Home
$2,800,000
09/22/25
4
4
3,515

Nearby homes

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Assigned Schools

These are the assigned schools for 30 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

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Explore by feature - Pet Friendly

368 pet-friendly rentals in Brookline, MA

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Explore by feature - Outdoor Space

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Homes for sale near 30 Upland Rd

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Off Market Homes Near 30 Upland Rd

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