22 Oakland Rd, Brookline, MA 02445
OFF MARKET

$3,626,800

Trulia Estimate
  • 9 Beds
  • 5 Baths
  • 5,200 sqft (on 0.75 acres)

22 Oakland Rd, Brookline, MA 02445

High Street Hill
Est. Refi. Payment $22,170/mo*
Refinance Your Home
Currently Off Market - Sold Jan 5, 1988 for $550,000

Home Value

Trulia Estimate
$3.63M
Since last month
Decreased$90K (-2.4%)
Since last year
Decreased$92K (-2.5%)
Since last sale
Increased$3M (+559.4%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$3.63M
August 2026$3.62M
July 2026$3.72M
June 2026$3.7M
May 2026$3.72M
April 2026$3.75M
March 2026$3.71M
February 2026$3.62M
January 2026$3.55M
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
16 Kennard Rd, Brookline, MA
0.24
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
371 Walnut St, Brookline, MA
0.34
Single-Family Home
$5,250,000
03/02/26
7
5.5
6,193
54 Clark Rd, Brookline, MA
0.38
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
14 Irving St, Brookline, MA
0.22
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
469 Walnut St, Brookline, MA
0.55
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
236 Walnut St, Brookline, MA
0.03
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
36 Allerton St, Brookline, MA
0.32
Single-Family Home
$4,250,000
12/08/25
5
4.5
4,072
213 Gardner Rd, Brookline, MA
0.61
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
21 Sargent Crossway, Brookline, MA
0.47
Single-Family Home
$7,030,000
04/03/26
5
6.5
5,772
115 Clark Rd, Brookline, MA
0.51
Single-Family Home
$3,400,000
03/06/26
4
4.5
4,182

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
236 Walnut St, Brookline, MA 02445
0.03
$2,750,000
4
3.5
3,963
Recently Sold
27 Walnut Pl, Brookline, MA 02445
0.04
$4,096,500
4
3.5
4,232
Off Market
4 Vogel Ter, Brookline, MA 02445
0.03
$2,493,400
5
2.5
2,616
Off Market
255 Walnut St #B, Brookline, MA 02445
0.07
$1,310,000
3
1.5
1,543
Recently Sold
255 Walnut St #C, Brookline, MA 02445
0.07
$1,481,800
4
2
2,533
Off Market
20 Rice St #2, Brookline, MA 02445
0.07
$740,000
3
1
978
Recently Sold
17 Milton Rd, Brookline, MA 02445
0.10
$2,548,500
12
5
4,911
Off Market
20 E Milton Rd #3, Brookline, MA 02445
0.11
$947,300
3
2
1,300
Off Market
8 Leverett St #4, Brookline, MA 02445
0.16
$1,275,000
2
2
1,320
Recently Sold
8 Leverett St #3, Brookline, MA 02445
0.16
$1,300,000
2
2
1,328
Recently Sold
11 E Milton Rd, Brookline, MA 02445
0.11
$2,342,000
12
3
4,515
Off Market
18-20 Roberts St, Brookline, MA 02445
0.11
-
18
12
8,280
Off Market

Local Information

  • Map ViewExplore the area around 22 Oakland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1810
0.75 acre lot
5,200 sqft
$697/sqft

About this House

A historic home in an historic district with great schools and transportation
22 Oakland Rd, Brookline, MA 02445 is a 9 bedroom, 5 bathroom, 5,200 sqft single-family home in High Street Hill, built in 1810. It last sold for $550,000 on Jan 5, 1988. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,626,800, with a rent estimate of $6,681/month.

Home Details for 22 Oakland Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 17Types of Rooms: Dining Room
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 4Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenLawn
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1810Year Updated: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.75 acres

Price and Tax history

DateEventPrice
Jan 5, 1988
Source: N/A
Sold
$550,000

Market trends in Brookline

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.24M
$23.33KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$811
$6MoM
Available listings
186
30MoM

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

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 22 Oakland Rd

  • What is 22 Oakland Rd estimated to be worth?
    Trulia's estimated value for 22 Oakland Rd in Brookline, MA is $3,626,800.
  • What is the price history for 22 Oakland Rd?
    22 Oakland Rd in Brookline, MA last sold for $550,000 in January 1988.
  • 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 $1.24M. That is up $23.33K from the prior month.
  • Does 22 Oakland Rd have laundry facilities?
    Yes, 22 Oakland Rd in Brookline, MA has in-unit laundry.
  • How big is the lot at 22 Oakland Rd?
    The lot at 22 Oakland Rd in Brookline, MA is about 0.75 acres (32,670 sq ft).

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Apartments for Rent

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Off Market Homes Near 22 Oakland Rd

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