SOLD APR 15, 2026

Sold on Apr 2026

$1,175,000

•

4,062

sq ft

22 Upland Rd, Winthrop, MA 02152

Track this home’s value and nearby sales activity

About this home

In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, one off street parking space, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,

Multi-familyProperty Type

1900Year Built

3,894 sq ftLot Size

$289Price/Sq.Ft.

2 spacesParking

Listed by Mary Ann Cash • Charlesgate Realty Group, llc

Bought with Riode Jean Felix • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #73473241

Redfin Estimate

$1,230,453

$55K since sold in April 2026$17K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.8% higher than the average sale price ($1.07M) of 6 comparable homes.

SOLD JUL 31, 2026
$1,250,000
A
7 beds3 baths3,989 sq ft
22 Adams St, Winthrop, MA 02152
SOLD JUL 24, 2026
$1,280,000
B
9 beds3 baths3,621 sq ft
117 Revere St, Winthrop, MA 02152
SOLD NOV 25, 2025
$970,000
C
6 beds3.5 baths3,205 sq ft
212-214 Bradstreet Ave, Revere, MA 02151
SOLD JUN 25, 2026
$952,500
D
7 beds4 baths2,922 sq ft
38 Endicott Ave, Revere, MA 02151
SOLD DEC 18, 2025
$720,000
E
5 beds3.5 baths2,475 sq ft
9 Marshall St, Winthrop, MA 02152
SOLD MAR 31, 2026
$1,260,000
F
8 beds3 baths3,708 sq ft
37 Trident Ave, Winthrop, MA 02152

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Market trends in 02152, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.2%

+0.5% MoM

Median sale price

$620K

$21K MoM

Avg. days on market

38d

7 days MoM

Recently sold homes

9 MoM

New listings for sale

$539,000
1 bed1 bath1,368 sq ft
60 Hermon St #3, Winthrop, MA 02152
OPEN TODAY, 2PM TO 4PM
$649,000
3 beds1.5 baths1,200 sq ft
84 Tafts Ave, Winthrop, MA 02152
OPEN TODAY, 11AM TO 1PM
$739,000
3 beds2 baths1,428 sq ft
8 Siren St, Winthrop, MA 02152
OPEN TODAY, 11AM TO 12:30PM
$710,000
4 beds2 baths1,193 sq ft
542 Shirley St, Winthrop, MA 02152
OPEN TODAY, 12PM TO 2PM
$419,900
1 bed1 bath525 sq ft
22 Pauline St #5, Winthrop, MA 02152
OPEN TODAY, 12PM TO 2PM
$399,900
1 bed1 bath500 sq ft
22 Pauline St #3, Winthrop, MA 02152
OPEN TODAY, 11AM TO 1PM
$865,000
2 beds2.5 baths1,806 sq ft
1001 Shirley St #2, Winthrop, MA 02152
OPEN SUN, 12PM TO 1:30PM
$998,900
6 beds2.5 baths3,263 sq ft
217 Pleasant St, Winthrop, MA 02152
OPEN SUN, 11AM TO 12:30PM
$479,900
2 beds1 bath1,056 sq ft
2 Edgar Ter #3, Winthrop, MA 02152
OPEN TODAY, 11:30AM TO 12:30PM
$758,000
3 beds2.5 baths1,800 sq ft
189 Shirley St #1, Winthrop, MA 02152
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Sale and tax history for 22 Upland Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$7,572 (−4.9%)

$287,700 + $420,000

$707,700

2022

$7,962 (+2.2%)

$257,000 + $420,000

$677,000

2021

$7,791 (+9.6%)

$229,400 + $385,000

$614,400

2020

$7,108 (+4.1%)

$229,400 + $333,800

$563,200

2019

$6,830 (+1.6%)

$211,400 + $306,800

$518,200

2018

$6,725 (+7.9%)

$181,500 + $293,400

$474,900

2017

$6,235 (+5.9%)

$160,900 + $271,800

$432,700

2016

$5,890 (+9.8%)

$139,900 + $243,300

$383,200

2014

$5,363 (+1.5%)

$126,300 + $217,900

$344,200

2013

$5,284 (+2.9%)

$126,300 + $228,100

$354,400

2012

$5,135 (+7.1%)

$126,300 + $228,100

$354,400

2011

$4,796 (+2.3%)

$132,600 + $214,900

$347,500

2010

$4,690 (+14.8%)

$136,100 + $233,200

$369,300

2009

$4,086

$177,900 + $231,900

$409,800

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

3,920 Sq. Ft.

Year renovated

—

Sq. Ft.

4,062

Year built

1900

Style

Multi-Family (2-4 Unit)

County

Suffolk County

APN

1425125

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Open Parking
Open Parking Spaces: 2
Parking Spaces: 2
Parking Features: Paved Drive, Off Street, On Street, Paved

Interior

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1

Basement Information
Basement: Full, Interior Entry, Sump Pump, Concrete

Laundry Information
Laundry Features: Washer Hookup, Dryer Hookup, Gas Dryer Hookup, Electric Dryer Hookup

Appliances
Appliances: Oven, Dishwasher, Disposal, Range, Refrigerator, Microwave, Washer, Dryer

Interior Features
# of Rooms (Total): 17
Flooring: Tile, Hardwood
Interior Features: Ceiling Fan(s), Bathroom With Tub & Shower, Pantry, Living Room, Dining Room, Kitchen, Laundry Room, Office/Den, Sunroom

Unit #1 Information
# of Levels: 1
# of Floors: 1
Lease: N

Unit #2 Information
# of Levels: 1
# of Floors: 2
Lease: N

Unit #3 Information
# of Levels: 2
# of Floors: 2
Lease: N

Exterior

Building Information
Building Area (Total): 4,062
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Stories (Total): 4
Year Built Source: Public Records
Year Built Details: Approximate,Renovated Since
Color: Blue

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck, Patio
Exterior Features: Balcony/Deck

Property Information
PropertySubType: 3 Family
Above Grade Finished Area: 4062
Levels: 4
Has Waterview
Ocean

Lot Information
Lot Size (Acres): 0.09
Waterfront Features: Ocean, 0 to 1/10 Mile To Beach

Financial

Tax Information
Tax Annual Amount: $9,583
Tax Year: 2026

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, for Electric Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, Common, Individually Metered

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Hot Water, Natural Gas
Heating Units: 3
Cooling: Window Unit(s)

Location

Location Information
Directions: GPS
UnparsedAddress: 22 Upland Road, Winthrop MA 02152

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Park, Walk/Jog Trails, Golf, Laundromat, House of Worship, Marina, Public School, T-Station

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 4,062
Stories: 2.0
Lot Size: 3,920 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1900
Year Renovated: —
County: Suffolk County
APN: 1425125

Home facts updated by county records on Jul 20, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

William P. Gorman/Fort Banks Elementary School

Public PreK-2 • Assigned • 0.3mi

Winthrop Middle School

Public 6-8 • Assigned • 0.6mi

8/10

Winthrop Senior High School

Public 9-12 • Assigned • 0.6mi

5/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 95° expected this year, 14 days in 30 years

6/10 Wind Factor

65% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winthrop, MA • 02152

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.17M – $1.42M

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New listings for sale in 02152

$539,000

1 bed1 bath1,368 sq ft

60 Hermon St #3, Winthrop, MA 02152

OPEN TODAY, 2PM TO 4PM

$649,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, Winthrop, MA 02152

OPEN TODAY, 11AM TO 1PM

$739,000

3 beds2 baths1,428 sq ft

8 Siren St, Winthrop, MA 02152

OPEN TODAY, 11AM TO 12:30PM

$710,000

4 beds2 baths1,193 sq ft

542 Shirley St, Winthrop, MA 02152

OPEN TODAY, 12PM TO 2PM

$419,900

1 bed1 bath525 sq ft

22 Pauline St #5, Winthrop, MA 02152

OPEN TODAY, 12PM TO 2PM

$399,900

1 bed1 bath500 sq ft

22 Pauline St #3, Winthrop, MA 02152

OPEN TODAY, 11AM TO 1PM

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

OPEN SUN, 12PM TO 1:30PM

$998,900

6 beds2.5 baths3,263 sq ft

217 Pleasant St, Winthrop, MA 02152

OPEN SUN, 11AM TO 12:30PM

$479,900

2 beds1 bath1,056 sq ft

2 Edgar Ter #3, Winthrop, MA 02152

Home values near 22 Upland Rd

Data from public records.

Address	Redfin Estimate
57 Upland Road, Winthrop, MA 2 Beds \| 2 Baths \| 1652 Sq. Ft.	$776,079
2-4 Upland Road, Winthrop, MA 6 Beds \| 3 Baths \| 3701 Sq. Ft.	$1,232,926

Address	Redfin Estimate
41 Upland Road, Winthrop, MA 5 Beds \| 2.5 Baths \| 2741 Sq. Ft.	$1,006,978
18 Upland Road, Winthrop, MA 8 Beds \| 2 Baths \| 3505 Sq. Ft.	$1,053,832

Address	Redfin Estimate
35 Upland Road, Winthrop, MA 2 Beds \| 2 Baths \| 1960 Sq. Ft.	$819,821
28-32 Upland Road, Winthrop, MA 4 Beds \| 3 Baths \| 2940 Sq. Ft.	$1,016,690

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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