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$1,250,000

  • For Sale
  • Active
  • Multi-Family
  • 3 Units
  • 6 Total Beds
  • 0.09 Acres
  • Updated 4 days ago
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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, two off street parking spaces, 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,

Full Property Details for 22 Upland Rd

General

  • Price: $1,250,000
  • Taxes: $9,583 (2026)
  • Status: Active
  • Type: Multi-Family
  • MLS ID: 73473241
  • Updated: 2/5/2026
  • Added to Site: 9 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 6

Parking

  • Parking Features: Paved Drive, Off Street, Tandem, On Street, Paved

Location

  • County: Suffolk

Structural Information

  • Basement: Yes
  • Stories/Levels: 4
  • Square Feet: 4,062
  • Year Built: 1900

Lot Features

  • Lot Size (Acres): 0.09

Financial Considerations

  • Tax Amount: $9,583
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: All information is as of the entry date and is subject to change. Buyer/Buyer's Agent to verify all information provided. Property is being sold in "as is" condition. Appliances are gifts. Unit 2 will be delivered vacant. Photos and floor plan are of Unit 1.
  • Property ID: 1425125

Listed by Charlesgate Realty Group, llc, Mary Ann Cash

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Listing agent

— 22 Upland Rd —

  • Mary Ann Cash

    Charlesgate Realty Group, llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 22 Upland Rd

School District:Winthrop School District
NameGradesDistance
William P. Gorman/Fort Banks Elementary School
101 Kennedy Drive, Winthrop, MA 02152
PK-20.3 mi
Arthur T. Cummings Elementary School
40 Hermon Street, Winthrop, MA 02152
3-50.9 mi
Winthrop Middle School, Winthrop, MA
60 Payson Street, Winthrop, MA 02152
6-80.6 mi
Winthrop Sr High School
400 Main Street, Winthrop, MA 02152
9-120.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 22 Upland Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/01/2026
Listed
$1,250,000
375.29%
MLS
3/31/1988
Sold
$263,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 22 Upland Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,457
1%
$722,600
2%
2024
$7,369
-3%
$707,200
—
2023
$7,572
-5%
$707,700
5%
2022
$7,962
2%
$677,000
10%
2021
$7,791
10%
$614,400
9%
2020
$7,108
4%
$563,200
9%
2019
$6,830
2%
$518,200
9%
2018
$6,725
8%
$474,900
10%
2017
$6,235
6%
$432,700
13%
2016
$5,890
14%
$383,200
7%
2015
$5,145
-4%
$358,800
4%
2014
$5,363
—
$344,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 22 Upland Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Charlesgate Realty Group, llc, Mary Ann Cash

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22 Upland Road, Winthrop, MA 02152 (MLS# 73473241) is a Multi-Family property with 3 units containing 6 bedrooms, 3 full bathrooms and 1 partial bathroom. 22 Upland Road is currently listed for $1,250,000 and was received on February 01, 2026. Want to learn more about 22 Upland Road? Do you have questions about finding other Multi-Family real estate for sale in Winthrop? You can browse all Winthrop real estate or contact a Coldwell Banker agent to request more information.

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