22 Upland Road Winthrop, MA ^$ 1,250,000

22 Upland Road

^$ 1,250,000

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22 Upland Road

Winthrop, MA, 02152

^$ 1,250,000

Bedrooms6 Baths3.1 Sq 4,062

Monthly Estimate*

^$ 7,696

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Multi-Family Home for sale in Winthrop, MA

for $1,250,000 with 6 bedrooms and 3 full baths, 1 half bath. This 4,062 square foot home was built in 1900 on a lot size of 0.09.

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,

Multi-Family Active

Price

^$ 1,250,000

Bedrooms

Full Bath

Half Bath

Property Type

Multi-Family

Taxes

^$ 9,583

Style

3 Family

Lot Size

0.09

Year Built

1900

Town/City

Winthrop

County/Region

Suffolk

MLS | Web ID

73473241

List By

Mary Ann Cash

Listing Agent

Charlesgate Realty Group, Llc

Broker

Affordability Calculator

$8,495

Per Month

Monthly Principal & Interest: $7,696
Monthly Property Taxes: $799
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Multi-family listings in Winthrop, MA

Average List Price ^$1,294,971

Percent of Sale Price 4%

About Winthrop, MA

17,967 Population

-2% Since 2002

^$65,929 Median Income

46.08 Median Age

21% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
2/1/2026	$1,250,000		Listed Price

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22 Upland Road, Winthrop, MA, 02152 is a Multi-Family Home for sale at $1,250,000 with 4,062 sqft and a lot size of 0.09. 22 Upland Road has 6 bedrooms, 3.1 baths, and was built in 1900. The property's zip code is 02152 which is in Winthrop, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 2/2/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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22 Upland Road

Multi-Family Home for sale in Winthrop, MA

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