516 Pleasant St Winthrop, MA ^$ 1,600,000

516 Pleasant St

^$ 1,600,000

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Recently Listed

516 Pleasant St

Winthrop, MA, 02152

^$ 1,600,000

Bedrooms5 Baths3.0 Sq 2,889

Monthly Estimate*

^$ 10,103

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Multi-Family Home for sale in Winthrop, MA

for $1,600,000 with 5 bedrooms and 3 full baths. This 2,889 square foot home was built in 1900 on a lot size of 0.2.

Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture. Many updates include replacement windows, mass-save insulation, professional landscaping and irrigation, mini-splits, replacement chimney liner, hunter-douglas shades, front porch replacement, and more. Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

Multi-Family Active

Price

^$ 1,600,000

Bedrooms

Full Bath

Property Type

Multi-Family

Taxes

^$ 12,555

Style

Multi Family

Lot Size

0.2

Year Built

1900

Town/City

Winthrop

County/Region

Suffolk

MLS | Web ID

73541145

List By

Amanda George

Listing Agent

Lamacchia Realty, Inc.

Broker

Affordability Calculator

$11,149

Per Month

Monthly Principal & Interest: $10,103
Monthly Property Taxes: $1,046
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% 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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Trends

Multi-family listings in Winthrop, MA

Average List Price ^$1,513,444

Percent of Sale Price 5%

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
6/24/2026	$1,600,000		Listed Price

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516 Pleasant St, Winthrop, MA, 02152 is a Multi-Family Home for sale at $1,600,000 with 2,889 sqft and a lot size of 0.2. 516 Pleasant St has 5 bedrooms, 3.0 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 6.49% 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 7/8/2026.

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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516 Pleasant St

Multi-Family Home for sale in Winthrop, MA

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