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Active

516 Pleasant St, Winthrop MA 02152

$1,600,000

Estimated $3,641/month Calculator

Multi Family

Total Units: 3

Price Per Unit: $533,333.33

Total Rent: 0/year

Estimated CAP Rate:

5 Bedrooms

Baths

2889

Total Parking: 4

8,550 (0.20)

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. 3 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!

This home has been viewed 5 times

Last Checked: June 25th, 2026 at 9:38am (Source: MLS PIN #73541145)

Gross Income: $0

Gross Expenses: $12,555

Net Income Calc: $12,555

Waterfront

Water Views

Annual Expenses for 516 Pleasant St, Winthrop MA 02152

Total Gross Expenses (Calculated)$12,555/year

APOD AvailableNo

Heating

Electricity

Water

Gas

Insurance

Sewer

Trash Removal

Repair & Maintenance

Management

Miscellaneous

Real Estate Tax12555

Annual Income & Unit Breakdown for 516 Pleasant St, Winthrop MA 02152

Total Gross Income (Calculated)$0

Unit 1

Rental Income$0

LeaseN

Bedrooms1

Bathrooms1 Full

Floor1

Levels in Unit1

Rent Includes

Unit 2

Rental Income$0

LeaseN

Bedrooms2

Bathrooms1 Full

Floor2

Levels in Unit1

Rent Includes

Unit 3

Rental Income$0

LeaseN

Bedrooms1

Bathrooms1 Full

Floor3

Levels in Unit1

Rent Includes

General Information for 516 Pleasant St, Winthrop MA 02152

Listing ID73541145

Property TypeMulti Family

Price1600000 ($553.82/SqFt)

StyleMulti Family

CityWinthrop

CountySuffolk

Neighborhood(s)

Approximate Living Area Total2889

Approximate Lot Size (Acres)0.2

Total Parking4

Garage Parking0

Year Built1900

Year Built SourcePublic Records

Year Built DetailsApproximate

WaterPublic

SewerPublic Sewer

Electric220 Volts

Hot Water

Roof MaterialAsphalt/fiberglass Shingles

BasementFull

Construction MaterialsFrame

Lot Features

Foundation Description

Accessible Features

Outdoor SpaceCovered

Zoningrh6

Water ViewsYes

Water Views FeaturesBay

Waterfront1

Waterfront FeaturesRiver

Terms

Disclosures for 516 Pleasant St, Winthrop MA 02152

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

ExclusionsLighting In Loft Area

Financial Data Source

Total Gross Expenses By Broker

Total Gross Income By Broker

Total Net Income By Broker

Short Sale / Forclosure (Bank Owned)

Compensation Based On

Financial Information for 516 Pleasant St, Winthrop MA 02152

Real Estate Taxes12555

Tax Year2026

Assessed Value$1,127,000

Financial Data Source

Total Gross Expenses By Broker

BostonRealEstate.com Gross Expenses

Total Gross Income By Broker

BostonRealEstate.com Gross Income

Total Net Income By Broker

BostonRealEstate.com Gross NOI

CAP Rate (based on Broker info)

Location Information for 516 Pleasant St, Winthrop MA 02152

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 516 Pleasant St, Winthrop MA 02152

Agent

Name: Amanda George

Office

Name: Lamacchia Realty, Inc.

Phone: 781-917-0491

Team Members

Name: Amanda George

Payment Calculator

, Interest

Property Taxes 1046.25

Principal & Interest 9858.69

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Lamacchia Realty, Inc.

Amanda George

Agent Phone

Office Phone

(781) 917-0491

Text Agent Call Agent Call Office

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    [description] => 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. 3 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!
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    [unparsed] => 516 Pleasant St, Winthrop MA 02152
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EXIT

39 More Photos

Active

516 Pleasant St, Winthrop MA 02152

$1,600,000

Annual Expenses for 516 Pleasant St, Winthrop MA 02152

Annual Income & Unit Breakdown for 516 Pleasant St, Winthrop MA 02152

General Information for 516 Pleasant St, Winthrop MA 02152

Disclosures for 516 Pleasant St, Winthrop MA 02152

Financial Information for 516 Pleasant St, Winthrop MA 02152

Location Information for 516 Pleasant St, Winthrop MA 02152

Contact Information for 516 Pleasant St, Winthrop MA 02152

Agent

Office

Team Members

Payment Calculator

Exclusive Listing Agent

Lamacchia Realty, Inc.

Amanda George