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516 Pleasant StWinthrop, MA 02152

For Sale

$1,499,000

Smart Buyer Rebate $7,495

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, (all outside the flood-zone by the way!!) 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.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

Listed by Amanda George

·

Lamacchia Realty, Inc.

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617-347-0699

Listed by Gerard George

·

Lamacchia Realty, Inc.

Last updated July 26, 2026

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Source: MLSPin #73541145

Listing Facts

  • TypeMulti-family
  • NeighborhoodDowntown Winthrop
  • Bedrooms5
  • Bathrooms3
  • Days on Prevu37
  • Taxes$12,555/year
  • Size2,889 sqft
  • Price per sqft$519

Amenities

  • Private Outdoor Space
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

07/22/2026
Price Decreased
$1,499,000
06/24/2026
Listed by Lamacchia Realty, Inc.
$1,600,000

Property Details for 516 Pleasant St

Association

Amenities

  • Community Features: Shopping, Pool, Park, Walk/Jog Trails, Conservation Area, Highway Access, House Of Worship, Marina, Public School

Exterior

Construction

  • Number Of Units Total: 3
  • Roof: Shingle
  • Stories: 3
  • Stories Total: 3
  • Year Built: 1900
  • Year Built Details: Approximate
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters, Professional Landscaping, Sprinkler System

Features

  • Fencing: Fenced/Enclosed, Fenced
  • Patio And Porch Features: Enclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed
  • Pool Features: In Ground
  • Road Frontage Type: Public
  • View: City View(s), City
  • Waterfront Features: Waterfront, Harbor, Harbor, Ocean, Direct Access, Frontage, 0 To 1/10 Mile To Beach
  • Waterfront: Yes

Measurements

  • Building Area Total: 2,889
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.20
  • Lot Size Area: 0
  • Lot Size Square Feet: 8,550
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:0047 B:0008 L:0000,1423226
  • Tax Annual Amount: $12,555.00
  • Tax Assessed Value: $1,127,000.00
  • Tax Year: 2026

Interior

Features

  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Wood, Tile, Varies

Measurements

  • Living Area: 2,889
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Interior Entry, Unfinished
  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 5
  • Rooms Total: 13

Other

General

  • Exclusions: Sellers Personal Property.

Parking

Parking

  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Off Street, Driveway
  • Parking Total: 4

Utilities

Equipment

  • Electric: 200+ Amp Service
  • Sewer: Public Sewer
  • Utilities: For Gas Range
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this multi-family home have?

There are 5 bedrooms and 3 bathrooms in this multi-family home at 516 Pleasant St.

Does this multi-family home have parking?

Yes, there are 4 parking spaces available for 516 Pleasant St.

What are the annual taxes for 516 Pleasant St?

Annual taxes for this multi-family home are estimated at $12,555.

How does 516 Pleasant St compare to other multi-family homes in Downtown Winthrop?

This multi-family home is listed 20% above the average price for multi-family homes in Downtown Winthrop and has been on the market for 17 less days than the typical home in this area.

What is the square footage on this multi-family home?

According to the MLS, this listing is 2,889 sqft.

516 Pleasant St is a 5-bedroom, 3-bath multi-family home for sale in Winthrop MA 02152. On Prevu for 37 days at $1,499,000. This includes a recent price decrease of $101,000. This residence features 2,889 square feet of living space, located in Downtown Winthrop. The median listing price for multi-family homes in this area is $800,000. Property amenities include private outdoor space, parking, and swimming pool. Explore more multi-family home listings in Winthrop Town.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.