Listing Tools

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!

More Info

Basic Information

  • Mls StatusNew
  • Parcel Number M:0047 B:0008 L:0000,1423226

Tax Information

  • Tax Assessed Value $1,127,000
  • Tax Year 2026
  • Taxes$12,555

Parking

  • Open Parking YN Yes
  • Parking Features Off Street, Driveway
  • Parking Spaces4

Rooms

  • Bathroom3
  • Bathrooms Total Decimal 3
  • Bedrooms5
  • Full Bath3

Basic Information

  • List Price$1,600,000
  • MLS Number73541145
  • Modification Date06/24/2026
  • Property SubTypeMulti Family

Location

  • Address516 Pleasant Street
  • Building Number516
  • CountySuffolk
  • StateMA
  • StreetPleasant Street
  • TownWinthrop
  • Zip02152

Building

  • BasementFull, Interior Entry, Unfinished
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FireplaceYes
  • Fireplaces Total 1
  • FoundationOther
  • Levels 3
  • Patio And Porch Features Enclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed
  • Rooms13
  • Stories3
  • Units3
  • Utilities For Gas Range
  • Year Built1900
  • Year Built Details Approximate
  • Year Built Source Public Records

Property

  • Acreage0.2

Interior

  • Flooring Wood, Tile, Varies

Exterior

  • Exterior Features Rain Gutters, Professional Landscaping, Sprinkler System
  • Fencing Fenced/Enclosed, Fenced
  • RoofShingle

Utilities

  • Electric 200+ Amp Service
  • Sewer Public Sewer
  • Water Source Public

Property Information

  • Building Area Source Public Records
  • Living Area 2,889
  • Lot Size Square Feet 8,550
  • Lot Size Units Acres
  • Square Feet2,889
  • View YN Yes

Amenities

  • Amenities
    • Conservation Area
    • Highway Access
    • House of Worship
    • Marina
    • Park
    • Pool
    • Public School
    • Shopping
    • Walk/Jog Trails
  • Other AmenitiesBasement, Fireplace, Waterfront, Water View
  • Pool Features In Ground

Water Body

  • Miles to Beach0.1
  • WaterfrontYes
  • Waterfront Features Waterfront, Harbor, Harbor, Ocean, Direct Access, Frontage,0 to 1/10 Mile To Beach

Legal

  • Zoningrh6

Other

  • Date Listed06/24/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Amanda George of Lamacchia Realty,Inc.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Castles Unlimited. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.