Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Boston and Logan Airport, the site and scale are exceptional. Property is being sold strictly in AS-IS, WHERE-IS condition with all faults. Seller or broker make no representations or warranties, express or implied. Buyer to perform all due diligence regarding condition, zoning, permits to able to build , and scope of work
This home has been viewed 10 times
Last Checked: October 18th, 2026 at 8:03am (Source: MLS PIN #73592145)
Gross Income: $0
Gross Expenses: $5,598
Net Income Calc: $5,598
Water Views
Annual Expenses for 104-106 Shirley St, Winthrop MA 02152
Total Gross Expenses (Calculated)$5,598/year
APOD AvailableNo
Heating
Electricity
Water
Gas
Insurance
Sewer
Trash Removal
Repair & Maintenance
Management
Miscellaneous
Real Estate Tax5598
Annual Income & Unit Breakdown for 104-106 Shirley St, Winthrop MA 02152
Total Gross Income (Calculated)$0
Unit 1
Rental Income$0
LeaseN
Bedrooms2
Bathrooms1 Full
Floor1
Levels in Unit1
Rent Includes
Unit 2
Rental Income$0
LeaseN
Bedrooms3
Bathrooms1 Full
Floor2
Levels in Unit1
Rent Includes
General Information for 104-106 Shirley St, Winthrop MA 02152
Listing ID73592145
Property TypeMulti Family
Price749974 ($297.61/SqFt)
StyleMulti Family
CityWinthrop
CountySuffolk
Neighborhood(s)
Approximate Living Area Total2520
Approximate Lot Size (Acres)0.24
Total Parking8 (2 Garage)
Garage Parking2
Year Built1910
Year Built SourcePublic Records
Year Built DetailsActual
WaterPublic
SewerPublic Sewer
Electric
Hot Water
Roof MaterialAsphalt/fiberglass Shingles
BasementFull
Construction MaterialsFrame
Lot FeaturesGentle Sloping
Foundation Description
Accessible Features
Outdoor SpaceCovered
Zoningres
Water ViewsNo
Water Views Features
Waterfront0
Waterfront FeaturesRiver
Terms
Disclosures for 104-106 Shirley St, Winthrop MA 02152
Lead PaintNone
UFFI
Living Area Includes BasementNo
Living Area Disclosure
Building Area SourcePublic Records
ExclusionsOne Set Of Washer And Dryer
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 104-106 Shirley St, Winthrop MA 02152
Real Estate Taxes5598
Tax Year2026
Assessed Value$502,500
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 104-106 Shirley St, Winthrop MA 02152
Elementary SchoolWilliamp.Gorman/Fort Banks
Middle SchoolWinthrop Middle School
High SchoolWinthrop High School
Neighborhood(s)
Area AmenitiesWalk/jog Trails
Contact Information for 104-106 Shirley St, Winthrop MA 02152