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104-106 Shirley St, Winthrop MA 02152 - Preview 1 104-106 Shirley St, Winthrop MA 02152 - Preview 2 104-106 Shirley St, Winthrop MA 02152 - Preview 3 104-106 Shirley St, Winthrop MA 02152 - Preview 4 104-106 Shirley St, Winthrop MA 02152 - Preview 5 104-106 Shirley St, Winthrop MA 02152 - Preview 6 104-106 Shirley St, Winthrop MA 02152 - Preview 7 104-106 Shirley St, Winthrop MA 02152 - Preview 8 104-106 Shirley St, Winthrop MA 02152 - Preview 9 104-106 Shirley St, Winthrop MA 02152 - Preview 10 104-106 Shirley St, Winthrop MA 02152 - Preview 11 104-106 Shirley St, Winthrop MA 02152 - Preview 12

104-106 Shirley St, Winthrop MA 02152

Winthrop, MA 02152
$749,974
Est. $4,459/month
Estimate assumptions

20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.

Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.

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5
Beds
2
Baths
2,520
Sq Ft
$298
Price/Sq Ft
0.24
Acres
1910
Year Built
2
Garage Spaces
Multi Family
Type
New today
Time on Market
For Sale Listed Oct 17, 2026 • MLS# 73592145 Copied! • Updated Oct 17, 2026

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About this home

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

BMN Estimate

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A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Price & Status History

Market Insights

Property Timeline

👁️
Showing Instructions Updated
Oct 17, 2026
New showing requirements
🏠
Listed for Sale
Oct 17, 2026
$749,974
Original listing
Agent: Mission Impossible Team Office: United Brokers

Tax History

Year Taxes Assessment
2026 $5,598 $502,500

Financial Details

Annual Property Tax
$5,598
Tax Year 2026
Assessed Value
$502,500

Facts & Features

2 Car Garage

Home Facts

Type Residential Income
Style Multi Family
Year Built 1910
Living Area 2,520 sq ft
Lot Size 0.24 acres
Stories 2
Bedrooms 5
Full Baths 2
Total Rooms 10

Investment Metrics

Units 2
Unit 1 Rent — · N
Unit 2 Rent — · N
Heating None
Cooling None
Flooring Hardwood
Appliances None
Fireplace None
Basement Full, Unfinished
Laundry None
Features None
Construction Frame
Architecture None
Roof Shingle
Features None
Pool None
Spa None
Fencing None
Patio/Porch Porch
Garage Spaces 2
Has Garage Yes
Features None
Total Spaces 6
Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $5,598
Assessed Value $502,500
Fee Includes None
Amenities None
Optional Fee Includes None
Lead Paint Unknown
Seller Disclosures Cash Buyers Only Or Hard Money Loans . The Agents Must Present Proof Of Funds Prior To Showing. There Is No Warranties Implied Or Expressed From Nether The Seller Nor From Agent Of Any Kind.property Is Located On Flood Zone
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Documents None
County Suffolk

Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1910
Bedrooms
5
Full Bathrooms
2
Living Area
2,520 sq ft
Total Rooms
10
Stories
2
Levels
2

Floor Layout

Interior Features

Flooring: Hardwood
Appliances:
Interior Features:
Windows:
Basement: Full, Unfinished
Laundry:
Security:

Construction & Materials

Year Built: 1910
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Other
Stories: 2

Utilities & Systems

Heating:
Cooling:
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch: Porch
Fencing:
Other Structures:
Lot Features: Other
Road Surface:

Parking & Garage

Garage Spaces: 2
Total Parking Spaces: 6
Parking Features:
School District
Winthrop School District local
C
✓ School Safety 2024-25
0.3% Low
0.3% Suspensions
↓ 5.2% below state avg
E

Elementary Schools

2 schools
William P. Gorman/Fort Banks Elementary School
0.3 mi
486 students Moderate
Grades PK-02
B-
Arthur T. Cummings Elementary School
0.6 mi | #447 of 825 | Score: 46.2
Improved 107 spots from last year
-12 below state avg
466 students Moderate
Rising School
Grades 03-05
M

Middle Schools

1 school
B+
Winthrop Middle School
0.2 mi | #118 of 352 | Score: 47.7
Dropped 25 spots from last year
-10.5 below state avg
455 students Moderate
Grades 06-08
H

High Schools

1 school
C+
Winthrop High School
0.2 mi | #238 of 346 | Score: 48.4
Dropped 109 spots from last year
-9.8 below state avg
553 students Moderate
18 sports • 1,118 athletes
High Graduation Rate College Ready Curriculum Strong Athletics
Grades 09-12
Learn about these ratings
School data provided by BMN Schools

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $467
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

104-106 Shirley St, Winthrop MA 02152

Winthrop, MA 02152

Listing Information

Listing Agent Mission Impossible Team
Listing Office United Brokers
Office Phone 781-629-2258
Agent MLS ID TEAM0361
Office MLS ID BB9067
Listing Data Updated Oct 17, 2026 5:32 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steve Novak Real Estate
Steve Novak Real Estate
BMN Boston Powered by SERHANT
mail@steve-novak.com
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