INNOVATE Real Estate
2 Family - 2 Units Side by Side at 105 Ocean View St., Winthrop MA 02152, Winthrop
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38 photos

$989,000

105 Ocean View St., Winthrop MA 02152
Winthrop, MA 02152
Listed by Claudia Perkins
Bedrooms
3
Bathrooms
2
Living area
1,924 sqft
Year built
1886

About this home

Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Fresh updates + meticulous maintenance equal a turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great storage. Welcoming farmer’s porch, fenced yard, and more! 3 OFF STREET PARKING SPACES. Unit 1 offers 2 BR’s, LR, DR, and huge Kitchen. Upstairs, Unit 2 features 1BR plus a windowed dressing room/WFH office, LR, DR and roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement offers more flex space for storage/hobbies. LONG TERM TENANT HISTORY. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes from East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. Rare opportunity! Don't miss!

Property details

MLS #
73537801
Property type
2 Family - 2 Units Side by Side
Subdivision
N/A
Status
Active
Days on market
113
On market date
June 17, 2026
Stories
3
Total bathrooms
2
Garage spaces
N/A
Parking spaces
3
Lot size
0.16 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Arthur T. Cummings Elementary School
0.27 mi away · Grades 3-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
415
Student:teacher ratio
11.9:1
District
Winthrop
Middle
Winthrop Middle School
0.12 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
423
Student:teacher ratio
11.1:1
District
Winthrop
High
Winthrop High School
0.1 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
564
Student:teacher ratio
13.4:1
District
Winthrop

Walkability

Blended score for Winthrop's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

78
Walkable
out of 100
EPA National Walkability Index
14.5 / 20 -- Above average walkable
Google Places amenity density
85 / 100
Restaurants & cafes20
Grocery stores1
Parks20
Schools13
Transit stops20
Pharmacies2

Market position

How this listing compares to current activity in Winthrop, from live MLS data.

On the market 113 days -- 34 more days than Winthrop's current average of 79 days.
For reference, the median list price across 229 active listings in Winthrop right now is $499,900.

Mortgage calculator

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Est. monthly payment
$6,106/mo
$197,800 down
$791,200 loan
Principal & interest$5,132
Property tax (est.)$824
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 27, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.