Single Family Residence at 100 Sargent Street, Winthrop MA 02152, Winthrop

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38 photos

$1,450,000

100 Sargent Street, Winthrop MA 02152

Winthrop, MA 02152

Listed by Elizabeth Ferrara

Bedrooms

Bathrooms

5.5

Living area

5,278 sqft

Year built

1910

About this home

Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one of two driveways. Just off the kitchen, a stunning glass walled sitting room overlooks the home’s standout feature: a large 40K gallon indoor in-ground pool. Additional highlights include a generous garage with expansion potential above. Second floor offers multiple baths, including a primary suite with private bath. The third floor functions well as an in-law suite with its own bedroom, full bath, and living area. Previously operated as a successful legal bed and breakfast, this property presents endless possibilities. Updates include roof 2023, newer pool liner. Perfect opportunity for ADU.

Highlights

Private poolFireplace

Property details

MLS #: 73499355
Property type: Single Family Residence
Subdivision: Cottage Park
Status: Active
Days on market: 175
On market date: April 9, 2026
Stories: N/A
Total bathrooms: 5.5
Garage spaces: 1
Parking spaces: 8
Lot size: 0.26 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

0.56 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

0.93 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

0.91 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).

Walkable

out of 100

EPA National Walkability Index

13.0 / 20 -- Above average walkable

Google Places amenity density

80 / 100

Restaurants & cafes20

Grocery stores1

Parks14

Schools8

Transit stops20

Pharmacies1

Market position

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

On the market 175 days -- 99 more days than Winthrop's current average of 76 days.

For reference, the median list price across 225 active listings in Winthrop right now is $499,900.

Mortgage calculator

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Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

Property tax

% / yr

Home insurance

/mo

Est. monthly payment

$8,882/mo

$290,000 down

$1,160,000 loan

Principal & interest$7,524

Property tax (est.)$1,208

Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated April 13, 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.