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: 169
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 · public school directory data (NCES)

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: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 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

Nearby-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 169 days -- 94 more days than Winthrop's current average of 75 days.

For reference, the median list price across 215 active listings in Winthrop right now is $499,900.

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Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

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% / 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.