Single Family Residence at 39 Henry Street, Winchester

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23 photos

$850,000

39 Henry Street

Winchester, MA 01890

Listed by Kelly Batti

Bedrooms

Bathrooms

Living area

1,313 sqft

Year built

1955

About this home

Exceptional Winchester living awaits at this charming 3-bedroom ranch in the coveted Vinson-Owen district! Offering 1,313 sq. ft. of bright, comfortable space plus basement expansion potential, this home features a classic fireplace living room, formal dining, and a wonderful kitchen. Step outside to a sprawling deck and a lush, private backyard that feels like your own private retreat. Complete with a 2020 roof and 2023 electrical panel, this gem is ready to welcome its next chapter!

Highlights

Fireplace

Property details

MLS: MLS Property Information Network
MLS #: 73585414
Property type: Single Family Residence
Subdivision: N/A
Status: Active
Days on market: 33
On market date: October 1, 2026
Stories: N/A
Total bathrooms: 1
Garage spaces: 1
Parking spaces: 7
Lot size: 0.36 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.

Elementary

Peirce

0.57 mi away · Grades 0-5

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: 326
Student:teacher ratio: 13.0:1
District: Arlington

Middle

Ottoson Middle

1.08 mi away · Grades 7-8

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: 906
Student:teacher ratio: 11.3:1
District: Arlington

High

Arlington High

1.54 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: 1,483
Student:teacher ratio: 13.0:1
District: Arlington

Walkability

Blended score for Winchester'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).

Somewhat walkable

out of 100

EPA National Walkability Index

9.7 / 20 -- Below average walkable

Google Places amenity density

43 / 100

Restaurants & cafes1

Grocery stores0

Parks9

Schools9

Transit stops14

Pharmacies0

Market position

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

On the market 33 days -- 59 fewer days than Winchester's current average of 92 days.

For reference, the median list price across 175 active listings in Winchester right now is $799,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Home price$Down payment%Interest rate%Loan term

Adjust tax / insurance estimates

Property tax% / yrHome insurance$/mo

Est. monthly payment

$5,269/mo

$170,000 down

$680,000 loan

Principal & interest$4,410

Property tax (est.)$708

Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated 10 days ago.

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.