2 Family - 2 Units Side by Side at 263 Front St., Winchendon
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$375,000

263 Front St.
Winchendon, MA 01475
Listed by Leanne Roy
Bedrooms
6
Bathrooms
2
Living area
2,289 sqft
Year built
1846

About this home

UPDATE: All electrical has been updated and brought up to code. 263 Front St. is a well-maintained two-family home offering the perfect blend of charm, space, and investment potential. Each expansive unit features 3 bedrooms, bright and inviting living areas, spacious kitchens, and an abundance of natural light, creating comfortable spaces for both owners and tenants alike. Thoughtfully updated over the years, including two brand-new boilers installed in 2026, this property offers the ideal opportunity for an owner-occupant seeking supplemental rental income or an investor looking to add a turnkey duplex to their portfolio. Ideally situated in a convenient in-town location close to shopping, dining, schools, parks, and commuter routes, this versatile property delivers both lifestyle and long-term value. Whether you're starting your investment journey or growing an established portfolio, this is a property you'll want to see.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73558512
Property type
2 Family - 2 Units Side by Side
Subdivision
N/A
Status
Active
Days on market
93
On market date
August 3, 2026
Stories
4
Total bathrooms
2
Garage spaces
N/A
Parking spaces
5
Lot size
0.25 acres
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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
Toy Town Elementary
0.35 mi away · Grades 3-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
297
Student:teacher ratio
16.5:1
District
Winchendon
Middle
Murdock Middle School
1.32 mi away · Grades 6-8
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
255
Student:teacher ratio
12.1:1
District
Winchendon
High
Murdock Academy for Success
0.35 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
26
Student:teacher ratio
26.0:1
District
Winchendon

Walkability

Blended score for Winchendon'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).

68
Walkable
out of 100
EPA National Walkability Index
10.0 / 20 -- Below average walkable
Google Places amenity density
95 / 100
Restaurants & cafes13
Grocery stores4
Parks7
Schools2
Transit stops3
Pharmacies2

Market position

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

On the market 93 days -- 5 more days than Winchendon's current average of 88 days.
For reference, the median list price across 80 active listings in Winchendon right now is $380,000.

Mortgage calculator

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

Adjust tax / insurance estimates
Est. monthly payment
$2,408/mo
$75,000 down
$300,000 loan
Principal & interest$1,946
Property tax (est.)$313
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated 11 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.