263 Front St. Winchendon — Photo 1 of 40
Recent Drop: $24,999
$375,000
263 Front St., Winchendon, MA 01475
Winchendon, MA 01475 — Winchendon Center
Beds
6
Baths
2
SqFt
2,289
Style
2 Family - 2 Units Side by Side
Built
1846
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.
Key facts
It was listed on August 3, 2026. The price has come down from an original $418,000 to $375,000 across 2 changes, most recently on September 11, 2026. The annual property taxes are $2,994 (2025 tax year). It sits on a 0.25-acre (10,890 sq ft) lot.
Market Value Analysis
* Analysis is based on 21 actively listed and recently sold comparable properties strictly within Winchendon, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Neighborhood
Shopping • Park • Walk/Jog Trails • Medical Facility • Laundromat • Bike Path
Geography
Property History
$375,000
Was $399,999
Sep 11, 2026
MLS® 73558512
$399,999
Was $418,000
Sep 1, 2026
MLS® 73558512
$418,000
Aug 3, 2026
MLS® 73558512
Questions about this home
When was 263 Front St., Winchendon listed?
263 Front St., Winchendon was listed on August 3, 2026.
Has the price of 263 Front St., Winchendon changed?
The price has come down from an original $418,000 to $375,000 across 2 changes, most recently on September 11, 2026.
What are the property taxes for 263 Front St., Winchendon?
The annual property taxes for 263 Front St., Winchendon are $2,994 (2025 tax year).
How big is the lot at 263 Front St., Winchendon?
263 Front St., Winchendon sits on a 0.25-acre (10,890 sq ft) lot.
What is the status of 263 Front St., Winchendon?
263 Front St., Winchendon is actively listed for sale.
Population
10,265
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$77K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
23.0%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Worcester County
1,805 housing units permitted in the last 12 months (+1% vs the prior 12 months) — 1,007 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Leanne Roy
Listing Office: Keller Williams Realty North Central
MLS® Number: 73558512
