About this home
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.
Listing last checked: Listing updated:
Listed by Leanne Roy · Keller Williams Realty North Central · MLS #73558512
Request property information
Select a document to start a request. You can add others in the form. Availability varies.
Details at a glance
Interior4 property facts
- Rooms
- 12
- Flooring
- Wood, Tile, Laminate
- Basement
- Yes · Concrete, Unfinished
- Fireplaces
- 1
Building5 property facts
- Style
- 2 Family - 2 Units Side by Side
- Year built
- 1846
- Parking
- 5
- Foundation
- Stone, Granite
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 0.25 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- C2
Financial2 property facts
- Annual taxes
- $2,994
- Assessment year
- 2025
Location
Estimated monthly cost
Explore costs at the $375,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$2,146 / monthAdjust
- Principal & interest
- $1,896
- Property tax
- $250
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $2,994. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $416,911
Estimated range $402,483–$431,340.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: average
Explore more of Winchendon
Continue your search in Winchendon.
Need help making sense of this home?
About 263 Front St.
Can I request a private showing?
Request a tour of 263 Front St. and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.

