Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates, a new roof, windows, a deck, a kitchen, and an on-demand hot water system. The unit was renovated down to the studs. Separate gas and electric meters make it ideal for owner-occupier or investment use. On-street parking only, but surrounded by other downtown businesses with strong walkability and visibility. Excellent location near Highland Lake, Route 44, and all downtown amenities. Great opportunity to live and work in the same building or generate dual rental income. Bring your vision and make this Main Street property shine again! Also listed as a commercial property- MLS# 24138743
For sale
$395,000
720 Main Street, Winchester, CT 06098
3beds
1,909sqft
Est.:
Multi Family
Built in 1900
-- sqft lot
$384,300 Zestimate®
$207/sqft
$-- HOA
What's special
Existing kitchen areaOpen seating areaRecent updatesNew roofOn-demand hot water systemHigh-visibility two-story building
- 108 days |
- 784 |
- 40 |
Zillow last checked: 8 hours ago
Listing updated: February 13, 2026 at 06:14pm
Listed by:
Ryan Marconi (860)960-6946,
The Washington Agency 860-482-7044
Source: Smart MLS,MLS#: 24138050
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Heating
- Baseboard, Forced Air, Natural Gas
Cooling
- None
Appliances
- Included: Gas Water Heater, Water Heater, Tankless Water Heater
Features
- Basement: None
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 1,909
- Total interior livable area: 1,909 sqft
- Finished area above ground: 1,909
Property
Features
- Patio & porch: Deck
Lot
- Size: 3,049.2 Square Feet
- Features: Level
Details
- Parcel number: 927576
- Zoning: CB-3
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units on different Floors,Other
- Property subtype: Multi Family
Materials
- Vinyl Siding
- Foundation: Slab
- Roof: Asphalt,Flat
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $207/sqft
- Tax assessed value: $47,810
- Annual tax amount: $1,395
- Date on market: 11/12/2025
Estimated market value
$384,300
$365,000 - $404,000
$1,523/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/12/2025 | Listed for sale | $395,000+243.5%$207/sqft |
Source: | ||
| 6/6/2024 | Sold | $115,000+155.6%$60/sqft |
Source: Public Record Report a problem | ||
| 11/1/2016 | Sold | $45,000$24/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,395 +10.5% | $47,810 |
| 2024 | $1,262 | $47,810 |
| 2023 | $1,262 +9.9% | $47,810 +39.7% |
| 2022 | $1,148 | $34,230 |
| 2021 | $1,148 | $34,230 |
| 2020 | $1,148 | $34,230 |
| 2019 | $1,148 | $34,230 |
| 2018 | $1,148 -38.1% | $34,230 -38.1% |
| 2017 | $1,855 -11.4% | $55,300 -11.4% |
| 2016 | $2,094 +2.5% | $62,440 |
| 2015 | $2,042 | $62,440 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,475/mo
Principal & interest
$1889
Property taxes
$586
Climate risks
Neighborhood: 06098
Nearby schools
GreatSchools rating
- 6/10Pearson Middle SchoolGrades: 3-6Distance: 0.4 mi
- NAPearson AcademyGrades: Distance: 0.4 mi
- NABatcheller Early Education CenterGrades: PK-2Distance: 0.8 mi




