THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas heating system! 1.08 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties. High probability properties will be changed from TSF to Town Gateway zoning. This offers endless opportunity for residential and business growth. Potential access to rear property from Colony Dr. or Kittredge Lane. Property Addresses are: 39 South Main Street, South Main Street, & 18 Strong Terrace.
For sale
$749,900
39 South Main Street, Winchester, CT 06098
7beds
3,486sqft
Est.:
Multi Family
Built in 1900
-- sqft lot
$713,700 Zestimate®
$215/sqft
$-- HOA
What's special
Wrap around porchBeautiful stone foundationWalk out basementGreat backyardMassive period correct windows
- 99 days
- on Zillow |
- 102 |
- 4 |
Zillow last checked: 7 hours ago
Listing updated: June 30, 2025 at 12:02am
Listed by:
Ryan Horvay,
Smith & DeGroat Real Estate
Source: Smart MLS,MLS#: 24083565

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Hot Water, Natural Gas
Cooling
- None
Appliances
- Included: Water Heater, Tankless Water Heater
Features
- Basement: Full,Unfinished
- Attic: Finished,Walk-up
- Number of fireplaces: 1
Interior area
- Total structure area: 3,486
- Total interior livable area: 3,486 sqft
- Finished area above ground: 3,486
Property
Parking
- Total spaces: 2
- Parking features: Detached
- Garage spaces: 2
Features
- Patio & porch: Wrap Around, Porch, Covered
- Has view: Yes
- View description: City
Lot
- Size: 4.36 Acres
- Features: Secluded, Corner Lot, Few Trees, Level
Details
- Parcel number: 929066
- Zoning: TSF
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units on different Floors
- Property subtype: Multi Family
Materials
- Shake Siding
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Winsted
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $215/sqft
- Tax assessed value: $167,930
- Annual tax amount: $4,899
- Date on market: 3/26/2025
- Loading
- Loading