Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout with soaring vaulted ceilings, a dual-sided fireplace, and an interior balcony overlooking the formal dining room. The full walkout basement, complete with a half bath, offers incredible potential to finish for additional living space, a guest suite, or a home office. Additional highlights include central air, a stone patio perfect for entertaining, a covered breezeway with scenic views, and a paved driveway. All set on a private, secluded lot, this property combines comfort, versatility, and opportunity rarely found on the market.
Sold for $388,750 on 10/29/25
$388,750
111 Old North Road, Winchester, CT 06098
3beds
1,584sqft
Single Family Residence
Built in 1973
0.99 Acres Lot
$370,500 Zestimate®
$245/sqft
$3,202 Estimated rent
Home value
$370,500
$352,000 - $389,000
$3,202/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: October 31, 2025 at 11:52am
Listed by:
Chris Clarke 860-879-6650,
Coldwell Banker Realty 203-239-2553
Bought with:
Jared Tedesco, RES.0821976
Litchfield County Real Estate
Source: Smart MLS,MLS#: 24120714
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Remodeled, Cathedral Ceiling(s), Interior Balcony, Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Main
Bedroom
- Features: Wall/Wall Carpet
- Level: Main
Dining room
- Features: 2 Story Window(s), Vaulted Ceiling(s), French Doors, Patio/Terrace, Sliders, Wall/Wall Carpet
- Level: Main
Kitchen
- Features: Remodeled, Bay/Bow Window, Eating Space, Tile Floor
- Level: Main
Living room
- Features: Bay/Bow Window, Fireplace, Wall/Wall Carpet
- Level: Main
Study
- Features: Interior Balcony
- Level: Upper
Heating
- Baseboard, Zoned, Oil
Cooling
- Central Air
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater, Tankless Water Heater
- Laundry: Lower Level
Features
- Wired for Data
- Doors: Storm Door(s), French Doors
- Windows: Thermopane Windows
- Basement: Full
- Attic: Access Via Hatch
- Number of fireplaces: 2
Interior area
- Total structure area: 1,584
- Total interior livable area: 1,584 sqft
- Finished area above ground: 1,584
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Attached, Paved, Off Street, Driveway, Garage Door Opener
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: Multi/Split
- Patio & porch: Porch, Patio
- Exterior features: Breezeway, Rain Gutters
Lot
- Size: 0.99 Acres
- Features: Secluded, Cleared, Landscaped
Details
- Additional structures: Shed(s)
- Parcel number: 924301
- Zoning: RR
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch,Split Level
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1973
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Doors, Windows
Community & neighborhood
Community
- Community features: Basketball Court, Near Public Transport, Health Club, Lake, Shopping/Mall
Location
- Region: Winsted
Price history
| Date | Event | Price |
|---|---|---|
| 10/31/2025 | Pending sale | $375,000-3.5%$237/sqft |
Source:  Smart MLS #24120714 Report a problem | ||
| 10/29/2025 | Sold | $388,750+3.7%$245/sqft |
Source: Smart MLS #24120714 Report a problem | ||
| 8/26/2025 | Listed for sale | $375,000$237/sqft |
Source: Smart MLS #24120714 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,807 +10.5% | $164,780 |
| 2024 | $4,349 | $164,780 |
| 2023 | $4,349 +1.6% | $164,780 +29.1% |
Find assessor info on the county website
Neighborhood: 06098
Nearby schools
GreatSchools rating
- 6/10Pearson Middle SchoolGrades: 3-6Distance: 1.7 mi
- NAPearson AcademyGrades: Distance: 1.7 mi
- NABatcheller Early Education CenterGrades: PK-2Distance: 2.6 mi
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Sell for more on Zillow
Get a free Zillow Showcase℠ listing and you could sell for .
$370,500
2% more+ $7,410
With Zillow Showcase(estimated)
$377,910