229 S Highland St, Winchester, KY, 40391
About This Home
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.
Getting Around
Very Walkable
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1930
Materials
- Foundation: Stone
- Roof: Metal
- Construction materials: HardiPlank Type,Wood Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Refrigerator
Basement
- Has basement: Yes
- Basement: Crawl Space,Interior Entry,Walk-Out Access
Bathroom1
- Level: First
Bathroom2
- Level: Second
Bathroom3
- Level: Second
Bedroom1
- Level: Second
Bedroom2
- Level: Second
Bedroom3
- Level: Second
Bedroom4
- Level: Second
Bedrooms & Bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Dining Room
- Level: First
Family Room
- Level: First
Features
- Flooring: Hardwood
- Number of fireplaces: 3
- Fireplace features: Living Room
- Fireplace: Yes
- Finished area below ground: 0
- Finished area above ground: 3,462
Foyer
- Level: First
Heating & Cooling
- Heating features: Forced Air,Natural Gas
- Cooling features: Electric
Interior Area
- Total structure area: 3,462
- Total interior livable area: 3,462 sqft
Kitchen
- Level: First
Living Room
- Level: First
Master Bedroom
- Level: First
Property
Details
- Parcel number: 054301201400
Features
- Levels: Two
- Fencing: None
Lot
- Lot size: 4,791 sqft
Parking
- Total spaces: 1
- Parking features: Basement,Garage Faces Side
- Has garage: Yes
- Attached garage spaces: 1
- Covered spaces: 1
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Lightning
- Strong Wind
- Tornado
- Winter Weather
- Cold Wave
How This Home’s Risks Compare
FEMA Declared Disasters Across Kentucky Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $834 | $10,008 |
| Home Insurance * | $80 | $960 |
| Property Taxes | $195 | $2,340 |
| Electricity | $273 | $3,280 |
| Total | $1,382 | $16,584 |
Income You'd Need if You Spent...
Kentucky FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
No zestimate history available
Price History
| Date | Event | Price |
|---|---|---|
| 2026-04-22 | Listed for sale | $180,000 |
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