1024 Flanagan Station Rd, Winchester, KY, 40391
About This Home
Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1975
Materials
- Foundation: Block
- Roof: Shingle
- Construction materials: Wood Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Dishwasher,Range
Basement
- Has basement: Yes
- Basement: Partially Finished
Bedrooms & Bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Features
- Eat-in Kitchen,Ceiling Fan(s)
- Window features: Skylight(s)
- Flooring: Carpet,Hardwood,Laminate
- Number of fireplaces: 1
- Fireplace features: Living Room
- Fireplace: Yes
- Finished area below ground: 0
- Finished area above ground: 2,942
Heating & Cooling
- Heating features: Electric,Heat Pump
- Cooling features: Electric,Heat Pump
Interior Area
- Total structure area: 2,942
- Total interior livable area: 2,942 sqft
Kitchen
- Level: First
Master Bedroom
- Level: First
Property
Details
- Parcel number: 045000003500
Features
- Horses can be raised: Yes
Lot
- Lot size: 8.90 Acres
- Features: Secluded
Parking
- Total spaces: 2
- Parking features: Attached Garage
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
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
- Hail
- Inland Flooding
- Ice Storm
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 | $2,351 | $28,212 |
| Home Insurance * | $227 | $2,724 |
| Property Taxes | $328 | $3,936 |
| Electricity | $232 | $2,788 |
| Total | $3,138 | $37,656 |
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 |
|---|---|---|
| 2026-08-18 | Price change | $429,000 |
| 2026-08-04 | Price change | $449,000 |
| 2026-07-17 | Listed for sale | $465,000 |
| 2010-02-26 | Sold | $240,000 |
| 2000-04-17 | Sold | $210,000 |
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