4664 Lexington Rd, Winchester, KY, 40391
About This Home
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1996
Materials
- Foundation: Concrete Perimeter
- Roof: Shingle
- Construction materials: Brick Veneer
Type & Style
- Home type: SingleFamily
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Double Oven,Dishwasher,Refrigerator,Cooktop
- Laundry features: Main Level
Basement
- Has basement: Yes
- Basement: Exterior Entry,Finished,Full,Walk-Out Access
Bathroom1
- Level: First
Bathroom2
- Level: Second
Bathroom3
- Level: Second
Bathroom4
- Level: Second
Bathroom5
- Level: First
Bedroom1
- Level: Second
Bedroom2
- Level: Second
Bedroom3
- Level: Second
Bedroom4
- Level: Second
Bedroom5
- Level: Second
Bedrooms & Bathrooms
- Bedrooms: 8
- Bathrooms: 8
- Full bathrooms: 7
- 1/2 bathrooms: 1
Features
- Entrance Foyer,Eat-in Kitchen,Walk-In Closet(s),Soaking Tub
- Flooring: Carpet,Hardwood,Tile
- Number of fireplaces: 2
- Fireplace features: Gas Log,Kitchen,Living Room,Master Bedroom
- Fireplace: Yes
- Finished area below ground: 5,174
- Finished area above ground: 8,259
Heating & Cooling
- Heating features: Forced Air,Natural Gas
- Cooling features: Central Air
Interior Area
- Total structure area: 13,433
- Total interior livable area: 13,433 sqft
Kitchen
- Level: First
Living Room
- Level: First
Master Bathroom
- Level: First
Master Bedroom
- Level: First
Property
Details
- Parcel number: 022000000601
Features
- Levels: Three Or More
- Private pool: Yes
- Pool features: In Ground
- Fencing: Wood
- Has view: Yes
- View description: Rural,Trees/Woods,Farm
- Horses can be raised: Yes
Lot
- Lot size: 35 Acres
- Features: Secluded
Parking
- Total spaces: 4
- Parking features: Attached Garage,Driveway,Garage Faces Side
- Has garage: Yes
- Attached garage spaces: 4
- Covered spaces: 4
- Has uncovered spaces: Yes
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
- Strong Wind
- Tornado
- Lightning
- 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 | $13,905 | $166,860 |
| Home Insurance * | $1,347 | $16,164 |
| Property Taxes | $2,249 | $26,988 |
| Electricity | $1,060 | $12,729 |
| Total | $18,561 | $222,732 |
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 |
|---|---|---|
| 2026-05-01 | Listed for sale | $2,750,000 |
| 2025-10-14 | Listing removed | $3,175,000 |
| 2025-06-06 | Listed for sale | $3,175,000 |
| 2024-10-15 | Listing removed | $3,500,000 |
| 2024-05-15 | Listed for sale | $3,500,000 |
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