1255 The Ridings Rd, Winchester, KY 40391
What's special
Welcome home to this spacious 6-bedroom, 3.5-bath home located in The Ridings—an equestrian-friendly neighborhood offering miles of designated riding trails! The main level features an inviting open-concept kitchen and living area with a cozy gas fireplace, built-ins, and direct access to the covered back deck, perfect for relaxing, entertaining, and watching sunsets. A half bath and laundry area complete the main floor. Upstairs, you'll find the spacious primary suite, three additional bedrooms, and another full bath. The finished walk-out lower level offers incredible flexibility with a second living area opening to a brand-new patio, two additional bedrooms—one currently used as a playroom has an attached bathroom which could be used as a second primary suite—a full a butlers pantry, and plenty of unfinished storage. It's an ideal setup for guests, extended family, or additional living space. Outside, the property is fully enclosed with four-plank horse fencing and additional wire fencing, giving both horses and four-legged family members room to safely enjoy the outdoors. An attached flex space with its own separate rear entrance makes the perfect man cave, hobby room, home gym, or private office. A detached garage with convenient backyard access provides additional storage for your mower, equipment, and more. Enjoy peaceful country-style living while remaining convenient to everything—approximately 13 miles to Hamburg, 18 miles to downtown Lexington, 16 miles to I-75, and just 5 miles to I-64. With generous living space, a versatile walk-out basement, fenced grounds, and access to miles of riding trails, this property offers a lifestyle that's hard to find!
- 20 days
- 833
- 111
Likely to sell faster than
Travel times
Family Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Lucy Martin Jenkins 859-771-4088,
United Real Estate Bluegrass
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Level: First
Bedroom 1
- Level: Second
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bedroom 5
- Level: Lower
Primary bathroom
- Level: Second
Bathroom 1
- Level: First
Bathroom 3
- Level: Second
Bathroom 4
- Level: Lower
Foyer
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Living room
- Level: Lower
Office
- Level: First
Other
- Description: Bedroom 6
- Level: Lower
Heating
- Natural Gas
Cooling
- Electric
Appliances
- Included: Disposal, Dishwasher, Microwave, Refrigerator, Range
- Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
Features
- Entrance Foyer, Eat-in Kitchen, In-Law Floorplan, Walk-In Closet(s), Ceiling Fan(s), Soaking Tub
- Flooring: Carpet, Hardwood, Tile, Vinyl
- Windows: Insulated Windows, Blinds, Screens
- Basement: Bath/Stubbed,Exterior Entry,Interior Entry,Partially Finished,Unfinished,Walk-Out Access
- Number of fireplaces: 2
- Fireplace features: Basement, Gas Log, Living Room
Interior area
- Total structure area: 3,789
- Total interior livable area: 3,789 sqft
- Finished area above ground: 2,430
- Finished area below ground: 1,359
Property
Parking
- Total spaces: 2
- Parking features: Attached Garage, Basement, Detached Garage, Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Workshop
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Three Or More,Two
- Fencing: Partial,Wood,Wire
- Has view: Yes
- View description: Rural, Farm
Lot
- Size: 5.12 Acres
Details
- Additional structures: Shed(s)
- Parcel number: 033000003100
- Horses can be raised: Yes
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Brick Veneer, Vinyl Siding
- Foundation: Concrete Perimeter, Slab
- Roof: Dimensional Style,Shingle
Condition
- Year built: 1997
Utilities & green energy
- Sewer: Private Sewer, Septic Tank
- Water: Public
Community & HOA
Community
- Subdivision: The Ridings
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $205/sqft
- Tax assessed value: $421,300
- Annual tax amount: $4,049
- Date on market: 9/22/2026
Price history
| Date | Event | Price |
|---|---|---|
| 9/30/2026 | Contingent | $775,000$205/sqft |
Source:  Imagine MLS #26026145 Report a problem | ||
| 9/22/2026 | Listed for sale | $775,000+25.1%$205/sqft |
Source: Imagine MLS #26026145 Report a problem | ||
| 4/26/2024 | Sold | $619,500-4%$163/sqft |
Source: Imagine MLS #24002763 Report a problem | ||
| 4/18/2024 | Contingent | $645,000$170/sqft |
Source: Imagine MLS #24002763 Report a problem | ||
| 2/15/2024 | Listed for sale | $645,000+124.7%$170/sqft |
Source: Imagine MLS #24002763 Report a problem | ||
| 10/26/2001 | Sold | $287,000$76/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,049 -3.9% | $421,300 |
| 2024 | $4,213 +1.5% | $421,300 |
| 2023 | $4,150 | $421,300 |
| 2022 | $4,150 +0.3% | $421,300 |
| 2021 | $4,138 +11.1% | $421,300 +11.3% |
| 2020 | $3,725 -0.5% | $378,500 |
| 2019 | $3,744 +1.2% | $378,500 |
| 2018 | $3,699 +7.4% | $378,500 |
| 2017 | $3,445 | $378,500 +5.6% |
| 2016 | $3,445 | $358,500 |
| 2015 | $3,445 +4.9% | $358,500 |
| 2013 | $3,284 | $358,500 +2.9% |
| 2011 | -- | $348,500 |
| 2010 | -- | $348,500 |
Monthly payment
Estimated market value
Not available
Estimated sales range
Not available
Not available
Climate risks
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