MLS Listings for Sale in Winchester, KY

MLS Listings for Sale in Winchester, KY

Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home has been thoughtfully updated, featuring an oversized covered back porch—perfect for family gatherings or relaxing dinners—accessible through large sliding glass doors from the spacious family room. The main level boasts a large primary suite with a luxurious bath, while the walk-out ba

MLS Listings for Sale in Winchester, KY

Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated. Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC apartments and 2 renovated ground-floor offices totaling 20 income-producing units. Additional space at 4-10 Main Street offers a blank canvas for tenant improvements and added cash flow. Downtown Winchester is thriving — turn-key, stabilized, and priced to sell. Seize this opportu

MLS Listings for Sale in Winchester, KY

Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval, no warranties implied or expressed. Property conveys at close of escrow with a Quit Claim Deed. Buyer to confirm schools.

MLS Listings for Sale in Winchester, KY

102 W Hickman St, Winchester, KY 40391 Cozy and full of potential! This 1½-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown Winchester, schools, and local amenities, it's a convenient choice for tenants or future owners alike. Don't miss your chance to add this property to your investment portfolio—schedule your showing today!