Winchester, KY homes for sale & real estate

Winchester, KY Homes for Sale

Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/ granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/ private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/ large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.

Winchester, KY Homes for Sale

Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance. Property is under a contingent contract with kick out clause.

Winchester, KY Homes for Sale

Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

Winchester, KY Homes for Sale

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside