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382 S Main St, Winchester
$370,000
4 Beds ⋅ 3 Baths ⋅ 26008931 MLS
Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.

382 S Main St, Winchester
363 S Main St, Winchester
$253,000
3 Beds ⋅ 2 Baths ⋅ 26009123 MLS
Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY—this spacious 3-bedroom, 2-bath home offers 2,142 square feet of character, updates, and convenience. Ideally located close to all local amenities and just 5 minutes from I-64, you'll enjoy easy access to shopping, dining, and commuting. The home features beautiful hardwood floors and an updated kitchen with plenty of cabinet space, perfect for everyday living and entertaining. Recent improvements include a new roof, soffit, and gutters, along with an updated HVAC system, fresh exterior paint, professional pressure washing, and refreshed landscaping—making this property truly move-in ready. A versatile loft space provides additional storage or future potential, while the covered front porch, back deck, and fenced backyard create the perfect setup for relaxing or hosting guests. This is a rare opportunity to own a well-updated home in a prime downtown location.

363 S Main St, Winchester
339 S Main St, Winchester
$219,900
4 Beds ⋅ 2 Baths ⋅ 26010684 MLS
Beautiful move-in ready Cape Cod home on the edge of historic downtown Winchester! This home is vacant and priced to sell! All new LVP flooring throughout (except for the original hardwood in the Dining Room), new paint in all rooms and so much more! 3 nice-sized bedrooms upstairs and a 4th bedroom on the main level. An eat-in kitchen plus a separate Dining Room and a Family Room with a gas log fireplace. Enjoy your morning coffee or quiet evenings on the 200 sq. ft. covered back porch! Easy and convenient access to schools, shopping, restaurants, and I-64. Downtown Winchester is just a few blocks away. Lexington/Hamburg area is less than 30 minutes via the interstate, US 60 or Todds Road. Call today to make an appointment to see this charming home!

339 S Main St, Winchester

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