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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.

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

$335,000

No Expense was spared on this beautiful, updated home! The Living Room showcases new hardwood flooring and an electric fireplace with changing lights to set the mood! Updated kitchen with new white cabinets, granite counter tops, tile backsplash and all new appliances for easy entertaining! A dining room with a pantry make storage and dinner a breeze! 3 generous sized bedrooms, 3 full bathrooms with excellent classic tile work on the flooring, showers and around the primary bathtub, new modern classic cabinetry, fixtures, and countertops. You can welcome guest on the covered from pouch and entertain on your covered back deck. Alley access allows easy parking under the carport. This is not your average remodel, classic details, attention to detail with updates for modem convivences, you will love this home!

3 Beds ⋅ 3 Baths ⋅ 25501757 MLS

No Expense was spared on this beautiful, updated home! The Living Room showcases new hardwood flooring and an electric fireplace with changing lights to set the mood! Updated kitchen with new white cabinets, granite counter tops, tile backsplash and all new appliances for easy entertaining! A dining room with a pantry make storage and dinner a breeze! 3 generous sized bedrooms, 3 full bathrooms with excellent classic tile work on the flooring, showers and around the primary bathtub, new modern classic cabinetry, fixtures, and countertops. You can welcome guest on the covered from pouch and entertain on your covered back deck. Alley access allows easy parking under the carport. This is not your average remodel, classic details, attention to detail with updates for modem convivences, you will love this home!

536 S Maple St, Winchester

$255,000

Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative studio. The kitchen and adjoining butler's pantry showcase the home's timeless craftsmanship, featuring original built-in cabinetry that blends charm with functionality. A convenient first-floor laundry and mudroom add to the home's practicality. Outside, enjoy a private, fully fenced yard, perfect for pets, play, or simply relaxing outdoors. The unfinished basement with walk-out access provides ample storage. Combining historic charm with modern comfort, this home is ready to welcome its next owners!

3 Beds ⋅ 2 Baths ⋅ 25505142 MLS

Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative studio. The kitchen and adjoining butler's pantry showcase the home's timeless craftsmanship, featuring original built-in cabinetry that blends charm with functionality. A convenient first-floor laundry and mudroom add to the home's practicality. Outside, enjoy a private, fully fenced yard, perfect for pets, play, or simply relaxing outdoors. The unfinished basement with walk-out access provides ample storage. Combining historic charm with modern comfort, this home is ready to welcome its next owners!

357 Crescent Ave, Winchester

$253,000

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.

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

$228,500

Welcome home to this beautifully remodeled home, originally built in 1900 but completely renewed for today's lifestyle. This spacious 4 bedroom, 2 bath home features new tile and carpeting with some of the original hardwood maintained in the living room area and downstairs bedroom. The kitchen has new cabinets, countertops, range, dishwasher and refrigerator. There is a new water heater for your peace of mind. With a perfect mix of historic charm and modern comfort, this home is ready for its new chapter. The listing agent has a family relationship with the seller. The seller is a licensed real estate broker in Kentucky.

4 Beds ⋅ 2 Baths ⋅ 25507786 MLS

Welcome home to this beautifully remodeled home, originally built in 1900 but completely renewed for today's lifestyle. This spacious 4 bedroom, 2 bath home features new tile and carpeting with some of the original hardwood maintained in the living room area and downstairs bedroom. The kitchen has new cabinets, countertops, range, dishwasher and refrigerator. There is a new water heater for your peace of mind. With a perfect mix of historic charm and modern comfort, this home is ready for its new chapter. The listing agent has a family relationship with the seller. The seller is a licensed real estate broker in Kentucky.

394 S Main St, Winchester

$219,900

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!

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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