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Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3 bedrooms and 2.5 bathrooms with an easy-flow layout ideal for everyday living. The primary suite offers a private retreat complete with vaulted ceilings, a walk-in closet, and direct access to the covered back patio. The ensuite bathroom includes a corner jetted tub, separate tiled walk-in shower with glass door, raised-height double bowl vanity, and linen closet for added storage. The main living areas provide comfortable gathering spaces, while the previous owners enclosed the original garage to create a large additional family room/game room with a half bath. This flexible space works well as a second living area, office, home gym, playroom, hobby space, or entertainment room depending on your needs. Outdoor living is a highlight of this property. Covered front and back patios provide shaded spaces for relaxing or entertaining, while the fenced backyard includes a brand-new above-ground pool that will convey with the sale. Beyond the home, the acreage offers open usable space along with multiple structures including a detached two-car garage, storage shed, and barn — ideal for equipment, animals, workshop use, or additional storage. With acreage, outbuildings, fenced areas, and convenient parkway access, this property offers flexibility for mini-farm living, recreational use, or simply enjoying extra space and privacy. If you've been searching for one-level living on land with multiple structures and outdoor amenities, 233 Cunningham Lane provides a unique opportunity in the Winchester area. 48 Hour Kick Out Clause contract in place as of 3/24/2026.

3 Beds ⋅ 3 Baths ⋅ 25507450 MLS

Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3 bedrooms and 2.5 bathrooms with an easy-flow layout ideal for everyday living. The primary suite offers a private retreat complete with vaulted ceilings, a walk-in closet, and direct access to the covered back patio. The ensuite bathroom includes a corner jetted tub, separate tiled walk-in shower with glass door, raised-height double bowl vanity, and linen closet for added storage. The main living areas provide comfortable gathering spaces, while the previous owners enclosed the original garage to create a large additional family room/game room with a half bath. This flexible space works well as a second living area, office, home gym, playroom, hobby space, or entertainment room depending on your needs. Outdoor living is a highlight of this property. Covered front and back patios provide shaded spaces for relaxing or entertaining, while the fenced backyard includes a brand-new above-ground pool that will convey with the sale. Beyond the home, the acreage offers open usable space along with multiple structures including a detached two-car garage, storage shed, and barn — ideal for equipment, animals, workshop use, or additional storage. With acreage, outbuildings, fenced areas, and convenient parkway access, this property offers flexibility for mini-farm living, recreational use, or simply enjoying extra space and privacy. If you've been searching for one-level living on land with multiple structures and outdoor amenities, 233 Cunningham Lane provides a unique opportunity in the Winchester area. 48 Hour Kick Out Clause contract in place as of 3/24/2026.

233 Cunningham Ln, Winchester

$395,000

Welcome to Winchester living at its finest! Nestled on a spacious .68-acre lot in the desirable Stoney Brook area, this well-maintained brick ranch offers 3 bedrooms, 2 full baths, and approximately 1,883 square feet of comfortable living space. Inside, you'll find a functional floor plan featuring a cozy fireplace, generous living areas, and abundant natural light throughout. The attached garage, off-street parking, and patio provide both convenience and great outdoor entertaining space. Enjoy the peaceful setting while still being just minutes from the Winchester Bypass, shopping, dining, and an easy drive to Lexington. A wonderful opportunity to own a solid home with charm, space, and an unbeatable location!

3 Beds ⋅ 2 Baths ⋅ 26011118 MLS

Welcome to Winchester living at its finest! Nestled on a spacious .68-acre lot in the desirable Stoney Brook area, this well-maintained brick ranch offers 3 bedrooms, 2 full baths, and approximately 1,883 square feet of comfortable living space. Inside, you'll find a functional floor plan featuring a cozy fireplace, generous living areas, and abundant natural light throughout. The attached garage, off-street parking, and patio provide both convenience and great outdoor entertaining space. Enjoy the peaceful setting while still being just minutes from the Winchester Bypass, shopping, dining, and an easy drive to Lexington. A wonderful opportunity to own a solid home with charm, space, and an unbeatable location!

18 Casa Landa Way, Winchester

$392,000

This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along with plush new carpet on the upper level. The two remodeled bathrooms feature sleek finishes that add a touch of luxury to your daily routine. The spacious kitchen boasts many new appliances, making meal prep a breeze, while the washer and dryer will stay for added convenience. Outside, this home shines with a freshly landscaped yard, a brand-new deck perfect for entertaining, and newly installed shutters that elevate the curb appeal. With an updated HVAC and heater (2020), you'll enjoy peace of mind knowing your home is not only beautiful but energy-efficient, too. Situated on a massive lot, there's ample space for outdoor activities, gardening, or even future expansion. Whether you're relaxing on your deck or enjoying the large, serene lot, this property offers a lifestyle of comfort and beauty at every turn. Don't miss your chance to own this incredible, move-in-ready home at 397 Calmes Blvd! ****Sellers are willing to negotiate all furniture in and outside the house!

4 Beds ⋅ 4 Baths ⋅ 25500875 MLS

This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along with plush new carpet on the upper level. The two remodeled bathrooms feature sleek finishes that add a touch of luxury to your daily routine. The spacious kitchen boasts many new appliances, making meal prep a breeze, while the washer and dryer will stay for added convenience. Outside, this home shines with a freshly landscaped yard, a brand-new deck perfect for entertaining, and newly installed shutters that elevate the curb appeal. With an updated HVAC and heater (2020), you'll enjoy peace of mind knowing your home is not only beautiful but energy-efficient, too. Situated on a massive lot, there's ample space for outdoor activities, gardening, or even future expansion. Whether you're relaxing on your deck or enjoying the large, serene lot, this property offers a lifestyle of comfort and beauty at every turn. Don't miss your chance to own this incredible, move-in-ready home at 397 Calmes Blvd! ****Sellers are willing to negotiate all furniture in and outside the house!

397 Calmes Blvd, Winchester

$390,000

Welcome to one of Winchester's most established neighborhoods. This charming 2 story offers 4 bedrooms, 2 full baths, and 2 half baths, one in the finished basement. The layout features cozy nooks throughout the second story and a recently added bedroom over the garage with its own mini split hvac, perfect for guests, a home office, or creative space. The finished basement provides room for entertaining, play, or movie nights. Enjoy a covered front porch, covered back deck and a spacious backyard with mature trees. Just minutes from downtown Winchester and a short drive to Lexington, this home combines charm, space, and convenience. Property is contingent with a 48 hr kickout and seller is still accepting back up offers

4 Beds ⋅ 4 Baths ⋅ 25017132 MLS

Welcome to one of Winchester's most established neighborhoods. This charming 2 story offers 4 bedrooms, 2 full baths, and 2 half baths, one in the finished basement. The layout features cozy nooks throughout the second story and a recently added bedroom over the garage with its own mini split hvac, perfect for guests, a home office, or creative space. The finished basement provides room for entertaining, play, or movie nights. Enjoy a covered front porch, covered back deck and a spacious backyard with mature trees. Just minutes from downtown Winchester and a short drive to Lexington, this home combines charm, space, and convenience. Property is contingent with a 48 hr kickout and seller is still accepting back up offers

213 Honeysuckle Ln, Winchester

$390,000

Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with a built-in bench for convenient storage. The open concept offers both comfort and style. Between the kitchen's open design with granite countertops to the primary suite that offers relaxation at its finest. You may have a hard time deciding on which area of the home you wish to be in. Enjoy your outdoor space that offers a privacy fence and a 10'x16' building for your mower and additional storage. This home invites you to experience the best of Kentucky living and is just waiting on you to call it home! Located only 4 Minutes to Walmart!

3 Beds ⋅ 3 Baths ⋅ 26012931 MLS

Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with a built-in bench for convenient storage. The open concept offers both comfort and style. Between the kitchen's open design with granite countertops to the primary suite that offers relaxation at its finest. You may have a hard time deciding on which area of the home you wish to be in. Enjoy your outdoor space that offers a privacy fence and a 10'x16' building for your mower and additional storage. This home invites you to experience the best of Kentucky living and is just waiting on you to call it home! Located only 4 Minutes to Walmart!

178 Hawthorne Dr, Winchester

$389,000

Properties like this don't come along that often, don't miss your chance to see this amazing property. It features 6.14 acres of land with multiple barns and open fields. Not to mention a house and a view to fall in love with the moment you see it. This Brick Home features 3 Bedrooms on the main level with 2 full baths, large living room with fireplace, open kitchen with dining room right beside it, large closets, two car attached garage, concrete driveway, back deck with ramp, front and back porches, and a full basement with a UK game room and additional living space. Just minutes from downtown Winchester's Best Restaurants, and shopping. Work outside of Winchester, no problem I-64 is only a few miles away, so this location has it all.

4 Beds ⋅ 3 Baths ⋅ 25506282 MLS

Properties like this don't come along that often, don't miss your chance to see this amazing property. It features 6.14 acres of land with multiple barns and open fields. Not to mention a house and a view to fall in love with the moment you see it. This Brick Home features 3 Bedrooms on the main level with 2 full baths, large living room with fireplace, open kitchen with dining room right beside it, large closets, two car attached garage, concrete driveway, back deck with ramp, front and back porches, and a full basement with a UK game room and additional living space. Just minutes from downtown Winchester's Best Restaurants, and shopping. Work outside of Winchester, no problem I-64 is only a few miles away, so this location has it all.

4530 Ironworks Rd, Winchester

$387,500

Wonderfully renovated historic building across from the Court House in Downtown Winchester! The well appointed restaurant space has a full hood system, concrete bar, beautiful hardwood floors, tin ceiling and parking in the back. The apartment is the perfect size and has a private deck! Great opportunity to live upstairs and have your restaurant downstairs! Downtown Winchester is the place to be. Close enough to Lexington but far enough away to be a destination. Numerous apartments are coming soon, great restaurants and lots of tourists make this a great place to start a business. Property Highlights: -Full hood system, concrete bar, hardwood floors, tin ceiling, and a full commercial kitchen -Building retains historic charm with a significant portion dating back to the original construction, coupled with a recent renovation to maximize functionality -Conducive to live/work layout and/or short-term rentals -Downtown Winchester, KY is booming - everyone wants to be Downtown including shops, restaurants, and new apartment living options

25014867 MLS

Wonderfully renovated historic building across from the Court House in Downtown Winchester! The well appointed restaurant space has a full hood system, concrete bar, beautiful hardwood floors, tin ceiling and parking in the back. The apartment is the perfect size and has a private deck! Great opportunity to live upstairs and have your restaurant downstairs! Downtown Winchester is the place to be. Close enough to Lexington but far enough away to be a destination. Numerous apartments are coming soon, great restaurants and lots of tourists make this a great place to start a business. Property Highlights: -Full hood system, concrete bar, hardwood floors, tin ceiling, and a full commercial kitchen -Building retains historic charm with a significant portion dating back to the original construction, coupled with a recent renovation to maximize functionality -Conducive to live/work layout and/or short-term rentals -Downtown Winchester, KY is booming - everyone wants to be Downtown including shops, restaurants, and new apartment living options

39 S Main St, Winchester

$385,000

*NEW PAINT and FLOORING* This spacious property offers exceptional value and strong potential in a sought-after area. The main house has been freshly painted and brand new flooring throughout. Versatile Home on 5.47 Acres with Horse Barn & Multi-Unit Living. Welcome to your private hilltop retreat with panoramic mountain views. This property blends flexibility, privacy, and income potential—perfect for multi-generational living, homesteading, or rental investment. The main home features 4 bedrooms and 3 full baths. Two additional living spaces include a 2-bed, 1-bath upstairs apartment with its own kitchen, laundry, and entrance, and a 1-bed, 1-bath downstairs unit with private entry. Both units have a total of 867 square feet each. Whether you're housing extended family, hosting guests, or creating passive income, the setup offers rare independence and versatility. Outdoors, the small barn offers options for a couple of horses, a garage, or a workshop. The open acreage invites gardening, riding, or simply enjoying peaceful sunrises and sunsets over the ridgeline. Just minutes from town yet in quiet seclusion.

4 Beds ⋅ 3 Baths ⋅ 25012505 MLS

*NEW PAINT and FLOORING* This spacious property offers exceptional value and strong potential in a sought-after area. The main house has been freshly painted and brand new flooring throughout. Versatile Home on 5.47 Acres with Horse Barn & Multi-Unit Living. Welcome to your private hilltop retreat with panoramic mountain views. This property blends flexibility, privacy, and income potential—perfect for multi-generational living, homesteading, or rental investment. The main home features 4 bedrooms and 3 full baths. Two additional living spaces include a 2-bed, 1-bath upstairs apartment with its own kitchen, laundry, and entrance, and a 1-bed, 1-bath downstairs unit with private entry. Both units have a total of 867 square feet each. Whether you're housing extended family, hosting guests, or creating passive income, the setup offers rare independence and versatility. Outdoors, the small barn offers options for a couple of horses, a garage, or a workshop. The open acreage invites gardening, riding, or simply enjoying peaceful sunrises and sunsets over the ridgeline. Just minutes from town yet in quiet seclusion.

1731 Ford Hampton Rd, Winchester

$385,000

This beautiful home is move-in-ready and waiting for your family to call it home. Situated in the desirable Oak Hill subdivision with easy access to the bypass and all that Winchester has to offer! Step inside the front door and enjoy the spacious great room featuring a cozy living room with a lovely fireplace with built-ins on both sides. From there, you can access the updated kitchen with white cabinets and granite countertops. The main floor includes 3 bedrooms and 2 full bathrooms. In the finished basement has a generous family room, another full bathroom as well as some extra storage space. Take a step out the back door to enjoy the private covered trex deck, perfect for daily use throughout the year. With all new windows, a new roof, and a new water heater, this home is not to be missed! Schedule your private showing today.

3 Beds ⋅ 3 Baths ⋅ 25503295 MLS

This beautiful home is move-in-ready and waiting for your family to call it home. Situated in the desirable Oak Hill subdivision with easy access to the bypass and all that Winchester has to offer! Step inside the front door and enjoy the spacious great room featuring a cozy living room with a lovely fireplace with built-ins on both sides. From there, you can access the updated kitchen with white cabinets and granite countertops. The main floor includes 3 bedrooms and 2 full bathrooms. In the finished basement has a generous family room, another full bathroom as well as some extra storage space. Take a step out the back door to enjoy the private covered trex deck, perfect for daily use throughout the year. With all new windows, a new roof, and a new water heater, this home is not to be missed! Schedule your private showing today.

1138 Lafayette Blvd, Winchester

$385,000

Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to relax or gather with friends and family. Just off the living area is a climate-controlled sunroom filled with windows and natural light, with direct access to the backyard and semi-permanent fencing. Down the hall are three bedrooms and a full guest bath that has been refreshed with new paint, beadboard and chair rail, plus a spacious primary bedroom with its own private bath. With a mix of hardwood, tile, carpet and vinyl flooring throughout and an attached two-car garage, this home has plenty of space, charm and potential to make it your own!

4 Beds ⋅ 2 Baths ⋅ 26021961 MLS

Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to relax or gather with friends and family. Just off the living area is a climate-controlled sunroom filled with windows and natural light, with direct access to the backyard and semi-permanent fencing. Down the hall are three bedrooms and a full guest bath that has been refreshed with new paint, beadboard and chair rail, plus a spacious primary bedroom with its own private bath. With a mix of hardwood, tile, carpet and vinyl flooring throughout and an attached two-car garage, this home has plenty of space, charm and potential to make it your own!

406 Lynnway Dr, Winchester

$380,000

Beautifully remodeled 4-bedroom, 3-full bath ranch nestled on a picturesque lot in one of Winchester's most desirable and well-established neighborhoods. Step inside to find a perfect blend of timeless charm and modern updates throughout. The main level offers a spacious and inviting layout with stunning finishes, featuring multiple fireplaces that create warmth and character in every living space. The kitchen and baths have been completely renovated with today's most sought-after designs and materials. Downstairs, the partially finished basement adds even more living space — complete with a cozy family room and fireplace, a fourth bedroom, and a full bath — ideal for guests, a home office, or an in-law suite. Outside, enjoy the most perfect covered porch overlooking the peaceful backyard with mature trees. The property also includes two outbuildings, providing ample storage or space for hobbies and projects. With three fireplaces total, a thoughtful floor plan, and a full renovation from top to bottom, this home is truly move-in ready and one you don't want to miss!

4 Beds ⋅ 3 Baths ⋅ 25504610 MLS

Beautifully remodeled 4-bedroom, 3-full bath ranch nestled on a picturesque lot in one of Winchester's most desirable and well-established neighborhoods. Step inside to find a perfect blend of timeless charm and modern updates throughout. The main level offers a spacious and inviting layout with stunning finishes, featuring multiple fireplaces that create warmth and character in every living space. The kitchen and baths have been completely renovated with today's most sought-after designs and materials. Downstairs, the partially finished basement adds even more living space — complete with a cozy family room and fireplace, a fourth bedroom, and a full bath — ideal for guests, a home office, or an in-law suite. Outside, enjoy the most perfect covered porch overlooking the peaceful backyard with mature trees. The property also includes two outbuildings, providing ample storage or space for hobbies and projects. With three fireplaces total, a thoughtful floor plan, and a full renovation from top to bottom, this home is truly move-in ready and one you don't want to miss!

110 Hampton Ave, Winchester

$380,000

The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1/2 bathrooms, with full basement and mother in law suite. It sits on just over 3 spacious acres. There is a 24X36 work shop just built in 2022. The roof and HVAC are just 6 years old. The water heater is 6 months old. The property has 10 beautiful apple trees and 3 pear trees. The home is just minutes from I-64, Winchester, and Mount Sterling.

4 Beds ⋅ 3 Baths ⋅ 25017919 MLS

The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1/2 bathrooms, with full basement and mother in law suite. It sits on just over 3 spacious acres. There is a 24X36 work shop just built in 2022. The roof and HVAC are just 6 years old. The water heater is 6 months old. The property has 10 beautiful apple trees and 3 pear trees. The home is just minutes from I-64, Winchester, and Mount Sterling.

5705 Mount Sterling Rd, Winchester

$379,717

Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half modern bathrooms *Located just minutes from the Winchester Bypass *Close to golf courses, shopping centers, and dining options Enjoy the perfect blend of comfort and convenience in one of Winchester's most desirable communities.

3 Beds ⋅ 3 Baths ⋅ 25504889 MLS

Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half modern bathrooms *Located just minutes from the Winchester Bypass *Close to golf courses, shopping centers, and dining options Enjoy the perfect blend of comfort and convenience in one of Winchester's most desirable communities.

300 Calmes Blvd, Winchester

$379,000

Welcome to this spacious two-story brick home set on a beautiful half-acre lot in a quiet Winchester subdivision, just 10 miles from Hamburg. With approximately 2,600 square feet of living space, this residence offers an exceptional blend of comfort, functionality, and location—perfect for families or anyone seeking a peaceful retreat close to city conveniences. Inside, you'll find four bedrooms and two-and-a-half baths, providing plenty of room for family, guests, or a growing household. The main living areas feature 8-foot ceilings and a fireplace in the cozy den, creating a welcoming space to relax or entertain. The basement expands your living options—ideal for a recreation room, home gym, or media space. Car enthusiasts and hobbyists alike will appreciate the attached two-car garage and a large detached 14X24 insulated workshop with its own garage door, and a fully finished attic space with pull-down access. Step outside to enjoy the lovely half-acre lot, which offers room to garden, play, or simply unwind in a serene setting.

4 Beds ⋅ 3 Baths ⋅ 25015683 MLS

Welcome to this spacious two-story brick home set on a beautiful half-acre lot in a quiet Winchester subdivision, just 10 miles from Hamburg. With approximately 2,600 square feet of living space, this residence offers an exceptional blend of comfort, functionality, and location—perfect for families or anyone seeking a peaceful retreat close to city conveniences. Inside, you'll find four bedrooms and two-and-a-half baths, providing plenty of room for family, guests, or a growing household. The main living areas feature 8-foot ceilings and a fireplace in the cozy den, creating a welcoming space to relax or entertain. The basement expands your living options—ideal for a recreation room, home gym, or media space. Car enthusiasts and hobbyists alike will appreciate the attached two-car garage and a large detached 14X24 insulated workshop with its own garage door, and a fully finished attic space with pull-down access. Step outside to enjoy the lovely half-acre lot, which offers room to garden, play, or simply unwind in a serene setting.

122 Leann Ln, Winchester

$378,000

Step inside this spacious 4 bedroom home with a large open living concept, primary suite with impressive walkin closet space, covered back patio, and all of this on an unfinished basement. Schedule your showing today.

4 Beds ⋅ 3 Baths ⋅ 26003011 MLS

Step inside this spacious 4 bedroom home with a large open living concept, primary suite with impressive walkin closet space, covered back patio, and all of this on an unfinished basement. Schedule your showing today.

140 Gibson Way, Winchester

$375,750

Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600 square feet, this 4-bedroom, 2-bath home provides plenty of room to spread out. The unfinished basement and one-car attached garage offer great storage, workshop potential, or future expansion. Inside, you'll find a welcoming foyer that opens to a bright, spacious living and dining area filled with natural light from large windows overlooking the countryside. The eat-in kitchen sits at the heart of the home, featuring stainless steel appliances, generous cabinet space, a walk-in pantry, and a cozy fireplace—perfect for gathering after a long day. Just beyond the kitchen is a large bonus room highlighted by charming brick details, ideal for entertaining, a family room, or even a home office or hobby space. The main level includes two roomy bedrooms, an updated full bath, and a convenient laundry room. Upstairs, the private primary bedroom offers a walk-in closet and ample storage, along with a recently updated second full bath and an additional bedroom—great for guests or family. Step outside and enjoy the simple pleasures of country life. Relax under the covered patio, listen to the birds, watch the sun rise and set, and take in the open views. With mature trees, open space, and plenty of privacy, this property is perfect for those who value peace, nature, and room to breathe. A rare opportunity to own a slice of Clark County countryside at a great value. Priced to sell and below appraisal—schedule your showing today!

4 Beds ⋅ 2 Baths ⋅ 25505595 MLS

Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600 square feet, this 4-bedroom, 2-bath home provides plenty of room to spread out. The unfinished basement and one-car attached garage offer great storage, workshop potential, or future expansion. Inside, you'll find a welcoming foyer that opens to a bright, spacious living and dining area filled with natural light from large windows overlooking the countryside. The eat-in kitchen sits at the heart of the home, featuring stainless steel appliances, generous cabinet space, a walk-in pantry, and a cozy fireplace—perfect for gathering after a long day. Just beyond the kitchen is a large bonus room highlighted by charming brick details, ideal for entertaining, a family room, or even a home office or hobby space. The main level includes two roomy bedrooms, an updated full bath, and a convenient laundry room. Upstairs, the private primary bedroom offers a walk-in closet and ample storage, along with a recently updated second full bath and an additional bedroom—great for guests or family. Step outside and enjoy the simple pleasures of country life. Relax under the covered patio, listen to the birds, watch the sun rise and set, and take in the open views. With mature trees, open space, and plenty of privacy, this property is perfect for those who value peace, nature, and room to breathe. A rare opportunity to own a slice of Clark County countryside at a great value. Priced to sell and below appraisal—schedule your showing today!

6239 Old Boonesboro Rd, Winchester

$375,000

Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to detail throughout.The open-concept living area creates the perfect setting for entertaining or relaxing at home, while the well-designed kitchen offers abundant cabinetry, generous workspace, and appliances that convey with the home, making your move that much easier. Buyer to verify listing details. See attached improvements in documents.

3 Beds ⋅ 2 Baths ⋅ 26019273 MLS

Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to detail throughout.The open-concept living area creates the perfect setting for entertaining or relaxing at home, while the well-designed kitchen offers abundant cabinetry, generous workspace, and appliances that convey with the home, making your move that much easier. Buyer to verify listing details. See attached improvements in documents.

125 Amiens Blvd, Winchester

$375,000

Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft room. Home is complimented by a beautiful front staircase as well as a back staircase for added convenience. Home has covered porches on both the front and rear of home to enjoy the beautiful sunrises and sunsets or just sit back and take in the country views from your own 5 acres. Home has a 3-car detached garage and storage shed. Schedule your private showing today.

5 Beds ⋅ 3 Baths ⋅ 25505942 MLS

Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft room. Home is complimented by a beautiful front staircase as well as a back staircase for added convenience. Home has covered porches on both the front and rear of home to enjoy the beautiful sunrises and sunsets or just sit back and take in the country views from your own 5 acres. Home has a 3-car detached garage and storage shed. Schedule your private showing today.

1503 Schollsville Rd, Winchester

$370,000

1.29 acre Commercial Lot zoned B-3 that's slightly elevated with maximum visibility for your business. Ideal location for a gas station, fast food restaurant or retail shop. Lot near Clark Medical Center Hospital. To the south is Lexington Road (US 60), to the west is Floyd Clay Drive, and to the North is Croxton Way. Making three (3) different entrances to enhance accessibility to any business. Very simple access to I-64, major restaurants abundant, most all major shopping chains, a short drive to Lexington, and minutes to downtown Winchester. This lot is stellar for a very successful business.

23015432 MLS

1.29 acre Commercial Lot zoned B-3 that's slightly elevated with maximum visibility for your business. Ideal location for a gas station, fast food restaurant or retail shop. Lot near Clark Medical Center Hospital. To the south is Lexington Road (US 60), to the west is Floyd Clay Drive, and to the North is Croxton Way. Making three (3) different entrances to enhance accessibility to any business. Very simple access to I-64, major restaurants abundant, most all major shopping chains, a short drive to Lexington, and minutes to downtown Winchester. This lot is stellar for a very successful business.

395 Croxton Way, Winchester

$370,000

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

$370,000

Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home offers a warm and inviting atmosphere, blending timeless chcaracter with thougful updates. Move in ready and full of appeal this is one you won't want to miss?

3 Beds ⋅ 3 Baths ⋅ 26014243 MLS

Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home offers a warm and inviting atmosphere, blending timeless chcaracter with thougful updates. Move in ready and full of appeal this is one you won't want to miss?

19 Fontaine Blvd, Winchester

$365,000

Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a renovated eat-in kitchen with a large island, leathered granite countertops, stainless steel appliances, and a gas range. A spacious walk-in pantry adds functionality, while updated windows, recessed lighting, and a new slider door (2025) bring in natural light. The primary suite is a true retreat with a private bath and an expansive walk-in closet. On the opposite wing, you'll find a second primary suite, creating the perfect setup for multi-generational living or hosting long-term guests. Outside, the property continues to impress with two driveways for ample parking, a large usable yard, and a huge detached garage ideal for parking, storage, or a workshop. An updated storage shed (2025) adds even more utility.

4 Beds ⋅ 3 Baths ⋅ 25502189 MLS

Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a renovated eat-in kitchen with a large island, leathered granite countertops, stainless steel appliances, and a gas range. A spacious walk-in pantry adds functionality, while updated windows, recessed lighting, and a new slider door (2025) bring in natural light. The primary suite is a true retreat with a private bath and an expansive walk-in closet. On the opposite wing, you'll find a second primary suite, creating the perfect setup for multi-generational living or hosting long-term guests. Outside, the property continues to impress with two driveways for ample parking, a large usable yard, and a huge detached garage ideal for parking, storage, or a workshop. An updated storage shed (2025) adds even more utility.

114 Mallard Ln, Winchester

$364,900

Are your ready for a lifestyle change? Do you need more space? How about approximately 2800 square feet with four bedrooms and 2-1/2 baths. A nice size corner lot with side entry 2 car garage. Walkout patio, walk in closet, two story entry and gas fireplace are just a few of the features in this home. Recent upgrades include TWO new hot water heaters, UV filtration installed in HVAC, Full privacy fenced back yard recently stained, garage proffesionaly insulated with spray foam, and new steel back insulated garage door. Don't let this one get away. Call today to set up your showing. All info is believed to be accurate. Listing agent is the owner and previous occupent. Directions: From Winchester Bypass turn on to Frontier Way, then left onto Crockett Ct., then left onto Tremont Lane the destination is on your right Latitude: 37.999201 Longitude: -84.224293

4 Beds ⋅ 3 Baths ⋅ 25508633 MLS

Are your ready for a lifestyle change? Do you need more space? How about approximately 2800 square feet with four bedrooms and 2-1/2 baths. A nice size corner lot with side entry 2 car garage. Walkout patio, walk in closet, two story entry and gas fireplace are just a few of the features in this home. Recent upgrades include TWO new hot water heaters, UV filtration installed in HVAC, Full privacy fenced back yard recently stained, garage proffesionaly insulated with spray foam, and new steel back insulated garage door. Don't let this one get away. Call today to set up your showing. All info is believed to be accurate. Listing agent is the owner and previous occupent. Directions: From Winchester Bypass turn on to Frontier Way, then left onto Crockett Ct., then left onto Tremont Lane the destination is on your right Latitude: 37.999201 Longitude: -84.224293

446 Tremont Ln, Winchester

$363,000

comp sale

2 Beds ⋅ 3 Baths ⋅ 25504992 MLS

comp sale

614 S Maple St, Winchester

$360,000

Please give 24 hour's notice. If you've been searching for an immaculate ranch home in a great location, this is one you won't want to miss! Let's start with the updates. This beautifully maintained home features newer heating and cooling, a newer water heater, granite countertops, updated kitchen and appliances, a privacy fence, professional landscaping, exterior lighting, and so much more. Now that I have your attention, let's talk about the home itself. Offering three bedrooms, two full bathrooms, and a spacious bonus room that could easily serve as a fourth bedroom, this home has an incredible layout with plenty of flexibility for your lifestyle. Then there's the outdoor living space! You'll find yourself spending countless mornings and evenings relaxing on the large, covered, screened-in back patio, overlooking your private backyard. It's the perfect spot to enjoy your morning coffee, entertain guests, or simply unwind at the end of the day. With its thoughtful updates, fantastic layout, beautiful outdoor space, and move-in-ready condition, this ranch is truly a home you'll want to see for yourself!

4 Beds ⋅ 2 Baths ⋅ 26024780 MLS

Please give 24 hour's notice. If you've been searching for an immaculate ranch home in a great location, this is one you won't want to miss! Let's start with the updates. This beautifully maintained home features newer heating and cooling, a newer water heater, granite countertops, updated kitchen and appliances, a privacy fence, professional landscaping, exterior lighting, and so much more. Now that I have your attention, let's talk about the home itself. Offering three bedrooms, two full bathrooms, and a spacious bonus room that could easily serve as a fourth bedroom, this home has an incredible layout with plenty of flexibility for your lifestyle. Then there's the outdoor living space! You'll find yourself spending countless mornings and evenings relaxing on the large, covered, screened-in back patio, overlooking your private backyard. It's the perfect spot to enjoy your morning coffee, entertain guests, or simply unwind at the end of the day. With its thoughtful updates, fantastic layout, beautiful outdoor space, and move-in-ready condition, this ranch is truly a home you'll want to see for yourself!

327 Primrose Ln, Winchester

$359,000

Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To compliment the home there is a garage and storage building. Home has many recent improvements and is ready to move in condition.

3 Beds ⋅ 2 Baths ⋅ 26003583 MLS

Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To compliment the home there is a garage and storage building. Home has many recent improvements and is ready to move in condition.

175 Overlooking Dr, Winchester

$359,000

Welcome to your next home in one of Clark County's most sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide generous space for family, guests, or a dedicated home office. At the heart of the home is a massive gourmet kitchen, complete with new granite countertops, all new stainless-steel appliances, and a charming coffee bar. The kitchen opens seamlessly into a spacious, light filled living room enhanced by modern lighting and new ceiling fans—an ideal setting for everyday living and effortless entertaining. Step outside to a large private backyard offering a concrete deck and ample shade—perfect for relaxing, grilling, or watching kids and pets play. The freshly painted attached garage adds versatility, whether you need easy parking or extra storage. Located just one mile from the Winchester Bypass and minutes from Hamburg Pavilion's premier shopping and dining, Shala Mar Estates is a truly family oriented neighborhood with unmatched convenience. Don't miss your chance to own this exceptional home. Call today to schedule your private showing. Owner/Agent

3 Beds ⋅ 2 Baths ⋅ 26005511 MLS

Welcome to your next home in one of Clark County's most sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide generous space for family, guests, or a dedicated home office. At the heart of the home is a massive gourmet kitchen, complete with new granite countertops, all new stainless-steel appliances, and a charming coffee bar. The kitchen opens seamlessly into a spacious, light filled living room enhanced by modern lighting and new ceiling fans—an ideal setting for everyday living and effortless entertaining. Step outside to a large private backyard offering a concrete deck and ample shade—perfect for relaxing, grilling, or watching kids and pets play. The freshly painted attached garage adds versatility, whether you need easy parking or extra storage. Located just one mile from the Winchester Bypass and minutes from Hamburg Pavilion's premier shopping and dining, Shala Mar Estates is a truly family oriented neighborhood with unmatched convenience. Don't miss your chance to own this exceptional home. Call today to schedule your private showing. Owner/Agent

133 Shala-Mar Rue, Winchester

$356,000

Beautifully updated 4 bedroom, 2 bath brick ranch situated on a spacious .55± acre lot in a quiet rural subdivision! This well-maintained home offers comfort, functionality, and plenty of indoor and outdoor space. Features include an attached 2-car garage, detached 2-car garage with heating and air wall unit, 1-car carport, crawlspace, oversized driveway, storage shed, and three outdoor storage buildings providing exceptional space for hobbies, equipment, or workshop use. Inside, you'll find a warm and inviting floor plan with hardwood, laminate, vinyl, and ceramic tile flooring throughout. The updated kitchen features beautiful cabinetry and countertops installed in 2020, stainless appliances, large island, and updated light fixtures throughout the main living areas. Appliances remaining include the refrigerator, oven/range, dishwasher, microwave, washer, and dryer. The spacious primary suite includes a walk-in tiled shower installed in 2020. Major updates provide peace of mind including a new roof in 2022, HVAC system in 2024, and enclosed sunroom addition completed in 2023. Kitchen appliances are all less than 6 years old. Step outside to enjoy the large fenced backyard installed in 2020, ideal for pets, play, gardening, or entertaining. With multiple garages, abundant storage, and a peaceful country-style setting, this property offers space and versatility that's hard to find!

4 Beds ⋅ 2 Baths ⋅ 26010546 MLS

Beautifully updated 4 bedroom, 2 bath brick ranch situated on a spacious .55± acre lot in a quiet rural subdivision! This well-maintained home offers comfort, functionality, and plenty of indoor and outdoor space. Features include an attached 2-car garage, detached 2-car garage with heating and air wall unit, 1-car carport, crawlspace, oversized driveway, storage shed, and three outdoor storage buildings providing exceptional space for hobbies, equipment, or workshop use. Inside, you'll find a warm and inviting floor plan with hardwood, laminate, vinyl, and ceramic tile flooring throughout. The updated kitchen features beautiful cabinetry and countertops installed in 2020, stainless appliances, large island, and updated light fixtures throughout the main living areas. Appliances remaining include the refrigerator, oven/range, dishwasher, microwave, washer, and dryer. The spacious primary suite includes a walk-in tiled shower installed in 2020. Major updates provide peace of mind including a new roof in 2022, HVAC system in 2024, and enclosed sunroom addition completed in 2023. Kitchen appliances are all less than 6 years old. Step outside to enjoy the large fenced backyard installed in 2020, ideal for pets, play, gardening, or entertaining. With multiple garages, abundant storage, and a peaceful country-style setting, this property offers space and versatility that's hard to find!

274 Greenway Dr, Winchester

$355,000

Professional Pictures coming 7/11. Welcome home to this spacious corner-lot property in a highly desirable neighborhood! Designed with family living in mind, this home features two distinct living spaces, perfect for a formal living room and a separate kids' playroom or cozy den. Everyone gets their own space with four generous bedrooms, offering plenty of room for sleep, study, and storage. Enjoy quiet mornings or bug-free evenings on the screened-in porch, which overlooks a nice-sized yard with endless room for kids and pets to play. Don't miss this perfect blend of space, comfort, and functionality for your family! *Buyer to verify all aspects of the listing.

4 Beds ⋅ 3 Baths ⋅ 26017601 MLS

Professional Pictures coming 7/11. Welcome home to this spacious corner-lot property in a highly desirable neighborhood! Designed with family living in mind, this home features two distinct living spaces, perfect for a formal living room and a separate kids' playroom or cozy den. Everyone gets their own space with four generous bedrooms, offering plenty of room for sleep, study, and storage. Enjoy quiet mornings or bug-free evenings on the screened-in porch, which overlooks a nice-sized yard with endless room for kids and pets to play. Don't miss this perfect blend of space, comfort, and functionality for your family! *Buyer to verify all aspects of the listing.

411 Skylark Dr, Winchester

$355,000

Great investment opportunity right in heart Downtown Winchester!!! Welcome to this income producing apartment complex of 8 studio apartments. Two levels of apartments, 4 on the first floor and 4 on the second. Each unit features a living area, full kitchen, and full bathroom. 5 units are currently rented out. The roof was put on 2 years ago. The basement has 2 entrances and could easily be transformed into more units or a laundry area with storage. Conveniently located, close to shops and restaurants. Close to I-64 for quick access to Lexington and surrounding areas.

8 Beds ⋅ 8 Baths ⋅ 26007617 MLS

Great investment opportunity right in heart Downtown Winchester!!! Welcome to this income producing apartment complex of 8 studio apartments. Two levels of apartments, 4 on the first floor and 4 on the second. Each unit features a living area, full kitchen, and full bathroom. 5 units are currently rented out. The roof was put on 2 years ago. The basement has 2 entrances and could easily be transformed into more units or a laundry area with storage. Conveniently located, close to shops and restaurants. Close to I-64 for quick access to Lexington and surrounding areas.

17 W Lexington Ave, Winchester

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