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Welcome to 119 Winterberry Court! Offered at $439,900, this beautiful all-brick home is situated on a spacious corner lot and offers 3 bedrooms, 2 full bathrooms, and 2,276 square feet of living space, including the finished sunroom! Step inside to find beautiful hardwood flooring, an inviting open-concept living area, and a spacious kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a large island perfect for entertaining. The primary suite offers a tray ceiling and a beautifully remodeled bathroom complete with a custom tiled walk-in shower, double vanity, and generous closet space. One of the home's standout features is the finished sunroom, complete with its own mini-split heating and cooling system, providing a comfortable space to enjoy year-round! Outside, you'll find a fenced backyard, patio area, mature landscaping, and a two-car attached garage. This home has seen numerous improvements since 2019, including a new roof, replacement of all windows, two new garage doors and openers, remodeled bathrooms, a new fence, and 6-inch gutters. Additional improvements include professional crawlspace encapsulation in 2025 (see listing attachments for full details) and a brand-new HVAC system installed in 2026! Conveniently located less than half a mile from the interstate and approximately 20 minutes from both Hamburg and Paris, this home offers the perfect combination of space, updates, and accessibility. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26028916 MLS

Welcome to 119 Winterberry Court! Offered at $439,900, this beautiful all-brick home is situated on a spacious corner lot and offers 3 bedrooms, 2 full bathrooms, and 2,276 square feet of living space, including the finished sunroom! Step inside to find beautiful hardwood flooring, an inviting open-concept living area, and a spacious kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a large island perfect for entertaining. The primary suite offers a tray ceiling and a beautifully remodeled bathroom complete with a custom tiled walk-in shower, double vanity, and generous closet space. One of the home's standout features is the finished sunroom, complete with its own mini-split heating and cooling system, providing a comfortable space to enjoy year-round! Outside, you'll find a fenced backyard, patio area, mature landscaping, and a two-car attached garage. This home has seen numerous improvements since 2019, including a new roof, replacement of all windows, two new garage doors and openers, remodeled bathrooms, a new fence, and 6-inch gutters. Additional improvements include professional crawlspace encapsulation in 2025 (see listing attachments for full details) and a brand-new HVAC system installed in 2026! Conveniently located less than half a mile from the interstate and approximately 20 minutes from both Hamburg and Paris, this home offers the perfect combination of space, updates, and accessibility. Schedule your private showing today!

119 Winterberry Cir, Winchester

$484,900

Brand new and ready for you to move in now! Be the very first to call this stunning 4 bedroom, new construction ranch home where modern luxury meets everyday living. Every surface is fresh, every finish was thoughtfully chosen, and every evening brings golf course view sunsets from the front porch. Inside, an open-concept layout welcomes you with soaring vaulted ceilings and a fireplace anchoring the spacious living room. The kitchen pairs style with function: quartz countertops, a built-in nook ready for your coffee bar, and a generous walk-in pantry with floating shelves and wine cooler. A dedicated dining area under its own vaulted ceiling sets the stage for weeknight dinners and easy entertaining alike. The private primary suite is a true retreat, with a spa-like en-suite featuring a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom floor plan adds privacy, with three additional bedrooms and two more full baths offering flexible space for guests, hobbies, or a home office. Out back, the covered patio is ready for morning coffee, quiet evenings, or weekend get-togethers. The tall garage is a standout bonus, giving you room for vertical storage and even more everyday functionality. And the location is hard to beat. Just outside charming downtown Winchester, you're minutes from local shops and restaurants, with quick access to I-64 for an easy commute. No waiting on a build and no surprises from a previous owner. Just brand-new living, ready today!

4 Beds ⋅ 3 Baths ⋅ 26028690 MLS

Brand new and ready for you to move in now! Be the very first to call this stunning 4 bedroom, new construction ranch home where modern luxury meets everyday living. Every surface is fresh, every finish was thoughtfully chosen, and every evening brings golf course view sunsets from the front porch. Inside, an open-concept layout welcomes you with soaring vaulted ceilings and a fireplace anchoring the spacious living room. The kitchen pairs style with function: quartz countertops, a built-in nook ready for your coffee bar, and a generous walk-in pantry with floating shelves and wine cooler. A dedicated dining area under its own vaulted ceiling sets the stage for weeknight dinners and easy entertaining alike. The private primary suite is a true retreat, with a spa-like en-suite featuring a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom floor plan adds privacy, with three additional bedrooms and two more full baths offering flexible space for guests, hobbies, or a home office. Out back, the covered patio is ready for morning coffee, quiet evenings, or weekend get-togethers. The tall garage is a standout bonus, giving you room for vertical storage and even more everyday functionality. And the location is hard to beat. Just outside charming downtown Winchester, you're minutes from local shops and restaurants, with quick access to I-64 for an easy commute. No waiting on a build and no surprises from a previous owner. Just brand-new living, ready today!

410 Fairholme Way, Winchester

$617,000

If you're looking for space, character, and a home with plenty of possibilities, this one deserves a look! This beautiful ranch-style home offers a full basement, two garages, and an inviting floor plan with impressive architectural details throughout. Step inside and you'll immediately notice the gorgeous hardwood flooring, detailed trim work, and spacious living areas. The great room features a vaulted ceiling, brick fireplace, and beautiful custom built-in cabinetry. The kitchen offers an abundance of rich wood cabinetry, granite countertops, stainless steel appliances, double ovens, and a breakfast area. A formal dining room showcases elegant wainscoting, crown molding, and a beautiful chandelier, adding character and charm. The screened-in porch provides another great space to relax and enjoy the outdoors. The full basement offers additional space and flexibility, while the two garages provide plenty of room for vehicles, storage, or hobbies. With its generous living spaces, beautiful woodwork, and thoughtful design, this home has so much to offer. Come see the possibilities for yourself! Rony Jo Ballou Broker Auctioneer.

3 Beds ⋅ 4 Baths ⋅ 26028684 MLS

If you're looking for space, character, and a home with plenty of possibilities, this one deserves a look! This beautiful ranch-style home offers a full basement, two garages, and an inviting floor plan with impressive architectural details throughout. Step inside and you'll immediately notice the gorgeous hardwood flooring, detailed trim work, and spacious living areas. The great room features a vaulted ceiling, brick fireplace, and beautiful custom built-in cabinetry. The kitchen offers an abundance of rich wood cabinetry, granite countertops, stainless steel appliances, double ovens, and a breakfast area. A formal dining room showcases elegant wainscoting, crown molding, and a beautiful chandelier, adding character and charm. The screened-in porch provides another great space to relax and enjoy the outdoors. The full basement offers additional space and flexibility, while the two garages provide plenty of room for vehicles, storage, or hobbies. With its generous living spaces, beautiful woodwork, and thoughtful design, this home has so much to offer. Come see the possibilities for yourself! Rony Jo Ballou Broker Auctioneer.

131 Teal Ln, Winchester

$200,000

3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester

$439,000

This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

3 Beds ⋅ 3 Baths ⋅ 26000113 MLS

This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

$769,900

Beautiful custom home built in 2024 with high-end upgrades throughout. Surrounded by mature trees on over 3 acres with mountain views, this home offers a beautiful mix of privacy, quality, and convenience. From the moment you walk up, you can see the quality of craftsmanship. A large front porch welcomes you with double front doors. Once inside, you're immediately drawn to the soaring ceilings, wood-planked ceiling, wall of black-framed windows, and abundant natural light. The open loft overlooking the great room adds to the unique design and makes the space feel even more impressive. The quality and craftsmanship throughout this home truly stand out and are increasingly hard to find in today's market. You'll find solid wood doors, engineered hardwood floors, custom cabinetry, quartz countertops, designer lighting, and thoughtful details throughout. The primary suite is located on the first floor and features a large walk-in closet and spa-like bathroom. The primary bath includes a beautiful marble tile wet room and freestanding soaking tub, creating a relaxing retreat. The setting is one of the things that makes this property so special. Mature trees surrounding the home give it a peaceful, private feel while still keeping you within an easy drive of Lexington. Outdoor living is just as impressive, with approximately 815 square feet of covered porches, including a screened porch accessible directly from both the primary bedroom and great room. It's the perfect place for morning coffee, quiet evenings, or gatherings with friends. The home is just 1.5 miles from Exit 10 on the Mountain Parkway, approximately 29 minutes from Hamburg Pavilion, 22 minutes from the Red River Gorge, and about 19 minutes from Kroger in Winchester. The oversized 24x30 garage, built in 2026, provides plenty of room for vehicles, storage, a workshop, or recreational equipment. Outside, the 3+ acre lot offers plenty of room to enjoy the property as it is or create your own outdoor space, with room for a future pool and entertaining area. If you've been looking for a newer home with acreage and privacy without feeling too far removed from everything, this is one you'll want to see. If you're tired of seeing the same cookie-cutter homes, this one is refreshingly different. The home has even been selected by Architectural Designs to be featured in a client album on their website.

3 Beds ⋅ 3 Baths ⋅ 26026365 MLS

Beautiful custom home built in 2024 with high-end upgrades throughout. Surrounded by mature trees on over 3 acres with mountain views, this home offers a beautiful mix of privacy, quality, and convenience. From the moment you walk up, you can see the quality of craftsmanship. A large front porch welcomes you with double front doors. Once inside, you're immediately drawn to the soaring ceilings, wood-planked ceiling, wall of black-framed windows, and abundant natural light. The open loft overlooking the great room adds to the unique design and makes the space feel even more impressive. The quality and craftsmanship throughout this home truly stand out and are increasingly hard to find in today's market. You'll find solid wood doors, engineered hardwood floors, custom cabinetry, quartz countertops, designer lighting, and thoughtful details throughout. The primary suite is located on the first floor and features a large walk-in closet and spa-like bathroom. The primary bath includes a beautiful marble tile wet room and freestanding soaking tub, creating a relaxing retreat. The setting is one of the things that makes this property so special. Mature trees surrounding the home give it a peaceful, private feel while still keeping you within an easy drive of Lexington. Outdoor living is just as impressive, with approximately 815 square feet of covered porches, including a screened porch accessible directly from both the primary bedroom and great room. It's the perfect place for morning coffee, quiet evenings, or gatherings with friends. The home is just 1.5 miles from Exit 10 on the Mountain Parkway, approximately 29 minutes from Hamburg Pavilion, 22 minutes from the Red River Gorge, and about 19 minutes from Kroger in Winchester. The oversized 24x30 garage, built in 2026, provides plenty of room for vehicles, storage, a workshop, or recreational equipment. Outside, the 3+ acre lot offers plenty of room to enjoy the property as it is or create your own outdoor space, with room for a future pool and entertaining area. If you've been looking for a newer home with acreage and privacy without feeling too far removed from everything, this is one you'll want to see. If you're tired of seeing the same cookie-cutter homes, this one is refreshingly different. The home has even been selected by Architectural Designs to be featured in a client album on their website.

330 Spencer Ln, Winchester

$675,000

Rare opportunity to purchase a new construction home in the country on almost 5 acres in Clark County! Brand new modern farmhouse featuring 4 bedrooms, 3.5 baths, front and rear covered porches with stamped concrete floors and stained wood ceilings, 2 car garage, gas vented fireplace, and much more! From the inviting high vaulted ceiling foyer you will notice the tray ceilings with faux beams in the formal dining area and the spacious great room, which leads to the functionally designed kitchen and pantry. Enjoy the privacy of a secluded main-level en-suite bedroom, thoughtfully positioned away from the homes primary living spaces. The spacious bath offers a soaking tub, tiled shower, separated dual vanities, access to the massive upscale dual access laundry room, and windows with a beautiful view! Up the stairs above the garage you will find another private bedroom with full bath. The opposite side of the home contains 2 more bedrooms with a full bath between. It is truly a perfect layout to maximize the use of every square foot! Other features include LP smart siding, quality stainless appliances including a lower cabinet microwave, custom vented range hood, under cabinet lighting, disposal, quartz countertops throughout the entire house! It is uncommon to find this many upgrades at this price point! There is a full length concrete storm shelter under the front porch accessed via the crawlspace door for added piece of mind. The 4.82 acre lot features level areas ready to build your barn or detached workshop, a nice flat backyard area ready to install your pool, and plenty of room to fence off for your 4 legged friends of any kind! Located only 6 minutes (4.3 miles) from I-64, this location gives you the country life you want while still being easily accessed from Winchester or Mt Sterling and provides an easy 25 minute drive to Lexington. As an option, you can take the beautiful scenic drive out Ecton Rd to access the home if you prefer. Property is under a contingent contract with a 72 hour kick out clause.

4 Beds ⋅ 4 Baths ⋅ 26026085 MLS

Rare opportunity to purchase a new construction home in the country on almost 5 acres in Clark County! Brand new modern farmhouse featuring 4 bedrooms, 3.5 baths, front and rear covered porches with stamped concrete floors and stained wood ceilings, 2 car garage, gas vented fireplace, and much more! From the inviting high vaulted ceiling foyer you will notice the tray ceilings with faux beams in the formal dining area and the spacious great room, which leads to the functionally designed kitchen and pantry. Enjoy the privacy of a secluded main-level en-suite bedroom, thoughtfully positioned away from the homes primary living spaces. The spacious bath offers a soaking tub, tiled shower, separated dual vanities, access to the massive upscale dual access laundry room, and windows with a beautiful view! Up the stairs above the garage you will find another private bedroom with full bath. The opposite side of the home contains 2 more bedrooms with a full bath between. It is truly a perfect layout to maximize the use of every square foot! Other features include LP smart siding, quality stainless appliances including a lower cabinet microwave, custom vented range hood, under cabinet lighting, disposal, quartz countertops throughout the entire house! It is uncommon to find this many upgrades at this price point! There is a full length concrete storm shelter under the front porch accessed via the crawlspace door for added piece of mind. The 4.82 acre lot features level areas ready to build your barn or detached workshop, a nice flat backyard area ready to install your pool, and plenty of room to fence off for your 4 legged friends of any kind! Located only 6 minutes (4.3 miles) from I-64, this location gives you the country life you want while still being easily accessed from Winchester or Mt Sterling and provides an easy 25 minute drive to Lexington. As an option, you can take the beautiful scenic drive out Ecton Rd to access the home if you prefer. Property is under a contingent contract with a 72 hour kick out clause.

1477 Sewell Shop Rd, Winchester

$544,900

Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.

5 Beds ⋅ 4 Baths ⋅ 26021642 MLS

Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.

130 Winterberry Cir, Winchester

$785,000

Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.

5 Beds ⋅ 3 Baths ⋅ 26019610 MLS

Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.

217 Wades Mill Rd, Winchester

$160,000

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

4 Beds ⋅ 3 Baths ⋅ 26008701 MLS

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester

$209,000

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

3 Beds ⋅ 2 Baths ⋅ 26011961 MLS

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$2,750,000

Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

8 Beds ⋅ 8 Baths ⋅ 26009631 MLS

Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester

$325,000

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

4 Beds ⋅ 2 Baths ⋅ 26008225 MLS

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

443 S Maple St, Winchester

$415,000

Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

3 Beds ⋅ 2 Baths ⋅ 26015824 MLS

Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

187 Hawthorne Dr, Winchester

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