$285,000 Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\! 3 Beds ⋅ 2 Baths ⋅ 26019908 MLS Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\! 108 Milwood Dr, Winchester
$498,000 Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing. 4 Beds ⋅ 3 Baths ⋅ 26019848 MLS Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing. 1780 Stoner-Ephesus Rd, 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
$380,000 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
$369,000 This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker 3 Beds ⋅ 2 Baths ⋅ 26019263 MLS This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker 11 Stoney Brook Dr Unit 1, Winchester
$272,900 Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting and a small refrigerator-ideal for grilling, hosting friends, or enjoying quiet evenings at home. You'll also appreciate the screened-in back patio, offering a peaceful place to unwind while overlooking the beautifully landscaped yard. The property features mature fruit trees, including a peach and apple trees, adding both charm and seasonal enjoyment. With attractive landscaping surrounding the home and thoughtful outdoor amenities, this property is ready for you to move-in and enjoy. Don't miss the opportunity to make this wonderful home yours! 3 Beds ⋅ 2 Baths ⋅ 26019259 MLS Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting and a small refrigerator-ideal for grilling, hosting friends, or enjoying quiet evenings at home. You'll also appreciate the screened-in back patio, offering a peaceful place to unwind while overlooking the beautifully landscaped yard. The property features mature fruit trees, including a peach and apple trees, adding both charm and seasonal enjoyment. With attractive landscaping surrounding the home and thoughtful outdoor amenities, this property is ready for you to move-in and enjoy. Don't miss the opportunity to make this wonderful home yours! 316 Buffalo Trce, Winchester
$429,000 Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle. 3 Beds ⋅ 3 Baths ⋅ 26019133 MLS Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle. 322 Calmes Blvd, Winchester
$410,000 Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home. 4 Beds ⋅ 2 Baths ⋅ 26017258 MLS Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home. 351 Boone Ave, Winchester
$178,000 Welcome home to this beautifully updated 2-bedroom, 1-bath home offering 1,061 square feet of comfortable living space! The renovated kitchen features soft-close shaker cabinets and granite countertops, while durable luxury vinyl plank flooring flows throughout the home for a fresh, modern feel. Outside, you'll find a spacious, fully fenced backyard complete with a storage shed providing extra space for tools and outdoor equipment. Spend your evenings relaxing in the backyard or take a short walk to nearby Legacy Grove Park. An attached carport adds the convenience of covered off street parking. Just minutes from downtown, this home offers the perfect blend of modern updates, outdoor space, and a convenient location. Whether you're a first-time buyer, looking to downsize, or searching for a turn key investment opportunity, this move-in-ready home is one you won't want to miss! Seller is a licensed real estate agent in Kentucky. 2 Beds ⋅ 1 Baths ⋅ 26019033 MLS Welcome home to this beautifully updated 2-bedroom, 1-bath home offering 1,061 square feet of comfortable living space! The renovated kitchen features soft-close shaker cabinets and granite countertops, while durable luxury vinyl plank flooring flows throughout the home for a fresh, modern feel. Outside, you'll find a spacious, fully fenced backyard complete with a storage shed providing extra space for tools and outdoor equipment. Spend your evenings relaxing in the backyard or take a short walk to nearby Legacy Grove Park. An attached carport adds the convenience of covered off street parking. Just minutes from downtown, this home offers the perfect blend of modern updates, outdoor space, and a convenient location. Whether you're a first-time buyer, looking to downsize, or searching for a turn key investment opportunity, this move-in-ready home is one you won't want to miss! Seller is a licensed real estate agent in Kentucky. 17 Waveland Ave, Winchester
$239,995 Enjoy small town living! This 3-bedroom 2 bath budget friendly home is ready and waiting for new owners. The unique loft space adds additional space to make it your own. Sitting on just under a third of an acre which will provide a lot of outdoor space to enjoy with friends and family. The backyard is fenced for convenience and privacy. Run from the routine of renting and enjoy home ownership in this cute home. Less than 5 minutes to I64 and close to Winchester dining and shopping. 3 Beds ⋅ 2 Baths ⋅ 26018986 MLS Enjoy small town living! This 3-bedroom 2 bath budget friendly home is ready and waiting for new owners. The unique loft space adds additional space to make it your own. Sitting on just under a third of an acre which will provide a lot of outdoor space to enjoy with friends and family. The backyard is fenced for convenience and privacy. Run from the routine of renting and enjoy home ownership in this cute home. Less than 5 minutes to I64 and close to Winchester dining and shopping. 22 Apache Trl, Winchester
$465,000 Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today! 3 Beds ⋅ 2 Baths ⋅ 26018911 MLS Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today! 1024 Flanagan Station Rd, Winchester
$524,900 OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home. 3 Beds ⋅ 3 Baths ⋅ 26018460 MLS OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home. 275 Runnymeade Dr, Winchester
$269,900 SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!! 3 Beds ⋅ 1 Baths ⋅ 26016881 MLS SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!! 2379 Big Stoner Rd, Winchester
$749,900 Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today! 3 Beds ⋅ 3 Baths ⋅ 26017698 MLS Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today! 2180 Big Stoner Rd, Winchester
$350,000 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
$225,000 This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss! 3 Beds ⋅ 4 Baths ⋅ 26017061 MLS This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss! 128 Abbeywood Ct, Winchester
$409,500 215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season. 3 Beds ⋅ 2 Baths ⋅ 26016762 MLS 215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season. 215 Delaplain Rd, Winchester
$329,900 Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and countertops, modern electrical and plumbing fixtures, a newer driveway, and more giving you a move-in ready feel from day one. Enjoy outdoor living with a spacious backyard, newer deck and beautiful landscaping. This home offers the perfect blend of space, style, and convenience. Schedule your private showing today! 4 Beds ⋅ 2 Baths ⋅ 26006679 MLS Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and countertops, modern electrical and plumbing fixtures, a newer driveway, and more giving you a move-in ready feel from day one. Enjoy outdoor living with a spacious backyard, newer deck and beautiful landscaping. This home offers the perfect blend of space, style, and convenience. Schedule your private showing today! 228 Holiday Rd, Winchester
$235,000 Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods. 4 Beds ⋅ 1 Baths ⋅ 26013563 MLS Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods. 120 Windsor Dr, Winchester
$549,900 Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with all stainless appliances including a gas range for cooking those delicious meals. The large kitchen overlooking the great room offers the convenience of an eat in bar area, delightful dining space, a huge hidden pantry and a unique kitchen niche to make it your own unique space for a possible coffee bar. This home is all about convenience and privacy with the split bedroom concept. Lots of space in the primary bedroom for your king size bed plus a nice sitting area. You will love the huge primary bath with stylish custom tile and the adjoining generous sized closet for the fashionista. In edition there are two guest bedrooms with a full bathroom. There is an additional flex room that makes a great office space or a 4th bedroom. The large laundry area and drop zone is an added convenient feature to the home. From enjoying your morning coffee, evening relaxation or outdoor gatherings the large covered back patio is the place to be with the outdoor fireplace. You will love the large 2-car oversized garage. This home has so much to offer! Convenient to local shopping, restaurants, I64, 17 miles to Man o' War Blvd Lexington and 28 miles to Bluegrass Airport. Schedule your tour today to check out this beautiful home. Now is your chance to own this nearly new home. 3 Beds ⋅ 2 Baths ⋅ 26010352 MLS Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with all stainless appliances including a gas range for cooking those delicious meals. The large kitchen overlooking the great room offers the convenience of an eat in bar area, delightful dining space, a huge hidden pantry and a unique kitchen niche to make it your own unique space for a possible coffee bar. This home is all about convenience and privacy with the split bedroom concept. Lots of space in the primary bedroom for your king size bed plus a nice sitting area. You will love the huge primary bath with stylish custom tile and the adjoining generous sized closet for the fashionista. In edition there are two guest bedrooms with a full bathroom. There is an additional flex room that makes a great office space or a 4th bedroom. The large laundry area and drop zone is an added convenient feature to the home. From enjoying your morning coffee, evening relaxation or outdoor gatherings the large covered back patio is the place to be with the outdoor fireplace. You will love the large 2-car oversized garage. This home has so much to offer! Convenient to local shopping, restaurants, I64, 17 miles to Man o' War Blvd Lexington and 28 miles to Bluegrass Airport. Schedule your tour today to check out this beautiful home. Now is your chance to own this nearly new home. 108 Bella Shae Way, Winchester
$312,000 Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance. 3 Beds ⋅ 3 Baths ⋅ 26008021 MLS Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance. 200 Dubuy Dr, Winchester
$274,500 The ranch home at 116 Sturbridge Lane in Winchester, KY has 3 bedrooms, 2 full bathrooms, an eat-in kitchen, large living room, laundry room and 2 car garage. The home has been lovingly cared for and features multiple upgrades. Situated behind Lowe's, it offers easy access to dining, shopping, the by-pass, and medical & educational facilities. 3 Beds ⋅ 2 Baths ⋅ 26011782 MLS The ranch home at 116 Sturbridge Lane in Winchester, KY has 3 bedrooms, 2 full bathrooms, an eat-in kitchen, large living room, laundry room and 2 car garage. The home has been lovingly cared for and features multiple upgrades. Situated behind Lowe's, it offers easy access to dining, shopping, the by-pass, and medical & educational facilities. 116 Sturbridge Ln, Winchester
$289,000 Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000. 3 Beds ⋅ 2 Baths ⋅ 26007779 MLS Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000. 54 Locust Dr, Winchester
$785,000 This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of your outdoor toys. The detached garage has water and electrical service with a workshop area and also a large unfinished loft area for additional storage or possibly create the space into a recreation space. The lovely custom home with over 3300 square feet has hardwood flooring throughout, crown molding, tall ceilings, and built in shelving in the family room. Lots of natural light in the living area with the sunburst arched windows overlooking the property. The home has a convenient split bedroom concept. The spacious primary bedroom has an ensuite bath with a soaking tub and separate vanities and a large closet. The upstairs has an additional full bathroom with 2 large flex rooms with one currently being used as a 4th bedroom. The additional flex room would be a great space for a workout room or office. This well-maintained country home offers the convenience of Winchester shopping and dining and also only 8 miles to I64 and I75. If you have been looking for a home with a quiet country setting this is the perfect property. 4 Beds ⋅ 3 Baths ⋅ 26012036 MLS This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of your outdoor toys. The detached garage has water and electrical service with a workshop area and also a large unfinished loft area for additional storage or possibly create the space into a recreation space. The lovely custom home with over 3300 square feet has hardwood flooring throughout, crown molding, tall ceilings, and built in shelving in the family room. Lots of natural light in the living area with the sunburst arched windows overlooking the property. The home has a convenient split bedroom concept. The spacious primary bedroom has an ensuite bath with a soaking tub and separate vanities and a large closet. The upstairs has an additional full bathroom with 2 large flex rooms with one currently being used as a 4th bedroom. The additional flex room would be a great space for a workout room or office. This well-maintained country home offers the convenience of Winchester shopping and dining and also only 8 miles to I64 and I75. If you have been looking for a home with a quiet country setting this is the perfect property. 7300 Old Boonesboro Rd, Winchester
$550,000 Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours! 3 Beds ⋅ 3 Baths ⋅ 24025578 MLS Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours! 107 Bella Shae Way, Winchester
$329,900 This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel leveled deck. Street dead ends to a large owned lot with tons of green space. Schedule your showing now while you can! 4 Beds ⋅ 3 Baths ⋅ 26008249 MLS This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel leveled deck. Street dead ends to a large owned lot with tons of green space. Schedule your showing now while you can! 110 Powe Dr, Winchester
$2,999,000 Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter. 6 Beds ⋅ 5 Baths ⋅ 25507353 MLS Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter. 3049 Ironworks Rd, Winchester
$499,900 One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home! 4 Beds ⋅ 3 Baths ⋅ 26010312 MLS One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home! 16 Manor Dr, Winchester
$825,000 Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life. 3 Beds ⋅ 3 Baths ⋅ 24025579 MLS Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life. 111 Bella Shae Way, Winchester
$670,000 Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood! 3 Beds ⋅ 2 Baths ⋅ 24025580 MLS Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood! 113 Bella Shae Way, Winchester