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$379,000
4 Beds ⋅ 3 Baths ⋅ 26015608 MLS
Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

107 Hibiscus Ln, Winchester
$340,000
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
$155,900
1 Beds ⋅ 2 Baths ⋅ 26007407 MLS
Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible potential to create something truly special. While its in good condition it is ready for some TLC, the price reflects the opportunity to build equity and customize to your taste. Whether you're looking to flip, rent, or make this your forever home, this property is packed with promise. Bring your vision and make it shine again! Opportunities like this don't come around often, so schedule your showing today!!!

101 Alabama St, Winchester
$258,900
2 Beds ⋅ 1 Baths ⋅ 26013194 MLS
Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

955 Right Angle Rd, Winchester
$625,000
3 Beds ⋅ 3 Baths ⋅ 24025584 MLS
Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile shower, and soaking tub. The Castleton offers plenty of room to live and entertain, with a separate study, a formal dining room, and a half bath for guests. The open kitchen boasts a large island, pantry, and breakfast nook, flowing seamlessly into the inviting great room with a cozy gas log fireplace. Nine-foot ceilings and luxury vinyl plank flooring enhance the home's modern elegance throughout. With plenty of storage and convenient features like a separate utility room, this home combines both functionality and style. Come make the Castleton your dream home with CP Builders, where comfort, quality, and design come together perfectly.

424 Alexis Way, Winchester
$700,000
3 Beds ⋅ 2 Baths ⋅ 24025582 MLS
Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for entertaining, featuring a large island, walk-in pantry, and seamless flow into the great room, complete with a cozy gas log fireplace. The luxurious primary suite offers a walk-in closet, double vanities, and a tile shower with a soaking tub for ultimate relaxation. Nine-foot ceilings and luxury vinyl plank flooring throughout enhance the home's bright, airy feel. Additional highlights include a separate utility room and an unfinished walkout basement, providing endless possibilities for expansion. The Merango offers the perfect blend of functionality, elegance, and comfort. Let's customize your dream home in Mallard Cove with CP Builders!

415 Alexis Way, Winchester
$519,900
4 Beds ⋅ 5 Baths ⋅ 26013378 MLS
Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality. Owner/Agent

600 Boone Ave, Winchester
$320,000
4 Beds ⋅ 3 Baths ⋅ 26009835 MLS
Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.

38 N Burns Ave, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ 26007260 MLS
Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

103 Southern Ct, Winchester
$309,900
3 Beds ⋅ 3 Baths ⋅ 26014026 MLS
Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

335 Newcastle Ln, Winchester
$274,500
3 Beds ⋅ 2 Baths ⋅ 26011465 MLS
Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and plenty of room for family and friends to gather. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy an oversized backyard complete with a charming white picket fence — perfect for children, pets, gardening, or hosting outdoor entertaining. Whether you're a first time buyer or searching for your forever home, this property offers comfort, convenience, and character all in one. Call today for more information or to schedule your private showing. Note: Offer to Purchase with Contingency and Kick-out Clause. Buyer cannot perform without the sale of current property.

137 Eastridge Dr, Winchester
$319,900
3 Beds ⋅ 2 Baths ⋅ 26013010 MLS
Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The completely renovated kitchen boasts new cabinetry, gorgeous granite countertops, and new stainless appliances, making it perfect for cooking, entertaining, and everyday living. Enjoy mornings on the covered front porch and evenings in the fenced backyard with a deck, ideal for relaxing or hosting friends and family. If you are looking for low maintenance property, one level living and a home ready to move straight into, look no further! Stylish updates, great outdoor spaces, and a classic all-brick construction, situated on a large corner lot......Don't miss this one!

23 Windridge Dr, Winchester
$420,000
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
$635,000
4 Beds ⋅ 3 Baths ⋅ 24025583 MLS
Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower, and double vanities. The open-concept kitchen and great room are perfect for entertaining, complete with a gas log fireplace, large kitchen island, and walk-in pantry. The home also includes a formal dining room, half bath, and a separate utility room for added convenience. Nine-foot ceilings and luxury vinyl plank flooring throughout create a seamless, modern feel. With ample space, thoughtful design, and beautiful finishes, the Denver is the perfect place to call home. Come custom build the Denver plan with CP Builders in Mallard Cove!

422 Alexis Way, Winchester