Winchester Kentucky homes for sale starting at Fifty Thousand Dollars

$665,000 - Winchester, KY

414 Alexis Way Winchester, KY - Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added convenience. The open-concept kitchen flows seamlessly into the great room, which is highlighted by a gas log fireplace and built-in cabinetry. The kitchen is a chef's dream, featuring a large island, a cozy breakfast area, and a walk-in pantry for ample storage. The Alexis also includes a formal dining room, perfect for entertaining, along with a convenient drop zone with a bench for everyday use. With 9-foot ceilings and luxury vinyl plank flooring throughout, this home combines modern elegance with functionality. A 2-car attached garage completes this exquisite floor plan. Let'c customize your dream home in Mallard Cove with CP Builders!

$650,000 - Winchester, KY

2085 Hancock Valley Drive Winchester, KY - Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY! Discover country living at its finest with this beautiful 3-bedroom, 3-bathroom home set on nearly 5 acres of picturesque land. Featuring beautiful hardwood floors, a finished basement, and plenty of space for entertaining and friends, this property is designed for comfort and social gatherings. Enjoy the in-ground pool, pole barn, and updated roof, HVAC, and appliances, making this home both charming and well-maintained. Bring your horses—this home welcomes them! Conveniently located just minutes from the Hamburg area, you'll have easy access to shopping, dining, and entertainment while still embracing the tranquility of open space. Don't miss out on this unique opportunity—schedule your showing today!

$645,000 - Winchester, KY

439 Lynnway Drive Winchester, KY - Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen complete with Green Egg, Blackstone, mini fridge, and gas fireplace. The crown jewel of this outdoor space... the stunning 18x36 Grecian in-ground pool accompanied by a custom stone gas fire pit and hot tub. Whether you're binging the latest blockbuster in the home theatre or enjoying a serene morning by the pool, this home offers a blend of relaxation and entertainment. This residence isn't just a place to live; it's a place to thrive and create unforgettable memories. Ready to dive into your new lifestyle? Your dream home awaits! ** Contingent w/ 24hr Kick-Out in place**

$645,000 - Winchester, KY

106 Bella Shae Way Winchester, KY - Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The gourmet kitchen boasts a large island, perfect for entertaining, and a walk-in pantry for ample storage. A cozy fireplace with gas logs adds a touch of warmth and ambiance to the living room. The first floor also includes a dedicated dining room, a study perfect for working from home, a separate laundry room, and a convenient half bath for guests. Upstairs, you'll find three additional generously sized bedrooms and a two full bathrooms, providing ample space for family and guests. The two-story living room creates an impressive and airy feel throughout the home. Experience the joy of building your dream home with CP Builders.

$635,000 - Winchester, KY

422 Alexis Way Winchester, KY - 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!

$625,000 - Winchester, KY

424 Alexis Way Winchester, KY - 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.

$599,500 - Winchester, KY

102 Bella Shae Way Winchester, KY - Introducing the Stonewall plan—a stunning brick and stone ranch ideally positioned on a corner lot in Mallard Cove. This 4 bedroom, 2 full bath home with a side-entry garage offers timeless curb appeal and high-end features throughout. The thoughtfully designed layout includes a spacious living room with vaulted ceilings, arched and lighted built-ins, and a gas fireplace with a floor-to-ceiling stone surround. The gourmet kitchen is a showstopper, featuring a large island with waterfall-edge Taj Mahal quartzite, matching countertops and backsplash, custom ceiling-height soft-close cabinetry, under-cabinet lighting, farmhouse sink, walk-in pantry, and a custom hood. The luxurious primary suite offers tray ceilings, a wainscoting accent wall, soaking tub, walk-in tile shower, double vanity, and a generous walk-in closet. One of the four bedrooms includes a tray ceiling and closet, making it ideal for a home office or guest room. Additional highlights include a brick floor foyer, custom drop zone with built-ins off the garage entry, a private covered back patio with stamped concrete, and a large unfinished space above the garage for future expansion or storage.

$579,000 - Winchester, KY

110 White Conkwright Road Winchester, KY - Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

$550,000 - Winchester, KY

107 Bella Shae Way Winchester, KY - 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!

$550,000 - Winchester, KY

31 West Hickman Street Winchester, KY - We are honored to present this rare opportunity to purchase a beautiful, historic property in the heart of Winchester, Kentucky. Built in 1814 and upon complete renovations in the 1980s and again the past 5 years, this property is a wonderful blend of historic charm with modern upgrades and high quality piece of mind. Zoned as P-1, it can function as a commercial property or as residential and the current configuration is already conducive to both as it sits today with features doubling as office/bedrooms, fully equipped kitchen, patio space, closets, 2.5 bathrooms. Other qualities include hardwood floors, fire places, high ceilings, large windows, second floor deck space, outdoor patio, large lawn and parking. Truly an oasis ripe for living, working, entertaining, or as an investment opportunity!

Winchester, Kentucky listings for sale

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