Winchester Homes with Detached Garage Parking Features

Winchester Homes with Detached Garage Parking Features

Welcome to Winchester, Kentucky – a charming city nestled in the heart of Clark County, where small-town charm meets modern living. Known for its rich history and vibrant community, Winchester offers a delightful blend of picturesque landscapes, friendly neighbors, and a strong sense of pride among its residents. With a population that appreciates both tradition and innovation, this city is an ideal place to call home.

One of the standout features of homes in Winchester is the availability of properties with detached garage parking. Imagine stepping out of your beautifully designed home and into your own private garage, providing not just convenience but also an extra layer of security for your vehicles and belongings. These detached garages often offer additional storage space, making it easier to keep your home organized and clutter-free.

Winchester’s real estate market boasts a variety of homes, many of which are thoughtfully designed to cater to both families and individuals. Whether you’re seeking a cozy starter home or a spacious residence for a growing family, you’ll find properties that suit your needs. The presence of detached garages adds to the appeal, allowing residents to enjoy the benefits of functional outdoor space while enhancing the overall aesthetic of their homes.

Beyond the properties, Winchester is rich in amenities, with local parks, shopping, and dining options just a stone's throw away. The community hosts various events throughout the year, fostering a tight-knit atmosphere that welcomes newcomers with open arms.

Explore the enchanting homes in Winchester with detached garage parking and discover why so many people are proud to call this city their home!

Newest Winchester Homes with Detached Garage Parking Features

843 Ford Hampton Rd, Winchester
$540,000
5 Beds ⋅ 3 Baths ⋅ 26030232 MLS
Enjoy peaceful country living on 9.09 acres, just off Boonesboro Road with convenient access to both Winchester and Richmond! Surrounded by beautiful wooded scenery, this spacious 5-bedroom, 2.5-bath home offers plenty of privacy and room to spread out. The main level features hardwood flooring, a welcoming living room, a kitchen with granite countertops and stainless steel appliances, a dining area, and access to the screened-in back porch. You'll also find three bedrooms on the main level, including the primary suite, while upstairs offers two generously sized additional bedrooms and a half bath. Step outside to the covered, screened-in back porch, updated in 2025, where you can relax and enjoy the peaceful wooded surroundings. The finished walkout basement provides even more flexible living space, perfect for a second living area, recreation room, or entertaining. The property also features a detached garage, carport, and a mix of cleared and wooded acreage. The sellers have enjoyed hunting on the property, with deer frequently captured on their trail cameras (see photos)! Major improvements include a new roof in 2021, HVAC units in 2022, remodeled bathrooms, added insulation, and new carpet in the primary suite and on steps. With its easy access to town, this property offers the space and privacy of rural living without sacrificing convenience!

843 Ford Hampton Rd, Winchester
7440 Bybee Rd, Winchester
$519,900
5 Beds ⋅ 3 Baths ⋅ 26029059 MLS
*Owner Agent Welcome to this spacious 2023-built, manufactured home situated on 6.54 beautiful acres in Winchester, Kentucky. Offering 5 bedrooms and 3 full bathrooms, this home provides plenty of space for family, guests, and comfortable everyday living. The property combines the convenience of a newer home with the beauty and privacy of acreage. The land features a natural spring, adding a unique country-living feature and providing an additional natural water resource on the property. A detached one-car garage provides valuable space for parking, storage, hobbies, or a workshop. With 6.54 acres, there's plenty of room to enjoy the outdoors, garden, hobby farm, animals such as horses, goats, chickens or turkeys, have recreational space, or simply take in the peaceful surroundings. The property also offers very limited restrictions. The only known restriction is that no obstruction may be placed across the easement located along the rear of the property such as gate, fence etc., giving the new owner considerable flexibility in enjoying and utilizing the land. If you've been searching for a newer 5-bedroom home on acreage with a natural spring, detached garage, privacy, and limited restrictions, this property offers a rare combination of features in the Winchester area. Within 20 minutes of Richmond and 30 minutes of Lexington. Driveway easement at very rear of property. Utility easement for water through property with water meter near road. LISTING AGENT OWNS PROPERTY

7440 Bybee Rd, Winchester
26 Holiday Rd, Winchester
$255,000
3 Beds ⋅ 1 Baths ⋅ 26028523 MLS
Convenient, comfortable, and ready for its next owner! This 3-bedroom, 1-bath ranch home is located in the heart of Winchester and offers easy one-level living with a low-maintenance floor plan. Inside, you'll find comfortable living spaces with freshly cleaned carpets and a home that's ready to move into and make your own. A newer roof provides added peace of mind, while the fenced backyard offers plenty of space for pets, kids, entertaining, or simply enjoying the outdoors. One of the property's best features is the detached 2-car garage with electric, providing excellent space for parking, storage, a workshop, or hobbies. With its central Winchester location, fenced backyard, oversized garage space, and manageable one-level layout, 26 Holiday Road is a great opportunity for a first-time buyer, someone looking to downsize, or anyone searching for an affordable, low-maintenance home. Schedule your private showing today!

26 Holiday Rd, Winchester
5039 Combs Ferry Rd, Winchester
$2,299,000
5 Beds ⋅ 4 Baths ⋅ 26028074 MLS
Experience exceptional craftsmanship, privacy and resort-style living on over 12 acres in the highly desired Combs Ferry area of Clark County. Quietly tucked away yet conveniently located just 15 minutes from Hamburg in Lexington, as well as Winchester and Richmond, this extraordinary custom home was built in 2022 and offers 6,284 finished square feet, plus an additional 1,545 square feet of unfinished space ready for the next owner to customize. From the moment you enter, the quality and attention to detail are unmistakable. Andersen 400 Series windows and doors, decorative ceilings, custom trim and built-ins, engineered hardwood flooring, quartz countertops and designer lighting are featured throughout. The spacious kitchen is a true centerpiece, showcasing custom cabinetry, soft-close doors and drawers, under-cabinet lighting, a hidden walk-in pantry, double ovens, built-in microwave and a 5-burner gas range with built-in Thermador appliances. The main-level primary suite is a private retreat, complete with decorative beams, a stacked-stone gas fireplace, double vanities, soaking tub, expansive walk-in closet and an oversized tiled pass-through shower featuring dual shower heads and a centered rain head. Large walk-in closets accompany every bedroom, providing exceptional storage throughout. The finished lower level expands the possibilities with a home gym, dedicated movie theater with projector and equipment, home office/bonus room, wet bar with granite countertops, wine and beverage refrigerators and dishwasher, plus an additional bedroom with egress window, full bathroom, and walk-in closet. Multiple unfinished areas and the additional 1,545 square feet provide tremendous potential for future customization. Step outside and discover your own private entertainment destination. The 45,000-gallon oversized heated chlorine pool features a tanning ledge, deep-end swim ledge, fountain, LED lighting and energy-efficient variable-speed pump. Enjoy evenings around the custom outdoor fireplace, with the convenience of a dedicated outdoor bathroom. The property also includes a basketball court, shooting range, and detached garage with concrete floors and double garage bays. Additional thoughtful features include a formal dining room with custom moldings, laundry room with built-in cabinetry, mudroom/drop zone with built-ins and cubbies, spray foam insulation, three all-electric HVAC systems, and two 60-gallon water heaters. This is far more than a home; it is a custom-built private estate designed for everyday luxury, entertaining, recreation and relaxation, with room to make it uniquely your own. The combination of acreage, exceptional construction, extensive amenities and convenient location is truly rare. Schedule your private showing today and experience this breathtaking property firsthand. Seller is a licensed Realtor in Kentucky.

5039 Combs Ferry Rd, Winchester
2100 Irvine Rd Unit 40391, Winchester
$1,125,000
3 Beds ⋅ 4 Baths ⋅ 26026878 MLS
Tucked away behind private gates on 28 beautiful acres, this one-of-a-kind cabin offers the perfect blend of privacy, luxury, and country living. Step inside to a stunning open-concept living, dining, and kitchen area designed for gathering and entertaining. The kitchen is a showstopper with custom cabinetry, quartz countertops, a waterfall island, top-of-the-line appliances, and a spacious walk-in pantry. Off the kitchen on the right wing of the house there is a mudroom area with half bathroom, followed by the primary suite. The main-level primary suite is a true retreat, very spacious bedroom area with a private sunroom and direct access to the patio and in-ground pool, walk-in closet and laundry closet. The bathroom features a soaking tub and a tiled walk-in shower. Upstairs, you'll find an additional spacious bedroom with built-in bunk beds, a walk-in closet, and full bath. The left wing of the home provides ideal in-law or guest quarters featuring its own kitchen, open concept living and bedroom area with fireplace, walk-in closet, full bath with walk-in shower, and private exterior entrance. Outside is where this property truly sets itself apart. Enjoy your own private oasis with an in-ground pool surrounded by picturesque acreage. The backyard also includes a "she shed" currently used as a workout room, chicken coop, run-in shed, and 30x33 detached garage. This property features an AKC-inspected kennel facility with 14 indoor/outdoor runs, an office, a grooming area, a bathing area, an open work space, half bathroom and a fenced exercise area. Another 6-hole kennel with overhangs. The remaining property features 7 paddocks, 5 run-in sheds, multiple fenced pastures with run-in sheds and water. Bring the horses, cows, dogs—and even the in-laws! This is an animal lover's dream with room to live, work, play, and enjoy the peace of the countryside, all while being just minutes from I-64 and approximately 24 minutes from Downtown Lexington. The possibilities for this property are endless, and it is a truly special property that has to be experienced in person!

2100 Irvine Rd Unit 40391, Winchester
405 Nick Ln, Winchester
$280,000
2 Beds ⋅ 1 Baths ⋅ 26022030 MLS
Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors. The home has new plumbing, as well as new wiring. A brand-new 30x40 metal garage on a concrete slab provides excellent space for vehicles, equipment, storage, or hobbies. An additional workshop area next to the garage offers even more room for projects and workspace. With 13 beautiful acres, usable land, new outbuildings, and a convenient location, this property offers a great opportunity to enjoy country living while staying close to town. Schedule your showing today!

405 Nick Ln, Winchester
14 Cook Ave, Winchester
$209,000
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
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