Winchester Homes with Detached Parking Features

Winchester Homes with Detached Parking Features

Welcome to Winchester, Kentucky – a charming city that beautifully blends rich history with modern living. Nestled in Clark County, Winchester is renowned for its warm community spirit and vibrant local culture. With a population that cherishes its heritage, this city is home to stunning historic architecture, lush parks, and a variety of dining and shopping options that cater to every taste.

One of the standout features of homes in Winchester is the availability of detached parking spaces. This is a significant advantage for homeowners, providing convenience and additional storage options. Whether you’re looking for a dedicated space for your vehicles or a workshop for your hobbies, homes with detached parking can meet your needs while enhancing your property’s appeal. Imagine the ease of parking your car just steps away from your front door or having a secure area for recreational vehicles and tools.

Winchester's real estate market offers a diverse range of properties, from charming bungalows to spacious family homes, all designed with comfort and functionality in mind. The neighborhoods are inviting, with tree-lined streets and friendly neighbors, making it an ideal place for families, retirees, and everyone in between.

As you explore Winchester, you’ll discover the perfect blend of small-town charm and modern amenities. With its picturesque surroundings and community-focused lifestyle, Winchester is more than just a place to live; it’s a place to call home. Come experience the warmth and beauty of Winchester, where your dream home with detached parking awaits!

Newest Winchester Homes with Detached Parking Features

$259,900
3 Beds ⋅ 1 Baths ⋅ 26024178 MLS
Welcome to this freshly renovated farmhouse in the heart of Trapp, Kentucky! Blending timeless farmhouse charm with fresh updates, this property is ready for its next chapter. The possibilities are endless—come see all this special home has to offer. An absolute must-see!

11304 Irvine Rd, Winchester
$460,000
3 Beds ⋅ 2 Baths ⋅ 26022948 MLS
Welcome to country living at its finest! This beautifully renovated three-bedroom, two-full-bath ranch home is situated on just over two acres in one of Clark County's most picturesque settings. Offering an exceptional blend of space, comfort, and functionality, this property is sure to impress from the moment you arrive—with a front porch view you'll truly appreciate. The main level features a thoughtfully updated kitchen with ample cabinetry and workspace, opening seamlessly into the dining area for easy entertaining and everyday living. The home has been freshly painted throughout, with numerous updates adding to its appeal and convenience. Step outside to enjoy the added patio, creating an inviting space for relaxing, entertaining, or simply taking in the peaceful surroundings. The partially finished basement provides additional flexible living and workspace, while the oversized two-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop. For even more versatility, the property includes an additional detached one-car garage with electricity already connected—perfect for a workshop, additional storage, or recreational equipment. With beautiful acreage, updates throughout, multiple garage spaces, and a peaceful country setting, this is a property that truly needs to be experienced in person. Come see all that this exceptional Clark County home has to offer!

2195 Pretty Run Rd, Winchester
$175,000
3 Beds ⋅ 1 Baths ⋅ 26022678 MLS
Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

24 Spring St, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ 26022208 MLS
Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

15 Kittison Dr, Winchester
$140,000
2 Beds ⋅ 1 Baths ⋅ 26022182 MLS
Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

108 Franklin Ave, Winchester
$295,000
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
$205,400
2 Beds ⋅ 1 Baths ⋅ 26021605 MLS
606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

606 College St, Winchester
$324,900
3 Beds ⋅ 2 Baths ⋅ 26005152 MLS
Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides privacy with two guest bedrooms on one side of the home and the primary suite on the other, complete with a walk-in closet and en-suite bath. Enjoy the outdoors from the covered front porch or the covered pebble rock patio in the back. Property also includes a 2-car detached carport with a large shed behind it for additional storage. Driveway has a perfect place for an RV. Property is just minutes outside of city limits. The second lot offers its own separate driveway, while the current owners have added a new concrete driveway and block wall going to 1291 Muddy Creek. A rare fine with beautiful views, added privacy and extra space. Thanks to the two lots.--don't miss this unique opportunity.

1291-1299 Muddy Creek Rd, Winchester
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 26020418 MLS
This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are minutes to Hamburg Lexington as well as Winchester and Richmond. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor bathroom, decorative ceilings, custom trim and built ins, finished basement, home gym, movie theatre, basement bar, Large walk-in closets attached to ALL bedrooms, basketball court, shooting range, detached garage with concrete floors and double garage bays. This list is endless. There is an additional 1545 sqft of unfinished space that new buyer can easily customize. Schedule your showing today and view this breathtaking property! Seller is a licensed Realtor in state of KY.

5039 Combs Ferry Rd, Winchester
$484,900
3 Beds ⋅ 2 Baths ⋅ 26020312 MLS
Enjoy country living on approximately seven acres at 919 Elkin Station Road! A welcoming wraparound front porch sets the tone for this spacious three-bedroom, two-bath home featuring beautiful hardwood floors throughout. The kitchen is enhanced by granite countertops, while a charming sunroom offers a cozy place to relax and enjoy the surrounding views. A versatile bonus room is perfect for a home office, playroom, guest space or potential fourth bedroom. The partially finished basement provides even more room to relax and entertain, featuring a bar, pool-table area, separate den area and spacious built-in wall gun safe. Outside, spend summer days by the above-ground pool and surrounding deck, then unwind in the hot tub. A detached two-car garage provides additional parking and storage. The property also includes a 2,880-square-foot barn equipped with electricity and a cistern providing a convenient water source, making it ideal for equipment, storage, hobbies or agricultural use. With abundant indoor and outdoor living space, acreage and exceptional outbuildings, this property offers the privacy and versatility of country living while remaining convenient to Winchester.

919 Elkin Station Rd, Winchester
$189,000
3 Beds ⋅ 1 Baths ⋅ 26020135 MLS
This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

32 Jackson St, Winchester
$785,000
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
Start Your Search