Winchester Homes with Attached Parking Features

Winchester Homes with Attached Parking Features

Welcome to Winchester, Kentucky, a charming city nestled in the heart of Clark County, where history and modern living blend seamlessly. Known for its picturesque landscapes and vibrant community, Winchester offers a unique lifestyle that appeals to families, retirees, and professionals alike. With a rich history dating back to the late 18th century, the city boasts a quaint downtown area filled with local shops, delightful eateries, and cultural attractions that celebrate its heritage.

One of the standout features of Winchester’s real estate market is the availability of homes with attached parking. Imagine the convenience of stepping directly from your home into your vehicle, especially during those unpredictable Kentucky weather days. Properties in Winchester often come equipped with garages or carports, providing not only shelter for your vehicles but also additional storage space for seasonal items, tools, or recreational gear.

The residential neighborhoods in Winchester are characterized by tree-lined streets and a welcoming atmosphere, making it an ideal place to raise a family or enjoy a peaceful retirement. With easy access to parks, schools, and recreational facilities, residents can enjoy an active lifestyle while still appreciating the tranquility of suburban living.

Whether you’re searching for a cozy starter home or a spacious family residence, Winchester’s real estate market has something to offer everyone. Embrace the charm of this beautiful city and discover the perfect home with attached parking features that will make your life a little easier and a lot more enjoyable. Come and experience the warmth of Winchester, where community spirit thrives and home is truly where the heart is!

Newest Winchester Homes with Attached Parking Features

119 Winterberry Cir, Winchester
$439,900
3 Beds ⋅ 2 Baths ⋅ 26028916 MLS
Welcome to 119 Winterberry Court! Offered at $439,900, this beautiful all-brick home is situated on a spacious corner lot and offers 3 bedrooms, 2 full bathrooms, and 2,276 square feet of living space, including the finished sunroom! Step inside to find beautiful hardwood flooring, an inviting open-concept living area, and a spacious kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a large island perfect for entertaining. The primary suite offers a tray ceiling and a beautifully remodeled bathroom complete with a custom tiled walk-in shower, double vanity, and generous closet space. One of the home's standout features is the finished sunroom, complete with its own mini-split heating and cooling system, providing a comfortable space to enjoy year-round! Outside, you'll find a fenced backyard, patio area, mature landscaping, and a two-car attached garage. This home has seen numerous improvements since 2019, including a new roof, replacement of all windows, two new garage doors and openers, remodeled bathrooms, a new fence, and 6-inch gutters. Additional improvements include professional crawlspace encapsulation in 2025 (see listing attachments for full details) and a brand-new HVAC system installed in 2026! Conveniently located less than half a mile from the interstate and approximately 20 minutes from both Hamburg and Paris, this home offers the perfect combination of space, updates, and accessibility. Schedule your private showing today!

119 Winterberry Cir, Winchester
314 Botts Ct, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 26028838 MLS
This stunning remodeled 3 bedroom 2 bathroom all brick ranch in Verna Hills subdivision is a must see! From the moment you walk in, your only concern is moving in. The following items have been done: new drywall in 50%+ of the home done to completely remove all wallpaper, new roof, soffit, gutters (2025), new hot water heater, new custom back sliding glass door, crawlspace completely waterproofed with vapor barrier and newly installed sump pump, brand new privacy fence, all new vinyl flooring and paint, completely upgraded kitchen with custom cabinetry, backsplash, quartz countertops, and stainless steel appliances, 2 custom designed bathrooms with custom tile and trim work and all new custom light fixtures. Schedule a showing soon to see this great home!

314 Botts Ct, Winchester
285 Rose Dr, Winchester
$434,000
3 Beds ⋅ 2 Baths ⋅ 26028699 MLS
This charming 3-bedroom, 2-bath home in the desirable Mallard Place subdivision has been lovingly maintained and is ready for your personal touch. A few cosmetic updates will make this one truly shine, but the big ticket items have already been handled: 4 year old roof, new hot water heater and a geothermal heating and cooling system that keeps monthly utility costs remarkably low. Relax year-round in the bright patio room overlooking the nice backyard, perfect for morning coffee or evening gatherings. The full unfinished walk-out basement offers endless possibilities for future living space, recreation or storage. Don't miss the opportunity to add your style to a solid, well-cared-for home. Conveniently located near Colby Road and McClure Road with easy access to Winchester amenities. This is a must see!

285 Rose Dr, Winchester
410 Fairholme Way, Winchester
$484,900
4 Beds ⋅ 3 Baths ⋅ 26028690 MLS
Brand new and ready for you to move in now! Be the very first to call this stunning 4 bedroom, new construction ranch home where modern luxury meets everyday living. Every surface is fresh, every finish was thoughtfully chosen, and every evening brings golf course view sunsets from the front porch. Inside, an open-concept layout welcomes you with soaring vaulted ceilings and a fireplace anchoring the spacious living room. The kitchen pairs style with function: quartz countertops, a built-in nook ready for your coffee bar, and a generous walk-in pantry with floating shelves and wine cooler. A dedicated dining area under its own vaulted ceiling sets the stage for weeknight dinners and easy entertaining alike. The private primary suite is a true retreat, with a spa-like en-suite featuring a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom floor plan adds privacy, with three additional bedrooms and two more full baths offering flexible space for guests, hobbies, or a home office. Out back, the covered patio is ready for morning coffee, quiet evenings, or weekend get-togethers. The tall garage is a standout bonus, giving you room for vertical storage and even more everyday functionality. And the location is hard to beat. Just outside charming downtown Winchester, you're minutes from local shops and restaurants, with quick access to I-64 for an easy commute. No waiting on a build and no surprises from a previous owner. Just brand-new living, ready today!

410 Fairholme Way, Winchester
131 Teal Ln, Winchester
$617,000
3 Beds ⋅ 4 Baths ⋅ 26028684 MLS
If you're looking for space, character, and a home with plenty of possibilities, this one deserves a look! This beautiful ranch-style home offers a full basement, two garages, and an inviting floor plan with impressive architectural details throughout. Step inside and you'll immediately notice the gorgeous hardwood flooring, detailed trim work, and spacious living areas. The great room features a vaulted ceiling, brick fireplace, and beautiful custom built-in cabinetry. The kitchen offers an abundance of rich wood cabinetry, granite countertops, stainless steel appliances, double ovens, and a breakfast area. A formal dining room showcases elegant wainscoting, crown molding, and a beautiful chandelier, adding character and charm. The screened-in porch provides another great space to relax and enjoy the outdoors. The full basement offers additional space and flexibility, while the two garages provide plenty of room for vehicles, storage, or hobbies. With its generous living spaces, beautiful woodwork, and thoughtful design, this home has so much to offer. Come see the possibilities for yourself! Rony Jo Ballou Broker Auctioneer.

131 Teal Ln, Winchester
323 Skylark Dr, Winchester
$424,500
5 Beds ⋅ 4 Baths ⋅ 26028682 MLS
You have to see this one! Spacious 5-bedroom, 4-bath home priced under recent appraisal! The primary bedroom and two other bedrooms are on the main level. This wonderful home sits on a large lot with a great backyard perfect for entertaining, play and relaxation. Conveniently located close to the Winchester bypass and shopping, you'll enjoy easy commutes and everyday errands. The basement offers flexible space for so much more- think game room, home office, gym, or all three. Plus, a separate garage keeps the lawnmower and yard equipment neatly out of the way. With generous living space throughout, this home truly offers room for everyone. Don't miss this fantastic value in a prime location- schedule your showing today.

323 Skylark Dr, Winchester
200 Evergreen Dr, Winchester
$457,900
4 Beds ⋅ 3 Baths ⋅ 26028668 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** The Paddock offers approximately 1,986 square feet of thoughtfully designed main-level living with 3 bedrooms, 2.5 baths and a versatile flex room suitable for a home office or optional fourth bedroom. The open kitchen, dining and great-room layout features 10-foot ceilings, bar seating and an expanded walk-in pantry. A private primary suite includes a spacious walk-in closet and well-appointed bath, while two additional bedrooms and a second full bath provide comfortable accommodations for family or guests. Covered front and rear outdoor spaces and an attached 2-car garage complete the main level. The home is planned over an unfinished walkout basement, providing excellent storage and future finishing potential, with plumbing stubbed for a future basement bath. Floor plan, square footage, finishes and construction details are subject to final plans, specifications and selections. Images are conceptual renderings.

200 Evergreen Dr, Winchester
225 Evergreen Dr, Winchester
$469,925
3 Beds ⋅ 2 Baths ⋅ 26028670 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** Discover the perfect blend of timeless design, modern comfort, and future expansion potential in The Mulberry, a thoughtfully designed ranch home offering well-appointed main-level living plus a full unfinished walkout basement ready for your personal vision. The open-concept floor plan is designed for both everyday living and entertaining, featuring a spacious Great Room with a gas fireplace, a bright dining area, and a beautifully designed kitchen complete with a large center island, walk-in pantry, abundant cabinetry, and dedicated oven/microwave wall cabinet. The adjoining rear covered porch extends your living space outdoors, creating the perfect setting for relaxing or entertaining while overlooking your backyard. The private primary suite serves as a peaceful retreat with a generous walk-in closet, dual vanity, oversized walk-in shower, soaking tub, and convenient access to the laundry room through the owner's hall. On the opposite side of the home, two additional bedrooms, a full bath, and a dedicated office provide comfortable accommodations for family, guests, or working from home.

225 Evergreen Dr, Winchester
230 Evergreen Dr, Winchester
$462,738
3 Beds ⋅ 2 Baths ⋅ 26028671 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** Experience the perfect blend of modern farmhouse style and peaceful country living with The Equestrian floor plan, a beautifully designed proposed new construction home in the desirable Locust Hill Acres subdivision. This thoughtfully crafted ranch floor plan features 3 bedrooms, 2 full baths, and an open-concept design ideal for both everyday living and entertaining. The home also includes an unfinished walkout basement, offering incredible flexibility for future expansion, additional living space, a recreation room, home gym, workshop, or abundant storage. The spacious great room flows seamlessly into the dining area and chef-inspired kitchen, complete with a large center island, pantry, abundant cabinetry, and premium finishes throughout. The private owner's suite serves as a relaxing retreat with a generous walk-in closet and a luxurious ensuite bath featuring dual vanities and a tiled walk-in shower. Two additional bedrooms provide comfortable accommodations for family, guests, or a dedicated home office. Step outside to enjoy the oversized cathedral-ceiling covered rear deck, perfect for entertaining or taking in the peaceful surroundings of your one-acre homesite. A welcoming covered front porch with exposed timber accents and a charming breezeway connecting the home to the detached two-car garage adds timeless character and exceptional curb appeal. Enjoy the tranquility of rural living while remaining just minutes from downtown Winchester and an easy commute to Lexington. Pricing and specifications are subject to final plans, selected options, and lot availability. Photos and renderings are for illustrative purposes only and may depict optional features or upgrades not included in the base price.

230 Evergreen Dr, Winchester
121 Bay Hill Dr, Winchester
$279,900
3 Beds ⋅ 3 Baths ⋅ 26028464 MLS
Looking for a Short Term Rental or Mid Term Rental? Want room to spread out and space to make your own? Welcome to 121 Bay Hill Drive in Winchester, offering three bedrooms, two and a half baths, and over 2,700 square feet of finished living space. With room for a possible fourth bedroom and multiple flexible spaces, you can create the home offices, sewing room, craft room, or gaming room you've been looking for. Whether you need space to work, unwind, or enjoy your favorite hobbies, this home offers plenty of possibilities. A beautifully landscaped lot adds to the appeal, while the location approximately two minutes from the interstate makes commuting and everyday travel convenient. Come explore how this versatile home can fit your next chapter!

121 Bay Hill Dr, 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
444 Wellington Way, Winchester
$309,900
4 Beds ⋅ 3 Baths ⋅ 26027910 MLS
This 4 bedroom, 3 bath home is quietly nestled within the Colby Ridge subdivision just off Bypass road. Updates can be seen throughout. Spacious great room, open living/ kitchen areas, large master bedroom with on-suite and walk-in closet, fully fenced yard and so much more. Schedule your showing today!

444 Wellington Way, Winchester
Start Your Search

How much is your home worth?

Get instant property value now!