Winchester Homes with Garage Faces Side Parking Features

Winchester Homes with Garage Faces Side Parking Features

Welcome to Winchester, Kentucky—a charming city nestled in Clark County that beautifully blends small-town warmth with modern conveniences. Known for its rich history and vibrant community spirit, Winchester offers a unique lifestyle that appeals to families, retirees, and everyone in between. With its picturesque landscapes, friendly neighborhoods, and a strong sense of community, it’s no wonder that many choose to call this lovely city home.

One of the standout features of homes in Winchester is the availability of properties with side-facing garages. These homes not only provide ample parking space but also enhance the curb appeal of the property. Side parking allows for a clean and organized front yard, showcasing the beauty of your home without the distraction of a garage door. Imagine coming home to a beautifully landscaped garden, with your vehicle tucked neatly out of sight—creating a serene and inviting atmosphere for both residents and guests alike.

Winchester is also conveniently located near major highways, making it easy to access nearby cities while enjoying the tranquility of suburban living. Residents can take advantage of local parks, shopping centers, and a variety of dining options, all within a short drive from home.

Whether you’re looking for a cozy starter home or a spacious family residence, Winchester’s real estate market offers an array of options to suit your needs. Explore the delightful homes with side-facing garages and discover the perfect blend of style, functionality, and community in this charming Kentucky city. Welcome home to Winchester!

Newest Winchester Homes with Garage Faces Side Parking Features

$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
$789,000
3 Beds ⋅ 2 Baths ⋅ 26018078 MLS
**Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses, gardening, recreation, or simply taking in the scenic views, this property is ready for you to make it your own! The detached garage has a second floor office area. There are four other outbuildings for horses, hobbies, or equipment storage. Plenty of fenced areas for horses or other farm animals. The gated entrance provide privacy and security. A rare opportunity to enjoy Kentucky living at its best!

6500 Mount Sterling Rd, Winchester
$165,000
4 Beds ⋅ 3 Baths ⋅ 26008701 MLS
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester
$225,000
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
$775,000
5 Beds ⋅ 3 Baths ⋅ 26007545 MLS
Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home office, or simply room to spread out. The generously sized living area opens seamlessly into the dining area, creating a natural gathering space for those family gatherings or functional for everyday living. With a 42 x 40 metal barn, open pastures and scenic surroundings, this property is ideal for equestrian enthusiasts, hobby farmers, or anyone looking to escape the hustle without sacrificing convenience. Enjoy peaceful mornings, breathtaking sunsets, and room to roam—all within easy reach of Lexington. The home is ready for its next owner to move in and make it their own, Seller is offering a generous flooring allowance with an acceptable offer providing the opportunity to refinish the existing hardwood floors and replace carpeting. Buyer to verify all aspects of the property and school districts.

465 Morris Rd, Winchester
$2,750,000
8 Beds ⋅ 8 Baths ⋅ 26009631 MLS
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester
$445,500
3 Beds ⋅ 3 Baths ⋅ 26009944 MLS
This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester
$375,000
4 Beds ⋅ 3 Baths ⋅ 26008931 MLS
Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.

382 S Main St, 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
$515,000
3 Beds ⋅ 2 Baths ⋅ 26009385 MLS
Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that practically begs for cozy evenings and lively gatherings alike. The kitchen shines with quartz countertops, stainless steel appliances, and classic shaker cabinetry, while a large pantry keeps everything organized and within reach. Elegant wood plantation blinds frame the views throughout, adding warmth and character to every room. Three bedrooms and two full bathrooms provide comfortable living for any household. The primary suite features a beautifully tiled shower that transforms your daily routine into something a little more luxurious. A bonus room situated above the garage offers flexible space perfect for a home office, playroom, or creative studio. Outside, the screened-in porch invites you to enjoy peaceful mornings surrounded by nature, and a detached workshop stands ready for projects big and small. The oversized utility room, complete with a mop sink, makes tackling life's messier moments refreshingly simple. Nearby Buffalo Ridge Ranch adds even more outdoor adventure to your doorstep. Properties like this — where thoughtful craftsmanship meets wide-open acreage — simply do not come along every day. Schedule your private showing and discover what country living at its finest truly feels like.

935 Stoner-Ephesus Rd, 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.

137 Eastridge Dr, Winchester
$1,349,000
4 Beds ⋅ 5 Baths ⋅ 26013734 MLS
Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom. Head upstairs to the spacious 680sqft recreation room with its own full bathroom and attic storage access. Step outside to your large, spacious covered patio, personal inground pool with spa and sunken inground fire pit for endless entertaining. 3-Car garage offers ample storage. The 2670sqft Walk-out basement is a blank canvas with endless opportunities. Basement can be finished by builder at buyer's discretion. Some additional selections may be available. LUXURY, SPACE and PRIVACY just minutes from town.

1200 Craig Xing, Winchester
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