Winchester Homes with Garage Faces Rear Parking Features

Winchester Homes with Garage Faces Rear Parking Features

Welcome to Winchester, Kentucky—a charming city nestled in the heart of Clark County, where history meets modern living. Known for its vibrant community spirit and picturesque landscapes, Winchester offers a perfect blend of small-town charm and contemporary conveniences. With its historic downtown, delightful local shops, and a variety of parks, residents enjoy a lifestyle that is both relaxing and engaging.

One of the standout features of homes in Winchester is the rear-facing garage parking. This design not only enhances the aesthetic appeal of the neighborhood but also provides added convenience and security for homeowners. Imagine coming home to a beautifully designed residence where your garage is tucked away from the street, allowing for a clean and uncluttered front view. This thoughtful layout also maximizes outdoor space, giving you room for landscaping or leisure activities.

Winchester’s real estate market is diverse, with homes that cater to various tastes and budgets. Whether you’re seeking a cozy starter home or a spacious family residence, you’ll find properties that boast modern amenities and charming architectural details. The rear garage feature is particularly appealing for those who value privacy and a streamlined look.

Living in Winchester means embracing a lifestyle filled with community events, outdoor adventures, and a strong sense of belonging. With its friendly atmosphere and beautiful surroundings, it’s no wonder that so many are choosing to call Winchester home. Explore the possibilities today and discover the perfect home that suits your needs in this delightful Kentucky city!

Newest Winchester Homes with Garage Faces Rear Parking Features

$254,900
3 Beds ⋅ 3 Baths ⋅ 26022409 MLS
Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

127 Bay Hill Dr, Winchester
$300,000
4 Beds ⋅ 2 Baths ⋅ 26021718 MLS
Classic character and generous living space come together at 224 W Hickman Street in Winchester. This single-family residence offers 4 bedrooms, 2 full bathrooms, and approximately 2,479 square feet, providing a flexible layout with room for a variety of everyday living needs. The home's substantial interior footprint creates opportunities for comfortable gathering spaces, private bedrooms, a home office, hobbies, or additional storage. Conveniently located in Winchester, this property offers an appealing combination of space and established residential character.

224 W Hickman St, Winchester
$229,900
3 Beds ⋅ 2 Baths ⋅ 26021639 MLS
This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

106 Quail Ridge Rd, 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
$289,900
4 Beds ⋅ 3 Baths ⋅ 26020651 MLS
Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.

428 Waycross Dr, Winchester
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester
$2,999,000
6 Beds ⋅ 5 Baths ⋅ 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester
$359,000
3 Beds ⋅ 3 Baths ⋅ 26013780 MLS
Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

309 Gallahadion Ct, Winchester
$519,900
4 Beds ⋅ 5 Baths ⋅ 26013378 MLS
Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality. Owner/Agent

600 Boone Ave, Winchester
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