Winchester Homes with Basement Parking Features

Winchester Homes with Basement Parking Features

Welcome to Winchester, Kentucky – a hidden gem nestled in the heart of Clark County. Known for its rich history and vibrant community, Winchester offers a perfect blend of small-town charm and modern conveniences. With its picturesque streets, friendly neighborhoods, and a strong sense of community, this city is an ideal place to call home.

Winchester is steeped in history, with beautiful architecture that tells the story of its past. The downtown area is bustling with local shops, delightful eateries, and cultural attractions that reflect the city’s unique character. Outdoor enthusiasts will love the nearby parks and recreational facilities, providing ample opportunities for hiking, biking, and family picnics.

If you’re considering a move to this charming city, you’ll be pleased to discover a variety of homes that cater to diverse lifestyles. One standout feature of many properties in Winchester is the availability of homes with basement parking. These homes not only offer the convenience of protected parking but also provide additional storage space and potential for future development. Imagine the ease of accessing your vehicle without braving the elements or the peace of mind that comes with having a secure place for your belongings.

Whether you’re a first-time homebuyer or looking to settle down, Winchester’s real estate market has something for everyone. With its welcoming community, rich history, and homes equipped with desirable features like basement parking, Winchester is more than just a place to live – it’s a place to thrive. Come explore what makes this city so special, and discover your dream home in Winchester today!

Newest Winchester Homes with Basement Parking Features

705 W Lexington Ave, Winchester
$525,000
6 Beds ⋅ 5 Baths ⋅ 26029637 MLS
Welcome to 705 West Lexington Avenue, where historic charm, modern improvements, and exceptional investment potential come together in one remarkable property. Offering approximately 5,427 square feet on a generous approximate 0.61-acre lot, this distinctive Winchester property presents a rare opportunity to capitalize on substantial renovations already underway while bringing your own vision to life. Behind its timeless architectural character, you'll discover an impressive transformation in progress. Significant improvements have already been made, including updated kitchen and bathrooms, giving the next owner a valuable head start toward completing this extraordinary property. Generously proportioned rooms, distinctive architectural details, and an expansive floor plan create an exceptional canvas for a spectacular private residence or potential investment venture. While additional renovations and finishing touches remain, the groundwork has been laid for something truly special. An added bonus? An attached one-and-a-half-bedroom apartment offering exciting rental income potential! Whether you're seeking supplemental income, accommodations for extended family, or additional flexibility, this unique feature adds another dimension of value and opportunity. Previously identified as B-3 (Highway Business) zoned, the property may also present possibilities for commercial or mixed-use applications, subject to verification and applicable approvals. Its prominent location along West Lexington Avenue, convenient to downtown Winchester and Lexington, further enhances its appeal. Opportunities with this combination of size, character, improvements, income potential, and versatility are not easily found! For the visionary homeowner, savvy investor, or entrepreneur seeking their next project, 705 West Lexington Avenue offers the chance to finish an exciting transformation and unlock exceptional possibilities. The vision has begun. The opportunity is yours. Schedule your private showing and discover what this remarkable property could become!

705 W Lexington Ave, 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
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
47 Cherokee Ct, Winchester
$289,900
3 Beds ⋅ 2 Baths ⋅ 26028007 MLS
Charming Brick Ranch with Beautiful Outdoor Living! Welcome home to this inviting brick ranch offering timeless charm, comfortable living, and plenty of space to make your own! Featuring 3 bedrooms, 2 full bathrooms, and a full walk-out basement, this home offers a versatile layout with endless possibilities. Enjoy the warmth and character of the mature trees surrounding the property, along with a covered front porch that creates the perfect welcome. The screened-in porch provides an ideal spot to enjoy your morning coffee, unwind in the evenings, or entertain family and friends while taking in the peaceful outdoor setting. Inside, you'll find granite countertops and fresh paint that give the home a clean, refreshed feel. A brand-new roof adds extra peace of mind for the next owner. With classic brick construction, inviting outdoor spaces, and a full walk-out basement offering additional potential, this property is a wonderful opportunity to find the comfort, charm, and space you've been looking for. Don't miss your chance to make this home your own!

47 Cherokee Ct, Winchester
600 College St, Winchester
$215,000
3 Beds ⋅ 2 Baths ⋅ 26026485 MLS
Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

600 College St, Winchester
609 W Barlow Dr, Winchester
$375,000
4 Beds ⋅ 2 Baths ⋅ 26026446 MLS
Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, Winchester
1255 The Ridings, Winchester
$775,000
6 Beds ⋅ 4 Baths ⋅ 26026145 MLS
Welcome home to this spacious 6-bedroom, 3.5-bath home located in The Ridings—an equestrian-friendly neighborhood offering miles of designated riding trails! The main level features an inviting open-concept kitchen and living area with a cozy gas fireplace, built-ins, and direct access to the covered back deck, perfect for relaxing, entertaining, and watching sunsets. A half bath and laundry area complete the main floor. Upstairs, you'll find the spacious primary suite, three additional bedrooms, and another full bath. The finished walk-out lower level offers incredible flexibility with a second living area opening to a brand-new patio, two additional bedrooms—one currently used as a playroom has an attached bathroom which could be used as a second primary suite—a full a butlers pantry, and plenty of unfinished storage. It's an ideal setup for guests, extended family, or additional living space. Outside, the property is fully enclosed with four-plank horse fencing and additional wire fencing, giving both horses and four-legged family members room to safely enjoy the outdoors. An attached flex space with its own separate rear entrance makes the perfect man cave, hobby room, home gym, or private office. A detached garage with convenient backyard access provides additional storage for your mower, equipment, and more. Enjoy peaceful country-style living while remaining convenient to everything—approximately 13 miles to Hamburg, 18 miles to downtown Lexington, 16 miles to I-75, and just 5 miles to I-64. With generous living space, a versatile walk-out basement, fenced grounds, and access to miles of riding trails, this property offers a lifestyle that's hard to find!

1255 The Ridings, Winchester
1400 Craig Xing, Winchester
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 26023265 MLS
Magnificent Home sitting on 2.446 Acres, Fantastic Location --Great Views on this 4 Bedroom, 4 Bath Brick Home with over 5,600 Sq. Ft. of Living space. This has a Huge Primary Bedroom with walk in Shower, 2 closets, Large Formal Dining Rm,--Stone Fireplace, Large Sun room with lots of Windows, Another Primary Bedroom upstairs w/Full Bath, Large Finished Basement, with Mother's in Law Quarters. Don't Miss this Great opportunity--Come se this huge Magnificent Home-- Buyer to measure for exact sq.ft of Home Home is vacant and nearing Completion.

1400 Craig Xing, Winchester
2195 Pretty Run 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
148 Hidden Grove Ln, Winchester
$169,000
2 Beds ⋅ 2 Baths ⋅ 26022926 MLS
Unique Kentucky Riverfront retreat with fascinating history! This elevated 2-bedroom, 1.5 bath home was originally constructed from two wood rail cars, giving it a one-of-a kind character you won't find anywhere else. Thoughtfully updated with new windows, roof, HVAC and an updated shower, plus a spacious new deck perfect for relaxing and enjoying the beautiful river setting. Whether you are looking for a full-time residence, weekend retreat, or investment property, this charming riverfront property offers a wonderful opportunity to enjoy the beauty of Kentucky River living!

148 Hidden Grove Ln, Winchester
127 Bay Hill Dr, Winchester
$249,000
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
132 Lana Ln, Winchester
$699,000
4 Beds ⋅ 5 Baths ⋅ 26022150 MLS
MOTIVATED SELLERS. This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a partially finished basement with a bathroom.

132 Lana Ln, Winchester
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