Winchester Homes with Basement Parking Features

Winchester Homes with Basement Parking Features

Welcome to Winchester, Kentucky – a charming city that beautifully blends small-town warmth with modern conveniences. Nestled in Clark County, Winchester is known for its rich history, vibrant community, and picturesque landscapes. With its historic downtown area, you’ll find a delightful mix of local shops, restaurants, and cultural attractions that make this city a wonderful place to call home.

One of the standout features of homes in Winchester is the availability of properties with basement parking. Imagine the convenience of having your vehicle secured in a spacious basement, protected from the elements while also providing easy access to your home. These homes not only offer practical parking solutions but also add an extra layer of safety and privacy.

Winchester’s real estate market is diverse, catering to a variety of lifestyles and budgets. Whether you’re a first-time homebuyer or looking to upgrade, you’ll find an array of options that suit your needs. Many homes with basement parking feature open floor plans, modern amenities, and beautiful outdoor spaces, perfect for entertaining or enjoying a quiet evening at home.

As a resident of Winchester, you’ll enjoy a strong sense of community, excellent schools, and a variety of recreational activities. From the scenic parks to the annual festivals, there’s always something happening in this welcoming city.

Discover the charm of Winchester and explore the possibilities of finding your dream home with the added convenience of basement parking. Your new life in this delightful Kentucky city awaits!

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!

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
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
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
1780 Stoner-Ephesus Rd, Winchester
$488,000
4 Beds ⋅ 3 Baths ⋅ 26019848 MLS
Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester
351 Boone Ave, Winchester
$379,000
4 Beds ⋅ 2 Baths ⋅ 26017258 MLS
Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home.

351 Boone Ave, Winchester
443 S Maple St, Winchester
$325,000
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
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