Winchester Homes with Unfinished Basement

Winchester Homes with Unfinished Basement

Welcome to Winchester, Kentucky – a charming city nestled in the heart of Clark County, where Southern hospitality meets small-town charm. Winchester boasts a rich history, with its roots dating back to the late 18th century, and today, it’s a vibrant community that offers a perfect blend of modern amenities and historical significance. Known for its picturesque landscapes and friendly atmosphere, Winchester is an ideal place for families, retirees, and anyone looking to enjoy a slower pace of life while still being close to urban conveniences.

One of the most appealing aspects of homes in Winchester is the availability of properties with unfinished basements. These versatile spaces offer endless possibilities for customization, allowing homeowners to create their dream areas, whether it’s a cozy family room, a home gym, or even an entertainment hub. The unfinished basement can serve as a blank canvas, ready to be transformed into whatever your heart desires.

The real estate market in Winchester features a variety of homes, from charming bungalows to spacious family residences, many of which come with the added benefit of an unfinished basement. This feature not only enhances the value of the property but also provides ample storage and potential for future expansion. Imagine the possibilities of crafting your ideal living space right below your feet!

With an inviting community, a rich cultural heritage, and homes that cater to your creative aspirations, Winchester is a delightful place to call home. Explore the opportunities that await you in this lovely Kentucky city, and discover the perfect property that speaks to your vision!

Newest Winchester Homes with Unfinished Basement

3 Beds ⋅ 2 Baths ⋅ 26023052 MLS

Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with custom cabinetry, granite countertops, and stainless appliances, and a versatile dining room that can easily serve as a home office. The former sunroom was converted to finished living space in 2021 and now provides an inviting all-seasons room along with a convenient laundry area overlooking the backyard. Upstairs, the private primary suite offers a generously sized bedroom, full bath, and an impressive three walk-in closets. An unfinished basement provides abundant storage and additional possibilities for future use. The extensive improvements throughout the property add tremendous value and peace of mind, including PEX plumbing lines, HVAC and water heater replaced in 2021, a whole-home generator installed in 2021, a new roof in 2025, new gutters, exterior doors, chimney cap, French drain, and fencing. Kitchen appliances, including the refrigerator, range, dishwasher, and microwave, were replaced in 2020, while the exterior brick has also been freshly painted as part of the home's updates. Outside, enjoy a professionally leveled and graded yard with plenty of room to relax or entertain. And with the whole-home generator, you'll have the added comfort of backup power when you need it most. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in-ready home offers the character of an established property with many of the major updates today's buyers are looking for. Schedule your private showing and see everything this exceptional Winchester home has to offer!

15 Moundale Ave, Winchester

3 Beds ⋅ 2 Baths ⋅ 26022771 MLS

Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look!

3 Nunnelly Ct, Winchester

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

3 Beds ⋅ 2 Baths ⋅ 26022208 MLS

Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

15 Kittison Dr, Winchester

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

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

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

3 Beds ⋅ 2 Baths ⋅ 26018346 MLS

Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner.

33 Bon-Haven Ave, Winchester

5 Beds ⋅ 4 Baths ⋅ 26012369 MLS

*****PRICED BELOW APPRAISAL & MOTIVATED SELLERS***** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester

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

******PRICED BELOW APPRAISAL & MOTIVATED SELLERS****** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester

Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester

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