Winchester Homes with Interior Entry Basement

Winchester Homes with Interior Entry Basement

Welcome to Winchester, a charming city located in Clark County, Kentucky. Known for its rich history and friendly community, Winchester offers a peaceful and welcoming atmosphere for residents and visitors alike.

One of the unique features of homes in Winchester is the interior entry basement. This design not only adds character to the properties but also provides additional space for storage or living areas. Whether you're looking for a cozy bungalow or a spacious family home, Winchester has a variety of options to suit your needs.

In Winchester, you'll find a mix of historic architecture and modern amenities, creating a perfect blend of old-world charm and contemporary living. The city boasts tree-lined streets, vibrant parks, and a thriving downtown area with boutique shops and local eateries.

With easy access to outdoor recreational activities, including hiking, fishing, and camping, Winchester is a haven for nature enthusiasts. The city also has top-rated schools, making it an ideal place for families to settle down and thrive.

Whether you're searching for a new place to call home or simply exploring the beauty of Kentucky, Winchester has something for everyone. Come and discover the magic of this picturesque city with homes featuring interior entry basements that add a touch of uniqueness to the real estate landscape.

Newest Winchester Homes with Interior Entry Basement

$244,000
3 Beds ⋅ 2 Baths ⋅ 26023633 MLS
SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home retains much of its original character and offers an opportunity for a buyer to update the kitchen, baths and finishes to their own style. This property is being offered as a short sale, meaning the seller's lender must review and approve the purchase price and terms. Please allow approximately 30-45 days for lender review and approval of any offer. Property is being sold AS-IS; inspections are welcome.

54 Locust Dr, Winchester
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 26020418 MLS
This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are minutes to Hamburg Lexington as well as Winchester and Richmond. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor bathroom, decorative ceilings, custom trim and built ins, finished basement, home gym, movie theatre, basement bar, Large walk-in closets attached to ALL bedrooms, basketball court, shooting range, detached garage with concrete floors and double garage bays. This list is endless. There is an additional 1545 sqft of unfinished space that new buyer can easily customize. Schedule your showing today and view this breathtaking property! Seller is a licensed Realtor in state of KY.

5039 Combs Ferry Rd, 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
$309,900
5 Beds ⋅ 2 Baths ⋅ 26017629 MLS
Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level offers a second spacious living area—perfect for a family room, game room, home office, or guest retreat. An exterior entrance to the basement adds flexibility and convenience. Situated in an established neighborhood just minutes from shopping, dining, schools, and other everyday amenities, this home combines a desirable location with a functional layout that's ready to fit your lifestyle. Don't miss your opportunity to make this Winchester home your own! Updates include new furnace, brand new kitchen appliances and additional kitchen cabinets, additional insulation, and first floor bathroom plumbing updates.

128 Cherokee Dr, 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
$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
$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
$239,900
3 Beds ⋅ 2 Baths ⋅ 26013350 MLS
"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!

377 Crescent Ave, Winchester
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