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

$285,000
3 Beds ⋅ 2 Baths ⋅ 26019908 MLS
Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

108 Milwood Dr, Winchester
$498,000
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
$899,000
3 Beds ⋅ 2 Baths ⋅ 26019577 MLS
Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship -- rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried mornings. The newly remodeled kitchen features all-new appliances and is ready for full-time living or weekend retreats. Outside, enjoy an in-ground pool with concrete decking, a stocked pond, a seasonal stream along the boundary, RV pad with full electric and water hookup, a 4-stall metal barn, 2-bay garage under the home, and a 3-bay detached garage. 14.38 private acres with room to breathe, grow, and put down roots. Located just ~15 minutes from Downtown Winchester, ~25 minutes from Lexington, and under 30 minutes from Red River Gorge. Fox General Store is located less than a mile away. Private showings by appointment only.

200 Old Log Lick Rd, Winchester
$410,000
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
$245,000
3 Beds ⋅ 2 Baths ⋅ 26018026 MLS
Meticulously maintained 3-bedroom, 2-bath home on a full basement with wonderful curb appeal! Beautiful landscaping and a welcoming covered front porch invite you into this charming home. Inside, you'll find a warm and inviting main level featuring handsome hardwood flooring, a cozy fireplace, and a spacious living area. The adorable kitchen offers plenty of cabinet and counter space, making meal prep and entertaining a breeze. Down the hall are three comfortable bedrooms and a full bath. The finished basement provides an expansive second living area with a propane fireplace and a second full bath. This versatile space could easily serve as a fourth bedroom, home office, recreation room, or guest suite. You'll also appreciate the oversized one-car garage with driveway access, offering abundant room for parking, storage, or workshop space. Outside, enjoy the privacy of the fenced backyard complete with a garden area and a large storage building. The location is price with close proximity to both Winchester and Lexington! Please note: The HVAC system is currently not functioning, and the property is being sold "as is" but all inspections are welcomed. Seller requests a minimum of 24-hour response time on all offers.

216 Robyn Dr, Winchester
$269,900
3 Beds ⋅ 1 Baths ⋅ 26016881 MLS
SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!!

2379 Big Stoner Rd, 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
$329,000
3 Beds ⋅ 3 Baths ⋅ 26016008 MLS
Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and complemented by a covered pool bar with electricity. An additional freestanding deck provides even more room to relax, while the fixed outdoor movie screen creates unforgettable movie nights from the comfort of your pool float. Gather around the fire pit on cool evenings, shoot hoops on the spacious patio, relax in the hot tub, or enjoy hobbies and extra storage in the outbuilding complete with electricity. The fully fenced backyard truly feels like your own private staycation. Inside, the home offers a comfortable and flexible layout. The fully equipped eat-in kitchen features a breakfast bar with a cozy dining/sitting area with fireplace insert that's perfect for easy cooking and entertaining. The main level includes a private primary suite, an additional bedroom, and a second full bath. The finished walkout basement adds exceptional flexibility with a spacious family room that could easily serve as a third bedroom, a full bath, and a bonus room ideal for a home office, exercise room, hobby space, or even a potential fourth bedroom (no egress). A one-car basement garage provides additional storage and convenience. From the street, this home is modest and unassuming—but step into the backyard and you'll discover one of Winchester's best-kept secrets. If you've been dreaming of a home where every day feels like a vacation with an affordable price tag, this is one you won't want to miss!

13 Bel Air Dr, Winchester
$499,900
4 Beds ⋅ 3 Baths ⋅ 26010312 MLS
One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

16 Manor Dr, Winchester
$268,900
4 Beds ⋅ 3 Baths ⋅ 26011798 MLS
Spacious and well - maintained 4 bedroom home featuring 2 full bathrooms, one half bath which is ready to be upgraded with the addition of a shower to function as an additional full bathroom. This home offers a comfortable layout with replacement windows, a cozy wood burning fireplace and updated stainless steel appliances incuding the range, refrigerator, dishwasher and microwave. Enjoy outdoor living on the rear covered deck overlooking the well - tended backyard. A drain system efficiently carries water to the end of the property for added peace of mind. With thoughtful updates and solid upkeep throughout, this property is move-in ready and is full of charm

311 Geronimo Ct, Winchester
$189,900
2 Beds ⋅ 1 Baths ⋅ 25506124 MLS
Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

605 College St, 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
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