Winchester Homes with Walkout Basement

Winchester Homes with Walkout Basement

Welcome to Winchester, Kentucky – a charming city nestled in the heart of Clark County, where history and modern living blend seamlessly. Known for its picturesque landscapes and vibrant community spirit, Winchester offers a unique small-town charm with easy access to the amenities of larger cities. With a rich history dating back to the early 18th century, this welcoming city boasts a variety of local shops, parks, and dining options that cater to all tastes.

One of the standout features of homes in Winchester is the availability of properties with walkout basements. These homes provide an ideal solution for families looking for extra space, whether it be for recreation, storage, or even a separate living area. Imagine stepping out from your basement onto a beautifully landscaped backyard, perfect for entertaining or simply enjoying a peaceful evening under the stars. The walkout basement design not only enhances the functionality of the home but also allows for an abundance of natural light, creating a warm and inviting atmosphere.

Living in Winchester means enjoying a close-knit community, excellent schools, and a range of outdoor activities, from hiking to fishing in the nearby parks and lakes. With its affordable housing options and a variety of homes featuring walkout basements, Winchester is an ideal place for families, retirees, and anyone looking to embrace a serene lifestyle. Come explore the charm of Winchester, where your dream home awaits!

Newest Winchester Homes with Walkout Basement

$205,000
3 Beds ⋅ 3 Baths ⋅ 26019961 MLS
Welcome to **236 Buffalo Trace in Winchester, KY**—where thoughtful design meets comfortable, one-level living. This well-maintained **3-bedroom, 2.5-bath** home features a desirable **split-bedroom floor plan**, offering added privacy for the primary suite while keeping family or guest bedrooms conveniently located on the opposite side of the home. The spacious main level is designed for everyday comfort, with all bedrooms located on the first floor. Just off the kitchen, you'll appreciate the convenience of a dedicated laundry room, making daily routines a breeze. One of the home's standout features is the **spacious sunroom**, providing the perfect place to enjoy your morning coffee, unwind with a good book, or take in the peaceful views year-round. Step outside to a backyard framed by a **lush tree line**, creating a private, picturesque setting that's ideal for relaxing or entertaining. The **partially finished basement** offers valuable additional living space with endless possibilities—whether you're looking for a recreation room, home office, fitness area, or hobby space—while still providing room for storage. Conveniently located near shopping, dining, schools, and everything Winchester has to offer, this home combines a functional layout with the tranquility of a beautiful backyard setting. Don't miss your opportunity to make **236 Buffalo Trace** your next home!

236 Buffalo Trce, Winchester
$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
$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
$319,900
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, new kitchen appliances (7/17 delivery) and additional kitchen cabinets, additional insulation, and first floor bathroom plumbing updates.

128 Cherokee Dr, Winchester
$225,000
3 Beds ⋅ 4 Baths ⋅ 26017061 MLS
This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss!

128 Abbeywood Ct, 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
$499,000
5 Beds ⋅ 3 Baths ⋅ 26013305 MLS
First time on the market! This one-owner, all brick home offers 5 bedrooms, 2.5 baths, and sits on a spacious 0.6-acre lot. The well-designed floor plan provides plenty of room for family living and entertaining. The finished basement features a dedicated office and recreation room, offering flexible space for work, hobbies, or play. Enjoy the quality and durability of brick construction, a large yard, and the pride of ownership that shines throughout this well-maintained property. Don't miss this rare opportunity to make this exceptional home your own!

182 Chardonnay Ct, Winchester
$312,000
3 Beds ⋅ 3 Baths ⋅ 26008021 MLS
Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance.

200 Dubuy Dr, Winchester
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
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
Start Your Search