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 Southern hospitality meets small-town charm. Known for its rich history and vibrant community, Winchester is an ideal place for families, retirees, and everyone in between. With its picturesque landscapes and a welcoming atmosphere, it’s no wonder that this city has become a sought-after destination for homebuyers.

One of the standout features of homes in Winchester is the availability of properties with walkout basements. These unique spaces offer an abundance of possibilities, whether you envision a cozy family room, a home office, or a personal gym. Imagine stepping out into your backyard from the comfort of your basement – a perfect setting for entertaining guests, gardening, or simply enjoying the serene beauty of your surroundings.

Winchester boasts a variety of neighborhoods, each with its own distinct character and charm. From historic homes that reflect the city’s storied past to modern constructions that cater to contemporary lifestyles, there’s something for everyone. The close-knit community is complemented by an array of local amenities, including parks, shops, and dining options, ensuring that residents have everything they need right at their fingertips.

Whether you’re drawn to the stunning natural beauty of the area or the friendly vibe of the community, Winchester is a fantastic place to call home. Explore the homes with walkout basements and discover how this feature can enhance your living experience, offering both functionality and a seamless connection to the great outdoors. Your dream home awaits in Winchester!

Newest Winchester Homes with Walkout Basement

208 Buffalo Trce, Winchester
$149,000
2 Beds ⋅ 3 Baths ⋅ 26029736 MLS
Multiple offers have been received on this property. Please submit your offer before the deadline shown below, or If your buyer would like to make any revisions to their submitted offer, follow the steps below: Navigate to VRM Properties (web address in private remarks) Sign In with Username & Password Click the Menu Icon (the 3 orange bars in the upper right side of the screen) Click "My Offers" and Submit your revisions by clicking on the Next Action: Submit Highest & Best link For detailed instructions, please see the attached Multiple Offers Job Aid attached to this listing. The Highest & Best deadline for revisions is 1:00PM Central Time on 10-30-2026. If no revisions are submitted by the deadline, the existing offer will be considered your final Highest & Best offer. Ranch style home on full, finished, walk out basement. Home features entry foyer, primary bedroom with adjoining bath, second full bath off the foyer, Great room style kitchen and living room area and a formal dining area/den. Lower level is finished with half bath, one bonus room with closet and second bedroom with windows but no closet. as well as a family room area. Additional bonus is the unfinished storage/storm shelter area. Home has off street parking, backyard deck and is ready for a new owner. This property has discoloration. Will be REHAB type loan

208 Buffalo Trce, Winchester
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
323 Skylark Dr, Winchester
$424,500
5 Beds ⋅ 4 Baths ⋅ 26028682 MLS
You have to see this one! Spacious 5-bedroom, 4-bath home priced under recent appraisal! The primary bedroom and two other bedrooms are on the main level. This wonderful home sits on a large lot with a great backyard perfect for entertaining, play and relaxation. Conveniently located close to the Winchester bypass and shopping, you'll enjoy easy commutes and everyday errands. The basement offers flexible space for so much more- think game room, home office, gym, or all three. Plus, a separate garage keeps the lawnmower and yard equipment neatly out of the way. With generous living space throughout, this home truly offers room for everyone. Don't miss this fantastic value in a prime location- schedule your showing today.

323 Skylark Dr, Winchester
200 Evergreen Dr, Winchester
$457,900
4 Beds ⋅ 3 Baths ⋅ 26028668 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** The Paddock offers approximately 1,986 square feet of thoughtfully designed main-level living with 3 bedrooms, 2.5 baths and a versatile flex room suitable for a home office or optional fourth bedroom. The open kitchen, dining and great-room layout features 10-foot ceilings, bar seating and an expanded walk-in pantry. A private primary suite includes a spacious walk-in closet and well-appointed bath, while two additional bedrooms and a second full bath provide comfortable accommodations for family or guests. Covered front and rear outdoor spaces and an attached 2-car garage complete the main level. The home is planned over an unfinished walkout basement, providing excellent storage and future finishing potential, with plumbing stubbed for a future basement bath. Floor plan, square footage, finishes and construction details are subject to final plans, specifications and selections. Images are conceptual renderings.

200 Evergreen Dr, Winchester
220 Evergreen Dr, Winchester
$513,600
3 Beds ⋅ 2 Baths ⋅ 26028669 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** The perfect combination of style, comfort, and quality craftsmanship in the Run for the Roses floor plan. This thoughtfully designed ranch home offers an open-concept layout with spacious living areas, a split-bedroom floor plan, and upgraded finishes throughout. The heart of the home features an expansive great room that flows seamlessly into the dining area and beautifully designed kitchen, complete with a large center island, abundant cabinetry, and a walk-in pantry creating the ideal space for everyday living and entertaining alike. The private primary suite is designed as a true retreat, offering a spacious bedroom, luxurious ensuite bath with dual vanities, soaking tub, separate shower, private water closet, and an oversized walk-in closet with direct access to the laundry room for added convenience. On the opposite side of the home, two generously sized guest bedrooms share a full bath, providing privacy and flexibility for family, guests, or a dedicated home office. Need more space? This home is built on a full unfinished walkout basement, offering incredible potential to nearly double your living area. Whether you envision additional bedrooms, a family room, home theater, fitness space, workshop, or simply exceptional storage, the lower level is ready to be customized to fit your lifestyle. Outside, enjoy a welcoming covered front porch and an attached two-car garage, while the proposed construction gives you the opportunity to personalize many of the home's finishes and selections to make it uniquely yours. If you've been searching for the perfect blend of modern design, functional living space, and room to grow, the Run for the Roses is a home you won't want to miss. 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.

220 Evergreen Dr, Winchester
225 Evergreen Dr, Winchester
$469,925
3 Beds ⋅ 2 Baths ⋅ 26028670 MLS
***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** Discover the perfect blend of timeless design, modern comfort, and future expansion potential in The Mulberry, a thoughtfully designed ranch home offering well-appointed main-level living plus a full unfinished walkout basement ready for your personal vision. The open-concept floor plan is designed for both everyday living and entertaining, featuring a spacious Great Room with a gas fireplace, a bright dining area, and a beautifully designed kitchen complete with a large center island, walk-in pantry, abundant cabinetry, and dedicated oven/microwave wall cabinet. The adjoining rear covered porch extends your living space outdoors, creating the perfect setting for relaxing or entertaining while overlooking your backyard. The private primary suite serves as a peaceful retreat with a generous walk-in closet, dual vanity, oversized walk-in shower, soaking tub, and convenient access to the laundry room through the owner's hall. On the opposite side of the home, two additional bedrooms, a full bath, and a dedicated office provide comfortable accommodations for family, guests, or working from home.

225 Evergreen Dr, 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
25 W Hickman St, Winchester
$325,000
5 Beds ⋅ 3 Baths ⋅ 26028567 MLS
Distinctive character, generous space, and a convenient location near downtown Winchester! This five-bedroom, three-bath brick home offers room to spread out, with flexibility for guest rooms, a home office, or hobbies. Eye-catching architectural details and an inviting front porch give the home memorable curb appeal. With downtown shops and dining nearby, 25 W. Hickman Street combines the appeal of an established neighborhood with everyday convenience. Schedule your private showing and picture your next chapter here! Property can be used as residential or office space.

25 W Hickman St, Winchester
106 Quail Ridge Rd, Winchester
$221,000
3 Beds ⋅ 2 Baths ⋅ 26028482 MLS
Motivated Seller, just lowered the price, seller if offering $2000 for concessions, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

106 Quail Ridge Rd, Winchester
5825 Combs Ferry Rd, Winchester
$4,895,000
3 Beds ⋅ 4 Baths ⋅ 26028325 MLS
A Rare 77 ± acre Kentucky Estate with a new custom home & equestrian facilities offers privacy, commanding views, and the natural beauty of Kentucky's renowned horse country that truly define this exceptional recreational estate. Offering an extraordinary combination of luxury living, equestrian amenities and recreational opportunities, the property has been thoughtfully designed to provide both functionality and tranquility. The setting is simply spectacular, with Nursery Place Thoroughbreds and Harkness Edwards Winery as immediate neighbors, placing this estate in an impressive equestrian environment just minutes from Fayette County. A winding private drive passes the beautiful stocked ponds, leading to the highest point of the estate where an impressive custom stone residence and equestrian facility command panoramic views. The recently completed 5,800 ± square-foot custom 3 BR/3.5 BA stone manor home combines elegant finishes with a warm aesthetic. Features include rustic boxcar-wood flooring, a custom kitchen with granite center island and countertops, Wolf and Sub-Zero appliances and custom cabinetry. The spectacular great room provides generous space for both living and dining, highlighted by a floor-to-ceiling stone fireplace and an expansive wall of windows framing remarkable views of the surrounding countryside. Both the great room and first-floor primary suite open onto a massive covered deck featuring an outdoor fireplace and hot tub—an exceptional setting for entertaining or simply enjoying the serenity of the property. The private main floor primary suite includes its own fireplace, luxurious en suite bath, large walk-in closet, convenient laundry area, and private office. A beautiful stone entrance foyer leads to a loft overlooking the great room. The walkout lower level features 2 additional spacious bedrooms and an open family room, with direct access -through the walkout doors- to the impressive in-ground swimming pool. Adding another dimension to the estate is the remarkable barndominium which includes approx 1,000 sf of living quarters featuring 1 bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility- capable of accommodating aircraft, collector cars, RVs, and/ or other recreational vehicles. Impressive hydraulic doors and extra-tall ceilings provide easy access. Inside, rustic barnwood finishes create a warm and inviting atmosphere ideal for entertaining, gatherings, or displaying a collection. A substantial wood shop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with 4 horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the 10-acre fenced field for horse turnout. Whether envisioned as a private equestrian estate, recreational compound, luxury country residence or a combination of all three, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings- it truly must be seen to be appreciated.

5825 Combs Ferry Rd, 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
9930 Mount Sterling Rd, Winchester
$639,000
3 Beds ⋅ 1 Baths ⋅ 26027905 MLS
Possibilities Galore! This beautiful 3 bedroom brick home comes with 18 acres of land, a tobacco barn, and a 4700 square foot building. It is a prime location on the Clark and Montgomery County line. The huge building could be used for lots of things. It has electric and water. Come grab on to this great opportunity while it last.

9930 Mount Sterling Rd, Winchester
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