Winchester Homes with Interior Entry Basement

Winchester Homes with Interior Entry Basement

Welcome to Winchester, Kentucky, a charming city nestled in Clark County that beautifully blends small-town warmth with modern conveniences. Known for its rich history and vibrant community spirit, Winchester offers a unique lifestyle that attracts families, retirees, and young professionals alike. With its picturesque landscapes, friendly neighborhoods, and a variety of local amenities, it’s no wonder that Winchester is a sought-after destination for homebuyers.

One of the standout features of homes in Winchester is the presence of interior entry basements. These versatile spaces provide homeowners with endless possibilities, whether you envision a cozy family room, a home office, or a recreational area for entertaining guests. The convenience of accessing your basement from within the home adds an extra layer of comfort and functionality, making these properties ideal for those who value both style and practicality.

In addition to its beautiful homes, Winchester boasts a rich tapestry of local culture, with charming boutiques, delightful eateries, and community events that foster a sense of belonging. The city is also renowned for its scenic parks and outdoor activities, providing ample opportunities for recreation and relaxation.

As you explore the real estate market in Winchester, you’ll discover a variety of homes that feature the coveted interior entry basement, perfectly suited for your lifestyle needs. Experience the warmth of this inviting city and find your dream home in Winchester, where comfort meets community.

Newest Winchester Homes with Interior Entry Basement

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
5039 Combs Ferry Rd, Winchester
$2,299,000
5 Beds ⋅ 4 Baths ⋅ 26028074 MLS
Experience exceptional craftsmanship, privacy and resort-style living on over 12 acres in the highly desired Combs Ferry area of Clark County. Quietly tucked away yet conveniently located just 15 minutes from Hamburg in Lexington, as well as Winchester and Richmond, this extraordinary custom home was built in 2022 and offers 6,284 finished square feet, plus an additional 1,545 square feet of unfinished space ready for the next owner to customize. From the moment you enter, the quality and attention to detail are unmistakable. Andersen 400 Series windows and doors, decorative ceilings, custom trim and built-ins, engineered hardwood flooring, quartz countertops and designer lighting are featured throughout. The spacious kitchen is a true centerpiece, showcasing custom cabinetry, soft-close doors and drawers, under-cabinet lighting, a hidden walk-in pantry, double ovens, built-in microwave and a 5-burner gas range with built-in Thermador appliances. The main-level primary suite is a private retreat, complete with decorative beams, a stacked-stone gas fireplace, double vanities, soaking tub, expansive walk-in closet and an oversized tiled pass-through shower featuring dual shower heads and a centered rain head. Large walk-in closets accompany every bedroom, providing exceptional storage throughout. The finished lower level expands the possibilities with a home gym, dedicated movie theater with projector and equipment, home office/bonus room, wet bar with granite countertops, wine and beverage refrigerators and dishwasher, plus an additional bedroom with egress window, full bathroom, and walk-in closet. Multiple unfinished areas and the additional 1,545 square feet provide tremendous potential for future customization. Step outside and discover your own private entertainment destination. The 45,000-gallon oversized heated chlorine pool features a tanning ledge, deep-end swim ledge, fountain, LED lighting and energy-efficient variable-speed pump. Enjoy evenings around the custom outdoor fireplace, with the convenience of a dedicated outdoor bathroom. The property also includes a basketball court, shooting range, and detached garage with concrete floors and double garage bays. Additional thoughtful features include a formal dining room with custom moldings, laundry room with built-in cabinetry, mudroom/drop zone with built-ins and cubbies, spray foam insulation, three all-electric HVAC systems, and two 60-gallon water heaters. This is far more than a home; it is a custom-built private estate designed for everyday luxury, entertaining, recreation and relaxation, with room to make it uniquely your own. The combination of acreage, exceptional construction, extensive amenities and convenient location is truly rare. Schedule your private showing today and experience this breathtaking property firsthand. Seller is a licensed Realtor in Kentucky.

5039 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
42 Mockingbird Valley Rd, Winchester
$439,000
3 Beds ⋅ 3 Baths ⋅ 26000113 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
609 W Barlow Dr, Winchester
$375,000
4 Beds ⋅ 2 Baths ⋅ 26026446 MLS
Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, Winchester
54 Locust Dr, Winchester
$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
351 Boone Ave, 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
128 Cherokee Dr, Winchester
$299,900
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
229 S Highland St, Winchester
$160,000
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
3166 Colby Rd, 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
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