Refine Search
Map
Sort by
$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
$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
$374,900
3 Beds ⋅ 2 Baths ⋅ 26016576 MLS
Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a versatile dining room that can also serve as a home office. Don't miss the relaxing all-seasons room overlooking the professionally leveled and graded yard—perfect for morning coffee or evening gatherings. Upstairs, the private primary suite offers a generous bedroom, full bath, and three walk-in closets. An unfinished basement provides abundant storage or the opportunity to expand your living space. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in ready home offers comfort, charm, and exceptional convenience.

15 Moundale Ave, 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
$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
$289,000
3 Beds ⋅ 2 Baths ⋅ 26007779 MLS
Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000.

54 Locust Dr, Winchester
$2,999,000
6 Beds ⋅ 5 Baths ⋅ 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, 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
$2,750,000
8 Beds ⋅ 8 Baths ⋅ 26009631 MLS
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester
$724,950
2 Beds ⋅ 3 Baths ⋅ 25507944 MLS
Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of Heaven in the country this is your place. Only minutes from the Mountain Parkway, downtown Winchester, and Mount Sterling. Restaurants, shopping, golf courses, and several amenities are also just a short drive away.

455 Davis Ln, Winchester
$375,000
4 Beds ⋅ 3 Baths ⋅ 26008931 MLS
Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.

382 S Main St, Winchester
$359,000
3 Beds ⋅ 3 Baths ⋅ 26015128 MLS

608 Colby Rd, Winchester
$1,349,000
4 Beds ⋅ 5 Baths ⋅ 26013734 MLS
Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom. Head upstairs to the spacious 680sqft recreation room with its own full bathroom and attic storage access. Step outside to your large, spacious covered patio, personal inground pool with spa and sunken inground fire pit for endless entertaining. 3-Car garage offers ample storage. The 2670sqft Walk-out basement is a blank canvas with endless opportunities. Basement can be finished by builder at buyer's discretion. Some additional selections may be available. LUXURY, SPACE and PRIVACY just minutes from town.

1200 Craig Xing, Winchester