Courtesy: Coldwell Banker McMahan
859-744-1400
Do you ever wonder what it would be like to live in the days of Gone with the Wind? Well, here is your chance to own your own personal Tara. Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft room. Home is complimented by a beautiful front staircase as well as a back staircase for added convenience. Home has covered porches on both the front and rear of home to enjoy the beautiful sunrises and sunsets or just sit back and take in the country views from your own 5 acres. Home has a 3-car detached garage and storage shed. Schedule your private showing today.
Courtesy: Century 21 Advantage Realty - Georgetown
502-557-8600
The possibilities are endless with this exceptional rural property on 12+/- fully fenced acres. This beautifully updated 3-bedroom, 2.5-bath home features a renovated kitchen and baths, wide-plank cherry hardwood floors, heated travertine floors in two bathrooms, a spacious primary suite with sitting area and attached office or studio, dedicated laundry/mudroom with secondary pantry and a sunroom overlooking Trex decking. A detached garage offers approximately 900 sq ft of finished space along with a separate one-bedroom apartment complete with kitchen and bath—ideal for guests, extended family, or income potential. This land is designed for both relaxation and function with new fencing, automatic pasture waterers, fenced backyard, concrete driveway, and three truly unique barns including a fully renovated 9-stall barn, a well-preserved historic dairy barn with stalls, workshop space and paddocks, and an additional barn for shop and storage use. A climate-controlled party room with power and water adds even more flexibility for entertaining or events. This rare offering combines comfort, character, and unlimited potential!
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less than five minutes from I-64, less than ten minutes to WalMart, Kroger, Lowe's and a host of restaurants and specialty shops on the Winchester Bypass. Approximately twenty minutes from Hamburg area of Lexington. Call today to make an appointment to see this lovely home.
Courtesy: United Real Estate Bluegrass
859-800-7355
Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600 square feet, this 4-bedroom, 2-bath home provides plenty of room to spread out. The unfinished basement and one-car attached garage offer great storage, workshop potential, or future expansion. Inside, you'll find a welcoming foyer that opens to a bright, spacious living and dining area filled with natural light from large windows overlooking the countryside. The eat-in kitchen sits at the heart of the home, featuring stainless steel appliances, generous cabinet space, a walk-in pantry, and a cozy fireplace—perfect for gathering after a long day. Just beyond the kitchen is a large bonus room highlighted by charming brick details, ideal for entertaining, a family room, or even a home office or hobby space. The main level includes two roomy bedrooms, an updated full bath, and a convenient laundry room. Upstairs, the private primary bedroom offers a walk-in closet and ample storage, along with a recently updated second full bath and an additional bedroom—great for guests or family. Step outside and enjoy the simple pleasures of country life. Relax under the covered patio, listen to the birds, watch the sun rise and set, and take in the open views. With mature trees, open space, and plenty of privacy, this property is perfect for those who value peace, nature, and room to breathe. A rare opportunity to own a slice of Clark County countryside at a great value. Priced to sell and below appraisal—schedule your showing today!
Courtesy: Rector Hayden Realtors
859-276-4811
Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking distance to Shearer Elementary school and close to the interstate. The home is within walking distance to downtown for enjoying local restaurants, shops, and amazing festivals.
Courtesy: Bridgewater Real Estate
859-745-8632
This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics for AT&T and internet
Courtesy: Coldwell Banker McMahan
859-744-1400
PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of the highest points in Clark County, where you can see 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 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 39 years this remarkable property has been on the market. 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 farm offers not only beauty and serenity but also opportunity. It's truly a place to raise a family, connect with nature, and enjoy Kentucky living at its best.
Courtesy: Rector Hayden Realtors
859-276-4811
Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions apply. Additional parcel with 14.5 acres is also available. See also MLS#25017324 & 25017326.
Courtesy: Bluegrass Property Exchange
859-469-9429
Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights conveying. Wildlife is abundant, with wild turkey and deer frequently spotted across the land. A rare stone fence surrounds the property, adding to its timeless character. The land neighbors Old Providence Church—now known as Old Stone Church—Kentucky's 11th oldest standing building, dating back to 1793, where legendary frontiersman Daniel Boone was once a member. Whether you're seeking farmland, recreation, or an investment in Kentucky's past, this property offers a chance to own a genuine piece of Bluegrass history. Schedule a showing today and experience it for yourself! Buyer to satisfy themselves with survey and all property information. More Photos Coming Soon!
Courtesy: Rector Hayden Realtors
859-276-4811
Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect for all your outdoor activities! See also MLS#25017324 & 25017325.
Courtesy: Rector Hayden Realtors
859-276-4811
Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2 parcels available for sale separately. See MLS#25017325 and 25017326.
Courtesy: Dream Maker Realty, LLC
859-404-3384
Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half modern bathrooms *Located just minutes from the Winchester Bypass *Close to golf courses, shopping centers, and dining options Enjoy the perfect blend of comfort and convenience in one of Winchester's most desirable communities.
Courtesy: The Agency
859-285-0614
This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor bathroom, decorative ceilings, custom trim and built ins, finished basement, home gym, movie theatre, basement bar, Large walk-in closets attached to ALL bedrooms, basketball court, shooting range, detached garage with concrete floors and double garage bays. This list is endless. There is an additional 1545 sqft of unfinished space that new buyer can easily customize. Schedule your showing today and view this breathtaking property! Seller is a licensed Realtor in state of KY.
Courtesy: United Real Estate Bluegrass
859-800-7355
Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring hardwood floors, a spacious living area, dining area and kitchen with granite countertops, an island and plenty of room for a breakfast table. Off the kitchen you have a large walk-in pantry, separate utility closet and oversized laundry room. The primary suite on the main floor offers convenience and luxury with a walk-in shower, whirlpool tub, double vanities, and generous walk-in closet. Upstairs you'll find a bedroom with ensuite, and three additional bedrooms, all with hardwood floors, three feature cedar-lined walk-in closets—perfect for storage and organization. Outdoor living shines here. Spend summers relaxing by the private swimming pool, enjoy peaceful evenings on the large back deck, have a fire around the firepit and enjoy the sunsets on the covered front porch. For hobbyists, horse lovers, small farm enthusiasts, or anyone needing serious storage and workspace, this property truly delivers: a 40' x 60' metal building with 14' x 16' garage doors, plumbed for a future bathroom and hookup for your RV, a 61' x 20.5' run-in shed with two stalls, a 10' x 40' barn, an additional storage shed, multiple paddocks, ideal for goats, horses, or small farm animals. Whether you're looking for privacy, a hobby farm, a place for your animals, or a home with room to roam, this property checks every box. With space, function, and beauty inside and out, you do not want to wait to schedule your private showing. Opportunities like this don't come around often—come experience it for yourself!
Courtesy: Coldwell Banker McMahan
859-744-1400
Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just minutes from town.
Courtesy: Woods Realty Group
859-644-5077
Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to month so the tentant is aware they will need to vacate the property before close of sale.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-bedroom, 2-bath home offering an open-concept layout filled with natural light and soaring vaulted ceilings. The spacious living area flows seamlessly into the kitchen and dining spaces—perfect for both everyday living and entertaining. Enjoy peace of mind with a brand-new HVAC system, Gutter guards and relax outdoors on the newly built deck, complete with a convenient ramp for easy access. The fenced area is ideal for a small dog, and the property backs to a beautiful wooded area with a picturesque stone wall, adding privacy and charm. Located in a quiet, established neighborhood, this home combines comfort, convenience, and a touch of nature—all in one perfect package.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character on cozy days, and the kitchen feels straight out of an HGTV show with a new island and a layout designed for cooking, gathering, and entertaining. The bedrooms offer multiple closets, and the full bath includes a convenient laundry space. A formal living room at the front of the home provides extra flexibility for a home office or sitting area. Outside, a large multi-level deck wraps from the side of the home around to the back, creating the perfect setting for outdoor dining or quiet mornings with coffee. The 5 acre property has a large clearing behind the house, offering space for a pool, garden, or play area, while the rest of the land is wooded and gently sloped, offering privacy and a scenic backdrop. There are already two raised garden beds and a spot for a fire pit in the side yard, plus a detached garage, chicken coop, and storage shed. The HVAC system is brand new, and the roof is only two years old. This property has been well cared for and thoughtfully upgraded over the years. Come see why this farmhouse could be your perfect country retreat!
Courtesy: Freedom Realty & Property Management
859-771-0777
ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.
Courtesy: Steven D Adams Real Estate Services, LLC
859-744-1080
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.
Courtesy: Freedom Realty & Property Management
859-771-0777
Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden vegetables that will be ready for backyard entertaining. There is an oversized storage/tool shed, and a partially fenced back yard. The HVAC, water heater and Window World windows are less than 5 years old. Don't miss this one level home complete with an American Flag and Pole. Seller is offering buyers up to $5000 flooring credit at closing with an acceptable offer, pls include in any written offer.
Courtesy: Berkshire Hathaway de Movellan Properties
859-266-0451
Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional. Recent updates include an HVAC system less than 5 years old, offering peace of mind and energy efficiency. With tons of potential inside and out, this adorable home is move-in ready and waiting for your personal touch. A great opportunity for first-time homebuyers or investors looking for a solid, well-kept property in a convenient location. Don't miss out on this Winchester gem! Ask about a lease to Purchase.
Courtesy: Thwaites Realtors LLC
859-987-9119
**Open House Sunday 11/16 1-3PM** Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just waiting for its new owner!
Courtesy: Bridgewater Real Estate
859-745-8632
Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved 2 Momma's Cooking for You, the property features a fully equipped commercial-grade kitchen with a separate entrance through the garage and rear of the home—perfect for culinary entrepreneurs, serious home chefs, or anyone who loves to host. Inside, you'll find two spacious living areas, a dedicated dining room, and an eat-in kitchen that brings everyone together. All four bedrooms are located upstairs, including a remodeled primary suite with a walk-in closet and updated bathroom. Whether you're entertaining guests on the screened-in back porch or enjoying the large flat backyard with family and friends, this home invites you to create the kind of memories that matter. From holiday dinners to summer cookouts, from quiet mornings to bustling evenings, this is a place where life happens—and where you'll be proud to call home.
Courtesy: Keller Williams Legacy Group
859-544-6175
Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a renovated eat-in kitchen with a large island, leathered granite countertops, stainless steel appliances, and a gas range. A spacious walk-in pantry adds functionality, while updated windows, recessed lighting, and a new slider door (2025) bring in natural light. The primary suite is a true retreat with a private bath and an expansive walk-in closet. On the opposite wing, you'll find a second primary suite, creating the perfect setup for multi-generational living or hosting long-term guests. Outside, the property continues to impress with two driveways for ample parking, a large usable yard, and a huge detached garage ideal for parking, storage, or a workshop. An updated storage shed (2025) adds even more utility.
Winchester is located in Kentucky. Winchester, Kentucky 40391has a population of 18,993. Winchester 40391 is less family-centric than the surrounding county with 25.5% of the households containing married families with children. The county average for households married with children is 25.74%.
The median household income in Winchester, Kentucky 40391 is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester 40391 is 36.9 years.
The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.
