Courtesy: Keller Williams Bluegrass Realty
859-260-1444
Step inside this beautifully remodeled historic home and you'll immediately understand why homes like this are so special. With loads of space, four bedrooms, and three full bathrooms, this home offers the character buyers love with the modern updates they need. Every detail has been thoughtfully refreshed while preserving the charm and warmth that make historic homes so hard to duplicate. From the spacious rooms to the inviting natural flow, this home feels both timeless and move-in ready. The heart of the home is the stunning gourmet kitchen -- beautifully updated and ready for everyday living, entertaining, and gathering with family and friends. Major updates have already been completed, including updated electric, plumbing, and HVAC, giving buyers added peace of mind. The first-floor bedroom and full bathroom create flexibility for guests, a home office, or multi-generational living. Upstairs, the spacious primary suite offers a private bathroom and walk-in closet, giving you the comfort and function today's buyers are looking for. Located near the heart of downtown Winchester, you'll love being close to local shops, dining, and the charm of a welcoming community. This is more than just a remodeled home -- it is a rare opportunity to own a piece of history without sacrificing modern comfort. Beautifully restored, thoughtfully updated, full of character, and ready for its next owner.
Courtesy: Keller Williams Commonwealth
859-721-2121
Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods.
Courtesy: Woods Realty Group
859-644-5077
Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. If you're looking for a place to call home this one is loaded with charm and busting with potential!! Schedule your showing today!!
Courtesy: WEICHERT REALTORS - ABG Properties
859-333-7271
Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.
Courtesy: The Agency
859-285-0614
Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality.
Courtesy: Stewart & Co Realty LLC
859-608-6200
A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ft og thoughtfully designed living space. Step inside to discover an open-concept layout perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. Generously sized bedrooms provide comfort and privacy, while the flexible floor plan offers space to fit your lifestyle. Located in a growing Winchester community, you'll enjoy the small-town living with convenient access to shopping, dining, schools, and major roadways. Don't miss your opportunity to own this beautiful home. Schedule your showing today!
Courtesy: Joyce Marcum Realty
859-624-0088
Don't miss out on this beautiful two-story, 3 BR, 1.5 BA home in a great neighborhood in the heart of Winchester! Great-sized living room with real hardwood floors, complete with a tiled fireplace with mantel (seller has never used). Spacious Kitchen with a tiled backsplash, white cabinets, and stainless-steel appliances! Large Dining Room that will accommodate nearly any size table. Half bath with laundry on the first floor. Upstairs, the primary bedroom is very spacious, with large closets. The other two bedrooms are very spacious as well, with fresh paint and hardwood floors! Large full bathroom comes complete with a clawfoot tub. Outside features include a wrap-around front porch (with newly installed decking). Large deck on the back, perfect for entertaining. A fenced-in backyard makes for an ideal play area for children or those fur babies! Comes complete with a storage building. If you're looking for something outside the typical cookie-cutter homes, this one is it! This home has so much character and charm! Must see to truly appreciate! This is priced to sell, so it won't last long. Call me today to set up a time to check this one out!
Courtesy: Coldwell Banker McMahan
859-744-1400
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!
Courtesy: WTC Realty LLC
606-344-6560
Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.
Courtesy: Red River Gorge Real Estate
859-314-2465
MIDNIGHT ON THREE - Luxury Living Meets Convenience in Clark County KY Nestled on 3.054 beautifully maintained acres, this stunning home was thoughtfully designed with quality and elegance in every detail. Just 2 minutes from Exit 10 on the Mountain Parkway, this extraordinary custom-built estate offers a rare combination of privacy, craftsmanship, and accessibility. From the moment you arrive, the striking exterior, expansive covered porches, and picturesque setting create an unforgettable first impression. Inside, soaring ceilings, walls of windows, and abundant natural light showcase the home's exceptional design and create a warm, inviting atmosphere. The open-concept living space is anchored by a floor-to-ceiling stone fireplace and flows seamlessly into a designer kitchen featuring custom cabinetry, premium countertops, upscale fixtures, and a large gathering island perfect for entertaining. The luxurious primary suite offers a private retreat with a spa-inspired bath, oversized walk-in shower, soaking tub, and custom finishes throughout. Every room reflects the superior craftsmanship and attention to detail that set this home apart from ordinary construction. Whether you're enjoying morning coffee on the screened porch, hosting guests in the expansive living areas, or simply taking in the peaceful surroundings, this property delivers a lifestyle of comfort and sophistication. The versatile upper-level loft provides additional living space ideal for a media room, office, or guest retreat. Situated close to one of Eastern Kentucky's most desirable areas, this property offers quick access to Lexington, Winchester, and the Red River Gorge region while maintaining the privacy and serenity of a luxury country estate. Exquisite custom construction. Premium finishes. Exceptional location. For buyers seeking a truly remarkable home where quality, style, and convenience come together, this Clark County masterpiece is a rare opportunity. Luxury, privacy, and craftsmanship—without compromise.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship — rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried mornings. The newly remodeled kitchen features all-new appliances and is ready for full-time living or weekend retreats. Outside, enjoy an in-ground pool with concrete decking, a stocked pond, a seasonal stream along the boundary, RV pad with full electric and water hookup, a 4-stall metal barn, 2-bay garage under the home, and a 3-bay detached garage. 14.38 private acres with room to breathe, grow, and put down roots. Located just ~15 minutes from Downtown Winchester, ~25 minutes from Lexington, and under 30 minutes from Red River Gorge. Fox General Store is located less than a mile away. Private showings by appointment only.
Courtesy: The Agency
859-285-0614
Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The completely renovated kitchen boasts new cabinetry, gorgeous granite countertops, and new stainless appliances, making it perfect for cooking, entertaining, and everyday living. Enjoy mornings on the covered front porch and evenings in the fenced backyard with a deck, ideal for relaxing or hosting friends and family. If you are looking for low maintenance property, one level living and a home ready to move straight into, look no further! Stylish updates, great outdoor spaces, and a classic all-brick construction, situated on a large corner lot......Don't miss this one!
Courtesy: Coldwell Banker McMahan
859-744-1400
Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home!
Courtesy: Ensor Real Estate, LLC
859-749-0892
Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open Living Room, Dining Room and Kitchen Area, Spacious Laundry Room, Covered back patio for outdoor living! Beautiful Hardwood floors, updated bathroom and kitchen, exceptional location, building out back for he shed or she shed or storage, move in and enjoy the sunset!
Courtesy: Waizenhofer Real Estate
502-777-0751
Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with a built-in bench for convenient storage. The open concept offers both comfort and style. Between the kitchen's open design with granite countertops to the primary suite that offers relaxation at its finest. You may have a hard time deciding on which area of the home you wish to be in. Enjoy your outdoor space that offers a privacy fence and a 10'x16' building for your mower and additional storage. This home invites you to experience the best of Kentucky living and is just waiting on you to call it home! Located only 4 Minutes to Walmart!
Courtesy: Kentucky Residential Real Estate, LLC
859-229-5974
Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance. FHA loans will require extended closing time due to ownership rules.
Courtesy: Green Team Real Estate Service
502-439-7596
Opportunity knocks for the buyer with vision! This spacious 4-bedroom, 2.5-bath home is mid renovation and is well on its way to becoming something truly special. With a first-floor primary suite, walk-in closets, partial basement with sump pump already installed, many major systems already in place, and a storage shed in the backyard, many of the big-ticket features are done for you. The home is currently unfinished, with flooring, wall finishes, the kitchen, and the bathrooms still needing completion, gives you the rare chance to customize the final touches to your own style and preferences. The heavy lifting has already begun - now it's your opportunity to bring the project across the finish line and create instant equity in the process. Whether you're an investor, contractor, or ambitious homeowner looking for a rewarding project, this property offers tremendous potential and a head start on your dream home. Bring your imagination and see the possibilities!
Courtesy: Keller Williams Legacy Group
859-544-6175
Beautifully updated and move-in ready, this 3-bedroom, 2-bath home offers comfort, style, and versatility throughout. Inside, you'll find a spacious living room, an updated kitchen with ample cabinetry, tile showers, original hardwood, modern LVP, and thoughtful finishes throughout. A large utility room offers flexible space for a home office, playroom, or extra storage. The unfinished basement, two-car detached garage, fully fenced backyard, patio, and covered front porch add even more function and charm. Recent updates include HVAC/furnace, roof shingles, windows, vinyl siding, flooring, kitchen cabinetry, bathroom vanities, light fixtures, doors, and hardware. With so much already done, all that's left to do is move in and enjoy.
Courtesy: Bluegrass Home Group
859-687-1010
Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.
Courtesy: HomeLand Real Estate Inc - Mt Sterling
606-356-3063
Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing for peace of mind and dishwasher allowance!
Courtesy: RE/MAX Creative Realty
859-422-2000
Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.
Courtesy: Freedom Realty & Property Management
859-771-0777
Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic surroundings, and the tranquility of rural living minutes from city amenities. Designed for ease and functionality, the home features convenient one-level living with the added bonus of a finished basement--perfect for extra living space, entertaining, or hobbies. An inviting all-season room provides the ideal spot to relax year-round and a covered front porch overlooking a neighboring pond offers a tranquil place to enjoy your morning coffee or wind down at the end of the day. The kitchen features brand new stainless appliances, with transferrable warranties to the new owner. Did I mention the new roofs and Geothermal HVAC for efficient inside temperature control? Don't miss the first level primary bedroom with a private bathroom and walk in closet. Outside, the property really shines with a detached 3-car garage and a large barn with three stalls, a tack room and two multipurpose rooms. Also there is an additional metal barn with a tool room and three multipurpose rooms. All of these outbuildings have electricity and the wooden barn also has water with a separate fenced area for animals. Whether you're looking for a quiet retreat, a working or hobby farm, or a place to create lasting memories, this property delivers a warm and welcoming atmosphere you'll love coming home to.
Courtesy: Keller Williams Bluegrass Realty
859-260-1444
Here is your opportunity to purchase a new construction home built in an established neighborhood. Approaching the home you notice the large covered front porch with plenty of room for seating. When you walk in the home, you have white oak LVP flooring running throughout the living room, kitchen and dining area that are all open to one another. The kitchen has white Shaker style cabinets, granite countertops and stainless steel appliances. The dining area has a mahogany wood french door that leads to the rear wooden deck. In the backyard there is a large storage building and a wooden privacy fence down one side of the yard. Off of the kitchen is a laundry room with washer and dryer hookups and the gas tankless water heater is located here. In the hallway is the second full bathroom and two bedrooms across the front of the house. The primary bedroom with walk-in closet and primary bathroom are located along the rear of the house. All of the bedrooms have carpeted floors and ceiling fans installed. Call today and schedule your showing of this new home.
Courtesy: Stewart & Co Realty LLC
859-608-6200
You don't want to miss this desirable two primary bedroom home with 2 full bathrooms and large walk-in closets!! There is a gorgeous gas fireplace situated as the focal point of the main living space and an attached one car garage.
Courtesy: Keller Williams Legacy Group
859-544-6175
Welcome to 133 Bay Hill Drive in Winchester, Kentucky — a spacious and beautifully maintained home offering over 3,200 square feet of living space in one of the area's desirable subdivisions. Conveniently located just minutes from town and close to local factories and major employers, this property offers the perfect blend of comfort, convenience, and neighborhood living. Inside, you'll find plenty of room for the whole family with generous living spaces, spacious bedrooms, and a layout designed for both everyday living and entertaining. Whether you're hosting guests or simply enjoying a quiet evening at home, this property gives you the space to do it all comfortably. Step outside and enjoy the covered back porch — the perfect place to relax with your morning coffee or unwind after a long day. The backyard also includes a storage shed, providing extra space for tools, lawn equipment, or additional storage needs. Located in a well-kept subdivision with an HOA, this home offers the benefits of community living while still providing the space and privacy buyers are looking for. 133 Bay Hill Drive Winchester, KY Over 3,200 Sq Ft Spacious Layout Covered Back Porch Storage Shed Included Minutes from Town & Local Factories Located in a Beautiful HOA Community If you've been searching for a spacious home in a great location with room to grow, this one deserves a look. Schedule your private showing today!
Winchester is located in Kentucky. Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% 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 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 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.
