Courtesy: Keller Williams Commonwealth
859-721-2121
Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or entertaining. Just off the main level, the three-seasons room offers the perfect spot for hosting guests, relaxing, or enjoying views of the backyard year-round. All three bedrooms and two full baths are conveniently located on the main level, including one bath that has been recently updated. Downstairs offers additional living space along with a laundry area, providing flexibility for a second den, office, or hobby space. Outside, you'll find a side-entry two-car attached garage and a beautifully landscaped backyard with a charming setting perfect for relaxing or entertaining.
Courtesy: RE/MAX Elite Lexington
859-245-1165
Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with all stainless appliances including a gas range for cooking those delicious meals. The large kitchen overlooking the great room offers the convenience of an eat in bar area, delightful dining space, an oversized hidden pantry and a unique kitchen niche to make it your own unique space. This home is all about convenience and privacy with the split bedroom concept. Lots of space in the primary bedroom for your king size bed plus a nice sitting area. You will love the huge primary bath with stylish custom tile and the adjoining generous sized closet for the fashionista. In edition there are two guest bedrooms with a full bathroom. There is a flex room that makes a great office space or possibly a playroom for children. The large laundry area and drop zone is an added convenient feature to the home. From enjoying your morning coffee, evening relaxation or outdoor gatherings the large covered back patio is the place to be with the outdoor fireplace. This home has so much to offer! Get your tour scheduled today.
Courtesy: Berkshire Hathaway HomeServices Foster Realtors
859-623-9427
There's nothing sweeter than countryside views! 30 Minutes to Hamburg in Lexington & USDA eligible at 0% down! Located off the Mountain Parkway & Ironworks Rd, this property features over an acre of land, a fenced-in backyard, and a new septic tank system. Well maintained and only 2 years old, this home is the perfect opportunity to start your mini farm. (3rd bedroom not photographed, being used as storage)
Courtesy: Freedom Realty & Property Management
859-771-0777
Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes stainless steel appliances, while the main living areas showcase durable laminate plank flooring with carpeted bedrooms for added comfort. Enjoy both a covered front porch and covered rear patio, perfect for relaxing and taking in the surrounding views. A 2-car garage adds additional storage and practicality. Conveniently located just minutes from downtown Winchester, shopping, restaurants, and with easy access to Hamburg in Lexington, this home offers the ideal balance of small-town living with nearby amenities.
Courtesy: Keller Williams Legacy Group
859-544-6175
Welcome to 407 Pueblo Court! This well-kept 3 bed, 2 bath home sits on a quiet cul-de-sac and offers easy one-level living in a convenient Winchester location. Inside, you'll find a functional layout, great natural light, and comfortable living spaces that feel like home. The spacious backyard gives you plenty of room to relax, entertain, or enjoy time with family and friends. Whether you're a first-time buyer, downsizing, or looking for a solid investment opportunity, this home checks a lot of boxes.
Courtesy: Keller Williams Bluegrass Realty
859-260-1444
Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 3,400 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm. Large, inviting rooms and graceful details create a sense of comfort and character that newer homes simply can't replicate. At the heart of the home is a beautiful gourmet kitchen, perfect for slow mornings, lively gatherings, and everything in between. The home also features a convenient first-floor bedroom and full bath, ideal for guests or flexible living. Upstairs, you'll find a full primary suite offering a spacious walk-in closet and private bathroom, creating a comfortable and functional space designed for everyday living. With four bedrooms and three full bathrooms, the home offers generous living areas that beautifully balance historic charm with modern elegance. Located near the heart of Winchester's charming downtown, you'll enjoy the ease of nearby shops, dining, and the welcoming community that makes this area so special. Homes like this don't come along often--rich in character, beautifully restored, and ready for its next chapter.
Courtesy: RE/MAX Creative Realty
859-422-2000
Welcome to this beautiful new home in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.
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!
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: Block + Lot Real Estate
859-309-0099
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.
Courtesy: Marshall Lane Real Estate - Lexington
502-682-1226
Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).
Courtesy: RE/MAX Creative Realty
502-570-5800
Adorable & inviting from the moment you arrive! This charming 2-bedroom, 1-bath home welcomes you with a cozy front porch perfect for relaxing evenings. Step inside to a comfortable living room, along with the kitchen with a dedicated dining space—ideal for everyday living or entertaining. Out back, you'll find a spacious yard ready to enjoy, complete with a fire pit for those crisp fall nights and room to make it your own. Off-street parking is a breeze out front and private parking out back, plus a 1.5-car garage for added convenience. Whether you're just starting out or looking to simplify, this home is full of charm and opportunity. Don't miss your chance—schedule your showing today!
Courtesy: Rector Hayden Realtors
859-276-4811
Welcome home to easy, one-level living in this inviting 3-bedroom, 2-bath ranch! From the moment you step inside, the foyer opens to a spacious living room with a vaulted ceiling, creating a bright and open feel. The desirable split-bedroom layout offers privacy, with the primary suite tucked away on one side of the home featuring a large walk-in closet and full bath. Two additional bedrooms and a second full bath are located on the opposite side, making the floor plan both functional and comfortable. The spacious eat-in kitchen provides plenty of room for gathering and opens to a screened-in patio, the perfect spot for morning coffee, relaxing evenings, or enjoying the backyard view. Outside, the large backyard offers room to garden, play, or entertain, plus a unique two-level storage shed for extra space and organization. Conveniently located near restaurants, shopping, and everyday amenities. Home being sold AS-IS. Inspections welcome.
Courtesy: Threshold Real Estate Services
859-223-2277
Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that practically begs for cozy evenings and lively gatherings alike. The kitchen shines with quartz countertops, stainless steel appliances, and classic shaker cabinetry, while a large pantry keeps everything organized and within reach. Elegant wood plantation blinds frame the views throughout, adding warmth and character to every room. Three bedrooms and two full bathrooms provide comfortable living for any household. The primary suite features a beautifully tiled shower that transforms your daily routine into something a little more luxurious. A bonus room situated above the garage offers flexible space perfect for a home office, playroom, or creative studio. Outside, the screened-in porch invites you to enjoy peaceful mornings surrounded by nature, and a detached workshop stands ready for projects big and small. The oversized utility room, complete with a mop sink, makes tackling life's messier moments refreshingly simple. Nearby Buffalo Ridge Ranch adds even more outdoor adventure to your doorstep. Properties like this — where thoughtful craftsmanship meets wide-open acreage — simply do not come along every day. Schedule your private showing and discover what country living at its finest truly feels like.
Courtesy: Keller Williams Commonwealth
859-721-2121
Charming home located on a quiet cul-de-sac in Winchester. This 4-bedroom, 2-bath home offers great potential for homeowners and investors alike. Featuring a functional layout and spacious yard, this property is ready for your personal touch. The kitchen includes a stainless steel refrigerator, with an additional refrigerator located in the basement. Enjoy a bar area in the basement, perfect for entertaining or extra living space. A covered patio provides a great outdoor area for relaxing or hosting. The home also features a full 2-car garage with attic storage and a fenced backyard for added privacy. Washer and dryer are included. The roof was replaced in 2024, offering added value and peace of mind. Conveniently located near local shopping, dining, and schools. Home is being sold as-is; inspections are welcome for buyer knowledge only. Seller is offering a 1 year home warranty!
Courtesy: United Real Estate Bluegrass
859-800-7355
Conveniently located, this charming well kept home features a functional floorplan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living area/flex space as well as an additional bedroom and bathroom. The fenced in backyard features plenty of shade and a 12'x24' storage shed. Don't miss out on this great move in ready home!
Courtesy: Coldwell Banker McMahan
859-744-1400
You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.
Courtesy: Tom Goebel & Company
859-744-3637
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!
Courtesy: Keller Williams Commonwealth
859-721-2121
Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout includes a versatile lower-level den paired with a full second bathroom, creating the perfect opportunity for a second living space, guest suite, home office, or multi-generational setup. The main level flows easily into comfortable living areas, while the upstairs features updated finishes in the full bath, adding a modern touch buyers will appreciate. Outdoor living is just as appealing with a fully fenced backyard...ideal for pets, play, entertaining, or simply enjoying private outdoor space. The attached garage is generously sized, offering not only secure parking but also excellent storage capacity. Located in a desirable, walkable area close to shopping, dining, schools, and commuter routes, this home blends comfort, convenience, and functionality in one compelling package. A rare find at this price point in Winchester...don't miss the opportunity to make it yours. Seller is offering $3,000 at closing towards Buyer closing costs, upgrades to flooring, or whatever is desired by the buyer.
Courtesy: Coldwell Banker McMahan
859-744-1400
Located in the heart of Winchester, this spacious and versatile two-story home offers incredible potential for both homeowners and savvy investors alike. With a total of 5 BR- this property provides ample space to accommodate a variety of living arrangements, from a large single-family home to a high -demand rental opportunity. The home features a welcoming covered front porch, perfect for relaxing, along with classic architectural charm that's ready to be enhanced with your personal touch. Inside the generous layout allows for flexible use of space, whether you're looking to create comfortable shared living areas or maximize rental income potential. This home is minutes from downtown shopping, dining, and everyday conveniences, this location is highly desirable for tenants and homeowners alike. Whether you are looking to expand your investment portfolio or find room to grow, this property presents a fantastic opportunity with strong upside potential.
Courtesy: Coldwell Banker McMahan
859-744-1400
This 3 BR home located in the heart of Winchester and just minutes from the vibrant downtown area, offers the perfect blend of convenience, character, and opportunity. Great opportunity for investors or homeowners. Outside you will love the spacious yard and can relax on the back deck with your morning coffee. Enjoy being within close proximity to local shops, dining, and community events- downtown Winchester is known for its historic charm, walkability, and welcoming small -town feel, all while being a short drive to Lexington. Call for your showing today. Don't miss your chance to own a piece of downtown Winchester.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining and connects to the laundry room, with access to the screened in porch, private hot tub area, and fenced backyard. A second staircase in the rear adds to the home's charm and functionality. Upstairs features a sitting area, the primary bedroom, and additional bedrooms with access to a shared full bath complete with a clawfoot tub. The finished attic or loft offers great bonus space that could be used as a fourth bedroom, rec room, or guest area and includes another full bath with a jacuzzi tub, along with unfinished attic space for additional storage. The basement level provides a large unfinished area for storage and includes an attached garage. Outside, you will find a covered side porch, a spacious side yard, a fenced backyard, and a storage shed. There is plenty of parking with a front parking pad and an extended side driveway. The home features a mix of flooring throughout and is filled with character including original doors, knobs, mantels, and four working fireplaces.
Courtesy: Marshall Lane Real Estate - Lexington
502-682-1226
***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom has a double vanity with his and her's walk in closets. You will find the other primary and 2 additional bedrooms and 2 bathrooms on the main level. The front porch invites you into the cozy living room that effortlessly flows into the dining area and updated kitchen. Out back is a deck where you can keep your grill. Perfect for entertaining the deck has stairs to the lower patio where you will find a large backyard equipped with a fire pit, storage shed and is fully fenced. The family room, laundry room and one additional bedroom are also in the basement. Two year old roof. This house has been well maintained and is perfect for the first time home buyer or those needing more space and bedrooms.
Courtesy: Rector Hayden Realtors
859-276-4811
Welcome to this beautifully maintained 5-year-old home nestled on a quiet cul-de-sac in the desirable Ft. Estill area of Winchester. This charming property offers 3 bedrooms and 2.5 baths, a spacious and functional layout with comfortable living areas perfect for both everyday living and entertaining. Enjoy low-maintenance flooring throughout all the main living areas and plenty of natural light The kitchen offers ample cabinet and counter space, a full array of SS appliances and a functional layout that flows seamlessly into the main living area and breakfast area. Just off the breakfast area is a generously sized deck overlooking the peaceful creek and farmland of adjacent property. The second-floor primary suite includes LPV flooring, a private en-suite bath with double bowl vanity and a generously sized walk-in closet, while two additional bedrooms provide flexibility for guests, a home office or hobbies. The dedicated second floor laundry area is conveniently located to all bedrooms. The finished, walk-out basement offers LPV flooring and can be used for additional living space, theater room, playroom...the possibilities are endless. The home also includes a 1-car attached garage, and energy-efficient systems (solar panels) for added convenience and large reduction on energy bills. Located just minutes from the bypass, commuting to Lexington is easy, while nearby shopping, dining and schools add to the home's appeal. Don't miss this opportunity to own a comfortable, well-located home at an excellent value. Whether you're a first-time buyer, downsizing or looking for a solid investment opportunity, this property delivers comfort, convenience and value in a growing area.
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.
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.
