Courtesy: McCallie Real Estate
859-312-7599
Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors. The home has new plumbing, as well as new wiring. A brand-new 30x40 metal garage on a concrete slab provides excellent space for vehicles, equipment, storage, or hobbies. An additional workshop area next to the garage offers even more room for projects and workspace. With 13 beautiful acres, usable land, new outbuildings, and a convenient location, this property offers a great opportunity to enjoy country living while staying close to town. Schedule your showing today!
Courtesy: Tom Goebel & Company
859-744-3637
Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent
Courtesy: Freedom Realty & Property Management
859-771-0777
Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.
Courtesy: Marshall Lane Real Estate - Lexington
502-682-1226
606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!
Courtesy: Dream Maker Realty, LLC
859-404-3384
This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.
Courtesy: RE/MAX Creative Realty
859-422-2000
Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.
Courtesy: Keller Williams Commonwealth
859-721-2121
Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!
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 minutes to Hamburg Lexington as well as Winchester and Richmond. 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: KY Local
859-536-8638
Back on the market at no fault of the sellers. Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!
Courtesy: The Agency
859-285-0614
PRICED TO SELL! 5.5% assumable mortgage! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds 2 Baths ~2,066 Total Sq Ft Full Basement Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.
Courtesy: Dream Maker Realty, LLC
859-404-3384
This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.
Courtesy: WEICHERT REALTORS - ABG Properties
859-333-7271
Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening, animals, or recreation. Take in quiet mornings, beautiful sunsets, and the charm of wide-open spaces while still being close to nearby amenities. A great opportunity to own a slice of the country and make it your own.
Courtesy: Milton and Associates Real Estate
859-983-9045
This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker
Courtesy: RO&CO Real Estate
859-487-5670
Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!
Courtesy: Bridgewater Real Estate
859-745-8632
OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
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.
Courtesy: Indigo & Co
502-735-7475
Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today!
Courtesy: Oak & Acre
859-988-2036
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.
Courtesy: Ensor Real Estate, LLC
859-749-0892
Motivated Seller, just lowered the price, seller if offering $2000 for concessions, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location
Courtesy: Keller Williams Commonwealth
859-721-2121
Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.
Courtesy: Keller Williams Commonwealth
859-721-2121
Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!
Courtesy: The Brokerage
859-983-7365
Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both beautiful and functional, with quartz countertops, a charming nook perfect for a coffee bar, a spacious walk-in pantry with floating shelves, and a wine cooler. Just off the kitchen, a dedicated dining space with a vaulted ceiling creates the perfect setting for everything from nightly dinners to effortless entertaining. The private primary suite is a true retreat, featuring a spa-like en-suite with a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom design provides added privacy, with three additional bedrooms and two full bathrooms offering plenty of space for family, guests, or a home office. Step outside to enjoy the covered back patio to relax or entertain with friends and family. And the location? Hard to beat. Just outside charming downtown Winchester, you're minutes from local shops, restaurants, and everything the community has to offer, with quick access to I-64 for an easy commute. The tall garage provides the perfect solution for vertical storage, adding even more functionality to this thoughtfully designed home.
Courtesy: Dream Maker Realty, LLC
859-404-3384
Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.
Courtesy: Dream Maker Realty, LLC
859-404-3384
Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.
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.
