Refine Search
Map
Sort by
$64,900
26018949 MLS
One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and prestige of this sought-after neighborhood. Ideally located just off I-64 at Exit 96, Royal Oaks provides quick access to downtown Winchester, shopping, dining, schools, healthcare, and the rapidly expanding Clark County Industrial Park, making it an ideal location for both convenience and long-term investment. Adding to the excitement, Royal Oaks is now expanding with Deerlawn, Clark County's newest approved master-planned single-family community. Upon completion, Deerlawn will introduce 438 new single-family homes, creating one of the region's largest residential developments and further enhancing the area's growth, amenities, and long-term value. With more than $100 million in infrastructure improvements completed and the EPA Consent Decree lifted, Clark County is positioned for continued residential and economic expansion, making now an excellent time to invest in the future of this thriving community. Whether you're ready to build today or planning for tomorrow, opportunities to own an estate-sized homesite in Royal Oaks are becoming increasingly rare. Bring your builder and create the home you've always envisioned in a community where established beauty meets exciting new growth.

102 Royal Oak Dr, Winchester
$429,000
3 Beds ⋅ 2 Baths ⋅ 26018911 MLS
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!

1024 Flanagan Station Rd, Winchester
$3,450,000
2 Beds ⋅ 3 Baths ⋅ 26018838 MLS
Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and rock walls, the farm was carefully developed for beauty and functionality. Atop a knoll at the heart of the farm is an 18th century cabin constructed from logs of the now functionally-extinct American Chestnut. Relocated and rebuilt here with modern systems, it serves as a warm and welcoming 2,275 sq. ft. main residence. Two stone fireplaces and tasteful décor contribute to the cabin's polished rustic charm. With an inviting front porch and screened side porch, as well as expansive stone patios and deck, the cabin offers many opportunities to enjoy bucolic views. An approximately 4,000 sq. ft. party barn or recreation building with restroom and custom moveable bar allows ample open space for gatherings. Two large garage doors open to the building while large windows allow abundant natural light. Nearby, a bent barn makes for an excellent workshop or storage facility. A third stock barn is perfect for equipment. The small cottage adds space for a guest or employee. The land is gently rolling, with large open fields and three ponds. Mature trees add to the landscape's verdancy. Over 440 acres adjoining the farm have been acquired by the Lower Howard's Creek Nature and Heritage Preserve, conserving the local ecosystem's many native plants and animals for perpetuity. The immense heritage and natural beauty of this farm will make it an enduring legacy for its next stewards.

510 612 Quisenberry Ln, Winchester
$350,000
25508602 MLS
Turn Key Ready! This well established business is equipped and ready for someone to live out their dream. All equipment stays. Two pool tables, barstools, tables, televisions, pool sticks, dartboard, and all inventory stays. HVAC unit, walk in compressors, and cooler recently replaced. Great location in historic downtown Winchester. One of the very few liquor stores in Kentucky that can serve mixed drinks and open liquor. The business has a very well established clientele. Sellers will sell their portfolio, which includes the apartment building next door for a negotiable price. It has three apartments that are currently rented.

137 E Broadway St, Winchester
$78,500
26018712 MLS
Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #7 is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature 438 single-family homes upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding 9,600 square feet, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off I-64 at Exit 96 and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than 20 miles from Lexington's Hamburg area, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as 80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements of approximately 1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes, creating a cohesive, attractive neighborhood designed for long-term value. With Clark County's $100+ million infrastructure improvements complete and the EPA Consent Decree lifted, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately 61 buildable lots by the end of 2026, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. Choose your homesite. Choose your builder. Build your future at Deerlawn.

241 Plantations Dr Unit LOT 7, Winchester
$78,500
26018711 MLS
**Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #6** is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature **438 single-family homes** upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding **9,600 square feet**, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off **I-64 at Exit 96** and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than **20 miles from Lexington's Hamburg area**, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as **80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements** of approximately **1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes**, creating a cohesive, attractive neighborhood designed for long-term value. With **Clark County's $100+ million infrastructure improvements complete** and the **EPA Consent Decree lifted**, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately **61 buildable lots by the end of 2026**, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. **Choose your homesite. Choose your builder. Build your future at Deerlawn.

239 Plantations Dr Unit LOT 6, Winchester
$78,500
26018710 MLS
**Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #5** is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature **438 single-family homes** upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding **9,600 square feet**, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off **I-64 at Exit 96** and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than **20 miles from Lexington's Hamburg area**, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as **80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements** of approximately **1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes**, creating a cohesive, attractive neighborhood designed for long-term value. With **Clark County's $100+ million infrastructure improvements complete** and the **EPA Consent Decree lifted**, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately **61 buildable lots by the end of 2026**, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. Choose your homesite. Choose your builder. Build your future at Deerlawn.

237 Plantations Dr Unit LOT 5, Winchester
$78,500
26018706 MLS
Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #3 is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature 438 single-family homes upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding 9,600 square feet, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off I-64 at Exit 96 and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than 20 miles from Lexington's Hamburg area, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as 80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements of approximately 1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes, creating a cohesive, attractive neighborhood designed for long-term value. With Clark County's $100+ million infrastructure improvements complete and the EPA Consent Decree lifted, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately 61 buildable lots by the end of 2026, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. Choose your homesite. Choose your builder. Build your future at Deerlawn.

233 Plantations Dr Unit LOT 3, Winchester
$78,500
26018705 MLS
Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #2 is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature 438 single-family homes upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding 9,600 square feet, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off I-64 at Exit 96 and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than 20 miles from Lexington's Hamburg area, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as 80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements of approximately 1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes, creating a cohesive, attractive neighborhood designed for long-term value. With Clark County's $100+ million infrastructure improvements complete and the EPA Consent Decree lifted, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately 61 buildable lots by the end of 2026, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. Choose your homesite. Choose your builder. Build your future at Deerlawn.

231 Plantations Dr Unit LOT 2, Winchester
$78,500
26018695 MLS
Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #4 is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature 438 single-family homes upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding 9,600 square feet, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off I-64 at Exit 96 and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than 20 miles from Lexington's Hamburg area, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as 80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements of approximately 1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes, creating a cohesive, attractive neighborhood designed for long-term value. With Clark County's $100+ million infrastructure improvements complete and the EPA Consent Decree lifted, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately 61 buildable lots by the end of 2026, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. Choose your homesite. Choose your builder. Build your future at Deerlawn.

235 Plantations Dr Unit LOT 4, Winchester
$78,500
26018697 MLS
**Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #1** is now available and ready for you to bring your own builder and create the home you've always envisioned. Deerlawn is a thoughtfully planned master-planned community that will feature **438 single-family homes** upon completion, making it one of the largest and most exciting new residential developments in Central Kentucky. Homesites are generously sized, with all lots exceeding **9,600 square feet**, providing ample space for custom homes, outdoor living, and exceptional curb appeal. Located just off **I-64 at Exit 96** and directly across from Clark County's rapidly expanding Industrial Park, Deerlawn is positioned in the heart of one of Kentucky's fastest-growing economic corridors. Less than **20 miles from Lexington's Hamburg area**, residents will enjoy convenient access to shopping, dining, healthcare, employment centers, and everything Central Kentucky has to offer while experiencing the charm and value of Winchester living. Future architectural standards are currently being finalized by the developer and are expected to include quality construction requirements such as **80% brick and/or stone exteriors, minimum roof pitch standards, and minimum heated square footage requirements** of approximately **1,600 square feet for ranch homes, 1,800 square feet for one-and-one-half story homes, and 2,100 square feet for two-story homes**, creating a cohesive, attractive neighborhood designed for long-term value. With **Clark County's $100+ million infrastructure improvements complete** and the **EPA Consent Decree lifted**, the region is experiencing unprecedented residential and commercial growth. Phase Two is already under construction, with additional phases scheduled to deliver approximately **61 buildable lots by the end of 2026**, followed by continued expansion throughout the community. Don't miss your opportunity to be among the first homeowners in one of Clark County's most anticipated new developments. **Choose your homesite. Choose your builder. Build your future at Deerlawn.

229 Plantations Dr Unit LOT 1, Winchester
$234,900
3 Beds ⋅ 2 Baths ⋅ 26018492 MLS
*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

528 Estes Dr, Winchester
$524,900
3 Beds ⋅ 3 Baths ⋅ 26018460 MLS
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.

275 Runnymeade Dr, Winchester
$259,000
3 Beds ⋅ 2 Baths ⋅ 26018346 MLS
Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner.

33 Bon-Haven Ave, Winchester
$220,000
2 Beds ⋅ 2 Baths ⋅ 26018337 MLS
Country living with the convenience of being in the city! This rare find offers over an acre of land inside the Winchester city limits with beautiful views of surrounding farmland. Relax on the spacious partially covered back deck, entertain family and friends, or enjoy plenty of room for gardening, pets, and play. The home features 2 bedrooms, 1.5 baths, and approximately 1,039 square feet of living space on the main level. The finished upstairs adds approximately 385 square feet divided into two bonus rooms currently cooled with a window A/C unit. With the addition of a permanent heat source, this space could easily serve as additional bedrooms, a home office, hobby room, or flex space. Outside you'll find an impressive detached 3-car garage with plenty of room for vehicles, a workshop, or storage, plus a separate storage building for even more space. A remote-controlled gated driveway adds convenience, privacy, and security. If you've been searching for a property that offers the feel of the country while enjoying the convenience of city living, this one checks all the boxes. Potential for second home site! Schedule your private showing today!

47 Hughes Ave, Winchester
$294,900
5 Beds ⋅ 3 Baths ⋅ 26018116 MLS
If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by. Come check this property out for yourself!

4603 Paris Rd, Winchester
$1,950,000
26018115 MLS
Located directly across from the Clark County Hospital this 12,042 office building has been occupied by the Clark County Board of Education since 1969. There is an additional 4,092 sf building located behind the main office that has been finished with office and storage space. This incredible location could be the right site for a multi-tenant renovation, single-use office, or a new beginning.

1600 W Lexington Ave, Winchester
$259,900
3 Beds ⋅ 1 Baths ⋅ 26016881 MLS
SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!!

2379 Big Stoner Rd, Winchester
$749,900
3 Beds ⋅ 3 Baths ⋅ 26017698 MLS
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!

2180 Big Stoner Rd, Winchester
$309,900
5 Beds ⋅ 2 Baths ⋅ 26017629 MLS
Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level offers a second spacious living area—perfect for a family room, game room, home office, or guest retreat. An exterior entrance to the basement adds flexibility and convenience. Situated in an established neighborhood just minutes from shopping, dining, schools, and other everyday amenities, this home combines a desirable location with a functional layout that's ready to fit your lifestyle. Don't miss your opportunity to make this Winchester home your own! Updates include new furnace, brand new kitchen appliances and additional kitchen cabinets, additional insulation, and first floor bathroom plumbing updates.

128 Cherokee Dr, Winchester
$795,000
3 Beds ⋅ 3 Baths ⋅ 26017477 MLS
**Click on the Virtual Tour section to see the video walk through!** 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.

6356 Van Meter Rd, Winchester
$435,000
26002170 MLS
This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester
$780,000
25015685 MLS
This money making car wash has three drive in bays and one automatic wash. Included with the sale is a vibrant oil change business which occupies two bays.

126 Shoppers Dr, Winchester
$219,500
3 Beds ⋅ 2 Baths ⋅ 26017144 MLS
Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping, restaurants, parks, and local amenities—all just minutes from your front door. Inside, you'll find a spacious and welcoming open floor plan with comfortable living areas, generously sized bedrooms, and plenty of natural light throughout. Whether you're a first-time home buyer, looking to downsize, or searching for the perfect home, this property offers endless potential to make it your own. Don't miss this opportunity to own a well-located home that puts everything you need within reach. Seller offering $3000.00 paint and flooring allowance to buyer with accepted contract.

491 Hidden Hills Way, Winchester
$326,000
26017069 MLS
Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property offers endless possibilities in a scenic countryside setting. Call to schedule your private viewing!

380 Howard Creek Rd Unit 380, Winchester
$219,900
26016689 MLS
Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

3686 Crowe Ridge Rd, Winchester
$134,900
2 Beds ⋅ 2 Baths ⋅ 26005794 MLS
Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full bathrooms • Large walk in shower • Wheelchair ramp for easy accessibility • Generous closet space throughout • Ample kitchen counter space • Clean, comfortable, and truly move in ready --- Exterior Features • Large corner lot offering extra privacy • Parking for up to 4 vehicles • Outbuilding for additional storage • Equipped with a Generac backup generator for peace of mind during outages --- This home offers affordable living without compromise—space, accessibility, convenience, and the security of owning your own land. $149,000

404 Mount Vernon Dr, Winchester
$1,200,000
25502866 MLS
 Prime I-1 Zoned Industrial Property - Winchester, KY Unlock the potential of this exceptional 3.9-acre parcel located in the heart of Winchester's thriving industrial corridor. Zoned I-1 (Clean Industrial), this property offers flexibility for a wide range of uses—from manufacturing and warehousing to logistics and tech operations. Property Highlights: * 3.9 Acres of flat, usable land * 7,800 Sq Ft Building with high ceilings and open layout * Power Garage Doors for easy access and loading * Utility-Ready with ample power supply * Strategic Location with quick access to major highways and local infrastructure Whether you're expanding your business, launching a new venture, or investing in a high-potential asset, this property delivers the space, zoning, and location to make it happen. The possibilities are endless—don't let this opportunity pass you by!

101 Jefferson St, Winchester
$189,000
26009146 MLS
Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and old roadbeds provides easy access throughout the property, making it ideal for exploring, hiking, or ATV use. Whether you're looking to build your dream home tucked among the trees or create a peaceful weekend escape, this property delivers the privacy and tranquility you've been searching for. A small barn adds utility, while the location offers convenient access to the Mountain Parkway, making travel to Winchester and surrounding areas simple and efficient. Don't miss this opportunity to own a versatile piece of Kentucky land with endless possibilities—recreation, investment, or your future homesite all in one.

2697 Pine Ridge Rd, Winchester
$124,500
2 Beds ⋅ 1 Baths ⋅ 26000228 MLS
Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester