Winchester Real Estate | Winchester Foreclosure Properties for Sale

26019968 MLS

Located on the very visible corner of Lexington Avenue and Main Street, this property has recently been updated. Wonderful tenants in both the upstairs and downstairs unit makes this a great investment property. The historic Leeds Center for the Arts, numerous other restaurants and shops are in walking distance. This is an ideal location for an investment property or bring your business here. This property is also located in the Opportunity Zone. Lots of options! Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, Loma's, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown! Property Highlights: -Excellent investment property with Tenants in place -Ideal location in Downtown Winchester -Located in the Opportunity Zone

1 N Main St, Winchester

$205,000

3 Beds ⋅ 3 Baths ⋅ 26019961 MLS

Welcome to **236 Buffalo Trace in Winchester, KY**—where thoughtful design meets comfortable, one-level living. This well-maintained **3-bedroom, 2.5-bath** home features a desirable **split-bedroom floor plan**, offering added privacy for the primary suite while keeping family or guest bedrooms conveniently located on the opposite side of the home. The spacious main level is designed for everyday comfort, with all bedrooms located on the first floor. Just off the kitchen, you'll appreciate the convenience of a dedicated laundry room, making daily routines a breeze. One of the home's standout features is the **spacious sunroom**, providing the perfect place to enjoy your morning coffee, unwind with a good book, or take in the peaceful views year-round. Step outside to a backyard framed by a **lush tree line**, creating a private, picturesque setting that's ideal for relaxing or entertaining. The **partially finished basement** offers valuable additional living space with endless possibilities—whether you're looking for a recreation room, home office, fitness area, or hobby space—while still providing room for storage. Conveniently located near shopping, dining, schools, and everything Winchester has to offer, this home combines a functional layout with the tranquility of a beautiful backyard setting. Don't miss your opportunity to make **236 Buffalo Trace** your next home!

236 Buffalo Trce, Winchester

$285,000

3 Beds ⋅ 2 Baths ⋅ 26019908 MLS

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

108 Milwood Dr, Winchester

$950,000

26019866 MLS

Rare opportunity to acquire approximately 120 acres of magnificent, rolling Bluegrass farmland in prime Clark County! This exceptionally versatile property features a ideal blend of cleared pasture and rich wooded land, making it perfectly suited for cattle, horses, recreational pursuits, or building your private dream estate.Equipped with a large pond, barn, and county water available at the road, this land is ready for active agricultural or equestrian use. Enjoy rolling terrain with picturesque countryside views and excellent hunting/recreational opportunities right in your back yard. Conveniently located just minutes from downtown Winchester with quick, seamless access to I-64, I-75, and the Mountain Parkway. Whether you are looking to expand an existing agricultural operation, secure a secluded hunting retreat, or establish a legacy family homestead, this property offers unmatched potential and privacy.

345 Providence Ln, Winchester

$498,000

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS

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.

1780 Stoner-Ephesus Rd, Winchester

$529,000

2 Beds ⋅ 2 Baths ⋅ 26019713 MLS

Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

443 Oxford Unit 443,445,447,449, Winchester

$785,000

5 Beds ⋅ 3 Baths ⋅ 26019610 MLS

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.

217 Wades Mill Rd, Winchester

$195,000

25000480 MLS

READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

6699 Boonesboro Rd, Winchester

$380,000

3 Beds ⋅ 2 Baths ⋅ 26019273 MLS

Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to detail throughout.The open-concept living area creates the perfect setting for entertaining or relaxing at home, while the well-designed kitchen offers abundant cabinetry, generous workspace, and appliances that convey with the home, making your move that much easier. Buyer to verify listing details. See attached improvements in documents.

125 Amiens Blvd, Winchester

$369,000

3 Beds ⋅ 2 Baths ⋅ 26019263 MLS

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

11 Stoney Brook Dr Unit 1, Winchester

$272,900

3 Beds ⋅ 2 Baths ⋅ 26019259 MLS

Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting and a small refrigerator-ideal for grilling, hosting friends, or enjoying quiet evenings at home. You'll also appreciate the screened-in back patio, offering a peaceful place to unwind while overlooking the beautifully landscaped yard. The property features mature fruit trees, including a peach and apple trees, adding both charm and seasonal enjoyment. With attractive landscaping surrounding the home and thoughtful outdoor amenities, this property is ready for you to move-in and enjoy. Don't miss the opportunity to make this wonderful home yours!

316 Buffalo Trce, Winchester

$229,000

3 Beds ⋅ 2 Baths ⋅ 26019206 MLS

Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home!

13 Long Ave, Winchester

$315,000

3 Beds ⋅ 2 Baths ⋅ 26019157 MLS

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.

4305 Old Boonesboro Rd, Winchester

$429,000

3 Beds ⋅ 3 Baths ⋅ 26019133 MLS

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.

322 Calmes Blvd, Winchester

$410,000

4 Beds ⋅ 2 Baths ⋅ 26017258 MLS

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.

351 Boone Ave, Winchester

$209,900

3 Beds ⋅ 1 Baths ⋅ 26019005 MLS

Welcome to this charming newer construction home nestled on a quiet dead-end street in Winchester! Offering 3 bedrooms and 1 full bath, this move-in-ready home features a bright, functional layout with modern finishes throughout. A standout feature is the spacious crawlspace, providing an abundance of storage for seasonal items, tools, or outdoor equipment. Enjoy the peace and privacy of low-traffic living while still being conveniently located near shopping, dining, and local amenities. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is one you won't want to miss!

30 Hughes Ave, Winchester

$239,995

3 Beds ⋅ 2 Baths ⋅ 26018986 MLS

Enjoy small town living! This 3-bedroom 2 bath budget friendly home is ready and waiting for new owners. The unique loft space adds additional space to make it your own. Sitting on just under a third of an acre which will provide a lot of outdoor space to enjoy with friends and family. The backyard is fenced for convenience and privacy. Run from the routine of renting and enjoy home ownership in this cute home. Less than 5 minutes to I64 and close to Winchester dining and shopping.

22 Apache Trl, Winchester

$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

$465,000

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

$789,000

3 Beds ⋅ 2 Baths ⋅ 26018078 MLS

**Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses, gardening, recreation, or simply taking in the scenic views, this property is ready for you to make it your own! The detached garage has a second floor office area. There are four other outbuildings for horses, hobbies, or equipment storage. Plenty of fenced areas for horses or other farm animals. The gated entrance provide privacy and security. A rare opportunity to enjoy Kentucky living at its best!

6500 Mount Sterling Rd, Winchester

$179,900

3 Beds ⋅ 2 Baths ⋅ 26017853 MLS

Welcome to 76 Clay Street in Winchester—a beautifully remodeled 3-bedroom, 2-bath home that combines modern style with everyday comfort. Completely renovated and move-in ready, this home offers quality updates throughout. Inside, you'll find durable luxury vinyl plank flooring, abundant natural light from all-new windows, and a beautifully updated kitchen featuring butcher block countertops, a farmhouse sink, and stainless steel appliances. The spacious primary suite includes a stunning tiled walk-in shower, creating the perfect private retreat. Major mechanical updates provide added peace of mind, including a new HVAC system and a new water heater. Outside, enjoy relaxing on the inviting covered front porch or entertaining guests on the back deck. This stunning home offers the perfect blend of modern updates, quality craftsmanship, and comfortable living spaces. With everything already completed, 76 Clay Street is truly move-in ready and waiting for you to call it home. Schedule your showing today and experience all this beautifully renovated property has to offer!

76 Clay St, Winchester

$374,000

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. Call to schedule a private tour while this one last.

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

$296,000

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

$235,000

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

$147,900

3 Beds ⋅ 1 Baths ⋅ 26017859 MLS

Charming and move-in ready! This freshly renovated 3-bedroom, 1-bath home in downtown Winchester offers all-new flooring and fresh paint throughout. The spacious eat-in kitchen provides plenty of room for gathering, and the in-unit washer/dryer hookup adds everyday convenience. Situated on a quiet street directly across from a park and within walking distance of the elementary school, this home offers a peaceful, family-friendly location. Enjoy the fully fenced backyard and central heat and air for year-round comfort. Ready for immediate occupancy! schedule your private tour today!

118 Park Ave, 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

$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

$319,900

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, new kitchen appliances (7/17 delivery) and additional kitchen cabinets, additional insulation, and first floor bathroom plumbing updates.

128 Cherokee Dr, Winchester

$225,000

3 Beds ⋅ 4 Baths ⋅ 26017061 MLS

This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss!

128 Abbeywood Ct, Winchester

$515,000

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

$229,900

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.

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

$274,900

4 Beds ⋅ 3 Baths ⋅ 26016975 MLS

Welcome to 304 Sandra Drive. This 4 bedroom, 2 bath ranch is quietly nestled within the desirable Westmeade subdivision. While location is obvious, this property features many updates that can be seen throughout. Multiple primary bedroom with on-suites, large backyard, new HVAC and water heater, including duct work, and so much more. Schedule your showing today!

304 Sandra Dr, Winchester

$374,900

3 Beds ⋅ 2 Baths ⋅ 26016576 MLS

Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a versatile dining room that can also serve as a home office. Don't miss the relaxing all-seasons room overlooking the professionally leveled and graded yard—perfect for morning coffee or evening gatherings. Upstairs, the private primary suite offers a generous bedroom, full bath, and three walk-in closets. An unfinished basement provides abundant storage or the opportunity to expand your living space. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in ready home offers comfort, charm, and exceptional convenience.

15 Moundale Ave, Winchester

$409,500

3 Beds ⋅ 2 Baths ⋅ 26016762 MLS

215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season.

215 Delaplain Rd, 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

$139,000

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

Winchester Foreclosure Properties for Sale

Newest Winchester Foreclosure Properties for Sale

Amanda Marcum - MARCUMsold

Search

Resources

About