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$110,000
26024261 MLS
Discover the perfect setting for your dream home on this beautiful 4.14-acre tract at 3999 Bybee Road, Winchester, KY 40391. Nestled among the rolling hills of Kentucky's Bluegrass region, this picturesque property offers stunning panoramic countryside views and the peace and privacy you've been searching for. The gently rolling terrain provides multiple potential building sites, giving you the flexibility to design the home you've always envisioned while enjoying breathtaking views in every direction. With approximately 4.14 acres of open land, there's plenty of room for a custom home, detached garage, workshop, barn, or hobby farm. Existing fencing is located along portions of the property, and the surrounding landscape creates a quiet, scenic setting that's perfect for enjoying nature, watching wildlife, or simply relaxing after a long day. Located just minutes from downtown Winchester, you'll enjoy the best of both worlds: peaceful country living with convenient access to shopping, dining, schools, and I-64 for an easy commute to Lexington. Whether you're ready to build now or invest in a beautiful piece of Kentucky countryside for the future, this exceptional property offers endless possibilities. Don't miss this rare opportunity to own 4.14 acres in one of Clark County's most desirable rural settings.

3999 Bybee Rd, Winchester

$165,000
3 Beds 1 Baths 26024016 MLS
Conveniently located in Winchester, this one-story home offers three bedrooms, one bath, and plenty of potential for a first-time buyer or investment property. Inside, you'll find laminate and vinyl flooring throughout, a spacious kitchen, and a separate laundry room. The bathroom received new fixtures in 2025, while the roof is approximately 1.5 years old, taking care of two worthwhile updates for the next owner. Gas freestanding heaters provide heat, and the home does not currently have central air. Outside, there's a covered front porch and a nice-sized backyard with an alley running behind the property. Whether you're looking for an affordable place to call your own or an addition to your rental portfolio, this home is ready for its next chapter.

209 E Washington St, Winchester

$135,000
2 Beds 1 Baths 26023193 MLS
Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees, countryside, and views. A metal roof adds practicality, and the property's location near the Kentucky River provides easy access to one of the area's notable natural features. Whether you're looking for a primary residence, weekend getaway, or a smaller property with a little room around it, 3208 Ford Hampton Road offers a straightforward home in a scenic rural setting.

3208 Ford Hampton Rd, 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

$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

$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

$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

$165,000
4 Beds 3 Baths 26008701 MLS
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester

$78,500
26011488 MLS
NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion.

Lot 4 Plantations, Winchester

$78,500
26011487 MLS
NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion.

Lot 3 Plantations, Winchester