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$1,700,000
3 Beds 3 Baths 26009046 MLS
Rare opportunity to own 187+/- acres in the heart of Ohio County, Kentucky at 3087 Halls Creek Rd, Olaton. This impressive multi use property offers a combination of recreation, income potential, privacy, natural beauty, and country lifestyle that is increasingly difficult to find in today's market. Whether you are searching for a premier hunting farm, family retreat, weekend escape, working farm, or long term land investment, this property checks an exceptional number of boxes. At the center of the property is a beautiful private lake positioned just steps from one of the residences, creating a setting where you can walk out the front door and be fishing within moments. Additional ponds and creeks enhance both the usability and beauty of the farm while also supporting wildlife habitat and year round enjoyment. Rolling topography, scenic fields, wooded ridges, and stunning sunset views create a landscape that feels private, peaceful, and timeless. Ohio County is widely recognized as one of Kentucky's premier hunting regions and has consistently produced trophy caliber whitetails, including Boone & Crockett and Pope & Young genetics. This farm offers the type of habitat serious outdoorsmen seek with food sources, water, cover, travel corridors, and strong surrounding area genetics. Turkey populations in the area are also excellent, making this an outstanding recreational tract for multiple seasons. The property includes productive crop ground that can provide annual lease income while also serving as a food source for wildlife. Mature hardwood timber adds additional investment appeal with potential value through properly managed select cutting. The combination of recreational enjoyment and income opportunities makes this a rare asset that can be enjoyed today while also holding long term upside. Two homes are located on the property and offer flexible future use. While they may benefit from updates, they provide excellent potential for hunting lodge accommodations, guest homes, rental income, caretaker housing, or a private family compound. Large hunting groups or multiple families will appreciate the ability to comfortably utilize the farm together. Located near Rosine, Kentucky, this area is known as the birthplace of Bluegrass music and home to the legacy of Bill Monroe. Beyond the property lines, the region offers a rich heritage, welcoming rural community, and a slower pace of life that many buyers are actively seeking. If you have been searching for a place to escape the city, build memories with family and friends, hunt trophy deer, fish your own private waters, generate farm income, and own a true Kentucky legacy property, 3087 Halls Creek Rd deserves your attention. Properties with this blend of acreage, water, wildlife, income potential, and multiple residences are rarely available.

3087 Halls Creek Rd, Olation

$1,700,000
26007718 MLS
Exceptional 216-acre equine farm in the heart of Bourbon County, located on scenic Cane Ridge Road in Paris, Kentucky—an area renowned for world-class horse operations. Designed with functionality and versatility in mind, the property is well-suited for training, boarding, or breeding. The centerpiece is a 150' x 100' steel-framed indoor riding arena, ideal for year-round riding and training. A converted 10-stall barn offers immediate stabling, complemented by additional farm structures including a tobacco barn for hay storage, hoop barn, and a 24' x 40' metal building with concrete floor for equipment or feed. Water is abundant and thoughtfully distributed, with three live springs, multiple ponds, and auto waterers throughout the farm, supporting efficient pasture management and livestock care. The property also includes a cabin currently utilized as a tack room, with potential for office or staff use. Gently rolling acreage offers excellent pasture layout potential for paddocks, turnout, and further equine improvements. A rare opportunity to acquire a well-located horse farm in one of Kentucky's most desirable equine regions.

3386 Cane Ridge Rd, Paris

$1,695,000
5 Beds 4 Baths 26015066 MLS
Discover this remarkable 54-acre property in the heart of Woodford County, offering a unique combination of privacy, functionality, and scenic beauty. The main residence features 5 bedrooms, 4 full baths, and over 4,500 square feet of finished living space, including a 2-car attached garage. Located at the rear of a working Thoroughbred farm, the home enjoys stunning views of the Kentucky River and surrounding woodlands. A spacious walk-out basement includes a full bath and kitchenetteâ€"ideal for guest quarters or a multigenerational layout. Additional features include a two-zone geothermal HVAC system and a large rear deck overlooking the river. The property also includes a barn, indoor arena, and two tenant houses. Furnishings in the primary residence are available for purchase.

2309 Oregon Rd, Versailles

$1,695,000
2 Beds 2 Baths 26011397 MLS
Welcome to Blue Palm on Jessamine Creek, a curated lifestyle property for a buyer who values design, serenity, and rarity. Set along the tranquil banks of Jessamine Creek, this extraordinary estate presents a once-in-a-generation opportunity to own a true legacy property where modern luxury and untouched natural beauty exist in perfect harmony. Spanning nearly 7 breathtaking acres, this private sanctuary offers an immersive connection to nature with abundant wildlife including deer, turkey, fox, otters, geese, ducks, and soaring eagles creating an ever-changing backdrop of serenity and wonder. Architecturally refined with a sophisticated modern aesthetic, the residence was thoughtfully curated with exceptional attention to detail. Two luxurious ensuite bedrooms provide refined comfort, while the stunning great room is framed by expansive views overlooking the creek and seamlessly flows into a covered and screened outdoor living space designed for entertaining. The custom-milled kitchen cabinetry and integrated storage solutions elevate both form and function, delivering a level of craftsmanship rarely found in today's market. For collectors, hobbyists, or automotive enthusiasts, the detached heated and cooled three-car garage is an exceptional extension of the property—offering the perfect private showroom or workshop environment. Above, approximately 1,000 square feet with rough-in plumbing provides endless possibilities for a guest retreat, studio, executive office, or personalized expansion tailored to your vision. Equal parts retreat and statement property, this remarkable offering delivers the privacy, sophistication, and lifestyle typically reserved for the most distinguished trophy estates.

2231 Glass Mill Rd, Wilmore

$1,650,000
6 Beds 4 Baths 26023485 MLS
A luxurious 6-bed, 3.5-bath estate with over 5,000 sq ft of finished living space, a 1,444 sq ft finished garage, and 800+ sq ft of covered porches on a manicured 1-acre lot. Located just a half-mile from I-64, the home boasts painted Meridian brick, 3,200+ sq ft of manufactured stone, and 1,000 sq ft of paver patios. Andersen 400-Series Woodwright windows, precast stone accents, and LED soffit lighting create stunning curb appeal. Inside, enjoy a 45-SEER geothermal system, smart thermostats, Rockwool insulation, and energy bills averaging just 207/month. The resort-style backyard features a heated 20x38 pool, hot tub, gas fire pit, pool bath, and 6' privacy fence. Chef's kitchen includes Kraftmaid cabinets, quartzite counters, Sub-Zero/Wolf/Cove appliances, and hidden pantry. Interior finishes include custom showers, tray ceilings, solid trim, and Poplar closet systems. Added luxuries: 4-car garage, security system, attic storage, tankless water heater, and premium fixtures throughout.

101 Welsley Way, Mt Sterling

$1,650,000
6 Beds 6 Baths 26006604 MLS
If you are looking for a home that offers space to unwind from daily demands—along with room for entertaining, celebrations, hobbies, or even a horse or small animal operation—this property delivers. With abundant indoor and outdoor entertaining areas, the shed-row barn offers flexible use as a horse facility, workshop, "she-shed," hobby space, or storage. Set on 10 acres, this is a property where imagination can truly take hold. The home has been spectacularly remodeled by Creative Kitchen and Bath. Impeccably maintained, it was taken down to the studs and completely renovated from top to bottom. Features include new hardwood floors, detailed moldings, new kitchens on both the main level and the basement, new bathrooms throughout, new windows and doors, high-speed broadband, a central vacuum system, a high-powered security system, and a Bluegrass home movie theatre entertainment system. All bedrooms include walk-in closets with custom-designed wood shelving. The lower level offers a separate entrance, making it ideal for a mother-in-law suite or apartment, complete with a full walkout, multiple French doors, and wall-to-wall windows. The property is being sold furnished, with furnishings included in the current price, and is priced under recent appraisal. The location combines convenience with a true country feel—close to shopping in Hamburg and directly across from Hisle Farm Park. The park spans approximately 280 acres of rolling pastureland located five miles northeast of downtown Lexington at 3601 Briar Hill Road. It features shared-use trails for horseback riding and hiking, including 1- and 2.5-mile loops, a 10-lane target archery range, and is open from dawn until dusk. Pets are welcome but must be leashed. Priced $540,000 below recent appraisal!!!

3600 Briar Hill Rd, Lexington

$1,650,000
6 Beds 6 Baths 26007206 MLS
If you are looking for a home that offers space to unwind from daily demands—along with room for entertaining, celebrations, hobbies, or even a horse or small animal operation—this property delivers. With abundant indoor and outdoor entertaining areas, the shed-row barn offers flexible use as a horse facility, workshop, "she-shed," hobby space, or storage. Set on 10 acres, this is a property where imagination can truly take hold. The home has been spectacularly remodeled by Creative Kitchen and Bath. Impeccably maintained, it was taken down to the studs and completely renovated from top to bottom. Features include new hardwood floors, detailed moldings, new kitchens on both the main level and the basement, new bathrooms throughout, new windows and doors, high-speed broadband, a central vacuum system, a high-powered security system, and a Bluegrass home movie theatre entertainment system. All bedrooms include walk-in closets with custom-designed wood shelving. The lower level offers a separate entrance, making it ideal for a mother-in-law suite or apartment, complete with a full walkout, multiple French doors, and wall-to-wall windows. The property is being sold furnished, with furnishings included in the current price, and is priced under recent appraisal. The location combines convenience with a true country feel—close to shopping in Hamburg and directly across from Hisle Farm Park. The park spans approximately 280 acres of rolling pastureland located five miles northeast of downtown Lexington at 3601 Briar Hill Road. It features shared-use trails for horseback riding and hiking, including 1- and 2.5-mile loops, a 10-lane target archery range, and is open from dawn until dusk. Pets are welcome but must be leashed. Priced $540,000 below recent appraisal!!!

3600 Briar Hill Rd, Lexington

$1,650,000
4 Beds 5 Baths 26013594 MLS
Built as an architectural replica of the George Wythe house in Williamsburg, VA, this classic colonial home sits on 10+ beautiful acres in sought-after Woodford County. As you pull into the scenic, private drive, you will come upon the home and its undeniable pride of ownership. Once inside the door, the grand foyer will introduce you to the rich feel of the home and the warmth it exudes. Flanked on either side of the grand foyer are the dining room with a fireplace and study, complete with bookshelves, a fireplace, and an attached renovated half bath. The large family room adjoins the flex space with a wet bar and custom cabinetry with an icemaker and wine fridge. Nearby is an entry into the spacious screened porch. Tucked away is the spacious primary suite with a lovely fireplace, a large walk-in closet, and en suite bath. The chef's kitchen is a true delight and offers a stunning island as the centerpiece. The commercial range and custom cabinet front refrigerator and freezer, as well as the well-designed soft shut cabinets and drawers, offer design-specific cabinets such as a spice rack, pan storage, etc. The large laundry room with a slop sink is off the kitchen and offers a mud room that connects it to the three-car garage with loads of space for storage. Up the back staircase, a family room gives way to a hallway where three large bedrooms with nice closets and two renovated full bathrooms with marble and custom cabinets await. The third floor offers space for the new homeowner to use as a playroom, gym, office, or whatever works for their needs. Outside the home will not disappoint! With almost eleven acres to enjoy, the property offers something for everyone. The new Amish-built barn is complete with two large 12 x 12 stalls and plenty of room for storage. Horses will have room to roam and relish in the 3 pastures complete with four-board fencing with electrical lining. A play yard near the home and a turf pad behind the house offer hours of play in the great outdoors. The view beyond the pastures will make anyone want to call 4001 Shannon Run Road home for years to come!

4001 Shannon Run Rd, Versailles

$1,645,000
5 Beds 4 Baths 26016949 MLS
Welcome to 305 Beech Street, a truly special Tudor-inspired home tucked along year-round Elk Creek in the heart of Monticello. Located within the city limits, this 23 +/- acre unique property offers the convenience of town with the peaceful feel of country living. Lovingly designed and enjoyed for generations, it is a place filled with beauty, character, and history. A winding asphalt driveway shaded by mature dogwood trees and lined with carefully trimmed evergreens welcomes you home. Inspired by the owners' travels through Europe, the grounds feature expansive lawns, mature shade trees, and a beautiful formal French garden with brick-lined beds, statuary, boxwoods, flowering arches of Sweet Autumn Clematis, a vegetable garden, and an automated irrigation system. In the spring, hundreds of daffodils bloom throughout the property, while the shady creekside setting provides the perfect place for picnics, cookouts, and simply enjoying nature. Built of native mountain stone, stucco, and custom milled fir trim, the home reflects exceptional craftsmanship and timeless style. A two-level screened gazebo porch with sliding glass windows creates a wonderful space to enjoy in every season. Inside, soaring beamed ceilings, hand-painted details, custom stained glass, beautiful millwork, and Italian porcelain flooring create a warm and inviting atmosphere. The spacious great room is centered around a striking custom stone fireplace with a heatilator system and flows easily into the dining room overlooking Elk Creek. The kitchen is both beautiful and functional, featuring custom cabinetry, quartz countertops, a center island, walk-in pantry, GE Monogram dual-fuel six-burner range with double ovens, KitchenAid appliances, and a cozy bay window breakfast area with views of the creek. The main-level primary suite offers an 11-foot beamed ceiling, stone fireplace with gas logs, sitting area, private deck, large walk-in closet, and a luxurious bath with heated floors, double shower, and clawfoot soaking tub. A guest bedroom and bath are also conveniently located on the main level. Upstairs is an additional private suite with custom built-ins, dormer windows, abundant storage, and its own bath. The walk-out basement provides generous additional living space with a fireplace, recreation areas, two more bedrooms, including one with an en suite bath, and plenty of storage. Additional features include three separate HVAC systems, an automatic generator, oversized garage, city water and sewer, and a new roof installed in May 2026. Rich in local history and surrounded by natural beauty, 305 Beech Street is more than just a house. It is a place where memories have been made for generations and where the next owners will have the opportunity to enjoy a truly remarkable setting along Elk Creek. Convenient location near Lake Cumberland in South Central Kentucky!

305 Beech St, Monticello

$1,645,000
5 Beds 4 Baths 26016942 MLS
Welcome to 305 Beech Street, a truly special Tudor-inspired home tucked along year-round Elk Creek in the heart of Monticello. Located within the city limits, this 23 +/- acre unique property offers the convenience of town with the peaceful feel of country living. Lovingly designed and enjoyed for generations, it is a place filled with beauty, character, and history. A winding asphalt driveway shaded by mature dogwood trees and lined with carefully trimmed evergreens welcomes you home. Inspired by the owners' travels through Europe, the grounds feature expansive lawns, mature shade trees, and a beautiful formal French garden with brick-lined beds, statuary, boxwoods, flowering arches of Sweet Autumn Clematis, a vegetable garden, and an automated irrigation system. In the spring, hundreds of daffodils bloom throughout the property, while the shady creekside setting provides the perfect place for picnics, cookouts, and simply enjoying nature. Built of native mountain stone, stucco, and custom milled fir trim, the home reflects exceptional craftsmanship and timeless style. A two-level screened gazebo porch with sliding glass windows creates a wonderful space to enjoy in every season. Inside, soaring beamed ceilings, hand-painted details, custom stained glass, beautiful millwork, and Italian porcelain flooring create a warm and inviting atmosphere. The spacious great room is centered around a striking custom stone fireplace with a heatilator system and flows easily into the dining room overlooking Elk Creek. The kitchen is both beautiful and functional, featuring custom cabinetry, quartz countertops, a center island, walk-in pantry, GE Monogram dual-fuel six-burner range with double ovens, KitchenAid appliances, and a cozy bay window breakfast area with views of the creek. The main-level primary suite offers an 11-foot beamed ceiling, stone fireplace with gas logs, sitting area, private deck, large walk-in closet, and a luxurious bath with heated floors, double shower, and clawfoot soaking tub. A guest bedroom and bath are also conveniently located on the main level. Upstairs is an additional private suite with custom built-ins, dormer windows, abundant storage, and its own bath. The walk-out basement provides generous additional living space with a fireplace, recreation areas, two more bedrooms, including one with an en suite bath, and plenty of storage. Additional features include three separate HVAC systems, an automatic generator, oversized garage, city water and sewer, and a new roof installed in May 2026. Rich in local history and surrounded by natural beauty, 305 Beech Street is more than just a house. It is a place where memories have been made for generations and where the next owners will have the opportunity to enjoy a truly remarkable setting along Elk Creek. Convenient location near Lake Cumberland in South Central Kentucky!

305 Beech St, Monticello

$1,645,000
26014095 MLS
Prime 47+/- acre opportunity near I-24 Exit 16 in Paducah, KY! This beautiful property, historically used as a cattle farm, offers endless potential for agricultural, residential, commercial, or mixed-use development. Featuring over 700 feet of I-24 frontage and additional frontage along US Hwy 68/Benton Road, this site provides excellent visibility and accessibility. Located less than a mile from Exit 16, the property sits in a growing corridor surrounded by established commercial businesses and ongoing development, including Southern Pride Auto/Truck Plaza, with steady daily traffic and semi-truck flow. The land is mostly flat and usable with utilities available at Benton Road. Zoned partially UR and partially Commercial, allowing flexibility for multiple uses. Seller proposes to subdivide into Tract A (28 acres) and Tract B (19 acres). Additional subdivision options available at $35,000 per acre, subject to survey.

7150 Benton Rd, Paducah

$1,625,000
4 Beds 2 Baths 26025190 MLS
Welcome to an extraordinary opportunity to own a thriving boutique winery nestled on nearly 26 breathtaking acres in the rolling countryside of Adair County. This turnkey estate offers the rare chance to embrace a lifestyle where passion meets purpose, with every detail thoughtfully established and ready for its next owner. At the heart of the property is a stunning 4-bedroom residence, perfectly positioned to capture panoramic views of the vineyards from its expansive front porch—the ideal setting to enjoy peaceful mornings and unforgettable sunsets overlooking your own vines. The winery features a newly constructed tasting room and café offering over 1,300 square feet of inviting retail and guest space, complemented by an additional 1,600 square feet of kitchen and production/workshop space designed to support both current operations and future growth. Every bottle tells the story of the land, with wines handcrafted exclusively from estate-grown grapes. The vineyard showcases an impressive selection of varietals including Norton, Chambourcin, Niagara, Foch, White Cayuga, Fredonia, and Catawba, creating a truly authentic vineyard-to-glass experience. Adding even more versatility, the property includes a 14' x 50' mobile home currently serving as in-law quarters, a detached garage, and ample acreage with endless possibilities for expansion. Envision additional vineyard plantings, luxury accommodations, or transforming this picturesque estate into a premier wedding and special events venue. The sale includes all wine-making equipment and proprietary recipes, allowing for a seamless transition into ownership. Even better, the transferable liquor license provides an exceptional advantage, making it easier to continue and grow this established business. Whether you're an experienced vintner, an entrepreneur pursuing a dream, or someone seeking an unparalleled lifestyle investment, this remarkable estate offers everything you've been searching for. The hard work has already been done—simply step in and begin the next chapter. Live where you work. Create where you inspire. Welcome home to your own private vineyard paradise.

150-182 Combest Dr, Columbia

$1,625,000
4 Beds 4 Baths 26010143 MLS
Extraordinary Woodford County lifestyle property offering 80 rolling acres, sweeping views, abundant wildlife, and the kind of privacy and versatility that is increasingly hard to find. The approximately 4,500 square foot residence features 4 bedrooms, 3.5 baths, updated baths, a cook's kitchen with gas cooktop and three wall ovens, and multiple gathering spaces designed for everyday living and entertaining alike. A large deck captures long countryside views, while the covered brick patio creates the perfect setting for quiet mornings, sunset evenings, and watching deer and turkey move across the property. The walkout basement functions almost like a private apartment with its own kitchen, living area, bunk room (egress window does not meet current code requirements for bedroom classification), and full bath, ideal for guests, extended family, caretaker quarters, or flexible rental use subject to buyer verification. Outside, the property continues with an approximately 40x60 shop and 100x40 barn, providing space for equipment, hobbies, storage, livestock, or future creative use. Rolling hills, partial woods, open pasture, and a peaceful setting combine to create a property equally suited for recreation, entertaining, weekend escapes, or full time Kentucky country living. Properties offering this combination of scenery, usability, comfort, and privacy rarely come available.

5108 Fords Mill Rd, Versailles

$1,625,000
26015020 MLS
Welcome to an extraordinary opportunity to own a thriving boutique winery nestled on nearly 26 breathtaking acres in the rolling countryside of Adair County. This turnkey estate offers the rare chance to embrace a lifestyle where passion meets purpose, with every detail thoughtfully established and ready for its next owner. At the heart of the property is a stunning 4-bedroom residence, perfectly positioned to capture panoramic views of the vineyards from its expansive front porch—the ideal setting to enjoy peaceful mornings and unforgettable sunsets overlooking your own vines. The winery features a newly constructed tasting room and café offering over 1,300 square feet of inviting retail and guest space, complemented by an additional 1,600 square feet of kitchen and production/workshop space designed to support both current operations and future growth. Every bottle tells the story of the land, with wines handcrafted exclusively from estate-grown grapes. The vineyard showcases an impressive selection of varietals including Norton, Chambourcin, Niagara, Foch, White Cayuga, Fredonia, and Catawba, creating a truly authentic vineyard-to-glass experience. Adding even more versatility, the property includes a 14' x 50' mobile home currently serving as in-law quarters, a detached garage, and ample acreage with endless possibilities for expansion. Envision additional vineyard plantings, luxury accommodations, or transforming this picturesque estate into a premier wedding and special events venue. The sale includes all wine-making equipment and proprietary recipes, allowing for a seamless transition into ownership. Even better, the transferable liquor license provides an exceptional advantage, making it easier to continue and grow this established business. Whether you're an experienced vintner, an entrepreneur pursuing a dream, or someone seeking an unparalleled lifestyle investment, this remarkable estate offers everything you've been searching for. The hard work has already been done—simply step in and begin the next chapter. Live where you work. Create where you inspire. Welcome home to your own private vineyard paradise.

150-182 Combest Dr, Columbia

$1,625,000
4 Beds 4 Baths 26010138 MLS
Extraordinary Woodford County lifestyle property offering 80 rolling acres, sweeping views, abundant wildlife, and the kind of privacy and versatility that is increasingly hard to find. The approximately 4,500 square foot residence features 4 bedrooms, 3.5 baths, updated baths, a cook's kitchen with gas cooktop and three wall ovens, and multiple gathering spaces designed for everyday living and entertaining alike. A large deck captures long countryside views, while the covered brick patio creates the perfect setting for quiet mornings, sunset evenings, and watching deer and turkey move across the property. The walkout basement functions almost like a private apartment with its own kitchen, living area, bunk room (egress window does not meet current code requirements for bedroom classification), and full bath, ideal for guests, extended family, caretaker quarters, or flexible rental use subject to buyer verification. Outside, the property continues with an approximately 40x60 shop and 100x40 barn, providing space for equipment, hobbies, storage, livestock, or future creative use. Rolling hills, partial woods, open pasture, and a peaceful setting combine to create a property equally suited for recreation, entertaining, weekend escapes, or full time Kentucky country living. Properties offering this combination of scenery, usability, comfort, and privacy rarely come available.

5108 Fords Mill Rd, Versailles

$1,600,000
5 Beds 5 Baths 26022884 MLS
What you're looking at today started more than 100 years ago as a working barn, one with deep ties to Kentucky's Thoroughbred history. In 2019, it was extensively renovated and thoughtfully transformed into the one-of-a-kind home you see today. Throughout the conversion, the character and history of the original structure were preserved while creating a residence designed for modern living. The result is a property filled with architectural details you simply can't recreate in a new build, complemented by polished concrete floors, custom murals by local artist Wylie Caudill and modern systems and finishes throughout. The first floor offers two living spaces, a dining area and gas fireplace, along with two bedrooms, two walk-in closets and two spacious full bathrooms. The kitchen features stainless steel appliances and a large island with granite countertops, while the baths include quartz-topped vanities, tiled showers and a Whirlpool tub. Accessible from the main residence, the second floor offers multiple flexible spaces, including a studio apartment-style layout with a full bathroom, wet bar and large walk-in closet. Two additional private apartments are accessed by their own separate entrances and spiral staircases, each featuring a bedroom, full bathroom and wet bar/kitchenette with mini refrigerator. These spaces offer exceptional flexibility for guests, extended family, staff or potential short-term rental income. Set on 1.797 acres surrounded by farmland, the outdoor spaces are equally impressive. The saltwater pool features bubble lights, a stamped-concrete deck, new waterfall, 2026 liner and pool cover, while a hot tub provides another place to relax and unwind. A detached four-car garage offers abundant parking along with two large unfinished multi-purpose spaces ready to adapt to the next owner's needs. Behind the historic character is modern infrastructure designed for comfort, convenience and even self-sufficiency. All major systems date to 2019 or newer and include mini-split heating and cooling, a tankless water heater with plumbing in place for a second system if needed, septic system, Pella windows along the rear of the home and garage, and an automatic generator utilizing solar and gas. The property is even equipped with the ability to operate off-grid if needed, and the asphalt driveway was redone in 2026. But what makes this property especially interesting is what it could become for its next owner. It can be an extraordinary private residence, a memorable setting for hosting and hospitality, or an opportunity to combine your home with potential income from the property's private apartments. More than a century of history, reimagined for what's next. Being sold as-is, with inspections welcome! ***Seller is also offering owner-financing.***

3495 Ky-32, Cynthiana

$1,600,000
3 Beds 2 Baths 26018393 MLS
Opportunity abounds with this exceptional 145± acre property offering a rare combination of open, level land, development potential, and an unfinished custom home. Surrounded by beautiful countryside, the property features expansive, gently rolling fields bordered by mature trees, with a picturesque creek along one boundary, creating both privacy and scenic appeal. The property is fenced and includes a 3,000+ sq. ft. unfinished home with an attached 3-car garage and a full basement, providing the perfect opportunity to customize your dream residence or investment property.Originally planned as a residential subdivision, a recorded plat is already on file, making this an outstanding opportunity for future development, while also lending itself to farming, equestrian use, or a private country estate. Conveniently located just minutes from the welcoming town of Liberty, you'll enjoy easy access to restaurants, grocery stores, schools, and medical facilities. Outdoor enthusiasts will appreciate being less than 30 minutes from both Lake Cumberland and Green River Lake, offering endless opportunities for boating, fishing, and recreation.Whether you're an investor, developer, farmer, or someone searching for an extraordinary place to build your forever home, this unique property is ready to bring your vision to life.

7255 Kentucky 70, Liberty

$1,600,000
4 Beds 4 Baths 26016832 MLS
Nestled on 48 breathtaking acres, this extraordinary custom-built brick estate offers a rare combination of luxury, comfort, and timeless craftsmanship. From the moment you step inside, you'll appreciate the quality found throughout, including gleaming hardwood floors, granite countertops, custom finishes, and five beautiful fireplaces that create warmth and character in every season. The spacious first-floor primary suite serves as a private retreat, featuring generous proportions and ensuite bath designed for relaxation. Upstairs, a second owner's suite offers its own fireplace, Jacuzzi tub, and private space that's ideal for guests or multi-generational living. Two additional bedrooms provide ample room for family and visitors, while four full bathrooms ensure everyone enjoys comfort and convenience. The elegant formal dining room is perfectly suited for large holiday gatherings, dinner parties, and family celebrations. Just beyond the dining room and kitchen is the inviting den is filled with oversized windows that showcase the property's spectacular views, filling the space with natural light while overlooking beautifully landscaped gardens and rolling countryside. Whether enjoying a quiet morning coffee or watching the seasons change, this room is sure to become a favorite. Multiple living areas throughout the home provide flexibility for entertaining, relaxing, or working from home, while the unfinished basement offers endless possibilities for future expansion, storage, a workshop, or recreation space. Outside, the property is every bit as impressive. Covered porches invite you to slow down and enjoy peaceful Kentucky sunsets, while the outdoor fireplace creates the perfect backdrop for entertaining family and friends year-round. The surrounding 48 acres of pristine farmland provide exceptional privacy, stunning views, and endless opportunities for farming, recreation, horses, or simply enjoying the beauty of the land. 7 stall horse barn with tack room, electric and water complete this magnificent property. The home and acreage may be purchased together as one remarkable estate or separately. Properties offering this level of craftsmanship, privacy, and versatility are truly few and far between.

5845 Ky Highway 590 A, Lancaster

$1,600,000
26004674 MLS
Farms of this size and in this location are an incredibly rare offering. Held by the same family since 1946, these 142+ acres of varied terrain rest at the end of Old Dry Branch Road. An ideal Fayette County address affords convenience (15 minutes to Man o' War Blvd.) while maintaining remarkable privacy and seclusion. The terrain includes open pasture, dense woods, and deep valleys with streams flowing to the Kentucky River. Native species and innumerable trees evoke early Kentucky, while two ponds contribute to the bucolic setting. Wildlife including bobcats, great blue heron, kingfishers, and peregrine falcons have often been spotted nearby. Ideally suited for outdoor pursuits, opportunities abound for hiking, hunting, fishing, trail riding, canoeing or kayaking. Long-admired for its natural beauty, the Kentucky River Palisades region of Fayette County is also home to Raven Run Nature Sanctuary, Floracliff Nature Sanctuary, and the new Kelley's Landing park. This 450-million-year-old ecosystem includes breathtaking limestone formations and numerous springs & caves. Note: the farm is not yet enrolled in the LFUCG PDR program or similar, which may offer additional value to a new owner. Call for specific details.

7600 Old Dry Branch Rd, Lexington

$1,599,999
4 Beds 3 Baths 26006686 MLS
Dreaming of wide open space, privacy, and a property that truly does it all? This one isn't just rare—it's nearly impossible to duplicate. Welcome to 42.7 acres of fully usable land designed for the way you want to live—perfectly positioned in the heart of Central Kentucky, where you get the best of both worlds: peaceful, private country living with the convenience of being just a short drive to nearby towns, dining, and everyday essentials. Whether you're running cattle, hunting, riding, trying to hide from the world, or simply soaking in the scenery, this location delivers the lifestyle so many are searching for. And just when you think it couldn't get better—lake access with your own private shoreline takes it to another level. Built in 2022, the custom contemporary barndominium-style, stick-built home offers over 2,070 square feet of thoughtfully designed living space with 4 bedrooms and 3 full baths. From the moment you arrive, the wraparound porch—complete with stunning wood accent ceilings—sets the tone for what's inside: warm, elevated, and intentionally designed to take in the surrounding views. Step inside to an open-concept layout filled with natural light and enhanced by an abundance of recessed lighting. The kitchen is a true centerpiece, featuring quartz countertops, a statement oversized island, stainless appliances, and an impressive amount of soft-close custom cabinetry—perfect for both everyday living and entertaining. The primary suite is a retreat of its own, showcasing a tiled walk-in shower with rain head, double vanities, and a spacious walk-in closet. Both interior baths are finished with double vanities, offering convenience and style throughout. But perhaps what truly sets this property apart is everything beyond the home: a 4,000 sq ft attached insulated shop with 16 ft ceilings, two pull-through, double-sided 14 ft garage doors (2-post car lift included), a 50x30 metal barn with electric and automatic waterer, new perimeter fencing already in place, and an incredible 2,400 feet of road frontage. All of this, located within the highly sought-after Burgin school district, known for its strong performance and tight-knit community feel—making it just as appealing for those prioritizing education as it is for those seeking land and lifestyle. This is more than a home—it's a lifestyle property that checks every box: land, luxury, functionality, and freedom, all in a location that's hard to beat. Opportunities like this don't come around often... and when they do, they don't last.

279 Dossett Ln, Harrodsburg

$1,599,999
4 Beds 3 Baths 26006809 MLS
Dreaming of wide open space, privacy, and a property that truly does it all? This one isn't just rare--it's nearly impossible to duplicate. Welcome to 42.7 acres of fully usable land designed for the way you want to live--perfectly positioned in the heart of Central Kentucky, where you get the best of both worlds: peaceful, private country living with the convenience of being just a short drive to nearby towns, dining, and everyday essentials. Whether you're running cattle, hunting, riding, trying to hide from the world, or simply soaking in the scenery, this location delivers the lifestyle so many are searching for. And just when you think it couldn't get better--lake access with your own private shoreline takes it to another level. Built in 2022, the custom contemporary barndominium-style, stick-built home offers over 2,070 square feet of thoughtfully designed living space with 4 bedrooms and 3 full baths. From the moment you arrive, the wraparound porch--complete with stunning wood accent ceilings--sets the tone for what's inside: warm, elevated, and intentionally designed to take in the surrounding views. Step inside to an open-concept layout filled with natural light and enhanced by an abundance of recessed lighting. The kitchen is a true centerpiece, featuring quartz countertops, a statement oversized island, stainless appliances, and an impressive amount of soft-close custom cabinetry--perfect for both everyday living and entertaining. The primary suite is a retreat of its own, showcasing a tiled walk-in shower with rain head, double vanities, and a spacious walk-in closet. Both interior baths are finished with double vanities, offering convenience and style throughout. But perhaps what truly sets this property apart is everything beyond the home: a 4,000 sq ft attached insulated shop with 16 ft ceilings, two pull-through, double-sided 14 ft garage doors (2-post car lift included), a 50x30 metal barn with electric and automatic waterer, new perimeter fencing already in place, and an incredible 2,400 feet of road frontage. All of this, located within the highly sought-after Burgin school district, known for its strong performance and tight-knit community feel--making it just as appealing for those prioritizing education as it is for those seeking land and lifestyle. This is more than a home--it's a lifestyle property that checks every box: land, luxury, functionality, and freedom, all in a location that's hard to beat. Opportunities like this don't come around often... and when they do, they don't last.

279 Dossett Ln, Harrodsburg

$1,599,000
6 Beds 3 Baths 26013760 MLS
Welcome to "The Bourbon Harrison Estate" This 48.5 Acre Working Farm & Historic Luxury Estate - Harrison & Bourbon County Line Discover the rare opportunity to own an exceptional working farm nestled along the scenic Harrison and Bourbon County line. Currently planted in soybeans and managed through a productive corn and soybean crop rotation, this fenced farm offers fertile ground, agricultural versatility, and outstanding investment potential. Surrounded by picturesque Kentucky countryside, the property provides a beautiful blend of open farmland, privacy, and breathtaking rural views. Whether you're seeking an active farming operation, equestrian property, private family retreat, or legacy investment, this remarkable acreage offers endless possibilities in one of Central Kentucky's most desirable rural settings. Complementing the farm is an extraordinary historic estate offering over 7,000 square feet of living space, where timeless elegance, modern comfort, and rich Kentucky history come together to create a truly one-of-a-kind property. This custom-built 6-bedroom, 3-bath residence showcases exceptional craftsmanship and thoughtful design throughout. Expansive windows flood the home with natural light while framing panoramic views of rolling farmland and the surrounding countryside. The dramatic two-story great room serves as the heart of the home, featuring soaring vaulted ceilings, an overlook balcony, a stunning floor-to-ceiling fireplace, and four glass doors opening to the wraparound porch, creating seamless indoor-outdoor living. A dedicated music room with exceptional acoustics and a whole-home sound system provides a unique space for entertaining, performances, or simply enjoying the ambiance of this remarkable estate. Designed for both everyday living and grand-scale entertaining, the chef-inspired kitchen features granite countertops, an expansive center island, spacious butler's pantry, and direct access to the formal dining room. The luxurious first-floor primary suite offers a private retreat complete with a clawfoot soaking tub, walk-in shower, private water closet with bidet, oversized walk-in closet, and spa-inspired finishes. The walk-out lower level provides exceptional flexibility for multi-generational living, guest accommodations, or a private in-law suite. Outdoors, resort-style amenities await, including a saltwater pool, hot tub, wraparound porch, and expansive outdoor living spaces designed to capture the beauty and tranquility of the surrounding landscape. Steeped in Kentucky history, this farm traces its origins to a land grant awarded following service in the French and Indian War, nearly three decades before Kentucky achieved statehood. Historic elements remain thoughtfully preserved, including a mantle crafted from the property's original log cabin and a historic grinding stone incorporated into the home's hearth. With productive farmland, established crops, an orchard, remarkable privacy, and a residence unlike any other, this extraordinary property offers the rare combination of agricultural opportunity, luxury living, and historical significance. More than a farm or a home, this is a Kentucky legacy estate destined to be treasured for generations. MUST Have an scheduled appointment- NO DRIVING ON THE PROPERTY- WALK THE ACREAGE- Soybean crop in place. Thank you for viewing this amazing property!

585 Ruddles Mill Cynthiana Rd, Cynthiana

$1,599,000
6 Beds 3 Baths 26013758 MLS
Welcome to "The Bourbon Harrison Estate" A Rare Legacy Estate Rich in History, Privacy, and Luxury Experience the perfect blend of timeless elegance, modern comfort, and historic significance in this extraordinary 6-bedroom, 3-bath residence offering over 7,000 square feet of living space. Ideally situated along the Harrison and Bourbon County line, this remarkable property provides unparalleled privacy, breathtaking rural surroundings, and a lifestyle that is truly one of a kind. Far from an ordinary farmhouse, this custom-built estate showcases exceptional craftsmanship and thoughtful design throughout. An abundance of natural light fills the home, especially on the main level, where expansive windows frame picturesque countryside views. The dramatic two-story great room serves as the centerpiece of the home, featuring soaring ceilings, an overlook balcony, and four glass doors that invite the outdoors in while providing seamless access to the wraparound porch. From this stunning vantage point, enjoy mesmerizing panoramic views of rolling farmland and Kentucky's scenic landscape. Adding to the home's unique character is a dedicated music room with exceptional acoustics, creating the perfect space for musicians, performances, gatherings, or simply enjoying the rich sound and ambiance of this remarkable setting with sound system throughout the home. Designed for both entertaining and everyday living, the chef-inspired kitchen is a true showpiece, featuring granite countertops, an expansive center island, a spacious butler's pantry, and convenient service access to the elegant formal dining room. The luxurious first-floor primary suite offers a private retreat complete with a clawfoot soaking tub, walk-in shower, private water closet with commode and bidet, oversized walk-in closet, and spa-inspired amenities designed for ultimate comfort and relaxation. The walk-out lower level provides exceptional flexibility and is perfectly suited for multi-generational living, guest accommodations, or a private in-law suite. Step outside and discover resort-style amenities designed to elevate everyday living, including a saltwater pool, hot tub, and expansive outdoor living spaces surrounded by peaceful countryside and unmatched privacy. Whether entertaining family and friends or enjoying a quiet evening under the stars, this outdoor oasis offers an extraordinary setting for creating lasting memories. Steeped in Kentucky history, the farm was originally commissioned to the prior family in recognition of their service during the French and Indian War, which concluded in 1763--nearly three decades before Kentucky achieved statehood. Historical elements remain thoughtfully preserved throughout the property, including a mantle crafted from the original one-room log cabin that once stood on the land and a historic grinding stone incorporated into the home's hearth. Today, this remarkable estate offers productive farmland, established crops, an orchard, and complete seclusion, creating a rare opportunity to own a significant piece of Kentucky history while enjoying the finest comforts of modern luxury. Rich in character, surrounded by natural beauty, and enhanced by exceptional amenities, this is far more than a home--it is a legacy estate destined to be treasured for generations.

585 Ruddles Mill Cynthiana Rd, Cynthiana

$1,595,000
3 Beds 3 Baths 26011538 MLS
NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester