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$14,000,000
7 Beds 3 Baths 1719199 MLS
A landmark Kentucky estate of extraordinary provenance, 10053 Shelbyville Road offers approximately 55 acres along one of the region's most coveted corridors near the Jefferson/Shelby County line. Built in the early 1800s, near the formation of the Commonwealth, the historic main residence is listed on the historic registry and is believed to be among the oldest homes in Kentucky, with the property recognized as one of the state's longest continuously farmed landholdings. The estate features a 5,336 sq. ft. main residence, an approximately 2,000 sq. ft. guest house, and expansive grounds suited for equestrian use, private farming, a family compound, or long-term legacy ownership. Rarely does a property combine this level of history, acreage, location, and future optionality. This is not simply a home — it is a generational Kentucky estate awaiting its next steward.

10053 Shelbyville Rd, Simpsonville

$5,500,000
7 Beds 6 Baths 26011667 MLS
Set on approximately 66 acres in Fayette County, Pelphrey Estate is a private luxury estate offering 9,769 square feet, 7 bedrooms, 6 full baths, extensive renovations, and exceptional versatility just minutes from Lexington. Originally inspired by West Coast Mediterranean architecture, the residence was designed with grand scale, soaring ceilings, detailed millwork, multiple fireplaces, and expansive views of the surrounding countryside. The layout offers a combination of formal and casual living spaces, private suites, office space, guest accommodations, and flexible living options throughout the home. The main level features a formal living room centered around a custom floor-to-ceiling fireplace constructed from coal with gas logs, an extensively renovated chef's kitchen, custom wet bar designed for entertaining, and a spacious den featuring a woodburning Buck Stove. The kitchen is truly the showpiece of the home where no detail was overlooked, featuring custom soft-close cabinetry, Calcutta Gold quartz countertops and full backsplash, oversized waterfall island, Wolf commercial range with double ovens, Sub-Zero side-by-side refrigerator, porcelain farmhouse sink, custom vent hood, premium fixtures, and designer finishes throughout. The main floor also includes two additional bedrooms and another renovated full bath. One of the home's two primary suites is located on the first floor and features a completely remodeled ensuite with double vanities, soaking tub, and custom tile walk-in shower. Upstairs, the show-stopping main primary suite offers an extraordinary amount of space with cedar-lined closets, vanity area, private sitting/flex space with fireplace, and a luxury ensuite featuring a soaking tub, 65-inch television, double vanities, quartz countertops, bidet toilet, and oversized custom tile walk-in shower with double shower heads. The upper level also includes two additional oversized bedrooms with renovated ensuite baths, another bedroom without an ensuite, laundry area, and a flex room ideal for office space or additional living area. Outdoor living spaces were extensively updated with a newly constructed fiberglass pool, stamped concrete entertaining areas, rebuilt stucco privacy walls, renovated pool house, landscaping improvements, upgraded drainage systems, and a custom gas fire pit overlooking the pool area. A 5-car garage offers four traditional garage bays, while the additional bay has been converted into a weight room. A convenient full bath located directly off the garage provides ideal access for pool guests. Additional improvements include five new heat pump systems, updated plumbing and electrical systems, new flooring throughout much of the home, fresh interior and exterior paint, custom iron entry doors, new lighting, insulation, and extensive mechanical updates. The property also includes a 5-stall barn, fenced acreage, a separate 3-bedroom, 2 full bath guest house with additional flex space, and 22 office spaces previously utilized for mortgage and title operations, creating unique opportunities for private estate living, business use, or multi-generational functionality. Formerly home to a 5/8-mile training track where successful racehorses trained, the farm carries a unique connection to Kentucky horse country. Pelphrey Estate offers a rare opportunity to own a renovated luxury estate with acreage, privacy, guest accommodations, extensive infrastructure, and exceptional flexibility in one of Fayette County's most desirable settings, conveniently located near the interstate, Hamburg conveniences, as well as Winchester.

8897 Rockwell Rd, Lexington

$5,439,000
4 Beds 2 Baths 1680398 MLS
Located just minutes away from Simpsonville and the Jefferson Co. line, this beautiful pristine farm offers all the amenities of country living along with the convenience of urban benefits. With almost 156 acres of rolling ground, there are limitless opportunities. The historic farm home features 4 BRs and 1.5 baths with almost all original hardwood flooring throughout. Spend the mornings and evenings on the covered porch enjoying the gorgeous views. Currently being used as a short term rental, this property has limitless possibilities. It also has two large ponds, along with over 2300' of frontage on Plum Creek. There are 3 platted five acre tracts included in the total acreage. An equipment barn built in 2018 is the perfect place to store your things. Don't miss this one!

4260 Fisherville Rd, Simpsonville

$4,995,000
3 Beds 2 Baths 1696824 MLS
This exceptional 287-acre farm presents a once-in-a-lifetime opportunity in Jefferson County. Comprised of three separate parcels, the property combines privacy, natural beauty, and convenience, with the Parklands just minutes away. The gently rolling topography features a blend of open fields and woodlands, offering the perfect setting for quiet country living, recreation, and/or multigenerational use. A large fishing lake plus a second small pond enhances the landscape, creating both beauty and outdoor enjoyment. Improvements include a well-maintained 3-bedroom stone house in good condition, a substantial outbuilding with 7,500 sq. feet, ideal for an event space or multi-use mechanical shop, and a third structurea three-car garage featuring a dramatic, light-filled loft with soaring wood beams, offering excellent potential for conversion into additional living space. With city water available on Old Heady Road, this property is as practical as it is unique. Whether envisioned as a private retreat, family compound, working farm, or recreational estate, this rare acreage offers unlimited possibilities.

6400 Old Heady Rd, Louisville

$4,500,000
8 Beds 8 Baths 1685040 MLS
This distinctive Bluegrass farm offers 82 acres of emerald green pastures located in the equine centric L'Esprit community in Oldham County. A tree lined drive leads to the impressive centerpiece of Meadowland Farm, a resplendent neoclassical residence with approximately 10840 square feet of elegant living space. Two shimmering ponds flank the main house which was designed with an emphasis on gracious entertaining. The main house includes a one bedroom ''apartment'', ideal for use for live-in help or as a home office which includes a full kitchen, bedroom, sitting room, and full bath. The equestrian compound was originally built by the LaCroix family, the world's premier Arabian breeder, and offers a pristine equine facility with 42 stalls, a huge indoor arena, an outdoor arena, an indoor walker, five paddocks, a large fenced pasture, and an equipment building. The farm adjoins the 25 mile bridal path that runs throughout L'Esprit as well as a boundary in scenic Harrods Creek. The property also includes a 3-bedroom, 2-full bath historic guest house. A prime location, Meadowland is only 35 miles from the Louisville airport, 65 miles from the Bluegrass airport and @70 miles from the Cincinnati airport.

1700 Park Shore Rd, La Grange

$4,450,000
7 Beds 13 Baths 26014529 MLS
Nestled on more than 35 acres, this extraordinary English-style estate offers timeless elegance and luxury on a grand scale. With over 18,000 sq. ft. of living space, the residence showcases classic architectural details, soaring ceilings, and expansive entertaining areas.The main home has seven spacious bedrooms including a luxury primary suite with custom closet, and private sitting room. The home's finishes reflect old-world craftsmanship blended with comfort. Formal living and dining rooms are complemented by inviting family spaces, a gourmet kitchen, and a library, all framed by sweeping views of the grounds. The property includes a beautifully designed pool house, perfect for summer entertaining, and a fully equipped workshop for hobbyists or collectors. Expansive lawns, mature landscaping, and wooded acreage create a serene setting, offering both privacy and natural beauty.

808 Oak Park Blvd, Calvert City

$4,300,000
4 Beds 4 Baths 1713555 MLS
Exceptional 443-acre farm in Spencer County offering a rare opportunity for development, investment, or a true legacy property. This stunning tract features a mix of open fields, rolling terrain, and breathtaking long-range views that make it ideal for a private estate, recreational use, or future subdivision potential. At the heart of the property sits a 2019-built home with 5 bedrooms and 3 full baths, designed for comfortable living while capturing the incredible surrounding landscape. Enjoy panoramic views from nearly every angle, with peaceful seclusion just a short drive from nearby amenities. Whether you're looking to build out a development, create a multi-generational retreat, or own a premier Kentucky farm, this property offers unmatched versatility, scale, and natural beauty.

2090 Mount Washington Rd, Taylorsville

$4,295,000
6 Beds 7 Baths 1721203 MLS
Twin Leaf | A Landmark Glenview Estate Inspired by Monticello Perched atop nearly seven acres of rolling Kentucky countryside in prestigious Glenview, Twin Leaf is a timeless masterpiece of design and craftsmanship—an extraordinary estate inspired by Thomas Jefferson's Monticello. Privately tucked behind a gated entrance, the approach to the home winds gracefully up the hill, offering a sense of anticipation that culminates in a striking arrival at one of Glenview's most distinguished properties. A formal central hall welcomes you into the heart of the home, elegantly flanked by gracious living and dining rooms—ideal for both refined entertaining and intimate gatherings. Every detail has been thoughtfully considered for comfort and function, from the chef's kitchen with top-tier appliances and butler's pantry, to the hearth-warmed eat-in space that invites daily connection. Bathed in natural light, dual sunrooms on either side of the home extend the living space and provide tranquil retreats throughout the day. At the core of the home, a grand central entertaining room flows into a handsome bar and richly appointed home office, both refined yet relaxed in tone. Just beyond, at the rear of the home, you'll find the true family room, a spacious, light-filled sanctuary designed for everyday living. With generous proportions, a cozy fireplace, and walls of French doors, this inviting space effortlessly connects to dual limestone terraces, the heated swimming pool, and a fully covered pool house. It's a seamless indoor-outdoor experience, perfect for both quiet evenings and lively gatherings. The pool house itself is a showpiece, crafted with imported cypress beams and a slate roof, and plumbed for a full outdoor kitchen and bath. Surrounded by lush landscaping and intentional design, the entire outdoor living area offers the feel of a private resort. Upstairs, dual staircases lead to the luxurious primary suite, a private haven featuring dual bathrooms, multiple walk-in closets, a fireplace, a sitting room, and access to a second-story terrace with sweeping views of the grounds. Three additional ensuite bedrooms complete the level, each with their own full bath and elegant appointments. The third floor has been artfully reimagined as a bunk room and media lounge, offering charm and flexibility for guests of all ages. The lower level continues to impress with a custom-designed, climate-controlled wine cellar for 2,200 bottles, a state-of-the-art exercise room with sauna and full bath, a private home theater, and an attached three-bay garage. Also on this level is a fully equipped guest apartment with its own kitchen, bedroom, and bathroom, ideal for extended family, guests, or live-in support, and offering walkout access to a secluded, sunken rose garden that feels like a hidden European courtyard. Twin Leaf is more than a home, it is a legacy estate, offering a rare blend of architectural significance, modern luxury, and natural beauty. Opportunities of this caliber are exceptionally rare in Glenview. For private showings and more information, please contact the listing agents.

3424 Glenview Ave, Glenview

$4,250,000
7 Beds 8 Baths 1721513 MLS
Nearing completion and ready for occupancy. Introducing an extraordinary opportunity to own a luxury masterpiece in the gated enclave of River Glades. This new construction by Black Label Builders seamlessly combines timeless elegance with modern innovation. Designed with the discerning homeowner in mind, this 7-bedroom estate spans an impressive 8,600 square feet and showcases an unparalleled level of craftsmanship. The grand main floor invites you into a world of sophistication, featuring expansive entertaining spaces, with its open floor layout and spacious kitchen. The primary suite offers a private retreat with spa-inspired finishes, while the thoughtfully designed main floor also includes an office, a prep kitchen, and a conveniently located laundry room. The home's upper level is equally captivating, with three spacious bedrooms, each boasting private en suite bathrooms. Above the attached 3-car garage, a versatile flex suite adds an additional bedroom and full bathroom, perfect for guests or extended family. The basement level elevates leisure with a sprawling family room, a custom bar area, and optional space for a golf simulator or fitness center. For car enthusiasts, the property includes a 3 car attached garage as well as a 3 car detached garage. With high-end finishes throughout and the rare opportunity for personal customization, this stunning property transforms luxury into a lifestyle. Seize the chance to create your dream home in one of the area's most coveted communities.

14401 River Glades Ln, Prospect

$4,250,000
6 Beds 8 Baths 1717523 MLS
Introducing 11306 Bodley Drive, a one-of-a-kind Blacketer Built masterpiece that boasts a grand 19,000+ square feet of pristine property with approximately 5 acres with some of the finest features imaginable. Upon arrival, you are greeted with a beautiful circular driveway and porte-cochere. As you step inside you are greeted with a stunning two-story foyer which design sets the tone for the rest of this home; opulent and glamorous with modern touches. Every inch of this home transcends luxury from the lavish marble flooring, accented with chocolate marble to the brilliant architectural details displayed by numerous arches throughout the home's interior, a rare feature among many Louisville homes. The gourmet kitchen is a true chef's dream featuring two warming drawers, Wolf gas and electric cooktops, a Miele dishwasher, and a wine and beverage cooler. There is also a separate banquet kitchen perfect for all of your entertaining needs. A stunning first-floor study offers gleaming hardwood floors, beautiful wainscoting, coffered ceilings, and custom built-in bookcases. This home features not one but two primary suites, one on the first floor and the other primary suite on the second floor, both including a luxurious en-suite bath. The second floor features a spacious theater room as well as three other bedrooms all offering an en-suite bath. Newly installed hardwood floors on the second floor. The spacious lower level with over 5,300 square feet features a place for a wine cellar and also includes the home's third kitchen. The luxurious brands continue throughout with the use of AirBoss® geothermal heating and Nest thermostats to heat and cool the home. The beauty of this home doesn't stop at the interior, it continues to the exterior with expansive balconies overlooking the limestone back patio and 4.85 acres of sprawling greenery and mature trees. Four car garage. This property is truly unlike any other in the Louisville area. Seller to give back $100,000 at closing for Buyer to add a pool.

11306 Bodley Dr, Louisville

$4,226,000
4 Beds 2 Baths 26017870 MLS
This 37-door residential portfolio of single family homes offers investors a rare opportunity to acquire a well-managed, geographically concentrated, and operationally efficient collection of assets across Paducah, KY. The portfolio combines stable in-place income with significant value-add potential, supported by strong management systems, long-term tenants, and below-market rents. Many properties are clustered within the same streets or blocks, minimizing management complexity and reducing operational costs. Professional Management in Place: Managed through the AppFolio Property Management System, providing comprehensive digital records, and transparent reporting. Each property has its own deed reference.

411 W Jefferson St Unit Parent property of 37 SF homes, Paducah

$4,195,000
6 Beds 9 Baths 1725941 MLS
Tucked within one of Louisville's most coveted enclaves, this extraordinary custom estate redefines luxury at scale—offering more than 13,000 square feet of meticulously crafted living space. From the moment you approach along the circular drive, the property reveals its stature. A grand foyer unfolds with sightlines that capture the home's remarkable millwork, sweeping archways, and intricate ceiling treatments. Every detail has been curated to impress—from artisan inlays to master-crafted woodwork that elevates each space with a sense of bespoke artistry. At the heart of the home lies a culinary haven designed for both function and unforgettable gatherings. With double-layered granite surfaces, custom off-white cabinetry, a warm hearth-side ambiance, and professional-grade appliances this kitchen is truly in a league of its own. The flowing layout connects seamlessly to a vaulted hearth room with a floor-to-ceiling creek-stone fireplace and an additional family room framed by coffered ceilings perfect for effortless entertaining. The primary suite is an ode to luxury living. Romantic arched ceilings, a fireplace-lit soaking tub, a spa-inspired steam shower, and dual boutique-style closets create a private world of indulgence. The bedroom itself features elegant tray ceilings with ambient shadow-box lighting, a fireside sitting area, and direct access to the resort-style pool terrace blurring the line between indoor comfort and outdoor serenity. A graceful staircase leads to three spacious bedroom suites, an airy loft, and a cozy sitting area. Ample unfinished space provides flexibility for storage or future customization. Created for hosting and leisure, the lower level is nothing short of spectacular. A state-of-the-art theater, expansive entertainment bar, and an immersive golf simulator room make it the ultimate retreat. A dedicated fitness room and two additional bedrooms with daylight windows add comfort and convenience for guests. The outdoor living experience rivals luxury vacation destinations. The gunite saltwater pool with waterfall, hot tub, and surrounding lounging terraces sets the tone. Beyond the pool, manicured putting greens and a full-scale, multi-sport court with three basketball goals offer tennis, volleyball, pickleball, and basketball perfect for both family fun and serious athletes. An outdoor pavilion featuring a fireplace, grill, and refrigerator connects directly to the kitchen, creating an effortless indoor-outdoor flow ideal for hosting at any scale. More than a magnificent residence, this estate delivers a lifestyle one that balances privacy, comfort, grandeur, and recreation. It is a rare opportunity to live within a personal resort crafted for unforgettable moments and everyday ease.

5705 Harrods Glen Dr, Prospect

$4,195,000
6 Beds 8 Baths 1701882 MLS
6 Wolf Pen Lane - Distinctive Luxury & Timeless Craftsmanship. Step inside a residence where artistry, design, and luxury meet. Every detail of this home has been thoughtfully curated with rare materials, custom finishes, and elegant features that make it one-of-a-kind. A rare opportunity to own one of Prospect's most distinguished estates. Set on over 18 acres of pristine grounds, this nearly 13,000-square-foot residence blends timeless European-inspired design with modern luxury, creating a home that is as breathtaking as it is functional. The grand foyer sets the tone with Italian marble floors and a hand-crafted mural inlaid with semi-precious stones. The living room soars with elegance, featuring a custom Austrian crystal chandelier, while the study is framed by two-story custom-built bookcases. Artistic details abound, from custom painted ceilings to the barrel ceiling with intricate artistry leading to the bedrooms. A granite back staircase and hand-forged iron railings showcase the unparalleled craftsmanship throughout. Every finish speaks of quality: marble fireplace surrounds, a backlit onyx feature wall in the family room, solid hardwood interior doors, and custom mahogany exterior doors. Modern comforts include Andersen windows, dual laundry rooms, and updated systems with a new pool pump, new appliances, and replaced HVAC units. The outdoor amenities elevate this estate to a private resort. Enjoy summer days by the sparkling pool with a waterfall, challenge friends on the tennis court, or take in the serene beauty of the 2-acre pond with fountains and a waterfall feature. For the equestrian, an eight-stable horse barn offers a rare luxury within such close proximity to the city. 6 Wolf Pen Lane is more than a home it's an estate designed for grand entertaining, quiet relaxation, and the finest in Kentucky living.

6 Wolf Pen Ln, Prospect

$3,995,000
13 Beds 12 Baths 26007272 MLS
Snug Hollow Farm & Retreat is a rare 290-acre contiguous estate nestled within the Red Lick Valley — a private Appalachian hollow just one hour from Lexington. At the heart of the property lies a thoughtfully designed B&B hospitality compound featuring six cabins totaling nearly 10,000 square feet of fully operational, furnished living space accommodating up to 50 guests nightly. Each cabin is supported by independent infrastructure, including private cisterns, UV-filtered water systems, individual septic systems, and natural gas service. The main farmhouse offers approximately 3,500 SF with two full kitchens, owner's quarters, and three additional rental spaces. The newest structure — a 2,500 SF dual-residence retreat center named Heart of the Holler, completed in 2025 — connects to over 800 SF of covered porches and anchors the property's growing group retreat capacity. What truly distinguishes Snug Hollow is its reputation. Celebrated in National Geographic Traveler and Southern Living and consistently top-rated by guests, the estate has cultivated a loyal following with a strong, proven record of hospitality income. The land itself is a masterpiece of biodiverse Appalachian terrain with newly improved access roads, over 4 miles of established trails winding through old-growth forest, wildflower meadows, and wildlife habitats. A spring-fed pond, onsite water systems, a handcrafted walking labyrinth, and an abundance of native flora and pollinators — including over 80 species of birds — elevate this estate into a true conservation asset and a place of genuine spiritual resonance for guests. The property has demonstrated helicopter accessibility, with guests having flown in and landed in the open field — presenting a natural opportunity for helipad development and an exceptional draw for high-end clientele. With no zoning restrictions and extensive infrastructure already in place, the property is equally suited for a private family compound, wedding destination, wellness retreat, boutique hospitality operation, or thoughtfully phased mixed-use development. Additionally all mineral rights convey and the property is Opportunity Zone fund eligible, making it eligible for investment through a Qualified Opportunity Fund. Protected by its scale, defined by its reputation, and enriched by its ecological and experiential depth, Snug Hollow Farm & Retreat is a once-in-a-generation opportunity to steward a truly irreplaceable piece of Kentucky landscape — where luxury is measured not in amenities alone, but in experience, privacy, and legacy. Sold completely furnished with immediate revenue in place.

790 Mcswain Branch Rd, Irvine

$3,995,000
4 Beds 7 Baths 1717465 MLS
Crowning Lot in Harrods Glen with Ohio River Valley Views and a Resort Pool Complex Set on 1.1 acres in Harrods Glen, this 11,436-square-foot French-inspired custom estate captures long views across the Harrods Creek and Ohio River valleys, with the Lewis and Clark Bridge visible on the horizon from the second-floor media room. The arrival is deliberate: a wide limestone walk, a covered entry, and double doors that open to a two-story foyer with travertine flooring and a curved staircase wrapped in wrought-iron balusters. The rear of the property backs to an HOA-owned tree preservation area, guaranteeing the view and the privacy for the long run. The double-island kitchen is built for serious cooking and large gatherings, with commercial-grade appliances including a Wolf range, a wine tower with refrigerated drawers, two walk-in pantries, and granite counters that flow into the family room and breakfast area. A first-floor library with fireplace and full wood paneling sits opposite a formal dining room with its own fireplace. Deep-profile moldings and raised panels carry through every room. The first-floor primary suite opens to a bath designed as two distinct sides, divided by the soaking tub and steam shower. Each side has its own water closet, extensive vanity, and built-in dresser drawers, with heated tile floors underfoot on winter mornings. Three additional bedrooms each have their own private bath. Laundry stations on all three levels. The lower entertainment level reads like a private club: theatre area with double-sided stone fireplace, billiard room, full-service bar with complete appliance package, dedicated wine room with tasting space, exercise room, secure collector's display room, full bath with terrace access, and cedar storage. Step outside and the backyard delivers what the front of the house promises. One expansive limestone terrace anchors the rear of the home, with a pool, stone waterfall edge, raised spa, and lounge area on one end, a stone gas fire pit ringed by lounge chairs at the other, and a covered pavilion in between featuring an outdoor kitchen, granite bar seating, TV, and tongue-and-groove cedar ceiling. Mature arborvitae frame the entire space for privacy. Elevator access to all three floors. Four-car rear-loading garage with epoxy floors and stairwell to the lower level. Three distributed audio-video systems, eight fireplaces, central vacuum, irrigation, security, and gas front-porch lights complete the package.

5706 Harrods Glen Dr, Prospect

$3,995,000
6 Beds 10 Baths 1710747 MLS
Finely crafted with every detail thoughtfully considered, this extraordinary custom estate in Harrods Glen was designed to accommodate both grand entertaining and seamless multigenerational living. A private elevator connects all three levels, while dual primary suites, one on the first floor and a fully appointed second on the upper level—offer flexibility without compromise. The two-story foyer opens to a soaring great room with coffered ceiling, gas fireplace, and walls of windows overlooking the manicured grounds. The gourmet kitchen pairs custom cabinetry, granite surfaces, premium appliances, a generous breakfast bar, walk-in pantry that doubles as a prep kitchen, and butler's pantry with wet bar—flowing effortlessly into a vaulted hearth room with stone fireplace and access to the outdoor living spaces. A richly paneled study with fireplace and bespoke built-ins provides a refined workspace. The main-level primary wing is a private retreat featuring a wet bar, adjoining office with fireplace and porch access, and a spa-caliber bath with dual vanities, jetted infinity soaking tub, expansive walk-in closet, and a dual-entry shower wrapped in handcrafted tilework. Upstairs, two additional en-suite bedrooms, including a suite with sitting area and fireplace, secondary laundry and kitchenette—offer ideal accommodation for extended family or long-term guests. Designed for unforgettable gatherings, the lower level showcases a statement bar with stone accents and arched columns, home theater, banquet dining room with wine cellar, billiards area, fitness studio with steam room, and a private guest suite. Among the home's most distinctive details: a 24-karat gold leaf moon ceiling crowning the dining room and multiple crystal chandeliers imported from Vienna, Austria—each mounted on motorized lifts for effortless maintenance. Outside, resort-inspired grounds unfold with a covered patio, full outdoor kitchen, and a swimming pool framed by mature landscaping, creating a setting equally suited for intimate evenings or large-scale celebrations. A six-car garage, multiple laundry areas, and layered architectural detailing throughout complete this exceptional offering—where craftsmanship, scale, and thoughtful design converge in one of Louisville's most established communities.

5610 Harrods Glen Dr, Louisville

$3,950,000
4 Beds 6 Baths 26012123 MLS
This expansive, private country farm property covers, 35.8 acres, divided into four distinct pastures of varying size. Property is well-suited for agricultural use, equestrian activities and rural living. Prime, secluded location, 11 miles from Lexington, 12 miles from Frankfort, 1.5 miles from Midway. Immediately adjacent to world-class thoroughbred foaling/boarding/breaking/training facility, Margaux Farm. The house has had a spectacular remodel done by Crawford Builders. It features a gourmet kitchen, with high-end appliances, open to the great room and 18 foot ceilings to complete the effect. The master suite is impeccable, including his and hers closets, fabulous bathroom, private sitting area, and exercise room. The home also features another first floor en suite bedroom. the two bedrooms upstairs are also en suite. There is a fabulous private Office, Butler's pantry, laundry room, covered porch, entertainment room and full bar with a game room. There are 15 deluxe stalls in 2 barns, hay storage, manager's house, run-in sheds, and gated and treelined driveway. Property entrance gate with advanced telephone entry and live streaming video. Whole house emergency generator fueled from underground propane storage. The house is completely integrated with remotely controlled audio/visual/heating control/security camera system!

595 Moores Mill Rd, Midway

$3,900,000
4 Beds 2 Baths 24015806 MLS
Campbells West Wind Farm presents a remarkable opportunity. This property encompasses 278 acres of prime land, offering unparalleled versatility with no zoning restrictions. Its strategic location along Highway US 150 enhances its appeal for various uses, including farmland, commercial, industrial, or residential. At the heart of the property lies a historic manor, built in 1901, which exudes timeless charm and character. While the home requires some repairs, it boasts an original 1700s kitchen, two exquisite wood staircases, and beautifully crafted woodwork. These highlight the manor's rich heritage. Property features a second home listed on the historical registry. The estate is further complemented by several outbuildings. The no zoning restrictions enhance the property's value, providing the flexibility to transform into a thriving commercial hub, an industrial complex, or a residential enclave. Campbells West Wind Farm is not just a property; it is a unique investment opportunity with immense potential. Its prime location, historical significance, and versatile land use options make it an exceptional buy for those looking to invest in a property with limitless possibilities

2888 Bardstown Rd, Springfield

$3,900,000
7 Beds 12 Baths 1714448 MLS
Some homes are built to live in. This one was built to host. Set behind mature landscaping on two private acres in coveted Mockingbird Gardens, this 17,000+ square-foot estate is a stage for the kind of evenings people talk about for years. The arrival sets the tone — a grand foyer opens into a great room that stops conversation: coffered ceilings, custom millwork, and a wall of windows framing the grounds beyond. The gourmet kitchen flows into two family gathering spaces and a dining room designed for long, lingering dinners. When the party moves downstairs, the lower level delivers: a true state-of-the-art theater, a full bar, an expansive entertaining lounge, and a temperature-controlled wine cellar that holds the collection you've been building. Step outside to a Jerusalem gold stone patio that wraps the rear of the home — built for cocktails at dusk, dinner parties under the stars, and Derby weekends that become legend. When the guests retire, the home rewards its owners just as generously. The primary wing is a private retreat with dual walk-in closets, a dedicated home office, separate ensuite baths, and its own laundry. Six additional bedrooms — each with an ensuite bath — give visiting family and guests the kind of privacy that turns weekends into traditions. An elevator connects all three levels. A home gym, screened-in second-floor porch, and secluded courtyard round out a property that delivers on every front. Recent investments — new roof, new gutters, fully refreshed landscaping — mean the next owner inherits an estate that's move-in ready and turnkey for entertaining. Mockingbird Gardens is one of Louisville's most established luxury enclaves, minutes from the city's best dining, the Highlands, and downtown. Homes of this scale, in this neighborhood, on two acres, simply don't come available. This isn't just a house. It's the address your invitations come from.

203 Waterleaf Way, Louisville

$3,850,000
4 Beds 3 Baths 26020901 MLS
A unique boutique farm in the heart of Lexington horse country, this beautifully renovated four bedroom home on 14 pristine acres is completely turn key and ready for you and your two legged and four legged family. Nestled among some of the most beautiful aged trees you will find in this area, including the one of the oldest Bur Oak trees, you will find equestrian paradise. Secluded among trees and opening into pastures you can see your horses in from all views, the quiet of farm life exists just minutes to all the necessities. The completely renovated home features 5800 square feet under air with flexible spaces for many options for staff and/or a home business. Key features include a whole house generator running off a 1000 gallon buried propane tank, separate staff apartment in the walk out basement with private entrance, new fencing in 2025 on entire property, 3 RV hookups at the barn and arena. The fully steel 125 x 250 covered arena features a 3' concrete ribbon wall and screen curtains throughout. Complete gutter system empties into a cistern for reusable water. Six stall barn features Lucas doors, rubber pavers and mat systems, tack room, feed room, and hot/cold wash rack and storage loft. No detail has gone unnoticed on this meticulously maintained exquisite equestrian estate. Just 15 min to downtown Lexington and Paris, Bluegrass Airport, and Keeneland, as well as two world class veterinary clinics and the Kentucky Horse Park.

2830 2830 Old Lemons Mill Rd Rd, Lexington

$3,800,000
5 Beds 5 Baths 26008955 MLS
Your dream Kentucky estate awaits. Wake up to panoramic views of rolling pastures, unwind by the pool as the sun sets over your land, and enjoy the privacy of a true countryside retreat. Situated on 10.49 fully fenced acres with classic limestone fencing, this property offers a picturesque setting just minutes from town. Featured in Kentucky Homes & Gardens, this 5-bedroom, 4 full bath, 1 half bath home blends Scandinavian-inspired design with warm, inviting finishes. Expansive floor-to-ceiling glass fills the home with natural light while capturing breathtaking views, complemented by automatic shades. Upon entry, a custom wood herringbone foyer is flanked by a private office and formal dining room. The main living area features a striking fireplace and dramatic wall of glass, flowing seamlessly into the chef's kitchen with an oversized island, built-in breakfast nook, and dual pantries. Additional main-level highlights include a custom bar with kegerator and beverage fridge, a spacious laundry room, and a half bath. Accordion glass doors lead to a screened porch, creating seamless indoor-outdoor living. The first-floor primary suite offers stunning views, a spa-like bath with power shades, and a custom walk-in closet. The second floor includes a built-in bunk room, dedicated movie room, additional flexible living spaces, two bedrooms, and a full bath. The third-floor guest retreat features a private bedroom, full bath, and viewing area. The finished lower level adds another bedroom, full bath, a second family room, and extensive storage—ideal for a home office, gym, or additional living space. Outdoor living is equally impressive with a screened-in porch, grilling area, and a fiberglass pool with automatic cover, lighting, pool bath, and storage. A fully fenced garden includes established blackberry, raspberry, strawberry, and asparagus beds. A spring-fed creek runs through the property, surrounded by black walnut trees and abundant wildlife, and the home backs to a scenic sheep farm for added privacy. Additional features include black brick exterior, Trex decking, geothermal system on the main level, multiple HVAC units with 5-zone app control, whole-home UV air and water purification, dehumidification system, radon mitigation, lightning rods, advanced drainage system, Ring security, and Starlink internet.

689 Sarah Blake Ln, Versailles

$3,499,900
6 Beds 7 Baths 1677651 MLS
Situated on 2.68 acres overlooking the Ohio River, this pre-civil war mansion offers over 9,000 sqft of living area, 3 stories plus walkout lower level, 3 car garage, and original character. The lot is full of large oak trees and the home offers stunning views from every window. Built in 1858, this 6 bedroom, 4 full baths and 3 half baths, 8 fireplaces home is sure to meet all your space needs. There is brand new plumbing, air conditioning, a new boiler system, updated bathrooms - nothing was spared during recent renovations. Rich in history with original door handles and hardwood floors, you will also find 12 ft ceilings on the main and upper floor, large windows overlooking the river in all outer rooms that allow natural lighting throughout every floor. Elevator serves the lower, main and second levels. Entryway stairs lead to all floors. First floor library sits off to the left of the entryway and connects to a large living area. This space has a beautiful fireplace and connects to a large sunroom. Butler's pantry sits in between the dining room and main kitchen with plenty of storage space. Kitchen leads to an upper deck porch with an outdoor fireplace overlooking stunning views of green landscape and the Ohio river. Mud room sits off the kitchen with a side entrance to the home. Second floor bathrooms have stunning marble floors and bedrooms are accompanied by fireplaces and large windows. Laundry is on the second floor along with a total of 4 bathrooms. Enjoy outdoor living with multiple balconies on the second floor with river views. Lower level living area has a stone fireplace and garage access. Exterior has been painted and the circle drive has been repaved. Black fencing rounds property. Slate roof.

8234 Sutherland farm Rd, Prospect

$3,490,000
4 Beds 4 Baths 26011023 MLS
Set on 112 exceptional acres in the heart of Central Kentucky's horse country, this elite equestrian estate offers a rare blend of luxury living, premier horse facilities, and timeless countryside beauty. The custom-built owner's residence was thoughtfully designed for both elegant entertaining and comfortable everyday living, featuring two first-floor primary suites, open-concept living spaces, a striking stone fireplace, and a private fourth bedroom suite upstairs complete with a charming widow's walk overlooking the farm. Separate guest quarters connected by a breezeway provide ideal accommodations for extended family, guests, or private office space while maintaining privacy and flexibility. The centerpiece of the equestrian improvements is a stunning European-style barn with an elegant courtyard design, offering 12 stalls, two hot and cold wash racks, a 16-foot center aisleway, two dedicated carriage spaces, two oversized tack rooms, feed and hay storage, equipment space, 1/2 bath, washer/dryer hookups, and rubber-matted stalls. The 12x12 stalls are enhanced with large exterior windows providing abundant natural light and ventilation. A secondary 11-bent tobacco barn includes two newly constructed stalls, ideal for overflow, quarantine, or flexible equine use. Additional residences include a well-appointed 3-bedroom, 2-bath manager's home overlooking the impressive 50m x 100m all-weather outdoor arena, as well as two additional homes perfectly suited for employees, guests, office use, or income-producing opportunities. A nicely maintained doublewide adjacent to the barn offers excellent potential for employee housing, short-term rental, or Airbnb use. Designed with both sport horse and thoroughbred operations in mind, the farm features five various sized fields, a round pen, cross country training, carriage driving hazards and obstacles, and a pond, all surrounded by rolling Kentucky scenery just 25 minutes from the Kentucky Horse Park. A truly versatile and beautifully executed equestrian property suitable for a variety of disciplines and lifestyles.

2027 Clintonville Rd, Paris

$3,400,000
5 Beds 5 Baths 1723395 MLS
Constructed circa 1861, the James Trigg House occupies nearly eight acres along Covered Bridge Road in Prospect, Kentucky. Listed on the National Register of Historic Places, the residence has been carefully maintained through successive ownership, preserving the architectural character and craftsmanship that define one of Jefferson County's most significant historic homes. The approach to the property begins beyond a gated entrance beneath a canopy of mature trees. The original Olmsted Brothers landscape design continues to shape the grounds, while an asphalt walking path circles the estate, providing access to nearly eight acres of lawns, gardens, and established trees. The front entrance opens to a central foyer with 11½-foot ceilings, original hardwood flooring, and architectural details that remain remarkably intact. Some original windows, doors, moldings, and nine of the home's ten original fireplaces remain in place, reflecting the level of preservation achieved throughout the residence. The formal dining room accommodates sixteen guests beneath its original 1861 gas chandelier, now converted to electricity. Decorative ceiling medallions, substantial crown molding, and two original fireplaces define the room. Adjacent, the formal living room is filled with natural light from oversized windows and glass doors and is anchored by two original marble and cast-iron fireplaces. Dual staircases, including one connecting the primary bedroom to the kitchen, illustrate the home's original design. Well-proportioned and sized rooms, handcrafted millwork, and period details remain consistent throughout the residence. The kitchen was renovated to complement the home's historic character while providing the finishes expected in a modern luxury residence. It includes a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, Scotsman ice maker, custom cabinetry, marble countertops and backsplash, farmhouse sinks, and a reclaimed barn wood island crafted by Bittners. An original brick wall remains exposed, connecting the space to the home's history. Adjacent to the kitchen, the sunroom overlooks the brick patio, fountain, and gardens, while the nearby den features a wood-burning insert within the original fireplace. The second floor includes four generously sized en-suite bedrooms, each with its own original fireplace, in addition to a fifth bedroom suitable as a nursery, study, or private sitting room. A second-floor laundry room provides everyday convenience. The wraparound porch has long served as an extension of the home's living space. Custom clear seasonal enclosure panels were designed specifically for the porch, allowing year-round enjoyment while preserving views across the property. These panels will remain with the residence. Substantial infrastructure improvements have been completed with preservation in mind. The home has been fully rewired, heating and cooling have been divided into four independently controlled zones, spray foam insulation has been added to the attic and kitchen walls. The copper roof with custom copper chimney caps protect the structure. The grounds offer both privacy and flexibility. A renovated heated saltwater gunite pool is surrounded by restored limestone and brick hardscape. A detached four-car garage includes a workshop and loft space suitable for future expansion, while a second detached one-car garage provides additional storage and utility. Mature gardens, expansive lawns, and multiple outdoor gathering areas support both large-scale entertaining and everyday living. The James Trigg House represents an uncommon opportunity to own a residence where historical integrity and modern livability exist together. Rather than recreating the past, each generation of ownership has chosen to preserve what makes the property significant while making careful improvements that allow it to continue serving as a distinguished private home.

7112 Covered Bridge Rd, Prospect

$3,400,000
6 Beds 7 Baths 25506210 MLS
A Timeless Castle Experience! Step into a masterpiece reminiscent of European chateaus with magnificent Gothic Revival and Renaissance influences. This exquisite brick and stone home, situated on 5 acres of land, is designed for those who appreciate artistry and elegance. The stunning 'Stone Serenity' room features a 24' tall turret, perfect for gatherings, complete with custom-built forged doors and intricate craftsmanship. The chef's kitchen boasts a double island with granite countertops and a unique pantry door, creating an ideal space for culinary adventures. Experience luxury in the primary suite, complete with a spacious walk-in closet and a spa-like bath featuring a walk-in shower, soaking tub, dual vanities, and direct patio access. Each guest bedroom offers its own private walk-in closet and full bath, ensuring comfort for all. The basement showcases stylish bourbon barrel decor leading to a vibrant game room and a stunning wine bar, perfect for entertaining. A home theater provides the ultimate movie experience. Additionally, a separate guest house offers versatility as a bedroom, office, or gym ideal for guests or a personal retreat. This property also includes a 1-acre wooded lot across the street from the house. Everything in this home reflects exquisite taste and style. Owner/Agent.

520 Cassity Way, Nicholasville

$3,395,000
6 Beds 7 Baths 1714692 MLS
Welcome to the iconic Sherley Mansion at 2106 Homewood Drive, a one-of-a-kind estate situated on 5 breathtaking acres in one of Anchorage's most desirable locations and within the renowned Anchorage School District. Known for its timeless elegance and thoughtful renovations, this historic property seamlessly blends classic architecture with modern luxury. The main residence features 5 spacious bedrooms, 4 full bathrooms, and 2 half baths, along with a 4-car garage and a stunning 2024 addition. The new wing includes a luxurious primary suite, spa-inspired bathroom, handsome home office, cozy sitting area, and a cutting-edge golf simulator—ideal for today's lifestyle. The lower level of the addition includes garage entry, a media/theater room, and a mudroom with built-in cubbies and organizational space. At the heart of the home lies a gourmet kitchen with an oversized island, stainless steel appliances, and a striking brick-encased stove, perfect for entertaining. Additionally, the scullery adjacent to the kitchen offers ample space for meal preparation and a sizable farmhouse sink. The home also offers a formal dining room, an inviting study, a grand living room, ornate staircases, and hardwood floors throughout. The estate's outdoor living is just as impressive. The 5-acre setting is beautifully landscaped and incredibly private, complete with a full-size tennis court and a custom tennis pavilion. The pavilion offers a living room, bathroom, and a versatile lower level that can function as a guest bedroom, yoga studio, home gym, or entertaining lounge. Combining historic charm with every modern amenity, 2106 Homewood Drive is a true Anchorage treasure perfectly suited for both refined living and unforgettable entertaining.

2106 Homewood Dr, Anchorage

$3,395,000
5 Beds 10 Baths 1690500 MLS
Welcome to elegance redefined at this beautiful estate nestled on over three verdant acres in prestigious River Glen. This exceptional property combines luxury living with practical comfort, all within the highly-regarded Oldham County School District while remaining just moments from the heart of Prospect. Step through the grand entrance foyer where soaring ceilings immediately captivate your attention. Beautiful paneled warm white walls complement the rich herringbone mahogany wood flooring, creating an atmosphere of refined elegance. The custom-built staircase, with its meticulous detailing, serves as both a functional element and an artistic statement that sets the tone for the sophisticated home. For those seeking a quiet retreat, the paneled study features a stunning fireplace with a carved stone mantleperfect for cozying up with a good book or tackling your work responsibilities from the comfort of home. (Who says you can't mix business with pleasure?) Special occasions deserve special spaces, and the formal dining room delivers with its own fireplace and direct access to a club-worthy butler's pantry that would make even professional entertainers green with envy. The living room offers serene views of the stone terrace and expansive green space beyond, connecting indoor comfort with outdoor tranquility. Culinary enthusiasts will rejoice in the gourmet kitchen, thoughtfully designed with beautiful custom cabinetry, an expansive island, and a cleverly hidden built-in pantry providing abundant storage. Top-of-the-line appliances stand ready for both everyday meal preparation and elaborate entertaining. This heart of the home opens seamlessly to the breakfast room, a great room that will seat the whole family, a mud room and an impressively large laundry room with storage galore. The first-floor primary bedroom suite offers a private sanctuary with breathtaking views and a spa-inspired bathroom featuring a rejuvenating steam shower and air-bubble soaking tubyour personal relaxation retreat after busy days. The walk-in closet is nothing short of magnificent in its proportions, easily accommodating the most extensive wardrobe collection. Upstairs, four additional bedrooms each boast their own full bathroom, providing privacy and comfort for family and guests alike. A second family room and additional laundry facility enhance the convenience of this level, while one bedroom stands out as the perfect in-law suite or as an alternative second floor primary suite. The finished lower level transforms into an entertainer's paradise, complete with a gym for fitness enthusiasts, a stylish family room with built-in wet bar and a marble fireplace plus another private room with a full bath attached. An extensive unfinished area provides valuable storage space for seasonal items and treasured possessions. Outdoor living shines with a gorgeous private flat backyard ideal for gatherings, games, and gardening adventures. The covered porch with a convenient half bath invites year-round enjoyment of the natural surroundings. A 3 car garage is perfect to have for cars and toys alike. This property presents a rare opportunity to own a custom, high-end home without the exorbitant construction costs, blending luxury, location, and value seamlessly. Don't miss your chance to make this extraordinary residence yours!

13905 River Glen Ln, Prospect