3551 MILLERSBURG RUDDLES MILL ROAD
ACTIVE
A rare offering in the heart of Bourbon County, this extraordinary 83-acre estate embodies the timeless beauty and rich agricultural heritage that defines the Kentucky countryside. Currently utilized as a productive crop farm, the gently rolling acreage presents endless possibilities for continued agricultural pursuits, an equestrian operation, or a premier cattle farm.
A picturesque driveway lined with magnificent October Glory maple trees creates a grand approach to the property, offering a breathtaking display of color each fall and setting the tone for the beauty and serenity that awaits. The custom-built residence, thoughtfully constructed in 1985, is perfectly positioned to capture sweeping views of the surrounding landscape. Offering five spacious bedrooms and three full bathrooms, the home was designed with both comfort and functionality in mind. A full unfinished basement, already plumbed for an additional bathroom, provides exceptional opportunity for expansion and customization.
One of the home's most captivating features is the stunning sunroom addition completed in 2023. Bathed in natural light and equipped with a mini-split system for year-round enjoyment, this inviting space offers a front-row seat to Kentucky's changing seasons—from misty spring mornings to golden autumn sunsets stretching across the farm.
Beyond the home lies an impressive collection of outbuildings that speak to the property's long-standing stewardship and versatility. An oversized four-bay garage/workshop is outfitted with electric throughout, plumbed with an air compressor system throughout, and one bay already prepared for a paint booth setup—ideal for hobbyists, collectors, or business ventures. Additional improvements include a large tobacco barn with attached stripping room, livestock barn, run-in shed with corn crib, original smokehouse and chicken house, and a mobile home well-suited for tenant housing or guest accommodations. Water is plentiful on the farm, featuring a natural spring that produces fresh water year-round and a beautifully maintained, stocked pond. An additional entrance off Redmon Lane offers convenient access and further enhances the property's functionality.
Properties of this stature seldom come to market. Whether your vision is to cultivate the land, establish an equestrian estate, raise livestock, or simply embrace the tranquility of country living, this remarkable Bourbon County farm offers an unparalleled opportunity to own a lasting Kentucky legacy.
Contact:
Mary Todd Ashbrook
Featured Listing
Residential
137 BLAKE LANE - BERRY

ACTIVE
$175,000
Welcome to 137 Blake Lane in Berry, Kentucky! This 3-bedroom, 1.5-bath home offers comfortable living with a practical floor plan that is perfect for first-time homebuyers, those looking to downsize, or anyone seeking a peaceful small-town setting. Inside, you'll find inviting living spaces with plenty of natural light and a functional layout designed for everyday living. Outside, enjoy a manageable yard with room to relax, garden, or entertain. Conveniently located in the heart of Berry, this home offers the quiet charm of country living while remaining within easy reach of surrounding communities. Whether you're searching for your next home or a great investment opportunity, 137 Blake Lane is ready to welcome its new owners.
Mary Todd Ashbrook
Contact:
82 WINDY RIDGE LANE

ACTIVE
$475,000
Escape to your own private slice of Harrison County with this exceptional 26± acre mini farm offering the perfect combination of privacy, functionality, and country living. Tucked away in a peaceful, secluded setting, this property is ideal for those seeking a rural lifestyle without sacrificing comfort and convenience. Conveniently located just 20 minutes from Georgetown, the property offers an excellent location for commuting to surrounding communities while still enjoying the serenity of country living. The well-maintained home features 2 bedrooms and 1.5 baths, providing a comfortable and inviting space to call home. Outside, the farm is thoughtfully designed and ready for livestock, horses, or hobby farming enthusiasts. The property boasts three fenced pastures with fencing in excellent condition, along with four automatic waterers, including one heated waterer for year-round use. The barn is equipped with four stalls and offers abundant space for animals, equipment storage, hay, or workshop needs. An additional 12x24 run-in shed provides even more shelter and functionality for your livestock operation. Whether you're looking for a turnkey horse property, a working mini farm, a recreational getaway, or simply a place to enjoy the peace and beauty of the countryside, this property delivers. With rolling acreage, scenic views, established farm infrastructure, and complete privacy, opportunities like this are becoming increasingly difficult to find. Come experience the tranquility, versatility, and endless potential this remarkable Harrison County farm has to offer. 20 minutes to Georgetown and wonderful location for commute to work in surrounding areas.
Mary Todd Ashbrook
Contact:
106 BATTLE GROVE AVENUE

ACTIVE
$199,000
Step back in time and fall in love with the character and charm of this delightful early 1900s home located at 106 Battle Grove Avenue. Situated on a large in-town lot just minutes from local schools and downtown, this 2-bedroom, 1.5-bath residence offers the perfect blend of timeless appeal and everyday convenience.
From the moment you arrive, the expansive covered front porch invites you to slow down, relax, and enjoy the charm of this established neighborhood. Inside, beautiful hardwood floors and classic architectural details create a warm and welcoming atmosphere throughout. The spacious first floor features a comfortable living room, formal dining room, eat-in kitchen, convenient half bath, and an additional office or flex space that can easily adapt to your needs.
Upstairs, you'll find two generously sized bedrooms, each boasting oversized walk-in closets—a rare find in homes of this era. The full bathroom offers both a tub and separate shower, providing functionality and comfort.
Step outside onto the back deck overlooking the spacious backyard, offering plenty of room for gardening, play, entertaining, or simply enjoying the outdoors.
Homes with this much charm, space, and such a desirable location don't come along often. Come experience all that this beautiful property has to offer!
Doug Hampton
Contact:
8100 US Highway 62 E

PENDING
$829,000
Tucked away at the end of a private drive, this exceptional 49± acre farm offers the perfect blend of privacy, comfort, and functionality. Surrounded by a beautiful mix of open pasture and wooded acreage, this property provides endless opportunities for farming, hunting, recreation, or simply enjoying the peaceful countryside.
The spacious 6-bedroom home is thoughtfully designed with a fantastic layout that is ideal for both everyday living and entertaining. Filled with an abundance of natural light, the home offers inviting living spaces, beautiful views of the surrounding landscape, and room for everyone to gather comfortably. With two bedrooms conveniently located on the main level, the floor plan offers flexibility to accommodate a variety of needs.
Outside, you'll find a metal barn ready for equipment, livestock, or workshop space, along with an older wood barn that adds character and additional utility to the farm. Wildlife is plentiful throughout the wooded acreage, while the pasture ground provides excellent space for livestock or agricultural use.
Properties offering this combination of acreage, privacy, a spacious home, and functional farm improvements are increasingly difficult to find. Conveniently located within an easy commute to Georgetown, Lexington, and surrounding communities, this is a rare opportunity to own a truly special piece of Kentucky countryside.
Mary Todd Ashbrook
Contact:
385 OLD PARIS PIKE

PRICE IMPROVEMENT
$499,000
Welcome to 385 Old Paris Pike in Cynthiana — an exceptional property offering one of the area's most desirable locations with a truly park-like setting. Situated on approximately 2 beautiful acres just outside the city limits, this property is surrounded by mature trees, peaceful scenery, and stunning views from every window. Step inside to find a spacious and inviting floor plan featuring a comfortable living room with beautiful built-ins, dining area, kitchen, breakfast nook, and an oversized family room perfect for gathering and entertaining. The main level also includes a convenient half bath and laundry area. Upstairs, you'll find 4 nicely sized bedrooms and 2 full baths, providing plenty of space for family or guests. Outside, enjoy summer days by the in-ground pool while taking in the tranquil surroundings. A unique bonus feature is the picturesque pond, partially owned by the property, adding even more charm and character to this rare offering. A beautiful blend of space, setting, and location that rarely becomes available.
Mary Todd Ashbrook
Contact:
742 COLBY ROAD

PRICE IMPROVEMENT
$510,000
Nestled in Northern Harrison County just 10 minutes from town, 742 Colby Road offers the perfect blend of peaceful country living and convenience. Situated on just over 10 beautiful acres, this well-maintained brick home features 3 bedrooms, 2 full baths, and a desirable split-bedroom floor plan. The spacious vaulted living room creates an open and inviting feel, while the full unfinished basement provides endless potential for additional living space, storage, or workshop area. Enjoy the quiet surroundings and scenic countryside views from every angle of the property. A standout feature is the impressive 30x60 shop complete with concrete floors and electric-perfect for hobbies, equipment, storage, or business use. Rarely do properties offering this much space, functionality, and setting come available.
Mary Todd Ashbrook
Contact:
242 WILSON AVENUE

ACTIVE
$319,000
Welcome to 242 Wilson Avenue, a charming three-bedroom, two-bath home just a few blocks from the heart of downtown Cynthiana. This home blends its original character with thoughtful updates, offering a welcoming layout perfect for everyday living or entertaining. Plus, you'll be just around the corner from Flat Run Park, giving you easy access to green space and outdoor activities. For the hobbyist or DIY enthusiast, the property also features a detached workshop—ideal for projects, storage, or creative endeavors. Come see how this lovely spot can be the perfect fit for your next chapter!
Mary Todd Ashbrook
Contact:
716 SMITH MARTIN LANE

ACTIVE
$699,000
Welcome to 716 Smith Martin Lane, where space, versatility, and location come together on just over two picturesque acres in the heart of Harrison County. Perfectly situated with convenient access to Cynthiana and surrounding communities, this exceptional property offers the peaceful feel of country living without sacrificing convenience.
Designed with flexibility in mind, this home is ideal for multigenerational living or those seeking room for extended family and guests. A private attached guest quarters features its own separate entrance, offering comfort, privacy, and independence while remaining connected to the main residence. The possibilities continue in the finished walkout basement, which is thoughtfully equipped as an additional living space complete with a full kitchen, spacious family room, bedroom, full bathroom, and a theater room—making it perfect for entertaining, or long-term guests.
Step outside and enjoy your own backyard retreat featuring a refreshing in-ground pool, a covered shelter perfect for outdoor gatherings, and a spacious yard surrounded by the beauty and tranquility of the Kentucky countryside. Whether you're hosting family celebrations, relaxing by the pool, or simply enjoying the peaceful setting, this property offers the lifestyle you've been searching for.
Opportunities like this are rare. If you've been searching for a home with a true mother-in-law suite, multiple living areas, or exceptional flexibility for today's evolving lifestyles, 716 Smith Martin Lane is a must-see!
Mary Todd Ashbrook
Contact:
112 WINDSONG WAY - Georgetown

ACTIVE
$399,000
Welcome to 112 Windsong Way in the desirable Homestead Subdivision! This beautifully maintained 3-bedroom, 2-bath home offers a highly sought-after split-bedroom floor plan designed for both comfort and privacy. The open-concept layout seamlessly connects the living room, kitchen, and dining area, creating the perfect space for everyday living and entertaining alike. The spacious primary suite is thoughtfully separated from the additional bedrooms, while the bright and inviting living spaces make you feel right at home from the moment you walk in.
Step outside to the screened-in back porch where you can relax, unwind, and enjoy peaceful views of the surrounding landscape without worrying about the bugs. Additional features include a 2-car attached garage, attractive curb appeal, and a great location.
Homes that are this well cared for and offer this combination of layout, outdoor living, and location don't come along often—schedule your showing today!
Mary Todd Ashbrook
Contact:
341 N. BROADWAY STREET - GEORGETOWN

ACTIVE
$315,000
Step back in time and experience the charm and character of this beautiful early 1900s home located at 341 North Broadway Street in Georgetown. Rich with history and timeless appeal, this property welcomes you with a classic wraparound front porch—the perfect spot to relax with a morning coffee or unwind in the evening while watching the world go by. Inside, you'll find the craftsmanship and details that make historic homes so special, including tall ceilings, stunning woodwork, and beautiful hardwood floors throughout much of the home. The spacious floor plan offers a wonderful blend of historic charm and modern convenience. The kitchen has been thoughtfully updated, along with a full bathroom and laundry on the main level, making the home move-in ready while preserving its character. Upstairs, you'll find four nice sized bedrooms and an additional full bath, providing plenty of space for family, guests, or a home office setup. Outside, enjoy the in-ground swimming pool, which has not yet been opened for the season but will be fully opened and ready for enjoyment prior to closing. Rarely do homes with this much character, space, and charm become available in such a desirable Georgetown location. As an added bonus, the property is being offered below appraised value, creating an exceptional opportunity for its next owner.
Mary Todd Ashbrook
Contact:
3828 KY HIGHWAY 36

CONTINGENT
$325,000
Just hitting the market! Welcome to 3828 Kentucky Highway 36 E. in Cynthiana — a well-kept 3 bedroom, 2 bath brick ranch situated on approximately 1.5 acres. This home offers a spacious and functional layout featuring a large living room with dining area that flows nicely into the kitchen. A flexible home office/bonus space provides great options for work, hobbies, or additional living needs. You'll love the bright sunroom overlooking the backyard along with the detached metal workshop for extra storage or projects. Additional highlights include a 2-car attached garage and a peaceful setting with room to enjoy the outdoors. The home has been well maintained and is in solid condition, while still offering the perfect opportunity for cosmetic updates to make it your own. Conveniently located just 5 minutes from town, this property offers the perfect blend of country space and everyday convenience — a wonderful place to call home!
Mary Todd Ashbrook
Contact:
+1-859-588-1520
907 CARL STEVENS ROAD

PENDING
$350,000
Welcome to 907 Carl Stevens Road, a wonderful split-level brick home offering the perfect blend of space, privacy, and convenience. Situated on just shy of two acres and tucked back off the road, this property features a long blacktop driveway, beautiful yard space, and a peaceful setting just minutes from town. Inside, you'll love the open-concept living, kitchen, and dining area that creates a warm and inviting space for everyday living and entertaining. The upper level includes three spacious bedrooms and two full baths, including a comfortable primary suite. The lower level offers a fourth bedroom, half bath, and a versatile flex space ideal for a rec room, home office, workout area, or additional living space to fit your family's needs. Outdoor amenities truly set this property apart. Enjoy warm summer days relaxing by the above ground pool with a spacious surrounding deck perfect for lounging and entertaining. The fenced backyard provides additional space for pets or play, while the impressive 40x80 metal shop offers endless possibilities for storage, hobbies, equipment, or workspace. This property offers the room, functionality, and peaceful setting you've been searching for.
Mary Todd Ashbrook
Contact:
115 GRANDVIEW DRIVE

ACTIVE
$375,000
Welcome to 115 Grandview Drive — being offered for the first time in over 60 years! Located in the highly desirable Grandview Subdivision, this lovingly cared for mid-century modern home offers timeless character, generous space, and a wonderful flowing layout throughout. Step inside through the welcoming foyer, where you'll find formal living and dining rooms that create an inviting first impression and ideal entertaining spaces. The rear den is filled with natural light thanks to large sliding glass doors overlooking the beautiful backyard and patio area. The kitchen offers a cozy dining area and functional layout ready for everyday living. This spacious home features 3 bedrooms and 2.5 baths, along with a full basement offering endless possibilities for entertaining, recreation space, storage, or even additional bedrooms if desired. Outside, enjoy the level backyard and patio area complete with a gas-wired grill setup, perfect for gatherings and relaxing evenings. Additional highlights include a 2-car attached garage with extra storage space and the peace of mind of a Generac generator system. A rare opportunity to own a cherished home in one of the area's most established neighborhoods in Cynthiana.
Mary Todd Ashbrook
Contact:
300 KELLER WAITS LANE

PRICE IMPROVEMENT
$625,000
Welcome to 300 Keller Waits Lane - the ultimate live, work, and play property, just 5 minutes from town! Nestled on 20± picturesque acres, this one-of-a-kind property offers two homes, two ponds, and unmatched versatility. The main home is bursting with character inside and out, exuding warm country rustic charm. Designed for those who value their workshop space as much as their living space, the home offers as much garage and workshop area as it does house.
A massive front bay—originally built for RV storage—features tall ceilings, split units for climate control, and endless potential for your projects, hobbies, or storage needs. Inside, the main level includes a cozy open-concept kitchen/living space, a spacious den/rec room, and a bedroom with full bath. Upstairs, you'll find an additional bedroom, full bath, and a separate living area—ideal for guests or a private retreat.
Also included is a charming 800+ SF guest cabin with 2 bedrooms and 1 bath—perfect for extended family or visitors. The property also boasts a 30x42 detached workshop with electric and a lean-to, offering even more space to create, build, or store. This scenic setting, complete with rolling hills, two serene ponds, and privacy all around, is truly a rare find. Don't miss your chance to own this slice of Kentucky paradise!
Mary Todd Ashbrook
Contact:
Farms
82 WINDY RIDGE LANE
ACTIVE

$450,000
Escape to your own private slice of Harrison County with this exceptional 26± acre mini farm offering the perfect combination of privacy, functionality, and country living. Tucked away in a peaceful, secluded setting, this property is ideal for those seeking a rural lifestyle without sacrificing comfort and convenience. Conveniently located just 20 minutes from Georgetown, the property offers an excellent location for commuting to surrounding communities while still enjoying the serenity of country living. The well-maintained home features 2 bedrooms and 1.5 baths, providing a comfortable and inviting space to call home. Outside, the farm is thoughtfully designed and ready for livestock, horses, or hobby farming enthusiasts. The property boasts three fenced pastures with fencing in excellent condition, along with four automatic waterers, including one heated waterer for year-round use. The barn is equipped with four stalls and offers abundant space for animals, equipment storage, hay, or workshop needs. An additional 12x24 run-in shed provides even more shelter and functionality for your livestock operation. Whether you're looking for a turnkey horse property, a working mini farm, a recreational getaway, or simply a place to enjoy the peace and beauty of the countryside, this property delivers. With rolling acreage, scenic views, established farm infrastructure, and complete privacy, opportunities like this are becoming increasingly difficult to find. Come experience the tranquility, versatility, and endless potential this remarkable Harrison County farm has to offer. 20 minutes to Georgetown and wonderful location for commute to work in surrounding areas.
Contact:
Doug Hampton
Lots
27 WALNUT HILL COURT
ACTIVE

$45,000
Build the home you've always envisioned on this beautiful 1.38-acre lot in the desirable Desha Point Subdivision. This spacious homesite is ready for construction and offers a peaceful setting with picturesque views overlooking a nearby pond, creating a beautiful backdrop for your future home. Conveniently located just five minutes from downtown Cynthiana, you'll enjoy the perfect combination of privacy and accessibility with shopping, dining, schools, and everyday conveniences just minutes away. If you've been searching for the ideal place to build, this exceptional lot is ready to make your dream a reality.
Contact:
Mary Todd Ashbrook
1514 RUSSELL CAVE ROAD
ACTIVE

$375,000
Rare opportunity to own a truly unique 16-acre property on Russell Cave Road in Bourbon County, formerly utilized as a rock quarry and now offering incredible potential. Located less than 30 minutes from both Lexington and Georgetown, this property combines privacy with convenience in the heart of the Bluegrass. The land features a stunning small pond, picturesque surroundings, and multiple prime building sites—ideal for creating your dream home or private retreat. Enjoy the peace and seclusion of country living with no neighbors in sight, while still being within easy reach of nearby amenities. Zoned for agricultural or residential use, this versatile property offers endless possibilities for those seeking space, beauty, and opportunity.
Contact:
Doug Hampton
Commercial
201 E. PIKE STREET

ACTIVE
$469,900
Located in the heart of downtown Cynthiana, 201 East Pike Street is a beautifully restored mixed-use building positioned on the highly visible corner of Pike and Walnut, offering exceptional exposure in a thriving business district. This turnkey investment opportunity features a fully occupied property with strong, consistent income from day one. The ground level is leased to a successful, established bookstore, providing a stable commercial anchor. The upper level includes four fully rented residential units, consisting of three efficiency apartments and one one-bedroom apartment, offering a well-balanced rental mix. The building underwent a complete renovation in 2019, blending historic charm with modern updates, ensuring low maintenance and long-term appeal. With its prime location, strong tenant occupancy, and immediate cash flow, this property presents an outstanding opportunity for investors seeking a high-performing asset in a growing downtown market.























