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$310,000
4 Beds 2 Baths 26024335 MLS
Built of brick and stone in 1931, this traditional home offers the charm of another era with the space and features today's buyers want. Arched doorways and windows, tongue-and-groove ceilings and walls, and gorgeous fireplaces in both the living room and den give this home a personality all its own. The first floor features a cozy breakfast nook, a window-filled back den, and a convenient bedroom. Upstairs, you'll find three additional spacious bedrooms. Altogether, the home offers four bedrooms, one-and-a-half bathrooms, a partially finished basement, and a new HVAC system to boot! Although it's located right in the city, the large corner lot offers many of the features buyers love about country living—a wood privacy fence, mature trees, covered porches, a new above-ground pool with a deck, a detached garage, and off-street parking. Timeless construction, unforgettable character, and an outdoor space made for enjoying—this is one you'll want to see in person!

525 E Pike St, Cynthiana

$649,000
3 Beds 2 Baths 26023266 MLS
Beautifully maintained one-owner home on 20 +/- acres. You will notice how picturesque this property is as soon as you enter the driveway and see the manicured paddocks and the stocked pond with a fountain. The freshly painted cedar siding home has a covered front porch and beautiful landscaping. Inside, there is a foyer that enters into the large family room with a propane fireplace. The kitchen has all appliances and a moveable island. The dining area has so many windows to overlook the farmland. The homeowners transformed the garage into additional living space that is perfect for a den and family gatherings. The split bedroom floor plan has a primary bedroom with his-and-her closets and an attached ensuite. There are 2 additional bedrooms, both generously sized with double closets. There is a second full bath. Outside, there is a large carport and patio, perfect for relaxing and family time. All of this on the prettiest parcels of land you have seen. Several outbuildings include sheds and barns. One barn has electric and water, and the biggest one has electric. This property would be perfect for horses or other livestock. These sellers built this home and have cherished it for many years. They had a new geothermal unit installed 2 years ago. Homes like this do not come on the market often; don't miss your chance. Located only 15 minutes from Toyota. Schedule your appointment today.

2846 Ky Highway 1842 N, Cynthiana

$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!

3495 Ky-32, Cynthiana

$297,500
4 Beds 2 Baths 26022511 MLS
Welcome home! This beautifully renovated 4-bedroom, 2-bathroom home is move-in ready and waiting for its new owners! Completely updated throughout, this home offers a fresh, modern feel while maintaining the comfort and functionality you've been looking for. The spacious kitchen is sure to impress, featuring beautiful cabinetry, granite countertops, a tile backsplash, a large center island, and all-new appliances. Major updates include a brand-new HVAC system and hot water heater, providing peace of mind and added value for years to come. The home also features a full basement, offering plenty of additional space for storage, a workshop, recreation, or whatever best suits your needs. Step outside to enjoy the fully fenced-in backyard, with plenty of room to play, entertain, gather with friends, or simply relax. With extensive renovations, modern updates, and plenty of space both inside and out, this home is ready for you to move in and make it your own!

102 Cardinal Ct, Cynthiana

$339,000
3 Beds 1 Baths 26020788 MLS
Welcome to peaceful country living! This well-maintained 3-bedroom, 1-bath brick home offers timeless appeal and endless potential. Inside, you'll find a comfortable layout with an unfinished basement, providing ample storage or the opportunity to create additional living space. Situated on approximately 7 beautiful acres, this property is perfect for those seeking room to roam, garden, or enjoy the outdoors. A detached 2-car metal garage offers plenty of space for vehicles, equipment, or a workshop, while the barn adds even more versatility for hobby farming or extra storage. The attached carport provides convenient covered parking. Whether you're looking for a peaceful country retreat, a small farm, or simply more space to enjoy, this property offers the best of rural living with the convenience of being located in the lovely town of Cynthiana. Don't miss this opportunity to make this scenic property your own!

6092 Ky-36, Cynthiana

$579,900
13 Beds 26019807 MLS
Looking for off-the-grid privacy? Hoping to start your own serene homestead in the country? Searching for a piece of Bluegrass with two separate homes? This nearly 21-acre working farm in Harrison County boasts a 5-stall horse barn with a tack room, a 40x30' versatile metal workshop/barn with a run-in shed, a 60x32' pole barn, an expansive greenhouse, a pond, and multiple paddocks. Situated at the end of a private drive, this property is less than 10 minutes from downtown Cynthiana and just minutes from the Harrison, Bourbon, and Nicholas County lines. Each 2-story home is over 2900+ SQ FT with oversized living areas and kitchens, stunning hardwood flooring, and basements. One house was built in 2019 and the other was built in 2024. With 13 bedrooms between the two homes there's a great opportunity for multiple-family living or rental income. Imagine watching the sun rise as you sip coffee on your deck or tossing in a line to fish in your own pond. There's no shortage of space for your animals, recreation, and hobbies. Utilize the 48x36' greenhouse to enjoy homegrown produce year round. This farm is full of fruit trees and bushes including: apples, peaches, cherries, blackberries, and mulberries. You truly need to see this gem of a property for yourself to take in all it has to offer.

5183 Ky-36, Cynthiana

$649,900
4 Beds 2 Baths 26013167 MLS
Motivated Sellers!! Charming Craftsman Home on 12 Fenced Acres! Step back in time and experience the character and craftsmanship of this beautiful 1938 brick Craftsman home situated on 12 fenced acres. This spacious home offers 4 bedrooms, 1.5 bathrooms, hardwood flooring with some tile, a kitchen with a cozy breakfast nook, formal dining room, living room, home office, laundry room, and an enclosed back porch currently used as a sunroom. You'll also appreciate the large closets, full unfinished basement, and attic space, providing plenty of storage and endless possibilities. Outside, the property is equally impressive with three fenced fields, paddocks with automatic waterers, a barn complete with tack room, a pond, above-ground pool w/deck, and a detached two-car garage. Whether you're looking for an equestrian property, hobby farm, or peaceful country retreat, this property offers the perfect combination of historic charm, functionality, and room to enjoy the outdoors. A rare opportunity to own a piece of the countryside while enjoying the timeless beauty of a classic Craftsman home.

2722 New Lair Rd, Cynthiana

$925,000
5 Beds 3 Baths 26011909 MLS
Amust see to believe. This Blue Grass Trust historical home on 27 acreshas been meticulously maintained and is in excellent condition. Built in 1822 and at that time called the John William Kimbrough House, this beautiful estate was later named Popular Hall Farm. Exquisitely restored while preserving its history. It boasts 14ft ceilings, oringinal hardwood floors, muiltiple working gas fireplaces, elegant chandeliers and abundant closets. A completely customized kitchen with large island, 6 burner gas range, Subzero refrigerate,granite,and stainless steel countertops make this kitchen a chef's dream. Beautiful foyer. spacious dining room,living room and library with floor to ceiling bookshelves. Three tastefully renovated modern bathrooms accompany five bedrooms. Outstanding natural lighting throughout the housefrom grand windows afford breathtaking views. New gas and water lines to the road was installed in spring 2025. Attention to detail is the hallmark of Poplar Hall Farm as the buyer will notice at the first visit. it is also within walking distance to retaurants and shopping in downtown Cynthiana.

231 Kentucky 36, Cynthiana

$499,000
3 Beds 2 Baths 26010452 MLS
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.

742 Colby 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

$375,000
3 Beds 3 Baths 26011111 MLS
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.

115 Grandview Dr, Cynthiana