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$699,000
4 Beds ⋅ 4 Baths ⋅ 26018681 MLS
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!

716 Smith Martin Ln, Cynthiana
$209,000
3 Beds ⋅ 2 Baths ⋅ 26003251 MLS
Nice home located in Western Hills. 3 bedrooms, 2 full baths and unfinished basement. Enclosed sun-room and attached carport. Nice yard.

404 Broadway Ave, Cynthiana
$318,000
3 Beds ⋅ 2 Baths ⋅ 26014544 MLS
Charming, well-maintained, and full of possibilities, this all-brick 3-bedroom, 1.5-bath home sits on a spacious corner lot in one of Cynthiana's most desirable neighborhoods. Inside, you'll find beautiful original hardwood floors, an updated kitchen designed for gathering, and a versatile flex room that can serve as a home office, playroom, hobby space, or additional living area. The basement offers abundant storage and future potential, while the detached two-car garage provides even more space for vehicles, projects, or recreation. Step outside to one of the home's standout features—an incredible patio and beautifully landscaped yard that create the perfect setting for entertaining, relaxing, or enjoying quiet evenings outdoors. The large corner lot offers plenty of room for gardening, play, and everyday enjoyment, with ample parking for family and guests. Conveniently located near schools, parks, shopping, and dining, this home offers the best of in-town living while maintaining the feel of a quiet, established neighborhood. Buyer to verify square footage.

527 E Bridge St, Cynthiana
$660,000
4 Beds ⋅ 2 Baths ⋅ 26013167 MLS
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
$615,000
25507877 MLS
Discover a rare investment opportunity in the heart of historic downtown Cynthiana with 202 E Pike Street, a 16,524 sq ft, three-story commercial building offering unmatched versatility and nearly half a million dollars in improvements already completed. Fully restored where it counts and primed for redevelopment, this landmark property blends historic character with modern upgrades. Originally built in 1914, the building has hosted some of Cynthiana's most iconic businesses over the past century. Today, it features a turnkey business with new bathrooms, cabinetry, a bare commercial kitchen space, upgraded electrical, a 3-ton commercial HVAC unit, new water heater, and newly installed storefront windows on both Pike and Walnut Street. Major capital improvements from 2020-2025 include a new roof, extensive masonry work, full window replacements, leak remediation, structural repairs, and professional cleaning of the upper floors. Buyers will also receive blueprints, proof of all contracted work, vendor lists, and a washer/dryer in the basement. The top two floors offer extraordinary redevelopment potential. Whether envisioned as boutique hotel units, Airbnb suites, long-term apartments, or additional commercial spaces, the income possibilities are significant. With high demand for downtown lodging, excellent visibility, corner frontage (2 legal addresses with separate entrances), and extremely low inventory for comparable assets in Harrison County, 202 E Pike Street stands as a premier opportunity for investors, developers, or business owners seeking a transformative, income-producing property in a thriving Kentucky community. Selling the building only, not the business or any items owned or related to the business. Kitchen Equipment including the 3 compartment sink, commercial hood, commercial refrigerators & freezers including the walk in freezer does not convey with the property.

202 E Pike St, 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
$509,900
5 Beds ⋅ 2 Baths ⋅ 25500427 MLS
Beautifully restored 1900's victorian home bringing in old charm with all the benefits of being fully upgraded. Conveniently located in historic district just a few blocks from downtown amenities. 4114 +/-sq. ft, on 0.3 acres, 4-5 bedrooms, 2 full bathrooms. Home features its own private oasis with an outdoor tiki hut/bar, swim spa, and firepit all tucked away behind a privacy fence. Home is fully landscaped with a 2 car detached garage. Home features large rooms with tall ceilings, built-ins throughout, fireplaces and so much more. Back alley offers additional off street parking and access to garage. 1 year home warranty covered by sellers at closing. Pre-approval required for showings.

110 Clifton Rd, Cynthiana
$285,000
4 Beds ⋅ 2 Baths ⋅ 26014288 MLS
Welcome to 102 Oxley Avenue in Cynthiana—a charming, well-maintained ranch offering beautiful refinished hardwood floors, a flexible layout, and plenty of inviting spaces both inside and out. The main level features a spacious living room, cozy den, dining area, kitchen, three bedrooms, and a full bath. The partially finished walkout basement adds valuable living space with a fourth bedroom, an additional full bath, a fireplace, and direct access to the private backyard. Laundry hookups are available on either the main level or the lower level for added convenience. Outside, the versatile carport serves as covered parking or an ideal outdoor gathering space. Complete with a porch swing, it's the perfect spot to enjoy your morning coffee or relax at the end of the day. The quarter-acre lot offers attractive curb appeal and a peaceful, secluded backyard. Just minutes from historic downtown Cynthiana, local shopping, dining, and everyday conveniences, this home's prime location and adaptable floor plan make it an outstanding opportunity for a wide range of buyers. From first-time homeowners to growing families, downsizers, and investors exploring rental or short-term rental possibilities, this property checks a lot of boxes. With its blend of charm, functionality, and flexibility, the possibilities here are truly endless.

102 Oxley Ave, Cynthiana
$625,000
3 Beds ⋅ 4 Baths ⋅ 26014525 MLS
Welcome to 1205 Old Lair Road, Cynthiana, KY 41031, where peaceful country living meets modern comfort just minutes from town. This beautifully maintained brick home offers 2,252 square feet of thoughtfully designed living space featuring 3 bedrooms, 2.5 bathrooms, a formal living room, formal dining room, cozy den, and a dedicated home office. The spacious kitchen is a standout, offering abundant cabinetry, beautiful countertops, and plenty of workspace, while the oversized utility room adds everyday convenience. An attached two-car garage provides easy access to the home. Downstairs, the full walkout basement offers exceptional flexibility with a workshop, tornado room, half bath, and ample storage or future finishing potential. Designed for efficiency and peace of mind, the home is equipped with a geothermal heating and cooling system, whole-house water filtration system, water softener, and a 9-stage reverse osmosis UV drinking water system. Situated on over 8 acres, this property includes an additional buildable lot, creating endless possibilities for a future home, guest house, or investment opportunity. Enjoy the privacy and tranquility of country living while being less than five minutes from downtown Cynthiana, offering the perfect balance of space, convenience, and opportunity.

1205 Old Lair Unit lot 4, 5 &partial of 6, Cynthiana
$1,699,000
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