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418 Front St, Vanceburg
$199,000
6 Beds ⋅ 2 Baths ⋅ 25506549 MLS
Motivated sellers, Charming 1915 Victorian home with 2,800 sq ft, 6 bedrooms, 2 baths, and extensive updates. This home features a $106,000 renovation (2020) including roof and windows, updated kitchen cabinets, sink, faucets, and PEX plumbing. New 40-gal water heater (2025). Original character preserved with transom windows, 10" baseboards, and beautiful historic details.Three bedrooms on main level; three upstairs were recently remodeled with new insulation, walls, ceilings, doors, and flooring. Situated on a corner lot with a fully fenced yard and a large block building with garage and workshop. This classic Victorian combines beauty, history, and substantial upgrades—a rare find ready to welcome its next owners.

418 Front St, Vanceburg

514 Ann St, Frankfort
$525,000
10 Beds ⋅ 8 Baths ⋅ 26004803 MLS
Opportunities like this rarely come along. Built in the 1820s, this all-brick historic property sits in one of the most prime locations in all of Frankfort and is ready for its next chapter. The main house has already been mostly gutted, providing a blank canvas for the next owner to bring their vision to life while preserving incredible historic features that remain intact. Inside you'll find gorgeous original hardwood floors, massive pocket doors, and soaring 12-foot ceilings in several rooms—the kind of craftsmanship that simply can't be replicated today. This property offers tremendous flexibility and could easily be finished as a large single-family historic home with multiple bedrooms and bathrooms, or redesigned as a multi-unit investment property. It would also make an excellent short-term rental, live-work space, or even a boutique business location depending on the buyer's vision. Adding even more value is the guest house located in the backyard, which features four bedrooms and two bathrooms. This structure could remain a spacious guest residence, be used for short-term rentals, or easily be converted into two separate two-bedroom apartments, creating an additional income opportunity. For investors and developers, this project is an ideal candidate for historic restoration tax credits, which may allow 30-40% of qualified improvement costs to be returned as tax credits. That makes this not only an exciting restoration project but also a financially smart one. With its historic character, prime location, and endless possibilities, 514 Ann Street presents a rare opportunity to restore and reimagine one of Frankfort's historic properties. Whether you're looking to create a stunning family home, a unique investment property, or a standout short-term rental, this property offers the chance to bring a true piece of Frankfort history back to life.

514 Ann St, Frankfort

323 E Office St, Harrodsburg
$195,000
2 Beds ⋅ 2 Baths ⋅ 26014106 MLS
Welcome to 323 E Office Street in Harrodsburg, KY! Don't miss this adorable, recently remodeled 2-bedroom, 2 full bath home that is move-in ready and full of charm. Inside, you'll find a comfortable living room, kitchen with dining area, and a functional layout designed for everyday living. This home has seen numerous updates and improvements, including reinforced floor support with supplemental beams, updated flooring in both bathrooms, new gutters, upgraded thermostat, replaced smoke alarms, weather stripping, added mirrored medicine cabinets, storage cabinets, bar lighting, and more. The outdoor space is equally inviting with a privacy-fenced backyard, deck, storage shed, flower beds, raised planting beds, and attractive landscaping enhancements. Whether you're a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this well-maintained property offers comfort, convenience, and peace of mind. Conveniently located near downtown Harrodsburg, shopping, dining, and local amenities. Call today to schedule your private showing!

323 E Office St, Harrodsburg

312 E 4th St, Frankfort
$260,000
3 Beds ⋅ 3 Baths ⋅ 26015440 MLS
Priced to sell! This home has it all and is perfect for a Downtown Airbnb, Rental Property or First time home buyer! Step into the charm and character of downtown living with this beautifully preserved 3-bedroom, 2.5-bath historic cottage in the heart of Frankfort. Offering 1,512 square feet, this one-of-a-kind home blends timeless craftsmanship with thoughtful modern updates. Recognized with a Bluegrass Trust for Historic Preservation plaque, this home showcases rich historic details including original staircase rails, wood plank walls, and hand-troweled plaster that tell a story of its enduring character. Inside, you'll also find acid-stained and sealed concrete flooring, white-washed hardwood, and warm butcher block countertops that add style and functionality. The kitchen has been refreshed with all new appliances this year, making it move-in ready for today's buyer. Outside, enjoy a private fenced backyard complete with a storage shed—perfect for entertaining, gardening, or simply relaxing in your own secluded outdoor space. Located just moments from all that downtown Frankfort has to offer, this charming home is a rare opportunity to own a piece of history with modern comforts.

312 E 4th St, Frankfort

415 S, Lexington
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 26014172 MLS
Tucked into one of Lexington's most walkable blocks, this extraordinary loft-style residence began life as the historic Bluegrass Cigar Flats and was thoughtfully converted to residential use in mid 2000's. The result is a rare blend of urban character and refined design — a soaring open floor plan, original brickwork, reclaimed wood floors throughout, clever hidden doors, and custom built-ins, bookshelves, and storage at every turn. At its heart is a showstopping kitchen: polished concrete countertops, a Wolf gas range, dual dishwashers, Sub-Zero refrigeration, wine cooler, beverage refrigerator, and freezer drawers, anchored by an enormous butler's pantry. Spa-inspired marble baths feature Waterworks fixtures, and a generous family room invites you to gather and unwind. Currently styled as a private speakeasy for the seller's personal use, the home is ready to return to full-time residential living with purely cosmetic updates — a blank canvas with serious soul. Walk to the University of Kentucky, downtown restaurants, and shops, and enjoy a location that's convenient to absolutely everything. Loft living with this much history, craftsmanship, and location simply doesn't come along often. This one's a must-see.

415 S, Lexington

344 Madison Pl, Lexington
$799,000
5 Beds ⋅ 3 Baths ⋅ 26008570 MLS
Historic Charm Meets Modern Living in the Heart of Downtown Lexington! Welcome to the Hall Pettit Headley House—a rare opportunity to own a piece of Lexington history in one of the city's most sought-after locations. Situated directly across from the iconic Botherum property, this beautifully maintained home blends rich character with thoughtful updates throughout. From the intricate millwork in the formal dining room to the private wraparound porch and spacious deck, every detail invites relaxation and entertaining. The lush backyard offers a serene escape and hot tub, while inside, you'll find a chef-friendly kitchen with gas range and breakfast bar, two soaking tubs, two walk-in showers, and multiple fireplaces adding warmth and elegance to the living spaces. Enjoy city views and starry nights from the third-floor retreat, complete with skylights and a walk-in closet that also makes a great fifth bedroom. An unbeatable location within walking distance to the Central Bank Arena, local dining, and entertainment this home is truly a downtown gem. Charge your vehicle with the electric charger. Currently used as an airbnb!

344 Madison Pl, Lexington

314 E 16th St, Hopkinsville
$240,000
6 Beds ⋅ 3 Baths ⋅ 26013901 MLS
Step back in time and experience the elegance of this beautifully preserved 1880s historic home located at 314 E. 16th Street. Offering over 3,200 square feet of living space, this remarkable residence features 6 spacious bedrooms, 2.5 baths, and an abundance of original character that is difficult to find today. From soaring ceilings to nine decorative fireplaces, every room showcases the timeless craftsmanship and architectural charm of a bygone era. Thoughtful updates, including replacement windows, an updated kitchen and bathrooms, and a new roof and gutters installed in 2023, provide modern convenience while preserving the home's historic appeal. The spacious floor plan offers endless possibilities for entertaining, a growing family, or multi-generational living. Situated within walking distance of downtown shopping, local restaurants, and the entertainment district, you'll enjoy the perfect combination of historic charm and modern-day convenience. If you've been dreaming of owning a true piece of history with room to make it your own, this exceptional property is ready to welcome its next chapter. Sold-AS-IS, Where-IS.

314 E 16th St, Hopkinsville

132 Lincoln St, Nicholasville
$155,000
4 Beds ⋅ 2 Baths ⋅ 26015843 MLS
Looking for your next investment, renovation project, or dream home site? Situated on a generous 0.88 acre lot just two blocks from downtown Nicholasville and backs up to a city park, offering a rare combination of convenience, privacy, and potential. The existing house is ready for someone with vision—renovate and restore it, or start fresh and build the home you've always wanted. With its great location and generous lot size, the possibilities are endless. Investors may also wish to explore redevelopment opportunities. Check with the City of Nicholasville regarding potential rezoning options for multifamily or apartment development. Bring your ideas and make this exceptional property your next project! Call today for more information or to schedule a showing.

132 Lincoln St, Nicholasville