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216 S Chiles St, Harrodsburg
$139,000
26027483 MLS ⋅ 1,530 SqFt. ⋅ ACTIVE Status
Located in the heart of downtown Harrodsburg's Historic Morgan Row, 216 S Chiles Street offers a unique opportunity with flexibility for both business and residential use. With approximately 1,530 square feet, this fully updated property features a modern, open-concept front area filled with possibilities—ideal for an office, studio, reception area, or future residential living space. An additional room toward the rear provides even more versatility and could easily serve as a private office, workspace, storage area, or bedroom conversion. The renovated bathroom features updated plumbing, and with the addition of a shower, the property could transition easily into residential use. Recent updates include central air conditioning, gas heat, new flooring, all-new electrical service, and distinctive interior metal wall finishes that add both character and durability. The roof is approximately six years old. Double doors at the rear of the property open to a private patio area, providing convenient access that could also work well for business-related deliveries or drop-offs. Whether you're looking for a highly visible downtown location for your business, a flexible live/work opportunity, or a property you can convert into a unique residence, 216 S Chiles Street offers plenty of possibilities in one of Harrodsburg's historic downtown settings.

216 S Chiles St, Harrodsburg

2015 Old Main St, Maysville
$70,000
4 Beds ⋅ 2 Baths ⋅ 26027327 MLS ⋅ 3,520 SqFt. ⋅ ACTIVE Status
Big ideas belong here! In the heart of Historic Old Washington, this mixed-use property pairs private living quarters with expansive commercial spaces near gift shops, attractions, and the charming town square. The residential area features bright bedrooms with historic charm, an updated bathroom, and an outdoor shower nestled among bamboo- ideal for exploring live/work or short-term rental possibilities. Large open rooms, gorgeous hardwood floors, and multiple side entrances invite your vision for a shop, studio, gallery, gathering space, or other venture, subject to approvals. Work remains, but the character, space, and setting are ready for your next chapter. Let the virtual staging photos get your imagination going with all this could be. Bring your dreams to this incredible opportunity and see what you could create!

2015 Old Main St, Maysville

112 W Williamsburg St, Whitley City
$225,000
5 Beds ⋅ 2 Baths ⋅ 26027309 MLS ⋅ 2,830 SqFt. ⋅ ACTIVE Status
Welcome to 112 W. Williamsburg St., a spacious five-bedroom, one-and-a-half story home with 2,800 square feet of living space, just a short walk from local businesses and the business district. Hardwood floor, a durable metal roof, and a wheelchair ramp make this home both charming and accessible. Outside, the 0.6-acre lot has plenty of space to enjoy, with a fenced-in backyard, an above ground pool, and a small back deck for relaxing or entertaining. The unfinished walk-out basement is a blank canvas for extra living space, a game room, a workshop, or storage. A home warranty is included for added peace of mind. With this much space, a location this convenient, and so much potential, this one is ready for its next chapter. Buyer to confirm square footage

112 W Williamsburg St, Whitley City

217 S Main St, Nicholasville
$599,700
5 Beds ⋅ 5 Baths ⋅ 26026997 MLS ⋅ 4,600 SqFt. ⋅ ACTIVE Status
Completely Renovated 5BR/5BA Luxury Home — 4,600+ Sq Ft in the Heart of Nicholasville! Welcome to 217 South Main Street — a stunning luxury home offering over 4,600 square feet of beautifully renovated living space, right in the heart of Nicholasville, Kentucky. This 5-bedroom, 5-bathroom home has been completely transformed from top to bottom, delivering a true turnkey experience with high-end finishes throughout, including a convenient first floor primary bedroom. The kitchen shines with gorgeous quartz countertops and a stylish tile backsplash, while the bathrooms feature luxury tile finishes that elevate every detail. Refinished flooring flows throughout the home, bringing a fresh, polished feel to every room. Outside, you'll love the massive back deck — perfect for entertaining or simply relaxing — along with a newly fenced-in backyard offering privacy and space to enjoy the outdoors. With this much space, style, and quality craftsmanship, this home truly has it all. Don't miss your chance to own this one-of-a-kind luxury home in the heart of Nicholasville — schedule your showing today!

217 S Main St, Nicholasville

506-513 N Main St, Winchester
$249,900
26027255 MLS ⋅ 550 SqFt. ⋅ ACTIVE Status
UPDATE: ADDITIONAL PARCEL ADDED. Along with the description below, seller is including 513 N Main which has some buildings in need of repair (thus they were not added to the total square footage). Buy and repair the buildings, or demo the buildings and create additional parking. Has your small business officially outgrown the garage, basement, spare bedroom- or possibly all three? It might be time for a space of its own! This versatile property offers approximately 550 square feet of finished office space plus approximately 1100 square feet of shop/warehouse space. The office area gives you plenty of flexibility for a private office, reception/waiting area, additional workspace or storage, plus one restroom. Out back, the shop/warehouse is ready to work with a gas heater, new LED lighting and two 14' x 14' overhead doors with openers- perfect for vehicles, equipment, inventory or whatever your business needs to keep moving. Most of the work has already been done for you! You'll find fresh paint inside and out, new flooring throughout, and a brand-new blacktop parking lot. Convenient to I-64, Lexington and surrounding Central Kentucky communities, this could be a great fit for a contractor, service-based business or small business owner who simply needs more room to work, store, and grow. Because eventually, your kitchen table would probably like to go back to just being a kitchen table. Listing agent is related to seller.

506-513 N Main St, Winchester

106 W Vine St Unit 403, Lexington
$1,085,000
2 Beds ⋅ 2 Baths ⋅ 26027142 MLS ⋅ 1,452 SqFt. ⋅ ACTIVE Status
Experience luxury living at The Vine, downtown Lexington's newest boutique condominium designed for those who want more than just a place to live. With only one 2-bedroom residence currently move in ready, this sophisticated corner unit delivers a rare blend of style, comfort, and elevated luxury. Expansive windows flood the living spaces and bedrooms with natural light, while designer details that include, chef-worthy Sub-Zero and Wolf appliances, custom pantry, custom closets, designer wallpaper, window treatments, and private balcony add warmth and personality to the modern design. As an added plus, this unit is sold with 2 covered and designated parking spaces. Beyond your front door, The Vine HOA includes utilities for the condo as well as a social membership to The Vine Club offering resort-style amenities including the lounge, spa with cold plunge, sauna and hot tub, fine dining restaurant and the rooftop pool is almost complete. The Vine HOA concierge services includes a doorman, building security, plus a professional management group is already in place for short-term rental opportunities. Located steps from Rupp Arena, the University of Kentucky, restaurants, nightlife, and downtown entertainment, this is the kind of property that rarely becomes available. Luxury, convenience, and lifestyle all wrapped into one exceptional address.

106 W Vine St Unit 403, Lexington

1025 S 1st St, Louisville
$457,500
5 Beds ⋅ 4 Baths ⋅ 26026823 MLS ⋅ 2,975 SqFt. ⋅ ACTIVE Status
Beautifully maintained duplex in a convenient location close to downtown Louisville amenities! This charming property offers 2,975 sq ft with a 2BR/2BA downstairs unit and 3BR/2BA upstairs. The upstairs apartment is currently rented for $1,600/month, with the lease transferring to the new owner. An excellent opportunity to live downstairs while rental income helps offset the mortgage. Thoughtfully remodeled and cared for with exceptional pride of ownership. Beautifully Maintained Duplex with Exceptional Charm and Income Potential! A rare opportunity to own a thoughtfully remodeled and impeccably maintained duplex in a convenient Louisville location close to downtown amenities, dining, entertainment, shopping, and all the city has to offer. Offering **2,975 square feet** of finished living space, this charming property features a *2-bedroom, 2-bathroom downstairs apartment and a *3-bedroom, 2-bathroom upstairs apartment**, providing flexibility for an owner-occupant, investor, or multi-generational living arrangement. The upstairs unit is currently leased for *$1,600 per month*, with the existing lease transferring to the new owner, providing immediate rental income. Live comfortably in the downstairs unit while the rental income from the upstairs apartment helps offset your mortgage. Every detail of this home reflects exceptional care and pride of ownership. The property has been thoughtfully remodeled while maintaining its character and charm, resulting in a presentation that is truly above average. The 671-square-foot unfinished basement has been lined with spray foam insulation and protective coating, while the attic is also insulated and well lit—additional thoughtful improvements made by the owners to care for and protect the home. Outside, you'll find a backyard that feels like your own private oasis, beautifully landscaped with flowers and even butterflies making it their home. The upstairs unit offers a nice deck for relaxing or entertaining, while the downstairs unit enjoys its own patio area. There is also ample parking in the rear of the property, along with convenient on-street parking available in the front. Whether you're looking for an opportunity to live in one unit while generating rental income from the other, an investment property with an existing tenant, or simply a beautifully cared-for home with space and character, this property offers a unique combination of charm, functionality, and location. 1025 S 1st Street is truly a property that needs to be seen to be appreciated!

1025 S 1st St, Louisville

508 W Maple St Unit A-B, Nicholasville
$245,000
2 Beds ⋅ 2 Baths ⋅ 26026560 MLS ⋅ 2,232 SqFt. ⋅ ACTIVE Status
Great opportunity for investors! This duplex at 508 West Maple Street sits on a great lot with plenty of space and lots of potential. The property offers the opportunity to renovate and make it your own, with endless possibilities for someone looking to add value. A new roof was installed in 2025, and the windows were replaced in 2018. Whether you're an investor looking for your next project or someone looking for a property with room to grow, this one is worth taking a look at. Very large lot, tons of space, and so much potential! (Note: the seller also has 408 W Maple Street listed for sale. If you're interested in purchasing both properties, the seller would consider selling them together.)

508 W Maple St Unit A-B, Nicholasville

841 W Maxwell St, Lexington
$279,900
2 Beds ⋅ 3 Baths ⋅ 26026529 MLS ⋅ 1,296 SqFt. ⋅ ACTIVE Status
Downtown living at its finest! This beautiful, end-unit townhome with no HOA(!) couldn't be more conveniently located-- it's a stone's throw from Gatton Park, Rupp Arena, the Distillery District, and so much more. Updates in the last few weeks include fresh paint throughout, brand new plush carpet upstairs, and landscaping out front. New AC unit in 2021 and new roof in 2020, too. The first floor features a spacious living room with a bar area that passes through to the updated kitchen, where you'll find plenty of cabinet and countertop space as well as a sunlit eat-in dining area. A guest half bath completes the main level amenities. Upstairs, there are two large bedrooms, each with ensuite baths, and a separate laundry area in the hallway between them. This property has previously been used as a cash flowing Airbnb as well as a medium term rental. It would be perfect for students, smaller families, Wildcats fans looking for a gameday pad. city-dwellers wanting to be in the heart of it all, and investors looking to add to their portfolios. Schedule your private tour today!

841 W Maxwell St, Lexington

288 N 6th St, Williamsburg
$520,000
4 Beds ⋅ 3 Baths ⋅ 26026519 MLS ⋅ 3,292 SqFt. ⋅ ACTIVE Status
A rare opportunity in the heart of Williamsburg! Situated on approximately 15 acres, this unique property offers the perfect combination of a spacious family home, acreage, and outstanding future development potential—all within walking distance of the University of the Cumberlands. This is believed to be one of the last remaining tracts of this size this close to the University, making it an opportunity that is becoming increasingly difficult to find. The main residence offers an abundance of space with 4 bedrooms, the possibility of up to 6 bedrooms, 3 full baths, and an unfinished walk-out basement offering even more room to expand. With plenty of space inside and out, the home is well suited for a large or growing family. What truly sets this property apart is the potential beyond the main residence. Several cleared, build-ready sites are already in place throughout the acreage, creating possibilities for additional housing, apartments, or a residential subdivision, subject to applicable zoning and approvals. Live in the existing home while developing the remaining acreage, or explore the property's potential as a larger investment opportunity. With all city utilities available, much of the groundwork for future possibilities is already within reach. The property also offers access to the Cumberland River, adding another desirable feature to an already unique tract. Conveniently located near I-75 and positioned between Knoxville, TN and Lexington, KY, the property combines accessibility with a location just minutes from downtown Williamsburg and the University of the Cumberlands. Whether you're searching for a spacious home with acreage, an investment near the University, or land with future development potential, 288 N 6th Street offers possibilities that are hard to duplicate in this location.

288 N 6th St, Williamsburg

305 W Main St, Mt Sterling
$464,900
5 Beds ⋅ 4 Baths ⋅ 26026409 MLS ⋅ 4,586 SqFt. ⋅ ACTIVE Status
Stately, spacious, and filled with timeless character, this circa 1915 Colonial brick home is a true downtown Mt. Sterling treasure! Offering an impressive 5 bedrooms, 3 full baths and 1 half bath, this historic home provides an abundance of space both inside and out, all while being filled with beautiful natural light. From the moment you step into the grand and inviting entry foyer—the kind foyers dreams are made of—you'll immediately appreciate the craftsmanship and charm found throughout. The home features a spacious living room, den/study or home office, formal dining room, kitchen with breakfast nook and beautiful cabinetry and counter tops, mudroom, and two laundry areas. Original character shines through with beautiful hardwood flooring, crown molding, intricate door frames and trim work, built-ins, and several fireplaces that add warmth and personality throughout the home. The finished third level offers even more incredible living space with a huge recreation/family room plus an additional bonus room with skylights. This versatile space could even serve as another primary suite with its attached bathroom featuring a relaxing soaking tub. Outside, the home is situated on a generous .60-acre lot right in downtown Mt. Sterling and features a picture-perfect front porch worthy of the cover of a home and garden magazine, a rear patio perfect for entertaining, and a detached garage with additional storage space in the rear. The unfinished basement provides even more room for storage. Recent improvements include a new architectural shingle roof installed in August 2026, along with new guttering and downspouts. As a Mt. Sterling Historic Registered Home, this property offers the history, craftsmanship, space, and character that simply cannot be recreated today. If you've always dreamed of owning a LARGE historic home in the heart of downtown Mt. Sterling, this may be the one you've been waiting for. This remarkable property truly must be seen in person to fully appreciate everything it has to offer!

305 W Main St, Mt Sterling

514 N 7th St, Paducah
$379,900
4 Beds ⋅ 5 Baths ⋅ 26026251 MLS ⋅ 3,089 SqFt. ⋅ ACTIVE Status
Live and work in a funky four square perfectly positioned in Lower Town Arts District. Owned by Terra Cottage Studios since 2008, this two story building has been lovingly used as a working ceramics studio and hub for the successful Empty Bowls Project for decades. This home/business is full of eye popping & sentimental details like original glazed doorframes, four fireplaces (two with Paducah tile), exposed brick, original Mexican tiles, and a maple butcher block counter in the kitchen that came from an 1863 NYC bakery. The current owners researched insurance maps to discover Terra Cottage was originally built in 1888 as a fourplex. Since their purchase, they stabilized the foundation and turned the staircase 180 degrees to allow a commercial front entry and private upstairs dwelling entrance. The first floor is ready for your next commercial business with a waiting area, ADA bathroom, gallery/multi use rooms, and a kitchen with a 3-bay stainless sink. First floor kitchen is plumbed for gas & ice maker with a 220 outlet. The front of the first floor is sprinkled. Towards the rear of the first floor, you can have immediate supplemental income. There is a one-bedroom apartment ready for its next tenant with its own interior and rear entrance. The apartment has a cute kitchen with quirky tile, gas stove & fridge. The original wallpaper samples from the home are lovingly framed there. The apartment also has a large walk-in shower & the stackable washer and dryer is in its own utility closet. It most recently leased for $850/month long term and could bring more. The upstairs residence has a primary en suite with a custom Mexican tile bath surround & shower. There is also an 1883 beautiful marble pedestal sink in the dressing area. The 2 guest bedrooms are large with big closets and exposed brick. The upstairs doors were made in 1820 from French limousine oak & purchased in Saratoga. The upstairs eat-in kitchen has a gas oven, farmhouse sink, and large pantry with stackable washer dryer. Other cool features are the spice rack made from old film reels and custom skylights. Adjacent to the upstairs kitchen, is a large deck for grilling and entertaining. The detached 2 story rear building the owners refer to as "The Shed." It is framed out for a future art studio, airbnb or tiny home and has double pane windows and a garden shed. The backyard has custom tile & concrete raised gardening beds perfect for organizing your herbs and vegetables. Beyond the raised beds, there is room for four cars. The design has already been thought out for a garage off "The Shed" and alley. All of the electrical, plumbing & HVAC are new including commercial 3-phase grade. The interior was re-framed by adding 3.5 inch insulation & 5/8" sheetrock. The balcony tar roof is also new. Windows were all replaced with energy efficient double pane wood casement windows Front porch & balcony have had recent improvements too; vinyl ceilings, custom rail, stained concrete, electricity and fans added. There are two gas furnaces. Clean out for plumbing inside house on first floor.

514 N 7th St, Paducah

106 W Vine St Unit 809, Lexington
$995,000
2 Beds ⋅ 2 Baths ⋅ 26026170 MLS ⋅ 1,092 SqFt. ⋅ ACTIVE Status
Experience elevated downtown living at The Vine. This residence offers thoughtfully selected finishes, a distinctive tray ceiling, a private balcony overlooking the city, and a location near the top of the building. The unit includes two parking spaces and is the only residence with an electric vehicle charger at one of its designated spaces. Residents enjoy access to a rooftop pool, The Vine Club, concierge service with a doorman, and management services for short-term rentals. A social membership to The Vine Club is also included. With close proximity to Rupp Arena, the University of Kentucky, restaurants, nightlife, and other downtown Lexington amenities, this residence offers a sophisticated blend of convenience, comfort, and city living.

106 W Vine St Unit 809, Lexington

433 N College St, Harrodsburg
$225,000
3 Beds ⋅ 2 Baths ⋅ 26025943 MLS ⋅ 1,906 SqFt. ⋅ ACTIVE Status
CHARMING HISTORIC HOME IN HARRODSBURG'S NORTH COLLEGE STREET HISTORIC DISTRICT - Step back in time while enjoying the comforts of today with this charming older home located in Harrodsburg's desirable North College Street Historic District. Offering over 1,900 square feet of living space, this spacious home features 3 bedrooms, 1½ baths, a family room, den, eat-in kitchen, and an inviting enclosed front porch filled with windows—the perfect spot to relax and enjoy the changing seasons. Much of the home's original character remains, including mostly hardwood flooring and the warmth and charm found in older homes. The property is equipped with new central heat and air for year-round comfort. Situated on over ½ acre, the property provides plenty of outdoor space and includes a 2 car detached garage and a 24' x 24' detached garage/shop, offering excellent room for vehicles, hobbies, storage, or a workshop. Conveniently located just a short distance from downtown Harrodsburg, this property offers the opportunity to enjoy the character of a historic neighborhood while being close to local shops, restaurants, services, and community amenities. If you're looking for an older home with character, space, and a convenient location, this North College Street property deserves a closer look!

433 N College St, Harrodsburg

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