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$514,900
26022757 MLS
Historic Charm meets endless possibilities! Step into a truly unique piece of Danville history with this stunning late-1800's home located in the heart of historic downtown Danville. Rich with character and timeless charm , this distinctive property has enjoyed a fascinating past, serving over the years as professional office space, two different restaurant establishments, and currently serves as a charming gift shop and home interiors business. The possibilities for its next chapter are just as exciting! The flexible layout offers opportunity to continue a commercial venture on the first floor while creating very comfortable living quarters on the second floor with a few tweaks. Ideally setup for a designer, entrepreneur, professional office space, restaurant, or anyone dreaming of combining home and business under one historic roof! With its downtown location, character-filled architecture, and remarkable history of adapting to different uses, this property is way more than a commercial space--it's an opportunity to become part of Danville's story while creating something that is uniquely your own. Live upstairs. Work downstairs. Own a piece of Danville history. The possibilities are endless!

219 S 4th St, Danville

$350,000
26022246 MLS
Investor Opportunity: Downtown Mixed-Use with Active STR Cash Flow + Clear Upside Exceptional value at $350,000 for this high-visibility mixed-use property at 110 W Kentucky Ave in the heart of Pineville's town square on HWY 25E. Approximately 5,943-6,250 SF total. The upper level operates as the established Boone Trace Inn short-term rental with 7 private bedrooms (coded entry), gathering room, fully equipped kitchen, dining area, and 2.5 baths—delivering current income while positioned to attract regional visitors and tourists. The lower level (~3,125 SF) offers flexible commercial space, partially configured as a vendor's mall and ideal for restaurant, retail, professional/medical office, pub, or multi-tenant uses. Prime downtown exposure and traffic create strong potential to grow both the STR performance and commercial income streams. Attractive basis well under $60/SF for an income-producing mixed-use asset with multiple paths to increased returns. Ideal for the investor seeking immediate cash flow plus value-add opportunity in a high-visibility location. Downtown town-square / HWY 25E location provides excellent visibility. Current STR baseline already exceeds typical Pineville market averages; the gap between current passive results and optimized performance is the primary value-add story. Strong candidate for investors focused on operational upside rather than pure turnkey yield.

110 W Kentucky Ave, Pineville

$459,000
26021827 MLS
*9 Reilly Road — Prime Commercial Opportunity Steps from Buffalo Trace* Buffalo Trace brings hundreds of thousands of people to their campus year in and year out. 9 Reilly Road is 500 feet from Buffalo Trace. You just need a fraction of those people to buy from your bourbon-themed gift shop, to stay in your AirBNB or grab a bite before or after a tour to be successful. Tons of parking and over 6,000 sq ft under roof gives you room to grow into, including 2,600 sq ft of covered parking or receiving area — leave it open for trucks and deliveries, turn it into a patio, or enclose it for even more finished square footage. Inside, several small rooms alongside one large open room, a garage bay, two restrooms, and a kitchenette mean the building flexes to whatever you're thinking. Multiple HVAC systems and drop ceilings make opening the space up or partitioning it further simple, without breaking the budget. Zoned CG, the possibilities here run wide: contractor home base, office, retail, restaurant, auto-related business, event venue, short-term rental, or a creative mixed-use concept — bring your vision and build new on the remaining lot, retrofit what's here, or both. Right down the road from one of Kentucky's most-visited attractions and a building ready to flex, this property pays for itself.

9 Reilly Rd, Frankfort

$249,900
4 Beds 2 Baths 26021218 MLS
This offering includes both sides of the duplex at 414 and 414½ Morrison Avenue. Each unit features two bedrooms and one full bathroom. Both units are currently rented for $625 per month, providing a combined gross monthly income of $1,250. Estimated market rents in the property's current condition are approximately $1,100 to $1,300 per unit, offering significant income-growth potential. The 414 Morrison Avenue unit was updated in 2014, while the 414½ unit has not been updated and offers an opportunity for future improvements and additional value. Neither side has a lease; both tenants currently occupy on a month-to-month basis. This is a solid opportunity for an investor seeking immediate rental income with substantial upside potential near downtown Lexington.

414 Morrison Ave, Lexington

$225,000
26020314 MLS
<br>174 Back Street offers a clean, updated commercial building in downtown Frenchburg, close to the Menifee County Courthouse, Sheriff's Office, and several established local businesses.<br><br>The approximately 1,173-square-foot interior has a flexible layout with two separate entrances, large rooms, plenty of storage, and a half bath. The front lobby includes a granite counter, giving customers or clients a defined reception area as soon as they walk in. An elevated section inside could be used as a display platform, additional seating, a private work area, or part of a showroom setup.<br><br>The layout could easily serve one business or be divided for two separate operations. It may work well for professional offices, retail, personal services, a salon, studio, meeting space, or a small business looking for room to grow.<br><br>The building has reinforced block walls, concrete flooring, a tankless water heater, 200+ amp electrical service, and an owned security system. Outside, the sealed and paved lot provides eight or more parking spaces, making access convenient for customers, employees, or future tenants. Public water and sewer are already connected.<br><br>Frenchburg continues to see more activity from visitors heading to Cave Run Lake, Red River Gorge, and the surrounding outdoor recreation areas. That added traffic creates opportunity for businesses that serve both local residents and travelers.<br><br>Use it for your own business, split the space between two uses, or purchase it as a commercial rental. This is a practical downtown property with solid construction, good parking, and several ways to make the space work.

174 Back St, Frenchburg

$899,900
26020101 MLS
Prime Mixed-Use Investment Opportunity on Kentucky's Bourbon Trail. 113, 115 & 117 South Main Street, Lawrenceburg, Kentucky. Don't miss this exceptional downtown investment opportunity in the heart of historic Lawrenceburg, Kentucky. This fully renovated mixed-use property is ideally located on the world-famous Kentucky Bourbon Trail, attracting visitors year-round. The property features three beautifully renovated and professionally decorated studio short-term rental units occupying the entire second floor of 117 South Main Street. At 115 South Main Street is The Lineage Kitchen & Bar, a newly renovated restaurant known for its exceptional food, craft cocktails, and vibrant dining experience. At 113 South Main Street is the Lawrenceburg Tourism Office, providing a stable commercial presence in a highly visible downtown location. Situated in the center of downtown Lawrenceburg, this property is just minutes from several renowned bourbon distilleries, including Wild Turkey Distillery, Four Roses Distillery, Whiskey Thief Distilling Co., and Larrikin Bourbon Company. Its prime location on the Bourbon Trail creates strong demand for short-term lodging while benefiting from consistent pedestrian traffic and year-round tourism. This rare opportunity offers a fully renovated, income-producing mixed-use property with multiple revenue streams generated by three turnkey short-term rental units, an established restaurant space, and a commercial office tenancy. Whether you're looking to expand your investment portfolio or acquire a premier downtown asset in one of Kentucky's fastest-growing tourism markets, this property offers exceptional income potential and long-term appreciation. A true turnkey investment in the heart of Bourbon Country. Owner is a licensed real estate agent in the state of KY.

113, 115, 117 Main, Lawrenceburg

$1,450,000
26019698 MLS
A rare opportunity to own one of Cynthiana's most recognizable and beloved businesses, Biancke's Restaurant has been serving the community since 1894, making it a true landmark with more than a century of history, tradition, and loyal customers. When you purchase Biancke's, you're not simply acquiring the real estate at 102 South Main Street in Cynthiana —you are investing in a well-established brand, an outstanding reputation, and a thriving business with a customer base that has already been built over generations. Strategically located in the heart of historic downtown Cynthiana, the property consists of three adjoining buildings seamlessly connected into an inviting main dining area with seating for approximately 175 guests. The 2019 addition of The Station at Biancke's expanded the restaurant with an additional 50 indoor seats and 50 outdoor patio seats, creating even more opportunities for dining, entertainment, and special events. Above the main restaurant is a spacious private banquet hall with seating for approximately 60 guests, currently not in use and offering tremendous potential for private parties, corporate events, rehearsal dinners, receptions, or additional business expansion. Known as the community's gathering place, Biancke's welcomes guests from breakfast through dinner while hosting countless family celebrations, bridal and baby showers, rehearsal dinners, business meetings, and memorable evenings with friends. Its longstanding presence has made it an integral part of the fabric of the community. Adding to the property's value, two beautifully renovated apartments on the second and third floors were completely remodeled in 2020 with exceptional attention to detail. Currently operating as a long-term rental and a successful Airbnb, these units provide valuable supplemental income while enhancing the property's investment appeal. This is a true turnkey operation, offering the rare chance to own an iconic Kentucky restaurant with multiple income streams, significant seating capacity, and an unmatched legacy. Continue a tradition that has thrived for more than 130 years while writing the next chapter in the story of one of downtown Cynthiana's most treasured destinations.

102 S Main St, Cynthiana

$57,500
26016838 MLS
Located on Main Street in the heart of Hazel, Kentucky, this 2,775-square-foot retail building offers an exceptional opportunity to own commercial real estate in one of Western Kentucky's most recognizable shopping destinations. Known throughout the region for its collection of antique stores, specialty shops, and small-town charm, Hazel attracts visitors from Kentucky, Tennessee, and beyond, creating consistent customer traffic throughout the year. The building features a flexible open retail layout that can easily accommodate a variety of business concepts, including a boutique, antique store, gift shop, home décor retailer, specialty market, art gallery, or other customer-focused business. With excellent visibility along Main Street, convenient parking, and immediate availability, the property is well positioned for both owner-users and investors. Whether you're expanding an existing business, launching a new retail concept, or adding an affordable commercial asset to your investment portfolio, this property offers an outstanding combination of location, visibility, and long-term potential in one of the region's most unique retail markets.

210 Main St, Hazel

$3,790,000
26008699 MLS
Highly Visible Downtown Office Space or amazing redevelopment opportunity. Position your brand at the center of it all. This iconic office building offers a rare combination of high-profile visibility and unparalleled convenience in the heart of downtown Lexington.Designed for firms that value both prestige and practicality, this property ensures your team and your clients are always exactly where they need to be. Situated on a high-traffic corridor, the building's striking architecture provides a "billboard effect" for your business, capturing the attention of thousands of commuters and pedestrians daily. Onsite Private Parking: Say goodbye to the downtown "parking hunt." This building features a dedicated onsite parking lot, providing seamless access for employees and a premium, stress-free experience for visiting clients.Walkable Urban Lifestyle: Step out the front door and into Lexington's vibrant core. You are minutes away from the District Courts, City Hall, and the city's finest dining, coffee shops, and banks. Building consists of 24 offices 8 half baths, 2 break areas, 1 training room, Server Room, File room, 2 copy rooms and a reception area. Don't miss the opportunity to occupy one of the most recognizable professional hubs in Central Kentucky. Whether you are a growing tech firm, an established law practice, or a creative agency, this building offers the identity and infrastructure required for your next chapter of growth.

277 E High St, Lexington

$299,000
26015489 MLS
Prime commercial opportunity in the heart of downtown Mt. Sterling! Currently operating as a restaurant, this versatile property offers endless possibilities for entrepreneurs and investors alike. Whether you're looking to continue in the food industry or transform the space for retail, office, or another business venture, the groundwork is already in place. The sale includes the building along with valuable fixtures and equipment such as triple deck ovens, refrigerated prep tables, a 3-compartment sink, walk-in cooler, 60-qt mixer, ice machine, TVs, stainless steel tables, prep sinks, and hand sinks. Even better, an upstairs apartment is currently rented, providing immediate income potential. Please note: business does not convey—real estate, fixtures, and equipment only. Don't miss this rare downtown investment opportunity!

531 E Main St, Mt Sterling

$375,000
4 Beds 2 Baths 26013381 MLS
Rare opportunity to own a beautifully restored 19th-century duplex in the heart of downtown Lexington. Originally built in the late 1800s and thoughtfully renovated while preserving its historic character, this fully occupied property offers two spacious 2-bedroom, 1-bath units with tall ceilings, restored hardwood floors, updated kitchens and baths, and off-street parking. Recipient of a Historic Preservation Award, the property blends timeless architecture with modern functionality and dependable income potential. Situated just moments from downtown restaurants, entertainment, and local attractions, this is a standout investment in one of Lexington's most desirable and walkable neighborhoods. The neighboring sister duplex at 148 E Fourth Street is also available, creating a rare opportunity to acquire two side-by-side historic duplexes in a premier downtown location.

152 E Fourth St, Lexington

$250,000
25501481 MLS
Charlotte and Merle Rhodes have sucessfully operated the Hoagie Shop in Cumberland since 1993 and over the last few years have leased the restaurant to private individuals. Their desire now is to sell the real estate and continue their retirement. This iconic location in Cumberland has been known for good eats and sweet treats for many years. Perfect for a new owner who wants to continue in the restaurant business. Inside dining for approximately 50 patrons is part of the nearly 1,900 sq. ft on the first floor. Some outdoor dining. Drive thru window. Fire suppression equipment in the kitchen as well as a walk-in cooler and freezer convey. Storage is available in a nearly 400 sq ft building in the parking lot as well as approximately 800 sq ft. in the upstairs area. If the restaurant business is not for you, this highly visible commercial location is well suited to be used for medical or other business purposes. Paved parking area can easily accommodate 20 or more vehicles. Let me help you make this business property yours!

1611-1615 E Main St, Cumberland

$1,100,000
26015521 MLS
EXTREMELY RARE opportunity to own a small but highly visible corner commercial property located directly next to one of the area's top tourist attractions, PATTI'S 1880 RESTAURANT. With steady foot traffic and excellent street exposure, this unique property is ideal for a boutique hotel, coffee shop, retail shop, or creative commercial concept. The corner location provides easy access and maximum visibility, making it a smart investment in a high-demand area. Zoned for flexible commercial use, it offers endless possibilities for entrepreneurs or developers looking to make a lasting impact. Opportunities like this are ONCE IN A LIFETIME!!— So bring your vision and make it a destination. Total charm. Prime location. Unlimited potential.

1817 J H Obryan Ave, Grand Rivers

$949,000
25505918 MLS
This multi-building shopping center offers excellent visibility, accessibility, and income potential in the heart of downtown Cumberland. The property includes three buildings: one currently leased to an auto parts business providing steady income, one formerly occupied by Pizza Hut and ideally configured for a restaurant, and a 25,292-square-foot retail strip divided into five units. With ample parking and central heating and air throughout, the property is well positioned for retail, service, or dining tenants. Its location along one of Cumberland's most traveled corridors ensures strong traffic exposure and easy customer access. Whether you're an investor seeking reliable rental income or an entrepreneur ready to expand, this property offers an exceptional opportunity in a growing market.

1310 E Main St, Cumberland

$549,900
26006201 MLS
A versatile commercial property in Berea, KY, zoned B2 and positioned just off the Berea Bypass, offers exceptional visibility and a wide range of incomeproducing possibilities. The level 2.917acre lot provides extensive road frontage, making it ideal for signage, customer access, and future development. Multiple storageunit buildings already on site create an immediate revenue stream, with strong demand in the area for secure storage options. A house located on the property adds even more flexibility, functioning as a comfortable residence, a business office, or a rental unit depending on your needs. The combination of commercial zoning, existing infrastructure, and prime location within city limits makes this property well suited for entrepreneurs, investors, or anyone seeking a livework setup with room to grow.

1031 Hwy 1016, Berea

$1,115,000
26006077 MLS
Rare opportunity to acquire a fully renovated, multi-functional commercial asset in Danville with true live/work capability. This ±8,400 SF property includes a well-appointed office component, high-end residential living space, and a detached 5-bay shop situated on a fully secured, fenced yard—purpose-built for contractors, service businesses, or owner-users seeking operational efficiency. The main building offers approximately 5,600+ SF of office, residential, and basement space, including an upgraded ~1,800 SF upper-level residence finished well above typical standards—ideal for owner occupancy or supplemental rental income. The detached ±2,800 SF garage/shop features multiple bays and mezzanine storage, supporting equipment, fleet, and material operations. The property has been extensively updated between 2021-2022, resulting in minimal deferred maintenance and an effective age of approximately 8 years. The concrete/paved yard is fully secured with metal fencing and gated access—an increasingly hard-to-find feature in the local market. Located just minutes from downtown Danville, Centre College, and Ephraim McDowell Regional Medical Center, with quick access to US-127 and approximately 35 minutes to Lexington, this property delivers strong regional connectivity without the cost basis of larger markets. Zoned Industrial Business District (IBD), the property supports a wide range of industrial, office, and service-based uses, offering flexibility for owner-users or investors. Multiple income strategies available, including full occupancy, partial leasing, or multi-tenant configuration.

446 Roy Arnold Blvd, Danville

$348,000
3 Beds 6 Baths 26002158 MLS
Owner financing or lease option to qualified applicant Exceptional commercial building located in the heart of downtown Vanceburg, directly across from both courthouses and just one block from three banks and the city office building. High-visibility location ideal for business and income-producing opportunities. Property offers 10,000+ sq ft with ample parking and multiple-use potential. Main Level: Retail/restaurant/diner space, 2offices,2 half baths, meeting or private event area with kitchenette, and an additional half bath. Recent updates include new cafe windows. Upper Level: Three-bedroom, two-bath apartment featuring kitchen, den, utility room, and an outdoor terrace patio with fireplace and river view. Additional Upper-Level Space: Separate Second Street entrance to 2- three room office suites with 2 separate hallway bathrooms. Excellent opportunity for mixed-use, professional offices, restaurant, retail, or investment property. Lots of equipment goes with sale

89 Second St, Vanceburg

$195,000
25004468 MLS
. This is an opportunity to own the former Cumberland United Methodist Church building, residence, parking lot, and grounds located at "the foot of Main Street", at the intersection of Main and Frazier streets in Cumberland, KY 40823. This historical property is a Cumberland landmark and a great location to start, or relocate, your worship center. The property is ideal for religious, or other, uses. It is in the business zone. The main floor is approx. 2,240 SF +/- and consists of a sanctuary, entrance foyer, choir loft, and offices. The ground floor is also 2,240 SF +/- and has a large gathering/dining area, smaller classrooms, kitchen, and two restrooms. The residence has approximately 1,670 SF+/- on the main floor with a LR, DR, kitchen, 4 bedrooms, and 2 full bathrooms; there is also a full unfinished basement, including a garage that is accessed from Fugate Drive. The house and church building are conveniently connected via a corridor leading from the ground floor of the church to the basement of the home. The paved parking lot is accessible from Fugate Drive and has 20+/- parking spots plus a covered carport and small storage building.

102-104 Frazier St, Cumberland

$400,000
4 Beds 2 Baths 26013380 MLS
Rare opportunity to own a beautifully restored 19th-century duplex in the heart of downtown Lexington. Rich in original character and thoughtfully renovated while preserving its historic charm, this fully occupied property offers two spacious 2-bedroom, 1-bath units with tall ceilings, restored hardwood floors, updated kitchens and baths, and off-street parking. Just steps from downtown dining, entertainment, and local attractions, this award-winning property combines timeless architecture with dependable income potential in one of Lexington's most sought-after locations. An additional opportunity awaits, as the neighboring sister duplex is also being offered for sale, presenting the potential to acquire a unique side-by-side portfolio in a highly desirable downtown location. Priced BELOW 2025 Appraisal.

148 E Fourth St, Lexington

$749,000
8 Beds 4 Baths 26015659 MLS
An exceptional opportunity to acquire a turnkey portfolio of two neighboring, fully occupied historic duplexes in the heart of downtown Lexington. Originally built in the late 1800s and thoughtfully restored while preserving their historic character, these award-winning properties offer a total of four spacious 2-bedroom, 1-bath residences featuring tall ceilings, restored hardwood floors, updated kitchens and baths, and convenient off-street parking. The package includes a shared off-street parking lot serving both buildings, adding convenience for residents while enhancing the long-term value and functionality of the portfolio. Fully occupied and meticulously maintained, these neighboring duplexes seamlessly blend timeless architecture with modern updates and dependable income potential in one of Lexington's most desirable and walkable neighborhoods, just steps from downtown restaurants, entertainment, shopping, and local attractions. Ideal for investors seeking a stabilized, income-producing asset, this portfolio also presents an outstanding opportunity for an owner-occupant. Live in one unit while the remaining residences help offset your mortgage, create a multigenerational living arrangement, or capitalize on future rental upside. Whether maintained as a long-term cash-flow investment, repositioned through future rent optimization, or utilized as a premium house hack, the portfolio offers multiple value-creation strategies. Priced well below its 2025 appraised value, this offering provides the potential for immediate equity in addition to dependable cash flow and long-term appreciation. Opportunities to acquire two adjacent, Historic Preservation Award-winning duplexes with a shared parking lot in such a premier downtown location are exceptionally rare. This is a truly one-of-a-kind chance to own a landmark investment in one of Lexington's most sought-after neighborhoods.

148 152 E Fourth St, Lexington