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$375,000
25500832 MLS
Own a piece of history in the heart of downtown Harrodsburg with this rare opportunity to purchase two beautifully restored historic buildings on Main Street. Offering the perfect blend of timeless charm and modern updates, this turnkey investment property is ready to generate immediate income and long-term value. The main level features two spacious street-level storefronts, ideal for retail shops, cafes, or professional offices. With excellent visibility, steady foot traffic, and prominent Main Street frontage, these spaces offer prime commercial exposure. Both buildings have been recently updated, preserving their historic character while providing functional and attractive interiors. Upstairs, you'll find three well-appointed one-bedroom residential apartments. Each unit has been thoughtfully renovated with modern finishes and is in excellent condition, making them perfect for long-term tenants, short-term rentals, or even a live/work setup. Located in Kentucky's oldest city, Harrodsburg is a vibrant and welcoming community with deep historical roots. The property is surrounded by other thriving local businesses, restaurants, and cultural attractions, and is just a short drive from Danville, Lexington, and major regional thoroughfares. With multiple income streams and strong potential for appreciation, this property presents an exceptional opportunity for investors, entrepreneurs, or business owners looking to establish or expand in a growing downtown market. Whether you're looking to enhance your portfolio or set up shop in a historic setting, this Main Street gem offers flexibility, functionality, and lasting appeal. (Note: some photos are not current)

120 S Main St, Harrodsburg

$299,900
2 Beds 1 Baths 26005507 MLS
The Thomas Barbee House, built circa 1790 and on the National Register of Historic Places and Kentucky's famed Bourbon Trail, presents the rare opportunity to own a piece of American history brought into this century. On the same block as downtown Danville's Constitution Square, the "birthplace of Kentucky," and walking distance to Centre College, the Thomas Barbee House recently underwent a major renovation, restoring its walls, ceilings and floors to the 18th century while bringing its interiors to the 21st. A single-pen, two-story log cabin made of white oak logs, the Thomas Barbee House features a first-floor, open-living concept with a modern kitchen and inviting living room with a gas fireplace. A spacious bedroom, laundry room and bathroom comprise the second floor, while the third floor sleeping loft welcomes extra guests. Zoned residential and commercial, the Thomas Barbee House is turnkey for any endeavor, especially a short-term rental for visitors to Danville, Centre College, and those exploring the Bourbon Trail. An additional lot presents the opportunity for residential or commercial expansion. Thomas Barbee, a Revolutionary War officer, was awarded land grants in Kentucky for his military service. He built the Thomas Barbee House near Danville's first post office where he reported to work as the first postmaster west of the Alleghenies. The original post office where he worked is walking distance from the cabin in Danville's Constitution Square as is Barbee's gravestone in Danville's beautiful Bellevue Cemetery. The renovation journey of the Thomas Barbee House can be viewed on Instagram @a.shot.of.yesterday

202 E Walnut St, Danville

$350,000
2 Beds 3 Baths 25505346 MLS
Endless Potential in the Heart of Historic Perryville! Discover a rare opportunity to own a piece of Kentucky's history with this former Perryville Presbyterian Church, originally constructed in 1800. Nestled in the heart of Perryville's Historic District, this timeless property blends architectural beauty with endless creative potential. The building showcases early 20th-century charm, featuring original stained glass windows, soaring vaulted ceilings, and detailed woodwork that reflect true craftsmanship from a bygone era. Expansive open spaces and abundant natural light make it the perfect canvas to transform into a stunning private residence, event venue, studio, or bed-and-breakfast. Surrounded by historic landmarks and small-town character, this unique property offers both heritage and opportunity—ideal for anyone with a vision to restore and reimagine a piece of Kentucky's past into a beautiful modern living space. Sold As Is. Agent owner

303 S Bragg St, Perryville

$374,900
4 Beds 3 Baths 26013989 MLS
Classic charm meets modern convenience at 616 E. Main Street in the heart of Danville. Situated on nearly half an acre, this beautifully updated Cape Cod offers over 2,300 square feet of living space with 4 bedrooms, 2 full bathrooms, and 1 half bath. Originally built in 1920, the home blends timeless character with thoughtful updates designed for today's lifestyle. Step inside to discover spacious living areas, luxury vinyl flooring, and a functional floor plan highlighted by a desirable first-floor primary suite complete with a walk-in closet and private bath. The large great room creates an inviting gathering space, while two fireplaces add warmth and character throughout the home. The updated kitchen is designed for both everyday living and entertaining, featuring quartz countertops, ample workspace, and plenty of storage. Whether hosting family gatherings or preparing a quiet meal at home, this space is both functional and inviting. Additional bedrooms provide flexibility for family, guests, a home office, or hobby space, while the home's thoughtful layout offers room to spread out and enjoy. An unfinished partial basement provides valuable storage space and additional room for hobbies, projects, or future possibilities. Outside, the welcoming front porch invites you to slow down and enjoy life in one of Danville's most established neighborhoods. The nearly half-acre lot provides room for outdoor entertaining, gardening, pets, or future possibilities rarely found this close to downtown. Conveniently located near downtown Danville, shopping, dining, parks, and schools, this home offers the perfect combination of historic charm, modern comfort, and an exceptional in-town setting. If you've been searching for character, space, and location, 616 E. Main Street deserves a place at the top of your list.

616 E Main St, Danville

$420,750
26001732 MLS
Outstanding Commercial Opportunity with active STR/Boutique Hotel Seize the chance to utilize 6,250 square feet of exceptional commercial space on the ground and upper levels, strategically located in the bustling town square of Pineville. This high-traffic location (HWY 25E) ensures incredible exposure and easy access, making it an ideal site for your next business venture. Currently, the lower level is 3125 sq ft and is partially designed as a vendor's mall, offering a flexible layout suitable for a wide range of business types, including a lively restaurant, professional office space, medical office, pub, or retail storefronts. A unique feature of this property is the well-established Boone Trace Inn (active STR) on the upper level, which includes 7 private beds equipped with coded entry doors, perfectly positioned to attract visitors and tourists. The common areas are designed for comfort and convenience, featuring a generous gathering room, a fully equipped kitchen, a spacious dining area, and 2.5 baths, all enhancing the property's attractiveness. With an appealing price point under $80 per sf, this property presents an incredible investment opportunity.

110 W Kentucky Ave, Pineville

$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

$229,000
3 Beds 1 Baths 26016107 MLS
Welcome to 211 Willow Street, a 3 bedroom, 1 bathroom home offering 1,872 square feet of living space in a convenient Mt. Sterling location. Built in 2005, this home features a functional layout with laminate flooring on the main level and brand new luxury vinyl plank flooring in the basement, neutral paint colors, central heat and air conditioning, and a spacious kitchen complete with stainless steel refrigerator, stove/oven, dishwasher, and above-the-range microwave. Washer and dryer hookups are available on the main level, and the home is all electric with KU Electric and city water through Mt. Sterling Water & Sewer. One of the standout features of this property is the finished walkout basement, offering two additional bonus rooms and flexible space that is hard to find in this price range. One of the three bedrooms is located in the basement and features a window and exterior door. While many homes at this price point offer only one level of living space, this property provides the added benefit of a finished lower level that can be used for extra living area, bedroom, office space, hobby rooms, storage, or recreation. Outside, enjoy a wraparound deck, a 0.23-acre lot, and a large metal storage shed included with the sale. Conveniently located near schools and I-64, this home offers easy access to Winchester, Lexington, Paris, Jeffersonville, Camargo, Owingsville, Sharpsburg, Salt Lick, North Middletown, Preston, and Morehead. Seller is a licensed real estate broker in the state of Kentucky.

211 Willow Street Mt, Mt Sterling

$399,000
3 Beds 3 Baths 26014991 MLS
Beautifully situated on a spacious 0.60-acre lot with a custom built, climate controlled workshop, this 3-bedroom, 2.5-bath home offers 2,398 sq ft of character, charm, and functionality in the heart of Murray! Mature trees and attractive landscaping create outstanding curb appeal, while the home's classic architecture showcases timeless features including hardwood floors, built-in cabinetry, and a gas log fireplace in the living room. The main-level ensuite addition includes a large bedroom, dual walk-in closets, and a spacious bath with laundry area. Upstairs, you'll find two generously sized bedrooms and a central bath featuring dual vanities, a separate tub, and shower.The large 36x50 climate-controlled workshop is a rare find, complete with its own bathroom and kitchenette and a 10x24 lean-to. A large basement offers abundant storage, and the expansive lot provides plenty of room to enjoy the outdoors. This unique property combines historic character with modern convenience.

1106 Poplar St, Murray

$1,250,000
2 Beds 3 Baths 26010189 MLS
Experience elevated living at its finest in downtown's newest 36-unit condominium project, The Vine. This collection of one- and two-bedroom residences showcases thoughtfully designed interiors with refined finishes from floor to ceiling, creating a seamless blend of style and comfort. Each residence features a private balcony with city views, while community amenities include a rooftop pool and access to The Vine Club, offering an elevated social and leisure experience. Residents also enjoy concierge services, including a doorman, along with a professionally managed program for short-term rental opportunities. Ideally positioned in the heart of downtown Lexington, The Vine offers close proximity to Rupp Arena, the University of Kentucky, local dining, nightlife, and everyday conveniences. Imagine starting your mornings with coffee at a nearby café and ending your evenings taking in the energy of the city, all just steps from your front door. This is more than a residence; it is a lifestyle.

106 W Vine St Unit 603, Lexington

$1,750,000
23021742 MLS
101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development.

101 S Main, Winchester

$179,900
2 Beds 2 Baths 26014434 MLS
LUXURY, CHARM, and CHARACTER all in one! Step inside the stunning 2 bedrooms, 1 & 1/2 bath home with bonus areas, more modern update meet timeless craftsmanship. From the moment you arrive, you'll be captivated by the striking exterior, soaring ceilings, Rich hardwood floors, and abundance of natural light throughout. The beautifully updated kitchen features crisp white cabinetry, subway tile backsplash, designer lighting, and black appliances that create a stylish and inviting space for cooking and entertaining. The spacious living room showcases vaulted ceilings, elegant chandelier, and an open, airy feel rarely found in homes of this size. Upstairs the oversize bedrooms offer beautifully architectural details, hardwood flooring, and generous closet space. The updated bathroom provide a spa all like atmosphere with modern finishes and thoughtful design. Outside is where the property truly shines! Relax around the lounge area, or enjoy the expensive multi level decking that creates The perfect setting for entertaining guests. The fence yard provides privacy while the mountain views in stunning somerset skies create a breathtaking backdrop. Whether you're searching for a primary residence, we can get away, or investment property, this one of a kind home offer style comfort inn outdoor living that is hard to find

214 Spruce St, Pineville

$165,000
2 Beds 1 Baths 26012173 MLS
Charming and full of character, this 2-bedroom, 1-bath home offers an excellent opportunity for first-time buyers, downsizers, or anyone looking for an affordable place to call home. From the inviting foyer entry to the beautiful hardwood flooring and decorative exterior woodwork, this home showcases timeless charm throughout. The functional floor plan features a centrally located living room, two comfortable bedrooms, and a spacious kitchen and dining area at the rear of the home with plenty of room for gathering, cooking, and entertaining. A dedicated laundry/utility room adds convenience, while the privacy-fenced backyard and rear deck provide space to relax, garden, or enjoy outdoor activities. Move-in ready with room to add your own personal touches over time, this home offers both comfort and potential. FHA buyers are welcome, and the seller is offering a concession toward kitchen appliances with an acceptable offer, making it even easier to make this home your own.

151 Rand Ave, Lexington

$599,900
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

$284,000
1 Beds 1 Baths 26015655 MLS
This is a mixed used building that's for sale for $284,000: entire building. The residential portion is the main floor back portion, which is best set up as a studio, and the top floor, which is unfinished but has been approved with Scott Co P/Z to be two residential units - blank slate. The front main portion of the building is zoned for commercial use. Ideal for an owner who would like to live and work in the same structure, or for an investor who'd like to lease the main floor for business and residential tenants separately or together, and finish out the top floor for additional residential income. This space could also be utilized for storage. Set up for as the ultimate in flexibility, with great visibility. The top can also be leased for $600, and the bottom for $1795. Description: Super opportunity to own a unique corner of Stamping Ground, Kentucky. Beautiful space that just FEELS good when you walk in. Gleaming hardwoods, shelving in front room, loads of natural light from large windows facing Main Street, making for a great storefront or business space. Building is zoned B3; a portion of the main level can be utilized for residential, while the front portion with windows facing Main Street is to be used for commercial/business. Large kitchen, bathrooms, dining area, offices ... Great way to live where you work! Upstairs with separate entry, there is unfinished space that is set to be turned into two residential units - apartments - that can be leased separately. Currently it's wide open and could also be leased for storage space for additional income. Schedule a showing with your realtor, have them reach out for details - there are numerous opportunities for income, personal business use, or private residential use. Buyer to verify all aspects of property including but not limited to square footage, use, and condition.

3364 Main St Unit A, Stamping Ground

$225,000
3 Beds 2 Baths 26011961 MLS
Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$89,900
2 Beds 1 Baths 26004299 MLS
Charming country-style home located within the city limits of Mount Vernon, KY, offering privacy and convenience just minutes from local amenities. This well-constructed and well-insulated home features two spacious bedrooms with hardwood flooring and one full bathroom with laundry hookups. A mini-split system provides efficient and adequate heating and cooling for year-round comfort. The property sits on just under 4 acres, within the city limits, with an estimated 300 feet of road frontage along Richmond Street and additional frontage along Town Branch Rd. Outdoor features include an oversized detached one-car garage, a freestanding gazebo, and three additional outbuildings that offer potential for storage or workshop space with repairs. With its combination of acreage, location, and versatility, this property presents an excellent opportunity for first-time homebuyers, investors, or anyone seeking a home with room to grow.

780 Richmond St, Mt Vernon

$285,000
2 Beds 2 Baths 26014276 MLS
Distinguished by its character and enduring appeal, this all-brick residence offers 2 bedrooms, 2 full bathrooms, and a versatile bonus room suitable for a variety of uses. Hardwood flooring extends throughout much of the home, complementing the generous room sizes and functional layout. Thoughtfully designed for both comfort and practicality, the home features spacious bedrooms, an oversized laundry room, and flexible living spaces that accommodate a range of lifestyles. The covered front porch provides a welcoming introduction, while the fenced backyard offers additional space for outdoor enjoyment and entertaining. Combining timeless architectural charm with everyday functionality, this property presents a unique opportunity to own a home with character, substance, and lasting appeal.

302 College St, Sadieville

$459,000
3 Beds 4 Baths 26014332 MLS
A stunning Queen Anne Victorian nestled in the heart of Lexington's historic Elsmere Park neighborhood. Beautifully restored and thoughtfully renovated, this exceptional residence seamlessly blends timeless architectural character with modern comfort and convenience. Featuring 3 bedrooms, 2.5 baths, and nearly 2,000 square feet of living space, the home showcases soaring 10-foot ceilings, abundant natural light, gorgeous hardwood floors, and preserved original details that honor its historic charm. The spacious first-floor primary suite offers a spa-inspired retreat, while the gourmet kitchen boasts custom cabinetry, generous workspace, and an adjoining pantry and laundry area designed for everyday functionality. Elegant living and dining spaces provide the perfect setting for entertaining, while multiple outdoor living areas, including a porch, patio, and deck, invite you to relax and enjoy the beauty of this unique neighborhood. Situated just minutes from downtown Lexington, local dining, entertainment, parks, and the vibrant cultural scene, this home offers the rare opportunity to own a piece of Lexington history without sacrificing modern amenities. Historic elegance, modern luxury, and an unbeatable location—668 Elsmere Park is truly one of Lexington's most distinctive homes.

668 Elsmere Park, Lexington

$99,999
26004003 MLS
Prime 6.75 Acre Development Opportunity in Stanford City Limits Rare opportunity to acquire 6.75 acres inside the Stanford city limits in a highly desirable and growing area located just minutes from Lincoln County High School, downtown Stanford, and the major Highway 27 corridor. This versatile tract offers tremendous potential for a variety of development opportunities. The property is accessed by a 60' permanent access easement from Yates Road, providing ample width for a future entrance road and infrastructure. City water and electric are nearby, making the property well positioned for future development. If you're looking for land to build your dream home on and have land for the kids and family to roam.... this would work perfectly. Also with the new city zoning requiring a fairly minimum lot size, the tract appears well suited for a residential subdivision development with potential for approximately 16-18 residential lots, making it an ideal opportunity for builders or developers looking for their next project in a strong housing market. In addition to residential development, the size, location, and city-limit positioning also create excellent potential for commercial or investment uses, including: • Self-storage facility • Contractor or warehouse storage units • Business park or office complex • Retail or service-based businesses • Mixed-use commercial and residential development The property's proximity to schools, established neighborhoods, and major travel routes creates a highly desirable location for both residential and commercial investment. With minimal restrictions in place (no swine, poultry, or mobile homes), this property provides flexibility for a wide range of future development concepts. Whether you are a solo/family looking to build, builder, investor, or developer, this property offers the space, location, and infrastructure potential needed to bring your vision to life. Opportunities like this within the city limits of Stanford are becoming increasingly rare. This property is currently zone ag 1 due to being vacant when city annexed further out, however talking to city hall it has potential to become what you need and a rezone meeting will have to happen once you decide on the direction you want to go. Listing agent has all docs and paperwork for the property and the docs from city hall showing all the zoning rules. Property Highlights • 6.75 Acres • Located inside Stanford city limits • 60' permanent access easement from Yates Road • City water and electric nearby • Minimum sqft lot zoning • Potential for 16-18 residential lots (conceptual) • Minutes from Lincoln County High School • Close to downtown Stanford amenities • Excellent investment or development opportunity

19 Yates Rd, Stanford