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$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

Listing courtesy of Gregory Leveridge of Block + Lot Homes.

$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

Listing courtesy of Bradley Warford of Century 21 Pinnacle.

$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

Listing courtesy of Janet C Wigginton of Keller Williams Commonwealth.

$219,000
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

Listing courtesy of Janna L Smith of United Real Estate Bluegrass.

$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

Listing courtesy of Brittany Martin of eXp Realty, LLC.

$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

Listing courtesy of Chaz Lents of Lifstyl Real Estate.

$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

Listing courtesy of Curtis Brown of Keller Williams Commonwealth - Stanford.

$459,000
3 Beds 1 Baths 26008141 MLS
Own a piece of Lexington History-The Adam Rankin House Circa 1784. Rare opportunity to own what is believed to be Lexington's oldest houses. Rich in character and history this house offers timeless charm paired with modern conveniences. Inside a wide central hall separates a spacious kitchen with a fireplace on one side and a large living room with a fireplace on the other.Upstairs you will find three bedrooms-two featuring original fireplaces as well as a bathroom with an adjoining dressing room. Beautiful hardwood floors, original architectural details, and thoughtfully preserved historic features can be found throughout the house. Comfortably updated offering central heat and air, modern appliances, and recently renovated kitchen and bathroom. Enjoy a fenced backyard with a storage shed. Perfect for gardening or quiet relaxation. located in the heart of downtown lexington on historic Mill Street. Rupp Arena, the University of Kentucky, the convention center, restaurants and entertainment center are all locate within feet of this unmatched location. Adam Rankin House is for anyone valuing history, character, and convenience-truly one of a kind.

317 S Mill St, Lexington

Listing courtesy of Jane C Pappas of Keller Williams Bluegrass Realty.

$91,900
4 Beds 1 Baths 26004195 MLS
Investment Opportunity - Victorian Revival with Renovation Potential 1960s Victorian Revival-style home featuring ornate woodwork and a dramatic curved staircase that highlights the timeless character of this spacious property. Offering 3,206 sq. ft. of living space, this two-story home showcases architectural details that reflect the elegance and craftsmanship of classic Victorian design. From the moment you enter, the eye-catching stairwell with its traditional curved geometry creates a striking focal point, complemented by vintage interior elements waiting to be revitalized. The home features 4 bedrooms with a primary bedroom conveniently located on the first floor, along with expansive living areas that provide excellent potential for renovation and reimagining. Much of the home's original charm and architectural character remain, offering the perfect canvas for an investor or renovation enthusiast to restore and enhance with modern updates. Key system updates include a metal roof, water heater approximately 3 years old, and gas furnace replaced approximately 6 years ago, providing a solid foundation for future improvements. With the right vision and creativity, this property has the potential to become a beautifully restored Victorian residence or a standout investment property. Property is being sold AS-IS. Home will not qualify for traditional financing. CASH Buyers Only. looked up closing and active properties from 2025 to present with results as follows: CASH Buyers Only.-The kitchen has been partially demoed with cabinets and fixtures already removed, providing a blank slate for your custom design kitchen. NOTE* researched minimal updated upto renovated -comparable in downtown Mt Sterling with price per sq ft range from Close Properties from 2025- 2026 ranging cost per square foot from $84.00- $120.00 with homes with limited upgrades to major Renovation, When calculating 3308 Camargo Dr. with 3206 Sq ft. Utilizing this information to calculate potential value post rehab, The closed prices range $269,000. to $384,720. The Active for-sale properties range from $110. to $153. per sq ft = calculated at 3206 sq ft - ranging lowest to highest $352,000 to $490,000. calculation (3206 Sq ft living space in 3308 Camargo Dr

3308 Camargo Road Mt, Mt Sterling

Listing courtesy of Janet L Jones of RE/MAX Elite Lexington.

$269,900
4 Beds 3 Baths 26006934 MLS
This charming 4-bedroom home in the heart of downtown Springfield offers space, character, and convenience all in one. Featuring over 2,100 finished square feet across multiple levels, the home includes a partially finished walk-out basement, providing flexible living or entertaining space. The interior showcases a mix of hardwood and carpet flooring, a cozy family room with fireplace, and a functional layout ideal for everyday living. The kitchen comes fully equipped, with all appliances conveying, making this a true move-in ready opportunity. Additional highlights include a detached garage, driveway parking, and a spacious lot just under a quarter acre. With public utilities, both electric and natural gas systems, and a prime location close to local amenities, this property offers the perfect blend of comfort and accessibility.

206 E Grundy Ave, Springfield

Listing courtesy of Taylor Peoples of Oak & Acre.

$1,200,000
26009850 MLS
32 acres wooded • 10 bed / 10 bath • Multi-unit commercial opportunity • Guest house + turnkey apartments • 2 office spaces • Listed under appraised value Rare opportunity offering scale, acreage, and multiple income-producing configurations on approximately 32 wooded acres. Originally built in 1991, the property includes reinforced flooring systems and handicap-accessible design elements, supporting flexible commercial, residential, or mixed-use applications. The main structure features 10 bedrooms and 10 bathrooms with a finished basement that expands usable living or operational space. The property also includes two dedicated office spaces, providing functionality for on-site management, administrative use, or conversion into additional operational or rental space (subject to zoning and approvals). Additional structures include a detached guest house and two upstairs units already configured in turnkey condition, allowing for immediate occupancy or rental potential. The layout supports separation of units while maintaining connectivity for larger-scale use if desired. With approximately 11,378 sq ft of total interior space, the property supports a variety of investment strategies including multi-family housing, short-term rental operations, workforce housing, group lodging concepts, or mixed-use commercial applications. The flexible configuration allows multiple income streams from a single site. The 32-acre setting is heavily wooded, offering privacy, natural surroundings, and potential for future expansion or additional development depending on intended use. The land provides space for parking, additional structures, or outdoor functionality tied to commercial operations. Located within reach of Clay City and Stanton-area services, the property maintains access to regional routes connecting toward the Red River Gorge recreation corridor, dining, grocery, and service hubs. This property is listed under appraised value, presenting a compelling opportunity for investors seeking scale, multiple units, office functionality, and land value in one package with existing structural readiness and immediate-use potential. Includes: finished basement, guest house, two turnkey upstairs units, two office spaces, reinforced flooring system, handicap-accessible design elements, and wooded acreage setting.

1429 Brush Creek Rd, Clay City

Listing courtesy of Ashley Schirmer of Berkshire Hathaway HomeServices Foster Realtors.

$245,900
3 Beds 2 Baths 26009082 MLS
This charming Cape Cod Home is located walking distance to downtown. Cute as can be! There have been numerous updates in the past including total kitchen and downstairs bath renovation! The owners have taken loving care of this home. Crown molding, mantle, banister, entry hardwood has been refinished, carpet over hardwood, stone fireplace with gas logs, ample walk-in closets, full unfinished basement with work bench, 1 car detached garage & fenced yard are just a few amenities that are featured in this older home with updates! Main level offers bedroom & full bath with a jacuzzi and skylight, formal dining room, living area, and an updated kitchen with island bar ample cabinets and all appliances. This lovely kitchen has a Greenhouse window to provide optimal light for growing your plants indoors. Don't miss out on this little jewel of a home.

301 S 3rd St, Nicholasville

Listing courtesy of Brenda J Bellman of RE/MAX Elite Realty.

$449,900
2 Beds 3 Baths 26015300 MLS
Welcome to Newpast on Main—one of downtown Lexington's best-kept hidden gems. This stylish 2-bedroom condo at 622 W Main St offers contemporary living in an unbeatable location, just minutes from everything downtown has to offer. Step inside to find a sleek, modern interior with zero carpet throughout, creating a clean and low-maintenance living space. A brand new geothermal unit has just been installed, providing energy-efficient comfort year-round. What truly sets this condo apart are the incredible outdoor spaces. Enjoy stunning views of Gatton Park and Rupp Arena from the rooftop patios—perfect for relaxing or entertaining. The community also features a beautiful, tree-lined shared walkway and a charming common area patio, adding to the peaceful, tucked-away feel. Priced under market value to sell quickly, this is a rare opportunity to own a move-in-ready condo in a prime downtown location. Don't miss your chance to own this hidden gem!

622 W Main St Unit 110, Lexington

Listing courtesy of Kelley B Kelley of Keller Williams Legacy Group.

$185,000
3 Beds 1 Baths 26013165 MLS
Welcome to this charming Craftsman-style home just minutes from downtown Carlisle! With more than 1,800 square feet of living space, this 3-bedroom, 1-bath home offers a great mix of character, comfort, and versatility. Inside, you'll find a spacious front room that creates a welcoming first impression and is currently used as a dining area. The main floor also includes a large living room with a cozy fireplace, a spacious kitchen, a convenient laundry room and a first-floor bedroom. Upstairs are two additional bedrooms and a roomy landing area that would make a perfect home office, reading corner, play space, or flex area to fit your needs. Just off the kitchen, the bright sunroom provides even more options—use it as a dining room, sitting area, office, or extra gathering space. Outside, the home sits on a beautifully landscaped 0.35-acre corner lot shaded by mature trees. Additional features include an unfinished basement for storage, a detached one-car garage, a storage shed, and a large rear deck that's ideal for entertaining or relaxing. The covered front porch, complete with a classic porch swing, adds to the home's inviting curb appeal and timeless charm. Conveniently located near local shops, restaurants, schools, and all that downtown Carlisle has to offer, this home combines small-town charm with everyday convenience.

319 N Elm St, Carlisle

Listing courtesy of Michelle R Blackburn of RE/MAX Creative, Winchester.

$348,700
4 Beds 2 Baths 26000475 MLS
Finally— A Luxury Townhome Investment That Actually Make Financial Sense! Now offering these stunning new-construction townhomes that combine luxury finishes with long-term value. Featuring soaring, minimum 12-foot vaulted ceilings throughout, these homes offer a sense of space that rivals most single-family homes. The primary bedroom is truly massive—bigger than what you'd find in many full-sized houses. Made to last a long time, each unit showcases upgraded thick matte black siding and modern tongue-and-groove pressure-treated pine soffits for both style and durability. Tucked away at the end of a quiet dead-end street and backing up to a peaceful open field, these 2-bedroom, 1-bathroom homes offer privacy. You'll also enjoy a covered front porch, side deck, and an oversized one-car garage for added convenience. Inside, the spacious living room easily accommodates your entertainment and lounging setup, while the custom kitchen features built-in cabinetry and granite countertops. Whether you're looking for a beautiful place to live or a smart addition to your investment portfolio, this property delivers. Call today before they're gone!

323 Randolph St, Somerset

Listing courtesy of Nathanael Sears of Keller Williams Commonwealth - Somerset.

$239,000
26016572 MLS
Discover a prime lot in the Paducah City Annex offering exceptional convenience for future development. Close to churches, banks, Murray State University's Paducah Campus, WKCTC, Kentucky Oaks Mall, restaurants, and entertainment. Quick access to I-24 adds valuable connectivity for residents or investors. Situated within the scenic 30-acre Woodland Reserve, this property also offers the advantage of 9 additional lots available, providing flexibility for expanded building plans or multi-lot opportunities in one of Paducah's most desirable and fast-growing areas, ideal for long-term investment vision. A rare chance to secure land in a location that continues to attract strong interest.

5100 Hill Ter, Paducah

Listing courtesy of Alberta Davis of Better Homes and Gardens Fern Leaf Group.

$5,700,000
26011350 MLS
Introducing a stunning, four-story mixed-use architectural gem positioned in the absolute heart of downtown Lexington. This premier property offers an unparalleled live-work-play dynamic, crowned by exclusive ground-floor prestige and exceptional upper-level versatility. The Ground Floor: Home to an ultra-exclusive, private club featuring an intimate atmosphere, high-end finishes. Floor 2 Flooded with natural light, these expansive floors offer flexible layouts perfect for high-end boutique offices, or creative studio spaces overlooking the vibrant cityscape. Floor 3-4 5 luxury Air B&B units. Once outside and you are seconds away from Lexington's finest dining, bourbon bars, and cultural landmarks. With its irreplaceable location, distinct historic-meets-modern character, and diverse income streams, this building is a trophy asset for the discerning investor.

144 N Broadway, Lexington

Listing courtesy of Christopher Mitchell of Bluegrass Sotheby's International Realty.

$219,900
4 Beds 2 Baths 26010906 MLS
NEW 30 yr warranty on roof that transfers to new owner. New plywood roof covering, shingles and box vents. Three chimneys removed on roof and reconstruction of an updated roof. Step in to timeless charm with this spacious 2-story home located in the heart of historic Carlisle. Home features include four large bedrooms and 2 full baths. Updated features include new bathroom and flooring in several rooms. Large dining/family room for large family gatherings. Huge back patio for entertaining. Large fenced in corner lot. 10X30 storage building. This home offers the charm of small town living with room to grow, entertain and make lasting memories. If you love historic homes with modern updates and plenty of outdoor space, this one is a must see!

330 Sycamore St, Carlisle

Listing courtesy of Johnny Perry of KY Local.

Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.