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

415 S, Lexington

$725,000
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

$575,000
2 Beds 2 Baths 26015838 MLS
Accepting back up offers! The Woodlands is the most elegant and popular condominium development in Lexington. It is convenient to Downtown, University of KY, and Chevy Chase. This Second Floor corner unit has North East exposure for the morning sun and overlooks the lovely manicured gardens of the Woodlands on the North West side. The spacious floor plan features tall ceilings, hardwood parquet and plank flooring and many windows allowing for great natural light. There is a large Living Room with a bay window and Dining area, Kitchen with adjacent Den offering a cozy fireplace, two generous Bedrooms and two full Bathrooms. Special features are the plantation shutters, storage closet on the second floor and a large storage closet in the basement, along with the one car assigned parking in the Basement Garage. The many amenities in the Woodlands include 24/7 Security, formal main floor Entertainment areas and Game room, top floor patio for watching the sun set and Guest Parking in front by the inviting fountain.

111 Woodland Ave Unit 211, Lexington

$550,000
26012437 MLS
Prime commercial opportunity in the heart of downtown Frankfort! This 1,923 sq. ft. CB-zoned property offers exceptional visibility, character, and flexibility for a variety of business uses. Featuring exposed brick walls, soaring ceilings, abundant natural light, and a striking glass garage-style storefront, the space blends historic charm with modern appeal. The open floor plan provides endless possibilities for retail, office, restaurant, coffee shop, brewery, gallery, studio, or creative workspace. The property's unique design creates an inviting atmosphere while allowing a future owner to customize the space to fit their vision. A rare bonus in downtown Frankfort, the property includes an adjacent open lot on one side and a parking lot on the other, providing valuable flexibility for customer parking, outdoor seating, events, expansion opportunities, or future development. Located in a growing downtown corridor surrounded by local businesses, government offices, restaurants, and community attractions, this property is ideally positioned for both owner-occupants and investors seeking a distinctive property with unlimited potential.

335-337 W Broadway St, Frankfort

$499,900
5 Beds 3 Baths 26022132 MLS
The Collins-Evans house is now being offered for sale in North Middletown. This beautiful historic home dates back to 1894. On the historic registry, this treasure has been renovated with great love and taste by its current owner. Sitting on 2 acres, it is a gentleman's farm, but with all the conveniences within a small town. Inside you'll find large Victorian rooms with stunning original woodwork and doors, that includes five bedrooms and three full baths. The current owners have updated the home with new paint throughout and refinished the hardwood floors. Its Victorian charm continues upstairs with its winding staircase and bedrooms, including one that has been transformed into a personal living area. You enter the property through historic stone fencing to find a wraparound porch with easy access to the front and side of the house. Many exterior updates include new box guttering and soffits. A newly built roofed pergola with outdoor kitchen and a screened-in deck are found at the rear of the house. The newly fenced backyard is great for your dogs and includes a refurbished greenhouse. The rear acreage has a fenced orchard, a sizable paddock, and a three bay garage/barn with a large run-in shed and an enclosed horse stall. There is also a self contained workshop as well as a handy covered three sided shed for outdoor storage. You'll love living in peaceful North Middletown, and enjoy all that this property includes, as it has been genuinely and lovingly restored to its current condition. A list of the extensive updates is included within the seller disclosure, showing all that has been completed.

206 College Rd, N Middletown

$485,000
2 Beds 2 Baths 26020088 MLS
The newly renovated Nave-Werhle House is available for purchase. This charming cottage dates to 1877 and is beautifully situated on S. Winter Street in Midway Kentucky. The location is superb, just steps from the Downtown Midway and all of the amenities offered there. The home has been tastefully renovated recently with a new Kitchen and high quality appliances, new primary bathroom with large walk in shower, and newly painted inside and out! Other features include very nice hardwood floors, 10ft ceilings, vaulted ceiling in the primary bedroom, large walk in closet, built in cabinetry in the family room, a charming front porch and side deck/porch, a 1 car detached garage with carport and basement storage area. While technically a two bedroom, two bath residence, it is currently configured as three bedrooms. Take your pick...either way this a great house in an awesome location.

208 S Winter St, Midway

$479,900
4 Beds 2 Baths 26023671 MLS
Welcome to the perfect blend of small-town charm and peaceful country living. Just around the corner from Stanford's historic downtown—where locally owned restaurants, boutiques, and community events create a warm, welcoming atmosphere—you'll find this beautifully maintained 1872 farmhouse nestled on just over 1.5 picturesque acres in the heart of Central Kentucky. From the moment you step inside, you'll appreciate the timeless character of this historic home, thoughtfully complemented by tasteful modern updates that provide today's comforts (roof, a/c, water heater all less than 3 years old) while preserving its original charm. Rich in history and full of inviting spaces, this is a home designed to be lived in and loved. The main level features spacious living and dining rooms, a well-appointed kitchen with a conveniently concealed washer and dryer, a primary bedroom, and a full bath. Two additional flex spaces include a light-filled sunroom overlooking the peaceful backyard and a cozy den that's ideal as a home office, library, or sitting room. Adding to the home's historic appeal are both the original front staircase and a secondary rear staircase leading to the second floor. Upstairs, you'll find three additional bedrooms and a full bath. The expansive primary upstairs bedroom includes a beautiful sun-drenched bonus room with abundant storage, while the spacious bathroom features a classic claw-foot tub. A second bedroom offers an ideal office or hobby space, and the third bedroom provides comfortable accommodations for family or guests. Outdoor living is just as inviting. A welcoming partial wraparound porch offers the perfect place to enjoy morning coffee or evening sunsets, while the beautifully designed rear veranda creates an ideal setting for entertaining, relaxing, or taking in the peaceful views of the surrounding acreage. An oversized detached two-car garage includes floored attic storage, providing plenty of room for vehicles, equipment, and seasonal items. Properties like this rarely become available—a historic Kentucky farmhouse offering acreage, privacy, and convenience just minutes from downtown Stanford. Experience the best of country living without sacrificing the amenities of town.

221 Somerset St, Stanford

$455,000
4 Beds 3 Baths 26020871 MLS
Historic character. Modern luxury. Completely rebuilt for today's lifestyle. The property was also approved for a Conditional Use Permit in order to operate as a short-term rental! Completely restored from top to bottom, this historic stone home offers 4 bedrooms, 3 full bathrooms, and the rare combination of timeless architecture with all-new modern systems and finishes. Every detail has been thoughtfully updated while preserving the home's historic character. The spacious floor plan features bright living areas, a living room with a fireplace, and two sunrooms that provide additional flexible living space. The fully renovated kitchen offers quality finishes, ample cabinetry, and a functional layout for everyday living and entertaining. All three bathrooms have been completely updated with timeless finishes, including a spacious primary suite with a beautifully appointed ensuite bath. The main level includes the primary suite, an additional bedroom, and a full bathroom, providing convenient first-floor living. Upstairs are two generously sized bedrooms connected by a full bath. An unfinished basement offers abundant storage, and a detached two-car garage provides additional convenience. Major renovations include a completely updated electrical system, plumbing, HVAC, ductwork, tankless water heater, basement water proofing, floor drains, sump pump, and so much more. These extensive improvements provide the benefits of modern construction while maintaining the charm and craftsmanship of this historic home.

202 Paul Sawyier Dr, Frankfort

$450,000
25017945 MLS
Prime multi-use property located inside the city limits of Richmond, KY, offering excellent investment potential. Currently vacant, this property is ready for immediate occupancy and income generation. The rear portion features a one-bedroom apartment and a two-car garage, creating opportunities for rental income once leased. With three possible rental opportunities, this property offers multiple revenue streams. The main building provides just over 3,000 square feet of versatile space, ideal for retail, office, showroom, service-based business, or mixed-use operations. Located in a high-visibility area with easy access to shopping, dining, and major roadways, this property is zoned for a variety of commercial uses, making it well-suited for investors, entrepreneurs, or owner-operators seeking a strategic location with strong income potential. Main building has 3036 SF.

301 Steep St, Richmond

$435,000
1 Beds 2 Baths 26021104 MLS
Experience the best of downtown Lexington from this stylish condo in the highly desirable 500's on Main. Perfectly positioned in the heart of the city; you'll enjoy walkable access to Rupp Arena, Central Bank Center, Triangle Park, the Lexington Opera House, and countless local restaurants, breweries, and vibrant nightlife. The University of Kentucky, Transylvania University, and Lexington's major hospitals are just minutes away. This open-concept condo offers rich hardwood floors, exposed brick accents, and an inviting atmosphere making it ideal for everyday urban living. The spacious primary suite was originally designed as a two-bedroom layout and could easily be converted back if desired; offering flexibility to fit your needs. Situated on the second story, this unit enjoys beautiful city views while also providing ground-level access to the rear courtyard, creating an ideal combination of convenience and accessibility. This prime location truly puts the best of Lexington at your doorstep!

515 W Main St Unit 211, Lexington

$379,900
2 Beds 3 Baths 26013844 MLS
Welcome to Opera House Square! A conveniently located gated community in Downtown Lexington located a short walking distance to some of the city's best shopping, dining and entertainment. This property offers a nice open first floor including a nice sized living area w/ gas fireplace, dining room, kitchen and powder room/laundry area including washer/dryer. The 2nd floor includes a nice master suite with full bath, guest bedroom and a full guest bathroom. In addition, this property offers a private patio and storage shed. HOA fees are very reasonable at $180.00 per month and includes common area maintenance of the complex. This property has a reserved spot #15 and plenty of guest parking. Set your showing today before it is too late!! **48 hour kickout clause**

541 W Short St Unit 15, Lexington

$379,000
4 Beds 3 Baths 26009098 MLS
Experience the best of in-town living in this recently renovated 4-bedroom, (first floor primary!) 3-full-bath home situated in Downtown Lexington's vibrant East End neighborhood. A standout feature rarely found in this area is the newly built detached 2-car garage with storage loft above, offering exceptional parking, hobby, and storage space with convenient driveway access from Ohio Street. This move-in-ready residence offers style, comfort, and an unbeatable location steps from everything the city has to offer. Inside, the open floor plan creates an inviting flow designed for both everyday living and effortless entertaining. The light-filled living room connects seamlessly to the updated kitchen, where modern finishes and functional design make gathering with family and friends a pleasure. A first-floor primary suite, along with a second bedroom and full bath, provides ample space for family, guests, or roommates. Upstairs find 2 additional bedrooms, full bath and loft area, ideal for work, play or additional lounge space. Step outside to your own private retreat—a fully fenced backyard with patio space perfect for morning coffee, weekend cookouts, or relaxing evenings under the stars. Enjoy being steps from Martine's Pastries, Lyric Theatre, popular restaurants, nightlife, and the energy of Downtown Lexington. This home combines beautifully updated indoor and outdoor spaces, generous garage capacity, and walkable convenience in a highly desirable setting. Updates since 7/2024 include professionally painted interior, Mini-split heating/cooling for second level, electric fireplace, GE Profile washer & dryer, paved designated parking area, detached 2-car garage with loft storage space, wood fence, deck, and landscape lighting.

349 E Third St, Lexington

$375,000
4 Beds 4 Baths 26009813 MLS
Now offering a stunning, historic Queen Anne-style home in downtown Somerset. Built in the 1890s, this iconic residence has been featured on Pulaski County's "Home for the Holidays" tour and showcases timeless character with thoughtful updates. This spacious multi-level home features a grand wood staircase that creates an impressive first impression. Interior highlights include exposed brick, hardwood and tile flooring, recessed lighting, wood ceilings, multiple fireplaces, built-in cabinetry, chandeliers, detailed baseboard trim, wood doors and trim, and a beautiful stained glass window. Natural light fills the home throughout. The eat/in kitchen blends vintage charm with functionality, featuring a working 1952 Chambers gas stove, custom hood, ceramic sink, soapstone countertops, and quality cabinetry. The home sits on a corner lot with fencing and mature trees. A rare rooftop entertaining area offers unique views of downtown Somerset—ideal for relaxing or enjoying local events. The garage features a sink, countertop and a bathroom! There is a brick parking area just outside the garage, a concrete driveway & street parking! The spacious patio has privacy & a nice fire pit. Renovated by skilled craftsmen, the home maintains its historic integrity while offering modern comfort. Conveniently located near downtown amenities, this property is a true community classic. You can enjoy this property on a daily basis plus it's a great place for family & friends to gather. This property has it all - you have got to see this one!

301 W Columbia St, Somerset

$375,000
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

$350,000
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

$349,900
26023992 MLS
Investment Opportunity at 720 Main Street! Looking for a great investment property with income already in place? 720 Main Street offers a unique opportunity with a beautifully renovated two-story brick building featuring a spacious storefront and two 2-bedroom apartments on the second floor. In 2020, the building underwent a major renovation, inside and out, bringing new life to this property while preserving many of its original character features. Improvements include a new roof, HVAC, plumbing, and electrical systems, along with new drywall throughout much of the building. The majority of the original hardwood floors were brought back to their natural beauty, and the impressive tall ceilings were exposed throughout approximately 80% of the building. The large downstairs storefront is currently rented, providing immediate income, while the two upstairs apartments offer additional rental potential. The storefront also features a private, grassed garden area in the back, providing a peaceful outdoor space and a wonderful bonus for the property. With the extensive renovations already completed, there is truly nothing left to do but enjoy the possibilities this property has to offer! 48-hour notice is required for all showings. Don't miss this opportunity to own a beautifully renovated historic-style brick building with multiple income-producing possibilities!

720 Main St St, Paris

$349,000
3 Beds 3 Baths 26024549 MLS
You won't find a home like this again! Priced below its recent appraisal, this rare opportunity offers a sprawling ranch style home with a full basement in the heart of Georgetown. Meticulously maintained, this 3 bedroom, 3 bath home offers an abundance of living space and multiple gathering areas on the main level, including a beautiful oversized sunroom. The main level features a formal dining room, eat-in kitchen, and laundry room with convenient access to the attached two car garage. All three bedrooms offer generously sized closets, while the primary suite includes an additional hall closet that could easily be transformed into a home office, craft room, dressing room, or whatever best fits your lifestyle. The finished basement adds an incredible amount of versatile living space, with endless possibilities for entertaining, hobbies, a home office, and more. Multiple storage closets, utility rooms, and a spacious cedar closet provide plenty of room for organization and storage. The basement bar and large living area creates the perfect spot to gather with family and friends, host celebrations, or unwind at the end of the day. Step outside to a beautiful, flat, fully fenced yard shaded by mature trees. There's plenty of room for kids and pets to play, gardening, outdoor entertaining, or simply enjoying the peaceful surroundings. And if you'd like, the swings can stay too! With its spacious layout, flexible living areas, and convenient Georgetown location, this home is one you won't want to miss!

312 Highland Ave, Georgetown

$330,000
4 Beds 3 Baths 26016656 MLS
Brick home in a great location. Close to downtown area of Lawrenceburg KY. There are many festivals, car shows, concert series in auditorium, restaurants/ coffee, holiday festivities to enjoy nearby. There is also a park & dog park near this home. Swimming pool and large yard for children to play. Upstairs rooms and bonus room perfect for teenagers or family to enjoy their space. Gas logs, hardwood flooring, and oversized garage perfect for those with a sideline business. This home features expansive walk-in closets and abundant storage throughout, making organization effortless. The third floor boasts two versatile bonus rooms, perfect for a home gym, media room, or guest space. With ample room for all your needs, this property offers both comfort and flexibility for a modern lifestyle. Restricted showing times because of home office worker during certain days. Come see this home and make offer.

615 N Main St, Lawrenceburg

$330,000
3 Beds 3 Baths 26009707 MLS
Step into timeless elegance with this early 1900s home where original charm and character have been beautifully preserved. From the moment you enter, you're greeted by stunning hardwood floors, classic wood columns, an impressive staircase, and a one-of-a-kind stained glass window that sets the tone for the entire home. The formal dinning room/office features a cozy gas fireplace, creating the perfect setting for gatherings and entertaining. The kitchen features and island with breakfast bar and seamlessly opens to the living area, highlighted by a striking exposed brick feature wall that adds warmth and rustic appeal. Enjoy indoor-outdoor living with an expansive 8x21 screened-in porch or step out onto the 12x24 deck overlooking a large, private, fenced backyard—ideal for relaxing, entertaining, or hosting summer cookouts. Additional highlights include a waterproofed basement with a lifetime warranty, a sump pump with battery backup, and abundant storage space. This truly one-of-a-kind home offers character, functionality, and charm you simply won't find in newer construction—don't miss your opportunity to make it yours!

357 N 3rd St, Richmond

$329,900
4 Beds 3 Baths 26011358 MLS
Motivated Sellers! Step into timeless charm in the heart of Lancaster, Kentucky! Built in 1899, this stunning 4-bedroom, 3-bath home is filled with character and historic elegance. From the moment you enter, you'll love the open entryway, soaring tall ceilings, beautiful hardwood floors, and unique circular walls that make this home truly one of a kind. The spacious first-floor primary bedroom offers convenience and comfort, while upstairs features three additional bedrooms with plenty of space for family or visitors. Located in the heart of Lancaster, this home combines historic beauty with small-town living. If you're looking for a property with timeless character, classic details, and endless charm, this is a must-see! This home is located 35 miles south of Lexington, KY on US 27, with access to I75 in Madison County just 24 miles away.

217 Lexington St, Lancaster

$329,000
3 Beds 3 Baths 26016625 MLS
Welcome home to this charming historic Georgetown residence offering over 2,500 square feet of living space, full of timeless character and everyday functionality. This spacious 3-bedroom, 2.5-bath home features beautiful hardwood floors and a stunning, oversized sunroom filled with natural light, providing the perfect space to relax, entertain, or enjoy year-round. The first-floor primary suite provides added convenience, while the floored walk-up attic and unfinished basement offer abundant storage. Step outside to enjoy the private, fully fenced backyard with a patio that's perfect for relaxing or entertaining, as well as a detached workshop/storage shed. Conveniently located near downtown Georgetown, parks, schools, shopping, and dining, this home perfectly blends historic charm with modern comfort.

201 Gano Ave, Georgetown

$319,900
3 Beds 3 Baths 26015905 MLS
Beautifully maintained brick townhome offering spacious rooms, timeless finishes, and inviting indoor-outdoor living. Step inside to a bright two-story living room with elegant trim detail, abundant natural light, and a warm, welcoming layout ideal for both everyday living and entertaining. The adjoining kitchen and dining area features white cabinetry, attractive countertops, hardwood flooring, and easy access to the rear courtyard. The home offers generously sized bedrooms, including a large primary suite with excellent wall space, room for a sitting area or home office setup and walk-in closet. Neutral paint, classic crown molding, and thoughtful details throughout provide a clean backdrop ready for the next owner's style. Outside, the private brick courtyard creates a wonderful extension of the living space, perfect for morning coffee, outdoor dining, or relaxing with guests. With its traditional curb appeal, functional floor plan, and desirable blend of comfort and character, this home is ready to enjoy. Currently zoned R-4 Residential with permitted uses including Bed and Breakfast establishment and conditional uses including options for professional office space.

108 Duncan Ave, Paris