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$3,450,000
8 Beds ⋅ 5 Baths ⋅ 25503107 MLS
This is an opportunity for an investor that comes once in a lifetime! Looking for a 1031 exchange? Stop and look here!! 26 Units are available that are in a highly sought out area for rentals. Fully rented with the exception of one rental that will be filled shortly. Beautiful, historic late 1800's early 1900's homes (6 total) that have been used for rentals. Many video tours are attached of the other units, please see video tours. This listing displays 323 High st, the largest of the units. Some of these homes have had a basement apartment added and a few can still have this addition made. Newer apartment (6 unit) and two four plexes ,one triplex building included. These are fast to rent and located in walking distance to EKU, downtown and conveniently located between two I-75 off ramps that are in close proximity. These rental homes also have opportunity for expansion! The rentals included in this sale include 315 High st with 4 bedrooms and a back deck that was completed a year and a half ago (this home has opportunity to expand an apartment underneath the home and a building for rentals can be placed in rear of home). 323 & 327 High st are on the same lot with 323 High st including a very large 6 bedroom home with a back deck, lower 2 bed 2 bath apartment that is rented separate with a separate entrance and back covered patio. 327 High st has a four-plex with four two bedroom two full bath apartments and each unit has a small back yard area or patio. 331 High st is a large 5 bedroom home with a back deck and a 2 bed apartment below that has a covered patio. 335 High st is a large 5 bedroom house with a large back patio, large rooms and a 1 bedroom 1 bath apartment. Behind this house is also a garage that is included with misc doors, windows and other parts usable for rental repairs inside. 337 High st is a fourplex with 4 two bedroom, 2 full bath apartments. Two of those apartments have backyard space. Large parking area in between 323 and 331 high st and the two four-plexes. 335 High st is a 5 bedroom with a back deck and a 1 bedroom apartment below. 337 High st is a six unit apartment building with two three bedroom 2 full bath apartments (one is fully furnished) and 4 two bedroom 1 full bath apartments. All of those units have a back patio and there is a paved parking area in front of the apartment building. 351 High st is a large 5 bedroom home with a back deck and a large yard behind it that may have possibilities for a building to be added behind it and an apartment underneath it. There is off street gravel parking behind this home. 441 Oak st is a 4 bedroom home with a basement, deck was built approx 3 years ago, off street asphalt parking and garage behind the home. 433 Oak st has two four bedroom three full bath units and one three bedroom two full bath unit with a large deck and patio in back. Numerous improvements on these buildings including 3 of the buildings have had new roofs in the last three years, multiple newer HVAC units and improvements. Owner is licensed real estate agent and can answer questions regarding property.

323 High St, Richmond
$1,250,000
6 Beds ⋅ 3 Baths ⋅ 26013972 MLS
Step into one of Lexington's most treasured homes -- a striking Italianate masterpiece with a story as beautiful as its architecture. Built circa 1872 as the official parsonage for Centenary Methodist Episcopal Church, this iconic residence has stood proudly on West Third Street for over 150 years, offering timeless elegance and an irreplaceable sense of presence in the Northside Historic District . Designed with care and craftsmanship attributed to Cincinnatus Shryock, the home features hallmark Italianate elements including tall arched windows, ornate bracketed cornices, and a symmetrical, commanding façade . Inside, soaring ceilings, beveled and leaded glass windows, original hardwood floors, and six fireplaces set the tone for a space that is both stately and warmly livable. Every detail has been lovingly restored or enhanced. The sunroom addition, flooded with natural light, creates a peaceful retreat that flows seamlessly into the designer kitchen--complete with Taj Mahal quartz countertops, custom cabinetry, and elegant brass accents. The bathrooms feature a curated mix of vintage tile, marble finishes, and thoughtful modern updates that preserve the home's character while elevating everyday comfort. Upstairs, a private copper-roofed balcony overlooks a partially fenced backyard filled with mature trees, providing a quiet escape in the heart of downtown. The detached garage, updated zoned HVAC, modern electrical systems, and preserved period millwork offer a rare fusion of historic integrity and present-day convenience. This home's legacy is matched only by its livability. It's walkable to Gratz Park, Jefferson Street dining, and Transylvania University, and is recognized by the Blue Grass Trust for Historic Preservation -- a designation that ensures its beauty and cultural importance will be safeguarded for years to come . More than just a home, 448 West Third Street is a landmark -- lovingly restored, remarkably maintained, and ready to inspire its next chapter.

448 W 3rd St, Lexington
$1,145,000
3 Beds ⋅ 4 Baths ⋅ 26008488 MLS
Awarded the Historic Preservation Comm. Renovation Award, this exceptional circa-1838 Greek Revival residence offers a rare and masterful fusion of historic character and refined modern living. Completely restored down to the studs in 2007, the home showcases timeless architectural elements—exposed brick walls, poplar floors, and six fireplaces (five gas)—beautifully complemented by contemporary design details, including a sleek bridge crafted from glass and reclaimed antique pine. Thoughtfully updated for today's lifestyle, the property features three bedroom suites, including a luxurious primary retreat with a spa-inspired bath complete with double vanities and a fireplace elegantly positioned beside the soaking tub—creating a true sanctuary experience. A secondary primary suite offers its own ensuite bath and fireplace, while a full bath on the main level adds flexibility for guests. The sellers have further enhanced the home by enclosing the former sleeping porch, adding approximately 150 square feet of additional living space, now serving as a light-filled flex room. The gourmet kitchen is appointed with granite countertops, a duel-fuel gas range with vented hood, and generous space for both everyday living and entertaining. Natural light cascades throughout, accentuating the home's elegant proportions and warm, inviting ambiance. Outdoor living is equally compelling, with a spacious & private fenced-in rear patio, a detached two-car garage, and an additional exterior parking space. Zoned B-2A, the property presents unique flexibility in one of downtown Lexington's most desirable and walkable locations. Significant recent seller improvements include three new zoned HVAC systems, a new roof, and two new water heaters. Additionally, the property includes a security system, water softening system, and radon mitigation system, ensuring comfort and peace of mind. As a bonus, the conditioned limestone cellar offers ideal space for a curated wine collection and two air-conditioned attics offer additional storage solutions. Designed for ease of ownership, the property offers a refined lock-and-leave lifestyle ideal for those who travel with confidence and frequency. A truly one-of-a-kind offering—rich in history, elevated in design, and impeccably preserved, this is a rare opportunity to own a distinguished award-winning piece of Lexington while enjoying the best of modern luxury living.

120 E Third St, Lexington
$1,000,000
26006662 MLS
MAJOR PRICE REDUCTION FOR PROPERTY ......................exceptional opportunity to own a significant piece of local history in an incredible location. This property has immense potential: the former Stoner Creek Country Club and Golf Course, spanning 47 acres in a prime, picturesque setting directly on the banks of the historic Stoner Creek. This property offers a rare opportunity for development, preservation, or a new vision. The significant acreage and in-town location make this property a developer's dream. The property is being sold 'as is', giving the new owner flexibility to bring their own vision to life. Don't miss the chance to unlock the full potential of a true Paris icon and down home staple. Options with P and Z approval residential Home , maybe upscale townhomes, city park canoeing as a great option , public restaurant with down home cooking , light industrial ?, Call with your ideas , thoughts will talk with city fathers with your idea,,,, 47 acres,,,,,,,,,,large building dining room , ball room, bar,

38 E Main St, Paris
$980,000
5 Beds ⋅ 5 Baths ⋅ 25500197 MLS
Downtown Lexington income property producing over $103,000 in 2024 and projected to exceed $111,000 in 2025! Built in 2016, this 5-unit multifamily offers modern construction, low maintenance, and strong rental demand in one of Lexington's most desirable areas. Each unit features a 1-bed/1-bath layout with full kitchen and bath — ideal for long-term tenants or short-term rental flexibility. With a 2024 gross income of $103,455 and 2025 projections approaching $111,000, the property delivers an estimated 7% cap rate at the current list price of $1,120,000. All five units are leased, including one performing well as a short-term rental. Tenants love the walkability to Rupp Arena, the University of Kentucky, downtown restaurants, and major employers. Zoned B-2A, this property provides flexibility for mixed use and continued appreciation in the downtown corridor. A true turn-key investment combining reliable cash flow, location, and long-term growth potential. Highlights: • 5 Units | 5 Beds | 5 Baths | 2,772 SF Total | Built 2016 • 2024 Gross Income: $103,455 | 2025 Projected: $111,455 • Estimated NOI: $78,000+ | 7% Cap Rate at $1.12M • Prime Downtown Location — Walk to Rupp & UK • Zoned B-2A | Low-Maintenance Modern Construction

150 Deweese St, Lexington
$945,000
6 Beds ⋅ 5 Baths ⋅ 26007015 MLS
Great Investment Opportunity in the Heart of Downtown- positioned in a prime downtown location, this versatile property offers incredible potential for investors. Currently configured with four residential units zoned R-4, one commercial space zoned B-1, and 6 off street parking spots and 2 car garage, this asset provides immediate income with strong upside for future development. Situated within walking distance to the courthouse, Transylvania University, Sayre School, lots of restaurants, and the vibrant downtown scene, the location is ideal for both residential and commercial tenants seeking convenience and accessibility. The property also features valuable off street parking, a rare and highly desirable amenity in a downtown setting. A great strategic long term hold in a high demand area, this is a unique opportunity worth exploring. Salon: $1290 per month leased until 2027 2 bedroom up $1600 per month (until June 2026) 1 bedroom up $1600 per month (month to month) 1 bedroom down $1600 per month (month to month) efficiency $1100 per month

400-402 N Limestone, Lexington
$925,000
2 Beds ⋅ 2 Baths ⋅ 26012103 MLS
Looking for luxury living in the heart of the Bluegrass? Look no further than The Vine, Lexington's newest and hottest downtown condo community! This 100% move-in-ready unit offers 2 bedrooms (each with its own modern ensuite) along with a premium floor plan, designed to feel open, spacious, and inviting throughout. The thoughtful layout is perfect for entertaining guests, while preparing meals in the chef-inspired kitchen, complete with Sub-Zero and Wolf appliances. Located on the Vine Street side of the building, this unit offers the best views of downtown Lexington. Whether it's through the stunning walls of windows (complete with remote-controlled shades) or from the convenience of your private balcony, you'll get to enjoy one of the best vantage points in the city. Life at The Vine extends far beyond your front door! Ownership offers an unmatched combination of high-end amenities and low-maintenance living, including two designated parking spaces in the covered, parking garage, paid utilities, and access to The Vine Club's resort-worthy amenities—featuring a rooftop lounge and pool, luxury spa services, fine dining at The V at The Vine restaurant, and more! Residents also enjoy concierge-style services, including a doorman, building security, and a professionally managed short-term rental program. Conveniently located just minutes from Rupp Arena, University of Kentucky, and many of the area's top dining, entertainment, and nightlife destinations, The Vine offers more than just a mere change of address—it's an entire lifestyle upgrade.

106 W Vine St Unit 409, Lexington
$850,000
26009467 MLS
Operated over 13 years as successful nightclub/bar, this is a fully sprinklered and well maintained building with ample electric, tankless gas water heater, large 2 story patio, occupancy of 392 total. 4692 sf per appraisal, 4624 per PVA, was used as a retail business most recently. 4 total public restrooms and 1 private staff rr. Previously 1 bar per floor total 2 fully plumbed and set up. B-2-B zoning allows a large number of uses including residential/apt/condo etc. Privately owned parking lot around building allows monthly, daily, hourly pay parking. Disclosure - LA/Broker is member/manager of LLC that owns the property. Property is being sold as is.

208 S Limestone, Lexington
$820,000
4 Beds ⋅ 3 Baths ⋅ 26016428 MLS
American Gothic beauty in the heart of horse country in storybook, Midway Kentucky. This ICONIC home on 2acres sits across from the Holly Hill Inn and 2mins from Hallmark Movie quaint downtown Midway. Updated for modern living blending the historic with thoughtful updating. Open floor plan with spacious great room, gourmet kitchen and butler's pantry. Soaring ceilings with floor to ceiling windows that flood the space with soft natural light filtered through the old growth trees. Original heart pine floors beautifully preserved and many original features remain throughout the home. Full bath and a bedroom on the 1st floor. Primary suite on the 2nd floor with tile shower and large bath. Second en-suite bedroom on the 2nd floor. Copper gutters and copper roof on the seamless side porch addition. The barn is converted to a 3-car garage with tons of extra storage above. Tucked behind the garage is an 1800 sq. ft auxiliary building currently used as a wood shop. The building with covered porch and full bathroom offers enormous upside potential for whatever your dreams or hobbies are made of. Don't miss this rare opportunity to own a piece of Midway's history.

425 N Winter St, Midway
$814,800
4 Beds ⋅ 2 Baths ⋅ 26008044 MLS
3.52 acres, fully renovated home - A rare find indeed with - usable land, updated living space and walkable access to everything Midway has to offer. The main home offers over 3200 sq ft with a layout designed for both everyday living and gathering. The updated kitchen includes granite countertops, gas range, pot filler, built in dishwasher and refrigerator, opening into a comfortable fireside sitting area. Multiple living spaces create a natural flow, making the home feel both connected and functional. The home includes 4 bedroom and 2 full bathrooms and an office, providing flexibility based on your level needs. A main-level bedroom and full bath offer added convenience for guests or single level living. Above the detached three-bay garage is a fully equipped 878 sq ft apartment with its own kitchen and laundry - ideal for guests, extended family or additional living space. ( not included in listing sq ft ) One garage bay is currently used an a workshop. The 3.52 acre property is partially wooded, with many native trees planted and landscaping designed to support pollinators and local bird population. A large front porch provides a place to take in the sunset, while outdoor spaces - including the fire pit area - offer opportunities to enjoy the property throughout the seasons. A well maintained chicken coop adds to the usability of the land. No roosters allowed per City Ordinances. Located just across from Walter Bradley walking trail, this home provides direct access to Midway's trail system, connecting you to local restaurants, shops, the dog park and nearby school. The home was fully renovated 3 years ago, bringing together modern updates with a setting that is increasingly difficult to find. Shown by appointment only. Security and cameras on site. OPEN HOUSE SAT MAY 23rd 2026 NOON to 3 PM

314 N Winter St, Midway
$787,000
4 Beds ⋅ 3 Baths ⋅ 26008238 MLS
Restored Italianate historic home on 1+ acre. Approx. 3400 sq.ft. with a separate guest house with approx. 800 sq.ft. in historic Downtown, Versailles. Convenient to downtown shops and retail. Beautiful high ceilings and impressive woodwork. Lots of sunlight with open concept. Hardwood floors, ceiling to floor windows make this an exceptional home. Over and acre right in the middle of town on the lovely South Main Street. The home is set off the road a bit to offer privacy and a picturesque area to stroll about. There is also a quaint guest house that can be used as an office or home business complete with kitchen, bedroom and full bath.

305 S Main St, Versailles
$765,000
25014933 MLS
Own a piece of Danville's vibrant and historic downtown with this stunning three-story commercial property. 303 W Main St showcases classic architectural charm and modern functionality in a beautifully maintained historic building. The first floor is home to the highly regarded Copper and Oak Restaurant, a local favorite known for its upscale atmosphere and strong customer base. The second floor features their private banquet room, ideal for events and gatherings, plus a private office; a chair lift is in place for accessibility. The first and second floor are approximately 4,038 square feet. On the third floor, you'll find a fully refurbished apartment, thoughtfully updated for comfort while maintaining its historic character. Whether used as a long-term rental or a short-term Airbnb, this space is perfect for those who want to enjoy downtown living at its finest—just steps away from dining, shopping, and entertainment. As an added benefit, Copper and Oak is open to continuing their lease with the new owner, offering immediate rental income and a seamless investment transition. Don't miss this unique opportunity!

303 W Main St, Danville
$625,000
5 Beds ⋅ 3 Baths ⋅ 26012986 MLS
Beautifully updated historic home in the heart of downtown Lexington, just steps from restaurants, coffee shops, the Farmers Market, Rupp Arena, and more. This 4-bedroom, 2-bath home is filled with character, featuring 6 fireplaces, abundant natural light, freshly painted interior throughout, and thoughtfully preserved historic details. Enjoy slow mornings and evenings with neighbors from the home's spacious front porch—a hallmark of classic downtown living. The kitchen offers granite countertops, while the spacious primary bath features a dual vanity and walk-in tiled shower. A bright sunroom provides the perfect space for a home office, reading room, or additional living area. Detached 2-car garage includes a fully finished accessory dwelling unit (ADU) with a bedroom, full bath, kitchenette area, and ample storage—ideal for guests, a private workspace, multigenerational living, or potential rental income. Outside, enjoy a beautifully landscaped, low-maintenance backyard oasis complete with private patio and porch spaces designed for relaxing and entertaining. Rarely does a downtown home offer this combination of historic charm, modern updates, outdoor living, off-street parking, and a finished ADU. Located at the corner of Johnson Ave you still get that neighborhood feel with park access at the end of the street! Experience the best of downtown Lexington living at 125 East Fourth Street.

125 E Fourth St, Lexington
$615,000
5 Beds ⋅ 3 Baths ⋅ 25507796 MLS
Beautiful 1895 Historic Home in Woodward Heights Historic District - 3 Separate Apartments - 3,109 Sq Ft. This stunning property offers the potential for an Airbnb or conversion back to a single-family home, allowing for flexibility in how you choose to use the space. Each apartment features its own private entrance, kitchen, full bathroom living area and a common laundry room for long-term tenants, or multi-generational living. Historic details such as tall ceilings, original wood flooring and woodwork, and large windows create a warm, inviting atmosphere in every unit. The property is conveniently located within walking distance to Rupp Arena, Gatton Park, downtown dining and shopping as well as with the University of Kentucky and Transylvania University. It also includes a unique backyard with brick paving which is perfect for outdoor relaxation or entertaining family and guests! Whether you continue as a profitable rental operation or reimagine for personal use, this property offers unlimited potential in a prime setting.

311 Madison Pl, Lexington
$535,000
3 Beds ⋅ 4 Baths ⋅ 26012118 MLS
Distillery Heights — downtown Lexington's most sought-after luxury townhome community. Sleek industrial design. Unbeatable location at Manchester Street and Oliver Lewis Way in the heart of the Distillery District. Walkable to top restaurants, boutique shopping, and premier event venues. Steps away, Gatton Park on the Town Branch — where designers uncovered and restored the historic Town Branch stream, buried underground since the 1930s, and transformed a parking lot into an 11-acre world-class park. It's Lexington history, literally brought back to the surface. This 3-bed, 3.5-bath townhome gives every bedroom its own private en-suite. Attached 2-car garage. Second floor open-concept kitchen and living area with quartz countertops, stainless appliances, oversized island, and private deck. Third floor primary suite with walk-in tile shower, dedicated laundry, and guest bedroom with full bath. Short-term rentals allowed — and this unit is already performing at $600 per night on Airbnb.

955 Tarr Trce Unit 2109, Lexington
$519,000
4 Beds ⋅ 4 Baths ⋅ 26010347 MLS
Set on 2.66 acres, 1005 E Adair offers a quiet country lifestyle without sacrificing modern convenience. This 4-bedroom, 3.5-bathroom home is designed for those who value room to breathe, both inside and out. The Main Living Area The heart of the home features an open-concept layout that connects the kitchen, dining, and living areas. Large windows throughout the home frame the surrounding landscape, filling the rooms with natural light and creating an easy, inviting flow for everyday life or hosting friends. Flexible Lower Level The finished basement adds significant living space and versatility to the home. It's an ideal setup for a home gym, guest quarters, or a hobby hub. One of the standout features is a dedicated space that is perfectly set up for a theater room, giving you the footprint to create your own ultimate movie-night retreat. Thoughtful Functionality The home is built to handle a busy household with ease. You'll find two laundry rooms for added convenience and an abundance of storage tucked away throughout the floor plan, ensuring everything has its place. The Great Outdoors Step onto the covered back porch to take in the privacy of the expansive backyard. With over two and a half acres to work with, there is plenty of room for gardening, outdoor entertaining, or simply enjoying the peaceful views. 1005 E Adair offers the rare combination of acreage, functional design, and room to grow. Schedule your private showing today to see the potential for yourself.

1005 E Adair St, Owenton
$497,900
2 Beds ⋅ 2 Baths ⋅ 26008234 MLS
Tucked away on 1.8+ private acres, this secluded retreat offers a rare blend of space, versatility, natural light and beauty. The property includes a 1,900+ sq. ft. main residence and an expansive 2,200+ sq. ft. free-span garage/workshop, ideal for a variety of uses. Property backs to the Big Springs Park, you'll enjoy peaceful, scenic surroundings right in your backyard. Recent upgrades, 2025 HVAC system, 2025 Metal Roof (Standing Seam), total crawlspace encapsulation, Large composite deck, updated gutters, new skylights, a new garage door and opener. Inside, the home features an open-concept layout designed for entertaining, highlighted by vaulted ceilings and hardwood floors. The custom kitchen is built for both function and style, featuring a commercial-grade 6-burner Viking range, center island, and plenty of cabinet space. The primary suite offers vaulted ceilings, direct deck access, and walk in shower! A second bedroom includes en-suite access to the hall bath, and both bedrooms feature spacious walk-in closets. The oversized garage/workshop provides endless potential—enjoy all your hobbies and adventures. The garage has a drain, multiple fans, speakers ect. The cleared side yard offers additional space for gardening, landscaping, or even a pool. The fenced area is perfect for pets to come in and out on their own free choice. The location is ideal for being in the heart of Versailles but being a private sanctuary. Property is located behind Clarks Funeral Home, where admin offices are located and some services can be held. Private road marked with stripes.

237 Rose Hill Ave, Versailles
$495,000
3 Beds ⋅ 2 Baths ⋅ 26006827 MLS
Charming Craftsman-style home circa 1919, thoughtfully restored to blend timeless character with modern convenience, ideally located in downtown Lexington. This 3-bedroom, 2 full bath home showcases newly refinished hardwood floors and a fully renovated interior designed for today's lifestyle. The chef's kitchen features quartz countertops, custom cabinetry, and a 6-burner gas range-perfect for both everyday living and entertaining. Both bathrooms have been tastefully updated with quality finishes while maintaining historical features. The functional layout offers bright, inviting living spaces while preserving original charm and architectural detail. Enjoy the welcoming front porch, a charming back patio ideal for outdoor gatherings, and the convenience of a detached one-car garage. A rare opportunity to own a move-in ready historic home with thoughtful updates in one of Lexington's most desirable downtown locations.

450 N, Lexington
$495,000
5 Beds ⋅ 4 Baths ⋅ 26008786 MLS
Rarely available waterfront property in Paris, KY -- This Executive level home provides a Very Quiet & Private location on Stoner Creek. Yet, this park - like setting, is only minutes from downtown Paris, which has a walkable Main Street with numerous shopping, dining and cultural options. The elevated front entrance leads to a beautiful stone fireplace (w/ gas logs) that anchors the vaulted central living area. A split bedroom floor plan on the main level, including two en suite bedrooms (one with direct access to the covered rear porch). Additional bedrooms and living area are located on the second floor. From the home's main level, there are multiple doorways to over 1,000 sf of covered, porches that are perfect for summer lounging and entertaining. The rear, covered porch leads to an additional elevated deck and ground level patio areas that overlook the water and lead to the private dock. The on - grade, full 'basement' / garage offers access to the home's elevator (which serves all floors -- offering convenience for stocking the kitchen pantry or planning for the long - term, should mobility issues arise), a workshop / storage space, and parking for 5 cars (+). Additional garage features include 50 amp EV charging, RV hookups (water, electric & sewer). The expansive driveway provides ample off - street parking for visitors / RV's / etc. Numerous, recent upgrades include: roof; kitchen granite & wood countertops; 36" gas cooktop; dishwasher; microwave; renovated laundry room, pantry - hall and guest en suite; hardwood floors; LED lighting; interior paint and all exterior porches, decks & stairs re-stained. Currently, bedroom #5 is utilized as a home office. A 'Sweetwater' pontoon (w/ 60 hp Yamaha) is tied up at the dock and available as well. In the Paris real estate market, this could truly be a once in a lifetime opportunity.

129 Taylor Ave, Paris
$490,000
3 Beds ⋅ 4 Baths ⋅ 26007428 MLS
OPEN HOUSE SATURDAY, JUNE 13TH 12-2PM! Welcome to modern downtown living at its finest on Maryland Avenue. Built in 2020, this beautifully appointed townhouse offers 3 spacious bedrooms and 3.5 bathrooms, thoughtfully designed for both comfort and style. As the original builder's model, this home stands apart with premium upgrades and elevated finishes throughout—including rich engineered wood flooring that adds warmth and sophistication to the main living spaces. The open-concept layout is ideal for entertaining, featuring a sleek, contemporary kitchen with high-quality fixtures, modern cabinetry, and seamless flow into the living and dining areas. Each bedroom offers privacy and convenience with its own en-suite bath, while the additional half bath is perfect for guests. A rare two-car garage provides secure parking and valuable storage—an exceptional feature for downtown living. Located just steps from the energy of downtown Lexington, you'll enjoy easy access to dining, shopping, and entertainment, all while coming home to a quiet, refined retreat. This is low-maintenance luxury with thoughtful upgrades you won't find in neighboring units—don't miss your opportunity to own one of the most desirable townhomes on Maryland Avenue.

516 Maryland Ave Unit 128, Lexington
$489,000
4 Beds ⋅ 3 Baths ⋅ 26009628 MLS
Introducing this timeless, historic showpiece with the comfort of modern living, welcome to 342 N. Main! This stunning Queen Anne residence is perfectly situated on a spacious lot in the heart of downtown Harrodsburg, blending charm, convenience, and everyday functionality. With over 4,500 square feet, the home is rich in character—featuring intricate woodwork and built-ins, a striking carved staircase, beautiful stained glass, gleaming hardwood floors, soaring ceilings, and classic clawfoot tubs. The layout includes 4 bedrooms and 3 full bathrooms, highlighted by a generous first-floor primary suite complete with a beautifully updated bath and walk-in closet. Designed for both daily living and entertaining, the home offers a spacious eat-in kitchen with a brand new double oven gas range and 2 drawer dishwasher. A first-floor laundry with folding area, and a seamless mix of formal and casual living spaces. Step outside to enjoy the inviting covered front porch, or unwind on the back patio overlooking the expansive backyard, complete with mature trees and established landscaping. Additional features include a detached garage and large driveway, providing tons of parking and convenience.

342 N Main St, Harrodsburg
$485,000
4 Beds ⋅ 3 Baths ⋅ 26004913 MLS
Timeless Charm Meets Modern Updates in the Heart of Shelbyville Welcome to 601 Brown Avenue — where classic character and thoughtful modern improvements come together beautifully. Located on one of Shelbyville's most desirable streets, this stunning home offers the perfect blend of historic charm and updated comfort. From the moment you arrive, you'll appreciate the home's inviting presence and architectural details that showcase its timeless appeal. Inside, you'll find spacious living areas filled with natural light, distinctive character, and tasteful updates that complement the home's original beauty. Modern enhancements provide today's convenience while preserving the warmth and craftsmanship that make this property truly special.

601 Brown Ave, Shelbyville
$485,000
4 Beds ⋅ 3 Baths ⋅ 26005969 MLS
Tucked away on a quiet court adjoining Berea Country Club, this one-of-a-kind property offers the perfect blend of privacy, space, and convenience, just minutes from town while still feeling like a private retreat. With only one other home on the street, you will enjoy a rare sense of seclusion and peaceful surroundings. Wake up to breathtaking sunrises and take in the views from multiple expansive decks or unwind year-round in the light-filled sunroom. This VERY spacious home was designed for both comfort and flexibility, offering room to spread out, entertain, and truly live. A standout feature is the fully equipped home gym complete with a sauna, all of which stays, making it easy to prioritize wellness without ever leaving home. The property also includes a separate garage and workshop area, perfect for hobbies, storage, or additional workspace. The primary suite is a true escape, featuring a large bathroom and generous walk-in closet. Downstairs, the walk-out basement offers even more living space with two additional bedrooms and a full bath, ideal for guests, multi-generational living, or added privacy. If you have been searching for something unique, spacious, and private, with unbeatable proximity to Berea, this is the one. 48 hour kick out in place.

106 Churchill Ct, Berea
$485,000
1 Baths ⋅ 26008729 MLS
Mixed-use commercial opportunity with income potential in a high-visibility location just minutes from I-64. This versatile property offers a fully equipped commercial space currently operating as a bakery, complete with kitchen area, service counter, dining/event space, drive-thru window, outdoor seating, and on-site parking. Attached to the commercial space is a private-entry apartment, ideal for rental income, owner occupancy, or employee housing. An additional unfinished area already plumbed for a second one-bedroom apartment provides future expansion and added investment potential. With strong traffic exposure along the bypass and flexible layout options, this property could accommodate a variety of uses including café, bakery, restaurant, retail, office, or other service-based businesses. Excellent opportunity for an owner-operator, investor, or entrepreneur looking for a live/work setup or multi-income property. Business is not included in the sale. Select equipment may be negotiable.

808 Bypass Rd, Winchester
$470,000
3 Beds ⋅ 4 Baths ⋅ 26008120 MLS
Welcome to this beautiful 3 bedroom, 3.5 bathroom townhome in the heart of Downtown Lexington. The walkability is unmatched for downtown living with excellent access to restaurants on Jefferson street, the new Gatton Park and Rupp Arena. This home has not one, but 2 outdoor spaces! The lower level of the townhome features a bedroom and bath with access to the garage and a perfectly landscaped fenced backyard patio. There are high ceilings throughout the home and beautiful engineered hardwood in the main living areas. On the second level is a spacious and open concept kitchen, dining and living room area. The living room has built-in bookshelves and an electric fireplace. The well-appointed kitchen has newer appliances, marble countertops and a large dining area. Finally a balcony out the front with plenty of space to relax and hang out and a Juliet Balcony next to the kitchen. On the third level there are 2 more large bedrooms with en-suite bathrooms including a large walk-in shower in the primary suite. Large windows throughout the home provide the space with natural light. There is plenty of storage and ample closets. Enjoy this gated, downtown community with all this move-in ready townhome has to offer!

512 Maryland Ave Unit 112, Lexington
$470,000
2 Beds ⋅ 2 Baths ⋅ 26004206 MLS
Stunning Condo experiencing the best of Downtown Lexington in the highly desirable Field & Main building featuring 18 units with secure building entrance, reserved parking spaces, rooftop club space and space outdoor deck for relaxing or entertaining, located on the 5th floor with views of Thoroughbred Park this 2 bedroom 2 full bath condo offers the finest finishes and amenities including tall ceilings numerous upgrades throughout. Convenient to all of downtown Lexington's finest as well as the University of KY and much more. Don't miss this special opportunity!!

369 E Main St Unit 402, Lexington
$460,000
2 Beds ⋅ 2 Baths ⋅ 26019161 MLS
Experience the best of downtown Lexington living in this stunning condo, ideally located within the highly desirable Field & Main building. This boutique building features just 18 units, a secure entrance, reserved parking, and a shared rooftop club space with an outdoor deck — perfect for relaxing or entertaining with skyline views. Situated on the third floor, this beautifully appointed 2-bedroom, 2-full-bath condo impresses with soaring 9-foot ceilings and the finest finishes throughout. Numerous thoughtful upgrades elevate every space, offering a rare blend of comfort and style in the city's core. Enjoy unbeatable convenience to downtown Lexington's best restaurants, shops, and entertainment, plus easy access to the University of Kentucky. Opportunities like this don't come often — schedule your showing today!

369 E Main St Unit 302, Lexington
$450,000
2 Beds ⋅ 3 Baths ⋅ 26008189 MLS
Experience the best of downtown Lexington living just in time for spring and summer, where festivals, live music, and vibrant city energy are right outside your door. Overlooking Triangle Park and West Main Street, this top-floor condo offers a front-row seat to outdoor events, patio dining, and the city's most exciting seasonal attractions. Welcome to this top-floor, fully furnished luxury condo located inside the Hilton Lexington Downtown the only condo of its kind in downtown Lexington. Everything you see stays just bring your suitcase and start enjoying the lifestyle. From your windows, take in sweeping views of Triangle Park/Gatton Park and West Main Street, along with one of the best vantage points in the city for Fourth of July fireworks. Inside, the open-concept layout features soaring ceilings, elegant finishes, automated remote blinds, and custom drapery by My Favorite Things. Recent updates include a renovated primary bathroom with walk-in shower, three new commercial-grade backflow toilets, interior window seal replacements, and fresh trim paint throughout. This residence flexes to fit your lifestyle whether it's a weekend retreat, a Game Day headquarters, a second home, or a full-time urban residence. Enjoy full access to Hilton amenities, including a pool, hot tub, fitness center, and on-site bar and restaurant plus the added convenience of room service delivering food and drinks directly to your door. Step outside and walk to Rupp Arena and the Lexington Opera House for concerts, comedy, and year-round entertainment. Spend your time at the newly opened Gatton Park, featuring green space, water features, walking trails, and community events all just steps away. Offered fully furnished everything stays, from the dishes and bedding to the bourbon. Experience downtown Lexington at its peak. Schedule your private showing today. Go CATS! Starting April 17th: BLOOM by the French art and design collective TILT brings vibrant, oversized peony bouquets to Gatton Park this spring. Towering more than 20 feet high, the blooms reach skyward in an awe-inspiring tribute to nature. Join us for Opening Night on April 17 at 6:00 pm as the park comes to life with dynamic, color-changing light, alongside live performances, a local artisan market, a community art project, and more.

345 W Vine St Unit 2202, Lexington
$450,000
4 Beds ⋅ 3 Baths ⋅ 26011180 MLS
Welcome to 450 Oak Street in Downtown Richmond, KY — a beautifully preserved and updated historic home built in 1898 offering approximately 3,675 finished square feet, 4 bedrooms, 3 full bathrooms, and a location just one block from Eastern Kentucky University. Situated on a 0.24-acre corner lot, this property blends original architectural character with modern renovations and expanded living spaces in one of Richmond's most recognizable historic corridors. The main level retains much of the home's original design and craftsmanship, featuring a formal foyer, formal living room, and formal dining room with spacious layouts ideal for entertaining and everyday use. Wood flooring carries throughout much of the home, adding warmth and continuity between living spaces. A fully renovated kitchen serves as the centerpiece of the home and includes new cabinetry, quartz countertops, stainless steel appliances, tiled backsplash, and wood flooring. Adjacent to the kitchen is an eat-in dining area plus a spacious family room/den, creating additional casual living space beyond the formal rooms. The main level also includes a full bathroom and dedicated laundry room for added convenience. Upstairs, the home offers four bedrooms including a spacious primary ensuite complete with a walk-in closet, dual sinks, jetted soaking tub, and tiled walk-in shower with glass door. The primary suite also features private access to a Trex deck, creating an elevated outdoor space overlooking the property. An additional updated full bathroom serves the remaining upstairs bedrooms. Outdoor living areas include a welcoming screened-in porch, corner lot positioning, and mature surroundings consistent with the historic downtown Richmond setting. The home's combination of preserved character, modern kitchen and bath updates, flexible living areas, and proximity to EKU make it a unique opportunity in the Richmond market. Located near downtown Richmond dining, shopping, local businesses, and campus amenities, 450 Oak Street offers historic architecture, updated interiors, and a highly accessible location close to one of the city's most recognized landmarks. 48 Hour Kick Out Clause in place as of 5/27/2026.

450 Oak St, Richmond
$445,000
12 Beds ⋅ 8 Baths ⋅ 26008162 MLS

125-131 Bradford Dr, Paris