Lexington Real Estate | Lexington Historical Properties for Sale

INVESTOR OPPORTUNITY in Downtown Lexington! Potential for a package sale of 3 properties (353 Ohio Street and 347 Ohio Street) for $350,000, offering excellent potential for renovation, rental income, resale, or long-term investment. Properties are being sold AS-IS and offer an opportunity for investors, renovators, or buyers looking to add value.

436 Ohio St, Lexington

$315,000

3 Beds ⋅ 1 Baths ⋅ 26023779 MLS

A beautifully updated century-old Craftsman home blending original character with thoughtfully renovated modern finishes. Original pine hardwood floors have been beautifully refinished throughout, complementing the distinctive Craftsman staircase and architectural character. The main level offers a convenient semi-open layout connecting the living room, dining area and renovated kitchen. The kitchen features custom white shaker cabinetry, granite countertops, open shelving, stainless steel appliances with gas range, a spacious peninsula with seating for three, an island with integrated double trash bins, and a walk-in pantry offering excellent additional storage. The living room features a custom faux-limewashed decorative fireplace that creates a striking focal point, along with a TV-ready setup with mounting anchors already installed. The completely renovated first-floor bath includes a deep tub/shower combination, new floor and shower tile, quartz-topped vanity, brushed-gold accents and a floor-to-ceiling storage niche. Washer and dryer are also included. Three bedrooms include one on the main level and two upstairs, providing flexibility for guests, home office or a variety of living arrangements. An upstairs hall alcove area provides additional bonus space and future potential. Outside, a large covered front porch welcomes you home, while the lush backyard offers a surprisingly private retreat with no residential property directly behind the home. The nearly fully fenced yard includes a patio ideal for grilling and entertaining, a dedicated fire-pit area, and a beautiful pink dogwood that creates a canopy of vibrant blossoms each spring. And if that's not enough, a detached two-car garage offers covered parking and excellent workshop potential, along with a 10' x 10' storage shed providing additional storage. Positioned at the Versailles Road end of Woodford Drive, the first home on the right when entering from Versailles Road, the property has only one residential property immediately adjoining it, with church property bordering the other side and rear. The location also provides quick access to Versailles Road and convenient access to downtown Lexington, Rupp Arena, the Manchester Street corridor and Blue Grass Airport. A wonderful opportunity to own a home that combines historic Craftsman character with modern updates, thoughtful functionality, abundant storage and inviting outdoor spaces.

102 Woodford Dr, Lexington

$344,900

4 Beds ⋅ 2 Baths ⋅ 26023770 MLS

Investors and owner-occupants alike will appreciate the versatility and rental potential of this property, especially with the separate upstairs living space and prime location near Downtown Lexington. A new roof and gutters were installed in 2026, per the seller. This recently updated home is just minutes from Greyline Station, Rupp Arena, and all that Downtown Lexington has to offer. The main level has everything you need, including 2 bedrooms, 1 full bath, a separate utility room plus a beautifully renovated kitchen featuring stainless steel appliances, a gas range, quartz countertops and more. Upstairs, you'll find a separate living space with kitchenette and full bath, along with 2 additional bedrooms- a setup that could work wonderfully as a rental or in-law suite with its separate entrance, or additional private living space. And don't miss the large backyard- a shady, private oasis that's hard to find this close to downtown! With historic charm, functional living spaces, potential income opportunities, and a location close to dining, entertainment, shopping, and downtown attractions, this property offers so many possibilities and plenty of potential. Don't miss it!

223 E Loudon Ave, Lexington

$250,000

4 Beds ⋅ 2 Baths ⋅ 26023590 MLS

This spacious 4-bedroom, 2-bath ranch is a fantastic opportunity for investors, the property is Zoned for a multi-family, R2. Or first-time home buyers ready to make it their own. The functional layout offers two separate den areas, ceiling fans throughout, and a fully equipped kitchen with included appliances. Brand new air unit installed, updated electric panel, renovated three years ago. Outside, you'll find a large, partially fenced yard and a detached carport for added convenience and storage. The home shows typical wear from previous tenants but is priced to allow for cosmetic updates and instant equity potential. A solid value in a super convenient location. Don't miss it!

1177 Jones Trl, Lexington

$899,000

5 Beds ⋅ 4 Baths ⋅ 26023535 MLS

Step into a remarkable piece of Lexington's history with this exquisitely restored Federalist-style residence located in the Historic South Hill Neighborhood, part of the James Lemon Rowhouses, built in 1812 and proudly listed on the National Register of Historic Places. This home was originally owned by James Lemon, a native of Ireland, Revolutionary War veteran who was very entrepreneurial, he was a tailor, brick yard owner, and farmer who settled in Fayette County in the early 1800s. In 1825, Lemon hosted the famed Marquis de Lafayette in this very home during his celebrated visit to Lexington--forever tying this residence to the city's historic fabric. While deeply rooted in heritage, the home's recent transformation by Greystone Construction brings it gracefully into the modern era. The chef's kitchen features custom cabinetry, quartz countertops, top-of-the-line appliances, and premium finishes, blending the warmth of history with contemporary sophistication. Both bathrooms have been completely redesigned--the primary suite now includes a custom walk-in tile shower, luxurious soaking tub, designer vanities, and a private laundry room conveniently attached. The guest bath offers its own custom walk-in shower, high-end fixtures, and elegant detailing that echo the home's refined aesthetic. The primary ensuite serves as a luxurious retreat with a coffee and champagne bar, comfortable sitting area, and thoughtful modern touches, including an automated recessed television and motorized window shades--a seamless blend of indulgence and innovation. With two laundry areas and a well-designed layout, the home effortlessly balances historic charm with modern functionality. Enjoy Lexington's beautiful seasons from the covered porches on both the first and second levels, perfect for relaxing mornings or entertaining evenings. Located just steps from downtown's premier restaurants, shops, and cultural destinations, this extraordinary property represents the best of both worlds--a rare fusion of historical prestige and modern luxury in one of Lexington's most storied neighborhoods.

331 S Mill St, Lexington

$899,900

3 Beds ⋅ 3 Baths ⋅ 26023112 MLS

Set in Lexington's beloved Fairway neighborhood, this charming stone home beautifully blends classic character with thoughtful updates and inviting spaces. A timeless tile roof and mature boxwoods frame the entry, creating an unforgettable first impression. Inside, the foyer opens to both the dining room and family room. You will love the 9 foot ceilings and original hardwood floors throughout the main level. The family room features an original fireplace and adjacent sitting area with built-ins, offering the flexibility to serve as a playroom, or home office. Generously sized, the dining room is ready for everything from weeknight dinners to big family gatherings. The kitchen features inset cabinetry with granite countertops, stainless steel appliances, and fantastic natural light with windows overlooking the private backyard. At the back entry, a dry bar with wine storage and a beverage refrigerator adds both function and style. Upstairs, the primary bedroom offers beautiful built-ins for both storage and display, along with a private en-suite bath. Two additional bedrooms share a hall bath with a combination tub/shower. Outside, the backyard features a large patio and mature trees—perfect for relaxed evenings and outdoor entertaining. The extended one-car garage offers a great deal of additional storage space for bikes and outdoor equipment. With its original details, abundant natural light, and coveted Fairway address, this special home offers the perfect combination of timeless Lexington charm and comfortable everyday living.

222 Kingsway Dr, Lexington

$297,000

4 Beds ⋅ 4 Baths ⋅ 26022798 MLS

Completely reimagined from top to bottom, 443 Morgan Avenue offers the perfect blend of charm and modern convenience! This spacious 4-bedroom, 3.5-bath home boasts 2,054 sq. ft. of thoughtfully renovated living space. You'll love the gleaming new hardwood floors and open-concept layout that flows effortlessly from room to room. The brand new kitchen features butcher block countertops, stylish cabinetry, and new Frigidaire appliances including a smooth-top electric range and stackable washer/dryer (mud room w/sink). Major upgrades include a new HVAC system, new plumbing throughout, new 200-amp electric panel and new wiring throughout, new bathrooms, new outlets and fixtures, new vinyl siding, new drywall throughout and fresh interior paint, new tankless water heater, new energy-efficient windows and new insulation throughout including new spray foam insulation in crawlspace, ensuring comfort and efficiency. Step outside to enjoy both a welcoming front porch and a new covered back deck, ideal for relaxing or entertaining. This move-in-ready home is a rare gem in a convenient Lexington location!. Virtually everything is new in this home, all it needs now is a new homeowner! See Seller's Disclosure for a more detailed list of updates!

443 Morgan Ave, Lexington

$359,000

2 Beds ⋅ 2 Baths ⋅ 26022786 MLS

Price correction on this beautiful Kenwick home. In one of Lexington's most beloved and walkable communities, 101 year old home lives like new. Some original hardwood flooring has been lovingly restored, adding warmth and character you can't replicate with new construction. Meanwhile, the attic level of the home was thoughtfully opened up in the style of a loft. The loft is finished with the ability to provide flexible space. Downstairs, a newly sealed basement provides clean, dry storage and laundry. Outside, the garage/workshop opens the door to real possibility?personal office, a true garage/workshop setup, or an accessory dwelling unit for rental income.In a neighborhood where nearly half of homes are rentals, this flexible bonus space is a genuine differentiator, whether you're planning to live here or invest here. With major systems replaced, restored original character, and a workshop built for whatever you need next, 377 Preston Ave offers a rare combination in Kenwick: low-maintenance peace of mind with room to grow.

377 Preston Ave, Lexington

$169,900

3 Beds ⋅ 1 Baths ⋅ 26022756 MLS

This 3-bedroom, 1-bath house offers a functional layout and plenty of potential for the buyer looking to build equity, make improvements, or add a property to their rental portfolio. The central location makes this property attractive for both owner occupancy and investment purposes.

457 Breckenridge St, Lexington

$340,000

3 Beds ⋅ 2 Baths ⋅ 26022483 MLS

Turnkey and move-in ready! This beautifully renovated and thoughtfully expanded 3-bedroom, 2-bath home offers 1,262 sq. ft. of finished living space with fresh, modern finishes throughout. Extensive updates include a new HVAC system, windows, plumbing, cabinetry, quartz countertops, laminate flooring, tile showers, and updated drywall and ceilings. The newly finished upper level adds valuable living space with an additional bedroom and full bath. From the moment you move in, the work has already been done, simply unpack and enjoy. The bright, refreshed interior offers a functional layout with stylish finishes throughout, while the encapsulated basement features water-management improvements for added peace of mind. Outside, you'll find a newly paved driveway with parking spaces. The fenced in backyard offers plenty of space for entertaining, pets, gardening, or relaxing at home. With three bedrooms, two full baths, a basement, fenced yard, and extensive improvements inside and out, this truly turnkey property offers the opportunity to move in and enjoy your new home from day one!

194 Rosemont, Lexington

$489,000

4 Beds ⋅ 3 Baths ⋅ 26022573 MLS

Super sharp Craftsman style 3 Br, 2 bath ranch in the desirable Bell CT area within walking distance to National Avenue, UK, downtown, restaurants, parks, shopping and more. A multi windowed sun porch welcomes you into the open great room and completely renovated kitchen, 3 large bedrooms and 2 full baths complete the 1st level. The 1320 sf unfinished basement is an excellent storage and flex space. There is a large 2 car detached garage with a spacious 1 BR, 1 bath apartment above. Great for rental, office or guests! Combined square footage of main house (1696sf) and apartment (576sf) is 2272 SF. Other features include new roof, side patio, large parking pad and ample fenced yard. Rare opportunity in a great and convenient location!

729 Hambrick Ave, Lexington

$750,000

3 Beds ⋅ 2 Baths ⋅ 25505525 MLS

Discover the peace you've been searching for on 17.6 acres of beautiful Kentucky countryside in Fayette County. This 3-bedroom, 2-bath home offers 2,125 sq ft of warm, comfortable living space with large rooms, great natural light, and scenic views from every window. The home is ready for you to make it your own and is intentionally priced below market value to allow room for your updates and improvements. If you've been dreaming of a horse property, this is ideal. The land is open, usable, and laid out perfectly for pastures, riding space, and future barns—horses welcome. Whether you want space for animals, gardening, weekend adventures, or simply room to relax, this rare Fayette County acreage offers unmatched privacy and endless possibility. Enjoy true country living with convenient access to both Lexington and Richmond—the best of both worlds and a property that doesn't come along often.

7897 Old Richmond Rd, Lexington

$1,090,000

4 Beds ⋅ 3 Baths ⋅ 26021097 MLS

Set on one of Lexington's most beloved tree-lined streets in the coveted Chevy Chase / Ashland Park area, this 1935 Kentucky limestone Cotswold/Tudor home is a rare blend of storybook character and modern living. From the steeply pitched gables and stone chimney with terracotta chimney pots to the arched red front door and bluestone covered porch, the curb appeal is straight out of a storybook. Timeless and natural materials were chosen throughout to honor the home's original architecture while quietly delivering every modern convenience. Inside, graceful arched doorways and refinished hardwood floors set a warm, inviting tone. A completely renovated open-concept kitchen anchors the main level with custom cabinetry, granite countertops, limestone backsplash, a gas range, and a breakfast-bar peninsula that flows effortlessly into the dining and living spaces — with double pocket doors opening to a light-filled sunroom. A custom travertine-slab fireplace with a herringbone-tile firebox and gas insert serves as a stunning focal point. Original curved ceilings in two of the upstairs bedrooms — a signature of authentic Cotswold design — and distinctive staircase balusters are charming reminders of the home's 1935 pedigree. The 2005 two-story addition expanded the living space with Hardie board siding, solid-wood interior doors with crystal knobs, and a stone skirt around the foundation — some of it original stone reclaimed from the main home. Walls of French doors along the addition open to the backyard, filling the home with natural light and creating a seamless indoor-outdoor flow. Custom built-ins throughout, including a glass-front dining room hutch and a laundry room/pantry with granite and travertine, reflect the same craftsmanship found in every corner. The spa-like primary bath is a true retreat, featuring a freestanding clawfoot soaking tub, a long double vanity with marble countertop, custom cabinetry, a chandelier, penny-tile flooring, and a custom laundry chute. A second-floor secondary bath is equally refined with a new porcelain tile shower and floor, custom cabinetry, and marble countertops. The finished basement is a destination of its own: custom and reclaimed-wood shelving, a bar area with a beverage fridge, a cedar closet, generous storage, and durable LVP flooring — with the adjacent utility area proactively waterproofed to protect the finished space. Outdoors, a generous 17' x 29' patio topped with Pennsylvania bluestone — accessible through multiple sets of French doors — creates an elegant, private setting for entertaining. Out front, professional landscaping and mature trees and hydrangeas, a bluestone covered front porch and walkway, and laurel-stone edging. A rare extra-deep 22' x 26' detached garage with carriage-style doors, coordinating stone front and Hardie board siding was designed to blend seamlessly with the home, and even reuses windows from the original house. Behind its timeless facade, this home offers the best of both worlds: the irreplaceable character of a 1935 Chevy Chase original, paired with thoughtfully updated interiors that honor its heritage down to the smallest detail. Walkable to the shops and restaurants of Chevy Chase and just minutes from the University of Kentucky, downtown, and everything that makes this one of Lexington's most sought-after neighborhoods. Property being sold as is with inspections welcomed.

409 Dudley Rd, Lexington

$449,900

4 Beds ⋅ 2 Baths ⋅ 26021347 MLS

Welcome to this Historic Pensacola Park home built in 1925 located in downtown Lexington! It has been over 33 years since this home was last on the market. This home features 4 bedrooms, 2 bathrooms, a complete separate living area upstairs with its own kitchen and bath as well as its own entrance from the back which would allow for separate living if wanted. Lots of potential for this home and all of the options that it has to offer!

1909 Nicholasville Rd, Lexington

$110,000

2 Beds ⋅ 1 Baths ⋅ 26006874 MLS

Investor looking for an opportunity in downtown Lexington? This is for you. Currently rented at $995 until 8/31/2027, it features updated shingles and Heat Pump from 6/2020. Conveniently located near dining, parks, and public transit, the property delivers a strong combination of value, accessibility, and long-term potential.

523 1/2 Ohio St, Lexington

$2,225,000

4 Beds ⋅ 5 Baths ⋅ 26020802 MLS

Rare opportunity to own a completely renovated home on Richmond Road. located on the corner of Richmond Rd. and Bassett Avenue directly across from the Henry Clay estate; this 1923 colonial home has been gutted down to the studs and meticulously renovated by Wooddale Partners. Every inch of the interior is brand new. Enter through the front door into a bright and inviting living room with full high window and fireplace looking into the formal dining room with a large triple window and full height window. The large family room is open to the kitchen that has custom handmade inlay cabinetry with built in fridge and dishwasher, 48? gas range, direct ventilation range hood, and large 48? workstation sink looking out onto the covered lanai that features a large gas fireplace, built in grill and fridge. The main level also features a breakfast nook, office, and mud/ laundry room. The primary bedroom has a large walk-in closet with custom built ins and island, sitting room, and beautifully designed bathroom. 3 guest bedrooms are all on suite with built in closets. The property sits on a 1/3 of an acre with a large yard, completely fenced in with room for an in ground pool. The detached 3 car garage is accessed off Bassett avenue with a driveway that fits 9 cars. Book your showing today to see all the fabulous hand selected finishes in person.

1501 Richmond Rd, Lexington

$485,000

2 Beds ⋅ 3 Baths ⋅ 26020455 MLS

This charming historical jewel is ready for it's next owner. It's not often you find over 2000 square feet in a house built in the 1910's but this one delivers with an open concept chefs kitchen dining combination that opens to a side patios for outdoor living. There is a large living space with a half bath for guests plus a foyer with character.... Speaking of character, this home has loads of it, exposed brick, decorative fireplaces and amazing lighting. Two spacious bedrooms both with private baths provide plenty of room for everyone to spread out. Finally, the backyard is oversized for the area with room for gardening or entertaining. Walk to all downtown has to offer or to Transylvania University- you don't want to miss making this one your own!

617 N Broadway, Lexington

$559,900

3 Beds ⋅ 3 Baths ⋅ 26019969 MLS

Welcome to 109 N. Ashland Avenue, a timeless Craftsman bungalow nestled in one of Lexington's most desirable and walkable neighborhoods. This charming 3-bedroom, 2.5-bath home perfectly blends classic character with modern comfort. Relax on the covered front porch before stepping inside to discover warm hardwood floors, traditional living areas, and an inviting floor plan designed for both everyday living and entertaining. Outside, the deep backyard offers plenty of space to enjoy, while the unbeatable location puts you just steps from local restaurants, coffee shops, parks, and everything that makes the Ashland Park/Bell Court area so special. Whether you're taking an evening stroll through the neighborhood or enjoying nearby Chevy Chase and downtown Lexington, you'll love the convenience and vibrant lifestyle this location provides. Don't miss this rare opportunity to own a classic Lexington bungalow in an exceptional location. This home is being offered AS-IS, inspection welcome. Please note the alleyway includes an easement for this property to access two off road private parking spaces.

109 N Ashland Ave, Lexington

$699,000

3 Beds ⋅ 3 Baths ⋅ 26019382 MLS

Rare opportunity to own a beautifully updated triplex in Lexington's highly sought-after Chevy Chase neighborhood. 304-306 Ridgeway Drive features three 1BR/1BA units and is being sold partially furnished. Ideally located just steps from the University of Kentucky, downtown Lexington, UK HealthCare, restaurants, shopping, and entertainment. With thoughtful updates and an unbeatable location, this property offers incredible flexibility and a unique opportunity to own in one of Lexington's most desirable areas.

304-306 Ridgeway Rd, Lexington

$1,499,000

4 Beds ⋅ 3 Baths ⋅ 26019454 MLS

A rare offering in the heart of Ashland Park, this distinguished Colonial Revival residence stands as a testament to the enduring elegance and architectural refinement that defined the style's popularity at the turn of the century. Among the earliest homes constructed on coveted South Ashland Avenue, it enjoys a commanding presence and a rich connection to one of Lexington's most treasured historic neighborhoods. A gracious front porch sets the tone, inviting leisurely afternoons spent greeting neighbors and enjoying the timeless charm of tree-lined South Ashland Avenue. Inside, soaring ceilings, exquisite millwork, and a wide center hall create a sense of grandeur rarely found in today's homes. A remarkable reverse staircase, illuminated by a skylight above, provides access to the second level from the rear of the residence while filling the home's interior with natural light. Throughout, distinctive crown moldings highlight the craftsmanship of a bygone era, while the kitchen's handsome coffered ceiling adds warmth and architectural interest. Designed for both elegant entertaining and comfortable daily living, the first floor features an exceptional collection of gathering spaces, including a formal living room, formal dining room, a richly appointed den, an inviting family room, a spacious kitchen, a bedroom, and a full bath. Each room flows gracefully into the next, creating an atmosphere that is both sophisticated and welcoming. The second level features a spacious primary suite with a cozy sitting area, providing a private retreat at day's end. Two additional bedrooms and a full bath enjoy lovely views of the beautifully landscaped rear grounds. Outdoors, the private backyard serves as a peaceful oasis, with mature landscaping and a deck perfect for al fresco dining and entertaining. The porte cochere provides covered parking and everyday convenience while complementing the home's historic character. Ideally located just steps from the boutiques, cafés, and restaurants of Chevy Chase, this exceptional residence offers the rare opportunity to own a piece of Ashland Park history while enjoying one of Lexington's most desirable and walkable neighborhoods.

262 S Ashland Ave, Lexington

$195,000

3 Beds ⋅ 1 Baths ⋅ 26019298 MLS

**Location is everything! Welcome home to this adorable 3 bed, 1-bath ranch-style home inside New Circle Road! Boasting 1,000 square feet of efficiently designed living space, this home features easy-care laminate floors and a fully equipped updated kitchen with a dishwasher, range, and refrigerator. This home also offers a large private 3rd bedroom or additional family room!!! Step outside to a lovely porch and a spacious large wood-fenced backyard complete with a storage shed—perfect for pets, gardening, or extra storage. Central location near NO-LI District, Greyline Station, Warehouse District, and DOWNTOWN Lexington!! This move in ready property combines convenience and comfort!! Schedule your private showing before it's gone!!

1043 Marcellus Dr, Lexington

$765,000

4 Beds ⋅ 3 Baths ⋅ 26016618 MLS

LISTED BELOW APPRAISED VALUE!! Step into a piece of Lexington history where timeless architecture meets sophisticated modern living. Built in 1875 and inspired by the elegance of a mid-1700s Charleston, South Carolina residence, this remarkable 2,640-square-foot home is one of downtown's true architectural treasures. Completely renovated in 2017, every update was thoughtfully designed to preserve the home's irreplaceable character while seamlessly incorporating today's modern conveniences. Every room tells a story while providing the comfort and style today's buyers expect. To top it off LOCATION!!! Situated in one of downtown Lexington's most prestigious historic districts, you're just steps from everything that makes city living exceptional. Walk to Rupp Arena, acclaimed local restaurants, breweries, boutique shopping, coffee shops, entertainment, parks, and year-round events. Historic charm. Modern luxury. An unbeatable downtown lifestyle. Opportunities like this rarely come along.

472 W Second St, Lexington

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 26016794 MLS

Experience the timeless character of this beautifully restored downtown Lexington home, where historic charm meets thoughtfully updated modern living. Ideally located within walking distance of downtown restaurants, shopping, Central Bank Center, and the new Gatton Park on the Town Branch, this home offers exceptional convenience in the heart of the city. Extensive improvements include updated sewer and plumbing lines, electrical, HVAC, insulation, appliances, and more, providing peace of mind while preserving the home's original character. Hardwood flooring flows throughout the interior, complemented by a beautifully restored staircase that serves as a striking architectural centerpiece. The main level features an open-concept kitchen and family room anchored by a natural gas linear fireplace and bar area, creating an inviting space for both everyday living and entertaining. The kitchen opens directly to the rear deck and patio, extending the living space outdoors. A separate living room and formal dining room provide additional flexibility for gatherings and special occasions. Upstairs, you'll find three bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite includes a large walk-in closet and an updated ensuite bathroom. The third floor offers a versatile office or flex space with hardwood flooring, while the finished basement provides additional living space ideal for a media room, recreation area, or entertaining, along with unfinished storage. Step outside to a private backyard retreat featuring a deck, patio, and hot tub, creating a rare outdoor oasis in downtown Lexington. Whether enjoying a quiet evening or hosting family and friends, this space is designed to be enjoyed year-round. With its exceptional restoration, modern updates, versatile living spaces, and premier downtown location, this home offers a unique opportunity to enjoy the best of historic Lexington living. Schedule your private showing to experience everything this remarkable property has to offer.

565 W Second St, Lexington

620 N Martin Luther King Blvd, Lexington

$195,000

4 Beds ⋅ 3 Baths ⋅ 26000820 MLS

620 N Martin Luther King Blvd, Lexington

$649,000

3 Beds ⋅ 2 Baths ⋅ 26011135 MLS

Historic Thomas January office renovated and rebuilt from foundation up offers modern amenities including tankless water heater, marble kitchen and bathrooms, new heat and air, plumbing, electrical, appliances and salvaged hardwood floors. Property is income producing as Airbnb and VRBO but could be used as single family dwelling. House includes a charming and private courtyard with neighboring Gratz Park and Transylvania University close by. Walking distance to restaurants, Opera House, Rupp Arena, and all downtown has to offer. Three designated parking spaces behind the house and on street parking in front of the house. Opportunity to own one of Lexinton's most unique properties. House being sold AS IS. Inspections welcome.

322 W 3rd St, Lexington

$135,000

4 Beds ⋅ 3 Baths ⋅ 26013120 MLS

Calling all investors, flippers. and ambitious homeowners. Skip the heavy lifting and step into a property where some of the hardest work has already been completed. Besides their initial investment, the current owners have paid over $50,000 in materials and labor along with putting in countless hours of their own sweat equity into this home before putting the brakes on this mid construction flip. They cleaned out and demoed part of the original home, framed the upstairs, put on new siding, roof, and windows but unfortunately, sometimes, life just gets in the way. Designed to be a stunning 4 bedroom 2.5 bathroom home, the layout is exceptionally functional with a large entry foyer, first floor primary bedroom with an attached primary bathroom, eat in kitchen with pantry, half bath, and living room. Head upstairs to find the second story completely framed for 3 bedrooms, bonus/flex room, and a full bath. There's still plenty of time to change the floor plan to showcase your vision. There is front street parking and you can easily park a car in the rear yard too. With finished neighborhood comps pulling in the mid $200s and up, there is plenty of margin left for a smart investor or savvy homeowner that wants to finish this flip. Property being sold AS IS.

210 E 7th St, Lexington

$1,595,000

2 Beds ⋅ 3 Baths ⋅ 26014762 MLS

Set on approximately 5 acres, this equestrian property offers the perfect blend of functionality and location—just minutes from downtown Lexington and the Kentucky Horse Park. Thoughtfully designed for the dedicated equestrian, the farm features a premium 120' x 200' GGT footing arena complete with irrigation. The property also boasts 10-matted stalls with beautiful new stall fronts, a separate barn bathroom, laundry room, and a stylish temperature controlled tackroom. The charming 2-bedroom, 1.5-bath. residence offers comfortable living with a full basement that presents excellent potential for additional finished space—perfect for expanding your living area, creating a home office, or adding guest accommodations. A new septic has recently been installed along with new water heater (both 2024) and the entire house has new plumbing. Whether you're seeking a private equestrian facility or a refined hobby farm in the heart of horse country, this property offers an exceptional blend of convenience, quality, and opportunity in one of Kentucky's most coveted locations.

166 Swigert Ave, Lexington

$1,395,000

4 Beds ⋅ 4 Baths ⋅ 26014199 MLS

Beautifully maintained classic home in the highly desirable Fairway. Thoughtfully updated with exceptional quality, this home features gleaming hardwood floors, a new slate roof, irrigation system, and fresh paint throughout. Move right into your forever home with no improvements needed. Enjoy outdoor living on the wonderful private brick terrace, enclosed by a charming herringbone brick wall that creates a peaceful and inviting retreat.

245 Holiday Rd, Lexington

$275,000

2 Beds ⋅ 2 Baths ⋅ 26012078 MLS

Step into one of Lexington's true hidden treasures, where historic charm meets modern comfort. Perfectly located just minutes from downtown and the interstate, this home offers unbeatable walkability to local favorites like West 6th Brewery, North Lime Coffee & Donuts, and the bustling Greyline Station. Inside, you'll find a stunning blend of craftsmanship and style. The home features granite countertops, a custom kitchen with a mini bar, and thoughtful upgrades that complement its original character. The primary suite showcases a luxurious custom tile shower, providing a private retreat with spa-like comfort. Every detail has been carefully designed--from the custom built floating shelves and stylish finishes to the inviting flow of the living spaces. Step outside to enjoy a secluded backyard oasis, ideal for relaxing or entertaining, along with a convenient driveway and beautiful exterior updates that enhance the home's curb appeal. This property truly captures the essence of downtown living, a historic gem with modern updates in one of Lexington's most vibrant neighborhoods. Whether you're seeking a cozy urban home or a smart investment, this one is sure to impress.

607 N Broadway, Lexington

$2,323,000

5 Beds ⋅ 4 Baths ⋅ 26008568 MLS

If you're looking for legacy, luxury, and grand proportions, Highland Hall has it all--without the need for renovations. Located on a gated 5-acre estate near Lexington's Richmond Road corridor, Highland Hall was built by the son and namesake of Kentucky's very first Governor, Isaac Shelby. The estate has been meticulously restored to retain its historic features while creating a fully modernized, turn-key experience. This 6,800+/- sqft Greek Revival masterpiece was originally built in 1855 and now features a brand-new 2026 roof, all-new plumbing, updated 2-tank septic, and 400-amp electrical. Climate control is handled by a 3-unit geothermal HVAC system (8 GeoWells) and an additional heat pump for the first-floor primary suite. Enjoy all-new Anderson Pro Series windows, fresh premium paint, a Lutron system, original hand-milled heart pine floors, and custom walnut trim. The grand interiors flow to a private, fenced rear yard with a 2024 hot tub, outdoor shower, and a pond. This home has mastered the concept of intimate spaces specifically curated for daily living alongside grand spaces for lavish entertaining. Professionally redesigned since its history as a Decorators Showcase Home. Prequalified credentials required. **Furnishings priced upon request. Excludes any artwork collection**

6208 Old Richmond Rd, Lexington

$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

$439,000

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

$5,350,000

8 Beds ⋅ 8 Baths ⋅ 24020331 MLS

One of the most desirable properties I've ever had the privilege to sell - the Marylou Whitney Farm. It has it ALL: historic main residence, 2 story guest home, extraordinary pool house with Olympic size pool, studio, log cabin chapel, rose garden, 2 horse barns with 16 stalls with frontage on 2 roads in the heart of the horse industry!

3521 Bryan Station Rd, Lexington

$2,500,000

4 Beds ⋅ 4 Baths ⋅ 26010644 MLS

Nestled in the heart of historic Ashland Park, this 1925 residence stands as a rare example of timeless architecture paired with thoughtful modern refinement. A grand 12-foot-wide Palladian entry, framed by marble walls and sandstone columns, sets the tone the moment you arrive. The front terrace offers a gracious outdoor gathering space, with fan-lighted French doors that open directly into the dining room—an inviting flow that speaks to the home's original purpose: elegant entertaining. Inside, the scale is unmistakably classic. The 28-foot living room is anchored by an impressive Italian marble fireplace, a true statement piece imported from Italy, and tall windows that fill the room with natural light. A Palladian door leads seamlessly into the solarium, where a cast- iron working wall fountain adds charm and character few homes can claim. The remodeled and enlarged kitchen blends today's function with timeless style, offering custom cabinetry with glass-front doors, generous workspace, and an adjoining butler's pantry—ideal for hosting, staging, and everyday ease. The second level features four comfortable bedrooms and three baths, including access to a lovely screened sun porch that feels pulled from another era. The third floor provides excellent flex space—perfect for a home office, studio, or a teenager's retreat. Outside, the 2-car garage includes a finished room with a full bath, making it an excellent option for an office, art studio, or guest suite. A home of this quality, preserved and elevated over a century, rarely becomes available. It delivers heritage, craftsmanship, and livability in one of Lexington's most treasured neighborhoods. Ideally located minutes from downtown Lexington, Chevy Chase shopping, restaurants, and the University of KY.

1014 Richmond Rd, Lexington

$289,000

3 Beds ⋅ 2 Baths ⋅ 25507294 MLS

Located inside New Circle Road with quick access to downtown Lexington, this classic brick home offers space, character, and endless potential. Featuring 3 bedrooms, 2 full baths, and large rooms throughout, this home provides the charm of an older build with the functionality today's buyers need. The property includes a detached 2-car garage with a built-in workshop, plus an unfinished apartment above—perfect for future rental income, a guest suite, studio, or private office. A nice-sized yard offers room to relax, garden, or entertain, and the central location puts you minutes from restaurants, parks, UK campus, and everything Lexington has to offer. A rare opportunity to own a spacious, character-filled home with bonus space and unbeatable convenience! Estate Sale, property being sold as-is.

1613 Versailles Rd, Lexington

$725,000

3 Beds ⋅ 3 Baths ⋅ 25501400 MLS

Welcome to your dream home in the highly sought-after Fairway neighborhood! This beautifully designed 3-bedroom, 3-bathroom residence offers the perfect blend of style, comfort, and function. Enjoy an expansive open-concept living area that flows seamlessly into a light-filled sunroom—ideal for entertaining or unwinding in peace. The large kitchen is a chef's delight, with ample space for cooking and gathering. Each bedroom offers generous space, while all three full bathrooms are thoughtfully updated. Whether you're hosting friends or enjoying a quiet evening, this home delivers the perfect setting in one of the area's best locations. More photos coming, including a beautiful primary en-suite full bathroom. Remodeled full bathroom upstairs including two bedrooms. Also a library on the first floor of the living room.

242 Henry Clay Blvd, Lexington

$725,000

3 Beds ⋅ 3 Baths ⋅ 26013142 MLS

Great opportunity! Location, Location, Location! Nestled in the highly desirable Edgemoor/Tahoma Terrace neighborhood, this exceptional two-story brick home offers timeless charm, outstanding curb appeal, and a lifestyle that is hard to find. Start your mornings with a cup of coffee on the inviting covered front porch before stepping inside to a spacious foyer that sets the tone for the warmth and character found throughout the home. The main level features a welcoming living room, dining room, kitchen, bedroom, and full bath, providing both comfort and flexibility for everyday living. Upstairs, you'll find an exceptionally spacious primary suite featuring a large soaking tub, oversized walk-in shower, heated floors, and a heated towel rack—creating a true retreat. An additional bedroom, full bath and a large upstairs laundry room add convenience and functionality. Situated on approximately 2/3 of an acre, this property offers an abundance of outdoor living space. Enjoy relaxing evenings on the covered back patio overlooking a fence backyard surrounded by beautifully mature trees and landscaping. This creating a peaceful and private setting perfect for entertaining, gardening, or simply enjoying nature. Additional features include an attached carport, a second two-car carport, and two storage buildings. The large storage building offers a workshop, shelving, and ample storage space. The expansive backyard provides plenty of room for recreation, including the potential for a pickleball court. What truly sets this home apart is its unique layout, offering three spacious bedrooms, 3 full bathrooms. Conveniently located near the University of Kentucky, UK HealthCare, Baptist Health, Kroger Field, Downtown Lexington, The Arboretum, Southland Drive, and an abundance of shopping, dining, and entertainment, this home combines classic character with an unbeatable location. Schedule your private showing today!

111 Edgemoor Dr, Lexington

$489,000

3 Beds ⋅ 3 Baths ⋅ 26005663 MLS

This home has been lovingly renovated to bring modern convenience to its next owner while preserving the charm of yester-year. It features 3 bedrooms, 2.5 baths, large kitchen and adjacent flex room with matching floor to ceiling cabinetry that could serve as a mud room, pantry, or drop zone. Additionally, the living room and dining room are open and airy with the refinished original hardwood floors. All new wiring, lighting, plumbing, HVAC, water heater, roof, gutters, insulated windows, tile floors in bathrooms and kitchen, new bathrooms, new kitchen and appliances, paint and more all ready to welcome you. Close to downtown, Jefferson Street corridor, NOLI, shopping, restaurants, arts, entertainment and more. A downtown gem waiting for you to see.

615 Bellaire Ave, Lexington

$800,000

3 Beds ⋅ 5 Baths ⋅ 26013475 MLS

Rare opportunity to own a piece of downtown Lexington history at 579 W Short Street. Ideally located in the heart of the city, this unique property places you within walking distance of Lexington's finest restaurants, shopping, entertainment, parks, and local attractions, offering the true downtown living experience. This three-story historic home is ready for its next chapter. The property has been extensively prepared for renovation, with much of the heavy lifting already completed, including updated electrical and plumbing systems, as well as excavation of the basement to create taller ceilings and expanded usable space. With the home gutted and ready for finishing, buyers have the unique opportunity to design and customize the interior to their own vision while preserving the character and charm of a historic downtown residence. Adding to the property's appeal is a detached two-car garage with a one-bedroom apartment above, offering excellent potential for rental income, guest quarters, a home office, or mother-in-law suite. With valuable yard space, off-street parking, income-producing possibilities, and an unbeatable downtown location, this is a rare chance to create a one-of-a-kind residence or investment property in one of Lexington's most sought-after areas. Bring your vision and transform this historic gem into something truly extraordinary.

579 W Short St, Lexington

$479,500

1 Beds ⋅ 1 Baths ⋅ 26010609 MLS

Add your chapter to the story of this iconic c. 1805 log cabin, 220 years after its construction. Thought to be the oldest surviving log residence in Lexington still on its original site, this two-story, two-bay clapboard-wrapped home offers a blend of early Kentucky heritage and downtown convenience. In 1994, the Blue Grass Trust for Historic Preservation saved the structure from demolition, undertaking a careful restoration that preserved its integrity. Today, its rich character endures through hand-hewn logs, exposed beams, very old hardwoods, two brick fireplaces, and historic cabinetry including linen ''presses.'' An updated adjoining kitchen and bath retain traditional charm. Upstairs, a sunlit bedroom provides ample space for a sitting area beside the fireplace. French doors and limestone slab steps lead to the spacious rear greenspace - a coveted & rare feature for a downtown property. A stone pathway leads to a generous, private off-street parking area accessible from Mack's Alley. Recent enhancements include a remodeled bath, exterior painting, new heat pump, a new Bosch dishwasher, and a handcrafted storm door by Bourbon Millworks. The property's R-2 zoning adds further appeal and possibilities. Design review district.

361 S, Lexington

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