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$775,000
5 Beds ⋅ 2 Baths ⋅ 26025074 MLS
This charming duplex in the highly sought-after Ashland Park neighborhood of Lexington offers a versatile property that features a total of five bedrooms and two bathrooms, along with spacious living and dining areas in each unit. (3 bedrooms and 1 bath in one unit and 2 bedrooms and 1 bath in the other unit). Both parts of the duplex offer bright, inviting interiors with abundant natural light and comfortable living spaces ideal for everyday living or entertaining. Each unit includes a well-equipped kitchen with ample room for cooking and gathering. The generously sized bedrooms provide privacy and flexibility, while the bathrooms are thoughtfully designed for both style and function. Outside, enjoy a welcoming front porch and a large backyard perfect for relaxing, gardening or hosting outdoor gatherings. Located in the heart of Ashland Park, this property offers convenient access to parks, schools, local dining, and shopping, as well as easy proximity to downtown Lexington. Whether you're looking for an owner-occupied opportunity, investment property, or multi-generational living, this duplex presents a wonderful opportunity in one of Lexington's most desirable neighborhoods. Storage and laundry facilities in the lower level, plus laundry hook up in first floor unit. 48 Hour Showing Heads Up Requested. Home selling AS-IS, with inspections welcome. Home is located in Historic H-1 Overlay.

1056-1058 Fontaine Rd, Lexington
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 26024479 MLS
Welcome to 1820 Richmond Road, an exceptional 4 bedroom, 3 bath residence set on a beautiful half acre lot in one of Lexington's most desirable neighborhoods. Extensively remodeled from floor to ceiling, this home seamlessly combines timeless character with thoughtful modern updates. The brand new kitchen, beautifully renovated bathrooms, refinished hardwood floors, and custom crown molding are just a few of the details that set this home apart. Unique touches throughout, including integrated Bluetooth speakers, heated bathroom features, and thoughtful built ins, add an exceptional level of comfort and convenience. The partially finished basement provides an inviting entertainment room centered around a gas fireplace, while abundant storage throughout the basement and the walk up attic with finished flooring offer functionality rarely found in a home of this caliber. Outside, the composite deck and enclosed sunroom create an ideal setting for entertaining or enjoying the privacy of the expansive lot. A two car garage with an EV charging port adds modern convenience. From its timeless renovation to its exceptional location and abundant space, 1820 Richmond Road is a home that is as functional as it is impressive.

1820 Richmond Rd, Lexington
$1,240,000
4 Beds ⋅ 3 Baths ⋅ 26023548 MLS
211 McDowell Road is classic Ashland Park - an inviting 1920s Craftsman with the character and gracious proportions that make this neighborhood so special. Restored by Andover Construction prior to the current owners' purchase and gently lived in as a 2nd residence since, the home features the original staircase and beautiful hardwood floors, multiple fireplaces, generous living and dining spaces, four bedrooms and a third-floor bonus room. The covered front porch feels right at home on McDowell Road, while the newly redone Trex deck extends the living space to the fenced backyard, along with a detached two-car garage. Other recent improvements include a tankless water heater, sump pump, irrigation system and new back doors. All just minutes from Chevy Chase, downtown Lexington, and the University of Kentucky.

211 Mcdowell Rd, Lexington
$1,530,000
4 Beds ⋅ 6 Baths ⋅ 26022514 MLS
We invite you to discover 1337 Cooper Drive, a distinctive Lexington residence where the character of an established home meets the space, comfort, and functionality created through thoughtful additions by previous owners. Situated on a quiet street on an expansive 0.641 +/- acre lot, this exceptional property offers approximately 5,292 sq ft of finished living space, 4 bedrooms, 5.5 baths, remarkable outdoor spaces and an enviable location convenient to some of Lexington's most beloved destinations. The home's setting is truly special. A significant investment has transformed the backyard into a private, park-like retreat, highlighted by extensive landscaping, designed by Terrain Landscaping and custom plantings by Wilson Landscaping Supply in June 2025. The beautifully designed grounds provide a peaceful backdrop for morning coffee, outdoor entertaining, gardening or simply enjoying the privacy of this unusually generous in-town lot. A wrap around porch further connects the home to is beautiful surroundings. The sitting area within the primary en-suite opens directly onto the porch, creating a wonderful indoor-outdoor retreat overlooking the private backyard. The spacious primary en-suite is designed for both comfort and privacy, featuring a dedicated sitting area, walk-in closet, soaking tub and separate shower. A separate laundry room (both washer and dryer convey with property) and home office add convenience and flexibility for today's lifestyle. Throughout the home, generous living spaces reflect its history and evolution. Originally constructed in 1954, the residence has been expanded over the years by previous owners, resulting in a floor plan that provides exceptional room for working from home, hosting guests, and comfortable everyday living. A separate living space complete with bedroom, sitting area, beverage bar and full bath is located over the garage, on the opposite end of the primary en-suite. The walk-out basement adds even more versatility, with approximately 735 sq ft of finished living space, including a full bath and fireplace with gas logs (New March 2026) and an additional 1,765 sq ft of unfinished space offering tremendous potential for storage, recreation, a workshop, home gym, or future customized living areas. Outside Trex fencing (New July 2025) with a double gate enhances the privacy and functionality of the backyard. A 26 KW Generac whole house generator (New 2024) provides additional peace of mind. The property also includes a substantial 676 sq ft, forward facing garage. The home is offered with a full appliance package, including a refrigerator purchased August 2026, and washer and dryer (New April 2026). And then there is the location. From Cooper Drive, enjoy the charm and convenience of an established Lexington neighborhood where you can walk to Romany Road and Wheeler's Pharmacy, a longtime gathering place, for a meal, beverage or visit with friends. Prefer two wheels? Bike to Henry Clay's Ashland Estate, Ecton Park, or the University of Kentucky, placing campus and the energy of central Lexington within easy reach while returning home to the privacy and tranquility of your own park-like setting. 1337 Cooper Drive is more than a spacious home - it offers a distinctly Lexington lifestyle: an established neighborhood, an extraordinary private lot, beautifully landscaped outdoor spaces, abundant room to live and entertain, and convenient access to the places that make this area so special.

1337 Cooper Dr, Lexington
$225,000
1 Beds ⋅ 1 Baths ⋅ 26021193 MLS
Welcome to Hanover Towers, where convenience, comfort, and location come together in one of Lexington's most desirable downtown corridors. This beautifully refreshed one-bedroom condo features new carpet, fresh paint throughout, thoughtful upgrades, and is truly in pristine condition. The home offers a large bedroom, a spacious family room, and an inviting layout that feels bright and easy to live in. Situated at the corner of S. Hanover & E. Main Street, you'll enjoy effortless access to Chevy Chase, downtown dining, shopping, parks, and everyday essentials — all steps from your front door. Hanover Towers provides amenities rarely found at this price point: a doorman, workout room, beautifully maintained lobby and hallways, rooftop terrace, gathering rooms for visitors, covered parking for owners, guest parking, public spaces, a laundry facility, and private basement storage for your extra belongings. Even better, all amenities and utilities are included in the HOA dues, making budgeting simple and predictable. This is a fantastic opportunity to own in a prime Lexington location — whether you're downsizing, investing, or seeking a low-maintenance urban lifestyle. Don't miss it.

101 S Hanover Ave Unit 4D, Lexington
$725,000
4 Beds ⋅ 2 Baths ⋅ 26019486 MLS
Nestled in the heart of Ashland Park, this classic brick duplex offers timeless character in one of Lexington's most sought-after neighborhoods. Each spacious unit features hardwood floors, original built-ins, separate living and dining rooms, two bedrooms, and a full bath, making a blend of historic charm and comfortable everyday living. A shared basement level provides laundry and additional storage, while the private brick courtyard creates a peaceful outdoor retreat. Whether you're looking to expand your investment portfolio, owner-occupy while generating rental income, or preserve a piece of Lexington history, opportunities like this are increasingly rare. Just a short stroll from Chevy Chase shops, local restaurants, parks, and everything Ashland Park has to offer, this is location, character, and versatility all in one.

110-112 S Hanover Ave, 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
$359,900
2 Beds ⋅ 2 Baths ⋅ 26019062 MLS
Just a stone's throw from downtown, Hanover Towers is understandably in high demand. It rests within lovely historic Ashland Park, at the corner of Hanover and East Main. Within a short walk are Woodland Park, Henry Clay and Chevy Chase. Hop a bike and its 5 minutes to Rupp, the farmer's market, Gatton Park or the distillery district. Or stay right at home and catch spectacular views of downtown Lex. and the sun setting over the bluegrass on the Hanover Towers rooftop. The complex has covered parking for owners, guest parking, public spaces, basement storage, a laundry facility and a workout room. Most impressive, whether you are coming or going, a doorman will greet you and assist you at the front of the building daily through 6 pm. This lovely 2nd floor corner unit in Hanover Towers was remodeled in 2022 and in pristine condition. The standard clunky Hanover towers glass partitioning in the living room was removed, opening up that space to the amazing morning sunrises through the oaks. The kitchen was gutted, re-configured, opened up to the living room and remodeled. All new. The baths too were renovated, including new vanities and fixtures, new tile and glass. All flooring was replaced, as well. Vacant and move-in ready. Furnishings are negotiable.

101 S Hanover Ave Unit 2M, Lexington
$810,000
4 Beds ⋅ 4 Baths ⋅ 26012755 MLS
Investment Opportunity in Ashland Park! Located on a desirable corner lot in the heart of Ashland Park, just two blocks from Henry Clay Estate, this well-maintained 4-plex offers timeless charm and excellent income potential. The property features four oversized one-bedroom, one-bath units, each with spacious closets and its own covered front porch. A welcoming entry foyer provides access to the upper-level apartments and the expansive basement. The large basement includes individual washer and dryer hookups for each tenant, along with private walk-in storage units. First-floor apartments offer both front and rear porch entrances and are conveniently located just steps from the covered four-car garage. Overlooking the picturesque, park-like islands along Slashes Road, this property combines a prime location, classic character, and strong rental appeal in one of Lexington's most sought-after neighborhoods.

305 Sycamore 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
$1,825,000
4 Beds ⋅ 6 Baths ⋅ 26010477 MLS
Built in 2016, this exceptional contemporary ranch offers over 5,000 square feet, four bedrooms, six baths and a finished lower level in Lexington's coveted Ashland Park neighborhood. Thoughtfully designed with sophisticated finishes and abundant natural light, the home creates a seamless connection between its indoor and outdoor living spaces. An expansive covered terrace with an ipe wood ceiling opens naturally to the kitchen, dining and living areas, providing an impressive setting for entertaining. The kitchen combines style and function with European-inspired Mouser cabinetry, an oversized gathering island, high-end appliances and dramatic quartz surfaces extending to the ceiling. Oversized casement windows enhance the home's clean architectural lines and fill the open living areas with light. A sleek cantilevered quartz fireplace provides a striking focal point in the living room. The main-level primary suite offers generous proportions, a beautifully finished shower and a well-appointed walk-in closet. A second main-level bedroom with an ensuite bath provides added flexibility for guests or a home office. A laundry area and convenient drop zone complete the first floor. The finished lower level expands the home's entertaining and living space with a second gathering area, a full bar and multiple flexible rooms. Two additional bedrooms each feature an ensuite bath and walk-in closet, creating comfortable private accommodations for family and guests. With four ensuite bedrooms, designer finishes and a highly functional ranch-style layout, this distinctive residence presents a rare opportunity to enjoy contemporary living in one of Lexington's most established neighborhoods.

1897 Hart Rd, Lexington
$722,450
3 Beds ⋅ 4 Baths ⋅ 26014485 MLS
A once-in-a-lifetime opportunity to renovate a timeless architecturally unique home in the heart of Ashland Park, one of Lexington's most sought-after neighborhoods. Situated on South Hanover Avenue, one of Lexington's most desirable addresses, this classic 1923 brick two-story home with partially finished basement has been prepared for its next chapter. The owner has removed all kitchen and bathroom cabinetry and fixtures, removed all attic insulation, and completed other partial internal demolition. The property now essentially provides a blank canvas for a complete renovation as you envision. The property was previously configured with a living room, dining room, kitchen, separate breakfast area, sunroom and half bath on the first floor; three bedrooms, two full baths and laundry room on the second floor; and with two windowed bedrooms and full bath in the partially finished basement. The internal layout on all floors is capable of being reconfigured to create newly sized living areas. Exterior renovations including a rear addition and new garage are also possible, subject to Board of Architectural Review approval due to the property being in a historic district. The property is being sold AS-IS, and the seller makes no representations or warranties regarding the property or its condition. The home was occupied by the same family for several decades, with the seller acquiring the property in the fall of 2025. This property offers a rare, if not once in a lifetime, opportunity to create your dream home by renovating this historic Lexington treasure in an exceptional location. Possession and closing date are negotiable. Kitchen and bathrooms are added to room count but have been gutted for potential remodel.

204 S Hanover Ave, Lexington
$685,000
4 Beds ⋅ 2 Baths ⋅ 26014251 MLS
This spacious duplex is located in the desirable Lakeview area and is convenient to parks, schools, dining, shopping, Chevy Chase & downtown Lexington. Each unit is all on one level and features a large Living Room with a decorative fireplace and open to the Dining Room. The Kitchen offers white cabinetry, newer stainless refrigerator and dishwasher (in main level unit). Also, there are 2 nice Bedrooms and a full Bathroom. Both units offer hardwood floors, and the main level has fresh paint. Both units have the same floor plan and each has a great screened back porch overlooking a large treed backyard perfect for picnics and relaxing. The nice 2 car garage is an added special feature and equally valuable is a full basement with 2 sets of washer/dryers hook ups and plenty of space for storage. Weather you are looking for an owner- occupied opportunity, investment property or multi-generational living, this duplex presents a wonderful opportunity. Being sold "as is".

1928-1930 Fontaine Rd, Lexington
$575,000
4 Beds ⋅ 3 Baths ⋅ 26015879 MLS
Welcome to this beautiful classic bungalow in the heart of Ashland Park, just steps from Slashes Park and minutes from Chevy Chase, Graeter's Ice Cream, and Starbucks. Enjoy the charm of the inviting front porch and a bright, open main level featuring spacious living and dining areas, an updated kitchen, three bedrooms, and two full baths. Upstairs offers a versatile bonus room ideal as a fourth bedroom, office, or flex space. Previous seller indicated upgrading to triple-pane windows and added a Mitsubishi ductless mini-split system. The unfinished basement with a full bath provides excellent storage and future potential. Outside, you'll love the large, flat backyard with a deck and an oversized two-car garage. This move-in-ready home combines classic charm, modern updates, and an unbeatable location in one of Lexington's most desirable neighborhoods.

321 Mcdowell Rd, Lexington
$2,490,000
5 Beds ⋅ 6 Baths ⋅ 26001074 MLS
Offered for the first time since its construction in 1966, 1361 and 1357 East Cooper Drive represent a truly exceptional opportunity to acquire a legacy property at the end of a quiet cul-de-sac in one of Lexington's most sought-after neighborhoods. Held by the same owner for nearly six decades and never before offered for sale, this is a property of remarkable scale, privacy, and long-term potential. The combined estate encompasses 1.14 acres of gently situated land and features a substantial residence totaling 6,981 square feet. The home offers a solid foundation with generous room sizes, multiple living areas, and a layout well-suited for thoughtful renovation, expansion, or reimagining to meet modern living standards. It presents a rare canvas for buyers seeking to create a custom residence in an established, high-value location. Tucked away at the end of East Cooper Drive, the setting provides an uncommon level of privacy and tranquility, surrounded by mature landscaping and neighboring homes that reflect long-term pride of ownership. Opportunities to acquire this amount of acreage and square footage in such a desirable Lexington location are exceedingly rare, particularly with the added flexibility of two parcels. This offering is ideal for buyers seeking a one-of-a-kind property with history, scale, and exceptional upside - an estate with the bones, location, and land to support a truly extraordinary transformation.

1357-1361 E Cooper Dr, Lexington
$195,000
1 Beds ⋅ 1 Baths ⋅ 26016139 MLS
One bedroom, one bath condo located at 101 South Hanover Avenue in downtown Lexington. The building offers secure weekday entry monitored by a doorman, two interior recreation areas for social use, and a rooftop patio with panoramic views of the Ashland Park area and the Lexington skyline. Inside the unit has the original parquet flooring that is extra thick for long life. There is a bonus division of the living space creating a sunroom effect. 3 French doors allow the bonus room to flow back into the main living area if desired. The unit is painted and ready for immediate occupancy. The building provides private laundry facilities, an on site fitness room, and a dedicated storage unit. A professional hair salon is located within the building for added convenience. The HOA includes all utilities except internet and streaming services. This location offers close proximity to area parks, services, and dining. Ashland, The Henry Clay Estate, is approximately 0.3 miles away, and Woodland Park is approximately 0.5 miles from the building. Nearby everyday conveniences include Kroger and Walgreens, both within roughly 0.5 miles. The property is also located near multiple Lexington restaurants along East Main Street, Ashland Avenue, and the Chevy Chase corridor.

101 S Hanover Ave Unit 8D, Lexington
$810,000
4 Beds ⋅ 4 Baths ⋅ 26009965 MLS
Excellent investment opportunity. Stately brick 4-Plex on large corner lot directly across from Ashland, The Henry Clay Estate. Four 1 bedroom, 1 bath units offer central A/C, hardwood floors, basement with laundry and storage. Covered off street parking. Many updates include, New roof and gutters 2024, three new HVAC systems 2024, 2025. Desirable location convenient to Chevy Chase, UK, Downtown, local shops, restaurants and more. Tenants will need 24 to 48 hours for notice,

137 Sycamore Rd, Lexington