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227 Mcdowell Rd, Lexington
$879,900
3 Beds ⋅ 2 Baths ⋅ 26028147 MLS
Charming curb appeal meets modern updates in this classic Foursquare brick home, nestled in the highly sought-after Ashland Park neighborhood! Step inside to find tall ceilings and gorgeous hardwood floors flowing seamlessly through the spacious main level and upstairs. The inviting formal living room features a cozy fireplace with gas logs, perfectly complementing a spacious formal dining room for effortless entertaining. At the heart of the home is a beautifully updated kitchen featuring an abundance of cabinets offering plenty of storage, anchored by a large kitchen island that is perfect for hosting holiday gatherings and offers comfortable bar stool seating. This exceptional space opens seamlessly to a comfortable family room off the back, creating the ultimate layout for both everyday living and effortless entertaining. Upstairs, you will find spacious bedrooms and a beautifully updated full bathroom with a large walk in closet. Peace of mind comes easy with a new roof installed in 2023. Outdoor living is a breeze on the private back deck overlooking a deep backyard. Unfinished basement great for storage!! Complete with a one-car detached garage, this captivating property truly has it all

227 Mcdowell Rd, Lexington
108 Desha Unit A, B, C, & D, Lexington
$830,000
5 Beds ⋅ 4 Baths ⋅ 26028420 MLS
Impressive fourplex in Ashland Park with 1st floor 2 bedroom unit. Beautiful Hardwood floors, tile bathrooms, off street parking, individual basement laundry and storage areas. Current leases: Unit 1, 1 bedroom, 1 bath $1,100 through June 2027, Unit 2, Larger 2 bedroom, 1 bathroom, currently vacant, Unit 3, 1 bedroom, 1 bathroom, $1,100 through April 2027, and Unit 4, $1,075, 1 bed, 1 bath, through June 2027. Seperate utilities, central heat and air for each unit.

108 Desha Unit A, B, C, & D, Lexington
1108 Fincastle Rd, Lexington
$675,000
3 Beds ⋅ 2 Baths ⋅ 26027314 MLS
Craftsman beauty in the heart of Ashland Park—and an exceptional opportunity to make this special property your own. Lovingly maintained by the same owners for almost 30 years, this home retains many of the timeless architectural details that make a Craftsman so special; broad eaves, original hardwood floors, tall ceilings, built-in shelving and a dreamy full-length front porch. The natural light throughout is phenomenal. The renovated kitchen was carefully designed for a chef, with a gas range, lots of counter space and plenty of custom cabinetry. Spacious first-floor living includes a large living room with cozy fireplace, dining room AND a sunny family room with built-ins and a wall of windows overlooking the private backyard. Upstairs are three absolutely charming bedrooms with surprisingly generous closet space, a full bath and an additional large closet. The unique, original porte-cochère with convenient access from the front porch is the icing on the cake. Great bones, wonderful proportions, incredible character and one of Lexington's most beautiful, tree-filled neighborhoods. Walk to all the urban shopping and dining options in Chevy Chase, then stroll over to the Henry Clay Estate just blocks away to soak up the fall beauty.

1108 Fincastle Rd, Lexington
101 S Hanover Ave Unit 7B, Lexington
$340,000
2 Beds ⋅ 2 Baths ⋅ 26027223 MLS
Enjoy effortless one-level living in this beautifully situated seventh-floor condominium at Hanover Towers, overlooking the treetops of coveted Ashland Park. This spacious two-bedroom, two-bath residence features an open floor plan filled with natural light and lovely elevated views. With elevator access and everything conveniently located on one level, this home offers the perfect combination of comfort and ease. The open living and dining areas provide wonderful space for entertaining or simply relaxing above the canopy of one of Lexington's most treasured neighborhoods. Residents of Hanover Towers also enjoy access to a rooftop patio with sweeping views of downtown Lexington—an ideal spot to gather with friends, enjoy an evening cocktail, or take in the city skyline. Step outside and enjoy the charm and convenience of Ashland Park and Chevy Chase, with favorite restaurants, shopping, coffee shops, entertainment, and neighborhood amenities just moments away. Enjoy low-maintenance condominium living on the 7th level, without street noise, beautiful views, and one of Lexington's most desirable in-town locations.

101 S Hanover Ave Unit 7B, Lexington
1056-1058 Fontaine Rd, Lexington
$725,000
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
1820 Richmond Rd, Lexington
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 26024479 MLS
Single-Level living at its finest! Welcome to 1820 Richmond Road, an exceptional 4 bedroom, 3 bath residence on a beautiful half acre lot in one of Lexington's most desirable neighborhoods, directly across from Idle Hour Country Club. Extensively remodeled from floor to ceiling, this home pairs timeless character with modern finishes and thoughtful conveniences. All four bedrooms and three full bathrooms are located on the main level, offering the ease and functionality of single level living. The brand new kitchen, renovated bathrooms, refinished hardwood floors, and custom crown molding showcase the quality of the renovation, while integrated Bluetooth speakers, heated bathroom features, and custom built ins add distinctive touches throughout. The partially finished basement features an inviting entertainment room with a gas fireplace, along with abundant storage, complemented by a walk up attic with finished flooring for even more room to organize and store belongings. Outside, the spacious half acre lot offers privacy and room to enjoy, while the composite deck and enclosed sunroom provide inviting spaces for relaxing or entertaining with minimal upkeep. A two car garage with an EV charging port adds modern convenience. With its exceptional storage, low maintenance outdoor features, and thoughtfully designed main level, 1820 Richmond Road offers a rare combination of comfort, functionality, and space in a premier Lexington location.

1820 Richmond Rd, Lexington
211 Mcdowell 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
101 S Hanover Ave Unit 5B, Lexington
$345,000
2 Beds ⋅ 2 Baths ⋅ 26019887 MLS
Welcome to Hanover Towers 5B! This beautiful condo was FRESHLY PAINTED throughout as of October 15, 2026 and is move-in ready! This 2 bedroom, 2 full-bathroom condo features several thoughtful updates made by the current owner. Upon entering you will notice the open floor plan with a large living room that opens to the kitchen and dining areas. During recent kitchen renovations a wall was removed to create a large breakfast bar that opens to the main living area. New granite countertops, cabinets, an updated tile backsplash, new flooring and stainless steel appliances complete this more spacious kitchen area. Updated LED light fixtures in the kitchen create a modern look. The large glass doors were removed from the sunroom, creating a more spacious and uninterrupted living room with ample natural light and beautiful views of treelined, Hanover Avenue. The hallway to the bedrooms has been opened up for easier access to both bedrooms and the guest bathroom. The primary bathroom has a new, easy access, walk-in shower with a rainwater shower head, push-button controls, and a handheld spray. There are many closets and shelves throughout the condo and a storage closet for each unit in the basement. Hanover Towers 5B is more than just a 1305 sqft condo, there are several places to gather with neighbors and friends, including comfortable seating areas in the lobby and a beautiful rooftop patio with amazing city views. Exercise and Laundry facilities are in the basement. From the downstairs entry to the rooftop views, and a convenient location in a wonderful neighborhood, Hanover Towers is sure to delight. *3 images are virtually staged*

101 S Hanover Ave Unit 5B, Lexington
262 S Ashland 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
101 S Hanover Ave Unit 2M, Lexington
$344,900
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
305 Sycamore Rd, Lexington
$790,000
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
1014 Richmond 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
1897 Hart Rd, Lexington
$1,779,000
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
204 S Hanover Ave, 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
1928-1930 Fontaine Rd, 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
101 S Hanover Ave Unit 8D, 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. Carport spaces may be available at an extra cost. They do not convey with the purchase of the property but must be applied for.

101 S Hanover Ave Unit 8D, Lexington

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