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$725,000
4 Beds ⋅ 2 Baths ⋅ 26019486 MLS ⋅ 2,580 SqFt. ⋅ ACTIVE Status
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
$359,900
2 Beds ⋅ 2 Baths ⋅ 26019062 MLS ⋅ 1,305 SqFt. ⋅ ACTIVE Status
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 ⋅ 4,032 SqFt. ⋅ ACTIVE Status
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 ⋅ 5,474 SqFt. ⋅ ACTIVE Status
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
$1,895,000
4 Beds ⋅ 6 Baths ⋅ 26010477 MLS ⋅ 5,261 SqFt. ⋅ ACTIVE Status
Contemporary design meets Ashland Park in this thoughtfully crafted ranch set on beautifully landscaped grounds, with designer finishes throughout. Built for entertaining, the indoor and outdoor spaces flow seamlessly together. An expansive covered front terrace with an Ipe ceiling connects easily to the open kitchen, dining, and living areas, creating a natural gathering space. The kitchen is designed with both style and function in mind, featuring European-style Mouser cabinetry, an impressive island, and quartz surfaces that extend to the ceiling for a dramatic effect, along with high-end appliances. Oversized casement windows bring in natural light and enhance the clean, modern feel. The living room is anchored by a cantilevered quartz fireplace, framed by large windows that fill the space with light. The first-floor primary suite offers a spacious layout with a fully tiled quartz shower and a well-appointed walk-in closet. The main level also includes a second bedroom with an en suite bath, along with a laundry area and a convenient drop zone. The finished basement provides additional room to gather, featuring a second living area with a bar. Two additional bedrooms with en suite baths and walk-in closets, along with multiple flex spaces, complete the lower level. A rare opportunity in Ashland Park, offering a prime location with a strong focus on design, comfort, and livability.

1897 Hart Rd, Lexington
$799,000
3 Beds ⋅ 4 Baths ⋅ 26014485 MLS ⋅ 3,491 SqFt. ⋅ ACTIVE Status
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 ⋅ 2,870 SqFt. ⋅ ACTIVE Status
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
$195,000
1 Beds ⋅ 1 Baths ⋅ 26016139 MLS ⋅ 805 SqFt. ⋅ ACTIVE Status
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 ⋅ 3,222 SqFt. ⋅ ACTIVE Status
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