Refine Search
Map
Sort by
$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
$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
$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
$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