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1337 Cooper Dr, Lexington
$1,560,000
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

1917 Hart Rd, Lexington
$1,475,000
4 Beds ⋅ 5 Baths ⋅ 25506736 MLS
Discover refined one-level living in this updated mid-century modern ranch located in Ashland Park neighborhood just minutes from downtown Lexington and the University of Kentucky. This spacious 4-bedroom, 3-full-bath, 2-half-bath home blends iconic style with today's luxury amenities. Step inside to a sun-filled layout featuring expansive natural light, clean architectural lines, and exceptional entertaining spaces. The chef's kitchen is a true standout, equipped with Thermador appliances, a large island, and seamless flow to the dining and living areas. A stylish wet bar elevates gatherings with ease. The primary suite offers comfort and convenience with dual closets and a beautifully updated bath. Additional bedrooms are generously sized, and the flexible floorplan provides room for work, guests, and leisure. Enjoy outdoor living on the screened-in porch, overlooking an impressive backyard retreat. The property features an outdoor kitchen, in-ground heated saltwater pool, and fire pit, perfect for relaxing or entertaining. A rare 4-car garage provides exceptional storage and hobby space. Modern updates, timeless design, and an unbeatable location make this Hart Road property a truly special offering.

1917 Hart Rd, Lexington

1305 Cooper Dr, Lexington
$1,334,000
5 Beds ⋅ 3 Baths ⋅ 26018019 MLS
Fabulous opportunity to own a classic Ashland Park home on an over half acre lot! Offering five bedrooms, three bathrooms, a lovely screened porch and over 3,000 finished square feet over three floors. Step on to the inviting front porch and in to the lovely foyer. To your left are formal living and dining rooms with a fireplace that open to the screened porch. In the center of the home is the updated kitchen with gas range and breakfast bar. The first floor primary bedroom has an en suite bath, and there are two additional bedrooms (one currently used as a home office) and a full hall bath to complete the first floor. Upstairs, you will find two generously sized bedrooms and another full bath. The lower level recreation room that opens to the backyard boasts built-ins, a second fireplace, two car garage and an abundance of storage. The backyard with mature landscaping offers lots of privacy. A truly special home.

1305 Cooper Dr, Lexington

269 S Hanover Ave, Lexington
$1,200,000
4 Beds ⋅ 5 Baths ⋅ 25506504 MLS
Historic Ashland Park! Lovely, recently renovated home just steps away from dining, shopping and schools in the popular Chevy Chase/Ashland Park neighborhood. Features include an inviting front porch, hardwood floors, first level living room, dining room, and family room open to a stylishly decorated kitchen - perfect for entertaining! The second level offers the spacious primary suite with large closets, beautiful bath and laundry area, plus 2 additional bedrooms and baths. The third level is perfect for another bedroom, office or upstairs family room! The basement features a rec room, half bath and laundry room. The fenced backyard has a professional sound system, landscape lighting with lovely landscaping - the perfect spot to host your family and friends for dinner! Additional features include abundant parking with a one-car garage, 4 permitted spots in front of the house, and alley access for additional parking. Conveniently located to downtown Lexington and the University of KY. A few minutes stroll away from Bella Cafe, Omakase, the Obstinate Son, Bear and the Butcher, Josie's, Char, Starbucks and CCI!

269 S Hanover Ave, Lexington

100-102 S Hanover Ave, Lexington
$900,000
12 Beds ⋅ 6 Baths ⋅ 25501231 MLS
Step back in time with this Ashland Park charmer. Built in 1929, this six-unit apartment building was said to have been one of the first steel structure apartments built in Fayette County. The adjacent duplex was designed to be on top of this building as the fourth and fifth levels. Each apartment offers hardwood floors, high ceilings, unique built-ins, living room, dining room, kitchen, 2 bedrooms, and a full bath. There is a shared laundry and individual storage areas in the lower level. The Seller is providing a $200,000 KY Heritage Council historic tax credit that can be passed along to the Purchaser. It can be used as early as June 2026 with a 3-year deadline ending July 2029. The adjacent duplex is also available. Located steps away from Chevy Chase shopping and restaurants, downtown Lexington, the University of KY, and Ashland, the Henry Clay Estate!

100-102 S Hanover Ave, Lexington

293 S Ashland Ave, Lexington
$885,000
4 Beds ⋅ 3 Baths ⋅ 26012811 MLS
Shaded by a canopy of towering, mature trees, this circa-1905 Victorian farmhouse sits gracefully on the corner of one of Lexington's most coveted streets. The wraparound porch and unique architecture welcome you with turn-of-the-century charm, all while located mere steps away from dozens of modern conveniences...Woodland Park, Chevy Chase shops, delicious restaurants, excellent schools and so much more. This thoughtfully designed floor plan balances historic character with comfortable livability. The first floor features a grand 2-story foyer, cozy family room, formal living room, spacious dining room - perfect for large gatherings, a stylish kitchen, full bathroom, and private laundry w/ secondary staircase to second floor. Upstairs, the second level offers a spacious primary bed+bath w/ a private home office or walk-in closet, 3 additional bedrooms and a fully remodeled hallway bath. Outside you'll find lush landscaping, a white picket fence and large trees creating a private and picturesque retreat. Enjoy evenings entertaining family and friends on the secluded rear patio after an easy stroll home from dinner or a day at the park. Storage is abundant here with an unfinished basement and huge second floor loft over the 2 car detached garage. The current owner's meticulous updates throughout have restored and preserved the home's original character - see attached list. Don't miss the original hardwood floors, hidden pocket doors, intricate millwork, SIX fireplaces and authentic charm that simply cannot be replicated.

293 S Ashland Ave, Lexington

306 Irvine Rd, Lexington
$850,000
3 Beds ⋅ 2 Baths ⋅ 25506614 MLS
Welcome to 306 Irvine Rd, tucked right into the heart of Ashland Park, one of Lexington's most iconic and sought-after neighborhoods. This beautifully maintained 3-bedroom, 2-bath home offers 2,032 sq ft of charm, character, and comfort, all wrapped in that classic 40502 vibe buyers are hunting for. Step inside to a warm, inviting living room with a cozy fireplace, perfect for winding down or hosting friends. Enjoy slow mornings on the covered front porch or step out back and unwind on the oversized deck with a clear view of your own private backyard retreat. Sitting in the coveted Morton Middle and Henry Clay High School districts, this home puts you minutes from Chevy Chase, downtown Lexington, boutique shopping, local dining, parks, and everything that makes Ashland Park such a gem. The area's tree-lined streets and historic character speak for themselves. Homes in this pocket don't last, especially ones this well cared for. Don't miss your chance to make a move into one of Lexington's premier neighborhoods.

306 Irvine Rd, Lexington

122 S Hanover Ave, Lexington
$775,000
4 Beds ⋅ 4 Baths ⋅ 26010528 MLS
Ashland Park stately brick 4-Plex investment or potential for individual ownership or make this a single family home! Convenient to Downtown, Chevy Chase, UK, Henry Clay Estate, Kenwick Table, local shops, restaurants and more.Each unit has hardwood floors, individual central heat/air, spacious closets, outside decks/porches, 3 garage spaces and driveway for at least 2 additional cars.First floor units1 & 2 have living room, bedroom and kitchen, front entrance and rear exits and front porch access.Second floor unit 3 has living room, formal dining room, large kitchen, bath, bedroom and access to the large deck off the rear, front entrance and rear exit. Second floor unit 4 has living room, kitchen and bath and the 3rd floor large bedroom and office area with deck off the rear. Property has 3 car garage, full shared basement with storage and laundry (Coin operated could be installed) Roof and garage doors are 5yrs old, 1 HVAC unit replaced 2025, rebuilt front porch roof 2026, exterior painted 2026. Property is in Historic H-1 overlay requiring approval for exterior changes.24-48 hr notice. All tenants would like to continue. Units 1 ($1000),2 ($1150),4 ($1300) are month to month. Unit 3 lease ends Sept 1, 2026.Rental amounts of units 3 and 4 are under typical market rent. Listing agent is owner.

122 S Hanover Ave, Lexington

109 Irvine Rd, Lexington
$700,000
3 Beds ⋅ 2 Baths ⋅ 26009798 MLS
Classic elegance and timeless character define this 3-bedroom, 2-bath bungalow in the heart of Ashland Park. Built in 1924 this property is filled with nods to days gone by while offering spacious, comfortable living, refined to present day. The main level features two generously sized bedrooms and two full baths, along with a cheerful sunroom perfect for everyday living and entertaining. Hardwood floors run through the majority of the first floor, complementing the formal living room with its cozy fireplace and beautiful built-in cabinetry. The large dining room is ideal for gatherings and offers lovely views of the extraordinary spring foliage and expansive side yard. Upstairs, the third bedroom offers flexible space for a private owner's retreat, studio, office, or den. Plenty of storage here including a walk-in cedar closet. The kitchen is spacious and offers plenty of storage and space to dine. From there you will find the sunroom, wrapped in windows, inviting much natural light and providing direct access to the fenced backyard and stone patio—an ideal setting for relaxing or hosting. This peaceful, private space is enhanced by the garden, creating a truly serene outdoor haven. A signature stucco columned front porch welcomes you home and sets the scene for quiet summer evenings. Nestled along a picturesque, tree-lined street, this home is just moments from downtown Lexington, Ashland Plaza, local restaurants, shopping, and community events—offering exceptional access and convenience. Located in one of Lexington's most revered historic neighborhoods, Ashland Park—home to the estate of Henry Clay—this is a rare opportunity to own a piece of the city's rich heritage.

109 Irvine Rd, Lexington

321 Mcdowell 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

101 S Hanover Ave Unit 5A, Lexington
$325,000
2 Beds ⋅ 2 Baths ⋅ 26009139 MLS
Located on the highly sought-after, tree-lined South Hanover Avenue in Ashland Park, this 2 bedroom, 2 bathroom residence offers an exceptional walkable lifestyle to local shops, restaurants, parks and downtown. Residents are welcomed by a secure entry with doorman and an elegant lobby, perfect for gathering with friends. Take the elevator to the fifth floor, where a beautifully renovated hallway leads to Unit 5A. Inside, you'll find timeless parquet flooring, a dedicated dining area, a well-appointed kitchen with stainless steel appliances, a spacious living room and a light-filled tiled sunroom with beautiful views of downtown Lexington. The generous primary suite features an en-suite bath, built-in shelving and a walk-in closet. The large second bedroom also includes a walk-in closet and is adjacent to an additional full bathroom. Large family room, dining space and sunroom complete the layout of the spacious unit. The HOA includes all utilities, a doorman for added security, a storage unit in the basement, plus access to a rooftop terrace ideal for entertaining, as well as convenient access to exercise, laundry and storage areas on the building's lower level. Experience easy, low-maintenance living in one of Lexington's most desirable neighborhoods!

101 S Hanover Ave Unit 5A, Lexington

101 S Hanover Ave Unit 4D, Lexington
$218,000
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

101 S Hanover Ave Unit 8K, Lexington
$192,000
1 Beds ⋅ 1 Baths ⋅ 26003152 MLS
Experience the height of luxury at downtown's most prestigious address 101 South Hanover Avenue. This upscale residence offers a lifestyle of security and sophistication, beginning with an extravagant secure entry monitored week days by a doorman and featuring two elegant recreation areas perfect for enjoying social gatherings plus a rooftop patio. Would be ideal for a young professional or a part time resident with zero maintenance. Inside this polished one-bedroom, one-bathroom retreat, you'll find modern refinements throughout, including newer luxury vinyl plank flooring, wide plank window blinds, updated hardware, and contemporary lighting. The kitchen is equipped with a newer refrigerator and food disposal, while the bathroom features a stylishly updated vanity. Step out onto the rooftop patio to take in breathtaking panoramic views of the historic Ashland Park area and the vibrant Lexington skyline. It is the perfect backdrop for morning coffee or sunset cocktails. Enjoy unparalleled amenities that simplify city living. The HOA includes all utilities, plus access to an on-site fitness room, private laundry facilities, and your own dedicated storage unit. For ultimate convenience, the building even hosts a professional hair salon on-site with experienced stylists. This is more than a condo; it is a lifestyle of ease and elegance. Great location easy stroll to the park at Ashland (Henry Clay's home) or Woodland Park, Kroger, Walgreens and not to mention some of Lexington's best restaurants...Char on Ashland, Cole's, Eppings, Bella Cafe, The Obstinate Son, and The Sage Rabbit!! But the list goes on and on....Lexington living at its best!! HOA covers all the utilities (except internet and streaming services).

101 S Hanover Ave Unit 8K, Lexington