Refine Search
Map
Sort by
$2,800,000
7 Beds ⋅ 8 Baths ⋅ 1703596 MLS
550 Fairfield Drive; recently sold off market. Nestled at the end of a quiet private street in Cherokee Gardens—one of Louisville's most prestigious neighborhoods—this exceptional residence offers the rare combination of in-town convenience and secluded privacy. Thoughtfully expanded on both sides and designed with uncompromising attention to detail, the home perfectly balances timeless Colonial architecture with modern luxury, creating an inviting environment for everyday living and extraordinary entertaining. A picturesque front walkway framed by lush, mature landscaping leads to a grand foyer where soaring ceilings and a sweeping staircase set an elegant tone. Inside, gleaming hardwood floors, arched openings, refined millwork, and abundant natural light reflect craftsmanship and sophistication throughout. The chef's kitchen unites style and function with a generous center island featuring an oversized prep sink and integrated butcher block cutting board. Premium appliances include a Wolf six-burner gas range, Sub-Zero refrigerator, refrigerator drawers, wine refrigerator, and ice maker. A walk-in pantry offers additional storage and custom cabinetry, while the sunlit breakfast room overlooks the serene backyard. The adjacent formal dining room provides an elegant setting for both intimate dinners and festive gatherings. Multiple living spaces deliver flexibility and comfort. Two side-by-side living rooms anchor the main level, each with a fireplace and built-in shelving. One space opens through French doors to a rear terrace and includes a full wet bar with beverage refrigerator and sinkperfect for effortless entertaining. The first-floor primary suite is a private sanctuary, featuring renovated his-and-hers baths and custom walk-in closets. A private staircase from the suite leads to an upstairs office and sitting room, offering peaceful views of the landscaped grounds and shimmering saltwater pool. The second level includes an additional ensuite bedroom, four generously sized bedrooms, and two stylishly updated baths. A private gym with an integrated sound system, dry sauna, steam shower, and full bath completes the upper level for the ultimate wellness experience. The lower level expands the living area with a spacious family room showcasing a striking stone fireplace, half bath, and extensive storageideal for casual entertaining or relaxing. Additional main-level features include a richly appointed office with private outdoor access to a quiet sitting area, perfect for morning coffee or working al fresco. A large laundry room offers abundant cabinetry, an additional Sub-Zero refrigerator, and utility sink. Directly opposite, the three-car garage is equipped with an EV charging station for modern convenience. Host unforgettable gatherings in a private outdoor oasis that blends comfort, space, and unmatched seclusion. Expansive terraces provide multiple areas for dining, lounging, and entertaining, while vibrant landscaping ensures privacy. A sparkling saltwater pool anchors the outdoor living area, creating a tranquil escape reminiscent of a private resort. Integrated sound and lighting systems elevate the experience, and a dedicated storage room adds functionality. This beautifully maintained estate presents an unparalleled opportunity to enjoy the best of both worldsseclusion and exclusivity, all within minutes of Louisville's shopping, dining, and cultural attractions. A rare blend of architectural integrity, luxurious amenities, and unmatched privacy in one of the city's most coveted neighborhoods.

550 Fairfield Dr, Louisville
$2,675,000
4 Beds ⋅ 5 Baths ⋅ 1720276 MLS
Sitting pretty on more than an acre in the coveted estate section of Cherokee Gardens, this classic Colonial is a rare find that checks all the boxes. See for yourself the beautifully updated living spaces and the park-like lot with mature trees, expansive flat green space, and resort-style outdoor amenities, including a putting green and a saltwater pool (less than a year old). A gracious foyer welcomes you into elegant formal living and dining rooms designed for both everyday living and entertaining, each offering beautiful views of the grounds. The light filled sunroom features walls of windows and French doors that open to a stunning limestone terrace. At the heart of the home is the ideal eat-in kitchen, complete with a large center island, bay-window dining area, walk-in pantry, and seamless flow into the inviting family room with fireplace and custom built-ins. Don't miss the handsome wood-paneled library tucked just off the front hall—a cozy spot for a fire and a book. A practical drop zone/mudroom back hall with a rear stair case and charming powder room complete the first floor. Upstairs, the spacious primary suite offers has spa-like renovated bath with dual vanities, walk-in closet, and an adjoining bonus room perfect for a home office, sitting room, nursery, or expanded dressing area. Three additional bedrooms, two full baths, abundant closet space, and a laundry room complete the second level. The third-floor bonus room works as a playroom, exercise space, or media room. The lower level, freshly updated with new paint and carpet, offers additional finished living space, a full bath, and generous unfinished storage. Soaring ceilings, random width pegged hardwoods, some newer windows, 4 car attached garage just to name a few. Thoughtfully improved over time, this move-in ready Cherokee Gardens gem seamlessly blends character, modern luxury, and comfortable everyday living on one of Louisville's most desirable streets. If we are fortunate enough to receive any offers, Seller requests they are submitted by Sunday 14th at 4pm with a response time of Monday the 15th at 4pm- thanks for understanding! Possession cannot be given until August 14th 2026.

500 Fairfield Dr, Louisville
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 1723337 MLS
Situated in the prestigious Cherokee Gardens neighborhood, this distinguished traditional residence blends timeless architecture, refined living spaces, and an exceptional location in one of Louisville's most coveted settings. Offering 4 bedrooms, 3 full baths, and 1 half bath, the home is thoughtfully designed with elegant spaces, sophisticated details, and a layout tailored for both elevated entertaining and comfortable living. A welcoming entry introduces warm and well-appointed interiors, where formal living and dining rooms provide elegant yet comfortable spaces for gatherings. The formal living room is especially charming with floor-to-ceiling built-in shelving and a gas fireplace. Hardwood floors extend throughout the main level, adding warmth and continuity throughout the home. Designed with both style and functionality in mind, the kitchen offers abundant cabinetry, generous prep space, a gas range, and a center island with bar seating. Just beyond, the spacious family room creates a natural gathering space with a second gas fireplace and abundant natural light. Direct access to the backyard creates seamless indoor-outdoor flow ideal for entertaining or everyday enjoyment. A private office offers flexibility for work or study, while a conveniently located half bath completes the main level. The primary suite serves as a relaxing retreat with a spacious walk-in closet featuring built-in shelving and an ensuite bath complete with a dual-sink vanity and tiled shower. Three additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests, while a hall closet offers the potential for conversion into a ventless washer and dryer space. The finished lower level offers exceptional flexibility with a cozy secondary family room featuring charming built-in bookshelves, creating the perfect setting for movie nights, a lounge space, or game-day gatherings. A separate area provides excellent space for a home gym, recreation room, playroom, or hobby space, while a full bathroom and generous storage add everyday convenience and functionality. Outside, the private backyard creates a peaceful setting for relaxing or entertaining, complete with a patio seating area and green space ideal for enjoying quiet mornings, outdoor dining, or evenings with guests. The detached two-car garage offers additional storage and practicality, while dual HVAC systems provide comfort and efficiency throughout the home. Perfectly positioned in the heart of Louisville's most sought-after in-town corridor, this exceptional property offers outstanding convenience with easy access to downtown, major interstates including I-64, I-65, I-71, and I-264, and some of the city's most beloved destinations. Enjoy close proximity to Cherokee Park, Seneca Park, the Crescent Hill Reservoir, and the vibrant Frankfort Avenue and Lexington Road corridors, known for their local dining, coffee shops, boutiques, and neighborhood favorites including Blue Dog Bakery & Cafe. Blending timeless charm with premier convenience, this home places you moments from the best of The Highlands, Crescent Hill, and St. Matthews living.

559 Sunnyside Dr, Louisville
$1,108,000
3 Beds ⋅ 3 Baths ⋅ 1696156 MLS
Tucked away in one of Louisville's most established neighborhoods, this beautifully updated ranch on Garden Drive offers refined living with generous spaces, thoughtful details, and a layout designed for easy entertaining. Every room feels intentional with natural light, custom finishes, and timeless style. A formal dining room just off the entry welcomes you with a stately fireplace and a wall of windows. The kitchen is both functional and inviting, with abundant custom cabinetry, updated lighting, and countertop seating. Off the kitchen, a large family room features built-in shelving around the fireplace and French doors that open to a covered porch with retractable screens. A second dining area connects to the porch as well, creating a natural flow between indoor and outdoor gathering spaces. A spacious mudroom with laundry and pantry is conveniently located just off the kitchen. A study connects to a bright great room with vaulted ceilings, offering another light-filled living space. The primary bedroom includes tray ceilings, a generous walk-in closet, and a comfortable en-suite bath with double vanities and built-in storage. A finished lower-level room offers flexible use for a home office, art studio, or playroom. The backyard is a true extension of the home, offering multiple areas for relaxation and entertainment. Thoughtfully designed with a built-in gas grill, stacked-stone prep area, a newly added bocce court, pea gravel sitting area, and open lawn surrounded by mature landscaping. A full-house propane generator offers peace of mind year-round.

596 Garden Dr, Louisville
$845,000
3 Beds ⋅ 4 Baths ⋅ 1700925 MLS
Welcome to timeless elegance in the heart of Cherokee Gardens. This stately two-story red brick residence combines classic architectural charm with modern comfort. Gracious, light-filled rooms and a seamless flow make this home ideal for both everyday living and sophisticated entertaining. The beautifully updated kitchen features sleek stainless steel appliances and opens to an inviting dining room, perfect for gathering with family and friends. Upstairs, you'll find three spacious bedrooms, including a serene primary suite with generous closet space and a luxurious marble-appointed bathroom boasting dual vanities, a glass-enclosed shower, soaking tub, and heated floors. The finished lower level provides exceptional versatility, offering a comfortable space for entertaining guests, a playroom, or a private retreat with a non-conforming bedroom and full bath. Step outside to enjoy the tranquility of mature trees surrounding your newly built deck, complete with an outdoor fireplace that's ideal for relaxing or entertaining year-round. Experience classic beauty and modern luxury in one of Louisville's most sought-after neighborhoods.

552 Sunset Rd, Louisville
$825,000
3 Beds ⋅ 3 Baths ⋅ 1693631 MLS
Nestled within the prestigious enclave of Cherokee Gardens, this extraordinary architectural masterpiece stands as a testament to the visionary genius of renowned architect Stratton Hammon. Seamlessly blending classical elegance with contemporary sophistication, this distinguished residence offers an unparalleled living experience that captivates from the moment you cross its threshold. The journey begins in the dramatic foyer, where soaring ceilings welcome you into a space accented by a magnificent curved iron staircase, ascending like a sculptural work of art. The spacious limestone-tiled entry sets an immediate tone of grandeur, hinting at the architectural treasures that await inside. At the heart of this remarkable home is the well-appointed kitchena culinary sanctuary where gleaming granite countertops complement carefully curated white cabinetry. Stainless steel appliances stand ready to assist in gastronomic pursuits, while the adjacent breakfast room provides an intimate setting for morning rituals and casual dining. The first floor unfolds as a symphony of thoughtfully designed living spaces, each with a distinct purpose yet seamlessly connected. The formal living room commands attention with its stately fireplace, creating an atmosphere of refined elegance perfect for sophisticated gatherings. Nearby, the family room offers a more relaxed ambianceideal for intimate conversations and quiet evenings. Arguably the most enchanting space on this level is the conservatorya sunlit sanctuary that blurs the boundaries between indoor and outdoor living. Flooded with natural light through abundant windows, this versatile room is perfect for dining or leisure. The crowning feature is its lantern roof, complete with a skylight cupola that transforms the space into a celestial observatory by day and night. A thoughtfully integrated dry bar adds convenience for entertaining, making this area ideal for intimate cocktail parties or peaceful afternoon relaxation. Adding to the first floor's appeal is a cozy bedroom, originally conceived by Stratton Hammon as a "lounge." More intimate in scale than other sleeping quarters, it offers flexibility as guest accommodation or a private retreat. A full bathroom on this level ensures convenience for residents and visitors alike. Ascending to the second floor reveals equally impressive accommodations, beginning with a versatile upper landing featuring abundant built-in storage closets. Whether transformed into a home office, library, art studio, or meditation space, this area offers endless possibilities for personalization. The secondary bedroom includes its own attached bathroom, ensuring privacy and comfort for family or guests. The primary bedroom suite epitomizes residential luxurya private sanctuary with a spacious marble bathroom featuring a soaking tub, separate shower, and double vanity. This retreat provides the perfect escape from daily demands, with generous proportions and thoughtful details that promote rest and rejuvenation. There is also potential for second-level expansion to add an additional bedroom. The exterior exudes character and comfort, framed by mature, beautifully landscaped gardens that offer both aesthetic appeal and privacy. A spacious stone terrace invites outdoor entertaining or tranquil moments in the sun, ideally positioned to enjoy the serene surroundings. A detached garage adds classic charm and functionality, complemented by an additional parking area suitable for guests or extra vehicles. The unfinished basement provides ample storage space. Located in a prime area, this residence offers both sophistication and convenience. Don't miss the opportunity schedule your showing today!

537 Garden Dr, Louisville
$802,500
4 Beds ⋅ 3 Baths ⋅ 1707700 MLS
Welcome to this Cherokee Gardens classic, offered for the first time and lovingly maintained by the same family for over 40 years. This home features four bedrooms, two and a half baths, and sits on nearly a quarter-acre lot. The first floor features random-width pegged hardwood floors in the spacious living and dining rooms, creating warmth and character. The kitchen offers custom 42-inch cherry cabinets and a charming breakfast nook. From both the breakfast room and the cozy den off the dining room, you can step out onto the back porch, perfect for relaxing or entertaining. The fenced backyard has long been a gardener's paradise and offers endless potential for outdoor enjoyment. Upstairs, you will find a generously sized primary suite with an adjoining bath, a rare feature for a 1941 traditional floor plan, along with three additional bedrooms and a full bath. An attached garage comfortably fits an SUV or two smaller vehicles. Abundant storage is available in both the attic and basement, and the basement also includes an egress door with direct access to the backyard. This is a rare opportunity to own a well-cared-for home full of charm and history, in one of the area's most beloved neighborhoods

602 Sunset Rd, Louisville
$782,500
5 Beds ⋅ 4 Baths ⋅ 1717364 MLS
Perched on an impeccably manicured lot with beautiful treetop views, this charming home is ideally situated in the heart of Cherokee Gardens, blending classic appeal with an outstanding location. Hardwood floors run throughout the formal living and dining rooms, while the kitchen features granite countertops, abundant storage, and a breakfast area that opens to a spacious family room with a fireplace. A large deck off the family room overlooks the picturesque landscape and treetops of Cherokee Gardens. The walkout lower level offers another expansive family room with a fireplace, large windows, and impressive ceiling height that make the space feel like first-floor living. The lower level also includes a bedroom with an egress window, a full bath, and an enormous walk-in closet, along with access to a beautiful patio overlooking the manicured backyard.Upstairs, you'll find a well-appointed primary suite, three additional bedrooms, and a generously sized full bath. Ideally located just steps from Seneca Park and minutes from St. Matthews dining, shopping, and everyday conveniences.

710 Daneshall Dr, Louisville
$747,000
3 Beds ⋅ 2 Baths ⋅ 1723232 MLS
Rare opportunity to own a ranch in the highly sought-after Cherokee Gardens neighborhood! Thoughtfully cared for and lovingly maintained, this home offers timeless style paired with valuable updates. Inside, you'll find hardwood floors throughout the home, a bright and inviting tiled sunroom, and a cozy carpeted den that provides the perfect additional living space. The kitchen is equipped with updated GE appliances, including a gas cooktop, making it both functional and stylish. Three generously sized bedrooms are served by two full hallway bathrooms, offering a practical layout for family and guests alike. An oversized two car attached garage and unfinished basement provide convenience and ample storage. Significant recent improvements provide added peace of mind, including a new roof and gutters (2021), Hardie Board exterior trim (2026), fresh exterior paint (2024), chimney tuckpointing with a new cap, and a newer water heater (2022). Be sure to see the list of improvements in the property disclosure! Perfectly situated across from Seneca Park and featuring a charming patio overlooking Sunnyside Drive, this home offers an unbeatable combination of location, comfort, and convenience. Don't miss your chance to make this meticulously cared-for Cherokee Gardens gem your own!

3027 Beals Branch Dr, Louisville
$730,000
4 Beds ⋅ 3 Baths ⋅ 1704827 MLS
OPEN SUN 12/7 from 2 - 4 Step into a cherished family home filled with nostalgia, classic charm, and endless potential. Situated on a .41-acre lot in the highly desirable Cherokee Gardens, this uniquely designed 4-bedroom, 3-bath residence features a first-floor primary suite, first-floor laundry, and an unfinished basement offering ample storage or future expansion. The light-filled screened and glass-enclosed patio overlooks the serene backyard—perfect for quiet mornings or evening gatherings. Additional highlights include a 2-car attached garage and a whole-house generator for peace of mind. Lovingly maintained and turn-key ready, this home is prepared to welcome its next chapter.

520 Garden Dr, Louisville
$422,500
3 Beds ⋅ 3 Baths ⋅ 1712842 MLS
Lovely move in ready brick home in wonderful location tucked away in the Highlands! Covered front porch welcomes you into the spacious living room with fireplace and adjoining dining room. Warm hardwood floors throughout and lots of natural light make the home cozy and bright! The kitchen has lots of counter space and stainless steel appliances and entrance to the covered back patio. Large first floor primary bedroom and updated bathroom complete the first floor. Right off the kitchen are the steps to 2nd floor with two very generous sized bedrooms, one with glass doors to back rooftop and a very nicely updated full bathroom with bathtub. The basement has a large finished family room with space for office, playroom, exercise, etc. There is a laundry room with lots of storage. Outside there is a nice size fully fenced yard with privacy fence for play, gardening etc. Two car detached garage with large driveway makes parking a breeze with lots of extra room for storage. You don't want to miss this amazing home in a great, private and established neighborhood in the Highlands close to all the shopping, entertainment and convenience of the city!

2222 Walterdale Terrace, Louisville
$145,000
1 Beds ⋅ 1 Baths ⋅ 1705988 MLS
Welcome to Cherokee Gardens! This rare gem is located in the vibrant Highlands neighborhood, nestled between the serene Cherokee Park and the bustling Bardstown Road. This 1-bedroom, 1-bath condo has been tastefully updated with granite countertops, stainless steel appliances, designer finishings, and renovated bathroom. Through large sliding glass doors from the living room is an enclosed sun room, perfect for an office, reading room, or flexible bonus room. Enjoy exclusive amenities including the refreshing pool, meticulously maintained grounds, an on site laundry facility, and off street parking lot. Whether you're looking for your next home or an investment, don't miss your opportunity to to see this move in ready home, right in the heart of the Highlands!

1040 Cherokee Rd Unit APT F6, Louisville