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$665,000
5 Beds ⋅ 5 Baths ⋅ 1695612 MLS
Welcome to 104 Chestnut Glen Dr, a stunning one-owner, custom-built luxury home in the highly sought-after Chestnut Glen neighborhood of Louisville, KY. Perfectly situated on a prominent corner lot at the neighborhood's entrance, this brick-and-stone masterpiece offers over 6,000 square feet of refined living space, including a finished walk-out basement, dual primary suites, and an oversized three-car garage. From the moment you step into the grand two-story foyer flooded with natural light, you'll feel the quality and craftsmanship that define this home. Gleaming Italian marble floors, an elegant staircase, and architectural details like coffered ceilings and tray ceilings set a tone of timeless sophistication. A formal dining room with hardwood inlay is perfect for hosting, while the private main-level office creates an ideal work-from-home space. The gourmet kitchen features an open layout with a breakfast bar, casual dining area, and direct access to the expansive deckperfect for outdoor entertaining. The adjoining living room boasts soaring vaulted ceilings, a cozy fireplace, and large windows framing serene views. Off the kitchen, the laundry/mudroom connects to the three-car garage, adding everyday convenience. The main-level primary suite offers a spa-like retreat with an updated ensuite bath, while the second-floor primary suite provides equally luxurious accommodations. All bedrooms in this home are exceptionally spacious, each with oversized closets for remarkable storage. The walk-out basement includes a large bedroom with direct bathroom access, a family/game room with fireplace, a wet bar, and double doors leading to a covered patio. Additional unfinished space offers even more storage or room for future expansion. Situated on nearly half an acre with mature landscaping, sidewalks, and a prime location, this Louisville luxury property offers the perfect blend of elegance, comfort, and functionality. With its dual primary suites, abundant storage, and flexible living spaces, 104 Chestnut Glen Dr is ideal for multi-generational living or anyone seeking a high-end home with exceptional design and attention to detail. Schedule your private showing today and experience the best of Louisville luxury living in this remarkable Chestnut Glen residence.

104 Chestnut Glen Dr, Louisville
$660,000
7 Beds ⋅ 4 Baths ⋅ 1725607 MLS
OPEN HOUSE 8/9/26 12-2PM. Welcome to 111 Chestnut Glen Drive, a 7 bedroom, 3.5 bath estate offering nearly 4,500 finished square feet in one of East Louisville's most sought-after neighborhoods. Thoughtfully designed for both everyday living and exceptional entertaining, this home blends timeless architecture with generous living spaces throughout. A stately stone exterior, manicured landscaping, and inviting front porch lead to a dramatic foyer with hardwood flooring, elegant millwork, and a formal dining room. The two-story great room features soaring vaulted ceilings and a wall of windows overlooking the private, wooded backyard. The chef's kitchen is equipped with custom cabinetry, stainless steel appliances, a six-burner gas cooktop, and an oversized center island, while the cozy, adjoining hearth room offers a beautiful stone fireplace for more intimate gatherings. The spacious first-floor primary suite is a true retreat with triple tray ceilings, backyard views, a luxurious ensuite bath with a jacuzzi tub, frameless walk-in shower, dual vanities, and an impressive custom walk-in closet. Upstairs are four generously-sized bedrooms, including vaulted ceilings, Palladian windows, sitting areas, and charming Juliet balconies overlooking the great room. The finished walkout basement provides incredible flexibility with a large recreation room, kitchenette, dining area, custom built-in library shelving, two additional bedrooms, and a 3rd full bathroom, making it ideal for guests, multigenerational living, or extended entertaining. Meanwhile, the unfinished section adds abundant storage solutions, as well as possible workout area (or, alternatively, it's current setup: a golf simulator!). Outside, multiple levels of decking overlook beautifully landscaped, grounds where winding stone pathways lead through mature trees to a secluded stone patio with a brick fire pit, creating an unforgettable setting for relaxing or entertaining. Meanwhile, the outdoor sprinkler system makes lawn maintenance a breeze! An attached two-car garage—featuring a Tesla charger!—completes this exceptional property. Chestnut Glen's central location means your family retains the convenience of nearby access to ample shopping, dining, and entertainment options (a new Publix just opened within walking distance!), while still retaining safety and security of a quiet, low-traffic, Mayberry-like community. Rarely does a home offer this combination of space, craftsmanship, privacy, and convenience. Experience one of East Louisville's finest opportunities at 111 Chestnut Glen Drive.

111 Chestnut Glen Dr, Louisville
$650,000
5 Beds ⋅ 3 Baths ⋅ 1699902 MLS
This custom built one owner walk-out ranch with 5 bedrooms, and 3 full baths offers everything you need for comfortable living in a wonderful neighborhood. The main floor has white oak hardwood throughout the living and bedroom areas with tile in the bathrooms and laundry room. The primary bedroom is conveniently located on this floor, along with an updated primary bath, laundry room, great room with gas fireplace, dining room, kitchen, separate pantry, and 2 bedrooms (one of which is currently used as a home office), and full bath. The kitchen, which includes space for casual dining, was completely redone in 2021 with custom maple cabinetry and Caesarstone Luxury Quartz. Appliances are 2020 Bosch refrigerator, 2020 Bosch dishwasher, 2022 Bosch Dual Fuel (gas cooktop, electric oven and 2021 GE microwave. This level also has an extensive deck with a screened area for outdoor dining. The hardwood continues down extra wide stairs to the lower level. With 12-foot ceilings it does not feel like a basement! The large living area features a gas fireplace, bar, full size refrigerator, and windows overlooking the lower-level deck and wooded back yard. This level contains 2 bedrooms, one of which has 2 full closets and is currently used as a workout room with plenty of space for exercise equipment. Another full bath is located on this level. The lower level also has a spacious unfinished area with room for a workshop, tool storage and another large closet. There is also a custom loft storage area you will not find in any other home. A separate room houses the mechanicals which include a separate HVAC system for each level, as well as a whole house humidifier. The all-brick exterior has a new roof (2023) and new front door & sidelights (2022). There is an outside entrance with separate steps leading to a massive storage area over the garage. There are 3 separate garage doors leading to an extra-large 3-car garage. Other additional features include irrigation and security systems and fiber optic internet. Don't miss your opportunity to own this unique property!!

113 Chestnut Glen Dr, Louisville