Chestnut Glen Real Estate

Chestnut Glen Real Estate

Welcome to Chestnut Glen, a hidden gem nestled in the heart of Louisville, Kentucky, within the vibrant Jefferson County. This charming subdivision seamlessly blends suburban tranquility with urban convenience, making it an ideal place for families, professionals, and retirees alike.

Chestnut Glen is characterized by its beautifully landscaped streets, lined with mature trees and an array of stunning homes that reflect a variety of architectural styles. Each residence boasts spacious layouts, modern amenities, and inviting outdoor spaces, perfect for entertaining or enjoying a quiet evening under the stars. The community is designed to foster a friendly atmosphere, where neighbors become friends and families can thrive.

One of the standout features of Chestnut Glen is its prime location. Residents enjoy easy access to a plethora of shopping, dining, and entertainment options. Just a short drive away, you’ll find the bustling East End, with its trendy boutiques, gourmet restaurants, and family-friendly attractions. For outdoor enthusiasts, the nearby parks and recreational facilities offer ample opportunities for hiking, biking, and enjoying nature.

Education is a top priority in Chestnut Glen, with highly-rated schools nearby that provide quality education and a nurturing environment for children. The community’s commitment to family values and safety makes it a sought-after destination for those looking to establish roots in Louisville.

Experience the warmth and charm of Chestnut Glen, where community spirit meets modern living. Discover your dream home in this delightful subdivision and become a part of a neighborhood that truly feels like home.

Newest Listings in Chestnut Glen

$674,900
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

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