111 Chestnut Glen Dr, Louisville, KY 40245

• 7 beds |
• 4 baths |
• 4,446 sqft

Property Description

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.

Listing Status:

Active

Date Added:

August 6, 2026

Data Last Updated:

August 7, 2026 at 2:37AM

Listing Office:

RE/MAX Results : 502-253-9100

MLS ID:

1725607

Interior

• Basement: Walkout Finished
• A/C: Central Air
• Heating: Natural Gas
• Fireplace: FireplaceFireplaces: 1

Exterior

• Style: Traditional
• Parking: AttachedEntry SideDriveway

Construction

• Roofing: Shingle
• General: Brick VeneerStone2Poured Concrete

Location

• HOA Amenities: 575.0
• Originating MLS: APEX MLS (Greater Louisville Association of REALTORS®)
• County: Jefferson

Lot

• Zoning: 00000
• Fencing: FullOther

Utilities

• Utilities: Electricity ConnectedFuel:Natural
• Water: Public
• Sewer: Public Sewer

Financial

• Source: APEX MLS (Greater Louisville Association of REALTORS®)