Just Listed! Under contract. Backup offers welcomed! Welcome to 1002 Chesterton Pl, tucked away on a quiet cul-de-sac in the desirable Douglass Hills Estates. This beautifully maintained walkout brick ranch offers amazing curb appeal, a prime location close to shopping, dining, and more, and a flexible floor plan designed for modern living. With three bedrooms, three full bathrooms, a finished walkout basement, and over 3750 sq ft finished, this home provides both comfortable main-level living and versatile additional space below. Multiple non-conforming bedrooms (possible 4th & 5th) and/or flex rooms in the lower level offer the perfect setup for a home office, guest space, playroom, or workout area. Inside, the vaulted great room creates a welcoming atmosphere with built-in shelving and a gas fireplace. The kitchen is fully equipped with updated appliances (2015), ample cabinet space, and generous countertops. Enjoy meals in the cozy breakfast nook or host gatherings in the formal dining area. All three bedrooms are on the main floor, including a spacious primary suite with a jetted tub, separate shower, dual walk-in closets, and a private water closet. A second full bath serves the secondary bedrooms and guests, while the main-level laundry room adds everyday convenience. Downstairs, the finished walkout basement includes a third full bathroom and multiple flex rooms - ideal for whatever extra space you need. Step outside to enjoy the serene backyard: the main level deck and covered patio overlook a lush, private setting, while the lower level opens to another covered patio via French doors. The rear-entry two-car garage flows into the 1st floor laundry and adds convenience and extra parking space. Additional highlights include: 36-inch wide doorways Updated Andersen windows Roof replaced around 2010 Gutter Helmet system for low-maintenance gutters Lawn irrigation system New garage door opener Garage has separate heater system, not operated in some time and buyer should confirm operability during due diligence period Lennox HVAC system (updated AC components 2017) with annual service by Prudential Heating & Air since 1997 The HOA fee is $156.25/year, covering light landscaping and common area mowing, with an anticipated reassessment to $195/year in 2026. Trash service is included in the City of Douglass Hills tax bill. Residents can also join the Douglass Hills community pool and tennis club, located at 501 Gatehouse Ln, for an additional fee. The adjacent public park to the swim club offers walking trails, 2 sand volleyball courts, playground, gazebo, picnic areas, and open green space. More information is available in the MLS documents, on the dedicated listing website, and via the "Virtual Tour" link. Please note: The listing broker will not require a buyer brokerage agreement to be signed prior to viewing the property if shown by the listing agents.