1 Oakland Hills DR Chesterfield, MO 63017 Open Sun 12PM-2PM

UPDATED: 08/28/2026 06:46 PM ON MARKET: 1 days on market

$580,000

5 Beds3 Baths2,914 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 2,914 sqft

Price per Sqft $199

Subdivision Four Seasons Sec #1

MLS Listing ID 26051896

Style Other,Traditional

Bedrooms 5

Full Baths 3

HOA Fees $499/ann

Year Built 1963

Annual Tax Amount $4,849

Lot Size 0.342 Acres

Acres 0.3416

Lot Dimensions 103x101x101x24x18x34x83

Property Sub-Type Single Family Residence

Property Description

Welcome to 1 Oakland Hills Drive, updated 2-story home tucked into the sought-after Four Seasons community of Chesterfield. Offering 5 bedrooms, 3 full baths and just over 2,900 square feet of thoughtfully designed living space, this home perfectly blends classic charm with the updates and functionality today's buyers are looking for.

Step inside to beautiful hardwood flooring and an inviting foyer that opens to a spacious living room with a wonderful view of the Four Seasons Golf Course and subdivision pool. The main level also features a separate dining room conveniently located just off the kitchen, making entertaining a breeze. The updated kitchen offers custom cabinetry, quartz countertops, backsplash, under cabinet lighting, stainless steel appliances and breakfast bar seating, while the adjoining eat-in area flows seamlessly into the comfortable family room. The family room features an updated fireplace and an open layout that creates an inviting space for everyday living and gathering.

A generous bonus room adds even more versatility and can easily accommodate a playroom, home office, hobby space or guest area, with convenient access to the backyard and deck. Upstairs, you'll find a spacious primary suite with private bath, along with four additional bedrooms and another full bath, providing plenty of room for family and guests.

The finished lower level offers additional recreation space currently being used as a play area and home gym. Outside, enjoy the expansive fenced backyard, spacious deck and beautiful golf-course views—an ideal setting for relaxing, entertaining or simply enjoying the peaceful surroundings.

Additional highlights include a 3-car attached garage, full basement, community pool and clubhouse (extra $80/ year for membership), all in an incredible Chesterfield location within the Parkway School District. Recent interior updates include kitchen, fresh paint throughout, working fireplace-gas, new HVAC (both units), new water heater, switches & outlets, sliding door for deck entry, all completed between 2025 & 2026. Exterior updates include a new roof, siding, gutters and deck, all completed in 2022 as well as low maintenance landscaping in 2025. With its generous living spaces, flexible floor plan and fantastic location, check this gem out today!