Single Family for Sale: 258 Chestnut Hill Drive, O'Fallon, MO 63368 SOLD
4 beds
3 full, 1 half baths
2,507 sqft
$589,000
$589,000
258 Chestnut Hill Drive,
O'Fallon, MO 63368 SOLD
4 beds
3 full, 1 half baths
2,507 sqft
$589,000
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Selling Price: $589,000
Original List Price: $619,000
Sold at 95.2% of list price
Sold Date: 12/29/2025
Type Single Family
Style 2 Story
Architecture Traditional
Beds 4
Baths 3 full, 1 half baths
Total Living Area 3,707 sqft
Square Footage 2,507 sqft
Garage Spaces 3
Lot Size 0.23 acres
Year Built 2001
Assoc Fee $495
Assoc Fee Paid Annually
Taxes Paid $5,132
City O'Fallon
Area 416 - Wentzville-Timberland
County St. Charles
School District Wentzville R-IV
Subdivision Timber Meadows Village
MLS 25059116
Status Closed
DOM 82 days
Stunning 3,707 sq. ft. 2-story home with finished basement in desirable Winghaven Country Club community! Built in 2001 with a brick exterior, this home blends elegance with modern updates.
The main floor showcases a remodeled gourmet kitchen with Wolf cooktop, Sub-Zero freezer, granite countertops, Bosch oven, and Asko dishwasher seamlessly flowing into the open floor plan with breakfast room, vaulted great room with masonry wood-burning fireplace and hardwood floors, and a separate dining room. The highlight is the luxurious master suite, featuring walk-in closets and a completely remodeled spa bath with a curbless walk-in shower and modern finishes. Also on the main level: a separate laundry room and half bath.
Upstairs you’ll find three bedrooms and a full bath, while the finished basement is an entertainer’s dream with full kitchen, media room with built-in entertainment center & surround sound, office, bonus room, and another full bath.
Enjoy the outdoors on the covered patio courtyard with a masonry wood-burning fireplace. Additional highlights include a 3-car garage, newer roof (~8 years old), and prime location near the golf course. Winghaven Country Club membership opportunity available, offering golf, pool, dining, and a full calendar of social events just steps away!
Room Features
Basement Description Other, Interior Entry, 8 ft + Pour, Storage Space, Sump Pump, Bathroom, Partially Finished, Full
Lot & Building Features
Appliances Built-In Freezer, Built-In Range, Water Purifier, Wine Refrigerator, Built-In Electric Oven, Other, Ice Maker, Built-In Refrigerator, Wall Oven, Electric Cooktop, Gas Water Heater, Washer, Dryer, Stainless Steel Appliance(s), Disposal, Microwave, Dishwasher
Assoc Fee $495
Assoc Fee Paid Annually
Construction Brick Veneer, Vinyl Siding
Cooling Central Air, Ceiling Fan(s), Electric
Heating Hot Water, Natural Gas, Forced Air
Interior Decor Bidet, Smart Home, Wired for Sound, Sound System, Smart Thermostat, Lever Faucets, Built-in Features, Storage, Bar, High Speed Internet, Wet Bar, Vaulted Ceiling(s), Breakfast Room, Double Vanity, Breakfast Bar, Entrance Foyer, Eat-in Kitchen, Custom Cabinetry, Pantry, Separate Dining, Two Story Entrance Foyer, Walk-In Closet(s), Open Floorplan
Parking Description Direct Access, Inside Entrance, Lighted, Driveway, Workshop in Garage, Attached, Garage, Garage Door Opener
Sewer Public Sewer
Tax Year 2024
Taxes Paid $5,132
Water Public
Windows And Doors Drapes, Screens, Double Pane Windows, Blinds, Shutters
Fireplaces 2
Community and Schools
Elementary School Crossroads Elem.
Junior High School Frontier Middle
Senior High School Liberty
Price History of 258 Chestnut Hill Drive, O'Fallon, MO
| Date | Name | Price | Difference |
|---|---|---|---|
| 11/13/2025 | Price Adjustment | $589,000 | 1.01% |
| 09/25/2025 | Price Adjustment | $595,000 | 3.88% |
| Coming Soon | Listing Price | $619,000 | N/A |
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed. |
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![]() Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listing information courtesy of: Wood Brothers Realty Listings displaying the MARIS logo are courtesy of the participants of Mid America Regional Information Systems Internet Data Exchange |


