Single Family for Sale: 258 Chestnut Hill Drive, O'Fallon, MO 63368

4 beds
3 full, 1 half baths
2,507 sqft
$589,000
$589,000
258 Chestnut Hill Drive, O'Fallon, MO 63368
4 beds
3 full, 1 half baths
2,507 sqft
$589,000
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Price:
$589,000
$6,000 - 11/13/2025

Type Single Family
Style 2 Story
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
County St. Charles
School District Wentzville R-IV
Subdivision Timber Meadows Village

MLS 25059116
Status Pending
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!

Virtual Tours for 258 Chestnut Hill Drive O'Fallon, MO

Room Features

Basement Description Other, Interior Entry, Storage Space, Sump Pump, Bathroom, 8 ft + Pour, Partially Finished, Full

Lot & Building Features

Appliances Built-In Range, Built-In Freezer, Water Purifier, Wine Refrigerator, Built-In Refrigerator, Wall Oven, Other, Built-In Electric Oven, Ice Maker, Electric Cooktop, Washer, Dryer, Gas Water Heater, Stainless Steel Appliance(s), Disposal, Microwave, Dishwasher
Architecture Traditional
Assoc Fee $495
Assoc Fee Paid Annually
Construction Brick Veneer, Vinyl Siding
Cooling Ceiling Fan(s), Electric, Central Air
Heating Hot Water, Natural Gas, Forced Air
Interior Decor Bidet, Smart Home, Wired for Sound, Sound System, Smart Thermostat, Two Story Entrance Foyer, Wet Bar, Lever Faucets, Bar, Built-in Features, High Speed Internet, Storage, Vaulted Ceiling(s), Breakfast Room, Double Vanity, Breakfast Bar, Custom Cabinetry, Entrance Foyer, Separate Dining, Pantry, Eat-in Kitchen, Open Floorplan, Walk-In Closet(s)
Parking Description Direct Access, Lighted, Inside Entrance, Workshop in Garage, Driveway, Garage Door Opener, Attached, Garage
Sewer Public Sewer
Tax Year 2024
Taxes Paid $5,132
Water Public
Windows And Doors Drapes, Shutters, Screens, Blinds, Double Pane Windows
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%
09/05/2025 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.

Comparable Properties Sold Near By

Low
$425,000
$172 / sqft
Average
$547,189
$218 / sqft
High
$653,264
$264 / sqft

Address City Zip Beds Baths Price Sq. Ft. $/SQFT Sold Date
This Listing O'Fallon 63368 4 4.0 $589,000 2,507 $235 N/A
402 Smithton Drive O'Fallon 63368 3 3.0 $653,264 2,475 $264 12/19/2024
725 Hawk Run Drive O'Fallon 63368 5 4.0 $515,000 2,582 $199 12/20/2024
229 Fairway Green Drive O'Fallon 63368 4 3.0 $554,900 2,545 $218 02/03/2025
147 Cardow Drive O'Fallon 63368 3 3.0 $627,853 2,536 $248 02/04/2025
119 Timber Meadows Drive O'Fallon 63368 5 4.0 $625,000 2,342 $267 04/01/2025
605 Thornridge Drive O'Fallon 63368 4 4.0 $425,000 2,470 $172 06/05/2025
206 Centennial Drive O'Fallon 63368 4 4.0 $575,000 2,429 $237 04/28/2025
713 Alban Aly O'Fallon 63368 3 3.0 $500,000 2,435 $205 09/04/2025
404 Roddens Way O'Fallon 63368 4 3.0 $541,821 2,468 $220 05/14/2025
375 Falcon Hill Drive O'Fallon 63368 4 4.0 $580,000 2,640 $220 06/11/2025
2728 Post Meadows Drive O'Fallon 63368 4 4.0 $550,000 2,373 $232 06/12/2025
514 Old Dominion Street O'Fallon 63368 4 3.0 $430,000 2,624 $164 07/01/2025
223 Glasgow Green Drive O'Fallon 63368 3 3.0 $575,000 2,650 $217 09/15/2025
442 Smithton Boulevard O'Fallon 63368 4 3.0 $580,000 2,508 $231 08/11/2025
612 Thornridge Drive O'Fallon 63368 3 3.0 $475,000 2,630 $181 11/19/2025

Map of 258 Chestnut Hill Drive, O'Fallon, MO

Location Map Street View
Photo of St. Louis
Direct: 314-353-0336
Office
3537 S Kingshighway Blvd
Saint Louis, MO 63139
314-353-0336
Listed by Wood Brothers Realty, Thomas Makowsky
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258 Chestnut Hill Drive (MLS #25059116) is a 2 story single family home located in O'Fallon, MO. This single family home is 2,507 sqft and on a lot of 10,019 sqft (or 0.23 acres) with 4 bedrooms and 4 baths. This property was listed on 09/05/2025 and has been priced for sale at $589,000.

The 5 bedroom single family home at 119 Timber Meadows Drive in O'Fallon is nearby and sold for $625,000 on 04/01/2025. Another nearby 4 bedroom single family home, 2728 Post Meadows Drive in O'Fallon sold for $550,000 on 06/12/2025.

Nearby zip codes are 63304, 63366, 63367, 63376 and 63385. This property neighbors other cities such as Dardenne Prairie, Lake St Louis, St Charles, St Peters and Wentzville.

Maris

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

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