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!
Closed
Listed by: Wood Brothers Realty • Thomas M Makowsky • Contact: 314-353-8888
Bought with: Worth Clark Realty
Price Unknown
258 Chestnut Hill Dr, O'Fallon, MO 63368
4beds
3,707sqft
Single Family Residence
Built in 2001
10,018 Square Feet Lot
$593,400 Zestimate®
$--/sqft
$3,704 Estimated rent
Home value
$593,400
$552,000 - $635,000
$3,704/mo
Zestimate® history
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List your homeWhat's special
Masonry wood-burning fireplaceFinished basementCovered patio courtyardBuilt-in entertainment centerGranite countertopsBrick exteriorMedia room
Zillow last checked:
Listing updated:
Listed by:
Thomas M Makowsky 314-353-8888,
Wood Brothers Realty
Bought with:
Tina Knox, 2012025901
Worth Clark Realty
Source: MARIS,MLS#: 25059116
Originating MLS: St. Louis Association of REALTORS
Originating MLS: St. Louis Association of REALTORSFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Primary bedroom
- Features: Floor Covering: Wood
- Level: Main
- Area: 208
- Dimensions: 16x13
Bedroom 2
- Features: Floor Covering: Carpeting
- Level: Upper
- Area: 132
- Dimensions: 12x11
Bedroom 3
- Features: Floor Covering: Carpeting
- Level: Upper
- Area: 165
- Dimensions: 15x11
Bedroom 4
- Features: Floor Covering: Carpeting
- Level: Upper
- Area: 144
- Dimensions: 12x12
Bonus room
- Features: Floor Covering: Carpeting
- Level: Basement
Breakfast room
- Features: Floor Covering: Ceramic Tile
- Level: Main
- Area: 168
- Dimensions: 14x12
Dining room
- Features: Floor Covering: Wood
- Level: Main
- Area: 169
- Dimensions: 13x13
Great room
- Features: Floor Covering: Wood
- Level: Main
- Area: 320
- Dimensions: 20x16
Kitchen
- Features: Floor Covering: Ceramic Tile
- Level: Main
- Area: 168
- Dimensions: 14x12
Kitchen
- Features: Floor Covering: Ceramic Tile
- Level: Basement
- Area: 195
- Dimensions: 15x13
Laundry
- Features: Floor Covering: Ceramic Tile
- Level: Main
- Area: 168
- Dimensions: 14x12
Media room
- Features: Floor Covering: Carpeting
- Level: Basement
- Area: 252
- Dimensions: 21x12
Office
- Features: Floor Covering: Carpeting
- Level: Basement
Heating
- Forced Air, Natural Gas, Hot Water
Cooling
- Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Stainless Steel Appliance(s), Electric Cooktop, Dishwasher, Disposal, Dryer, Built-In Freezer, Ice Maker, Microwave, Other, Built-In Electric Oven, Built-In Range, Built-In Refrigerator, Oven, Washer, Gas Water Heater, Water Purifier, Wine Refrigerator
- Laundry: Electric Dryer Hookup, Laundry Closet, Laundry Room, Main Level, Washer Hookup
Features
- Bar, Bidet, Breakfast Bar, Breakfast Room, Built-in Features, Custom Cabinetry, Double Vanity, Eat-in Kitchen, Entrance Foyer, High Speed Internet, Lever Faucets, Open Floorplan, Pantry, Separate Dining, Smart Home, Smart Thermostat, Sound System, Storage, Two Story Entrance Foyer, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Wired for Sound
- Flooring: Carpet, Ceramic Tile, Hardwood
- Windows: Blinds, Double Pane Windows, Drapes, Screens, Shutters
- Basement: Partially Finished,Full,Other,Storage Space,Sump Pump
- Number of fireplaces: 2
- Fireplace features: Free Standing, Great Room, Masonry, Outside, Raised Hearth, Wood Burning
Interior area
- Total structure area: 3,707
- Total interior livable area: 3,707 sqft
- Finished area above ground: 2,507
Property
Parking
- Total spaces: 3
- Parking features: Attached, Direct Access, Driveway, Garage, Garage Door Opener, Inside Entrance, Lighted, Workshop in Garage
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Patio & porch: Covered, Front Porch, Patio
- Exterior features: Covered Courtyard, Entry Steps/Stairs, Fire Pit, Misting System
- Fencing: Back Yard,Gate
Lot
- Size: 10,018 Square Feet
- Features: Back Yard, Close to Clubhouse, Front Yard, Level, Near Golf Course, Sprinklers In Front, Sprinklers In Rear
Details
- Additional structures: Clubhouse
- Parcel number: 4069A8339000144.0000000
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick Veneer, Vinyl Siding
- Foundation: Other
- Roof: Shingle
Condition
- Updated/Remodeled
- New construction: No
- Year built: 2001
Utilities & green energy
- Electric: Other
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Electricity Available, Natural Gas Available
Community & HOA
Community
- Features: Clubhouse, Fishing, Golf, Park, Playground, Pool, Restaurant, Sidewalks, Street Lights, Trail(s)
- Security: Carbon Monoxide Detector(s), Security System Owned, Smoke Detector(s)
- Subdivision: Timber Meadows Village
HOA
- Has HOA: Yes
- Amenities included: Association Management, Common Ground, Park, Parking, Picnic Area, Playground
- Services included: Common Area Maintenance, Snow Removal
- HOA fee: $495 annually
- HOA name: Winghaven
Location
- Region: Ofallon
Financial & listing details
- Tax assessed value: $428,036
- Annual tax amount: $5,132
- Date on market: 9/5/2025
- Cumulative days on market: 82 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Private
- Electric utility on property: Yes
Price history
| Date | Event | Price |
|---|---|---|
| 12/29/2025 | Sold | -- |
Source:  MARIS #25059116 Report a problem | ||
| 11/26/2025 | Pending sale | $589,000$159/sqft |
Source: MARIS #25059116 Report a problem | ||
| 11/13/2025 | Price change | $589,000-1%$159/sqft |
Source: MARIS #25059116 Report a problem | ||
| 9/25/2025 | Price change | $595,000-3.9%$161/sqft |
Source: MARIS #25059116 Report a problem | ||
| 9/5/2025 | Listed for sale | $619,000+118%$167/sqft |
Source: MARIS #25059116 Report a problem | ||
| 11/15/2012 | Sold | -- |
Source: MARIS #12048859 Report a problem | ||
| 9/23/2012 | Price change | $284,000-2%$77/sqft |
Source: RE/MAX Suburban #12048859 Report a problem | ||
| 9/9/2012 | Price change | $289,900-3%$78/sqft |
Source: RE/MAX Suburban #12048859 Report a problem | ||
| 8/23/2012 | Listed for sale | $299,000$81/sqft |
Source: RE/MAX Suburban #12048859 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,399 +5.2% | $81,327 +8.3% |
| 2024 | $5,133 -0.1% | $75,089 |
| 2023 | $5,137 +13.9% | $75,089 +22.2% |
| 2022 | $4,510 | $61,439 |
| 2021 | -- | $61,439 +6.9% |
| 2020 | -- | $57,468 |
| 2019 | $4,133 | $57,468 +5% |
| 2018 | $4,133 +0.6% | $54,720 |
| 2017 | $4,107 +11% | $54,720 +15.8% |
| 2016 | $3,699 +1.5% | $47,272 |
| 2015 | $3,644 +4.3% | $47,272 -2.7% |
| 2014 | $3,493 | $48,598 +0.8% |
| 2013 | -- | $48,209 -9.4% |
| 2012 | -- | $53,210 +2.4% |
| 2011 | -- | $51,960 |
| 2010 | -- | $51,960 |
| 2009 | -- | $51,960 -14.8% |
| 2008 | -- | $61,010 -78.9% |
| 2007 | -- | $289,510 |
| 2006 | -- | $289,510 |
| 2005 | -- | $289,510 +7.4% |
| 2004 | -- | $269,540 |
| 2003 | -- | $269,540 |
| 2002 | -- | -- |
| 2001 | -- | -- |
Find assessor info on the county website
Neighborhood: 63368
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Nearby schools
GreatSchools rating
- 8/10Crossroads Elementary SchoolGrades: K-5Distance: 0.5 mi
- 10/10Frontier Middle SchoolGrades: 6-8Distance: 2.2 mi
- 9/10Liberty High SchoolGrades: 9-12Distance: 2 mi
Schools provided by the listing agent
- Elementary: Crossroads Elem.
- Middle: Frontier Middle
- High: Liberty
Source: MARIS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$593,400
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Estimated market value
$593,400
- Missouri
- Saint Charles County
- O Fallon
- 63368
- 258 Chestnut Hill Dr
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