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258 Chestnut Hill Drive
O'Fallon MO 63368 US

$595,000

Active Listing ID 25059116
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4 bed
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4.00 Bath (3 Full , 1 Half)
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Lot: 0.23 Acres
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Single Family Residence

$595,000

Active Listing ID 25059116
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258 Chestnut Hill Drive 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!

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Property Features

  • Facts
  • Lot Size: 0.23 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • 1/2 Bathrooms: 1
  • Cooling System: Ceiling Fan(s), Central Air, Electric
  • Exterior Finish: Level, Fencing, Covered Courtyard, Entry Steps/Stairs, Fire Pit, Misting System
  • Floor Covering: Carpet, Hardwood, Tile, Tile - Ceramic
  • Roof Type: Shingle
  • Heating Fuels: Fireplace(s), Forced Air, Hot Water (Heating), Natural Gas
  • Additional Features
  • Fireplace

School Information

  • School
  • Crossroads Elem.(Elementary)
  • Frontier Middle(MiddleSchool)
  • Timberland High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 595000
  • unparsedaddress: 258 Chestnut Hill Drive
  • postalcity: O'Fallon
  • stateorprovince: MO
  • country: US
  • postalcode: 63368
  • bathroomsfull: 3
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.23
  • lotsizeunits: Acres
  • lotsizearea: 0.23
  • livingarea: 3707
  • livingareaunits: Square Feet
  • latitude: 38.757802
  • longitude: -90.750653
  • listagentfullname: Thomas Makowsky
  • listagentemail: tmakowsky@woodbrothersrealty.com
  • listagentkey: 3yd-MARISMO-TMAKOWSK
  • listagentmlsid: TMAKOWSK
  • listagentpreferredphone: 3148251080
  • listagentofficephone: 3143538888
  • listofficekey: 3yd-MARISMO-WBRS01
  • listagentstatelicense: 2023014422
  • listofficemlsid: WBRS01
  • disclaimer: Copyright © 2025 MARIS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MARISMO
  • yearbuilt: 2001
  • listagenturl: http://www.wbrstl.com
  • countyorparish: St. Charles
  • parcelnumber: 4-069A-8339-00-0144.0000000
  • elementaryschool: Crossroads Elem.
  • highschool: Liberty
  • elementaryschooldistrict: Wentzville R-IV
  • middleorjuniorschooldistrict: Wentzville R-IV
  • highschooldistrict: Wentzville R-IV
  • appliances: Cooktop, Cooktop - Electric, Dishwasher, Dryer, Freezer, Garbage Disposer, Ice Maker, Microwave, Range, Refrigerator, Refrigerator - Built-in, Refrigerator - Wine Storage, Washer, Water - Purifier
  • cooling: Ceiling Fan(s), Central Air, Electric
  • constructionmaterials: Brick, Brick Veneer, Vinyl Siding
  • flooring: Carpet, Hardwood, Tile, Tile - Ceramic
  • heating: Fireplace(s), Forced Air, Hot Water (Heating), Natural Gas
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Garage - Attached, Workshop
  • roof: Shingle
  • waterfrontyn: False
  • interiorfeatures: 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
  • exteriorfeatures: Level, Fencing, Covered Courtyard, Entry Steps/Stairs, Fire Pit, Misting System
  • architecturalstyle: New Traditional
  • rooms: Basement, Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bonus Room, Dining Room, Great Room, Kitchen, Laundry, Media Room, Office
  • securityfeatures: Security System, Security System Owned, Smoke Detector(s)
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -90.750656, 38.7578
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Wood Brothers Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[{"ExpenseCategory":"Home Owner Assessments Fee", "ExpenseFrequency":"Annually", "ExpenseValue":495}], "GeocodeOptions":null, "LeadRoutingEmail":"tmakowsky@woodbrothersrealty.com", "ListBrokerageCity":"Saint Louis", "ListBrokerageCountry":"US", "ListBrokerageEmail":"bwood@wbrstl.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/MARISMO/10e2b7a11ab211e1a59700219b994c72/20121018192633070.png", "ListBrokerageName":"Wood Brothers Realty", "ListBrokeragePhone":"(314) 353-8888", "ListBrokeragePostalCode":"63109", "ListBrokerageStateOrProvince":"MO", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"6500 Chippewa St", "ListBrokerageWebsiteUrl":"http://www.wbrstl.com", "ListOfficeAddress1":"6500 Chippewa St Fl 1", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"SLOWOODK", "ListOfficeCity":"Saint Louis", "ListOfficeCountry":"US", "ListOfficeEmail":"bwood@wbrstl.com", "ListOfficePostalCode":"63109", "ListOfficeStateOrProvince":"MO", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence, Ranch/2 Story, Traditional - O'Fallon, MO", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/258-Chestnut-Hill-Dr_O-Fallon_MO_63368_M84900-01218?f=listhub&s=MARISMO&m=25059116&c=rexren", "MLSModificationTimestamp":"2025-10-06T00:31:49Z", "Neighborhoods":[{"Description":null, "Name":"416 - Wentzville-Timberland"}], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":13, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":5132, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/7/2025 8:08:31 PM GMT
Source Updated Date: 12/6/2025 12:40:37 PM GMT

Courtesy of: Thomas Makowsky, Wood Brothers Realty, tmakowsky@woodbrothersrealty.com

Copyright © 2025 MARIS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.