2 Winding Trails Cir, O'Fallon, MO 63366
OFF MARKET

2 Winding Trails Cir
O'Fallon, MO 63366

  • 5 Beds
  • 4 Baths
  • 1,492 sqft (on 0.25 acres)

$364,600

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $2,276/mo*
Refinance Your Home

$364,600

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $2,276/mo*
Refinance Your Home
5 Beds
4 Baths
1,492 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 2 Winding Trails Cir.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Lot Size
0.25 acres
Living Area
1,492 sqft
Price/Sqft
$244
Parking
Garage

About this House

Much bang for your buck in this home. 5 bedrooms! Lower level finished complete with kitchen, perfect for a get together or in-law quarters. Lovely sun porch leads to deck ready for the Bar B Q! His and Hers bathrooms in the lower level. Over sized soaking tub in Master Bedroom. New flooring in great room upstairs. Fireplaces both upstairs and down. Large corner lot! Minutes from shopping, restaurants, churches and schools.
2 Winding Trails Cir, O'Fallon, MO 63366 is a 5 bedroom, 4 bathroom, 1,492 sqft single-family home built in 1995. It last sold for $265,000 on Sep 9, 2021. It is currently off market. The Trulia Estimate is $364,600, with a rent estimate of $2,706/month.

Home Details for 2 Winding Trails Cir

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Breakfast Nook, Family Room, Master Bath, Pantry, Sun RoomCeiling Fan
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 2 Winding Trails Cir

DatePriceEventSource
09/09/2021--Sold
MARIS #21045195
08/06/2021$275,000ContingentMARIS #21045195
07/29/2021$275,000PendingToActiveMARIS #21045195
07/12/2021$299,000ContingentMARIS #21045195
07/02/2021$299,000Listed For SaleMARIS #21045195
01/10/2013$189,900ListingRemovedAgent Provided
10/27/2012$189,900PriceChange
Agent Provided
08/10/2012$195,000Listed For SaleAgent Provided
01/14/2011--Sold
N/A
12/09/2010$149,900PriceChange
Agent Provided
11/13/2010$159,900Listed For SaleAgent Provided
03/07/2003--Sold
N/A

Market trends in O Fallon

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$369K
$7.01KMoM
Sale-to-List Price
100.1%
0.1%MoM
Price per sq ft
$177
$1MoM
Available listings
286
60MoM
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Property Tax and Assessment

Year2025
Tax$4,067
Assessment$333,200
Home facts updated by county records

Comparable Sales for 2 Winding Trails Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
234 Autumn Mist Pl, O'Fallon, MO
0.22
Single-Family Home
-
12/29/25
3
3
1,933
172 Autumn Chase Dr, O'Fallon, MO
0.21
Single-Family Home
-
05/18/26
3
2
1,122
24 Laura Dr, Saint Peters, MO
0.20
Single-Family Home
-
09/16/25
3
1.5
1,824
6 Laura Dr, Saint Peters, MO
0.36
Single-Family Home
-
01/20/26
4
2
1,492
27 Laura Dr, Saint Peters, MO
0.15
Single-Family Home
-
01/30/26
4
2
1,092
1710 Springhill Dr, O'Fallon, MO
0.19
Single-Family Home
-
09/30/25
3
1.5
1,188
191 Autumn Chase Dr, O'Fallon, MO
0.17
Single-Family Home
-
10/03/25
3
2
1,272
212 Mill Pond Dr, O'Fallon, MO
0.37
Single-Family Home
-
06/08/26
4
3
2,595
10 Winter Hill Ct, O'Fallon, MO
0.46
Single-Family Home
-
12/04/25
3
2.5
1,400
1910 Pebble Brook Dr, O'Fallon, MO
0.33
Single-Family Home
-
12/11/25
3
2.5
2,000

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Winding Trails Cir.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about O Fallon

At least 269 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 90 % Say it's dog friendly

  • 90 % Say parking is easy

  • 83 % Say yards are well-kept

  • 82 % Say kids play outside

  • 79 % Say there are sidewalks

  • 78 % Say people would walk alone at night

  • 77 % Say there's holiday spirit

  • 72 % Say streets are well-lit

  • 67 % Say it's quiet

  • 57 % Say neighbors are friendly

  • 47 % Say there's wildlife

  • 47 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to restaurants

  • 36 % Say there are community events

  • 31 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Savannahep
    "Good parks. Feels safe. Everything you need is close by: grocery stores, gas stations, restaurants. "
    0
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  • Katie M Gough
    "My town is about 45 minutes from the city of St. Louis. It has access to all three major highways through St. Charles County. "
    0
    Flag
  • Roshan Bhattarai
    "Friendly neighbors, great community. Safe for the family. We are happy to find such a good place to live."
    0
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  • Miah Berka
    "It’s a fantastic place to raise a family. I feel safe & protected since living here. There are times I forget to lock my doors & I am not worried one bit. I feel like my area is very friendly as well!"
    0
    Flag
  • Trulia User
    "Safe neighbors , clean city, some great parks and lots of activities such as food. Shopping, schools are good"
    0
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  • Erellis81
    "My commute is down a country road into Defiance which is relatively quiet and peaceful. There’s definitely more homes popping up so more cars are around "
    0
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  • Candice Brown
    "Feels like Pleasantville living in this area all the neighbors are friendly and welcoming I love living here."
    0
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  • Melody Bridges
    "Quaint and affordable (if that is possible in this economy) and perfect for a family or single person. "
    0
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  • Lmedlin0101
    "Way too populated, really high taxes and high crime rate. Expensive utilities. I do not recommend living here. "
    1
    Flag
  • Ashley M.
    "Great schools Safe neighborhoods Resturants Larks are great and trails. It’s a great place to raise a family "
    0
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  • Brittany0628
    "This area is great bc it’s quaint but still near everything you want. Just off north main st. Fire dept is super close, Walgreens at the corner! It’s great!"
    0
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  • Ben C.
    "It’s nice with multiple dog parks around the area. There’s a lot to do with your pets and I think anyone with a dog would find plenty to do"
    0
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  • Couponshaneygirls
    "A constant barking outside dog. Other than that, it is ok. Not many sidewalks. You would have to use the middle of the streets! "
    0
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  • Jeff T.
    "It’s great here, I just love the neighborhood and the people here. Our elementary school could be better but it’s the only bad rated one in the entire school district. "
    0
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  • Shannon P.
    "We see people walking their dogs all the time. Just pick up your poop! She did parks available, multiple vets, daycares and groomers. "
    0
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  • Wehrehsvave
    "There are many friendly families in the area and respectful children. Would recommend to anyone to live here! "
    0
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  • Christopher P.
    "nice area with access to everything you could want. really close to shopping centers in Chesterfield. wentzville area is just down the road. school district is great and the teacher this far have been amazing. "
    0
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  • Kathy D. S.
    "It is such a vibrant Neighborhood! I’m so glad I moved my elderly Mother here! We feel so safe! And everyone takes pride in their homes and keeping the Neighborhood looking great!"
    1
    Flag
  • Kyra.chap
    "The O'Fallon Freedom Fest is a fun local event held once a year that is looked forward to by children and adults alike. "
    0
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  • Carole S.
    "Nothing happens as far as get together in the area I believe at one time people would get together but not any more area is changing too much low income housing"
    0
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  • Lisa D.
    "Easy access to all major highways easy commute for all locations. Love the neighborhood. Close to food and shopping. "
    0
    Flag
  • Trudence T.
    "My neighborhood is quite friendly and nice....filled with great shopping and eating places....comfortable living Beautiful surroundings. "
    0
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  • Jennifermerzlicker
    "I am a stay at home mom so I don’t commute anywhere. We are convenient to highways though and there are a ton of options for shopping and eating."
    0
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  • Trulia User
    "You see people walking their dogs all the time and there are areas to dispose of your dog’s waste. People tend to drive too fast."
    0
    Flag
  • Diana M.
    "Everything is close and I really enjoy being in proximity to everything, but the feel of not being in a big city."
    0
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  • Mxfx
    "Lots of beige plastic siding can be seen in every direction. It’s really quite comforting to know that everyone else in my neighborhood is just like me. Diversity is overrated. "
    0
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  • Meghan F.
    "I’ve lived here most of my life and love the safe community and schools. My daughters both love their school and I feel good about sending them daily "
    1
    Flag
  • Chasity J.
    "OFallon is a great city with a small town feel. i feel safe here, feel safe to go to any part of OFallon. You can live in a subdivision or you can find plenty of homes on 1 to 30 acres on these outskirts of town and only be 5 to 10 from large malls, mini malls and just about every well known stores or small local stores. During rush hour traffic can get a little backed up but it's only a 10 minute backup at most. "
    0
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  • Deneen S.
    "Great place to raise your kids the school district is great. People for the most part are friendly. Great atmosphere "
    0
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  • Slw2364
    "family's are friendly and have lots of get togethers. there is a neighborhood easter egg hunt, 4th of july social, movie nights and lots of trick or treats at Halloween. "
    0
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  • Natkor03
    "Everyone is friendly!! Dogs are always on a leash if they are being walked. If they aren't on a leash they are well trained and stay in their front yards. "
    0
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  • Amy
    "There are lots of communal events in Twin Chimneys, and in OFallon in general. It’s a large suburban town, but close enough to St. Louis that it’s easy to head in for a Cards game, etc. Great value for the $$$ out here."
    0
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  • carly s
    "tons of options when it comes to kid friendly holiday themed events and even non holiday oriented activities. shopping/dining/movies/parks and more, all less than 10 minute drive depending on what you're looking for"
    0
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  • Rashae C.
    "I enjoy this area very family friendly! very peaceful, I would walk outside any time if day or night."
    0
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  • Cindydodd
    "We have lived in Monticello West for 16 years and love it! People keep up their homes, it’s quiet, and close to everything! "
    0
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  • Tlbourn1549
    "Very neighbor friendly. Everyone looks out for one another. Long time residents along with others on our street. "
    0
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  • Copgal1953
    "Wonderful area for walking dogs. There are dog waste receptacles on just about every corner. Owners for the most part keep their dogs on a leash. "
    0
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  • Wynterwebb S.
    "All of the fairs are held walking distance away. Good people and layed back atmosphere. We are all very happy with this neighborhood"
    1
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  • Megan K.
    "Friendly people and family focused with neighborhood get-togethers and a neighborhood pool and tennis courts. "
    0
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  • Katherineb m.
    "Yes! Plenty of places to walk and many options for dogs of all sizes and abilities. Paved or unpaved and flat or hiking all avalible within a short distance. "
    0
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Explore by feature - Pet Friendly

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Homes for sale near 2 Winding Trails Cir

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Off Market Homes Near 2 Winding Trails Cir

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