265 Chestnut Hill Dr, O'Fallon, MO 63368
Property image
Property image
OFF MARKET

265 Chestnut Hill Dr
O'Fallon, MO 63368

  • 3 Beds
  • 3 Baths
  • 3,830 sqft (on 0.34 acres)

$655,600

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,968/mo*
Refinance Your Home

$655,600

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,968/mo*
Refinance Your Home
3 Beds
3 Baths
3,830 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 265 Chestnut Hill Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Remarkable 1.5 Story with a finished walk-out lower level, sensational saltwater pool & amazing landscaped yard! This one-owner showplace has been carefully updated & maintained. Two-story great room with a soaring wall of windows & a fireplace that flows into the open kitchen & breakfast room with a slider to the deck. Main floor master suite with a bay window & walk-in closet organizers & a private bath with dual sinks, corner soaking tub & recently updated seated tile shower. Office with French doors & impressive bookcases & formal dining room with updated tile floors. Exquisite details throughout, like 9' ceilings, crown molding & wainscoting. Upstairs is a loft, 2 family bedrooms & a full bath. The lower level rec room & bath have 2 doors to access the pool & gorgeous patio area. 3-car garage. Updated roof, gutters, HVAC, water heater & pool equipment. 13-mo home warranty included. Fun Winghaven community events, restaurants & shopping. Wentzville (Liberty) Schools. See it today!
265 Chestnut Hill Dr, O'Fallon, MO 63368 is a 3 bedroom, 4 bathroom, 3,830 sqft single-family home built in 2001. It last sold for $459,000 on Oct 1, 2019. It is currently off market. The Trulia Estimate is $655,600, with a rent estimate of $3,415/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 265 Chestnut Hill Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDisposal
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

Exterior Home Features
Exterior: Vinyl
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price History for 265 Chestnut Hill Dr

DatePriceEventSource
10/01/2019--Sold
MARIS #19056366
08/05/2019$480,000PendingAgent Provided
08/01/2019$480,000Listed For SaleAgent Provided
09/21/2001--Sold
N/A

Market trends in O Fallon

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$361K
$6.33KMoM
Sale-to-List Price
100.0%
Price per sq ft
$176
$1MoM
Available listings
226
33MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$7,104
Assessment$564,211
Home facts updated by county records

Comparable Sales for 265 Chestnut Hill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
136 Timber Meadows Dr, O'Fallon, MO
0.07
Single-Family Home
-
10/09/25
4
3.5
3,936
258 Chestnut Hill Dr, O'Fallon, MO
0.06
Single-Family Home
-
12/29/25
4
3.5
3,707
243 Chestnut Hill Dr, O'Fallon, MO
0.12
Single-Family Home
-
11/24/25
4
4
4,050
3515 Post Valley Dr, O'Fallon, MO
0.20
Single-Family Home
-
12/05/25
3
2
2,691
769 Cypress Knoll Dr, O'Fallon, MO
0.29
Single-Family Home
-
03/03/26
4
2.5
3,259
3507 Post Valley Dr, O'Fallon, MO
0.25
Single-Family Home
-
06/26/26
4
3
3,370
318 Copper Tree Ct, O'Fallon, MO
0.19
Single-Family Home
-
05/20/26
4
3.5
3,562
3605 Post Valley Ct, O'Fallon, MO
0.23
Single-Family Home
-
04/14/26
4
3.5
2,132
612 Thornridge Dr, O'Fallon, MO
0.39
Single-Family Home
-
11/19/25
3
2.5
3,700
164 Keystone Crossing Dr, O'Fallon, MO
0.46
Single-Family Home
-
05/05/26
3
2.5
2,397

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 265 Chestnut Hill Dr.
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 268 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say it's dog friendly

  • 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

  • 73 % 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Candice Brown
    "Feels like Pleasantville living in this area all the neighbors are friendly and welcoming I love living here."
    0
    Flag
  • Melody Bridges
    "Quaint and affordable (if that is possible in this economy) and perfect for a family or single person. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Wehrehsvave
    "There are many friendly families in the area and respectful children. Would recommend to anyone to live here! "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Deneen S.
    "Great place to raise your kids the school district is great. People for the most part are friendly. Great atmosphere "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Rashae C.
    "I enjoy this area very family friendly! very peaceful, I would walk outside any time if day or night."
    0
    Flag
  • 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
    Flag
  • Tlbourn1549
    "Very neighbor friendly. Everyone looks out for one another. Long time residents along with others on our street. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Megan K.
    "Friendly people and family focused with neighborhood get-togethers and a neighborhood pool and tennis courts. "
    0
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

49 pet-friendly rentals in O'Fallon, MO

Explore by feature - Garage

41 rentals with a garage in O'Fallon, MO

Explore by feature - Air Conditioning

50 rentals with air conditioning in O'Fallon, MO

Explore by feature - Pool

44 rentals with a pool in O'Fallon, MO

Explore by feature - Washer/dryer

43 rentals with a washer/dryer in O'Fallon, MO

Explore by feature - Outdoor Space

7 rentals with an outdoor space in O'Fallon, MO

Homes for sale near 265 Chestnut Hill Dr

Skip to last item
Skip to first item

Off Market Homes Near 265 Chestnut Hill Dr

Skip to last item
Skip to first item