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Street View
$569,900
Monthly Est:$2,837
5 Beds
- 3 Baths
3 full baths
2,914sqft
1 Oakland Hills Dr, Chesterfield, MO 63017
$569,900
$2,837/moEst:
Get Pre-Approved
Single Family Residence
Built in 1963
$41.58/mo HOA
14,880.1 sqft lot
$196/sq.ft
Description
Welcome to 1 Oakland Hills Drive, updated 2-story home tucked into the sought-after Four Seasons community of Chesterfield. Offering 5 bedrooms, 3 full baths and just over 2,900 square feet of thoughtfully designed living space, this home perfectly blends classic charm with the updates and functionality today’s buyers are looking for.
Step inside to beautiful hardwood flooring and an inviting foyer that opens to a spacious living room with a wonderful view of the Four Seasons Golf Course and subdivision pool. The main level also features a separate dining room conveniently located just off the kitchen, making entertaining a breeze. The updated kitchen offers custom cabinetry, quartz countertops, backsplash, under cabinet lighting, stainless steel appliances and breakfast bar seating, while the adjoining eat-in area flows seamlessly into the comfortable family room. The family room features an updated fireplace and an open layout that creates an inviting space for everyday living and gathering.
A generous bonus room adds even more versatility and can easily accommodate a playroom, home office, hobby space or guest area, with convenient access to the backyard and deck. Upstairs, you’ll find a spacious primary suite with private bath, along with four additional bedrooms and another full bath, providing plenty of room for family and guests.
The finished lower level offers additional recreation space currently being used as a play area and home gym. Outside, enjoy the expansive fenced backyard, spacious deck and beautiful golf-course views—an ideal setting for relaxing, entertaining or simply enjoying the peaceful surroundings.
Additional highlights include a 3-car attached garage, full basement, community pool and clubhouse (extra $80/ year for membership), all in an incredible Chesterfield location within the Parkway School District. Recent interior updates include kitchen, fresh paint throughout, working fireplace-gas, new HVAC (both units), new water heater, switches & outlets, sliding door for deck entry, all completed between 2025 & 2026. Exterior updates include a new roof, siding, gutters and deck, all completed in 2022 as well as low maintenance landscaping in 2025. With its generous living spaces, flexible floor plan and fantastic location, check this gem out today!
- Houzeo last checked: 1 hour ago
- Listing updated: September 10, 2026 at 5:03 pm
- Listing Provided by: Amy Copeland (314) 304-2454 | Blondin Group, Inc (636) 398-5770
- Source: MARIS MLS-MO | MLS#: MIS26051896

Property Details
Status
Active Under Contract
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1963
HOA Fees
$41.58/mo
Finished Area
2,914 sqft
Lot Size
14,880.1 sqft lot
Basement Area
- sqft
MLS Name
MARIS MLS
MLS Number
MIS26051896
MLS Status
Active Under Contract
Days on Market
47
Cumulative Days on Market
13

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Location
HOA Management
Four Seasons
HOA Fees
$499/ Annually
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Insurance
Snow Removal
Common Area
Management
Common Area Maintenance
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 3
Living Room
Level: Main
Area: 247.00 Square Feet
Dimensions: 19x13
Family Room
Level: Main
Area: 273.00 Square Feet
Dimensions: 21x13
Recreation Room
Level: Main
Area: 391.00 Square Feet
Dimensions: 17x23
Breakfast Room
Level: Main
Area: 110.00 Square Feet
Dimensions: 10x11
Kitchen
Level: Main
Area: 156.00 Square Feet
Dimensions: 12x13
Dining Room
Level: Main
Area: 156.00 Square Feet
Dimensions: 12x13
Primary Bedroom
Level: Upper
Area: 273.00 Square Feet
Dimensions: 21x13
Bedroom
Level: Upper
Area: 143.00 Square Feet
Dimensions: 11x13
Bedroom 2
Level: Upper
Area: 108.00 Square Feet
Dimensions: 12x9
Bedroom 3
Level: Upper
Area: 90.00 Square Feet
Dimensions: 10x9
Bedroom 4
Level: Upper
Area: 156.00 Square Feet
Dimensions: 12x13
Basement
Level: Lower
Area: 377.00 Square Feet
Dimensions: 29x13
Basement
Level: Lower
Area: 156.00 Square Feet
Dimensions: 12x13
Interior
Window Features
Blinds, Window Coverings, Window Treatments, Wood Frames
Exterior Features
Private Yard
Sewer
Public Sewer
Heating
Forced Air, Natural Gas
Flooring
Carpet, Ceramic Tile
Interior Features
Breakfast Room, Ceiling Fan(s), Eat In Kitchen, Entrance Foyer, Open Floorplan, Separate Dining, Stone Counters
Appliances
Dishwasher, Disposal, Microwave, Gas Oven, Gas Range, Washer/dryer
Cooling
Ceiling Fan(s), Central Air, Electric
Construction
Year Built
Year Built: 1963
Home type
Single Family Residence
Property Condition
Updated/remodeled
Construction Materials
Brick, Vinyl Siding
Foundation Details
Concrete Perimeter
Architectural Style
Other, Traditional
Roof
Architectural Shingle
Utilities & Energy
Association Amenities
Common Ground
Utilities
Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Security Features
Carbon Monoxide Detector(s), Smoke Detector(s)
Fireplace Features
Family Room, Gas
Parking Features
Attached, Concrete, Driveway, Off Street, On Street
Basement
8 Ft + Pour, Full, Storage Space
Laundry Features
In Basement, Lower Level
Electric
220 Volts
Water Source
Public
Pool Features
Community, In Ground
Other Features
Subdivision Name
Four Seasons Sec #1
Patio And Porch Features
Covered, Deck, Front Porch
Community Features
Clubhouse, Pool, Sidewalks, Street Lights
Disclosures
Flood Plain No, Seller Property Disclosure
Lot Features
Back Yard, Corner Lot, Few Trees, Front Yard, Level, Near Golf Course
Price History
| Date | Event | Price |
|---|---|---|
09/10/2026 Source: | Contingent (Active Under Contract) | $569,900 $196/sqft |
09/08/2026 Source: | Price Decreased | $569,900 -1.74% $196/sqft |
08/28/2026 Source: | Listed for Sale | $580,000 $199/sqft |
08/21/2026 Source: | Coming Soon | $580,000 +6.42% $199/sqft |
05/09/2025 Source: | Sold | $545,000 +2.44% $187/sqft |
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Based on information from Mid America Regional Information Systems, Inc. through Oct 08, 2026, 09:01AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is
subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website.
Properties displayed may be listed or sold by various participants in the MLS. Property data presented reflect information otherwise available from public records. The REALTOR® providing this information may not have represented the buyer or seller
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