Active Under Contract
Price CutPrice Drop: $10.1K (09/10)
Single family home for sale at 1 Oakland Hills Dr, Chesterfield, MO 63017 | MLS# MIS26051896 | Listing updated on 2026-09-10
Photo 1 of Single family home for sale at 1 Oakland Hills Dr, Chesterfield, MO 63017 | MLS# MIS26051896 | Listing updated on 2026-09-10
Photo 2 of Single family home for sale at 1 Oakland Hills Dr, Chesterfield, MO 63017 | MLS# MIS26051896 | Listing updated on 2026-09-10
Photo 3 of Single family home for sale at 1 Oakland Hills Dr, Chesterfield, MO 63017 | MLS# MIS26051896 | Listing updated on 2026-09-10
Photo 4 of Single family home for sale at 1 Oakland Hills Dr, Chesterfield, MO 63017 | MLS# MIS26051896 | Listing updated on 2026-09-10
82+
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Street View

$569,900

Monthly Est:$2,837

  • Beds Icon5 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,914sqft

1 Oakland Hills Dr, Chesterfield, MO 63017

$2,837/moEst:

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  • 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 cabin
etry, 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 MARIS MLS-MO

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    St. Louis County

  • City

    Chesterfield

  • 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 Insurance

Snow Removal Snow Removal

Common Area Common Area

Management Management

Common Area Maintenance 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

DateEventPrice

09/10/2026

Source: mls_logoMARIS MLS-MO #MIS26051896

Contingent (Active Under Contract)

$569,900

$196/sqft

09/08/2026

Source: mls_logoMARIS MLS-MO #MIS26051896

Price Decreased

$569,900 -1.74%

$196/sqft

08/28/2026

Source: mls_logoMARIS MLS-MO #MIS26051896

Listed for Sale

$580,000

$199/sqft

08/21/2026

Source: mls_logoMARIS MLS-MO #MIS26051896

Coming Soon

$580,000 +6.42%

$199/sqft

05/09/2025

Source: mls_logoMARIS MLS-MO #MIS25007042

Sold

$545,000 +2.44%

$187/sqft

Show more

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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 in some or all of the transactions.
IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. © 2026 Mid America Regional Information Systems, Inc. All Rights Reserved.

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