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Luxury Homes in Chesterfield, MO
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Start here

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  • The buying timeline

Afford it

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16 listings
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3 bedsNew constructionWith a pool

Luxury Homes in Chesterfield, MO

Luxury Homes in Chesterfield, MO

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16 Listings
Map

Luxury Homes in Chesterfield, MO

16 Listings

Your local team in Chesterfield

TO

Thomas O'Leary

Realty.com

Lic. #2020001504

Call Thomas
LM

Lisa McLaughlin

Delmar Mortgage

NMLS #283815

Lisa McLaughlinCall Lisa
  1. 16529 Waterfront Avenue — photo66Active

    $2,275,000

    2 bd · 4 ba · 3,330 sqft

    16529 Waterfront Avenue, Chesterfield, MO

    Melinda McCarthy · Janet McAfee Inc.

  2. 360 Willow Weald Path — photo69Active

    $1,349,000

    4 bd · 4 ba · 5,969 sqft

    360 Willow Weald Path, Chesterfield, MO

    Mark & Neil Gellman · EXP Realty, LLC

  3. 195 Kendall Bluff Court — photo28Active

    $1,075,000

    3 bd · 3 ba · 3,784 sqft

    195 Kendall Bluff Court, Chesterfield, MO

    Rex Schwerdt · Dielmann Sotheby's International Realty

  4. 16334 Baxter Road — photoPrice Reduced48Active

    $1,190,000

    4 bd · 4 ba · 3,889 sqft

    16334 Baxter Road, Chesterfield, MO

    Kristi Lindgren · Compass Realty Group

  5. 308 Willow Weald Path — photo97Active

    $1,400,000

    6 bd · 5 ba · 5,076 sqft

    308 Willow Weald Path, Chesterfield, MO

    Peter Lu · EXP Realty, LLC

  6. 1278 Harvester Drive — photo39Active

    $1,179,000

    5 bd · 5 ba · 4,527 sqft

    1278 Harvester Drive, Chesterfield, MO

    Lisa Accurso · Coldwell Banker Realty - Gundaker

  7. 2154 White Lane Drive — photo41Active

    $1,250,000

    4 bd · 6 ba · 5,099 sqft

    2154 White Lane Drive, Chesterfield, MO

    Kelly Messmer · RE/MAX Results

  8. 16936 Lake Meadow — photo32Active

    $2,000,000

    5 bd · 6 ba · 6,760 sqft

    16936 Lake Meadow, Chesterfield, MO

    Justin Michael · The Wells Michael Collective

  9. 753 Silver Buck Lane — photo67Active

    $2,200,000

    4 bd · 4 ba · 5,535 sqft

    753 Silver Buck Lane, Chesterfield, MO

    Tom Basler · Keller Williams Chesterfield

  10. 16955 Pine Summit Drive — photoPrice Reduced55Active

    $1,479,000

    5 bd · 5 ba · 4,348 sqft

    16955 Pine Summit Drive, Chesterfield, MO

    Jeff Lottmann · Compass Realty Group

  11. 220 Woodcliffe Place Drive — photoPrice Reduced43Active

    $1,250,000

    6 bd · 5 ba · 5,562 sqft

    220 Woodcliffe Place Drive, Chesterfield, MO

    Marie Kutryb · The Dyer/Kutryb Group

  12. 655 Old Riverwoods Lane — photoPrice Reduced58Active

    $1,250,000

    6 bd · 5 ba · 5,411 sqft

    655 Old Riverwoods Lane, Chesterfield, MO

    Allen Brake · Allen Brake Real Estate

  13. 2325 Sterling Pointe Drive — photo48Active

    $1,450,000

    5 bd · 6 ba · 6,572 sqft

    2325 Sterling Pointe Drive, Chesterfield, MO

    DJ Gudipati · Platinum Realty of St. Louis

  14. 17 West Drive — photoPrice Reduced73Active

    $2,499,000

    4 bd · 6 ba · 5,823 sqft

    17 West Drive, Chesterfield, MO

    Catherine Shaw-Connely · Tom Shaw, REALTORS

  15. 1004 Weidman Road — photoPrice Reduced17Active

    $2,900,000

    4 bd · 2 ba · 1,707 sqft

    1004 Weidman Road, Chesterfield, MO

    Thomas Wood · GFW Properties, LLC

  16. 805 Silver Buck Lane — photo50Active

    $1,640,000

    3 bd · 4 ba · 4,534 sqft

    805 Silver Buck Lane, Chesterfield, MO

    Tom Basler · Keller Williams Chesterfield

Explore Chesterfield homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

MARIS MLS
Based on information submitted to the MLS GRID as of 2026-09-02 16:49:21 UTC. 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.
  • By feature

    • New construction
    • With a pool

    Your local team in Chesterfield

    TO

    Thomas O'Leary

    Realty.com

    Lic. #2020001504

    Call Thomas
    LM

    Lisa McLaughlin

    Delmar Mortgage

    NMLS #283815

    Lisa McLaughlinCall Lisa

    Chesterfield, MO community profile

    Population
    49,598
    Median income
    $132,733
    Housing units
    21,191
    People per sq. mi.
    763
    Area
    65 sq. mi.

    Source: HJN community data

    Chesterfield housing market

    August 2026 · This period is still settling

    Chesterfield 12-month median sale price trend

    Homes that sold · County records, as of Aug 11, 2026

    Median sale price
    $470,800$378,750–$579,487 typical range
    Price per sq. ft.
    $203
    Sales
    17
    Paid in cash
    5.9%

    Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

    Median list price
    $557,500
    Homes for sale
    108
    Median days on market
    5 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -20.5%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    2,736 sq. ft.