Real Estate Investment Properties for Sale in Chesterfield, MO

Looking for investment property in Chesterfield, MO with high ROI ?

Explore a variety of short-term homes & houses in Chesterfield, MO. Invest wisely with VRBO & Chesterfield, MO Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chesterfield, MO

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
596 Eagle Manor Lane Chesterfield, MO 100-Day Home Warranty coverage available at closing. Seller may consider buyer concession...	4 beds \| 5 baths \| 5,393 sq.ft.	$700,000	Airbnb cash on cash: 0% Traditional cash on cash: 4.86% Airbnb Rental Income: $2023 Traditional Rental Income: $4673 Airbnb ROI: 0% Traditional ROI: 4.86%
13555 Coliseum Drive #G Chesterfield, MO Charming and move-in ready, this well-maintained home offers 2 spacious bedrooms & 2 full ...	2 beds \| 2 baths \| 1,020 sq.ft.	$138,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.67% Airbnb Rental Income: $1683 Traditional Rental Income: $1430 Airbnb ROI: 3.04% Traditional ROI: 4.67%
1315 Wildhorse Meadows Drive Chesterfield, MO Elegant estate situated on one acre! From a grand 2-story entrance you'll notice supreme f...	5 beds \| 6 baths \| 7,679 sq.ft.	$1,695,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.95% Airbnb Rental Income: $2408 Traditional Rental Income: $6288 Airbnb ROI: -0.89% Traditional ROI: 1.95%
1621 Walpole Drive #B Chesterfield, MO This unique corner Parkway Central condo/townhome in popular Windsor Manor is perfect for ...	4 beds \| 3 baths \| 1,561 sq.ft.	$335,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 8.28% Airbnb Rental Income: $2023 Traditional Rental Income: $3936 Airbnb ROI: 0.53% Traditional ROI: 8.28%
14361 Stablestone Court Chesterfield, MO Welcome to this charming and spacious Chesterfield home offering comfort, convenience, and...	4 beds \| 3 baths \| 3,144 sq.ft.	$565,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.53% Airbnb Rental Income: $2023 Traditional Rental Income: $3037 Airbnb ROI: 0.61% Traditional ROI: 3.53%
2323 Manor Grove Drive #4 Chesterfield, MO Updated ground-level Chesterfield condominium located in Manors of Broadmoor. SPOTLESS! F...	3 beds \| 2 baths \| 1,490 sq.ft.	$240,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 0.98% Airbnb Rental Income: $1454 Traditional Rental Income: $1747 Airbnb ROI: -2.22% Traditional ROI: 0.98%
1556 Wildhorse Parkway Drive Chesterfield, MO This exquisite newly built just finished on September 14th, 2025, 1.5 story home 0.72 Acre...	5 beds \| 5 baths \| 4,260 sq.ft.	$1,299,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.61% Airbnb Rental Income: $2408 Traditional Rental Income: $4691 Airbnb ROI: 0.23% Traditional ROI: 2.61%
16078 Meadow Oak Drive Chesterfield, MO Welcome to this inviting 1.5-story home in Chesterfield in Rockwood Schools! Situated in C...	4 beds \| 3 baths \| 2,668 sq.ft.	$530,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.27% Airbnb Rental Income: $2023 Traditional Rental Income: $2777 Airbnb ROI: 0.69% Traditional ROI: 3.27%
16446 Dapple Gray Court Chesterfield, MO Tucked away on 3 private, wooded acres, this beautifully updated ranch home offers the per...	4 beds \| 5 baths \| 5,368 sq.ft.	$799,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 4.05% Airbnb Rental Income: $2023 Traditional Rental Income: $4795 Airbnb ROI: -0.38% Traditional ROI: 4.05%
14009 Ladue Road Chesterfield, MO Welcome to 14009 Ladue Rd, a stunning full-brick colonial on a premier half-acre lot in Ch...	4 beds \| 3 baths \| 3,856 sq.ft.	$675,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.56% Airbnb Rental Income: $2023 Traditional Rental Income: $2896 Airbnb ROI: 0.34% Traditional ROI: 2.56%
1237 Cedar Creek Rd Chesterfield, MO Buy this home if YOU Are Not Satisfied with your purchase in 12 Months I'LL Buy It back or...	4 beds \| 3 baths \| 2,506 sq.ft.	$499,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.55% Airbnb Rental Income: $2023 Traditional Rental Income: $3092 Airbnb ROI: 1.13% Traditional ROI: 4.55%
9 Picardy Hill Drive Chesterfield, MO Welcome to this Beautifully updated 5BR/4.5BA Villa offering nearly 4,000 sq. ft. of elega...	5 beds \| 5 baths \| 3,890 sq.ft.	$899,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.17% Airbnb Rental Income: $2408 Traditional Rental Income: $3903 Airbnb ROI: -0.32% Traditional ROI: 2.17%
831 Stone Meadow Drive Chesterfield, MO Location, location, Chesterfield's Meadows at Stonehill is nested in a superb location be...	2 beds \| 3 baths \| 2,712 sq.ft.	$569,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.69% Airbnb Rental Income: $1683 Traditional Rental Income: $2063 Airbnb ROI: -0.9% Traditional ROI: 0.69%
962 Silver Buck Lane Chesterfield, MO Welcome to this beautiful 1.5-story home situated on a large, level fenced lot that backs ...	4 beds \| 4 baths \| 3,905 sq.ft.	$1,200,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.8% Airbnb Rental Income: $2023 Traditional Rental Income: $3338 Airbnb ROI: -0.85% Traditional ROI: 0.8%
753 Silver Buck Lane Chesterfield, MO New Construction (HOME TO BE BUILT)! Built by one of St. Louis' premier hands on builders ...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,640,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.06% Airbnb Rental Income: $1454 Traditional Rental Income: $2987 Airbnb ROI: -1.35% Traditional ROI: -0.06%
744 Silver Buck Lane Chesterfield, MO New Construction!!! Built by one of St. Louis' premier hands on builders Claymont Develop...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,640,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.06% Airbnb Rental Income: $1454 Traditional Rental Income: $2987 Airbnb ROI: -1.35% Traditional ROI: -0.06%
782 Schaeffer's Grove Court Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! Built by one of St. Louis' premier hands...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,640,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.06% Airbnb Rental Income: $1454 Traditional Rental Income: $2987 Airbnb ROI: -1.35% Traditional ROI: -0.06%
16757 Benton Taylor Drive Chesterfield, MO Nestled on a beautiful half-acre lot and with over 4,700 square feet of living space, this...	4 beds \| 5 baths \| 4,708 sq.ft.	$845,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.94% Airbnb Rental Income: $2029 Traditional Rental Income: $5045 Airbnb ROI: -0.56% Traditional ROI: 3.94%
1611 Walpole Drive #C Chesterfield, MO Stunning 2 Bedroom, 2 full-bath second story condo in desired Chesterfield surrounded by t...	2 beds \| 2 baths \| 1,675 sq.ft.	$249,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.22% Airbnb Rental Income: $1683 Traditional Rental Income: $1943 Airbnb ROI: 0.13% Traditional ROI: 3.22%
1205 Patchwork Fields Chesterfield, MO Located in prestigious Fienup Farms, this impressive 1.5 story, built in 2021 by Claymont ...	5 beds \| 5 baths \| 6,339 sq.ft.	$2,375,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 0.19% Airbnb Rental Income: $2408 Traditional Rental Income: $4553 Airbnb ROI: -1.05% Traditional ROI: 0.19%
15371 Timber Hill Lane Chesterfield, MO Completely updated 2-story home in a quiet cul-de-sac! Step inside to discover gleaming wo...	4 beds \| 3 baths \| 2,398 sq.ft.	$579,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 3.52% Airbnb Rental Income: $2023 Traditional Rental Income: $3008 Airbnb ROI: 0.73% Traditional ROI: 3.52%
13453 Coliseum Drive #E Chesterfield, MO Location, location, location! This move-in ready condo in Chesterfield has so much to offe...	2 beds \| 2 baths \| 1,000 sq.ft.	$135,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 4.79% Airbnb Rental Income: $1683 Traditional Rental Income: $1467 Airbnb ROI: 2.84% Traditional ROI: 4.79%
2335 Manor Grove Drive #9 Chesterfield, MO Welcome to a beautiful 2-bedroom, 2-bath condo located in the heart of West County! Enjoy ...	2 beds \| 2 baths \| 1,294 sq.ft.	$219,900	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.7% Airbnb Rental Income: $1683 Traditional Rental Income: $1519 Airbnb ROI: -0.77% Traditional ROI: 0.7%
15261 Springrun Drive Chesterfield, MO Your dream home awaits in the Upper Conway Area! Welcome to 15261 Springrun Dr. Chesterfie...	5 beds \| 3 baths \| 2,347 sq.ft.	$495,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.5% Airbnb Rental Income: $2408 Traditional Rental Income: $2616 Airbnb ROI: 1.78% Traditional ROI: 3.5%
718 Silver Buck Lane Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home w/ Finished L...	5 beds \| 5 baths \| 5,244 sq.ft.	$1,840,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.7% Airbnb Rental Income: $2408 Traditional Rental Income: $4801 Airbnb ROI: -0.05% Traditional ROI: 1.7%
724 Silver Buck Lane Chesterfield, MO MAGNIFICENT Ranch home w/ Finished Lower Level in a FABULOUS LOCATION! This Spec House is ...	4 beds \| 4 baths \| 5,535 sq.ft.	$1,805,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.75% Airbnb Rental Income: $2023 Traditional Rental Income: $4800 Airbnb ROI: -0.22% Traditional ROI: 1.75%
805 Silver Buck Lane Chesterfield, MO New Construction (HOME TO BE BUILT)! Built by one of St. Louis' premier hands on builders ...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,640,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 0.79% Airbnb Rental Income: $1454 Traditional Rental Income: $2918 Airbnb ROI: -0.46% Traditional ROI: 0.79%
14308 Conway Meadows Court #203 Chesterfield, MO This refined two-bedroom condo in the prestigious Conway Meadows offers rare MAIN-LEVEL ac...	2 beds \| 2 baths \| 2,179 sq.ft.	$399,900	Airbnb cash on cash: -0.74% Traditional cash on cash: 1.77% Airbnb Rental Income: $1683 Traditional Rental Income: $2157 Airbnb ROI: -0.74% Traditional ROI: 1.77%
312 Indigo Court #37-303 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$757,800	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.48% Airbnb Rental Income: $1454 Traditional Rental Income: $3010 Airbnb ROI: -0.33% Traditional ROI: 2.48%
314 Indigo Court #37-302 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$719,800	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.68% Airbnb Rental Income: $1454 Traditional Rental Income: $3017 Airbnb ROI: -0.3% Traditional ROI: 2.68%
16536 Yellowwood Drive #48-301 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$770,082	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.43% Airbnb Rental Income: $1454 Traditional Rental Income: $3011 Airbnb ROI: -0.34% Traditional ROI: 2.43%
16534 Yellowwood Drive #48-302 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$764,800	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.46% Airbnb Rental Income: $1454 Traditional Rental Income: $3017 Airbnb ROI: -0.34% Traditional ROI: 2.46%
1511 Hampton Hall Drive #19 & 20 Chesterfield, MO Welcome to this amazing Chesterfield Condo at almost 3000 sqft! This 3-bedroom 2.5 bath pr...	3 beds \| 3 baths \| 2,960 sq.ft.	$320,000	Airbnb cash on cash: -4.31% Traditional cash on cash: 1.15% Airbnb Rental Income: $1454 Traditional Rental Income: $2666 Airbnb ROI: -4.31% Traditional ROI: 1.15%
16532 Yellowwood Drive #48-303 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$794,800	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.07% Airbnb Rental Income: $1454 Traditional Rental Income: $2825 Airbnb ROI: -0.36% Traditional ROI: 2.07%
232 Cordovan Commons Parkway Chesterfield, MO Welcome to this beautifully maintained 2-Bedroom, 2 Full Bath Villa located in the highly ...	2 beds \| 2 baths \| 1,480 sq.ft.	$425,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.69% Airbnb Rental Income: $1683 Traditional Rental Income: $1963 Airbnb ROI: -0.2% Traditional ROI: 1.69%
15009 Claymoor Court #11 Chesterfield, MO Welcome to effortless living in this spacious 2 bed, 2.5 bath condo located in the highly...	2 beds \| 3 baths \| 2,088 sq.ft.	$325,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.5% Airbnb Rental Income: $1683 Traditional Rental Income: $2208 Airbnb ROI: -0.75% Traditional ROI: 2.5%
2259 Sycamore Drive Chesterfield, MO Exceptional Living in Chesterfieldâs Twin Estates Experience refined living at 2259 Syca...	5 beds \| 4 baths \| 3,952 sq.ft.	$799,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.58% Airbnb Rental Income: $2408 Traditional Rental Income: $3552 Airbnb ROI: 0.25% Traditional ROI: 2.58%

Real Estate investment in Chesterfield, MO

There are 101 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $654,900 and the average price per square foot is $193. In October 2025, the average monthly cash on cash return in Chesterfield is 2.00%. The average monthly rental income in Chesterfield is $2,977.

Chesterfield, MO Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 101 investment properties available for sale in Chesterfield.

In 2025, the best neighborhood to buy investment property is Chesterfield.

The ROI for Short-Term is higher than the Long-Term in Chesterfield with average rental income of $2,023.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, MO

596 Eagle Manor Lane

Chesterfield, MO

4 beds | 5 baths | 5,393 sq.ft.

$700,000

Airbnb cash on cash: 0%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $2023

Traditional Rental Income: $4673

Airbnb ROI: 0%

Traditional ROI: 4.86%

13555 Coliseum Drive #G

Chesterfield, MO

2 beds | 2 baths | 1,020 sq.ft.

$138,000

Airbnb cash on cash: 3.04%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1683

Traditional Rental Income: $1430

Airbnb ROI: 3.04%

Traditional ROI: 4.67%

1315 Wildhorse Meadows Drive

Chesterfield, MO

5 beds | 6 baths | 7,679 sq.ft.

$1,695,000

Airbnb cash on cash: -0.89%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2408

Traditional Rental Income: $6288

Airbnb ROI: -0.89%

Traditional ROI: 1.95%

1621 Walpole Drive #B

Chesterfield, MO

4 beds | 3 baths | 1,561 sq.ft.

$335,000

Airbnb cash on cash: 0.53%

Traditional cash on cash: 8.28%

Airbnb Rental Income: $2023

Traditional Rental Income: $3936

Airbnb ROI: 0.53%

Traditional ROI: 8.28%

14361 Stablestone Court

Chesterfield, MO

4 beds | 3 baths | 3,144 sq.ft.

$565,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2023

Traditional Rental Income: $3037

Airbnb ROI: 0.61%

Traditional ROI: 3.53%

2323 Manor Grove Drive #4

Chesterfield, MO

3 beds | 2 baths | 1,490 sq.ft.

$240,000

Airbnb cash on cash: -2.22%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $1454

Traditional Rental Income: $1747

Airbnb ROI: -2.22%

Traditional ROI: 0.98%

1556 Wildhorse Parkway Drive

Chesterfield, MO

5 beds | 5 baths | 4,260 sq.ft.

$1,299,900

Airbnb cash on cash: 0.23%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $2408

Traditional Rental Income: $4691

Airbnb ROI: 0.23%

Traditional ROI: 2.61%

16078 Meadow Oak Drive

Chesterfield, MO

4 beds | 3 baths | 2,668 sq.ft.

$530,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $2023

Traditional Rental Income: $2777

Airbnb ROI: 0.69%