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
1104 Cantina Drive Chesterfield, MO Absolutely adorable 3-bed, 2.5-bath, 1,736 sqft all-brick townhome. Ready to move in for s...	3 beds \| 3 baths \| 1,736 sq.ft.	$220,000	Airbnb cash on cash: -1.82% Traditional cash on cash: 4.77% Airbnb Rental Income: $1188 Traditional Rental Income: $2174 Airbnb ROI: -1.82% Traditional ROI: 4.77%
15574 Highcroft Drive Chesterfield, MO Beautifully updated and move-in-ready, this home offers a charming blend of style and func...	4 beds \| 3 baths \| 2,907 sq.ft.	$525,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 3.58% Airbnb Rental Income: $1936 Traditional Rental Income: $2817 Airbnb ROI: 0.74% Traditional ROI: 3.58%
14812 Brook Hill Drive Chesterfield, MO Discover timeless elegance in this inviting 2 story home nestled in the desirable Brook Hi...	4 beds \| 6 baths \| 5,643 sq.ft.	$1,350,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.28% Airbnb Rental Income: $1936 Traditional Rental Income: $6722 Airbnb ROI: -0.95% Traditional ROI: 3.28%
15049 Claymoor Court #17 Chesterfield, MO Updated and move-in ready...End unit condo in wonderful Broadmoor. Features large open liv...	3 beds \| 3 baths \| 2,088 sq.ft.	$315,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 3.29% Airbnb Rental Income: $1188 Traditional Rental Income: $2437 Airbnb ROI: -2.23% Traditional ROI: 3.29%
27 Bonhomme Grove Court Chesterfield, MO Luxury villa living at its finest in this stunning 1.5-story residence, thoughtfully desig...	4 beds \| 5 baths \| 6,993 sq.ft.	$1,399,999	Airbnb cash on cash: -1.72% Traditional cash on cash: 0.85% Airbnb Rental Income: $1936 Traditional Rental Income: $4765 Airbnb ROI: -1.72% Traditional ROI: 0.85%
1 Monarch Trace Court #303 Chesterfield, MO Welcome to easy, low-maintenance living in the heart of Chesterfield! This well-maintained...	2 beds \| 2 baths \| 1,186 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $1680 Airbnb ROI: N/A Traditional ROI: 1.9%
1556 Wildhorse Parkway Drive Chesterfield, MO This exquisite newly built. 1.5 Story home 0.72 Acres in Chesterfield! 5 Beds & 4 1/2 Bath...	5 beds \| 5 baths \| 4,288 sq.ft.	$1,149,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.08% Airbnb Rental Income: $1462 Traditional Rental Income: $4691 Airbnb ROI: -0.35% Traditional ROI: 3.08%
14380 Cedar Springs Drive Chesterfield, MO Easy, low-maintenance living in Town & Country-with space and flexibility today's buyers a...	4 beds \| 4 baths \| 4,684 sq.ft.	$589,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 2.56% Airbnb Rental Income: $1936 Traditional Rental Income: $3465 Airbnb ROI: -1.15% Traditional ROI: 2.56%
2052 Tramore Ct Chesterfield, MO Buy this home if YOU Are Not Satisfied with your purchase in 12 Months I'LL Buy It back or...	3 beds \| 3 baths \| 1,620 sq.ft.	$299,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 6.16% Airbnb Rental Income: $1188 Traditional Rental Income: $2401 Airbnb ROI: 0.49% Traditional ROI: 6.16%
753 Silver Buck Lane Chesterfield, MO New Construction (Currently Under Construction)! Built by one of St. Louis' premier hands ...	4 beds \| 4 baths \| 5,535 sq.ft.	$1,855,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -0.28% Airbnb Rental Income: $1936 Traditional Rental Income: $2987 Airbnb ROI: -1.19% Traditional ROI: -0.28%
1512 Bedford Forge Court #11 Chesterfield, MO Beautifully updated end-unit condo in the highly desirable Brandywine community, located i...	1 beds \| 2 baths \| 1,292 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.52% Airbnb Rental Income: $null Traditional Rental Income: $1521 Airbnb ROI: N/A Traditional ROI: 1.52%
744 Silver Buck Lane Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MACNIFICENT 1.5 Story home with Finished...	5 beds \| 5 baths \| 5,293 sq.ft.	$1,890,000	Airbnb cash on cash: -1.43% Traditional cash on cash: -0.32% Airbnb Rental Income: $1462 Traditional Rental Income: $2987 Airbnb ROI: -1.43% Traditional ROI: -0.32%
730 Willow Spring Hill Court Chesterfield, MO Welcome to this spacious and beautifully maintained villa located in the desirable Cedar S...	5 beds \| 4 baths \| 5,344 sq.ft.	$499,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 0.8% Airbnb Rental Income: $1462 Traditional Rental Income: $2416 Airbnb ROI: -2.17% Traditional ROI: 0.8%
15940 Woodlet Way Court Chesterfield, MO HOLD ONTO YOUR HATS! This one is a PEACH! Just what you have been looking for. Gracious h...	4 beds \| 3 baths \| 2,537 sq.ft.	$575,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.33% Airbnb Rental Income: $1936 Traditional Rental Income: $3019 Airbnb ROI: 0.36% Traditional ROI: 3.33%
13459 Coliseum Drive Chesterfield, MO Yes! Conventional financing is available. Chesterfield 3-level townhouse with 2 defined co...	3 beds \| 3 baths \| 1,800 sq.ft.	$195,000	Airbnb cash on cash: -1.65% Traditional cash on cash: 6.09% Airbnb Rental Income: $1188 Traditional Rental Income: $2234 Airbnb ROI: -1.65% Traditional ROI: 6.09%
409 Griffith Lane Chesterfield, MO This is your chance to own a one-of-a-kind retreat where the world fades away on exclusive...	5 beds \| 3 baths \| 4,219 sq.ft.	$975,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.42% Airbnb Rental Income: $1462 Traditional Rental Income: $3093 Airbnb ROI: -0.86% Traditional ROI: 1.42%
13453 Coliseum Drive #E Chesterfield, MO Prime Chesterfield location! Donât miss this beautifully maintained and move-in ready co...	2 beds \| 2 baths \| 1,000 sq.ft.	$124,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $1467 Airbnb ROI: N/A Traditional ROI: 5.25%
14623 Kendall Ridge Drive Chesterfield, MO Elegant 4-bedroom, 2 1/2 bath villa located in a gated community! Offering a secluded and ...	4 beds \| 3 baths \| 3,664 sq.ft.	$1,090,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.08% Airbnb Rental Income: $1936 Traditional Rental Income: $2579 Airbnb ROI: -1.06% Traditional ROI: 0.08%
776 Schaeffer's Grove Court Chesterfield, MO New Construction (HOME TO BE BUILT)! MAGNIFICENT 1.5 Story home w/ Finished Lower Level in...	5 beds \| 5 baths \| 5,244 sq.ft.	$1,840,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 2.07% Airbnb Rental Income: $1462 Traditional Rental Income: $5396 Airbnb ROI: -0.48% Traditional ROI: 2.07%
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: -0.6% Traditional cash on cash: 0.79% Airbnb Rental Income: $1188 Traditional Rental Income: $2918 Airbnb ROI: -0.6% Traditional ROI: 0.79%
1511 Hampton Hall Drive #19 & 20 Chesterfield, MO Experience unmatched value in the Chesterfield condo market with this penthouse-level Bran...	3 beds \| 3 baths \| 2,960 sq.ft.	$265,000	Airbnb cash on cash: -5.87% Traditional cash on cash: 1.59% Airbnb Rental Income: $1188 Traditional Rental Income: $2666 Airbnb ROI: -5.87% Traditional ROI: 1.59%
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: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $1963 Airbnb ROI: N/A Traditional ROI: 1.69%
13503 Coliseum Drive Chesterfield, MO Holy smokes! Can you believe a true 4 bedroom, 2.5 bath townhouse in the Chesterfield? Wha...	4 beds \| 3 baths \| 1,696 sq.ft.	$195,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 5.72% Airbnb Rental Income: $1936 Traditional Rental Income: $2285 Airbnb ROI: 1.07% Traditional ROI: 5.72%
1318 Conway Oaks Drive Chesterfield, MO Step into this stunning 1.5-story home offering 4+ bedrooms and 3 full and 1 half baths, t...	4 beds \| 4 baths \| 3,565 sq.ft.	$750,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.49% Airbnb Rental Income: $1936 Traditional Rental Income: $3872 Airbnb ROI: -0.01% Traditional ROI: 3.49%
15648 Sugarridge Court Chesterfield, MO HERE IS YOUR CHANCE FOR A WONDERFUL HOME! Freshly painted main level. Kitchen and laundry ...	4 beds \| 4 baths \| 3,166 sq.ft.	$499,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.67% Airbnb Rental Income: $1936 Traditional Rental Income: $3253 Airbnb ROI: 0.75% Traditional ROI: 4.67%
170 Saddleford Drive Chesterfield, MO Step into a home designed for the way you live in the heart of Westbury Manor. This stunni...	4 beds \| 3 baths \| 3,196 sq.ft.	$575,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 2.99% Airbnb Rental Income: $1936 Traditional Rental Income: $2762 Airbnb ROI: 0.5% Traditional ROI: 2.99%
14121 Westernmill Drive Chesterfield, MO Beautifully updated 4 bed, 2.5 bath 2-story on a stunning lot with mature trees and privat...	4 beds \| 3 baths \| 2,721 sq.ft.	$625,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 2.72% Airbnb Rental Income: $1936 Traditional Rental Income: $2783 Airbnb ROI: 0.39% Traditional ROI: 2.72%
2130 Willow Way Court Chesterfield, MO Back on market and better than ever- come make it yours. This beautifully updates home off...	4 beds \| 3 baths \| 2,964 sq.ft.	$574,400	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.01% Airbnb Rental Income: $1936 Traditional Rental Income: $2864 Airbnb ROI: 0.33% Traditional ROI: 3.01%
1121 Matador Drive Chesterfield, MO This inviting and well-maintained townhome offers the perfect blend of comfort and conveni...	3 beds \| 3 baths \| 1,736 sq.ft.	$199,900	Airbnb cash on cash: -1.9% Traditional cash on cash: 4.91% Airbnb Rental Income: $1188 Traditional Rental Income: $2093 Airbnb ROI: -1.9% Traditional ROI: 4.91%
2316 Coventry Farm Court Chesterfield, MO Charming 2-story home ideally located just off Kehrs Mill Rd, offering convenient access t...	4 beds \| 4 baths \| 3,248 sq.ft.	$600,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.36% Airbnb Rental Income: $1936 Traditional Rental Income: $3117 Airbnb ROI: 0.34% Traditional ROI: 3.36%
1521 Hedgeford Drive #8 Chesterfield, MO Welcome Home to 1521 Hedgeford Dr, Unit #8! Step into this beautifully maintained first-f...	2 beds \| 2 baths \| 976 sq.ft.	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $1370 Airbnb ROI: N/A Traditional ROI: 2.52%
16543 Yellowwood Drive #66-302 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$789,900	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.09% Airbnb Rental Income: $1188 Traditional Rental Income: $2823 Airbnb ROI: -0.66% Traditional ROI: 2.09%
16545 Yellowwood Drive #66-303 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$805,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.02% Airbnb Rental Income: $1188 Traditional Rental Income: $2815 Airbnb ROI: -0.67% Traditional ROI: 2.02%
16541 Yellowwood Drive #66-301 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$809,900	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.01% Airbnb Rental Income: $1188 Traditional Rental Income: $2820 Airbnb ROI: -0.67% Traditional ROI: 2.01%
1525 Hampton Hall Drive #5 Chesterfield, MO Welcome to this Beautiful first floor condo in the highly sought after Brandywine Communit...	2 beds \| 2 baths \| 1,547 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $2008 Airbnb ROI: N/A Traditional ROI: 2.99%
16553 Yellowwood Drive #63-302 Chesterfield, MO New construction by Fischer Homes in beautiful Wildhorse Village featuring the Clifton pla...	3 beds \| 4 baths \| 2,370 sq.ft.	$720,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.35% Airbnb Rental Income: $1188 Traditional Rental Income: $2797 Airbnb ROI: -0.63% Traditional ROI: 2.35%
Lot 8 Sommerlin Chesterfield, MO	4 beds \| 2 baths \| 2,671 sq.ft.	$552,218	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.07% Airbnb Rental Income: $1936 Traditional Rental Income: $2174 Airbnb ROI: 0.62% Traditional ROI: 2.07%
6 Upper Conway Lane Chesterfield, MO Experience elevated living in this exceptional villa, perfectly situated in one of Chester...	3 beds \| 5 baths \| 6,374 sq.ft.	$1,100,000	Airbnb cash on cash: -1.94% Traditional cash on cash: 0.97% Airbnb Rental Income: $1188 Traditional Rental Income: $3784 Airbnb ROI: -1.94% Traditional ROI: 0.97%

Real Estate investment in Chesterfield, MO

There are 104 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $570,730 and the average price per square foot is $204. In May 2026, the average monthly cash on cash return in Chesterfield is 2.00%. The average monthly rental income in Chesterfield is $2,797.

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

There are 104 investment properties available for sale in Chesterfield.

In 2026, the best neighborhood to buy investment property is Chesterfield.

The ROI for Long-Term is higher than the Short-Term in Chesterfield with average rental income of $2,797.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, MO

1104 Cantina Drive

Chesterfield, MO

3 beds | 3 baths | 1,736 sq.ft.

$220,000

Airbnb cash on cash: -1.82%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1188

Traditional Rental Income: $2174

Airbnb ROI: -1.82%

Traditional ROI: 4.77%

15574 Highcroft Drive

Chesterfield, MO

4 beds | 3 baths | 2,907 sq.ft.

$525,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $1936

Traditional Rental Income: $2817

Airbnb ROI: 0.74%

Traditional ROI: 3.58%

14812 Brook Hill Drive

Chesterfield, MO

4 beds | 6 baths | 5,643 sq.ft.

$1,350,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $1936

Traditional Rental Income: $6722

Airbnb ROI: -0.95%

Traditional ROI: 3.28%

15049 Claymoor Court #17

Chesterfield, MO

3 beds | 3 baths | 2,088 sq.ft.

$315,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1188

Traditional Rental Income: $2437

Airbnb ROI: -2.23%

Traditional ROI: 3.29%

27 Bonhomme Grove Court

Chesterfield, MO

4 beds | 5 baths | 6,993 sq.ft.

$1,399,999

Airbnb cash on cash: -1.72%

Traditional cash on cash: 0.85%

Airbnb Rental Income: $1936

Traditional Rental Income: $4765

Airbnb ROI: -1.72%

Traditional ROI: 0.85%

1 Monarch Trace Court #303

Chesterfield, MO

2 beds | 2 baths | 1,186 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.9%

Airbnb Rental Income: $null

Traditional Rental Income: $1680

Airbnb ROI: N/A

Traditional ROI: 1.9%

1556 Wildhorse Parkway Drive

Chesterfield, MO

5 beds | 5 baths | 4,288 sq.ft.

$1,149,900

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1462

Traditional Rental Income: $4691

Airbnb ROI: -0.35%

Traditional ROI: 3.08%

14380 Cedar Springs Drive

Chesterfield, MO

4 beds | 4 baths | 4,684 sq.ft.

$589,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $1936

Traditional Rental Income: $3465

Airbnb ROI: -1.15%