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.

Single Family Homes for Sale in Chesterfield, MO

Search for Single Family Residential for Sale in Chesterfield, Missouri. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 74 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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%
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%
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%
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%
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%
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%
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%
2029 Brook Hill Lane Chesterfield, MO Welcome to this stunning 2 Sty Home. 5-bedroom, 4.5-bath Home offering over 4,200 square f...	5 beds \| 4 baths \| 4,296 sq.ft.	$1,265,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 2.29% Airbnb Rental Income: $1462 Traditional Rental Income: $4870 Airbnb ROI: -0.98% Traditional ROI: 2.29%
295 Ridge Trail Drive Chesterfield, MO Please wear booties. Luxury Living on a Premier Corner Lot. From the moment you pull into ...	5 beds \| 4 baths \| 2,284 sq.ft.	$649,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.33% Airbnb Rental Income: $1462 Traditional Rental Income: $3172 Airbnb ROI: -0.21% Traditional ROI: 3.33%
2221 Stonegate Manor Court Chesterfield, MO This stunning 5-bedroom, 4.5-bath Colonial is perfectly situated on a .56-acre cul-de-sac ...	5 beds \| 4 baths \| 5,191 sq.ft.	$900,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 2.03% Airbnb Rental Income: $1462 Traditional Rental Income: $3551 Airbnb ROI: -0.98% Traditional ROI: 2.03%
1401 Fox Hill Farms Court Chesterfield, MO Prestigious homes in this highly coveted Chesterfield neighborhood rarely come to market, ...	5 beds \| 7 baths \| 7,880 sq.ft.	$2,349,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 1.13% Airbnb Rental Income: $1462 Traditional Rental Income: $6659 Airbnb ROI: -1.45% Traditional ROI: 1.13%
960 Chesterfield Parkway E Chesterfield, MO Prime opportunity along highly visible Chesterfield Parkway! This versatile 1.31 acre parc...	2 beds \| 1 baths \| 1,424 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.14% Airbnb Rental Income: $null Traditional Rental Income: $1494 Airbnb ROI: N/A Traditional ROI: 0.14%
400 Conway Meadows Drive Chesterfield, MO Tucked just inside the gated entrance and steps from the lake, this beautifully maintained...	3 beds \| 3 baths \| 2,965 sq.ft.	$715,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 1.2% Airbnb Rental Income: $1188 Traditional Rental Income: $2732 Airbnb ROI: -1.7% Traditional ROI: 1.2%
14555 Coeur Dalene Ct 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 \| 2,211 sq.ft.	$449,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.92% Airbnb Rental Income: $1936 Traditional Rental Income: $2571 Airbnb ROI: 1.2% Traditional ROI: 3.92%
2133 Hunters Way Court Chesterfield, MO Welcome to 2133 Hunters Way Ct â a gracious 4-bedroom, 3-bath ranch offering multiple li...	4 beds \| 3 baths \| 3,988 sq.ft.	$525,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.15% Airbnb Rental Income: $1936 Traditional Rental Income: $2715 Airbnb ROI: 0.52% Traditional ROI: 3.15%
1326 Top Of The Hill Road Chesterfield, MO Welcome to this massive and luxurious Ranch home with beautiful 3/4" Hickory hardwood thro...	3 beds \| 2 baths \| 2,811 sq.ft.	$949,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 1.02% Airbnb Rental Income: $1188 Traditional Rental Income: $2412 Airbnb ROI: -0.81% Traditional ROI: 1.02%
14949 Royalbrook Drive Chesterfield, MO Fabulous ranch-style home ideally situated in the heart of Chesterfield, offering effortle...	4 beds \| 3 baths \| 2,422 sq.ft.	$559,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 2.95% Airbnb Rental Income: $1936 Traditional Rental Income: $2690 Airbnb ROI: 0.53% Traditional ROI: 2.95%
1518 Mallard Pointe Court Chesterfield, MO Experience refined living in this exceptional luxury villa located in the highly desirable...	4 beds \| 4 baths \| 4,212 sq.ft.	$899,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.35% Airbnb Rental Income: $1936 Traditional Rental Income: $3404 Airbnb ROI: -1.01% Traditional ROI: 1.35%
14715 Timberway Court Chesterfield, MO Located in desirable Chesterfield with quick Highway 40 access, this fully remodeled 2-sto...	4 beds \| 3 baths \| 2,620 sq.ft.	$725,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 1.97% Airbnb Rental Income: $1936 Traditional Rental Income: $2773 Airbnb ROI: -0.02% Traditional ROI: 1.97%
978 Silver Buck Lane Chesterfield, MO Impeccably upgraded. Perfectly located. Impossible to ignore, where every detail has been ...	4 beds \| 4 baths \| 4,043 sq.ft.	$1,199,900	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.78% Airbnb Rental Income: $1936 Traditional Rental Income: $3354 Airbnb ROI: -0.95% Traditional ROI: 0.78%
1228 Gooseberry Lane Chesterfield, MO Welcome to 1228 Gooseberry Lane, where custom design, thoughtful upgrades, and everyday co...	4 beds \| 6 baths \| 5,266 sq.ft.	$1,800,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 1.8% Airbnb Rental Income: $1936 Traditional Rental Income: $6433 Airbnb ROI: -1.2% Traditional ROI: 1.8%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesterfield, MO

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%

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%

Traditional ROI: 2.56%

2052 Tramore Ct

Chesterfield, MO

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

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%

744 Silver Buck Lane

Chesterfield, MO

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

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%