Real Estate Investments for Sale in Chesterfield, MO With High ROI

Are you looking for a vacation rental in Chesterfield, MO? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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 49 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
415 Herworth Drive Chesterfield, MO Nestled within the prestigious Forest Hills Club Estates, 415 Herworth is aone-ok-a-kind r...	5 beds \| 4 baths \| 4,727 sq.ft.	$849,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.93% Airbnb Rental Income: $null Traditional Rental Income: $3186 Airbnb ROI: N/A Traditional ROI: 1.93%
16514 Honey Locust Drive #6-303 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	2 beds \| 4 baths \| 2,370 sq.ft.	$846,056	Airbnb cash on cash: N/A Traditional cash on cash: 0.62% Airbnb Rental Income: $null Traditional Rental Income: $2469 Airbnb ROI: N/A Traditional ROI: 0.62%
2206 Twin Estates Circle Chesterfield, MO Located in the A+ Rockwood School District & sitting on one of the largest lots in the nei...	4 beds \| 3 baths \| 3,633 sq.ft.	$675,000	Airbnb cash on cash: 4.98% Traditional cash on cash: 2.62% Airbnb Rental Income: $5672 Traditional Rental Income: $3049 Airbnb ROI: 4.98% Traditional ROI: 2.62%
16839 Kehrsbrooke Court Chesterfield, MO Professional pics should be back Tuesday AM... Wonderful opportunity in sought after Kehrs...	5 beds \| 4 baths \| 3,837 sq.ft.	$760,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $3340 Airbnb ROI: N/A Traditional ROI: 2.68%
1776 Golden Lake Court Chesterfield, MO Welcome Home to your Newly Remodeled Classic 1.5 Story boasting Entirely New Kitchen featu...	4 beds \| 3 baths \| 3,218 sq.ft.	$550,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.52% Airbnb Rental Income: $5672 Traditional Rental Income: $2867 Airbnb ROI: 6.77% Traditional ROI: 3.52%
1154 Greystone Manor Parkway Chesterfield, MO	5 beds \| 7 baths \| 5,400 sq.ft.	$1,275,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.18% Airbnb Rental Income: $null Traditional Rental Income: $3845 Airbnb ROI: N/A Traditional ROI: 1.18%
16986 Barn Owl Lane Chesterfield, MO Located in prestigious Fienup Farms, this impressive 1.5 story leaves nothing to be desire...	5 beds \| 5 baths \| 6,590 sq.ft.	$2,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.02% Airbnb Rental Income: $null Traditional Rental Income: $3743 Airbnb ROI: N/A Traditional ROI: -0.02%
16524 Yellowwood Drive #45-302 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$742,417	Airbnb cash on cash: 4.12% Traditional cash on cash: 1.14% Airbnb Rental Income: $5804 Traditional Rental Income: $2582 Airbnb ROI: 4.12% Traditional ROI: 1.14%
1532 Yarmouth Point Drive Chesterfield, MO 1532 Yarmouth Point is ready for a new owner with a passion to renovate solid but dated ho...	4 beds \| 3 baths \| 2,640 sq.ft.	$465,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 3.78% Airbnb Rental Income: $5672 Traditional Rental Income: $2663 Airbnb ROI: 8.09% Traditional ROI: 3.78%
11 Greymore Drive Chesterfield, MO NEWSELLER OFFERING $10,000 CREDIT FOR RATE BUYDOWN OR CLOSING COSTS! So Much House und...	5 beds \| 4 baths \| 1,759 sq.ft.	$482,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $2908 Airbnb ROI: N/A Traditional ROI: 4.48%
17003 Waterside Chesterfield, MO Welcome to 17003 Waterside Hts, a luxury location on a premium lot in the prestigious Fien...	4 beds \| 4 baths \| 4,146 sq.ft.	$1,550,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 1.13% Airbnb Rental Income: $5672 Traditional Rental Income: $3542 Airbnb ROI: 1.83% Traditional ROI: 1.13%
274 Glen Hollow Drive Chesterfield, MO Opportunity knocks! Here is your chance to live in desirable Westbury Manor at a great pri...	5 beds \| 3 baths \| 3,125 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2784 Airbnb ROI: N/A Traditional ROI: 5.27%
301 Diplomat Lane Chesterfield, MO PRICE ADJUSTMENTâ Upgrade your lifestyle with this stunning top to bottom luxury renovat...	4 beds \| 3 baths \| 3,553 sq.ft.	$698,750	Airbnb cash on cash: 5.15% Traditional cash on cash: 2.59% Airbnb Rental Income: $5672 Traditional Rental Income: $2872 Airbnb ROI: 5.15% Traditional ROI: 2.59%
14509 Brittania Drive Chesterfield, MO Stunning 4 bed/3.5 bath 2 story home with updates galore in the sought after Scarborough s...	4 beds \| 4 baths \| 2,619 sq.ft.	$629,900	Airbnb cash on cash: 5.67% Traditional cash on cash: 2.41% Airbnb Rental Income: $5672 Traditional Rental Income: $2619 Airbnb ROI: 5.67% Traditional ROI: 2.41%
2015 Brook Hill Court Chesterfield, MO Discover luxury living in this stunning all-brick ranch located in prestigious Brook Hill ...	3 beds \| 4 baths \| 4,698 sq.ft.	$985,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 1.38% Airbnb Rental Income: $5804 Traditional Rental Income: $3054 Airbnb ROI: 3.12% Traditional ROI: 1.38%
394 Oak Stand Path Chesterfield, MO Stunning 1.5 Story home in desired Reserve at Chesterfield with 5 beds & 4.5 baths and app...	5 beds \| 5 baths \| 6,187 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $3530 Airbnb ROI: N/A Traditional ROI: 1.62%
15702 Country Ridge Drive Chesterfield, MO Beautifully updated brick 2 Sty in sought after Meadowbrook Farm! Classic center hall floo...	4 beds \| 3 baths \| 2,604 sq.ft.	$555,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 2.74% Airbnb Rental Income: $5672 Traditional Rental Income: $2603 Airbnb ROI: 6.47% Traditional ROI: 2.74%
15019 Manor Creek Drive Chesterfield, MO Stately 2-story; popular Claymont Manor subdivision; over 3,500 SF of fin. living space; W...	4 beds \| 3 baths \| 4,218 sq.ft.	$675,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 1.93% Airbnb Rental Income: $5672 Traditional Rental Income: $2544 Airbnb ROI: 5.1% Traditional ROI: 1.93%
1591 Milbridge Drive Chesterfield, MO Welcome to your dream home in the heart of Chesterfield! This newly updated 2-story, 4bed,...	4 beds \| 4 baths \| 3,270 sq.ft.	$435,000	Airbnb cash on cash: 8.16% Traditional cash on cash: 3.96% Airbnb Rental Income: $5672 Traditional Rental Income: $2828 Airbnb ROI: 8.16% Traditional ROI: 3.96%
15806 Thomas Ridge Court Chesterfield, MO Welcome to 15806 Thomas Ridge Court in the Villages at Baxter Ridge. This spacious and inv...	3 beds \| 4 baths \| 3,227 sq.ft.	$459,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 2.59% Airbnb Rental Income: $5804 Traditional Rental Income: $2720 Airbnb ROI: 7.08% Traditional ROI: 2.59%
298 Herworth Drive Chesterfield, MO Pristine, picturesque, private, Open, Bright & light describes this Elegantly updated 2sty...	4 beds \| 6 baths \| 4,550 sq.ft.	$1,099,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 1.53% Airbnb Rental Income: $5672 Traditional Rental Income: $3691 Airbnb ROI: 2.36% Traditional ROI: 1.53%
15506 Chequer Drive Chesterfield, MO Charming Colonial 4 BR/2.5 bath two-story Chesterfield home in sought after Highcroft Esta...	4 beds \| 3 baths \| 2,352 sq.ft.	$470,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 3.25% Airbnb Rental Income: $5672 Traditional Rental Income: $2399 Airbnb ROI: 8.12% Traditional ROI: 3.25%
795 TBB Schaeffer's Grove Court Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home with Finished...	5 beds \| 5 baths \| 5,293 sq.ft.	$1,510,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $3399 Airbnb ROI: N/A Traditional ROI: 0.43%
782 TBB 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.	$1,310,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.24% Airbnb Rental Income: $5804 Traditional Rental Income: $2727 Airbnb ROI: 1.82% Traditional ROI: 0.24%
1047 Tidewater Place Court Chesterfield, MO Presenting an enchanting New England style home situated on a 1.24-acre lot in T&C. This h...	5 beds \| 5 baths \| 4,431 sq.ft.	$1,185,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $4035 Airbnb ROI: N/A Traditional ROI: 1.9%
741 TBB Silver Buck Lane Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home w/ Finished L...	5 beds \| 5 baths \| 5,292 sq.ft.	$1,510,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.87% Airbnb Rental Income: $null Traditional Rental Income: $4011 Airbnb ROI: N/A Traditional ROI: 0.87%
770 TBB Schaeffer's Grove Court Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home with Finishe...	5 beds \| 5 baths \| 5,293 sq.ft.	$1,510,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $3399 Airbnb ROI: N/A Traditional ROI: 0.43%
14885 Olive Boulevard Chesterfield, MO Charming and Profitable? Imagine having your very own resort-like oasis right in your back...	5 beds \| 3 baths \| 3,688 sq.ft.	$564,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2794 Airbnb ROI: N/A Traditional ROI: 3.26%
777 TBB Schaeffer's Grove Court Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home with Finished...	5 beds \| 5 baths \| 5,293 sq.ft.	$1,510,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $3399 Airbnb ROI: N/A Traditional ROI: 0.43%
771 TBB Schaeffer's Grove Court Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! MAGNIFICENT 1.5 Story home with Finished...	5 beds \| 5 baths \| 5,293 sq.ft.	$1,510,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.87% Airbnb Rental Income: $null Traditional Rental Income: $4011 Airbnb ROI: N/A Traditional ROI: 0.87%
744 TBB Silver Buck Lane Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! Built by one of St. Louis' premier hands...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,310,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.24% Airbnb Rental Income: $5804 Traditional Rental Income: $2727 Airbnb ROI: 1.82% Traditional ROI: 0.24%
17282 Jeffreys Crossing Lane Chesterfield, MO Whoever said that you canât have it all hasnât seen this! Elegantly expansive, this cu...	4 beds \| 3 baths \| 4,916 sq.ft.	$1,299,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 0.23% Airbnb Rental Income: $5672 Traditional Rental Income: $2786 Airbnb ROI: 1.68% Traditional ROI: 0.23%
253 Heather Crest Drive Chesterfield, MO Welcome Home! This Beautiful 2 story, all brick home is loaded with updates & charm. Talk ...	4 beds \| 3 baths \| 2,440 sq.ft.	$610,000	Airbnb cash on cash: 6% Traditional cash on cash: 2.36% Airbnb Rental Income: $5672 Traditional Rental Income: $2461 Airbnb ROI: 6% Traditional ROI: 2.36%
15554 Clover Ridge Drive Chesterfield, MO Welcome to 15554 Clover Ridge Drive! This home sits on a premium corner lot in a neighborh...	4 beds \| 3 baths \| 2,468 sq.ft.	$529,000	Airbnb cash on cash: 7.1% Traditional cash on cash: 3.06% Airbnb Rental Income: $5672 Traditional Rental Income: $2542 Airbnb ROI: 7.1% Traditional ROI: 3.06%
16533 Yellowwood Drive #69-302 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$749,072	Airbnb cash on cash: 4.07% Traditional cash on cash: 1.02% Airbnb Rental Income: $5804 Traditional Rental Income: $2519 Airbnb ROI: 4.07% Traditional ROI: 1.02%
413 Forsheer Drive Chesterfield, MO NEW PRICE!!! A wonderful opportunity awaits in much sought-after Claymont Estates subdivis...	4 beds \| 4 baths \| 2,783 sq.ft.	$585,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 3.07% Airbnb Rental Income: $5672 Traditional Rental Income: $2859 Airbnb ROI: 6.14% Traditional ROI: 3.07%
747 TBB Silver Buck Lane Chesterfield, MO New Construction, Chesterfield, Rockwood Schools! Built by one of St. Louis' premier hands...	3 beds \| 4 baths \| 4,534 sq.ft.	$1,310,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.44% Airbnb Rental Income: $5804 Traditional Rental Income: $2970 Airbnb ROI: 1.82% Traditional ROI: 0.44%
16521 Yellowwood Drive #72-301 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$769,179	Airbnb cash on cash: 3.91% Traditional cash on cash: 1.2% Airbnb Rental Income: $5804 Traditional Rental Income: $2704 Airbnb ROI: 3.91% Traditional ROI: 1.2%
58 Highland Park Drive Chesterfield, MO Sitting on the fairway to the first hole of the Pristine Four Seasons Country Club, I intr...	4 beds \| 3 baths \| 1,911 sq.ft.	$419,900	Airbnb cash on cash: 9.33% Traditional cash on cash: 3.41% Airbnb Rental Income: $5672 Traditional Rental Income: $2205 Airbnb ROI: 9.33% Traditional ROI: 3.41%
325 Mistflower Court #18-303 Chesterfield, MO Trendy new Clifton plan by Fischer Homes in beautiful Wildhorse Village. This townhome fea...	3 beds \| 4 baths \| 2,370 sq.ft.	$730,173	Airbnb cash on cash: 4.77% Traditional cash on cash: 1.91% Airbnb Rental Income: $5804 Traditional Rental Income: $2704 Airbnb ROI: 4.77% Traditional ROI: 1.91%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesterfield, MO

415 Herworth Drive

Chesterfield, MO

5 beds | 4 baths | 4,727 sq.ft.

$849,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.93%

Airbnb Rental Income: $null

Traditional Rental Income: $3186

Airbnb ROI: N/A

Traditional ROI: 1.93%

16514 Honey Locust Drive #6-303

Chesterfield, MO

2 beds | 4 baths | 2,370 sq.ft.

$846,056

Airbnb cash on cash: N/A

Traditional cash on cash: 0.62%

Airbnb Rental Income: $null

Traditional Rental Income: $2469

Airbnb ROI: N/A

Traditional ROI: 0.62%

2206 Twin Estates Circle

Chesterfield, MO

4 beds | 3 baths | 3,633 sq.ft.

$675,000

Airbnb cash on cash: 4.98%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $5672

Traditional Rental Income: $3049

Airbnb ROI: 4.98%

Traditional ROI: 2.62%

16839 Kehrsbrooke Court

Chesterfield, MO

5 beds | 4 baths | 3,837 sq.ft.

$760,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.68%

Airbnb Rental Income: $null

Traditional Rental Income: $3340

Airbnb ROI: N/A

Traditional ROI: 2.68%

1776 Golden Lake Court

Chesterfield, MO

4 beds | 3 baths | 3,218 sq.ft.

$550,000

Airbnb cash on cash: 6.77%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $5672

Traditional Rental Income: $2867

Airbnb ROI: 6.77%

Traditional ROI: 3.52%

1154 Greystone Manor Parkway

Chesterfield, MO

5 beds | 7 baths | 5,400 sq.ft.

$1,275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3845

Airbnb ROI: N/A

Traditional ROI: 1.18%

16986 Barn Owl Lane

Chesterfield, MO

5 beds | 5 baths | 6,590 sq.ft.

$2,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.02%

Airbnb Rental Income: $null

Traditional Rental Income: $3743

Airbnb ROI: N/A

Traditional ROI: -0.02%

16524 Yellowwood Drive #45-302

Chesterfield, MO

3 beds | 4 baths | 2,370 sq.ft.

$742,417

Airbnb cash on cash: 4.12%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $5804

Traditional Rental Income: $2582

Airbnb ROI: 4.12%