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
1754 Summer Lake Dr 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 \| 2,522 sq.ft.	$499,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.68% Airbnb Rental Income: $1881 Traditional Rental Income: $2718 Airbnb ROI: 0.82% Traditional ROI: 3.68%
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.	$690,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.95% Airbnb Rental Income: $1881 Traditional Rental Income: $4673 Airbnb ROI: -0.17% Traditional ROI: 4.95%
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: 1.54% Traditional cash on cash: 4.67% Airbnb Rental Income: $1446 Traditional Rental Income: $1430 Airbnb ROI: 1.54% 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: -1.47% Traditional cash on cash: 1.95% Airbnb Rental Income: $1311 Traditional Rental Income: $6288 Airbnb ROI: -1.47% 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 \| 2,617 sq.ft.	$329,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.61% Airbnb Rental Income: $1881 Traditional Rental Income: $2755 Airbnb ROI: 0.17% Traditional ROI: 4.61%
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: -2.94% Traditional cash on cash: 0.98% Airbnb Rental Income: $1257 Traditional Rental Income: $1747 Airbnb ROI: -2.94% 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: -0.53% Traditional cash on cash: 2.61% Airbnb Rental Income: $1311 Traditional Rental Income: $4691 Airbnb ROI: -0.53% Traditional ROI: 2.61%
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: -0.54% Traditional cash on cash: 4.05% Airbnb Rental Income: $1881 Traditional Rental Income: $4795 Airbnb ROI: -0.54% Traditional ROI: 4.05%
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: 0.88% Traditional cash on cash: 4.55% Airbnb Rental Income: $1881 Traditional Rental Income: $3092 Airbnb ROI: 0.88% Traditional ROI: 4.55%
831 Stone Meadow Drive Chesterfield, MO Location, location, Chesterfield's Meadows at Stonehill is nestled in a superb location b...	2 beds \| 3 baths \| 2,712 sq.ft.	$549,900	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.75% Airbnb Rental Income: $1446 Traditional Rental Income: $2063 Airbnb ROI: -1.28% Traditional ROI: 0.75%
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.	$1,095,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.97% Airbnb Rental Income: $1881 Traditional Rental Income: $3338 Airbnb ROI: -0.95% Traditional ROI: 0.97%
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: -1.46% Traditional cash on cash: -0.06% Airbnb Rental Income: $1257 Traditional Rental Income: $2987 Airbnb ROI: -1.46% 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: -1.46% Traditional cash on cash: -0.06% Airbnb Rental Income: $1257 Traditional Rental Income: $2987 Airbnb ROI: -1.46% Traditional ROI: -0.06%
16094 Meadow Oak Drive Chesterfield, MO This beautifully updated 2 story home offers timeless style & modern comfort in one of Che...	4 beds \| 5 baths \| 3,400 sq.ft.	$600,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.61% Airbnb Rental Income: $1881 Traditional Rental Income: $3780 Airbnb ROI: 0.32% Traditional ROI: 4.61%
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.	$795,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 4.25% Airbnb Rental Income: $1881 Traditional Rental Income: $5045 Airbnb ROI: -0.7% Traditional ROI: 4.25%
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: -0.71% Traditional cash on cash: 3.22% Airbnb Rental Income: $1446 Traditional Rental Income: $1943 Airbnb ROI: -0.71% 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: -1.47% Traditional cash on cash: 0.19% Airbnb Rental Income: $1311 Traditional Rental Income: $4553 Airbnb ROI: -1.47% Traditional ROI: 0.19%
409 Griffith Lane Chesterfield, MO Upgraded NEW Roof 2025! Welcome to a truly rare findâan exceptional retreat where timele...	5 beds \| 3 baths \| 4,219 sq.ft.	$975,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.42% Airbnb Rental Income: $1311 Traditional Rental Income: $3093 Airbnb ROI: -1% Traditional ROI: 1.42%
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.	$569,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.59% Airbnb Rental Income: $1881 Traditional Rental Income: $3008 Airbnb ROI: 0.53% Traditional ROI: 3.59%
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: -1.1% Traditional cash on cash: 0.08% Airbnb Rental Income: $1881 Traditional Rental Income: $2579 Airbnb ROI: -1.1% Traditional ROI: 0.08%
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: -1.72% Traditional cash on cash: 0.7% Airbnb Rental Income: $1446 Traditional Rental Income: $1519 Airbnb ROI: -1.72% Traditional ROI: 0.7%
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: -0.29% Traditional cash on cash: 1.75% Airbnb Rental Income: $1881 Traditional Rental Income: $4800 Airbnb ROI: -0.29% 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: -0.56% Traditional cash on cash: 0.79% Airbnb Rental Income: $1257 Traditional Rental Income: $2918 Airbnb ROI: -0.56% Traditional ROI: 0.79%
104 Amiot Court Chesterfield, MO Welcome home to this light-filled 3 bedroom, 3 bathroom Villa thatâs equal parts spa...	3 beds \| 3 baths \| 2,841 sq.ft.	$430,000	Airbnb cash on cash: -1.78% Traditional cash on cash: 2.29% Airbnb Rental Income: $1257 Traditional Rental Income: $2498 Airbnb ROI: -1.78% Traditional ROI: 2.29%
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.	$735,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.58% Airbnb Rental Income: $1257 Traditional Rental Income: $3010 Airbnb ROI: -0.55% Traditional ROI: 2.58%
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: -0.54% Traditional cash on cash: 2.68% Airbnb Rental Income: $1257 Traditional Rental Income: $3017 Airbnb ROI: -0.54% Traditional ROI: 2.68%
1511 Hampton Hall Drive #19 & 20 Chesterfield, MO Welcome to the PENTHOUSE of Condos right here in Chesterfield! At almost 3000 sqft., this ...	3 beds \| 3 baths \| 2,960 sq.ft.	$300,000	Airbnb cash on cash: -5.11% Traditional cash on cash: 1.29% Airbnb Rental Income: $1257 Traditional Rental Income: $2666 Airbnb ROI: -5.11% Traditional ROI: 1.29%
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: -1.4% Traditional cash on cash: 2.5% Airbnb Rental Income: $1446 Traditional Rental Income: $2208 Airbnb ROI: -1.4% 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: -0.97% Traditional cash on cash: 2.58% Airbnb Rental Income: $1311 Traditional Rental Income: $3552 Airbnb ROI: -0.97% Traditional ROI: 2.58%
1255 Walnut Hill Farm Drive Chesterfield, MO Welcome home to this ranch home on 3.3 private acres. Traditional floor plan with floor to...	3 beds \| 5 baths \| 5,190 sq.ft.	$765,000	Airbnb cash on cash: -1.74% Traditional cash on cash: 2.71% Airbnb Rental Income: $1257 Traditional Rental Income: $4031 Airbnb ROI: -1.74% Traditional ROI: 2.71%
14361 White Birch Valley Lane Chesterfield, MO Hurry \| Desired Chesterfield Location - Highways, Shopping, Restaurants \| Quiet Cul-de-sac...	4 beds \| 3 baths \| 3,043 sq.ft.	$499,900	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.93% Airbnb Rental Income: $1881 Traditional Rental Income: $2877 Airbnb ROI: 0.72% Traditional ROI: 3.93%
308 Indigo Court #40-301 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,370 sq.ft.	$819,800	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.98% Airbnb Rental Income: $1257 Traditional Rental Income: $2829 Airbnb ROI: -0.6% Traditional ROI: 1.98%
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: 1.34% Traditional cash on cash: 6.24% Airbnb Rental Income: $1881 Traditional Rental Income: $2285 Airbnb ROI: 1.34% Traditional ROI: 6.24%
351 Oak Stand Court Chesterfield, MO Welcome to 351 Oak Stand Court, a stunning 6 bedroom, 4.5-bath home offering over 5,300 sq...	5 beds \| 5 baths \| 5,323 sq.ft.	$1,300,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.09% Airbnb Rental Income: $1311 Traditional Rental Income: $5013 Airbnb ROI: -1.31% Traditional ROI: 2.09%
15648 Sugarridge Court Chesterfield, MO HERE IS YOUR CHANCE FOR A WONDERFUL HOME! Kitchen and laundry room refrigerators, Newer wa...	4 beds \| 4 baths \| 3,166 sq.ft.	$499,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.67% Airbnb Rental Income: $1881 Traditional Rental Income: $3253 Airbnb ROI: 0.65% Traditional ROI: 4.67%
202 Fick Farm Road Chesterfield, MO Welcome to 202 Fick Farm Rd, a stunning private retreat nestled on six lush, wooded acres ...	5 beds \| 5 baths \| 6,148 sq.ft.	$1,595,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 1.48% Airbnb Rental Income: $1311 Traditional Rental Income: $5047 Airbnb ROI: -1.31% Traditional ROI: 1.48%
1507 Timberlake Manor Parkway Chesterfield, MO The history of this home is charming, it is said this was a working farm with this home be...	4 beds \| 4 baths \| 3,920 sq.ft.	$675,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 4.11% Airbnb Rental Income: $1881 Traditional Rental Income: $3921 Airbnb ROI: 0.07% Traditional ROI: 4.11%
16590 Honey Locust Drive #15-302 Chesterfield, MO Trendy new Clifton Modern Farmhouse plan by Fischer Homes in beautiful Wildhorse Village. ...	3 beds \| 4 baths \| 2,515 sq.ft.	$825,899	Airbnb cash on cash: -0.6% Traditional cash on cash: 2.03% Airbnb Rental Income: $1257 Traditional Rental Income: $2877 Airbnb ROI: -0.6% Traditional ROI: 2.03%

Real Estate investment in Chesterfield, MO

There are 99 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $600,000 and the average price per square foot is $186. In December 2025, the average monthly cash on cash return in Chesterfield is 3.00%. The average monthly rental income in Chesterfield is $2,834.

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

There are 99 investment properties available for sale in Chesterfield.

In 2025, 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 $2,834.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, MO

1754 Summer Lake Dr

Chesterfield, MO

4 beds | 3 baths | 2,522 sq.ft.

$499,900

Airbnb cash on cash: 0.82%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1881

Traditional Rental Income: $2718

Airbnb ROI: 0.82%

Traditional ROI: 3.68%

596 Eagle Manor Lane

Chesterfield, MO

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

$690,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 4.95%

Airbnb Rental Income: $1881

Traditional Rental Income: $4673

Airbnb ROI: -0.17%

Traditional ROI: 4.95%

13555 Coliseum Drive #G

Chesterfield, MO

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

$138,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1446

Traditional Rental Income: $1430

Airbnb ROI: 1.54%

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: -1.47%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $1311

Traditional Rental Income: $6288

Airbnb ROI: -1.47%

Traditional ROI: 1.95%

1621 Walpole Drive #B

Chesterfield, MO

4 beds | 3 baths | 2,617 sq.ft.

$329,900

Airbnb cash on cash: 0.17%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $1881

Traditional Rental Income: $2755

Airbnb ROI: 0.17%

Traditional ROI: 4.61%

2323 Manor Grove Drive #4

Chesterfield, MO

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

$240,000

Airbnb cash on cash: -2.94%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $1257

Traditional Rental Income: $1747

Airbnb ROI: -2.94%

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: -0.53%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1311

Traditional Rental Income: $4691

Airbnb ROI: -0.53%

Traditional ROI: 2.61%

16446 Dapple Gray Court

Chesterfield, MO

4 beds | 5 baths | 5,368 sq.ft.

$799,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $1881

Traditional Rental Income: $4795

Airbnb ROI: -0.54%