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
1203 Beaver Creek Road Chesterfield, MO Welcome to this beautifully updated multi-level home offering space, style, and convenienc...	4 beds \| 3 baths \| 2,349 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2721 Airbnb ROI: N/A Traditional ROI: 3.26%
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: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $1430 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.95% Airbnb Rental Income: $null Traditional Rental Income: $6288 Airbnb ROI: N/A Traditional ROI: 1.95%
1 Monarch Trace Court #307 Chesterfield, MO Welcome to Unit #307 at Monarch Trace, a top-floor 2-bedroom, 2-bath all electric condo wi...	2 beds \| 2 baths \| 1,186 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $1657 Airbnb ROI: N/A Traditional ROI: 2.1%
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: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2755 Airbnb ROI: N/A 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.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.45% Airbnb Rental Income: $null Traditional Rental Income: $1747 Airbnb ROI: N/A Traditional ROI: 1.45%
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.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $2063 Airbnb ROI: N/A Traditional ROI: 0.82%
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: N/A Traditional cash on cash: -0.06% Airbnb Rental Income: $null Traditional Rental Income: $2987 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -0.06% Airbnb Rental Income: $null Traditional Rental Income: $2987 Airbnb ROI: N/A Traditional ROI: -0.06%
15595 Meadowbrook Circle Lane Chesterfield, MO This meticulously maintained two-story residence in the esteemed Twin Estates At Meadowbro...	4 beds \| 4 baths \| 4,368 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $3201 Airbnb ROI: N/A Traditional ROI: 1.71%
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: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $5045 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $1943 Airbnb ROI: N/A Traditional ROI: 3.22%
409 Griffith Lane Chesterfield, MO Upgraded NEW Roof 2025! Over an acre private lot with 3 sides of wooded common ground. Wel...	5 beds \| 3 baths \| 4,219 sq.ft.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.42% Airbnb Rental Income: $null Traditional Rental Income: $3093 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.08% Airbnb Rental Income: $null Traditional Rental Income: $2579 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $5396 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.79% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.29% Airbnb Rental Income: $null Traditional Rental Income: $2498 Airbnb ROI: N/A Traditional ROI: 2.29%
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: N/A Traditional cash on cash: 1.29% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 1.29%
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%
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: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $4031 Airbnb ROI: N/A Traditional ROI: 2.71%
2209 Ridgley Woods Dr Chesterfield, MO From the moment you enter, this home feels like stepping into the pages of a luxury design...	5 beds \| 5 baths \| 8,140 sq.ft.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $6609 Airbnb ROI: N/A Traditional ROI: 2.48%
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: N/A Traditional cash on cash: 5.72% Airbnb Rental Income: $null Traditional Rental Income: $2285 Airbnb ROI: N/A Traditional ROI: 5.72%
39 White Plains Drive Chesterfield, MO This Great Home is Ready for it's New OwnerBeautiful Updated Kitchen Features Custom Cab...	4 beds \| 3 baths \| 2,092 sq.ft.	$449,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $2613 Airbnb ROI: N/A Traditional ROI: 4.01%
153 Vonbehren Drive Chesterfield, MO Meticuliously maintained 1.5-story villa in the sought-after Villas at Chesterfield Bluffs...	3 beds \| 3 baths \| 2,594 sq.ft.	$480,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $2704 Airbnb ROI: N/A Traditional ROI: 1.89%
865 Forest Trace Drive #C Chesterfield, MO Live in the heart of Chesterfield! This stylish 2 bedroom, 1.5 bath townhome offers the pe...	2 beds \| 2 baths \| 1,134 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $1527 Airbnb ROI: N/A Traditional ROI: 2.44%
655 Spyglass Summit Drive Chesterfield, MO EXQUISITE LUXURY VILLA IN PRESTIGIOUS GATED COMMUNITY: Discover unparalleled elegance in t...	3 beds \| 4 baths \| 3,874 sq.ft.	$739,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.33% Airbnb Rental Income: $null Traditional Rental Income: $2944 Airbnb ROI: N/A Traditional ROI: 1.33%
13430 Manorlac Drive Chesterfield, MO Welcome to this spacious and well-cared-for townhome in the heart of Chesterfield! Featuri...	3 beds \| 3 baths \| 1,970 sq.ft.	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.67% Airbnb Rental Income: $null Traditional Rental Income: $2365 Airbnb ROI: N/A Traditional ROI: 6.67%
2364 The Courts Drive Chesterfield, MO NEWLY RENOVATED, never been used former display home with fresh, designer renovations comp...	4 beds \| 4 baths \| 4,310 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3504 Airbnb ROI: N/A Traditional ROI: 3.22%
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: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2093 Airbnb ROI: N/A Traditional ROI: 4.91%
1505 Timberbluff Court Chesterfield, MO This gorgeous 2-story located on a quiet cul-de-sac tucked in the back of a lovely neighbo...	4 beds \| 4 baths \| 3,295 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $3574 Airbnb ROI: N/A Traditional ROI: 3.64%
16956 Bottlebrush Court Chesterfield, MO This luxurious in-ground pool with hot-tub, swim-up bar, volleyball net, basketball hoop, ...	5 beds \| 5 baths \| 7,046 sq.ft.	$1,699,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $5527 Airbnb ROI: N/A Traditional ROI: 1.63%
2316 Coventry Farm Court Chesterfield, MO Charming 2-story home perfectly situated on a level lot with a big, private backyard! Enjo...	4 beds \| 4 baths \| 3,145 sq.ft.	$699,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.75% Airbnb Rental Income: $null Traditional Rental Income: $3117 Airbnb ROI: N/A Traditional ROI: 2.75%
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: N/A Traditional cash on cash: 2.09% Airbnb Rental Income: $null Traditional Rental Income: $2823 Airbnb ROI: N/A 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.	$814,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $2815 Airbnb ROI: N/A Traditional ROI: 1.98%
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: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $2820 Airbnb ROI: N/A Traditional ROI: 2.01%
16906 Bottlebrush Court Chesterfield, MO Stunning Atrium Ranch located in The Arbors at Kehrs Mill, showcasing thoughtful details a...	5 beds \| 6 baths \| 4,746 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $6263 Airbnb ROI: N/A Traditional ROI: 2.98%
14316 Conway Meadows Court E #202 Chesterfield, MO Tremendous Value! Welcome to this spacious condo in the desirable, gated Conway Meadows co...	2 beds \| 2 baths \| 1,893 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2132 Airbnb ROI: N/A Traditional ROI: 3.03%
290 Kinderhook Drive Chesterfield, MO Step into this classic two-story home on a prime suburban lot complete with an in ground s...	4 beds \| 4 baths \| 3,137 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3286 Airbnb ROI: N/A Traditional ROI: 4.35%

Real Estate investment in Chesterfield, MO

There are 69 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $542,488 and the average price per square foot is $199. In February 2026, the average monthly cash on cash return in Chesterfield is 2.00%. The average monthly rental income in Chesterfield is $2,711.

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

There are 69 investment properties available for sale in Chesterfield.

In 2026, 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, MO

1203 Beaver Creek Road

Chesterfield, MO

4 beds | 3 baths | 2,349 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2721

Airbnb ROI: N/A

Traditional ROI: 3.26%

13555 Coliseum Drive #G

Chesterfield, MO

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

$138,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $1430

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: 1.95%

Airbnb Rental Income: $null

Traditional Rental Income: $6288

Airbnb ROI: N/A

Traditional ROI: 1.95%

1 Monarch Trace Court #307

Chesterfield, MO

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

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.1%

Airbnb Rental Income: $null

Traditional Rental Income: $1657

Airbnb ROI: N/A

Traditional ROI: 2.1%

1621 Walpole Drive #B

Chesterfield, MO

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

$329,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2755

Airbnb ROI: N/A

Traditional ROI: 4.61%

2323 Manor Grove Drive #4

Chesterfield, MO

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.45%

Airbnb Rental Income: $null

Traditional Rental Income: $1747

Airbnb ROI: N/A

Traditional ROI: 1.45%

831 Stone Meadow Drive

Chesterfield, MO

2 beds | 3 baths | 2,712 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.82%

Airbnb Rental Income: $null

Traditional Rental Income: $2063

Airbnb ROI: N/A

Traditional ROI: 0.82%

753 Silver Buck Lane

Chesterfield, MO

3 beds | 4 baths | 4,534 sq.ft.

$1,640,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2987

Airbnb ROI: N/A