Real Estate Investment Properties for Sale in Winchester, MO

Looking for investment property in Winchester, MO with high ROI ?

Explore a variety of short-term homes & houses in Winchester, MO. Invest wisely with VRBO & Winchester, 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 Winchester, MO

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
413 Lindy Boulevard Winchester, MO NO SHOW *8-7-2025 Carpets are being cleaned. Friday 8-8- is good to go! Honey Stop The ...	4 beds \| 2 baths \| 1,566 sq.ft.	$315,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 2.19% Airbnb Rental Income: $2473 Traditional Rental Income: $1283 Airbnb ROI: 4.18% Traditional ROI: 2.19%
425 Chamberlin Drive Winchester, MO Welcome to 425 Chamberlin Drive, a spacious 3 bedroom, 2 full bathroom home that has been ...	3 beds \| 2 baths \| 1,439 sq.ft.	$258,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 5.31% Airbnb Rental Income: $1660 Traditional Rental Income: $1883 Airbnb ROI: 2.49% Traditional ROI: 5.31%
61 Hillcrest Boulevard Winchester, MO "Your Gonna Love it!!" This 3 bedroom 1.5 bath home is a complete package. All appliances...	3 beds \| 2 baths \| 1,267 sq.ft.	$272,500	Airbnb cash on cash: 2.36% Traditional cash on cash: 4.28% Airbnb Rental Income: $1660 Traditional Rental Income: $1689 Airbnb ROI: 2.36% Traditional ROI: 4.28%
Investment Properties for Sale in Other Cities of Missouri
1761 N East Street Webb City , MO Step into this enchanting property sitting pretty on 3.75 acres, hugged by Mother Nature's...	4 beds \| 5 baths \| 5,106 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $2668 Airbnb ROI: N/A Traditional ROI: 2.88%
1128 N Blackstone Avenue Republic , MO This beautifully maintained 3-bedroom, 2-bath, 3-car garage home is perfectly situated on ...	3 beds \| 2 baths \| 1,336 sq.ft.	$269,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 4.7% Airbnb Rental Income: $1464 Traditional Rental Income: $1714 Airbnb ROI: 2.02% Traditional ROI: 4.7%
2 Monarch Trace Court #103 Chesterfield , MO Welcome to 2 Monarch Trace Ct #103âyour ultra-convenient, centrally located ground-floor...	2 beds \| 2 baths \| 1,186 sq.ft.	$240,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.55% Airbnb Rental Income: $1536 Traditional Rental Income: $1682 Airbnb ROI: -0.05% Traditional ROI: 2.55%
12647 State Road TT Festus , MO Don't miss out on this horse gem just out of town! Rehabbed ranch sitting on 8+ acres with...	3 beds \| 2 baths \| 1,586 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $1834 Airbnb ROI: N/A Traditional ROI: 3.56%
940 E Loren Street Springfield , MO Welcome to 940 E Loren St - a character-filled home nestled in one of Springfield's most s...	2 beds \| 1 baths \| 2,080 sq.ft.	$150,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 8.31% Airbnb Rental Income: $1213 Traditional Rental Income: $1513 Airbnb ROI: 3.49% Traditional ROI: 8.31%
24506 State Road A Richland , MO Charming Remodeled Home on 1.52 Peaceful Acres!! Welcome to this beautifully remodeled 3-b...	3 beds \| 2 baths \| 1,380 sq.ft.	$229,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.68% Airbnb Rental Income: $null Traditional Rental Income: $2063 Airbnb ROI: N/A Traditional ROI: 7.68%
409 S Lakeshore Drive Raymore , MO Charming True Ranch in coveted Lake Community! Welcome home to this beautifully maintained...	3 beds \| 3 baths \| 2,576 sq.ft.	$390,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 5.23% Airbnb Rental Income: $1586 Traditional Rental Income: $2655 Airbnb ROI: 1.07% Traditional ROI: 5.23%
2304 S 12th Street Ozark , MO REDUCED! Stone and brick front home situated in a small Quaint subdivision on the south si...	3 beds \| 2 baths \| 1,712 sq.ft.	$299,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 4.23% Airbnb Rental Income: $1728 Traditional Rental Income: $1756 Airbnb ROI: 2.44% Traditional ROI: 4.23%
51 Fox Hollow Lane Eolia , MO Custom built 2-story home on 10.64 acres with three fenced pastures and huge 4 stall horse...	4 beds \| 5 baths \| 5,412 sq.ft.	$719,900	Airbnb cash on cash: -0.7% Traditional cash on cash: 5.64% Airbnb Rental Income: $1119 Traditional Rental Income: $5000 Airbnb ROI: -0.7% Traditional ROI: 5.64%
1812 Jessica Hills Court Washington , MO Spacious open floor plan in Washington on cul-de-sac in established neighborhood! This po...	4 beds \| 2 baths \| 1,800 sq.ft.	$300,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 5.33% Airbnb Rental Income: $1580 Traditional Rental Income: $2062 Airbnb ROI: 2.02% Traditional ROI: 5.33%
464 Cedar Heights Drive unit: 3 B #3 B Camdenton , MO HOW RARE 36-Foot Slip & Lakefront Living with No Steps! Don't miss this incredible lakefro...	2 beds \| 2 baths \| 1,050 sq.ft.	$269,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.58% Airbnb Rental Income: $1180 Traditional Rental Income: $1662 Airbnb ROI: 0.18% Traditional ROI: 3.58%
71 Sesame Street Camdenton , MO Step inside this charming Mid-Century Modern split-level home where character and comfort ...	3 beds \| 3 baths \| 3,139 sq.ft.	$315,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 6.59% Airbnb Rental Income: $995 Traditional Rental Income: $2427 Airbnb ROI: 0.56% Traditional ROI: 6.59%
406 Valley Street Lathrop , MO Welcome home to 406 Valley Streetâwhere charm meets modern updates in this beautifully r...	3 beds \| 2 baths \| 1,714 sq.ft.	$225,000	Airbnb cash on cash: 4.98% Traditional cash on cash: 7.38% Airbnb Rental Income: $2081 Traditional Rental Income: $2055 Airbnb ROI: 4.98% Traditional ROI: 7.38%
14815 CC Highway Holt , MO Escape to Your Own Private Oasis! Dreaming of wide-open spaces and a life at a little slow...	4 beds \| 2 baths \| 2,558 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $2739 Airbnb ROI: N/A Traditional ROI: 2.28%

Real Estate investment in Winchester, MO

There are 4 properties for sale in the city of Winchester . The median list price in Winchester is $265,250 and the average price per square foot is $201. In September 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $1,529.

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

There are 4 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $1,529.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, MO

413 Lindy Boulevard

Winchester, MO

4 beds | 2 baths | 1,566 sq.ft.

$315,000

Airbnb cash on cash: 4.18%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $2473

Traditional Rental Income: $1283

Airbnb ROI: 4.18%

Traditional ROI: 2.19%

425 Chamberlin Drive

Winchester, MO

3 beds | 2 baths | 1,439 sq.ft.

$258,000

Airbnb cash on cash: 2.49%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1660

Traditional Rental Income: $1883

Airbnb ROI: 2.49%

Traditional ROI: 5.31%

61 Hillcrest Boulevard

Winchester, MO

3 beds | 2 baths | 1,267 sq.ft.

$272,500

Airbnb cash on cash: 2.36%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $1660

Traditional Rental Income: $1689

Airbnb ROI: 2.36%

Traditional ROI: 4.28%

Investment Properties for Sale in Other Cities of Missouri

Webb City , MO

4 beds | 5 baths | 5,106 sq.ft.

$635,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.88%

Airbnb Rental Income: $null

Traditional Rental Income: $2668

Airbnb ROI: N/A

Traditional ROI: 2.88%

Republic , MO

3 beds | 2 baths | 1,336 sq.ft.

$269,900

Airbnb cash on cash: 2.02%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $1464

Traditional Rental Income: $1714

Airbnb ROI: 2.02%

Traditional ROI: 4.7%

Chesterfield , MO

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

$240,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $1536

Traditional Rental Income: $1682

Airbnb ROI: -0.05%

Traditional ROI: 2.55%

Festus , MO

3 beds | 2 baths | 1,586 sq.ft.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1834

Airbnb ROI: N/A

Traditional ROI: 3.56%

Springfield , MO

2 beds | 1 baths | 2,080 sq.ft.

$150,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 8.31%

Airbnb Rental Income: $1213

Traditional Rental Income: $1513

Airbnb ROI: 3.49%

Traditional ROI: 8.31%

Richland , MO

3 beds | 2 baths | 1,380 sq.ft.

$229,000