Real Estate Investment Properties for Sale in Winterset, IA

Looking for investment property in Winterset, IA with high ROI ?

Explore a variety of short-term homes & houses in Winterset, IA. Invest wisely with VRBO & Winterset, IA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Winterset, IA

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

Showing 2 Condo 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
209 W Jefferson Street #23 Winterset, IA Experience elevated small-town living in this beautifully updated 3rd floor corner condo l...	2 beds \| 2 baths \| 1,080 sq.ft.	$210,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 6.06% Airbnb Rental Income: $978 Traditional Rental Income: $1899 Airbnb ROI: -0.34% Traditional ROI: 6.06%
209 W jefferson Street #17 Winterset, IA Experience elevated small-town living in this beautifully updated 3rd floor corner condo l...	2 beds \| 2 baths \| 1,065 sq.ft.	$210,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 6.06% Airbnb Rental Income: $978 Traditional Rental Income: $1899 Airbnb ROI: -0.34% Traditional ROI: 6.06%
Other Investment Properties for Sale in Winterset
703 W North Street Winterset , IA This Winterset Ranch has 2 spacious BRs and newer LVP flooring in main living area. Open L...	2 beds \| 1 baths \| 950 sq.ft.	$160,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 7% Airbnb Rental Income: $978 Traditional Rental Income: $1518 Airbnb ROI: 1.16% Traditional ROI: 7%
1913 N 1st Street Winterset , IA Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. T...	3 beds \| 3 baths \| 2,389 sq.ft.	$410,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 5.5% Airbnb Rental Income: $1549 Traditional Rental Income: $3144 Airbnb ROI: 0.18% Traditional ROI: 5.5%
301 N 15th Avenue Winterset , IA Welcome to 301 N 15th Avenue, a well-maintained home ideally located in a quiet, establish...	4 beds \| 3 baths \| 1,087 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2035 Airbnb ROI: N/A Traditional ROI: 4.31%
505 E Court Avenue Winterset , IA Step into timeless character with this stately 19th-century home, showcasing stunning orig...	5 beds \| 4 baths \| 4,200 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $3628 Airbnb ROI: N/A Traditional ROI: 3.81%
802 N 10th Avenue Winterset , IA Easy living in this open floor plan ranch home. A large covered front porch greets you as ...	4 beds \| 3 baths \| 1,555 sq.ft.	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2557 Airbnb ROI: N/A Traditional ROI: 3.16%
406 N 7th Street Winterset , IA This home was a complete remodel down to the studs in 2024, with New Electric, Plumbing, D...	2 beds \| 2 baths \| 1,042 sq.ft.	$215,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 6.4% Airbnb Rental Income: $978 Traditional Rental Income: $1741 Airbnb ROI: 0.93% Traditional ROI: 6.4%
619 N 10th Street Winterset , IA Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006...	3 beds \| 2 baths \| 1,095 sq.ft.	$225,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 5.59% Airbnb Rental Income: $1549 Traditional Rental Income: $1803 Airbnb ROI: 2.3% Traditional ROI: 5.59%
415 E Buchanan Street Winterset , IA Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1...	2 beds \| 1 baths \| 1,286 sq.ft.	$154,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 8.68% Airbnb Rental Income: $978 Traditional Rental Income: $1600 Airbnb ROI: 2.07% Traditional ROI: 8.68%
114 N 8th Avenue Winterset , IA Completely updated 3-bedroom, 2-bath home blending timeless character with extensive upgra...	3 beds \| 2 baths \| 1,545 sq.ft.	$245,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 7.34% Airbnb Rental Income: $1549 Traditional Rental Income: $2384 Airbnb ROI: 1.8% Traditional ROI: 7.34%
1405 W Jefferson Street Winterset , IA Welcome to this well-maintained 4 bedroom, 3 bathroom home offering just under 1,500 squar...	4 beds \| N/A baths \| 1,470 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $2179 Airbnb ROI: N/A Traditional ROI: 3.92%
1413 W Washington Street Winterset , IA Beautifully maintained, this 4-bedroom ranch offers easy single-level living with an invit...	4 beds \| 2 baths \| 1,270 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.64% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 6.64%
523 S 2nd Street Winterset , IA This conversion duplex offers the perfect opportunity to add value and generate strong ret...	5 beds \| 2 baths \| 1,556 sq.ft.	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.6% Airbnb Rental Income: $null Traditional Rental Income: $1622 Airbnb ROI: N/A Traditional ROI: 9.6%
521 W Hutchings Street Winterset , IA Walk out ranch home with huge yard! This is a must see property! You will appreciate the u...	3 beds \| 2 baths \| 838 sq.ft.	$299,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.72% Airbnb Rental Income: $1549 Traditional Rental Income: $1554 Airbnb ROI: 1.12% Traditional ROI: 2.72%
710 N 3rd Avenue Winterset , IA Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home...	3 beds \| 1 baths \| 962 sq.ft.	$234,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 4.68% Airbnb Rental Income: $1549 Traditional Rental Income: $1592 Airbnb ROI: 2.48% Traditional ROI: 4.68%

Your search for investment property begins and ends here

Condos for Sale in Winterset, IA

209 W Jefferson Street #23

Winterset, IA

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

$210,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $978

Traditional Rental Income: $1899

Airbnb ROI: -0.34%

Traditional ROI: 6.06%

209 W jefferson Street #17

Winterset, IA

2 beds | 2 baths | 1,065 sq.ft.

$210,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $978

Traditional Rental Income: $1899

Airbnb ROI: -0.34%

Traditional ROI: 6.06%

Other Investment Properties for Sale in Winterset

Winterset , IA

2 beds | 1 baths | 950 sq.ft.

$160,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 7%

Airbnb Rental Income: $978

Traditional Rental Income: $1518

Airbnb ROI: 1.16%

Traditional ROI: 7%

Winterset , IA

3 beds | 3 baths | 2,389 sq.ft.

$410,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1549

Traditional Rental Income: $3144

Airbnb ROI: 0.18%

Traditional ROI: 5.5%

Winterset , IA

4 beds | 3 baths | 1,087 sq.ft.

$300,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.31%

Airbnb Rental Income: $null

Traditional Rental Income: $2035

Airbnb ROI: N/A

Traditional ROI: 4.31%

Winterset , IA

5 beds | 4 baths | 4,200 sq.ft.

$595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.81%

Airbnb Rental Income: $null

Traditional Rental Income: $3628

Airbnb ROI: N/A

Traditional ROI: 3.81%

Winterset , IA

4 beds | 3 baths | 1,555 sq.ft.

$455,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.16%

Airbnb Rental Income: $null

Traditional Rental Income: $2557

Airbnb ROI: N/A

Traditional ROI: 3.16%

Winterset , IA

2 beds | 2 baths | 1,042 sq.ft.

$215,000

Airbnb cash on cash: 0.93%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $978

Traditional Rental Income: $1741

Airbnb ROI: 0.93%

Traditional ROI: 6.4%

Winterset , IA

3 beds | 2 baths | 1,095 sq.ft.

$225,000

Airbnb cash on cash: 2.3%