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.

Investment Property for Sale in Winterset, IA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: 8.98% Airbnb Rental Income: $null Traditional Rental Income: $1622 Airbnb ROI: N/A Traditional ROI: 8.98%
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%
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%
2197 175th Court Winterset, IA Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement abou...	2 beds \| 2 baths \| 1,024 sq.ft.	$339,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 2.95% Airbnb Rental Income: $978 Traditional Rental Income: $1551 Airbnb ROI: 0.05% Traditional ROI: 2.95%
411 W Madison Street Winterset, IA Looking to downsize? Just starting out? This is home! 2 bed, 1 bath tri-plex features zero...	2 beds \| 1 baths \| 1,031 sq.ft.	$210,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 7.31% Airbnb Rental Income: $978 Traditional Rental Income: $2110 Airbnb ROI: -0.15% Traditional ROI: 7.31%
405 W Madison Street Winterset, IA Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-s...	2 beds \| 1 baths \| 1,031 sq.ft.	$210,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 6.16% Airbnb Rental Income: $978 Traditional Rental Income: $1881 Airbnb ROI: -0.15% Traditional ROI: 6.16%
203 W Green Street Winterset, IA You will love all the space in this UNIQUE 2000+ sq ft home on a large corner lot! Main le...	4 beds \| 3 baths \| 2,080 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.69% Airbnb Rental Income: $null Traditional Rental Income: $2882 Airbnb ROI: N/A Traditional ROI: 7.69%
804 N 4th Avenue Winterset, IA Welcome to a truly extraordinary home where timeless craftsmanship, modern luxury, and stu...	4 beds \| 2 baths \| 1,880 sq.ft.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 6.9%
113 S 3rd Street Winterset, IA Move-in ready and totally remodeled 3-bed 2.5-bath ranch! Everything you need is on the ma...	3 beds \| 3 baths \| 1,006 sq.ft.	$234,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.95% Airbnb Rental Income: $1549 Traditional Rental Income: $1609 Airbnb ROI: 2.67% Traditional ROI: 4.95%
615 N 1st Avenue Winterset, IA This beautifully remodeled residence combines timeless charm with modern comfort. Step ins...	4 beds \| 2 baths \| 2,724 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $2701 Airbnb ROI: N/A Traditional ROI: 5.31%
719 E Washington Street Winterset, IA Discover the ultimate "wow factor" in this stunning Winterset property, truly like anythin...	3 beds \| 3 baths \| 2,432 sq.ft.	$579,900	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.03% Airbnb Rental Income: $1549 Traditional Rental Income: $2936 Airbnb ROI: -0.36% Traditional ROI: 3.03%
1795 Millstream Court Winterset, IA This stunning 1.5-story home sits on just over 3 acres of paved countryside 3 miles north ...	5 beds \| 4 baths \| 2,229 sq.ft.	$629,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $3253 Airbnb ROI: N/A Traditional ROI: 3.12%
400 N 14th Avenue Winterset, IA This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless...	4 beds \| 3 baths \| 1,540 sq.ft.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2539 Airbnb ROI: N/A Traditional ROI: 3.03%
118 N 5th Street Winterset, IA Charm with economy! That's what this 5BR, 1 bath, 1.5 story home offers! Great natural lig...	3 beds \| 1 baths \| 1,523 sq.ft.	$169,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 8.4% Airbnb Rental Income: $1549 Traditional Rental Income: $1849 Airbnb ROI: 3.76% Traditional ROI: 8.4%
310 W Washington Street Winterset, IA Welcome to 310 W. Washington, where this classic Craftsman blends character with modern co...	3 beds \| 2 baths \| 2,430 sq.ft.	$349,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 5.08% Airbnb Rental Income: $1549 Traditional Rental Income: $2626 Airbnb ROI: 0.43% Traditional ROI: 5.08%
409 W Madison Street Winterset, IA Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-s...	2 beds \| 1 baths \| 1,031 sq.ft.	$210,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 6.42% Airbnb Rental Income: $978 Traditional Rental Income: $1878 Airbnb ROI: 0.13% Traditional ROI: 6.42%
407 W Madison Street Winterset, IA Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-s...	2 beds \| 1 baths \| 1,031 sq.ft.	$206,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 6.59% Airbnb Rental Income: $978 Traditional Rental Income: $1878 Airbnb ROI: 0.18% Traditional ROI: 6.59%
212 N 14th Avenue Winterset, IA Sweet ranch home located on a quiet street. The open concept floor plan makes this house f...	3 beds \| 2 baths \| 1,204 sq.ft.	$295,000	Airbnb cash on cash: 1% Traditional cash on cash: 4.27% Airbnb Rental Income: $1549 Traditional Rental Income: $2011 Airbnb ROI: 1% Traditional ROI: 4.27%
1024 W Summit Street Winterset, IA In town acreage opportunity. 3-bedroom, 1-bath home on 9.88 m/l acres located just outside...	3 beds \| 1 baths \| 2,286 sq.ft.	$399,990	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.92% Airbnb Rental Income: $1549 Traditional Rental Income: $1862 Airbnb ROI: 0.89% Traditional ROI: 2.92%
2230 260th Street Winterset, IA Set on 19.5 acres just outside Winterset, this property offers a rare combination of scale...	3 beds \| 4 baths \| 3,660 sq.ft.	$899,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.84% Airbnb Rental Income: $1549 Traditional Rental Income: $3257 Airbnb ROI: -0.73% Traditional ROI: 1.84%
2980 Clark Tower Rd. Winterset, IA Located in scenic Madison County this newly built home and buildings offers peace and quie...	2 beds \| 2 baths \| 4,424 sq.ft.	$478,750	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.78% Airbnb Rental Income: $978 Traditional Rental Income: $2289 Airbnb ROI: -0.93% Traditional ROI: 2.78%
2210 Ash Tree Drive Winterset, IA Jackson Walkout Ranch Plan with over-sized 3 car garage. Front porch with 2 stone base pos...	3 beds \| 2 baths \| 1,400 sq.ft.	$395,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.68% Airbnb Rental Income: $1549 Traditional Rental Income: $2227 Airbnb ROI: 1.64% Traditional ROI: 4.68%
1516 Roseman Bridge Road Winterset, IA Welcome to your own private retreat on 20 beautiful acres near Winterset. This thoughtfull...	3 beds \| 4 baths \| 2,138 sq.ft.	$899,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.43% Airbnb Rental Income: $1549 Traditional Rental Income: $2736 Airbnb ROI: -0.52% Traditional ROI: 1.43%
1509 W South Street Winterset, IA Move-in ready and full of charm! This well-cared-for, one owner 3-bedroom, 2-bath home sit...	3 beds \| 2 baths \| 864 sq.ft.	$274,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 4.11% Airbnb Rental Income: $1549 Traditional Rental Income: $1702 Airbnb ROI: 1.79% Traditional ROI: 4.11%
222 Oak Tree Drive Winterset, IA Well cared for one-owner home featuring 3 bedrooms, 3 bathrooms with high 9 ft ceilings th...	3 beds \| 3 baths \| 1,574 sq.ft.	$389,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.62% Airbnb Rental Income: $1549 Traditional Rental Income: $2302 Airbnb ROI: 0.34% Traditional ROI: 3.62%
309 Maple Point Winterset, IA Stryker Ranch New Construction with oversized 3 car garage. Front porch with 2 stone base ...	3 beds \| 2 baths \| 1,400 sq.ft.	$382,500	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.89% Airbnb Rental Income: $1549 Traditional Rental Income: $2227 Airbnb ROI: 1.75% Traditional ROI: 4.89%
2223 Holliwell Valley Court Winterset, IA Perfect acreage alert! This exceptional walkout ranch is ready for new owners to move in a...	4 beds \| 4 baths \| 1,972 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $2787 Airbnb ROI: N/A Traditional ROI: 2.45%

Real Estate investment in Winterset, IA

There are 60 properties for sale in the city of Winterset . The median list price in Winterset is $224,884 and the average price per square foot is $128. In June 2026, the average monthly cash on cash return in Winterset is 5.00%. The average monthly rental income in Winterset is $2,257.

Winterset, IA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 60 investment properties available for sale in Winterset.

In 2026, the best neighborhood to buy investment property is Winterset.

The ROI for Long-Term is higher than the Short-Term in Winterset with average rental income of $2,257.

Your search for investment property begins and ends here

Investment Property for Sale in Winterset, IA

703 W North Street

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%

1913 N 1st Street

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%

301 N 15th Avenue

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%

505 E Court Avenue

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%

802 N 10th Avenue

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%

406 N 7th Street

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%

619 N 10th Street

Winterset, IA

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

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%