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
410 N 6th Street Winterset, IA Pride of ownership in this spacious home! 3 bedrooms, 2 baths, over 2,000 sf finished spac...	3 beds \| 2 baths \| 1,400 sq.ft.	$290,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.01% Airbnb Rental Income: $1941 Traditional Rental Income: $2156 Airbnb ROI: 2.34% Traditional ROI: 5.01%
1011 N 14th Avenue Winterset, IA Discover your own slice of heaven right in town! This inviting two-story home is set in a ...	4 beds \| 4 baths \| 2,460 sq.ft.	$404,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.73% Airbnb Rental Income: $null Traditional Rental Income: $3268 Airbnb ROI: N/A Traditional ROI: 5.73%
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.	$450,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 4.93% Airbnb Rental Income: $1941 Traditional Rental Income: $3144 Airbnb ROI: 0.85% Traditional ROI: 4.93%
609 E Filmore Street Winterset, IA Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR'...	4 beds \| 2 baths \| 1,104 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.17%
721 W Court Avenue Winterset, IA Don't miss the opportunity to own this home on historical Court Avenue! You will love sitt...	3 beds \| 2 baths \| 2,130 sq.ft.	$309,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.72% Airbnb Rental Income: $1941 Traditional Rental Income: $2492 Airbnb ROI: 2.07% Traditional ROI: 5.72%
204 W Washington Street Winterset, IA If you're looking for WOW this. is. IT!! This stunning 1875 two story has been well ...	5 beds \| 4 baths \| 3,520 sq.ft.	$440,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 6.04% Airbnb Rental Income: $1553 Traditional Rental Income: $3837 Airbnb ROI: -0.59% Traditional ROI: 6.04%
1221 W Washington Street Winterset, IA This super sweet ranch home makes a great starter home. The covered front porch is a great...	2 beds \| 1 baths \| 816 sq.ft.	$230,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.65% Airbnb Rental Income: $1209 Traditional Rental Income: $1421 Airbnb ROI: 0.88% Traditional ROI: 3.65%
501 W Hutchings Street Winterset, IA Welcome to this beautiful home in the heart of Winterset. This property features 3-beds, 1...	3 beds \| 2 baths \| 988 sq.ft.	$200,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 6.55% Airbnb Rental Income: $1941 Traditional Rental Income: $1846 Airbnb ROI: 4.35% Traditional ROI: 6.55%
303 E Court Avenue Winterset, IA Welcome to one of the charming historical homes in Winterset. Walking through the front en...	3 beds \| 2 baths \| 1,725 sq.ft.	$269,400	Airbnb cash on cash: 2.84% Traditional cash on cash: 6.51% Airbnb Rental Income: $1941 Traditional Rental Income: $2363 Airbnb ROI: 2.84% Traditional ROI: 6.51%
59 E Benton Street Winterset, IA Step inside this well-loved home that blends timeless character with modern updates-ready ...	4 beds \| 2 baths \| 1,912 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $2689 Airbnb ROI: N/A Traditional ROI: 6.3%
66 E High Street Winterset, IA Imagine starting your mornings in a sunlit living room, coffee in hand, as the quiet charm...	3 beds \| 2 baths \| 1,452 sq.ft.	$199,900	Airbnb cash on cash: 4.4% Traditional cash on cash: 5.44% Airbnb Rental Income: $1941 Traditional Rental Income: $1625 Airbnb ROI: 4.4% Traditional ROI: 5.44%
316 E Jefferson Street Winterset, IA Charming Victorian that has been fully renovated. The living room has ten-foot ceilings, b...	3 beds \| 2 baths \| 1,106 sq.ft.	$245,400	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.07% Airbnb Rental Income: $1941 Traditional Rental Income: $1637 Airbnb ROI: 3.17% Traditional ROI: 4.07%
2160 114th Court Winterset, IA Amazing New Construction acreage! Picturesque views await in this fantastic home at Scenic...	5 beds \| 5 baths \| 3,111 sq.ft.	$1,079,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 1.84% Airbnb Rental Income: $1553 Traditional Rental Income: $4545 Airbnb ROI: -1.59% Traditional ROI: 1.84%
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.	$220,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 6.87% Airbnb Rental Income: $1209 Traditional Rental Income: $2110 Airbnb ROI: 0.67% Traditional ROI: 6.87%
513 W Hutchings Street Winterset, IA Step into this beautifully remodeled 2025 home complete with 3 bedrooms and 1.5 bathrooms....	3 beds \| 2 baths \| 958 sq.ft.	$226,900	Airbnb cash on cash: 4.69% Traditional cash on cash: 5.9% Airbnb Rental Income: $1941 Traditional Rental Income: $1688 Airbnb ROI: 4.69% Traditional ROI: 5.9%
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.	$220,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 5.77% Airbnb Rental Income: $1209 Traditional Rental Income: $1881 Airbnb ROI: 0.67% Traditional ROI: 5.77%
513 E Jefferson Street Winterset, IA Motivated sellers! Welcome to this huge 3 bed, 3 bath home with a great, beautiful lot in ...	3 beds \| 3 baths \| 1,776 sq.ft.	$279,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 7.69% Airbnb Rental Income: $1941 Traditional Rental Income: $2500 Airbnb ROI: 3.61% Traditional ROI: 7.69%
1634 170th Street Winterset, IA Scenic Winterset Acreage - Earlham Schools - Ranch Home on 11+ Acres with Walkout Basement...	4 beds \| 3 baths \| 1,895 sq.ft.	$662,499	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $2822 Airbnb ROI: N/A Traditional ROI: 2.74%
1694 McBride Ridge Court Winterset, IA Acreage for sale in Winterset Iowa! Discover your own slice of country paradise just 100 y...	4 beds \| 3 baths \| 1,878 sq.ft.	$599,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $2673 Airbnb ROI: N/A Traditional ROI: 2.52%
2218 N John Wayne Drive Winterset, IA Welcome to this exceptional 3300 sq ft 3/4-bedroom, 4-bath brick ranch that perfectly bala...	3 beds \| 4 baths \| 3,298 sq.ft.	$675,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 2.08% Airbnb Rental Income: $1941 Traditional Rental Income: $3382 Airbnb ROI: -1.02% Traditional ROI: 2.08%
812 N 8th Avenue Winterset, IA Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort a...	5 beds \| 3 baths \| 2,137 sq.ft.	$449,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 4.21% Airbnb Rental Income: $1553 Traditional Rental Income: $2945 Airbnb ROI: -0.15% Traditional ROI: 4.21%
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.	$249,900	Airbnb cash on cash: 3.84% Traditional cash on cash: 4.6% Airbnb Rental Income: $1941 Traditional Rental Income: $1609 Airbnb ROI: 3.84% Traditional ROI: 4.6%
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.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $2701 Airbnb ROI: N/A Traditional ROI: 4.89%
719 E Washington Street Winterset, IA If the "Wow Factor" is what you are hoping for in a home, this one is a must-see! This hom...	3 beds \| 3 baths \| 2,432 sq.ft.	$650,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.64% Airbnb Rental Income: $1941 Traditional Rental Income: $2936 Airbnb ROI: 0.16% Traditional ROI: 2.64%
215 W Buchanan Street Winterset, IA Better than new, this fully renovated Winterset home is truly move in ready. This 4-bedroo...	4 beds \| 3 baths \| 1,333 sq.ft.	$354,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2373 Airbnb ROI: N/A Traditional ROI: 5.22%
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: -0.53% Traditional cash on cash: 3.12% Airbnb Rental Income: $1553 Traditional Rental Income: $3253 Airbnb ROI: -0.53% 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.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $2539 Airbnb ROI: N/A Traditional ROI: 2.95%
110 E Grade Street Winterset, IA Step into this beautifully remodeled and charming single-story home, thoughtfully designed...	3 beds \| 2 baths \| 1,174 sq.ft.	$225,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 6.97% Airbnb Rental Income: $1941 Traditional Rental Income: $1957 Airbnb ROI: 4.49% Traditional ROI: 6.97%
207 E Buchanan Street Winterset, IA Discover this inviting frame home located near the Winterset Square. The main level featur...	3 beds \| 2 baths \| 1,246 sq.ft.	$142,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 11.46% Airbnb Rental Income: $1941 Traditional Rental Income: $2018 Airbnb ROI: 7.13% Traditional ROI: 11.46%
827 W Fremont Street Winterset, IA Just listed . . . . townhome in the West End Townhomes located off W Fremont Street in Win...	2 beds \| 3 baths \| 1,213 sq.ft.	$212,500	Airbnb cash on cash: 1.21% Traditional cash on cash: 7.29% Airbnb Rental Income: $1209 Traditional Rental Income: $2043 Airbnb ROI: 1.21% Traditional ROI: 7.29%
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: 5.79% Traditional cash on cash: 8.4% Airbnb Rental Income: $1941 Traditional Rental Income: $1849 Airbnb ROI: 5.79% 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.	$375,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.66% Airbnb Rental Income: $1941 Traditional Rental Income: $2626 Airbnb ROI: 1.26% Traditional ROI: 4.66%
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.	$220,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 6.02% Airbnb Rental Income: $1209 Traditional Rental Income: $1878 Airbnb ROI: 0.94% Traditional ROI: 6.02%
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.	$216,000	Airbnb cash on cash: 1% Traditional cash on cash: 6.17% Airbnb Rental Income: $1209 Traditional Rental Income: $1878 Airbnb ROI: 1% Traditional ROI: 6.17%
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.	$320,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 3.86% Airbnb Rental Income: $1941 Traditional Rental Income: $2011 Airbnb ROI: 1.93% Traditional ROI: 3.86%
2202 Ash Tree Drive Winterset, IA BETTER THAN NEW - Completed landscaping, fencing, window treatments & a long list of custo...	3 beds \| 3 baths \| 1,502 sq.ft.	$485,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.33% Airbnb Rental Income: $1941 Traditional Rental Income: $2547 Airbnb ROI: 1.87% Traditional ROI: 4.33%
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.	$599,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 1.63% Airbnb Rental Income: $1941 Traditional Rental Income: $1862 Airbnb ROI: 0.85% Traditional ROI: 1.63%
Lot 27 114th Ct Winterset, IA Lot 27 114th Ct, Winterset, IA 50273 \| Other	N/A beds \| N/A baths \| N/A	$170,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 1.68% Airbnb Rental Income: $631 Traditional Rental Income: $777 Airbnb ROI: -1.03% Traditional ROI: 1.68%
Lot 26 114th Ct Winterset, IA Lot 26 114th Ct, Winterset, IA 50273 \| Other	N/A beds \| N/A baths \| N/A	$215,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.81% Airbnb Rental Income: $631 Traditional Rental Income: $777 Airbnb ROI: -1.35% Traditional ROI: 0.81%
Lot 16 114th Ct Winterset, IA Lot 16 114th Ct, Winterset, IA 50273 \| Other	N/A beds \| N/A baths \| N/A	$240,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 1.62% Airbnb Rental Income: $631 Traditional Rental Income: $1038 Airbnb ROI: -1.47% Traditional ROI: 1.62%

Real Estate investment in Winterset, IA

There are 62 properties for sale in the city of Winterset . The median list price in Winterset is $254,500 and the average price per square foot is $144. In January 2026, the average monthly cash on cash return in Winterset is 5.00%. The average monthly rental income in Winterset is $1,986.

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

There are 62 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 $1,986.

Your search for investment property begins and ends here

Investment Property for Sale in Winterset, IA

410 N 6th Street

Winterset, IA

3 beds | 2 baths | 1,400 sq.ft.

$290,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $1941

Traditional Rental Income: $2156

Airbnb ROI: 2.34%

Traditional ROI: 5.01%

1011 N 14th Avenue

Winterset, IA

4 beds | 4 baths | 2,460 sq.ft.

$404,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3268

Airbnb ROI: N/A

Traditional ROI: 5.73%

1913 N 1st Street

Winterset, IA

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

$450,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $1941

Traditional Rental Income: $3144

Airbnb ROI: 0.85%

Traditional ROI: 4.93%

609 E Filmore Street

Winterset, IA

4 beds | 2 baths | 1,104 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.17%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.17%

721 W Court Avenue

Winterset, IA

3 beds | 2 baths | 2,130 sq.ft.

$309,900

Airbnb cash on cash: 2.07%

Traditional cash on cash: 5.72%

Airbnb Rental Income: $1941

Traditional Rental Income: $2492

Airbnb ROI: 2.07%

Traditional ROI: 5.72%

204 W Washington Street

Winterset, IA

5 beds | 4 baths | 3,520 sq.ft.

$440,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1553

Traditional Rental Income: $3837

Airbnb ROI: -0.59%

Traditional ROI: 6.04%

1221 W Washington Street

Winterset, IA

2 beds | 1 baths | 816 sq.ft.

$230,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $1209

Traditional Rental Income: $1421

Airbnb ROI: 0.88%

Traditional ROI: 3.65%

501 W Hutchings Street

Winterset, IA

3 beds | 2 baths | 988 sq.ft.

$200,000

Airbnb cash on cash: 4.35%

Traditional cash on cash: 6.55%

Airbnb Rental Income: $1941

Traditional Rental Income: $1846

Airbnb ROI: 4.35%