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
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%
1541 Nature Court Winterset, IA Endless possibilities on nearly 5 acres of peaceful countryside! This 3-bedroom, 2-bath ma...	3 beds \| 2 baths \| 1,456 sq.ft.	$320,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 5.27% Airbnb Rental Income: $1941 Traditional Rental Income: $2144 Airbnb ROI: 2.89% Traditional ROI: 5.27%
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%
601 E Green Street Winterset, IA This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft ...	3 beds \| 1 baths \| 1,222 sq.ft.	$177,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 7.18% Airbnb Rental Income: $1941 Traditional Rental Income: $1696 Airbnb ROI: 5.59% Traditional ROI: 7.18%
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.	$264,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.06%
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%
2176 148th Street Winterset, IA Discover 17.9 Acres of Updated Country Living. Welcome to your dream acreage! This beautif...	4 beds \| 3 baths \| 1,534 sq.ft.	$924,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.47% Airbnb Rental Income: $null Traditional Rental Income: $2799 Airbnb ROI: N/A Traditional ROI: 1.47%
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.	$215,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 6.04% Airbnb Rental Income: $1941 Traditional Rental Income: $1846 Airbnb ROI: 3.99% Traditional ROI: 6.04%
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.	$272,400	Airbnb cash on cash: 2.79% Traditional cash on cash: 6.43% Airbnb Rental Income: $1941 Traditional Rental Income: $2363 Airbnb ROI: 2.79% Traditional ROI: 6.43%
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 Charming and fully updated 1.5 story home on a large corner lot in historic Winterset--rou...	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%
1413 W Washington Street Winterset, IA Move-in ready and beautifully maintained, this 4-bedroom ranch offers easy single-level li...	4 beds \| 2 baths \| 1,270 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 6.87%
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.	$140,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.59% Airbnb Rental Income: $null Traditional Rental Income: $1622 Airbnb ROI: N/A Traditional ROI: 8.59%
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%
516 W Summit Street Winterset, IA Are you looking for a house with a LARGE YARD, close to SCHOOLS and WINTERSET TOWN SQUARE....	3 beds \| 1 baths \| 1,200 sq.ft.	$145,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 9.33% Airbnb Rental Income: $1941 Traditional Rental Income: $1734 Airbnb ROI: 7.13% Traditional ROI: 9.33%
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%
724 W Jefferson Street Winterset, IA Prepare to be impressed with the renovations done to bring this stately home back to it's ...	3 beds \| 3 baths \| 2,436 sq.ft.	$315,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 6.67% Airbnb Rental Income: $1941 Traditional Rental Income: $2895 Airbnb ROI: 1.72% Traditional ROI: 6.67%
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%
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.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $2882 Airbnb ROI: N/A Traditional ROI: 6.71%
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%
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.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.27% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 6.27%
1821 Millstream Court Winterset, IA Prepare to be taken back by this distinguished two-story residence. With over 3700 finishe...	4 beds \| 4 baths \| 2,200 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $2868 Airbnb ROI: N/A Traditional ROI: 2.2%
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%
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 Completely Renovated Winterset Gem - Modern Style Meets Small-Town Charm! This 4-bedroom, ...	4 beds \| 3 baths \| 1,333 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.97% Airbnb Rental Income: $null Traditional Rental Income: $2373 Airbnb ROI: N/A Traditional ROI: 4.97%
225 Maple Point Winterset, IA Jackson Ranch Plan with over-sized 3 car garage. Front porch with 2 stone base posts. 9'ce...	3 beds \| 2 baths \| 1,400 sq.ft.	$386,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.03% Airbnb Rental Income: $1941 Traditional Rental Income: $2296 Airbnb ROI: 2.63% Traditional ROI: 5.03%
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: -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%
309 N 15th Avenue Winterset, IA Don't miss your chance to own this beautifully appointed 2-story home tucked away on a qui...	5 beds \| 4 baths \| 2,110 sq.ft.	$360,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 6.07% Airbnb Rental Income: $1553 Traditional Rental Income: $3066 Airbnb ROI: 0.27% Traditional ROI: 6.07%
1890 Hogback Bridge Road Winterset, IA Rare 30-acre M/L retreat in Madison County Iowa with a 4,000+ sq. ft. custom home. Incredi...	5 beds \| 5 baths \| 4,032 sq.ft.	$1,385,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.55% Airbnb Rental Income: $1553 Traditional Rental Income: $5392 Airbnb ROI: -0.78% Traditional ROI: 2.55%
120 S 8th Avenue Winterset, IA Opportunity knocks on this ready-to-renovate 3-bed 2 and 1/2 bath ranch home. This has one...	3 beds \| 3 baths \| 1,560 sq.ft.	$260,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 7.15% Airbnb Rental Income: $1941 Traditional Rental Income: $2500 Airbnb ROI: 2.79% Traditional ROI: 7.15%
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.	$145,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 11.21% Airbnb Rental Income: $1941 Traditional Rental Income: $2018 Airbnb ROI: 6.96% Traditional ROI: 11.21%
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.	$215,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 7.19% Airbnb Rental Income: $1209 Traditional Rental Income: $2043 Airbnb ROI: 1.18% Traditional ROI: 7.19%

Real Estate investment in Winterset, IA

There are 49 properties for sale in the city of Winterset . The median list price in Winterset is $317,500 and the average price per square foot is $178. In December 2025, the average monthly cash on cash return in Winterset is 6.00%. The average monthly rental income in Winterset is $2,433.

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

There are 49 investment properties available for sale in Winterset.

In 2025, 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 $2,433.

Your search for investment property begins and ends here

Investment Property for Sale in Winterset, IA

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%

1541 Nature Court

Winterset, IA

3 beds | 2 baths | 1,456 sq.ft.

$320,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $1941

Traditional Rental Income: $2144

Airbnb ROI: 2.89%

Traditional ROI: 5.27%

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%

601 E Green Street

Winterset, IA

3 beds | 1 baths | 1,222 sq.ft.

$177,000

Airbnb cash on cash: 5.59%

Traditional cash on cash: 7.18%

Airbnb Rental Income: $1941

Traditional Rental Income: $1696

Airbnb ROI: 5.59%

Traditional ROI: 7.18%

609 E Filmore Street

Winterset, IA

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

$264,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.06%

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%

2176 148th Street

Winterset, IA

4 beds | 3 baths | 1,534 sq.ft.

$924,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2799

Airbnb ROI: N/A