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
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.	$375,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 5.89% Airbnb Rental Income: $1555 Traditional Rental Income: $3144 Airbnb ROI: 0.1% Traditional ROI: 5.89%
715 N 5th Street Winterset, IA SELLER IS OFFERING A 3-YEAR HOME WARRANTY! Welcome home to 715 N 5th Street! Nestled on th...	3 beds \| 2 baths \| 1,456 sq.ft.	$177,500	Airbnb cash on cash: 3.87% Traditional cash on cash: 10.23% Airbnb Rental Income: $1555 Traditional Rental Income: $2181 Airbnb ROI: 3.87% Traditional ROI: 10.23%
121 E Benton Street Winterset, IA If you are looking for a starter home or a nice home to downsize, you need to take a look ...	2 beds \| 1 baths \| 848 sq.ft.	$208,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 5.16% Airbnb Rental Income: $1237 Traditional Rental Income: $1537 Airbnb ROI: 1.64% Traditional ROI: 5.16%
1405 W Jefferson Street Winterset, IA Welcome to this well-maintained 4 bedroom, 3 bathroom home offering just under 1,500 squar...	4 beds \| 3 baths \| 1,470 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $2179 Airbnb ROI: N/A Traditional ROI: 4.48%
306 E Buchanan Street Winterset, IA Well kept and adorable 2 bed 1 bath ranch home. You will love the character in this sweet ...	2 beds \| 1 baths \| 986 sq.ft.	$205,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $1237 Traditional Rental Income: $1081 Airbnb ROI: 1.49% Traditional ROI: 2.72%
305 Magnolia Point Winterset, IA Beat the market rates! Sellers offering a 2-1 buydown to drop your interest rate by 2% in ...	4 beds \| 4 baths \| 1,807 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.04% Airbnb Rental Income: $null Traditional Rental Income: $2142 Airbnb ROI: N/A Traditional ROI: 2.04%
602 N 1st Avenue Winterset, IA Step into the timeless charm of this spacious Victorian home, perfectly situated on a corn...	4 beds \| 3 baths \| 2,146 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $2057 Airbnb ROI: N/A Traditional ROI: 5.33%
612 W Jefferson Street Winterset, IA Introducing a soaring piece of Winterset architectual history in this 1905 Colonial two st...	3 beds \| 2 baths \| 1,976 sq.ft.	$290,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.41% Airbnb Rental Income: $1555 Traditional Rental Income: $1539 Airbnb ROI: 0.82% Traditional ROI: 2.41%
423 E Jefferson Street Winterset, IA ****Seller has taken a new job with a long commute. They are motivated to sell before wint...	3 beds \| 2 baths \| 1,913 sq.ft.	$299,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 6.27% Airbnb Rental Income: $1555 Traditional Rental Income: $2560 Airbnb ROI: 1.12% Traditional ROI: 6.27%
1018 N 3rd Avenue Winterset, IA PRICE REDUCED This well-maintained townhome is in the perfect location on the end of a...	2 beds \| 2 baths \| 1,426 sq.ft.	$289,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 2.79% Airbnb Rental Income: $1555 Traditional Rental Income: $1611 Airbnb ROI: 0.94% Traditional ROI: 2.79%
801 S 3rd Street Winterset, IA Enjoy the best of both worlds with this beautiful new construction home on an established ...	3 beds \| 2 baths \| 1,459 sq.ft.	$425,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 3.98% Airbnb Rental Income: $1555 Traditional Rental Income: $2095 Airbnb ROI: 1.5% Traditional ROI: 3.98%
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.	$249,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.67% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 7.67%
615 N 1st Avenue Winterset, IA STEP INTO HISTORY in Winterset! Preservationists will appreciate this lovingly cared-for 1...	4 beds \| 3 baths \| 2,724 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.69% Airbnb Rental Income: $null Traditional Rental Income: $2701 Airbnb ROI: N/A Traditional ROI: 5.69%
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: 3.87% Traditional cash on cash: 8.48% Airbnb Rental Income: $1555 Traditional Rental Income: $1849 Airbnb ROI: 3.87% Traditional ROI: 8.48%
310 W Washington Street Winterset, IA A truely unique and well kept historic home is ready for new owners. The character is abun...	4 beds \| 2 baths \| 2,430 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 5% Airbnb Rental Income: $null Traditional Rental Income: $2626 Airbnb ROI: N/A Traditional ROI: 5%
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: 1.21% Traditional cash on cash: 6.42% Airbnb Rental Income: $1237 Traditional Rental Income: $1878 Airbnb ROI: 1.21% 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: 1.29% Traditional cash on cash: 6.59% Airbnb Rental Income: $1237 Traditional Rental Income: $1878 Airbnb ROI: 1.29% Traditional ROI: 6.59%
302 W Court Avenue Winterset, IA Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideall...	3 beds \| 3 baths \| 2,396 sq.ft.	$365,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 5.59% Airbnb Rental Income: $1555 Traditional Rental Income: $2820 Airbnb ROI: 0.59% Traditional ROI: 5.59%
2607 Quail Ridge Trail Winterset, IA Set on 3 peaceful acres in Madison County, this charming 1.5-story farmhouse offers the pe...	4 beds \| 2 baths \| 2,077 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.82% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 4.82%
511 W Washington Street Winterset, IA Welcoming 1 1/2 story brick home on Winterset West side. Recent remodel, galley kitchen, m...	4 beds \| 3 baths \| 1,540 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $2723 Airbnb ROI: N/A Traditional ROI: 6.44%
1509 State Highway 92 Winterset, IA Rare opportunity to create something truly special in the country! Tucked away on 3.82 sce...	4 beds \| 2 baths \| 1,680 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.32% Airbnb Rental Income: $null Traditional Rental Income: $1973 Airbnb ROI: N/A Traditional ROI: 5.32%
2318 Saint Charles Road Winterset, IA ? SELLER INCENTIVE - $15,000 OFFERED TO BUYER! ? Use it toward closing costs, a price redu...	3 beds \| 2 baths \| 1,982 sq.ft.	$885,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.47% Airbnb Rental Income: $1555 Traditional Rental Income: $2666 Airbnb ROI: -0.42% Traditional ROI: 1.47%
715 N 3rd Avenue Winterset, IA MOVE IN READY WITH ALL THE UPDATES This 4 bed 2 bath has been thoughtfully and skill...	4 beds \| 2 baths \| 866 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.7% Airbnb Rental Income: $null Traditional Rental Income: $1933 Airbnb ROI: N/A Traditional ROI: 5.7%
420 W Mills Street Winterset, IA This well-maintained home offers a ton of space and a sprawling floor plan that sets it ap...	4 beds \| 3 baths \| 1,432 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.03% Airbnb Rental Income: $null Traditional Rental Income: $2328 Airbnb ROI: N/A Traditional ROI: 7.03%
5219 Cherrywood Lane Winterset, IA Stunning 4 bed (5 non-conforming) 3 bath home nestled on 2.24 acres! Walking in you are in...	4 beds \| 3 baths \| 1,506 sq.ft.	$559,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $2597 Airbnb ROI: N/A Traditional ROI: 2.28%
703 N 10th Avenue Winterset, IA Easy living in this spacious ranch home. You will love the covered front porch as you are ...	4 beds \| 3 baths \| 1,743 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 3.38%
1818 Patricia Acres Court Winterset, IA WELCOME HOME to this beautiful, CUSTOM-BUILT home on 2.1 private acres. Did I mention how ...	3 beds \| 3 baths \| 2,616 sq.ft.	$474,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 4.15% Airbnb Rental Income: $1555 Traditional Rental Income: $2917 Airbnb ROI: 0.07% Traditional ROI: 4.15%
1515 W Washington Street Winterset, IA Imagine a home where you don't have to compromise on a single detail. Welcome to 1515 W Wa...	3 beds \| 2 baths \| 2,484 sq.ft.	$440,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.33% Airbnb Rental Income: $1555 Traditional Rental Income: $2590 Airbnb ROI: -0.27% Traditional ROI: 3.33%
1582 N River Trail Winterset, IA A rare Madison County property where country living, history & opportunity come together o...	4 beds \| 3 baths \| 1,884 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.41% Airbnb Rental Income: $null Traditional Rental Income: $2890 Airbnb ROI: N/A Traditional ROI: 0.41%
703 Filmore Street E Winterset, IA Proudly sitting on a corner lot with many all-new features in 2026. It's a perfect blend o...	4 beds \| 1 baths \| 1,338 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.14% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 7.14%
2381 Highway 169 Winterset, IA This acreage has so much to offer! Located on pavement, just outside of Winterset, in beau...	4 beds \| 5 baths \| 3,076 sq.ft.	$924,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $4637 Airbnb ROI: N/A Traditional ROI: 3.36%
1624 S 4th Avenue Winterset, IA Thia 1.5 story home layout features two bedrooms and a bath on each floor. It is located j...	2 beds \| 2 baths \| 1,230 sq.ft.	$150,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 10.43% Airbnb Rental Income: $1237 Traditional Rental Income: $1879 Airbnb ROI: 3.2% Traditional ROI: 10.43%
2394 Cumming Road Winterset, IA Escape to your own private retreat on this magnificent 2.91-acre ranch estate, where moder...	3 beds \| 3 baths \| 1,724 sq.ft.	$775,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.51% Airbnb Rental Income: $1555 Traditional Rental Income: $2653 Airbnb ROI: -0.63% Traditional ROI: 1.51%
1986 Quarry Trail Winterset, IA Enjoy country living on 5.49 picturesque acres! This 4-bedroom, 2-bath home features a rem...	4 beds \| 2 baths \| 1,296 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $2152 Airbnb ROI: N/A Traditional ROI: 5.45%
1824 W Summit Street Winterset, IA Discover your dream hobby farm with this rare in-town acreage offering 6.36 scenic acres o...	3 beds \| 1 baths \| 1,542 sq.ft.	$325,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.76% Airbnb Rental Income: $1555 Traditional Rental Income: $1840 Airbnb ROI: 1.36% Traditional ROI: 3.76%
317 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.	$402,500	Airbnb cash on cash: 1.59% Traditional cash on cash: 4.72% Airbnb Rental Income: $1555 Traditional Rental Income: $2289 Airbnb ROI: 1.59% Traditional ROI: 4.72%
228 Maple Point 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.	$405,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 4.7% Airbnb Rental Income: $1555 Traditional Rental Income: $2294 Airbnb ROI: 1.57% Traditional ROI: 4.7%
510 E South Street Winterset, IA WELCOME HOME! As soon as you drive up, you will notice the huge, PARK LIKE YARD that you c...	3 beds \| 1 baths \| 1,258 sq.ft.	$234,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 5.39% Airbnb Rental Income: $1555 Traditional Rental Income: $1830 Airbnb ROI: 2.14% Traditional ROI: 5.39%
423 S 3rd Street Winterset, IA Welcome to 423 S 3rd Street, where small-town charm meets everyday convenience in the hear...	2 beds \| 1 baths \| 1,080 sq.ft.	$205,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 5.42% Airbnb Rental Income: $1237 Traditional Rental Income: $1609 Airbnb ROI: 1.47% Traditional ROI: 5.42%
1215 State Highway 92 Winterset, IA A great opportunity to own your own hobby farm, horse property or add to your portfolio. 5...	4 beds \| 2 baths \| 1,400 sq.ft.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2259 Airbnb ROI: N/A Traditional ROI: 1.63%

Real Estate investment in Winterset, IA

There are 41 properties for sale in the city of Winterset . The median list price in Winterset is $279,867 and the average price per square foot is $175. In November 2026, the average monthly cash on cash return in Winterset is 5.00%. The average monthly rental income in Winterset is $2,157.

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

There are 41 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 $2,157.

Your search for investment property begins and ends here

Investment Property for Sale in Winterset, IA

1913 N 1st Street

Winterset, IA

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

$375,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $1555

Traditional Rental Income: $3144

Airbnb ROI: 0.1%

Traditional ROI: 5.89%

715 N 5th Street

Winterset, IA

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

$177,500

Airbnb cash on cash: 3.87%

Traditional cash on cash: 10.23%

Airbnb Rental Income: $1555

Traditional Rental Income: $2181

Airbnb ROI: 3.87%

Traditional ROI: 10.23%

121 E Benton Street

Winterset, IA

2 beds | 1 baths | 848 sq.ft.

$208,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1237

Traditional Rental Income: $1537

Airbnb ROI: 1.64%

Traditional ROI: 5.16%

1405 W Jefferson Street

Winterset, IA

4 beds | 3 baths | 1,470 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2179

Airbnb ROI: N/A

Traditional ROI: 4.48%

306 E Buchanan Street

Winterset, IA

2 beds | 1 baths | 986 sq.ft.

$205,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1237

Traditional Rental Income: $1081

Airbnb ROI: 1.49%

Traditional ROI: 2.72%

305 Magnolia Point

Winterset, IA

4 beds | 4 baths | 1,807 sq.ft.

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2142

Airbnb ROI: N/A

Traditional ROI: 2.04%

602 N 1st Avenue

Winterset, IA

4 beds | 3 baths | 2,146 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2057

Airbnb ROI: N/A

Traditional ROI: 5.33%

612 W Jefferson Street

Winterset, IA

3 beds | 2 baths | 1,976 sq.ft.

$290,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $1555

Traditional Rental Income: $1539

Airbnb ROI: 0.82%