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.	$295,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 4.91% Airbnb Rental Income: $2139 Traditional Rental Income: $2156 Airbnb ROI: 2.88% Traditional ROI: 4.91%
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%
323 W Jefferson Street Winterset, IA Exquisite historic home in the heart of Winterset just blocks from the bustling downtown s...	5 beds \| 3 baths \| 2,968 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $3074 Airbnb ROI: N/A Traditional ROI: 6.37%
620 W Filmore Street Winterset, IA Available now for quick possesion!! Charming Ranch with modern Updates on a Quiet Stre...	3 beds \| 2 baths \| 1,741 sq.ft.	$287,500	Airbnb cash on cash: 3.1% Traditional cash on cash: 3.63% Airbnb Rental Income: $2139 Traditional Rental Income: $1737 Airbnb ROI: 3.1% Traditional ROI: 3.63%
418-422 N 6th Street Winterset, IA Investor Alert! Super clean and well-maintained duplex investment property. Each unit has ...	4 beds \| 1 baths \| 995 sq.ft.	$305,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 2.97% Airbnb Rental Income: $2139 Traditional Rental Income: $1708 Airbnb ROI: 2.57% Traditional ROI: 2.97%
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: 1.31% Traditional cash on cash: 4.99% Airbnb Rental Income: $2139 Traditional Rental Income: $3144 Airbnb ROI: 1.31% Traditional ROI: 4.99%
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: 6.57% Traditional cash on cash: 7.18% Airbnb Rental Income: $2139 Traditional Rental Income: $1696 Airbnb ROI: 6.57% 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.	$274,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 4.91%
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: 2.64% Traditional cash on cash: 5.72% Airbnb Rental Income: $2139 Traditional Rental Income: $2492 Airbnb ROI: 2.64% Traditional ROI: 5.72%
604 W Jefferson Street Winterset, IA This Gorgeous historical home is waiting for you on one of the prettiest streets in Winter...	3 beds \| 4 baths \| 1,694 sq.ft.	$308,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 7.08% Airbnb Rental Income: $2139 Traditional Rental Income: $2946 Airbnb ROI: 2.43% Traditional ROI: 7.08%
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.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.88% Airbnb Rental Income: $null Traditional Rental Income: $3837 Airbnb ROI: N/A Traditional ROI: 5.88%
520 W Benton Street Winterset, IA Charming 1.5 Story Home with Space for Everyone! This adorable 4-bedroom, 2-bath home offe...	4 beds \| 2 baths \| 1,451 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $2306 Airbnb ROI: N/A Traditional ROI: 6.94%
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.	$274,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 6.37% Airbnb Rental Income: $2139 Traditional Rental Income: $2363 Airbnb ROI: 3.4% Traditional ROI: 6.37%
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.	$217,400	Airbnb cash on cash: 4.78% Traditional cash on cash: 4.93% Airbnb Rental Income: $2139 Traditional Rental Income: $1625 Airbnb ROI: 4.78% Traditional ROI: 4.93%
822 N 3rd Avenue Winterset, IA Well maintained townhome on quiet cul-de-sac street. Large open concept living room, 2-bed...	2 beds \| 2 baths \| 1,406 sq.ft.	$269,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.85% Airbnb Rental Income: $1246 Traditional Rental Income: $2041 Airbnb ROI: 0.15% Traditional ROI: 4.85%
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.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.98% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 5.98%
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.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $1622 Airbnb ROI: N/A Traditional ROI: 6.87%
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.	$247,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 4.02% Airbnb Rental Income: $2139 Traditional Rental Income: $1637 Airbnb ROI: 3.83% Traditional ROI: 4.02%
520 W Madison Street Winterset, IA Charming 2BR/1BA Townhome with Attached Garage in the Heart of Madison County! This inviti...	2 beds \| 1 baths \| 1,030 sq.ft.	$209,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.15% Airbnb Rental Income: $1246 Traditional Rental Income: $1347 Airbnb ROI: 1.64% Traditional ROI: 4.15%
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.	$1,170,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $4545 Airbnb ROI: N/A Traditional ROI: 1.5%
423 E Jefferson Street Winterset, IA Classic 1920 Craftsman with all of the charm and character you'd expect. As you walk up to...	3 beds \| 2 baths \| 1,913 sq.ft.	$285,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 6.97% Airbnb Rental Income: $2139 Traditional Rental Income: $2560 Airbnb ROI: 3.37% Traditional ROI: 6.97%
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.	$159,900	Airbnb cash on cash: 7.48% Traditional cash on cash: 8.4% Airbnb Rental Income: $2139 Traditional Rental Income: $1734 Airbnb ROI: 7.48% Traditional ROI: 8.4%
204 Grade Street E Winterset, IA New Construction. Two story home with a cool layout. Home features three bedrooms, two and...	3 beds \| 3 baths \| 1,564 sq.ft.	$414,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.59% Airbnb Rental Income: $2139 Traditional Rental Income: $2286 Airbnb ROI: 2.81% Traditional ROI: 4.59%
413 Madison Street W 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: 0.88% Traditional cash on cash: 7.04% Airbnb Rental Income: $1246 Traditional Rental Income: $2110 Airbnb ROI: 0.88% Traditional ROI: 7.04%
411 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: 0.82% Traditional cash on cash: 6.87% Airbnb Rental Income: $1246 Traditional Rental Income: $2110 Airbnb ROI: 0.82% 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: 5.4% Traditional cash on cash: 5.84% Airbnb Rental Income: $2139 Traditional Rental Income: $1688 Airbnb ROI: 5.4% Traditional ROI: 5.84%
1220 W Court Avenue Winterset, IA Instantly appealing 1 1/2 story family home on Winterset W side with attached 2 car garage...	3 beds \| 2 baths \| 1,513 sq.ft.	$313,500	Airbnb cash on cash: 2.54% Traditional cash on cash: 4.72% Airbnb Rental Income: $2139 Traditional Rental Income: $2235 Airbnb ROI: 2.54% Traditional ROI: 4.72%
304 Maple Point Winterset, IA Stryker Ranch with over-sized 3 car garage. Front porch with 2 stone base posts. 9'ceiling...	3 beds \| 2 baths \| 1,400 sq.ft.	$384,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 5% Airbnb Rental Income: $2139 Traditional Rental Income: $2305 Airbnb ROI: 3.03% Traditional ROI: 5%
408 E Benton Street Winterset, IA Charming & Updated in Winterset! This adorable home is move-in ready with tons of recent u...	2 beds \| 1 baths \| 768 sq.ft.	$164,500	Airbnb cash on cash: 2.54% Traditional cash on cash: 6.44% Airbnb Rental Income: $1246 Traditional Rental Income: $1461 Airbnb ROI: 2.54% Traditional ROI: 6.44%
2369 Saint Charles Road Winterset, IA MADISON COUNTY ACREAGE! Beautiful ZERO ENTRY home, that was built with CONCRETE WALLS, on ...	3 beds \| 2 baths \| 1,650 sq.ft.	$440,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 3.47% Airbnb Rental Income: $2139 Traditional Rental Income: $2206 Airbnb ROI: 1.98% Traditional ROI: 3.47%
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.	$330,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 6.33% Airbnb Rental Income: $2139 Traditional Rental Income: $2895 Airbnb ROI: 2.13% Traditional ROI: 6.33%
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.	$667,499	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $2822 Airbnb ROI: N/A Traditional ROI: 2.72%
715 N John Wayne Drive Winterset, IA Super unique investment opportunity! This property consists of a residential house and 4 r...	4 beds \| 3 baths \| 1,728 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $2458 Airbnb ROI: N/A Traditional ROI: 2.46%
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%
59 Washington Street E Winterset, IA Great opportunity for an investor or a first-time buyer looking to make a place their own!...	2 beds \| 1 baths \| 942 sq.ft.	$124,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 9.37% Airbnb Rental Income: $1246 Traditional Rental Income: $1459 Airbnb ROI: 4.27% Traditional ROI: 9.37%
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.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.3% Airbnb Rental Income: $null Traditional Rental Income: $2673 Airbnb ROI: N/A Traditional ROI: 2.3%
2385 Holliwell Bridge Road Winterset, IA Welcome to your dream country retreat! Nestled on 3.17 acres, this beautifully updated 1.5...	3 beds \| 1 baths \| 1,350 sq.ft.	$314,999	Airbnb cash on cash: 3.32% Traditional cash on cash: 4.21% Airbnb Rental Income: $2139 Traditional Rental Income: $1858 Airbnb ROI: 3.32% Traditional ROI: 4.21%
522 N 10th Street Winterset, IA Double Lot Opportunity! So Much Potential!! Don't miss out on this spacious 3+ bedroom, 2-...	3 beds \| 3 baths \| 1,972 sq.ft.	$310,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 6.47% Airbnb Rental Income: $2139 Traditional Rental Income: $2741 Airbnb ROI: 2.53% Traditional ROI: 6.47%
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%

Real Estate investment in Winterset, IA

There are 57 properties for sale in the city of Winterset . The median list price in Winterset is $311,750 and the average price per square foot is $184. In September 2025, the average monthly cash on cash return in Winterset is 5.00%. The average monthly rental income in Winterset is $2,335.

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

There are 57 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 $2,335.

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.

$295,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $2139

Traditional Rental Income: $2156

Airbnb ROI: 2.88%

Traditional ROI: 4.91%

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%

323 W Jefferson Street

Winterset, IA

5 beds | 3 baths | 2,968 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.37%

Airbnb Rental Income: $null

Traditional Rental Income: $3074

Airbnb ROI: N/A

Traditional ROI: 6.37%

620 W Filmore Street

Winterset, IA

3 beds | 2 baths | 1,741 sq.ft.

$287,500

Airbnb cash on cash: 3.1%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $2139

Traditional Rental Income: $1737

Airbnb ROI: 3.1%

Traditional ROI: 3.63%

418-422 N 6th Street

Winterset, IA

4 beds | 1 baths | 995 sq.ft.

$305,000

Airbnb cash on cash: 2.57%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $2139

Traditional Rental Income: $1708

Airbnb ROI: 2.57%

Traditional ROI: 2.97%

1913 N 1st Street

Winterset, IA

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

$450,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $2139

Traditional Rental Income: $3144

Airbnb ROI: 1.31%

Traditional ROI: 4.99%

601 E Green Street

Winterset, IA

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

$177,000

Airbnb cash on cash: 6.57%

Traditional cash on cash: 7.18%

Airbnb Rental Income: $2139

Traditional Rental Income: $1696

Airbnb ROI: 6.57%

Traditional ROI: 7.18%

609 E Filmore Street

Winterset, IA

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

$274,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A