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.

Single Family Homes for Sale in Winterset, IA

Search for Single Family Residential for Sale in Winterset, Iowa. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 44 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2156 Airbnb ROI: N/A 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.	$277,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $1737 Airbnb ROI: N/A Traditional ROI: 3.79%
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: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $3144 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 7.18% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A 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: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 4.84%
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: N/A Traditional cash on cash: 5.72% Airbnb Rental Income: $null Traditional Rental Income: $2492 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $3837 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $1846 Airbnb ROI: N/A 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.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A 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.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.14% Airbnb Rental Income: $null Traditional Rental Income: $1625 Airbnb ROI: N/A Traditional ROI: 5.14%
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.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 6.41%
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: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $1637 Airbnb ROI: N/A Traditional ROI: 4.02%
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: N/A Traditional cash on cash: 1.84% Airbnb Rental Income: $null Traditional Rental Income: $4545 Airbnb ROI: N/A Traditional ROI: 1.84%
315 S 5Th Avenue Winterset, IA Charming Brick Home with Bonus Space! This well-kept 2 bedroom, 2 bath brick home offers ...	2 beds \| 2 baths \| 1,120 sq.ft.	$210,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.82% Airbnb Rental Income: $1177 Traditional Rental Income: $1839 Airbnb ROI: 0.56% Traditional ROI: 5.82%
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: N/A Traditional cash on cash: 9.33% Airbnb Rental Income: $null Traditional Rental Income: $1734 Airbnb ROI: N/A Traditional ROI: 9.33%
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: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $2286 Airbnb ROI: N/A Traditional ROI: 4.59%
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: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $1688 Airbnb ROI: N/A Traditional ROI: 5.9%
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.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $2206 Airbnb ROI: N/A Traditional ROI: 3.91%
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: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $2895 Airbnb ROI: N/A 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.	$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%
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: 3.79% Traditional cash on cash: 9.37% Airbnb Rental Income: $1177 Traditional Rental Income: $1459 Airbnb ROI: 3.79% 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.	$624,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $2673 Airbnb ROI: N/A Traditional ROI: 2.38%
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%
701 W Buchanan Street Winterset, IA Easy living in this Ranch with many updates including roof, siding, gutters, furnace, a/c ...	3 beds \| 2 baths \| 1,823 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 6.9%
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.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $3382 Airbnb ROI: N/A Traditional ROI: 1.97%
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.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $2945 Airbnb ROI: N/A Traditional ROI: 4%
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: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2936 Airbnb ROI: N/A Traditional ROI: 2.64%
215 W Buchanan Street Winterset, IA Completely Renovated Winterset Gem! This 4-bedroom, 3-bath home (1,333 sq ft above grade +...	4 beds \| 3 baths \| 1,333 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2373 Airbnb ROI: N/A Traditional ROI: 4.9%
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: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $2296 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $3253 Airbnb ROI: N/A Traditional ROI: 3.12%
722 W Mills Street Winterset, IA Beautifully maintained 3-bedroom, 2-bath ranch showcasing an inviting open floor plan with...	3 beds \| 2 baths \| 1,252 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $2077 Airbnb ROI: N/A Traditional ROI: 4.57%
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: N/A Traditional cash on cash: 6.07% Airbnb Rental Income: $null Traditional Rental Income: $3066 Airbnb ROI: N/A Traditional ROI: 6.07%

Your search for investment property begins and ends here

Single Family Homes 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: N/A

Traditional cash on cash: 4.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2156

Airbnb ROI: N/A

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.

$277,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.79%

Airbnb Rental Income: $null

Traditional Rental Income: $1737

Airbnb ROI: N/A

Traditional ROI: 3.79%

1913 N 1st Street

Winterset, IA

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

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.93%

Airbnb Rental Income: $null

Traditional Rental Income: $3144

Airbnb ROI: N/A

Traditional ROI: 4.93%

601 E Green Street

Winterset, IA

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

$177,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.18%

Airbnb Rental Income: $null

Traditional Rental Income: $1696

Airbnb ROI: N/A

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: 4.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 4.84%

721 W Court Avenue

Winterset, IA

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

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2492

Airbnb ROI: N/A