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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winterset, IA

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

Showing 50 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
623 W Green Street Winterset, IA Charming, solid, and beautifully cared for -this all-brick ranch in historic Madison Count...	4 beds \| 3 baths \| 1,464 sq.ft.	$309,990	Airbnb cash on cash: N/A Traditional cash on cash: 5.34% Airbnb Rental Income: $null Traditional Rental Income: $2346 Airbnb ROI: N/A Traditional ROI: 5.34%
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%
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.	$339,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 6.48% Airbnb Rental Income: $1553 Traditional Rental Income: $3074 Airbnb ROI: 0.3% Traditional ROI: 6.48%
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.	$440,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 5.06% Airbnb Rental Income: $1941 Traditional Rental Income: $3144 Airbnb ROI: 0.9% Traditional ROI: 5.06%
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%
901 E Buchanan Street Winterset, IA Completely remodeled from top to bottom, this move-in ready home blends modern finishes wi...	4 beds \| 2 baths \| 1,323 sq.ft.	$264,990	Airbnb cash on cash: N/A Traditional cash on cash: 5.51% Airbnb Rental Income: $null Traditional Rental Income: $2056 Airbnb ROI: N/A Traditional ROI: 5.51%
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.	$254,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.29%
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%
802 N 10th Avenue Winterset, IA Easy living in this open floor plan ranch home. A large covered front porch greets you as ...	4 beds \| 3 baths \| 1,555 sq.ft.	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2557 Airbnb ROI: N/A Traditional ROI: 3.16%
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.	$223,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 3.79% Airbnb Rental Income: $1209 Traditional Rental Income: $1421 Airbnb ROI: 0.94% Traditional ROI: 3.79%
619 N 10th Street Winterset, IA Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006...	3 beds \| 2 baths \| 1,095 sq.ft.	$230,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.45% Airbnb Rental Income: $1941 Traditional Rental Income: $1803 Airbnb ROI: 3.73% Traditional ROI: 5.45%
604 E Jefferson Street Winterset, IA Story and 1/2, 3BR 1.5 bath affordable home located in Winterset. Large eat-in kitchen, hu...	3 beds \| 2 baths \| 1,306 sq.ft.	$169,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 8.39% Airbnb Rental Income: $1941 Traditional Rental Income: $1837 Airbnb ROI: 5.87% Traditional ROI: 8.39%
415 E Buchanan Street Winterset, IA Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1...	2 beds \| 1 baths \| 1,286 sq.ft.	$165,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 8.06% Airbnb Rental Income: $1209 Traditional Rental Income: $1600 Airbnb ROI: 3.09% Traditional ROI: 8.06%
114 N 8th Avenue Winterset, IA Completely updated 3-bedroom, 2-bath home blending timeless character with extensive upgra...	3 beds \| 2 baths \| 1,545 sq.ft.	$245,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 7.34% Airbnb Rental Income: $1941 Traditional Rental Income: $2384 Airbnb ROI: 3.21% Traditional ROI: 7.34%
521 W Hutchings Street Winterset, IA Walk out ranch home with huge yard! This is a must see property! You will appreciate the u...	3 beds \| 2 baths \| 838 sq.ft.	$299,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.72% Airbnb Rental Income: $1941 Traditional Rental Income: $1554 Airbnb ROI: 2.28% Traditional ROI: 2.72%
710 N 3rd Avenue Winterset, IA Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home...	3 beds \| 1 baths \| 962 sq.ft.	$249,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 4.37% Airbnb Rental Income: $1941 Traditional Rental Income: $1592 Airbnb ROI: 3.67% Traditional ROI: 4.37%
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%
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.	$649,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $2822 Airbnb ROI: N/A Traditional ROI: 2.82%
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.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.36% Airbnb Rental Income: $null Traditional Rental Income: $2882 Airbnb ROI: N/A Traditional ROI: 7.36%
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%
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.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $2701 Airbnb ROI: N/A Traditional ROI: 5.05%
215 W Buchanan Street Winterset, IA Better than new, this fully renovated home offers 1,700+ total finished square feet and is...	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.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2539 Airbnb ROI: N/A Traditional ROI: 3.03%
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.	$205,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 7.58% Airbnb Rental Income: $1209 Traditional Rental Income: $2043 Airbnb ROI: 1.28% Traditional ROI: 7.58%
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.	$309,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 4.03% Airbnb Rental Income: $1941 Traditional Rental Income: $2011 Airbnb ROI: 2.03% Traditional ROI: 4.03%
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.	$449,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.5% Airbnb Rental Income: $1941 Traditional Rental Income: $1862 Airbnb ROI: 1.47% Traditional ROI: 2.5%
2230 260th Street Winterset, IA Set on 19.5 acres just outside Winterset, this property offers a rare combination of scale...	3 beds \| 4 baths \| 3,660 sq.ft.	$999,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.56% Airbnb Rental Income: $1941 Traditional Rental Income: $3257 Airbnb ROI: -0.4% Traditional ROI: 1.56%
2980 Clark Tower Rd. Winterset, IA Located in scenic Madison County this newly built home and buildings offers peace and quie...	2 beds \| 2 baths \| 4,424 sq.ft.	$478,750	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.78% Airbnb Rental Income: $1209 Traditional Rental Income: $2289 Airbnb ROI: -0.5% Traditional ROI: 2.78%
2210 Ash Tree Drive 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.	$395,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 4.68% Airbnb Rental Income: $1941 Traditional Rental Income: $2227 Airbnb ROI: 2.53% Traditional ROI: 4.68%
2817 Carver Road Winterset, IA A bit of elbow grease and this sweet ranch home could be your dream acreage! With a fabulo...	3 beds \| 3 baths \| 1,600 sq.ft.	$360,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.88% Airbnb Rental Income: $1941 Traditional Rental Income: $2422 Airbnb ROI: 1.94% Traditional ROI: 4.88%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winterset, IA

623 W Green Street

Winterset, IA

4 beds | 3 baths | 1,464 sq.ft.

$309,990

Airbnb cash on cash: N/A

Traditional cash on cash: 5.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2346

Airbnb ROI: N/A

Traditional ROI: 5.34%

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%

323 W Jefferson Street

Winterset, IA

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

$339,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 6.48%

Airbnb Rental Income: $1553

Traditional Rental Income: $3074

Airbnb ROI: 0.3%

Traditional ROI: 6.48%

1913 N 1st Street

Winterset, IA

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

$440,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $1941

Traditional Rental Income: $3144

Airbnb ROI: 0.9%

Traditional ROI: 5.06%

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%

901 E Buchanan Street

Winterset, IA

4 beds | 2 baths | 1,323 sq.ft.

$264,990

Airbnb cash on cash: N/A

Traditional cash on cash: 5.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2056

Airbnb ROI: N/A

Traditional ROI: 5.51%

609 E Filmore Street

Winterset, IA

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

$254,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.29%

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%