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.

Lubbock Investment Property for Sale in Winterset, IA

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

Showing 50 Lubbock Investment Property 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

Lubbock Investment Property 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%