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
703 W Court Avenue Winterset, IA You will love this spacious 1.5 story home located on historic West Court Avenue. The ho...	4 beds \| 2 baths \| 2,698 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $2521 Airbnb ROI: N/A Traditional ROI: 5.85%
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.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $3074 Airbnb ROI: N/A Traditional ROI: 5.66%
401 E Jefferson Street Winterset, IA So much space in this 4 bedroom, 2.5 bath, 2016 sf home! This home has the perfect mix of ...	4 beds \| 3 baths \| 2,016 sq.ft.	$272,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.23% Airbnb Rental Income: $null Traditional Rental Income: $2569 Airbnb ROI: N/A Traditional ROI: 7.23%
712 N 2nd Avenue Winterset, IA Winterset west side 1 1/2 story home with many updates. New furnace & air, roof, windows,...	3 beds \| 1 baths \| 1,358 sq.ft.	$194,900	Airbnb cash on cash: 8.6% Traditional cash on cash: 6.34% Airbnb Rental Income: $2714 Traditional Rental Income: $1655 Airbnb ROI: 8.6% Traditional ROI: 6.34%
119 E Buchanan Street Winterset, IA Classic charm and character describe this beautifully maintained 4-bedroom Winterset home,...	4 beds \| 2 baths \| 1,984 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $2728 Airbnb ROI: N/A Traditional ROI: 5.81%
926 W Court Avenue Winterset, IA So many updates in this sweet 4 bed 2 bath home! Adorable and curb appeal galore! You will...	4 beds \| 2 baths \| 1,387 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $2299 Airbnb ROI: N/A Traditional ROI: 5.33%
217 N 7th Street Winterset, IA Located in a peaceful neighborhood, this cute 1.5 story home is one you don't want to miss...	3 beds \| 1 baths \| 1,477 sq.ft.	$180,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 6.51% Airbnb Rental Income: $2714 Traditional Rental Income: $1677 Airbnb ROI: 8.82% Traditional ROI: 6.51%
404 W Green Street Winterset, IA Cutest cottage style house! 4 bedroom, 2 bath, 1,862 sf. Beautiful new kitchen with stainl...	4 beds \| 2 baths \| 1,862 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $2398 Airbnb ROI: N/A Traditional ROI: 5.17%
1912 Dogwood Lane Winterset, IA Beautiful new construction of this 2-story home in a quiet neighborhood. Home features 3 b...	3 beds \| 3 baths \| 1,712 sq.ft.	$353,450	Airbnb cash on cash: 4.9% Traditional cash on cash: 5.81% Airbnb Rental Income: $2714 Traditional Rental Income: $2373 Airbnb ROI: 4.9% Traditional ROI: 5.81%
2160 114th Court Winterset, IA Amazing New Construction acreage! Picturesque views await in this fantastic home at Sceni...	5 beds \| 5 baths \| 3,111 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $4545 Airbnb ROI: N/A Traditional ROI: 1.4%
315 S 5th Avenue Winterset, IA Located about a block away from Winterset's elementary school, this super cute ranch style...	2 beds \| 2 baths \| 1,120 sq.ft.	$260,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.57% Airbnb Rental Income: $1697 Traditional Rental Income: $1839 Airbnb ROI: 2.07% Traditional ROI: 4.57%
1406 W Mills Street Winterset, IA WELCOME HOME! This beautiful 5 bed/3 full bath home has 2344sf finished upstairs, with ple...	5 beds \| 3 baths \| 2,344 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $2769 Airbnb ROI: N/A Traditional ROI: 5.05%
2202 Ash Tree Drive Winterset, IA	4 beds \| 3 baths \| 1,548 sq.ft.	$401,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $2380 Airbnb ROI: N/A Traditional ROI: 5.02%
1410 W Washington Street Winterset, IA Absolutely stunning totally remodeled home! You will not believe the space in this home un...	5 beds \| 5 baths \| 2,000 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $3806 Airbnb ROI: N/A Traditional ROI: 6.14%
523 N 5th Street Winterset, IA 2BR 1BA ranch home with bonus room and 2 car attached garage with storage. Cute little fro...	2 beds \| 1 baths \| 968 sq.ft.	$180,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 5.6% Airbnb Rental Income: $1697 Traditional Rental Income: $1482 Airbnb ROI: 4.1% Traditional ROI: 5.6%
1233 W Washington Street Winterset, IA If a large open living space is what you have been looking for, look no more. This easy li...	3 beds \| 3 baths \| 2,106 sq.ft.	$295,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 6.37% Airbnb Rental Income: $2714 Traditional Rental Income: $2607 Airbnb ROI: 4.44% Traditional ROI: 6.37%
716 E Filmore Street Winterset, IA Welcome home to your own slice of heaven in the beautiful town of Winterset! Turn key read...	3 beds \| 2 baths \| 1,176 sq.ft.	$215,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 6.79% Airbnb Rental Income: $2714 Traditional Rental Income: $1935 Airbnb ROI: 7.47% Traditional ROI: 6.79%
215 S 2nd Street Winterset, IA Historic Winterset welcomes you!! This home has it all! New Furnace, Central AC, flooring,...	2 beds \| 1 baths \| 672 sq.ft.	$173,900	Airbnb cash on cash: 4.54% Traditional cash on cash: 5.33% Airbnb Rental Income: $1697 Traditional Rental Income: $1357 Airbnb ROI: 4.54% Traditional ROI: 5.33%
710 N 3rd Avenue Winterset, IA WOW! Check out this beautiful remodel. This 3 bedroom ranch is right on trend with colors ...	3 beds \| 1 baths \| 962 sq.ft.	$242,500	Airbnb cash on cash: 6.69% Traditional cash on cash: 4.6% Airbnb Rental Income: $2714 Traditional Rental Income: $1592 Airbnb ROI: 6.69% Traditional ROI: 4.6%
2981 214th Trail Winterset, IA Spectacular 3.7 acres of rolling hills, trees, a pond, chicken coop and a barn for the pic...	2 beds \| 2 baths \| 1,031 sq.ft.	$375,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.67% Airbnb Rental Income: $1697 Traditional Rental Income: $1750 Airbnb ROI: 1.17% Traditional ROI: 2.67%
2064 226th Court Winterset, IA Spread out in this amazing farmhouse style acreage! This acreage is perfectly located just...	4 beds \| 4 baths \| 2,549 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $3120 Airbnb ROI: N/A Traditional ROI: 3.25%
2331 Clark Tower Road Winterset, IA Affordable acreage alert! Great location, just 2 miles from Winterset on a paved county hi...	2 beds \| 1 baths \| 912 sq.ft.	$165,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 7.87% Airbnb Rental Income: $1697 Traditional Rental Income: $1549 Airbnb ROI: 5.81% Traditional ROI: 7.87%
209 W Jefferson Street #24 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,080 sq.ft.	$230,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.74% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.64% Traditional ROI: 4.74%
209 W Jefferson Street #23 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,080 sq.ft.	$230,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.74% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.64% Traditional ROI: 4.74%
209 W Jefferson Street #22 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,103 sq.ft.	$215,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 4.86% Airbnb Rental Income: $1697 Traditional Rental Income: $1845 Airbnb ROI: 1.82% Traditional ROI: 4.86%
209 W Jefferson Street #21 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,103 sq.ft.	$215,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 5.13% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.82% Traditional ROI: 5.13%
209 W Jefferson Street #20 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,103 sq.ft.	$215,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 5.13% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.82% Traditional ROI: 5.13%
209 W Jefferson Street #19 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	1 beds \| 1 baths \| 1,103 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.7% Airbnb Rental Income: $null Traditional Rental Income: $1922 Airbnb ROI: N/A Traditional ROI: 5.7%
209 W Jefferson Street #18 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,080 sq.ft.	$230,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.74% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.64% Traditional ROI: 4.74%
209 W Jefferson Street #17 Winterset, IA Welcome to the newly renovated JW Flats - a new type of living for the Madison County comm...	2 beds \| 2 baths \| 1,080 sq.ft.	$230,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.74% Airbnb Rental Income: $1697 Traditional Rental Income: $1899 Airbnb ROI: 1.64% Traditional ROI: 4.74%
217 E Jefferson Street Winterset, IA Unique property; two homes 1 lot. Main home is 5 bedroom, 2 remodeled baths with new carp...	5 beds \| 2 baths \| 2,212 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.24% Airbnb Rental Income: $null Traditional Rental Income: $2565 Airbnb ROI: N/A Traditional ROI: 7.24%
610 W Stone Street Winterset, IA Welcome to 610 W Stone St, a delightful residence nestled in the picturesque town of Winte...	3 beds \| 3 baths \| 1,278 sq.ft.	$315,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 4.7% Airbnb Rental Income: $2714 Traditional Rental Income: $2325 Airbnb ROI: 3.85% Traditional ROI: 4.7%
1109 Meredith Circle Winterset, IA This traditional 4 Bedroom two story home is anything but traditional!! The contemporary ...	4 beds \| 3 baths \| 2,004 sq.ft.	$312,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $2655 Airbnb ROI: N/A Traditional ROI: 6.37%
2197 175th Court Winterset, IA Great Location just North of Winterset off hwy 169. 2b/1b unfinished walk-out ranch ...	2 beds \| 1 baths \| 1,024 sq.ft.	$219,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 5.03% Airbnb Rental Income: $1697 Traditional Rental Income: $1551 Airbnb ROI: 3.46% Traditional ROI: 5.03%
604 S 2nd Avenue Winterset, IA Super spacious walk-out brick ranch on a large corner lot! The 1st floor features: 2 bedr...	2 beds \| 2 baths \| 1,580 sq.ft.	$260,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.41% Airbnb Rental Income: $1697 Traditional Rental Income: $2073 Airbnb ROI: 1.96% Traditional ROI: 5.41%
608 W South Street Winterset, IA Adorable well maintained 2 bedroom home. Owned by the same family for over 70 years. Invi...	2 beds \| 1 baths \| 1,072 sq.ft.	$215,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 5.18% Airbnb Rental Income: $1697 Traditional Rental Income: $1587 Airbnb ROI: 3.4% Traditional ROI: 5.18%
304 E Washington Street Winterset, IA This one 1/2 story home is all new on the inside with many updates on the exterior. It fea...	3 beds \| 1 baths \| 1,005 sq.ft.	$239,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 5.11% Airbnb Rental Income: $2714 Traditional Rental Income: $1558 Airbnb ROI: 7.39% Traditional ROI: 5.11%
306 S 4th Street Winterset, IA Super sweet 2 bedroom, 1.5 bath ranch home. Built in 2004, this ranch is in "like new" con...	2 beds \| 2 baths \| 1,032 sq.ft.	$260,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.43% Airbnb Rental Income: $1697 Traditional Rental Income: $1743 Airbnb ROI: 2.32% Traditional ROI: 4.43%
815 W Court Avenue Winterset, IA Appealing brick ranch with two bedrooms & 1.5 bath on Winterset West side. This home has a...	2 beds \| 2 baths \| 1,254 sq.ft.	$270,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.46% Airbnb Rental Income: $1697 Traditional Rental Income: $1939 Airbnb ROI: 1.65% Traditional ROI: 4.46%
902 9th Avenue Winterset, IA New construction ranch with a finished walk-out lower level. Still time to pick out finis...	4 beds \| 3 baths \| 1,590 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.55% Airbnb Rental Income: $null Traditional Rental Income: $2361 Airbnb ROI: N/A Traditional ROI: 3.55%

Real Estate investment in Winterset, IA

There are 55 properties for sale in the city of Winterset . The median list price in Winterset is $251,250 and the average price per square foot is $168. In December 2024, the average monthly cash on cash return in Winterset is 5.00%. The average monthly rental income in Winterset is $2,006.

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

There are 55 investment properties available for sale in Winterset.

In 2024, 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 $2,006.

Your search for investment property begins and ends here

Investment Property for Sale in Winterset, IA

703 W Court Avenue

Winterset, IA

4 beds | 2 baths | 2,698 sq.ft.

$295,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2521

Airbnb ROI: N/A

Traditional ROI: 5.85%

323 W Jefferson Street

Winterset, IA

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

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.66%

Airbnb Rental Income: $null

Traditional Rental Income: $3074

Airbnb ROI: N/A

Traditional ROI: 5.66%

401 E Jefferson Street

Winterset, IA

4 beds | 3 baths | 2,016 sq.ft.

$272,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.23%

Airbnb Rental Income: $null

Traditional Rental Income: $2569

Airbnb ROI: N/A

Traditional ROI: 7.23%

712 N 2nd Avenue

Winterset, IA

3 beds | 1 baths | 1,358 sq.ft.

$194,900

Airbnb cash on cash: 8.6%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $2714

Traditional Rental Income: $1655

Airbnb ROI: 8.6%

Traditional ROI: 6.34%

119 E Buchanan Street

Winterset, IA

4 beds | 2 baths | 1,984 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2728

Airbnb ROI: N/A

Traditional ROI: 5.81%

926 W Court Avenue

Winterset, IA

4 beds | 2 baths | 1,387 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2299

Airbnb ROI: N/A

Traditional ROI: 5.33%

217 N 7th Street

Winterset, IA

3 beds | 1 baths | 1,477 sq.ft.

$180,000

Airbnb cash on cash: 8.82%

Traditional cash on cash: 6.51%

Airbnb Rental Income: $2714

Traditional Rental Income: $1677

Airbnb ROI: 8.82%

Traditional ROI: 6.51%

404 W Green Street

Winterset, IA

4 beds | 2 baths | 1,862 sq.ft.

$335,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.17%

Airbnb Rental Income: $null

Traditional Rental Income: $2398

Airbnb ROI: N/A