Real Estate Investment Properties for Sale in Baraboo, WI

Looking for investment property in Baraboo, WI with high ROI ?

Explore a variety of short-term homes & houses in Baraboo, WI. Invest wisely with VRBO & Baraboo, WI 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 Baraboo, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1421 21st Street Baraboo, WI Welcome to effortless living in the City of Baraboo; where small-town charm meets everyday...	5 beds \| 2 baths \| 2,332 sq.ft.	$430,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.97% Airbnb Rental Income: $3838 Traditional Rental Income: $2697 Airbnb ROI: 4.75% Traditional ROI: 3.97%
704 Ash Street Baraboo, WI Prime Build-to-Suit Opportunity near Downtown Baraboo! Unlock the potential of 704 Ash Str...	5 beds \| 6 baths \| 4,530 sq.ft.	$499,900	Airbnb cash on cash: 4.63% Traditional cash on cash: 10.81% Airbnb Rental Income: $3838 Traditional Rental Income: $5896 Airbnb ROI: 4.63% Traditional ROI: 10.81%
E12505 County Road W Baraboo, WI Turnkey Investment Opportunity. Presenting Orchard Park Mobile Home Park, a well-maintaine...	13 beds \| N/A baths \| N/A	$1,349,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.4% Airbnb Rental Income: $3838 Traditional Rental Income: $5336 Airbnb ROI: 0.54% Traditional ROI: 2.4%
521 Roosevelt Street Baraboo, WI Welcome home to this beautiful 3bd 3ba Ranch home located in the desirable Greenfield Rese...	3 beds \| 2 baths \| 1,577 sq.ft.	$425,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 3% Airbnb Rental Income: $1742 Traditional Rental Income: $2318 Airbnb ROI: 0.35% Traditional ROI: 3%
602 Eisenhower Street Baraboo, WI Sip your morning coffee and enjoy peaceful views from the covered front porch of this thou...	3 beds \| 3 baths \| 1,751 sq.ft.	$415,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.3% Airbnb Rental Income: $1742 Traditional Rental Income: $2401 Airbnb ROI: 0.37% Traditional ROI: 3.3%
810 Rosemary Lane Baraboo, WI APPROX. $150,000 IN IMPROVEMENTS IN PAST YEAR - SEE COMPLETE LIST! Gorgeous, NEWLY UPDATED...	4 beds \| 3 baths \| 2,728 sq.ft.	$615,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.7% Airbnb Rental Income: $2925 Traditional Rental Income: $2858 Airbnb ROI: 1.64% Traditional ROI: 2.7%
1074 Tinkham Trail Baraboo, WI Designed by one of the top short term rental designers in the nation, this property is tru...	5 beds \| 4 baths \| 2,650 sq.ft.	$624,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 3.91% Airbnb Rental Income: $3838 Traditional Rental Income: $3400 Airbnb ROI: 3.24% Traditional ROI: 3.91%
S4166 Whispering Pines Drive Baraboo, WI This spacious 5-bedroom, 3.5-bath home in Wynsong Estates has been thoughtfully updated in...	5 beds \| 4 baths \| 4,439 sq.ft.	$714,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.54% Airbnb Rental Income: $3838 Traditional Rental Income: $3845 Airbnb ROI: 2.29% Traditional ROI: 3.54%
S4362 Fox Hill Circle Baraboo, WI Tucked at the end of a wooded cul-de-sac sitting on .97 acres, this sprawling 5,573 sq ft ...	5 beds \| 4 baths \| 5,573 sq.ft.	$774,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 3.13% Airbnb Rental Income: $3838 Traditional Rental Income: $3849 Airbnb ROI: 1.97% Traditional ROI: 3.13%
E11616 N Reedsburg Road Baraboo, WI Spacious Family Home on Acreage with Beautiful Bluff Views! Wonderful opportunity to own t...	4 beds \| 3 baths \| 3,052 sq.ft.	$529,900	Airbnb cash on cash: 2.59% Traditional cash on cash: 4.26% Airbnb Rental Income: $2925 Traditional Rental Income: $3080 Airbnb ROI: 2.59% Traditional ROI: 4.26%
831 Island Court Baraboo, WI Experience refined living in this exceptional 4-bedroom home set on a sprawling lot along ...	4 beds \| 3 baths \| 4,714 sq.ft.	$689,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.65% Airbnb Rental Income: $2925 Traditional Rental Income: $3213 Airbnb ROI: 1.15% Traditional ROI: 2.65%
1215 Springbrook Drive Baraboo, WI Offer W/Bump.This is the one youâve been waiting for. Welcome to 1215 Springbrook Dr in ...	3 beds \| 3 baths \| 2,146 sq.ft.	$465,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.94% Airbnb Rental Income: $1742 Traditional Rental Income: $2746 Airbnb ROI: 0.53% Traditional ROI: 3.94%
E10282 Greimel Road Baraboo, WI Offering 4 bedrooms and 3.5 baths on a generous 1.03-acre lot, this home delivers the perf...	4 beds \| 4 baths \| 2,820 sq.ft.	$499,990	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.08% Airbnb Rental Income: $2925 Traditional Rental Income: $3393 Airbnb ROI: 2.63% Traditional ROI: 5.08%
S4395 Cedarberry Lane Baraboo, WI Welcome to your sanctuary in Cedar Ridge! Stunning Baraboo-area home perfectly blends mode...	4 beds \| 4 baths \| 2,590 sq.ft.	$599,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 3.85% Airbnb Rental Income: $2925 Traditional Rental Income: $3239 Airbnb ROI: 2.08% Traditional ROI: 3.85%
1106 21st Street Baraboo, WI Fall in love with this beautiful executive custom-built ranch in a sought-after neighborho...	5 beds \| 3 baths \| 4,541 sq.ft.	$699,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.09% Airbnb Rental Income: $3838 Traditional Rental Income: $3179 Airbnb ROI: 1.83% Traditional ROI: 2.09%
517 Highland Drive Baraboo, WI Located in a highly desirable area just minutes from downtown, it provides easy access to ...	5 beds \| 3 baths \| 2,700 sq.ft.	$319,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 7.5% Airbnb Rental Income: $3838 Traditional Rental Income: $3072 Airbnb ROI: 7.29% Traditional ROI: 7.5%
1111 Spruce Drive Baraboo, WI Everything is NEW in this 3 bedrooms, 2 bath home in the Parkside Subdivision. This lovely...	3 beds \| 2 baths \| 1,456 sq.ft.	$379,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.43% Airbnb Rental Income: $1742 Traditional Rental Income: $2122 Airbnb ROI: 1.01% Traditional ROI: 3.43%
312 8th Avenue Baraboo, WI Move right in and enjoy everything this vibrant community has to offer! This is the turn-k...	4 beds \| 1 baths \| 1,296 sq.ft.	$239,900	Airbnb cash on cash: 7.33% Traditional cash on cash: 3.28% Airbnb Rental Income: $2925 Traditional Rental Income: $1330 Airbnb ROI: 7.33% Traditional ROI: 3.28%
312 Roosevelt Street Baraboo, WI Set on a quiet street with backyard privacy and no neighbors behind, this almost-new 4-bed...	4 beds \| 3 baths \| 2,645 sq.ft.	$485,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 5.44% Airbnb Rental Income: $2925 Traditional Rental Income: $3031 Airbnb ROI: 3.72% Traditional ROI: 5.44%
406 Amey Drive Baraboo, WI Calling all investors!! This well-maintained four-unit apartment buildingânestled among ...	6 beds \| N/A baths \| N/A	$550,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 2.63% Airbnb Rental Income: $3838 Traditional Rental Income: $2570 Airbnb ROI: 3.48% Traditional ROI: 2.63%

Real Estate investment in Baraboo, WI

There are 37 properties for sale in the city of Baraboo . The median list price in Baraboo is $294,748 and the average price per square foot is $163. In June 2026, the average monthly cash on cash return in Baraboo is 3.00%. The average monthly rental income in Baraboo is $2,563.

Baraboo, WI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 37 investment properties available for sale in Baraboo.

In 2026, the best neighborhood to buy investment property is Baraboo.

The ROI for Long-Term is higher than the Short-Term in Baraboo with average rental income of $2,563.

Your search for investment property begins and ends here

Investment Property for Sale in Baraboo, WI

1421 21st Street

Baraboo, WI

5 beds | 2 baths | 2,332 sq.ft.

$430,000

Airbnb cash on cash: 4.75%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $3838

Traditional Rental Income: $2697

Airbnb ROI: 4.75%

Traditional ROI: 3.97%

704 Ash Street

Baraboo, WI

5 beds | 6 baths | 4,530 sq.ft.

$499,900

Airbnb cash on cash: 4.63%

Traditional cash on cash: 10.81%

Airbnb Rental Income: $3838

Traditional Rental Income: $5896

Airbnb ROI: 4.63%

Traditional ROI: 10.81%

E12505 County Road W

Baraboo, WI

13 beds | N/A baths | N/A

$1,349,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3838

Traditional Rental Income: $5336

Airbnb ROI: 0.54%

Traditional ROI: 2.4%

521 Roosevelt Street

Baraboo, WI

3 beds | 2 baths | 1,577 sq.ft.

$425,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 3%

Airbnb Rental Income: $1742

Traditional Rental Income: $2318

Airbnb ROI: 0.35%

Traditional ROI: 3%

602 Eisenhower Street

Baraboo, WI

3 beds | 3 baths | 1,751 sq.ft.

$415,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1742

Traditional Rental Income: $2401

Airbnb ROI: 0.37%

Traditional ROI: 3.3%

810 Rosemary Lane

Baraboo, WI

4 beds | 3 baths | 2,728 sq.ft.

$615,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2925

Traditional Rental Income: $2858

Airbnb ROI: 1.64%

Traditional ROI: 2.7%

1074 Tinkham Trail

Baraboo, WI

5 beds | 4 baths | 2,650 sq.ft.

$624,000

Airbnb cash on cash: 3.24%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $3838

Traditional Rental Income: $3400

Airbnb ROI: 3.24%

Traditional ROI: 3.91%

S4166 Whispering Pines Drive

Baraboo, WI

5 beds | 4 baths | 4,439 sq.ft.

$714,900

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $3838

Traditional Rental Income: $3845

Airbnb ROI: 2.29%