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.	$460,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 3.65% Airbnb Rental Income: $3115 Traditional Rental Income: $2697 Airbnb ROI: 2.98% Traditional ROI: 3.65%
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: 3.34% Traditional cash on cash: 10.81% Airbnb Rental Income: $3115 Traditional Rental Income: $5896 Airbnb ROI: 3.34% 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: 0.06% Traditional cash on cash: 2.4% Airbnb Rental Income: $3115 Traditional Rental Income: $5336 Airbnb ROI: 0.06% Traditional ROI: 2.4%
73 Morningside Road Baraboo, WI Brand new construction in Hickory Hills, one of the Dells and Baraboo's most best-kept sec...	3 beds \| 2 baths \| 1,493 sq.ft.	$387,500	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.63% Airbnb Rental Income: $1345 Traditional Rental Income: $2172 Airbnb ROI: 1.22% Traditional ROI: 4.63%
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.	$425,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 3.2% Airbnb Rental Income: $1345 Traditional Rental Income: $2401 Airbnb ROI: -0.49% Traditional ROI: 3.2%
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.	$649,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 3.72% Airbnb Rental Income: $3115 Traditional Rental Income: $3400 Airbnb ROI: 2.08% Traditional ROI: 3.72%
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: 1.38% Traditional cash on cash: 3.54% Airbnb Rental Income: $3115 Traditional Rental Income: $3845 Airbnb ROI: 1.38% Traditional ROI: 3.54%
S4362 Fox Hill Circle Baraboo, WI Experience unmatched space in this 5,573 sq ft ranch on Barabooâs north edge, tucked at ...	5 beds \| 4 baths \| 5,573 sq.ft.	$799,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 2.95% Airbnb Rental Income: $3115 Traditional Rental Income: $3849 Airbnb ROI: 1.01% Traditional ROI: 2.95%
1130-1132 12th Street Baraboo, WI Well~maintained east~side Baraboo duplex offering an excellent investment opportunity. Ea...	4 beds \| N/A baths \| N/A	$525,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.3% Airbnb Rental Income: $2012 Traditional Rental Income: $2306 Airbnb ROI: 0.63% Traditional ROI: 2.3%
422 Eisenhower Street Baraboo, WI Estimated construction completion date: 05/01/2026. Current stage: interior finish work. N...	3 beds \| 2 baths \| 1,913 sq.ft.	$489,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.21% Airbnb Rental Income: $1345 Traditional Rental Income: $2596 Airbnb ROI: 0.57% Traditional ROI: 4.21%
733 5th Street Baraboo, WI Classic Victorian with all of the charm & style of yesteryear. Home features 5 bedrooms, 3...	5 beds \| 3 baths \| 2,650 sq.ft.	$350,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 7.01% Airbnb Rental Income: $3115 Traditional Rental Income: $3251 Airbnb ROI: 4.44% Traditional ROI: 7.01%
411 Roosevelt Street Baraboo, WI Estimate construction completion date: 06/08/2026. Current construction stage: interior fi...	4 beds \| 3 baths \| 2,636 sq.ft.	$464,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 4.03% Airbnb Rental Income: $2012 Traditional Rental Income: $3078 Airbnb ROI: 0.37% Traditional ROI: 4.03%
E11616 N Reedsburg Road Baraboo, WI LOCATION, LOCATION, LOCATION! Wonderful opportunity to own this beautiful home with an ama...	4 beds \| 3 baths \| 3,052 sq.ft.	$569,900	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.9% Airbnb Rental Income: $2012 Traditional Rental Income: $3080 Airbnb ROI: 0.91% Traditional ROI: 3.9%
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.	$694,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.62% Airbnb Rental Income: $2012 Traditional Rental Income: $3213 Airbnb ROI: -0.04% Traditional ROI: 2.62%
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: -0.23% Traditional cash on cash: 3.94% Airbnb Rental Income: $1345 Traditional Rental Income: $2746 Airbnb ROI: -0.23% Traditional ROI: 3.94%
E10282 Greimel Road Baraboo, WI Welcome to this beautifully maintained 2-story home in the desirable Delton Woods Subdivis...	4 beds \| 4 baths \| 2,820 sq.ft.	$499,990	Airbnb cash on cash: 1% Traditional cash on cash: 5.08% Airbnb Rental Income: $2012 Traditional Rental Income: $3393 Airbnb ROI: 1% 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: 0.72% Traditional cash on cash: 3.85% Airbnb Rental Income: $2012 Traditional Rental Income: $3239 Airbnb ROI: 0.72% 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: 0.91% Traditional cash on cash: 2.09% Airbnb Rental Income: $3115 Traditional Rental Income: $3179 Airbnb ROI: 0.91% Traditional ROI: 2.09%
1440 Tillberry Drive Baraboo, WI Open House May 2nd 1-3pm. No showings until 4/30/26 to allow removal of personal property ...	5 beds \| 3 baths \| 2,712 sq.ft.	$399,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 5.23% Airbnb Rental Income: $3115 Traditional Rental Income: $3067 Airbnb ROI: 3.46% Traditional ROI: 5.23%
625 Bascom Hill Drive Baraboo, WI Can you believe your eyes?! This beautiful property is for sale! Feel the warmth of being ...	4 beds \| 4 baths \| 3,138 sq.ft.	$459,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 5.49% Airbnb Rental Income: $2012 Traditional Rental Income: $3529 Airbnb ROI: 0.75% Traditional ROI: 5.49%
409 1st Street Baraboo, WI NO SHOWINGS UNTIL OPEN HOUSE ON SUNDAY 4/26 10-12. Spacious and inviting 4-bedroom home o...	4 beds \| 4 baths \| 2,607 sq.ft.	$289,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 10.2% Airbnb Rental Income: $2012 Traditional Rental Income: $3510 Airbnb ROI: 2.79% Traditional ROI: 10.2%

Real Estate investment in Baraboo, WI

There are 30 properties for sale in the city of Baraboo . The median list price in Baraboo is $460,000 and the average price per square foot is $254. In May 2026, the average monthly cash on cash return in Baraboo is 4.00%. The average monthly rental income in Baraboo is $2,697.

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

There are 30 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 $2,697.

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.

$460,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $3115

Traditional Rental Income: $2697

Airbnb ROI: 2.98%

Traditional ROI: 3.65%

704 Ash Street

Baraboo, WI

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

$499,900

Airbnb cash on cash: 3.34%

Traditional cash on cash: 10.81%

Airbnb Rental Income: $3115

Traditional Rental Income: $5896

Airbnb ROI: 3.34%

Traditional ROI: 10.81%

E12505 County Road W

Baraboo, WI

13 beds | N/A baths | N/A

$1,349,000

Airbnb cash on cash: 0.06%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3115

Traditional Rental Income: $5336

Airbnb ROI: 0.06%

Traditional ROI: 2.4%

73 Morningside Road

Baraboo, WI

3 beds | 2 baths | 1,493 sq.ft.

$387,500

Airbnb cash on cash: 1.22%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $1345

Traditional Rental Income: $2172

Airbnb ROI: 1.22%

Traditional ROI: 4.63%

602 Eisenhower Street

Baraboo, WI

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

$425,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $1345

Traditional Rental Income: $2401

Airbnb ROI: -0.49%

Traditional ROI: 3.2%

1074 Tinkham Trail

Baraboo, WI

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

$649,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3115

Traditional Rental Income: $3400

Airbnb ROI: 2.08%

Traditional ROI: 3.72%

S4166 Whispering Pines Drive

Baraboo, WI

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

$714,900

Airbnb cash on cash: 1.38%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $3115

Traditional Rental Income: $3845

Airbnb ROI: 1.38%

Traditional ROI: 3.54%

S4362 Fox Hill Circle

Baraboo, WI

5 beds | 4 baths | 5,573 sq.ft.

$799,900

Airbnb cash on cash: 1.01%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $3115

Traditional Rental Income: $3849

Airbnb ROI: 1.01%