Airbnb Properties for Sale in Middleton, WI

Looking for a vacation rental investment in Middleton, WI with high ROI ?

Explore a range of newly added short-term rental homes in Middleton, WI. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Middleton, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
228 Little Bear Drive Middleton, WI Enjoy this like new, move-in ready 4 bedroom home on the ideal West side of Madison. Thoug...	4 beds \| 3 baths \| 2,097 sq.ft.	$709,900	Airbnb cash on cash: 4.04% Traditional cash on cash: 1.66% Airbnb Rental Income: $5555 Traditional Rental Income: $2864 Airbnb ROI: 4.04% Traditional ROI: 1.66%
7013 Cardinal Drive Middleton, WI Perfectly situated in the heart of Middleton, close to everything, yet tucked away on a qu...	4 beds \| 3 baths \| 2,448 sq.ft.	$619,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 2.54% Airbnb Rental Income: $5555 Traditional Rental Income: $2850 Airbnb ROI: 5.29% Traditional ROI: 2.54%
8903 White Coral Way Middleton, WI Beautifully designed home in the Hidden Oaks neighborhood exudes warmth & charm throughout...	4 beds \| 4 baths \| 2,691 sq.ft.	$585,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 2.92% Airbnb Rental Income: $5555 Traditional Rental Income: $3095 Airbnb ROI: 5.38% Traditional ROI: 2.92%
630 Big Stone Trail Middleton, WI MOTIVATED SELLER! Brand new Pantry & Master Closet 2025. Experience luxury, comfort & conv...	5 beds \| 4 baths \| 4,705 sq.ft.	$1,060,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.55% Airbnb Rental Income: $4974 Traditional Rental Income: $3820 Airbnb ROI: 1.69% Traditional ROI: 1.55%
7403 Elmwood Avenue Middleton, WI Rare opportunity to own this stunning, one of a kind 4 bedroom home just steps from all do...	4 beds \| 3 baths \| 2,997 sq.ft.	$1,250,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 0.67% Airbnb Rental Income: $5555 Traditional Rental Income: $2943 Airbnb ROI: 1.96% Traditional ROI: 0.67%
6663 S Chickahauk Trail Middleton, WI This elegant condo is situated in the desirable Ridges of Pheasant Branch. No expenses wer...	4 beds \| 4 baths \| 3,235 sq.ft.	$799,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.56% Airbnb Rental Income: $5555 Traditional Rental Income: $3747 Airbnb ROI: 3.49% Traditional ROI: 2.56%
4205 Monarch Court Middleton, WI This Extremely well maintained and spotless clean house sitting in near half acre lot is a...	5 beds \| 4 baths \| 3,415 sq.ft.	$725,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.29% Airbnb Rental Income: $4974 Traditional Rental Income: $3890 Airbnb ROI: 3.39% Traditional ROI: 3.29%
402 Burnt Sienna Drive Middleton, WI Impeccably designed & maintained, this exquisite 2017 ranch showcases luxury & functionali...	4 beds \| 3 baths \| 3,138 sq.ft.	$849,900	Airbnb cash on cash: 2.85% Traditional cash on cash: 1.22% Airbnb Rental Income: $5555 Traditional Rental Income: $3156 Airbnb ROI: 2.85% Traditional ROI: 1.22%
7122 Mockingbird Lane Middleton, WI Fall in love with this incredible find! This well cared-for home in a fantastic location i...	4 beds \| 3 baths \| 2,830 sq.ft.	$539,900	Airbnb cash on cash: 6.21% Traditional cash on cash: 3.58% Airbnb Rental Income: $5555 Traditional Rental Income: $3111 Airbnb ROI: 6.21% Traditional ROI: 3.58%
6846 Frank Lloyd Wright Avenue Middleton, WI Rare Middleton Hills 3 bed/3 bath ranch styled condo is elegant both inside and out. This ...	3 beds \| 3 baths \| 3,250 sq.ft.	$825,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.93% Airbnb Rental Income: $4974 Traditional Rental Income: $2446 Airbnb ROI: 2.89% Traditional ROI: 0.93%
1004 Rooster Run Middleton, WI Wake up to views of Tiedeman's Pond in Middleton! This generous sized condo has an open fl...	4 beds \| 4 baths \| 3,516 sq.ft.	$674,900	Airbnb cash on cash: 4.55% Traditional cash on cash: 3.13% Airbnb Rental Income: $5555 Traditional Rental Income: $3549 Airbnb ROI: 4.55% Traditional ROI: 3.13%
8601 Stonebrook Circle Middleton, WI CUSTOM-BUILT, FULLY EXPOSED RANCH WITH OPEN SPACIOUS DESIGN ON JUST OVER A HALF-ACRE FENCE...	5 beds \| 3 baths \| 4,209 sq.ft.	$899,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.95% Airbnb Rental Income: $4974 Traditional Rental Income: $3304 Airbnb ROI: 2.73% Traditional ROI: 1.95%
4865 Champions Run Middleton, WI Beautiful Executive 4-bedroom, 4 bath, 4 car heated garage & 5,000 sq ft custom Ranch home...	4 beds \| 4 baths \| 5,000 sq.ft.	$1,510,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.61% Airbnb Rental Income: $5555 Traditional Rental Income: $3718 Airbnb ROI: 1.13% Traditional ROI: 0.61%
4329 Callaway Court Middleton, WI A rare opportunity in the renowned Villas of Callaway Court in beautiful Bishops Bay, The ...	4 beds \| 4 baths \| 3,632 sq.ft.	$1,499,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.15% Airbnb Rental Income: $5555 Traditional Rental Income: $3899 Airbnb ROI: 0.54% Traditional ROI: 0.15%
2906 Ravine Drive Middleton, WI This Middleton gem is within walking distance to restaurants, parks, & Pheasant Branch Con...	3 beds \| 2 baths \| 2,370 sq.ft.	$450,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 2.4% Airbnb Rental Income: $3152 Traditional Rental Income: $2090 Airbnb ROI: 3.22% Traditional ROI: 2.4%

Vacation Rentals in Middleton

There are 28 vacation rental properties available for sale in the city of Middleton . The median list price of Airbnb properties available for sale in Middleton is $725,000 and the average price per square foot is $243. The cash on cash return on vacation rentals in Middleton is 3.00%. The average monthly short term rental income in Middleton is $4,974.

Middleton, WI Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 28 Airbnb properties available for sale in Middleton.

In 2025, the best neighborhood to buy short term rental property is Middleton.

In September 2025, the average Airbnb occupancy rate in Middleton is 32%.

Airbnb data on vacation rentals in Middleton, WI is available at Mashvisor. You can access data such as listings, real-time pricing trends, Middleton, WI market insights, guest information and booking details, seasonality trends and historical Middleton, WI Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Middleton, WI

228 Little Bear Drive

Middleton, WI

4 beds | 3 baths | 2,097 sq.ft.

$709,900

Airbnb cash on cash: 4.04%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $5555

Traditional Rental Income: $2864

Airbnb ROI: 4.04%

Traditional ROI: 1.66%

7013 Cardinal Drive

Middleton, WI

4 beds | 3 baths | 2,448 sq.ft.

$619,000

Airbnb cash on cash: 5.29%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $5555

Traditional Rental Income: $2850

Airbnb ROI: 5.29%

Traditional ROI: 2.54%

8903 White Coral Way

Middleton, WI

4 beds | 4 baths | 2,691 sq.ft.

$585,000

Airbnb cash on cash: 5.38%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $5555

Traditional Rental Income: $3095

Airbnb ROI: 5.38%

Traditional ROI: 2.92%

630 Big Stone Trail

Middleton, WI

5 beds | 4 baths | 4,705 sq.ft.

$1,060,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $4974

Traditional Rental Income: $3820

Airbnb ROI: 1.69%

Traditional ROI: 1.55%

7403 Elmwood Avenue

Middleton, WI

4 beds | 3 baths | 2,997 sq.ft.

$1,250,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $5555

Traditional Rental Income: $2943

Airbnb ROI: 1.96%

Traditional ROI: 0.67%

6663 S Chickahauk Trail

Middleton, WI

4 beds | 4 baths | 3,235 sq.ft.

$799,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5555

Traditional Rental Income: $3747

Airbnb ROI: 3.49%

Traditional ROI: 2.56%

4205 Monarch Court

Middleton, WI

5 beds | 4 baths | 3,415 sq.ft.

$725,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $4974

Traditional Rental Income: $3890

Airbnb ROI: 3.39%

Traditional ROI: 3.29%

402 Burnt Sienna Drive

Middleton, WI

4 beds | 3 baths | 3,138 sq.ft.

$849,900

Airbnb cash on cash: 2.85%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $5555

Traditional Rental Income: $3156

Airbnb ROI: 2.85%