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
517 Dragon Willow Lane Middleton, WI Welcome to the Willows, where modern design meets thoughtful functionality in this impress...	4 beds \| 4 baths \| 3,000 sq.ft.	$825,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.34% Airbnb Rental Income: $4740 Traditional Rental Income: $3001 Airbnb ROI: 2.33% Traditional ROI: 1.34%
9420 Stoneywood Boulevard Middleton, WI Welcome home to this impeccably maintained ranch-style residence that combines comfort, st...	4 beds \| 3 baths \| 2,753 sq.ft.	$625,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 1.96% Airbnb Rental Income: $4740 Traditional Rental Income: $2864 Airbnb ROI: 3.5% Traditional ROI: 1.96%
2051 Allen Boulevard #201 Middleton, WI Conveniently located near shopping, restaurants, and the bus line, this beautifully update...	2 beds \| 1 baths \| 866 sq.ft.	$249,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.43% Airbnb Rental Income: $1936 Traditional Rental Income: $1358 Airbnb ROI: 1.71% Traditional ROI: 1.43%
3412 Valley Ridge Road #4 Middleton, WI Adjacent to Pheasant Branch Conservancy, this large Middleton 3-bedroom, 2 full baths, upd...	3 beds \| 2 baths \| 1,442 sq.ft.	$299,900	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.46% Airbnb Rental Income: $3253 Traditional Rental Income: $1864 Airbnb ROI: 4.79% Traditional ROI: 2.46%
9133 Blackhawk Road Middleton, WI Newly renovated! Experience exceptional living in prestigious Blackhawk neighborhood with ...	4 beds \| 4 baths \| 5,135 sq.ft.	$1,400,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.53% Airbnb Rental Income: $4740 Traditional Rental Income: $3558 Airbnb ROI: 0.68% Traditional ROI: 0.53%
4029 Serenbe Street Middleton, WI Experience this elevated, move-in ready home in Middleton. The main level is anchored by t...	5 beds \| 6 baths \| N/A	$1,499,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 0.51% Airbnb Rental Income: $4368 Traditional Rental Income: $2602 Airbnb ROI: 1.12% Traditional ROI: 0.51%
6616 Linnet Lane Middleton, WI Room to gather, space to unwind, and flexibility to make it your own! This 4-bedroom, 2.5-...	4 beds \| 3 baths \| 2,301 sq.ft.	$634,900	Airbnb cash on cash: 4.9% Traditional cash on cash: -0.48% Airbnb Rental Income: $4740 Traditional Rental Income: $572 Airbnb ROI: 4.9% Traditional ROI: -0.48%
6610 Linnet Lane Middleton, WI Nature, convenience, and thoughtful design come together in Tim O'Brien Homes' energy effi...	4 beds \| 3 baths \| 2,340 sq.ft.	$634,900	Airbnb cash on cash: 4.93% Traditional cash on cash: -0.45% Airbnb Rental Income: $4740 Traditional Rental Income: $572 Airbnb ROI: 4.93% Traditional ROI: -0.45%
6622 Linnet Lane Middleton, WI Fresh design and everyday comfort await in Tim O'Brien Homes' energy-efficient Abbott plan...	3 beds \| 3 baths \| 2,028 sq.ft.	$622,900	Airbnb cash on cash: 2.92% Traditional cash on cash: -0.44% Airbnb Rental Income: $3253 Traditional Rental Income: $572 Airbnb ROI: 2.92% Traditional ROI: -0.44%
7135 Johann Farm Road Middleton, WI This Emerald home features a thoughtfully designed, open-concept layout ideal for modern l...	3 beds \| 3 baths \| 1,647 sq.ft.	$589,900	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.42% Airbnb Rental Income: $3253 Traditional Rental Income: $2466 Airbnb ROI: 1.52% Traditional ROI: 1.42%
1214-1216 N High Point Road Middleton, WI Excellent Investment Opportunity in prime Middleton Location!! Well-maintained duplex in t...	6 beds \| 6 baths \| N/A	$899,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 0.74% Airbnb Rental Income: $4368 Traditional Rental Income: $2579 Airbnb ROI: 1.78% Traditional ROI: 0.74%
625 Schewe Road Middleton, WI This Chelsea home features a thoughtfully designed, open-concept layout ideal for modern l...	3 beds \| 3 baths \| 1,667 sq.ft.	$419,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.18% Airbnb Rental Income: $3253 Traditional Rental Income: $2475 Airbnb ROI: 3.3% Traditional ROI: 3.18%
616 Tabby Turn Drive Middleton, WI This Jade home features a thoughtfully designed, open-concept layout ideal for modern livi...	3 beds \| 3 baths \| 1,528 sq.ft.	$499,900	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.98% Airbnb Rental Income: $3253 Traditional Rental Income: $2360 Airbnb ROI: 2.33% Traditional ROI: 1.98%
4057 Morning Poem Place Middleton, WI Under construction, estimated completion mid July 2026. Welcome to this thoughtfully desig...	4 beds \| 4 baths \| N/A	$1,199,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.47% Airbnb Rental Income: $4740 Traditional Rental Income: $3179 Airbnb ROI: 1.99% Traditional ROI: 1.47%
6625 Junco Drive Middleton, WI Your next chapter starts here! This move-in-ready 3-bedroom, 2.5-bath home pairs inviting ...	3 beds \| 3 baths \| 1,989 sq.ft.	$599,900	Airbnb cash on cash: 3.07% Traditional cash on cash: 2.68% Airbnb Rental Income: $3253 Traditional Rental Income: $2304 Airbnb ROI: 3.07% Traditional ROI: 2.68%
6671 Linnet Lane Middleton, WI Picture morning coffee on your covered porch, dinner with friends, and cozy evenings by th...	3 beds \| 3 baths \| 1,989 sq.ft.	$589,900	Airbnb cash on cash: 3.13% Traditional cash on cash: 2.74% Airbnb Rental Income: $3253 Traditional Rental Income: $2304 Airbnb ROI: 3.13% Traditional ROI: 2.74%
5019 Sawgrass Terrace Middleton, WI Beautiful custom home in sought-after Bishops Bay offering 4+ bedrooms, 3.5 baths, and 4,0...	4 beds \| 4 baths \| 4,187 sq.ft.	$749,900	Airbnb cash on cash: 2.26% Traditional cash on cash: 0.45% Airbnb Rental Income: $4740 Traditional Rental Income: $2500 Airbnb ROI: 2.26% Traditional ROI: 0.45%
3324 Glacier Ridge Road Middleton, WI A light-filled, Frank Lloyd Wright-inspired home in desirable Middleton Hills, recently mo...	4 beds \| 4 baths \| 3,625 sq.ft.	$1,095,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.13% Airbnb Rental Income: $4740 Traditional Rental Income: $3471 Airbnb ROI: 1.42% Traditional ROI: 1.13%
7119 Johann Farm Road Middleton, WI This Everest home features a thoughtfully designed, open-concept layout ideal for modern l...	4 beds \| 3 baths \| 2,092 sq.ft.	$659,900	Airbnb cash on cash: 3.07% Traditional cash on cash: 1.41% Airbnb Rental Income: $4740 Traditional Rental Income: $2737 Airbnb ROI: 3.07% Traditional ROI: 1.41%
5021 Prairie Rose Court Middleton, WI Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite and a ...	3 beds \| 3 baths \| 3,020 sq.ft.	$724,900	Airbnb cash on cash: 0.18% Traditional cash on cash: -0.36% Airbnb Rental Income: $3253 Traditional Rental Income: $2157 Airbnb ROI: 0.18% Traditional ROI: -0.36%
8927 Sunstone Lane Middleton, WI Welcome to Hidden Oaks, where quality craftsmanship meets serene surroundings. This beauti...	4 beds \| 3 baths \| 2,411 sq.ft.	$615,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 1.61% Airbnb Rental Income: $4740 Traditional Rental Income: $2459 Airbnb ROI: 3.88% Traditional ROI: 1.61%
5413 Jonquil Court Middleton, WI Don't miss this home with stylish updates in an ideal location just minutes from Orchid He...	3 beds \| 3 baths \| 1,952 sq.ft.	$535,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.55% Airbnb Rental Income: $3253 Traditional Rental Income: $1954 Airbnb ROI: 2.69% Traditional ROI: 1.55%
4956 Enchanted Valley Road Middleton, WI Exceptionally maintained 3BR/2.5 BA home in the Town of Springfield, lovingly cared for by...	3 beds \| 3 baths \| 2,173 sq.ft.	$699,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 0.99% Airbnb Rental Income: $3253 Traditional Rental Income: $2061 Airbnb ROI: 1.7% Traditional ROI: 0.99%
7115 Johann Farm Road Middleton, WI Move-in ready 11/30/26. This Sawyer home features a thoughtfully designed, open-concept la...	3 beds \| 3 baths \| 1,881 sq.ft.	$624,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 0.81% Airbnb Rental Income: $3253 Traditional Rental Income: $2249 Airbnb ROI: 1.28% Traditional ROI: 0.81%
7111 Johann Farm Road Middleton, WI Move-in ready 11/16/26. This Beryl home features a thoughtfully designed, open-concept lay...	3 beds \| 3 baths \| 1,511 sq.ft.	$574,900	Airbnb cash on cash: 1.63% Traditional cash on cash: 0.53% Airbnb Rental Income: $3253 Traditional Rental Income: $1932 Airbnb ROI: 1.63% Traditional ROI: 0.53%
7334 County Road K Middleton, WI Rare opportunity to own a picturesque 2.09-acre country property in the desirable Town of ...	4 beds \| 2 baths \| 2,741 sq.ft.	$779,900	Airbnb cash on cash: 3.1% Traditional cash on cash: 0.98% Airbnb Rental Income: $4740 Traditional Rental Income: $2220 Airbnb ROI: 3.1% Traditional ROI: 0.98%
7401 Century Place #9 Middleton, WI Opportunity to own in Middleton at an approachable price point! This updated 1-bedroom, 1-...	1 beds \| 1 baths \| 890 sq.ft.	$158,500	Airbnb cash on cash: 3.72% Traditional cash on cash: 0.8% Airbnb Rental Income: $1751 Traditional Rental Income: $828 Airbnb ROI: 3.72% Traditional ROI: 0.8%
6659 Linnet Lane Middleton, WI Enjoy the best of Middleton, WI, with nature nearby and premier shopping and dining within...	4 beds \| 3 baths \| 1,868 sq.ft.	$574,900	Airbnb cash on cash: 5.55% Traditional cash on cash: 2.66% Airbnb Rental Income: $4740 Traditional Rental Income: $2212 Airbnb ROI: 5.55% Traditional ROI: 2.66%
4408 Blackwolf Run Middleton, WI Welcome home to this stunning 5 bedroom ranch-style retreat where thoughtful design meets ...	5 beds \| 3 baths \| 2,836 sq.ft.	$824,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 0.78% Airbnb Rental Income: $4368 Traditional Rental Income: $2708 Airbnb ROI: 1.75% Traditional ROI: 0.78%
2805 Century Harbor Road #4 Middleton, WI Lake living meets modern convenience at Century Harbor Condominiums! Ideally situated just...	2 beds \| 2 baths \| 1,250 sq.ft.	$307,500	Airbnb cash on cash: 0.65% Traditional cash on cash: -0.71% Airbnb Rental Income: $1936 Traditional Rental Income: $1030 Airbnb ROI: 0.65% Traditional ROI: -0.71%
9714 Trappers Trail Middleton, WI Beautiful sunlit filled home in the heart of Blackhawk! Trappers Trail is a hidden street ...	5 beds \| 5 baths \| 4,106 sq.ft.	$990,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 0.64% Airbnb Rental Income: $4368 Traditional Rental Income: $3227 Airbnb ROI: 0.88% Traditional ROI: 0.64%

Vacation Rentals in Middleton

There are 58 vacation rental properties available for sale in the city of Middleton . The median list price of Airbnb properties available for sale in Middleton is $559,165 and the average price per square foot is $238. The cash on cash return on vacation rentals in Middleton is 2.00%. The average monthly short term rental income in Middleton is $3,253.

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

There are 58 Airbnb properties available for sale in Middleton.

In 2026, the best neighborhood to buy short term rental property is Middleton.

In November 2026, the average Airbnb occupancy rate in Middleton is 36%.

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

517 Dragon Willow Lane

Middleton, WI

4 beds | 4 baths | 3,000 sq.ft.

$825,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $4740

Traditional Rental Income: $3001

Airbnb ROI: 2.33%

Traditional ROI: 1.34%

9420 Stoneywood Boulevard

Middleton, WI

4 beds | 3 baths | 2,753 sq.ft.

$625,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $4740

Traditional Rental Income: $2864

Airbnb ROI: 3.5%

Traditional ROI: 1.96%

2051 Allen Boulevard #201

Middleton, WI

2 beds | 1 baths | 866 sq.ft.

$249,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $1936

Traditional Rental Income: $1358

Airbnb ROI: 1.71%

Traditional ROI: 1.43%

3412 Valley Ridge Road #4

Middleton, WI

3 beds | 2 baths | 1,442 sq.ft.

$299,900

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $3253

Traditional Rental Income: $1864

Airbnb ROI: 4.79%

Traditional ROI: 2.46%

9133 Blackhawk Road

Middleton, WI

4 beds | 4 baths | 5,135 sq.ft.

$1,400,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $4740

Traditional Rental Income: $3558

Airbnb ROI: 0.68%

Traditional ROI: 0.53%

4029 Serenbe Street

Middleton, WI

5 beds | 6 baths | N/A

$1,499,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $4368

Traditional Rental Income: $2602

Airbnb ROI: 1.12%

Traditional ROI: 0.51%

6616 Linnet Lane

Middleton, WI

4 beds | 3 baths | 2,301 sq.ft.

$634,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: -0.48%

Airbnb Rental Income: $4740

Traditional Rental Income: $572

Airbnb ROI: 4.9%

Traditional ROI: -0.48%

6610 Linnet Lane

Middleton, WI

4 beds | 3 baths | 2,340 sq.ft.

$634,900

Airbnb cash on cash: 4.93%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $4740

Traditional Rental Income: $572

Airbnb ROI: 4.93%