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 Ln Middleton, WI Middleton Schools! Welcome to this wonderful home set in the desirable Willows subdivision...	4 beds \| 3 baths \| 3,000 sq.ft.	$825,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 1.6% Airbnb Rental Income: $4740 Traditional Rental Income: $3001 Airbnb ROI: 2.59% Traditional ROI: 1.6%
719 Cricket Ln #1 Middleton, WI Move in ready end unit three bedroom 2 1/2 bath townhome located in the highly desirable G...	3 beds \| 2 baths \| 1,815 sq.ft.	$349,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.11% Airbnb Rental Income: $3253 Traditional Rental Income: $2149 Airbnb ROI: 3.25% Traditional ROI: 2.11%
2809 Century Harbor Rd #3 Middleton, WI Do not miss this updated move in ready condo with lake access! Walk to the water to see t...	1 beds \| 1 baths \| 850 sq.ft.	$239,900	Airbnb cash on cash: 0.98% Traditional cash on cash: -0.94% Airbnb Rental Income: $1751 Traditional Rental Income: $834 Airbnb ROI: 0.98% Traditional ROI: -0.94%
7106 Fortune Dr #3 Middleton, WI Pristine and and move-in ready 2 bedroom Middleton condo is looking for a new owner! This ...	2 beds \| 1 baths \| 870 sq.ft.	$190,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 2.16% Airbnb Rental Income: $1936 Traditional Rental Income: $1126 Airbnb ROI: 3.81% Traditional ROI: 2.16%
9368 Old Sauk Rd Middleton, WI Simply Stunning! Walk into this town home in the Blackhawk Subdivision. This condo inclu...	2 beds \| 1 baths \| 1,260 sq.ft.	$335,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 0.32% Airbnb Rental Income: $1936 Traditional Rental Income: $1286 Airbnb ROI: 0.76% Traditional ROI: 0.32%
9423 White Fox Ln Middleton, WI Desirable ranch home in the heart of Sauk Heights. Four bedrooms, 3 baths with an open fl...	4 beds \| 3 baths \| 2,490 sq.ft.	$674,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 1.7% Airbnb Rental Income: $4740 Traditional Rental Income: $2648 Airbnb ROI: 3.47% Traditional ROI: 1.7%
9420 Stoneywood Blvd 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 Blvd #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%
4473 Shooting Star Avenue Middleton, WI Custom-built home on a private wooded cul-de-sac lot with beautifully landscaped gardens c...	4 beds \| 4 baths \| 5,045 sq.ft.	$1,299,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 1.06% Airbnb Rental Income: $4740 Traditional Rental Income: $3759 Airbnb ROI: 1.06% Traditional ROI: 1.06%
726 Cone Flower St Middleton, WI Welcome Home! This stunning 4 bedroom 3.5 bath sits in a highly desirable Greystone Subdiv...	4 beds \| 3 baths \| 3,130 sq.ft.	$740,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 1.81% Airbnb Rental Income: $4740 Traditional Rental Income: $2938 Airbnb ROI: 3.01% Traditional ROI: 1.81%
3412 Valley Ridge Rd #4 Middleton, WI Cozy yet spacious condo in a quiet Middleton neighborhood. Close to parks, shopping, ente...	3 beds \| 2 baths \| 1,442 sq.ft.	$299,900	Airbnb cash on cash: 5.11% Traditional cash on cash: 2.78% Airbnb Rental Income: $3253 Traditional Rental Income: $1864 Airbnb ROI: 5.11% Traditional ROI: 2.78%
930 Winding Way Middleton, WI Beautiful & bright ranch in Blackhawk in the Middleton schools. Open floor plan features r...	4 beds \| 3 baths \| 4,765 sq.ft.	$1,075,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.84% Airbnb Rental Income: $4740 Traditional Rental Income: $3277 Airbnb ROI: 1.32% Traditional ROI: 0.84%
6235 Charing Cross Ln #A1 Middleton, WI Showings begin Friday 4/30. Incredible Middleton location! Lovely 1 bedroom unit in Chari...	1 beds \| 1 baths \| 760 sq.ft.	$199,900	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.7% Airbnb Rental Income: $1751 Traditional Rental Income: $1059 Airbnb ROI: 1.82% Traditional ROI: 0.7%
5713 Highland Way Middleton, WI Back on the Market, NO Sight Unseen Offers will be presented. This home needs nothing done...	3 beds \| 2 baths \| 1,371 sq.ft.	$470,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 1.84% Airbnb Rental Income: $3253 Traditional Rental Income: $1876 Airbnb ROI: 3.31% Traditional ROI: 1.84%
3324 Glacier Ridge Rd Middleton, WI Showings start FRI 4/8 at 1pm. Wonderful 3 bed, 3.5 bath craftsman home in desirable Middl...	4 beds \| 3 baths \| 3,625 sq.ft.	$1,095,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 0.62% Airbnb Rental Income: $4740 Traditional Rental Income: $2865 Airbnb ROI: 1.5% Traditional ROI: 0.62%
7106 Fortune Dr #7 Middleton, WI Looking for affordable living in Middleton? Come check out this 1st floor corner unit of T...	2 beds \| 1 baths \| 890 sq.ft.	$180,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 2.19% Airbnb Rental Income: $1936 Traditional Rental Income: $1084 Airbnb ROI: 4.18% Traditional ROI: 2.19%
2140 Allen Blvd #3 Middleton, WI Showings start Saturday, 5/21. BEAUTIFUL UPDATED & UPGRADED 2 bedroom, 1 bath move-in read...	2 beds \| 1 baths \| 860 sq.ft.	$189,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.25% Airbnb Rental Income: $1936 Traditional Rental Income: $1129 Airbnb ROI: 2.88% Traditional ROI: 1.25%
9133 Blackhawk Rd Middleton, WI A rare ranch home in prestigious Blackhawk! Beautiful, richly appointed executive home is ...	4 beds \| 4 baths \| 5,135 sq.ft.	$1,400,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.63% Airbnb Rental Income: $4740 Traditional Rental Income: $3558 Airbnb ROI: 0.79% Traditional ROI: 0.63%
1308 Shirley St Middleton, WI Raised Ranch in Woodside Heights. 3 bedroom 2 bath home in the Middleton School District w...	4 beds \| 2 baths \| 2,668 sq.ft.	$599,900	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.01% Airbnb Rental Income: $4740 Traditional Rental Income: $2905 Airbnb ROI: 4.54% Traditional ROI: 3.01%
4029 Serenbe Street Middleton, WI Experience a rare combination of design, efficiency, and low~maintenance living in this mo...	5 beds \| 6 baths \| N/A	$1,599,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 0.42% Airbnb Rental Income: $4368 Traditional Rental Income: $2602 Airbnb ROI: 0.99% Traditional ROI: 0.42%
2914 Hambrecht Rd Middleton, WI 2914 Hambrecht Rd, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 2,300 sq.ft.	$470,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.61% Airbnb Rental Income: $3253 Traditional Rental Income: $2049 Airbnb ROI: 2.69% Traditional ROI: 1.61%
The Everest Plan Middleton, WI The Everest Plan, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,092 sq.ft.	$618,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 0.63% Airbnb Rental Income: $4740 Traditional Rental Income: $2095 Airbnb ROI: 3.52% Traditional ROI: 0.63%
6680 Redpoll Rd Middleton, WI Located in the heart of the highly sought-after Middleton School District, this stunning 4...	4 beds \| 2 baths \| 2,301 sq.ft.	$599,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 1.19% Airbnb Rental Income: $4740 Traditional Rental Income: $2347 Airbnb ROI: 3.71% Traditional ROI: 1.19%
6631 Junco Dr Middleton, WI 6631 Junco Dr, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,205 sq.ft.	$558,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 1.43% Airbnb Rental Income: $4740 Traditional Rental Income: $2342 Airbnb ROI: 4.15% Traditional ROI: 1.43%
The Margot Plan Middleton, WI The Margot Plan, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,404 sq.ft.	$681,300	Airbnb cash on cash: 2.94% Traditional cash on cash: 0.37% Airbnb Rental Income: $4740 Traditional Rental Income: $2130 Airbnb ROI: 2.94% Traditional ROI: 0.37%
The Kennedy Plan Middleton, WI The Kennedy Plan, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,806 sq.ft.	$608,800	Airbnb cash on cash: 1.44% Traditional cash on cash: 0.37% Airbnb Rental Income: $3253 Traditional Rental Income: $1913 Airbnb ROI: 1.44% Traditional ROI: 0.37%
4307 Goldeneye Gateway Dr Middleton, WI 4307 Goldeneye Gateway Dr, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,695 sq.ft.	$473,360	Airbnb cash on cash: 2.65% Traditional cash on cash: 1.73% Airbnb Rental Income: $3253 Traditional Rental Income: $2115 Airbnb ROI: 2.65% Traditional ROI: 1.73%
6654 Redpoll Rd Middleton, WI 6654 Redpoll Rd, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,926 sq.ft.	$556,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 1.38% Airbnb Rental Income: $3253 Traditional Rental Income: $2309 Airbnb ROI: 1.79% Traditional ROI: 1.38%
6655 Redpoll Rd Middleton, WI 6655 Redpoll Rd, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,750 sq.ft.	$509,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 1.35% Airbnb Rental Income: $3253 Traditional Rental Income: $2109 Airbnb ROI: 2.22% Traditional ROI: 1.35%
The Sawyer Plan Middleton, WI The Sawyer Plan, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,879 sq.ft.	$593,600	Airbnb cash on cash: 1.55% Traditional cash on cash: 0.54% Airbnb Rental Income: $3253 Traditional Rental Income: $1964 Airbnb ROI: 1.55% Traditional ROI: 0.54%
4303 Goldeneye Gateway Dr Middleton, WI 4303 Goldeneye Gateway Dr, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,523 sq.ft.	$469,480	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.4% Airbnb Rental Income: $3253 Traditional Rental Income: $1953 Airbnb ROI: 2.69% Traditional ROI: 1.4%
The Hudson Plan Middleton, WI The Hudson Plan, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,172 sq.ft.	$645,200	Airbnb cash on cash: 3.26% Traditional cash on cash: 0.52% Airbnb Rental Income: $4740 Traditional Rental Income: $2115 Airbnb ROI: 3.26% Traditional ROI: 0.52%
4317 Goldeneye Gateway Dr Middleton, WI 4317 Goldeneye Gateway Dr, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,523 sq.ft.	$471,323	Airbnb cash on cash: 2.67% Traditional cash on cash: 1.39% Airbnb Rental Income: $3253 Traditional Rental Income: $1958 Airbnb ROI: 2.67% Traditional ROI: 1.39%
The Emerald Plan Middleton, WI The Emerald Plan, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,650 sq.ft.	$574,700	Airbnb cash on cash: 1.69% Traditional cash on cash: 0.44% Airbnb Rental Income: $3253 Traditional Rental Income: $1849 Airbnb ROI: 1.69% Traditional ROI: 0.44%
The Hoffman Plan Middleton, WI The Hoffman Plan, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,045 sq.ft.	$627,700	Airbnb cash on cash: 3.42% Traditional cash on cash: 0.58% Airbnb Rental Income: $4740 Traditional Rental Income: $2095 Airbnb ROI: 3.42% Traditional ROI: 0.58%
The Beryl Plan Middleton, WI The Beryl Plan, Middleton, WI 53562 \| Single Family Residential	3 beds \| 2 baths \| 1,503 sq.ft.	$553,700	Airbnb cash on cash: 1.86% Traditional cash on cash: 0.43% Airbnb Rental Income: $3253 Traditional Rental Income: $1781 Airbnb ROI: 1.86% Traditional ROI: 0.43%
The Bryant I Plan Middleton, WI The Bryant I Plan, Middleton, WI 53562 \| Single Family Residential	4 beds \| 2 baths \| 2,406 sq.ft.	$676,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 0.39% Airbnb Rental Income: $4740 Traditional Rental Income: $2130 Airbnb ROI: 2.98% Traditional ROI: 0.39%
Lot 31 Belle Farm Middleton, WI Lot 31 Belle Farm, Middleton, WI 53562 \| Other	N/A beds \| N/A baths \| N/A	$246,000	Airbnb cash on cash: 2.58% Traditional cash on cash: -0.77% Airbnb Rental Income: $1844 Traditional Rental Income: $570 Airbnb ROI: 2.58% Traditional ROI: -0.77%
Lot 29 Belle Farm Middleton, WI Lot 29 Belle Farm, Middleton, WI 53562 \| Other	N/A beds \| N/A baths \| N/A	$265,000	Airbnb cash on cash: 2.19% Traditional cash on cash: -0.93% Airbnb Rental Income: $1844 Traditional Rental Income: $567 Airbnb ROI: 2.19% Traditional ROI: -0.93%
Lot 7 Belle Farm Middleton, WI Lot 7 Belle Farm, Middleton, WI 53562 \| Other	N/A beds \| N/A baths \| N/A	$193,000	Airbnb cash on cash: 4.02% Traditional cash on cash: -0.2% Airbnb Rental Income: $1844 Traditional Rental Income: $573 Airbnb ROI: 4.02% Traditional ROI: -0.2%

Vacation Rentals in Middleton

There are 182 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 $228. 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 182 Airbnb properties available for sale in Middleton.

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

In October 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 Ln

Middleton, WI

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

$825,000

Airbnb cash on cash: 2.59%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $4740

Traditional Rental Income: $3001

Airbnb ROI: 2.59%

Traditional ROI: 1.6%

719 Cricket Ln #1

Middleton, WI

3 beds | 2 baths | 1,815 sq.ft.

$349,900

Airbnb cash on cash: 3.25%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $3253

Traditional Rental Income: $2149

Airbnb ROI: 3.25%

Traditional ROI: 2.11%

2809 Century Harbor Rd #3

Middleton, WI

1 beds | 1 baths | 850 sq.ft.

$239,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $1751

Traditional Rental Income: $834

Airbnb ROI: 0.98%

Traditional ROI: -0.94%

7106 Fortune Dr #3

Middleton, WI

2 beds | 1 baths | 870 sq.ft.

$190,000

Airbnb cash on cash: 3.81%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $1936

Traditional Rental Income: $1126

Airbnb ROI: 3.81%

Traditional ROI: 2.16%

9368 Old Sauk Rd

Middleton, WI

2 beds | 1 baths | 1,260 sq.ft.

$335,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $1936

Traditional Rental Income: $1286

Airbnb ROI: 0.76%

Traditional ROI: 0.32%

9423 White Fox Ln

Middleton, WI

4 beds | 3 baths | 2,490 sq.ft.

$674,000

Airbnb cash on cash: 3.47%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $4740

Traditional Rental Income: $2648

Airbnb ROI: 3.47%

Traditional ROI: 1.7%

9420 Stoneywood Blvd

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 Blvd #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%