Real Estate Investment Properties for Sale in Middleton, WI

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

Explore a variety of short-term homes & houses in Middleton, WI. Invest wisely with VRBO & Middleton, 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 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%
4419 Feather Lane Middleton, WI This wonderful Middleton Ridge Smart home could be your next home! It is walking distance ...	3 beds \| 3 baths \| 2,616 sq.ft.	$623,999	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.77% Airbnb Rental Income: $3253 Traditional Rental Income: $2528 Airbnb ROI: 1.76% Traditional ROI: 1.77%
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%
7305 Donna Drive Middleton, WI NEW ROOF 10/26. Enjoy Vibrant Living in this sunny & spacious 2BR/1.5BA plus Lofted den/of...	2 beds \| 2 baths \| 1,548 sq.ft.	$369,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.36% Airbnb Rental Income: $1936 Traditional Rental Income: $1473 Airbnb ROI: 0.22% Traditional ROI: 0.36%
5548 Century Avenue #4 Middleton, WI Conveniently located in Middleton's desirable Rolling Hills Condo Association, this bright...	2 beds \| 2 baths \| 1,080 sq.ft.	$215,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.17% Airbnb Rental Income: $1936 Traditional Rental Income: $1653 Airbnb ROI: 2.04% Traditional ROI: 3.17%
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%
6805 Aldo Leopold Way Middleton, WI Seller is offering a $15,000 closing cost credit for a potential rate buy down. A beautifu...	3 beds \| 4 baths \| 2,665 sq.ft.	$770,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 1.24% Airbnb Rental Income: $3253 Traditional Rental Income: $2756 Airbnb ROI: 0.91% Traditional ROI: 1.24%
7190 Belle Fontaine Boulevard Middleton, WI MRP $575,000-$585,000. Welcome to Misty Valley! Nestled in a desirable Middleton neighborh...	3 beds \| 4 baths \| 2,385 sq.ft.	$575,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.49% Airbnb Rental Income: $3253 Traditional Rental Income: $3249 Airbnb ROI: 2.14% Traditional ROI: 3.49%
707 Cricket Lane #5 Middleton, WI Move right into this end-unit condo in the highly sought-after Middleton School District! ...	2 beds \| 3 baths \| 1,529 sq.ft.	$315,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.77% Airbnb Rental Income: $1936 Traditional Rental Income: $2222 Airbnb ROI: 0.08% Traditional ROI: 2.77%
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%
6833 Phil Lewis Way Middleton, WI RECENTLY UPDATED RED BIRCH FLOORS, NEW ROOF, DECK RAILINGS & MORE! Timeless architecture m...	4 beds \| 5 baths \| 4,656 sq.ft.	$1,399,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.21% Airbnb Rental Income: $4740 Traditional Rental Income: $4521 Airbnb ROI: 0.63% Traditional ROI: 1.21%
10013 Shadow Ridge Trail Middleton, WI VR $1.25M-$1.4M. Live in the Gorgeous Blackhawk Neighborhood with Middleton Schools! One o...	4 beds \| 3 baths \| 3,711 sq.ft.	$1,250,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.92% Airbnb Rental Income: $4740 Traditional Rental Income: $3824 Airbnb ROI: 1.87% Traditional ROI: 1.92%
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%
9395 Old Sauk Road Middleton, WI Elegance and style are showcased in the lovely 3 bed, 2 1/2 bath end unit townhouse condo ...	3 beds \| 3 baths \| 1,683 sq.ft.	$459,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 2.02% Airbnb Rental Income: $3253 Traditional Rental Income: $2591 Airbnb ROI: 1.86% Traditional ROI: 2.02%
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%
6715 S Chickahauk Trail Middleton, WI SELLER-PAID RATE BUYDOWN AVAILABLE! Make this refined, thoughtfully designed home yours! B...	5 beds \| 5 baths \| 4,167 sq.ft.	$1,100,000	Airbnb cash on cash: 1% Traditional cash on cash: 2.2% Airbnb Rental Income: $4368 Traditional Rental Income: $4680 Airbnb ROI: 1% Traditional ROI: 2.2%
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%
6239 Charing Cross Lane #B-2 Middleton, WI PRICE REDUCTION + SELLER INCENTIVES! Seller to pay remaining 2026 monthly condo fees PLUS ...	2 beds \| 2 baths \| 906 sq.ft.	$214,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.4% Airbnb Rental Income: $1936 Traditional Rental Income: $1514 Airbnb ROI: 1.96% Traditional ROI: 2.4%
9715 Red Sky Drive Middleton, WI Nestled in the prestigious Blackhawk neighborhood and located in the highly sought-after M...	5 beds \| 5 baths \| 6,129 sq.ft.	$1,450,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.28% Airbnb Rental Income: $4368 Traditional Rental Income: $4817 Airbnb ROI: 0.27% Traditional ROI: 1.28%
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%

Real Estate investment in Middleton, WI

There are 79 properties for sale in the city of Middleton . The median list price in Middleton is $559,165 and the average price per square foot is $238. In November 2026, the average monthly cash on cash return in Middleton is 1.00%. The average monthly rental income in Middleton is $2,338.

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

There are 79 investment properties available for sale in Middleton.

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

The ROI for Short-Term is higher than the Long-Term in Middleton with average rental income of $3,253.

Your search for investment property begins and ends here

Investment Property 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%

4419 Feather Lane

Middleton, WI

3 beds | 3 baths | 2,616 sq.ft.

$623,999

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.77%

Airbnb Rental Income: $3253

Traditional Rental Income: $2528

Airbnb ROI: 1.76%

Traditional ROI: 1.77%

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%

7305 Donna Drive

Middleton, WI

2 beds | 2 baths | 1,548 sq.ft.

$369,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $1936

Traditional Rental Income: $1473

Airbnb ROI: 0.22%

Traditional ROI: 0.36%

5548 Century Avenue #4

Middleton, WI

2 beds | 2 baths | 1,080 sq.ft.

$215,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $1936

Traditional Rental Income: $1653

Airbnb ROI: 2.04%

Traditional ROI: 3.17%

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%