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
9333 Cobalt Street Middleton, WI Show 9/19. Beautiful home built by Heffron Homes in the Middleton School District! Bright,...	4 beds \| 4 baths \| 3,019 sq.ft.	$774,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 2.2% Airbnb Rental Income: $5748 Traditional Rental Income: $3505 Airbnb ROI: 3.71% Traditional ROI: 2.2%
5029 St Cyr Road Middleton, WI Exceptional custom-built lakefront home showcasing impeccable design + craftsmanship thru-...	4 beds \| 5 baths \| 5,494 sq.ft.	$3,500,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.39% Airbnb Rental Income: $5748 Traditional Rental Income: $5075 Airbnb ROI: -0.54% Traditional ROI: -0.39%
1030 Rooster Run Middleton, WI Enjoy maintenance free living! Rare opportunity to own this beautiful 3 BR, 2 Bath condo w...	3 beds \| 3 baths \| 2,474 sq.ft.	$599,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.48% Airbnb Rental Income: $2540 Traditional Rental Income: $2779 Airbnb ROI: 0.96% Traditional ROI: 2.48%
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.	$605,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 2.84% Airbnb Rental Income: $5748 Traditional Rental Income: $2976 Airbnb ROI: 5.72% Traditional ROI: 2.84%
2564 Branch Street #12 Middleton, WI Affordability can be found still!! Walking distance to Pheasant Branch Trail, near Pheasan...	2 beds \| 1 baths \| 960 sq.ft.	$170,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 5.51% Airbnb Rental Income: $1567 Traditional Rental Income: $1350 Airbnb ROI: 4.07% Traditional ROI: 5.51%
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.	$579,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 2.96% Airbnb Rental Income: $5748 Traditional Rental Income: $3095 Airbnb ROI: 5.75% Traditional ROI: 2.96%
8916 Red Beryl Drive Middleton, WI Beautifully designed Middleton home in the desirable Hidden Oaks neighborhood, ideally loc...	3 beds \| 3 baths \| 1,507 sq.ft.	$526,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.92% Airbnb Rental Income: $2540 Traditional Rental Income: $2266 Airbnb ROI: 1.23% Traditional ROI: 1.92%
7009 Fortune Drive Middleton, WI Peaceful 3-Bedroom Condo Near Downtown Middleton & Madison Welcome to your serene retreat ...	3 beds \| 2 baths \| 1,390 sq.ft.	$340,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 5.53% Airbnb Rental Income: $2540 Traditional Rental Income: $2523 Airbnb ROI: 3.66% Traditional ROI: 5.53%
9121 Blackhawk Road Middleton, WI Expansive ranch home in the popular Blackhawk neighborhood and Middleton school district! ...	5 beds \| 5 baths \| 4,980 sq.ft.	$999,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 3.02% Airbnb Rental Income: $5347 Traditional Rental Income: $5242 Airbnb ROI: 1.97% Traditional ROI: 3.02%
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.	$949,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 1.85% Airbnb Rental Income: $5347 Traditional Rental Income: $3820 Airbnb ROI: 2.36% Traditional ROI: 1.85%
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.	$1,225,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 0.7% Airbnb Rental Income: $5748 Traditional Rental Income: $2943 Airbnb ROI: 2.16% Traditional ROI: 0.7%
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: 3.85% Traditional cash on cash: 3.29% Airbnb Rental Income: $5347 Traditional Rental Income: $3890 Airbnb ROI: 3.85% Traditional ROI: 3.29%
4029 Serenbe Street Middleton, WI New construction in Belle Farm, Middletonâs eco~conscious, walkable community, designed ...	5 beds \| 6 baths \| 3,543 sq.ft.	$1,799,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -1.34% Airbnb Rental Income: $5347 Traditional Rental Income: $2602 Airbnb ROI: -0.34% Traditional ROI: -1.34%
7122 Mockingbird Lane Middleton, WI $25,000 price improvement for a quick sale! Roomy 4 bedroom (plus office/den) Middleton Ho...	4 beds \| 3 baths \| 2,830 sq.ft.	$500,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.82% Airbnb Rental Income: $5748 Traditional Rental Income: $3111 Airbnb ROI: 7.01% Traditional ROI: 3.82%
4043 Serenbe Street Middleton, WI Inspired by coastal gems, this two~unit contemporary cottage in the new Belle Farm neighbo...	5 beds \| 5 baths \| 3,643 sq.ft.	$1,850,000	Airbnb cash on cash: -0.41% Traditional cash on cash: -0.21% Airbnb Rental Income: $5347 Traditional Rental Income: $4607 Airbnb ROI: -0.41% Traditional ROI: -0.21%
4865 Champions Run Middleton, WI Rarely available in prestigious Bridle Ridge, this Executive 5-bedroom, 4-bath, 4-car heat...	5 beds \| 4 baths \| 5,000 sq.ft.	$1,460,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.67% Airbnb Rental Income: $5347 Traditional Rental Income: $3718 Airbnb ROI: 1.07% Traditional ROI: 0.67%
6833 Phil Lewis Way Middleton, WI This exceptional Middleton Hills home offers architectural character, modern convenience, ...	4 beds \| 5 baths \| 4,656 sq.ft.	$1,499,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.23% Airbnb Rental Income: $5748 Traditional Rental Income: $4521 Airbnb ROI: 1.29% Traditional ROI: 1.23%
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.	$1,399,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.23% Airbnb Rental Income: $5748 Traditional Rental Income: $3899 Airbnb ROI: 0.77% Traditional ROI: 0.23%
4924 Champions Run Middleton, WI Beautiful stone home with expansive views of the 1.59 acre gorgeous yard. Two story cathed...	5 beds \| 5 baths \| 4,838 sq.ft.	$1,400,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 1.71% Airbnb Rental Income: $5347 Traditional Rental Income: $4932 Airbnb ROI: 1.2% Traditional ROI: 1.71%
2814 Pleasant View Road #202 Middleton, WI Welcome home! Tucked away on the edge of Middleton and right across from Firefighterâs M...	2 beds \| 1 baths \| 998 sq.ft.	$249,900	Airbnb cash on cash: 2.17% Traditional cash on cash: 4.09% Airbnb Rental Income: $1567 Traditional Rental Income: $1571 Airbnb ROI: 2.17% Traditional ROI: 4.09%
3114 Creek View Drive #4 Middleton, WI Welcome to Harbor Village! This inviting 2nd fl end unit condo has a lot to offer in 1500+...	2 beds \| 2 baths \| 1,510 sq.ft.	$315,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.28% Airbnb Rental Income: $1567 Traditional Rental Income: $1977 Airbnb ROI: 1.37% Traditional ROI: 4.28%
6988 Schneider Road Middleton, WI First time offered! Historic 19th century 6.25-acre farmette 6.25-acre6 +/- sqft, 2-story ...	5 beds \| 4 baths \| 3,186 sq.ft.	$1,099,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 0.71% Airbnb Rental Income: $5347 Traditional Rental Income: $2602 Airbnb ROI: 2.34% Traditional ROI: 0.71%
2911 Marina Drive Middleton, WI Step inside this zero lot line duplex with NO CONDO FEE to this fully updated townhouse in...	3 beds \| 3 baths \| 1,832 sq.ft.	$399,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 4.27% Airbnb Rental Income: $2540 Traditional Rental Income: $2467 Airbnb ROI: 2.83% Traditional ROI: 4.27%
3716 Lexington Circle Middleton, WI Rare second chance! Tucked away on a quiet cul-de-sac, this beautifully cared-for property...	3 beds \| 3 baths \| 3,275 sq.ft.	$700,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.81% Airbnb Rental Income: $2540 Traditional Rental Income: $2763 Airbnb ROI: 0.53% Traditional ROI: 1.81%
3108 Creek View Drive #7 Middleton, WI Discover your dream home in Middleton, Wisconsin! This stunning 2nd-floor, end unitÂ offer...	2 beds \| 2 baths \| 1,468 sq.ft.	$314,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.1% Airbnb Rental Income: $1567 Traditional Rental Income: $1911 Airbnb ROI: 1.42% Traditional ROI: 4.1%
6205 Mendota Avenue Middleton, WI Ranch has Lake Mendota/Marshall Park (boat launch) a few hundred yards East & Lakeview Par...	4 beds \| 2 baths \| 1,440 sq.ft.	$534,900	Airbnb cash on cash: 6.87% Traditional cash on cash: 2.08% Airbnb Rental Income: $5748 Traditional Rental Income: $2204 Airbnb ROI: 6.87% Traditional ROI: 2.08%
5511 Mendota Drive Middleton, WI Discover exceptional Lake living in Middleton with unobstructed water views of Lake Mendot...	4 beds \| 4 baths \| 4,246 sq.ft.	$2,400,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -0.23% Airbnb Rental Income: $5748 Traditional Rental Income: $4125 Airbnb ROI: -0.02% Traditional ROI: -0.23%
9435 Spirit Street Middleton, WI This beautifully maintained home stands out with thoughtful details, warm character, and a...	4 beds \| 4 baths \| 2,508 sq.ft.	$599,999	Airbnb cash on cash: 5.41% Traditional cash on cash: 2.69% Airbnb Rental Income: $5748 Traditional Rental Income: $3074 Airbnb ROI: 5.41% Traditional ROI: 2.69%
661 Burnt Sienna Drive Middleton, WI Charming & spacious cottage-style home in meticulous condition minutes from Junction Road ...	3 beds \| 3 baths \| 1,875 sq.ft.	$517,500	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.11% Airbnb Rental Income: $2540 Traditional Rental Income: $2810 Airbnb ROI: 1.28% Traditional ROI: 3.11%

Real Estate investment in Middleton, WI

There are 39 properties for sale in the city of Middleton . The median list price in Middleton is $605,000 and the average price per square foot is $218. In November 2025, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,903.

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

There are 39 investment properties available for sale in Middleton.

In 2025, 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 $5,347.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, WI

9333 Cobalt Street

Middleton, WI

4 beds | 4 baths | 3,019 sq.ft.

$774,900

Airbnb cash on cash: 3.71%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $5748

Traditional Rental Income: $3505

Airbnb ROI: 3.71%

Traditional ROI: 2.2%

5029 St Cyr Road

Middleton, WI

4 beds | 5 baths | 5,494 sq.ft.

$3,500,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: -0.39%

Airbnb Rental Income: $5748

Traditional Rental Income: $5075

Airbnb ROI: -0.54%

Traditional ROI: -0.39%

1030 Rooster Run

Middleton, WI

3 beds | 3 baths | 2,474 sq.ft.

$599,900

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2540

Traditional Rental Income: $2779

Airbnb ROI: 0.96%

Traditional ROI: 2.48%

7013 Cardinal Drive

Middleton, WI

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

$605,000

Airbnb cash on cash: 5.72%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $5748

Traditional Rental Income: $2976

Airbnb ROI: 5.72%

Traditional ROI: 2.84%

2564 Branch Street #12

Middleton, WI

2 beds | 1 baths | 960 sq.ft.

$170,000

Airbnb cash on cash: 4.07%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $1567

Traditional Rental Income: $1350

Airbnb ROI: 4.07%

Traditional ROI: 5.51%

8903 White Coral Way

Middleton, WI

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

$579,000

Airbnb cash on cash: 5.75%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $5748

Traditional Rental Income: $3095

Airbnb ROI: 5.75%

Traditional ROI: 2.96%

8916 Red Beryl Drive

Middleton, WI

3 beds | 3 baths | 1,507 sq.ft.

$526,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $2540

Traditional Rental Income: $2266

Airbnb ROI: 1.23%

Traditional ROI: 1.92%

7009 Fortune Drive

Middleton, WI

3 beds | 2 baths | 1,390 sq.ft.

$340,000

Airbnb cash on cash: 3.66%

Traditional cash on cash: 5.53%

Airbnb Rental Income: $2540

Traditional Rental Income: $2523

Airbnb ROI: 3.66%