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
5029 St Cyr Rd Middleton, WI Exceptional custom-built lakefront home showcasing impeccable design + craftsmanship thru-...	4 beds \| 4 baths \| 5,494 sq.ft.	$3,450,000	Airbnb cash on cash: -0.58% Traditional cash on cash: -0.38% Airbnb Rental Income: $5571 Traditional Rental Income: $5075 Airbnb ROI: -0.58% Traditional ROI: -0.38%
8530 Greenway Blvd #101 Middleton, WI Many updates in this bright, cheerful condominium! Wood flooring, updated kitchen with pa...	2 beds \| 1 baths \| 982 sq.ft.	$315,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.44% Airbnb Rental Income: $1344 Traditional Rental Income: $1416 Airbnb ROI: 0.81% Traditional ROI: 2.44%
1030 Rooster Run Middleton, WI PRICE DROP! Stonefield Village ~ Enjoy the privacy of a single-family residence with the c...	3 beds \| 3 baths \| 2,474 sq.ft.	$579,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.55% Airbnb Rental Income: $2171 Traditional Rental Income: $2779 Airbnb ROI: 0.41% Traditional ROI: 2.55%
3114 Creek View Drive #3 Middleton, WI Welcome to Harbor Village in Middleton which borders on the Pheasant Branch Nature Preserv...	2 beds \| 2 baths \| 1,298 sq.ft.	$285,900	Airbnb cash on cash: 1.09% Traditional cash on cash: 4.34% Airbnb Rental Income: $1344 Traditional Rental Income: $1807 Airbnb ROI: 1.09% Traditional ROI: 4.34%
Lot 13 Glacier Forest Ct Middleton, WI This is an example of a luxurious home that can be built on this vacant lot. This home wil...	4 beds \| 4 baths \| 5,500 sq.ft.	$2,750,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.81% Airbnb Rental Income: $3311 Traditional Rental Income: $4728 Airbnb ROI: -0.03% Traditional ROI: 0.81%
4029 Serenbe Street Middleton, WI Price improvement! Welcome to a thoughtfully designed new construction residence in Belle ...	5 beds \| N/A baths \| N/A	$1,749,000	Airbnb cash on cash: -0.22% Traditional cash on cash: -1.3% Airbnb Rental Income: $5452 Traditional Rental Income: $2602 Airbnb ROI: -0.22% Traditional ROI: -1.3%
4043 Serenbe Street Middleton, WI Price improvement! Welcome to an inspired contemporary residence at Belle Farm, where mode...	5 beds \| N/A baths \| N/A	$1,799,000	Airbnb cash on cash: -0.29% Traditional cash on cash: -0.14% Airbnb Rental Income: $5452 Traditional Rental Income: $4607 Airbnb ROI: -0.29% Traditional ROI: -0.14%
3108 Creek View Dr #7 Middleton, WI Discover your dream home in Middleton, Wisconsin! This stunning 2nd-floor, end-unit offers...	2 beds \| 2 baths \| 1,468 sq.ft.	$299,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 4.37% Airbnb Rental Income: $1344 Traditional Rental Income: $1911 Airbnb ROI: 0.89% Traditional ROI: 4.37%
6205 Mendota Ave 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.	$509,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 2.23% Airbnb Rental Income: $5571 Traditional Rental Income: $2204 Airbnb ROI: 6.96% Traditional ROI: 2.23%
5511 Mendota Dr Middleton, WI Discover exceptional Lake living in Middleton with unobstructed water views of Lake Mendot...	4 beds \| 3 baths \| 4,246 sq.ft.	$2,400,000	Airbnb cash on cash: -0.14% Traditional cash on cash: -0.28% Airbnb Rental Income: $5571 Traditional Rental Income: $4125 Airbnb ROI: -0.14% Traditional ROI: -0.28%
3615 John Muir Dr Middleton, WI A nature lover's oasis, backing up to Pheasant Branch Conservancy! From the moment you ste...	5 beds \| 4 baths \| 3,718 sq.ft.	$1,200,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 0.61% Airbnb Rental Income: $5452 Traditional Rental Income: $3546 Airbnb ROI: 1.33% Traditional ROI: 0.61%
3702 Nathan Hale Ct Middleton, WI This 4 bedroom, 2 1/2 bath, 2 story Colonial home has it all! Brand new large kitchen from...	4 beds \| 2 baths \| 2,444 sq.ft.	$649,900	Airbnb cash on cash: 5.08% Traditional cash on cash: 2.53% Airbnb Rental Income: $5571 Traditional Rental Income: $2907 Airbnb ROI: 5.08% Traditional ROI: 2.53%
639 Schewe Rd Middleton, WI Move-in Ready 1/19/26! This Chelsea home features a smart, open layout and checks off all ...	3 beds \| 2 baths \| 1,690 sq.ft.	$424,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.14% Airbnb Rental Income: $2171 Traditional Rental Income: $2485 Airbnb ROI: 0.96% Traditional ROI: 3.14%
613 Tabby Turn Dr Middleton, WI Move-in Ready 1/20/26! This Astor home features a smart, open layout and checks off all yo...	2 beds \| 2 baths \| 1,408 sq.ft.	$409,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 2.78% Airbnb Rental Income: $1344 Traditional Rental Income: $2267 Airbnb ROI: -0.69% Traditional ROI: 2.78%
6829 Cooper Ave Middleton, WI Show 11/7. This charming, light-filled home offers easy single-level living with three bed...	3 beds \| 1 baths \| 1,455 sq.ft.	$449,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.67% Airbnb Rental Income: $2171 Traditional Rental Income: $2136 Airbnb ROI: 1.45% Traditional ROI: 2.67%
6811 Aldo Leopold Way Middleton, WI This Middleton Hills gem blends easy living with classic Craftsman style! Everything you n...	3 beds \| 2 baths \| 2,352 sq.ft.	$800,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.05% Airbnb Rental Income: $2171 Traditional Rental Income: $2761 Airbnb ROI: -0.48% Traditional ROI: 1.05%
7418 Century Avenue Middleton, WI This 6-unit apartment/condo complex offers the perfect blend of convenience and comfort. E...	6 beds \| N/A baths \| N/A	$1,090,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 0.13% Airbnb Rental Income: $5452 Traditional Rental Income: $2385 Airbnb ROI: 2.07% Traditional ROI: 0.13%
624 Tabby Turn Dr Middleton, WI Move-in Ready 2/11/26! This Jade home features a smart, open layout and checks off all you...	3 beds \| 2 baths \| 1,547 sq.ft.	$499,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.05% Airbnb Rental Income: $2171 Traditional Rental Income: $2393 Airbnb ROI: 0.4% Traditional ROI: 2.05%
7142 Johann Farm Rd Middleton, WI Move-in Ready 3/16/26! This Sawyer home features a smart, open layout and checks off all y...	3 beds \| 2 baths \| 1,861 sq.ft.	$609,900	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.57% Airbnb Rental Income: $2171 Traditional Rental Income: $2631 Airbnb ROI: -0.21% Traditional ROI: 1.57%
7131 Johann Farm Rd Middleton, WI Move-in ready 3/23/26. This Hoffman home features a thoughtfully designed, open-concept la...	4 beds \| 2 baths \| 2,033 sq.ft.	$664,900	Airbnb cash on cash: 4.14% Traditional cash on cash: 1.35% Airbnb Rental Income: $5571 Traditional Rental Income: $2719 Airbnb ROI: 4.14% Traditional ROI: 1.35%
7130 Johann Farm Rd Middleton, WI Move-in ready 3/31/26. This Astoria home features a thoughtfully designed, open-concept la...	3 beds \| 2 baths \| 1,649 sq.ft.	$549,900	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.08% Airbnb Rental Income: $2171 Traditional Rental Income: $2137 Airbnb ROI: 0.08% Traditional ROI: 1.08%
7146 Johann Farm Rd Middleton, WI Move-in ready 4/2/26. This Harlow home features a thoughtfully designed, open-concept layo...	3 beds \| 2 baths \| 1,577 sq.ft.	$599,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.94% Airbnb Rental Income: $2171 Traditional Rental Income: $2237 Airbnb ROI: -0.16% Traditional ROI: 0.94%
608 Bear Claw Way Middleton, WI Showing starts January 15 - bright, sunny and spacious townhouse condo in the popular Midd...	3 beds \| 2 baths \| 1,758 sq.ft.	$424,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.55% Airbnb Rental Income: $2171 Traditional Rental Income: $2507 Airbnb ROI: 1.32% Traditional ROI: 3.55%

Real Estate investment in Middleton, WI

There are 40 properties for sale in the city of Middleton . The median list price in Middleton is $539,000 and the average price per square foot is $234. In January 2026, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,458.

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

There are 40 investment properties available for sale in Middleton.

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

The ROI for Long-Term is higher than the Short-Term in Middleton with average rental income of $2,458.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, WI

5029 St Cyr Rd

Middleton, WI

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

$3,450,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $5571

Traditional Rental Income: $5075

Airbnb ROI: -0.58%

Traditional ROI: -0.38%

8530 Greenway Blvd #101

Middleton, WI

2 beds | 1 baths | 982 sq.ft.

$315,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $1344

Traditional Rental Income: $1416

Airbnb ROI: 0.81%

Traditional ROI: 2.44%

1030 Rooster Run

Middleton, WI

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

$579,000

Airbnb cash on cash: 0.41%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $2171

Traditional Rental Income: $2779

Airbnb ROI: 0.41%

Traditional ROI: 2.55%

3114 Creek View Drive #3

Middleton, WI

2 beds | 2 baths | 1,298 sq.ft.

$285,900

Airbnb cash on cash: 1.09%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $1344

Traditional Rental Income: $1807

Airbnb ROI: 1.09%

Traditional ROI: 4.34%

Lot 13 Glacier Forest Ct

Middleton, WI

4 beds | 4 baths | 5,500 sq.ft.

$2,750,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 0.81%

Airbnb Rental Income: $3311

Traditional Rental Income: $4728

Airbnb ROI: -0.03%

Traditional ROI: 0.81%

4029 Serenbe Street

Middleton, WI

5 beds | N/A baths | N/A

$1,749,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: -1.3%

Airbnb Rental Income: $5452

Traditional Rental Income: $2602

Airbnb ROI: -0.22%

Traditional ROI: -1.3%

4043 Serenbe Street

Middleton, WI

5 beds | N/A baths | N/A

$1,799,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $5452

Traditional Rental Income: $4607

Airbnb ROI: -0.29%

Traditional ROI: -0.14%

3108 Creek View Dr #7

Middleton, WI

2 beds | 2 baths | 1,468 sq.ft.

$299,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1344

Traditional Rental Income: $1911

Airbnb ROI: 0.89%