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
5220 Frisco Court Middleton, WI Light-filled end unit townhouse-style condo could be yours! Large open concept living spac...	2 beds \| 3 baths \| 1,150 sq.ft.	$309,900	Airbnb cash on cash: 3.14% Traditional cash on cash: 4.21% Airbnb Rental Income: $2152 Traditional Rental Income: $1916 Airbnb ROI: 3.14% Traditional ROI: 4.21%
7010 Donna Drive Middleton, WI Your search is over! Charming 4BR/2.5BA ranch home in a highly desirable Middleton neighbo...	4 beds \| 3 baths \| 2,058 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $3134 Airbnb ROI: N/A Traditional ROI: 3.34%
2146 Allen Boulevard #1 Middleton, WI Welcome to your condo in the beautiful neighborhood of Middleton **Charming Lakeside Condo...	2 beds \| 1 baths \| 820 sq.ft.	$200,000	Airbnb cash on cash: 5.74% Traditional cash on cash: 4.16% Airbnb Rental Income: $2152 Traditional Rental Income: $1305 Airbnb ROI: 5.74% Traditional ROI: 4.16%
9332 Spirit Street Middleton, WI Middleton Schools including Pope Farm Elementary! Wonderful, 3 bedroom, 3.5 bath home on a...	3 beds \| 4 baths \| 2,724 sq.ft.	$659,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 2.35% Airbnb Rental Income: $6898 Traditional Rental Income: $3090 Airbnb ROI: 6.37% Traditional ROI: 2.35%
4602 Deerpath Road Middleton, WI Mid-century modern raised ranch located on a large, mature 0.9 acre lot in the highly soug...	4 beds \| 2 baths \| 2,717 sq.ft.	$849,900	Airbnb cash on cash: 6.4% Traditional cash on cash: 1.41% Airbnb Rental Income: $8221 Traditional Rental Income: $2712 Airbnb ROI: 6.4% Traditional ROI: 1.41%
6712 Aldo Leopold Way Middleton, WI Inspired by FLW & rich in Prairie School design, this stunning 3 bed 3.5 bath showcases hi...	3 beds \| 4 baths \| 3,034 sq.ft.	$940,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 1.32% Airbnb Rental Income: $6898 Traditional Rental Income: $3145 Airbnb ROI: 4.08% Traditional ROI: 1.32%
6251 Charing Cross Lane #A Middleton, WI This thoughtfully updated 1-bedroom, 1-bathroom condo offers a prime location near UW, Lak...	1 beds \| 1 baths \| 850 sq.ft.	$169,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 4.37% Airbnb Rental Income: $2498 Traditional Rental Income: $1159 Airbnb ROI: 8.9% Traditional ROI: 4.37%
6633 S Chickahauk Trail Middleton, WI Stunning 3 Bed/3 Bath Middleton Townhome at The Ridges of Pheasant Branch, $400/mo HOA. Se...	3 beds \| 3 baths \| 2,333 sq.ft.	$522,500	Airbnb cash on cash: 8.72% Traditional cash on cash: 3% Airbnb Rental Income: $6898 Traditional Rental Income: $2763 Airbnb ROI: 8.72% Traditional ROI: 3%
9924 Shining Willow Street Middleton, WI NEW CONSTRUCTION - CUSTOM HOME. Photos are examples of a custom ranch home that could be b...	3 beds \| 2 baths \| 1,890 sq.ft.	$749,900	Airbnb cash on cash: 6.42% Traditional cash on cash: 1.89% Airbnb Rental Income: $6898 Traditional Rental Income: $2398 Airbnb ROI: 6.42% Traditional ROI: 1.89%
5320 MAGDALENE Court Middleton, WI New construction, Move in Ready! 3 Bedroom Ranch in Waunakee Schools. Corner lot! Large ...	3 beds \| 2 baths \| 1,842 sq.ft.	$609,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 2.75% Airbnb Rental Income: $6898 Traditional Rental Income: $2413 Airbnb ROI: 8.29% Traditional ROI: 2.75%
8916 Red Beryl Drive Middleton, WI Nestled in Middleton Hidden Oaks neighborhood, this stunning 3-bed/2.5-bath, 1507 sqft 2-s...	3 beds \| 3 baths \| 1,507 sq.ft.	$533,600	Airbnb cash on cash: 8.7% Traditional cash on cash: 2.09% Airbnb Rental Income: $6898 Traditional Rental Income: $2266 Airbnb ROI: 8.7% Traditional ROI: 2.09%
2141 Middleton Beach Road Middleton, WI Exquisite lake home completely remodeled - de Giulio designed kitchen & baths w/high-quali...	3 beds \| 3 baths \| 2,908 sq.ft.	$2,200,000	Airbnb cash on cash: 0.56% Traditional cash on cash: -0.59% Airbnb Rental Income: $6898 Traditional Rental Income: $3214 Airbnb ROI: 0.56% Traditional ROI: -0.59%
4622 Rocky Dell Road Middleton, WI Endless possibilities await for this rare find of nearly 10 acres in the Town of Middleton...	4 beds \| 1 baths \| 2,565 sq.ft.	$1,125,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 0.3% Airbnb Rental Income: $8221 Traditional Rental Income: $2177 Airbnb ROI: 4.58% Traditional ROI: 0.3%
5615 Mendota Drive Middleton, WI Lakefront living on Lake Mendota, Dane County's largest, most popular and sought after lak...	4 beds \| 4 baths \| 3,719 sq.ft.	$1,699,000	Airbnb cash on cash: 1.78% Traditional cash on cash: -0.06% Airbnb Rental Income: $8221 Traditional Rental Income: $3768 Airbnb ROI: 1.78% Traditional ROI: -0.06%
3717 High Road Middleton, WI Welcome to this charming bi-level home in the heart of Middleton, Wisconsin! Featuring 3 b...	3 beds \| 3 baths \| 1,550 sq.ft.	$499,500	Airbnb cash on cash: 9.67% Traditional cash on cash: 2.58% Airbnb Rental Income: $6898 Traditional Rental Income: $2250 Airbnb ROI: 9.67% Traditional ROI: 2.58%
9922 Autumn Breeze Road Middleton, WI Stunning 4-bed home w/stylish design, blends modern elegance w/comfort in peaceful Autumn ...	4 beds \| 4 baths \| 3,036 sq.ft.	$799,000	Airbnb cash on cash: 6.34% Traditional cash on cash: 1.93% Airbnb Rental Income: $8221 Traditional Rental Income: $3378 Airbnb ROI: 6.34% Traditional ROI: 1.93%
640 Burnt Sienna Drive Middleton, WI Back on the market through no fault of Seller, don't miss it! Pristine stand-alone home in...	2 beds \| 2 baths \| 1,222 sq.ft.	$448,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.5% Airbnb Rental Income: $2152 Traditional Rental Income: $2053 Airbnb ROI: 0.43% Traditional ROI: 1.5%
3438 Nappe Drive #3438 Middleton, WI Welcome to this inviting end-unit condominium at Bishops Bay, w/ a spacious entry & versat...	3 beds \| 3 baths \| 2,184 sq.ft.	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $2717 Airbnb ROI: N/A Traditional ROI: 2.2%
4059 Serenbe Street Middleton, WI Price estimate $1,900,000. Build this home on Lot 20 in the beautiful new Belle Farm neigh...	5 beds \| N/A baths \| N/A	$1,900,000	Airbnb cash on cash: 2.76% Traditional cash on cash: -0.26% Airbnb Rental Income: $12188 Traditional Rental Income: $4647 Airbnb ROI: 2.76% Traditional ROI: -0.26%
4600 Plantation Court Middleton, WI REDUCED! A true masterpiece! Immaculate 4BR/3.5BA executive ranch on super private 1+ acre...	4 beds \| 4 baths \| 3,798 sq.ft.	$999,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 1.83% Airbnb Rental Income: $8221 Traditional Rental Income: $3577 Airbnb ROI: 5.15% Traditional ROI: 1.83%
5819 Woodcreek Lane Middleton, WI Discover your ideal home in Woodcreek Village with this charming 2-bedroom, 2-bath condo o...	2 beds \| 2 baths \| 2,127 sq.ft.	$399,700	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.84% Airbnb Rental Income: $2152 Traditional Rental Income: $2399 Airbnb ROI: 1.72% Traditional ROI: 3.84%
3311 Valley Creek Circle Middleton, WI Immaculate, Middleton Woodcreek Village ranch condo!! Renovated & tastefully decorated 2 b...	2 beds \| 2 baths \| 2,099 sq.ft.	$524,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.65% Airbnb Rental Income: $null Traditional Rental Income: $2404 Airbnb ROI: N/A Traditional ROI: 2.65%
7249 Lily Lane Middleton, WI Welcome to your dream ranch-style condo in the highly sought-after Crane's Nest Associatio...	4 beds \| 3 baths \| 3,391 sq.ft.	$825,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 1.44% Airbnb Rental Income: $8221 Traditional Rental Income: $3037 Airbnb ROI: 6.16% Traditional ROI: 1.44%
7223 Fortune Drive Middleton, WI Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom ranch home nestled in the h...	3 beds \| 3 baths \| 2,351 sq.ft.	$495,000	Airbnb cash on cash: 9.79% Traditional cash on cash: 3.77% Airbnb Rental Income: $6898 Traditional Rental Income: $2772 Airbnb ROI: 9.79% Traditional ROI: 3.77%
3226 Creek View Drive #7 Middleton, WI Idyllic condo beaming with natural sunlight & elevated views of the Pheasant Branch Nature...	2 beds \| 2 baths \| 1,464 sq.ft.	$319,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 4.32% Airbnb Rental Income: $2152 Traditional Rental Income: $1992 Airbnb ROI: 3.03% Traditional ROI: 4.32%
7029 Elmwood Avenue Middleton, WI Showings start 10/25. Welcome home to this delightful 4-bedroom Cape Cod nestled right in ...	4 beds \| 2 baths \| 2,003 sq.ft.	$599,900	Airbnb cash on cash: 9.47% Traditional cash on cash: 1.98% Airbnb Rental Income: $8221 Traditional Rental Income: $2468 Airbnb ROI: 9.47% Traditional ROI: 1.98%
4028 Serenbe Street Middleton, WI Who says you cannot live beautifully on a smaller footprint? Build this Shotgun Home on Lo...	2 beds \| 3 baths \| 1,282 sq.ft.	$735,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.3% Airbnb Rental Income: $2152 Traditional Rental Income: $2246 Airbnb ROI: -0.63% Traditional ROI: 0.3%

Real Estate investment in Middleton, WI

There are 27 properties for sale in the city of Middleton . The median list price in Middleton is $533,600 and the average price per square foot is $243. In November 2024, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,496.

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

There are 27 investment properties available for sale in Middleton.

In 2024, 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 $6,898.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, WI

5220 Frisco Court

Middleton, WI

2 beds | 3 baths | 1,150 sq.ft.

$309,900

Airbnb cash on cash: 3.14%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $2152

Traditional Rental Income: $1916

Airbnb ROI: 3.14%

Traditional ROI: 4.21%

7010 Donna Drive

Middleton, WI

4 beds | 3 baths | 2,058 sq.ft.

$580,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $3134

Airbnb ROI: N/A

Traditional ROI: 3.34%

2146 Allen Boulevard #1

Middleton, WI

2 beds | 1 baths | 820 sq.ft.

$200,000

Airbnb cash on cash: 5.74%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $2152

Traditional Rental Income: $1305

Airbnb ROI: 5.74%

Traditional ROI: 4.16%

9332 Spirit Street

Middleton, WI

3 beds | 4 baths | 2,724 sq.ft.

$659,900

Airbnb cash on cash: 6.37%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $6898

Traditional Rental Income: $3090

Airbnb ROI: 6.37%

Traditional ROI: 2.35%

4602 Deerpath Road

Middleton, WI

4 beds | 2 baths | 2,717 sq.ft.

$849,900

Airbnb cash on cash: 6.4%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $8221

Traditional Rental Income: $2712

Airbnb ROI: 6.4%

Traditional ROI: 1.41%

6712 Aldo Leopold Way

Middleton, WI

3 beds | 4 baths | 3,034 sq.ft.

$940,000

Airbnb cash on cash: 4.08%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $6898

Traditional Rental Income: $3145

Airbnb ROI: 4.08%

Traditional ROI: 1.32%

6251 Charing Cross Lane #A

Middleton, WI

1 beds | 1 baths | 850 sq.ft.

$169,900

Airbnb cash on cash: 8.9%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $2498

Traditional Rental Income: $1159

Airbnb ROI: 8.9%

Traditional ROI: 4.37%

6633 S Chickahauk Trail

Middleton, WI

3 beds | 3 baths | 2,333 sq.ft.

$522,500

Airbnb cash on cash: 8.72%

Traditional cash on cash: 3%

Airbnb Rental Income: $6898

Traditional Rental Income: $2763

Airbnb ROI: 8.72%