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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9420 Stoneywood BoulevardMiddleton, WIWelcome home to this impeccably maintained ranch-style residence that combines comfort, st... |
4 beds | 3 baths | 2,753 sq.ft. |
$651,400 |
Airbnb cash on cash: 2.09%
|
4917 Breakers Rock RoadMiddleton, WISet within the sought-after Community of Bishops Bay, this thoughtfully designed home pair... |
4 beds | 5 baths | 5,704 sq.ft. |
$1,700,000 |
Airbnb cash on cash: -0.6%
|
4473 Shooting Star AvenueMiddleton, WIWelcome to this custom built home w/private wooded lot on a cul-de-sac.The sweeping foyer ... |
4 beds | 4 baths | 5,045 sq.ft. |
$1,299,000 |
Airbnb cash on cash: 0.44%
|
2829 Century Harbor Road #3Middleton, WIThis second-floor one-bedroom condo is located in Century Harbor Condominiums, a desirable... |
1 beds | 1 baths | 850 sq.ft. |
$219,900 |
Airbnb cash on cash: -0.19%
|
8510 Greenway Boulevard #102Middleton, WIEnjoy comfortable, carefree living at Bella Casa Condominiums! This inviting first-floor c... |
1 beds | 1 baths | 923 sq.ft. |
$249,000 |
Airbnb cash on cash: 1.36%
|
5548 Century Avenue #4Middleton, WIConveniently located in Middletonâs desirable Rolling Hills Condo Association, this brig... |
2 beds | 2 baths | 1,080 sq.ft. |
$235,000 |
Airbnb cash on cash: 0.88%
|
707 Cricket Lane #5Middleton, WIWelcome Home ! Welcome to this bright and inviting 2BR, 2.5BA condo located in the desirab... |
2 beds | 3 baths | 1,529 sq.ft. |
$335,000 |
Airbnb cash on cash: -0.3%
|
4029 Serenbe StreetMiddleton, WIExperience a rare combination of design, efficiency, and low-maintenance living in this mo... |
5 beds | N/A baths | N/A |
$1,699,000 |
Airbnb cash on cash: 0.64%
|
4043 Serenbe StreetMiddleton, WIA move~in ready home offering multi~generational and low~maintenance living at Belle Farm.... |
5 beds | N/A baths | N/A |
$1,799,000 |
Airbnb cash on cash: 0.57%
|
6833 Phil Lewis WayMiddleton, WIExperience timeless architecture and modern sophistication in this exceptional Middleton H... |
4 beds | 5 baths | 4,656 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -0.02%
|
2911 Marina DriveMiddleton, WIStep inside this zero lot line duplex with NO CONDO FEE and brand NEW ROOF to a fully upda... |
3 beds | 3 baths | 1,832 sq.ft. |
$389,000 |
Airbnb cash on cash: 1.88%
|
10122 Mosaic WayMiddleton, WIThis Aldo home features a smart, open layout and checks off all your boxes. 3 bedrooms, 2.... |
3 beds | 3 baths | 1,765 sq.ft. |
$444,900 |
Airbnb cash on cash: 0.71%
|
613 Tabby Turn DriveMiddleton, WIThis Astor home features a smart, open layout and checks off all your boxes. 2 bedrooms, 2... |
2 beds | 3 baths | 1,408 sq.ft. |
$409,900 |
Airbnb cash on cash: -1.14%
|
7142 Johann Farm RoadMiddleton, WIThis Sawyer home features a smart, open layout and checks off all your boxes. 3 bedrooms, ... |
3 beds | 3 baths | 1,861 sq.ft. |
$609,900 |
Airbnb cash on cash: -0.27%
|
10013 Shadow Ridge TrailMiddleton, WIVR $1.25M-$1.4M. Live in the Gorgeous Blackhawk Neighborhood with Middleton Schools! One o... |
4 beds | 3 baths | 3,711 sq.ft. |
$1,400,000 |
Airbnb cash on cash: 0.99%
|
9395 Old Sauk RoadMiddleton, WIElegance 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. |
$463,000 |
Airbnb cash on cash: 0.58%
|
620 Tabby Turn DriveMiddleton, WIThis Chelsea home features a thoughtfully designed, open-concept layout ideal for modern l... |
3 beds | 3 baths | 1,519 sq.ft. |
$494,900 |
Airbnb cash on cash: 0.36%
|
7135 Johann Farm RoadMiddleton, WIThis 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: -0.18%
|
1214-1216 N High Point RoadMiddleton, WIExcellent Investment Opportunity in prime Middleton Location!! Well~maintained duplex in t... |
6 beds | N/A baths | N/A |
$899,000 |
Airbnb cash on cash: 1.33%
|
7127 Johann Farm RoadMiddleton, WIThis Beryl home features a thoughtfully designed, open-concept layout ideal for modern liv... |
3 beds | 3 baths | 1,519 sq.ft. |
$569,900 |
Airbnb cash on cash: -0.09%
|
625 Schewe RoadMiddleton, WIThis Chelsea home features a thoughtfully designed, open-concept layout ideal for modern l... |
3 beds | 3 baths | 1,667 sq.ft. |
$432,900 |
Airbnb cash on cash: 0.81%
|
616 Tabby Turn DriveMiddleton, WIThis 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: 0.32%
|
7401 Century Pl #103BMiddleton, WIFresh, modern, and completely turnkey! This beautifully updated Middleton condo features r... |
1 beds | 1 baths | 980 sq.ft. |
$175,000 |
Airbnb cash on cash: 1.27%
|
2809 Dewey CourtMiddleton, WITwo lots create a rare opportunity along a quiet channel with direct access to Lake Mendot... |
3 beds | 2 baths | 1,704 sq.ft. |
$1,000,000 |
Airbnb cash on cash: -0.67%
|
Real Estate investment in Middleton, WI
There are 65 properties for sale in the city of Middleton . The median list price in Middleton is $489,247 and the average price per square foot is $211. In June 2026, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,577.