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: 1.14%
|
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. |
$1,799,000 |
Airbnb cash on cash: -0.97%
|
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: -0.03%
|
5715 Sandhill DriveMiddleton, WIThoughtfully designed for both daily ease and entertaining, this home is anchored by a wel... |
4 beds | 4 baths | 3,772 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.63%
|
9913 Autumn Breeze RoadMiddleton, WIBeautiful 3-bedroom, 2.5-bath two-story transitional home featuring a spacious open-concep... |
3 beds | 3 baths | 1,714 sq.ft. |
$588,000 |
Airbnb cash on cash: 0.49%
|
6410 Lakeview BoulevardMiddleton, WISome houses are just well-situated. This Middleton ranch is a short walk from Lakeview Par... |
3 beds | 2 baths | 1,454 sq.ft. |
$475,000 |
Airbnb cash on cash: 1.61%
|
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: -1.02%
|
4029 Serenbe StreetMiddleton, WIExperience a rare combination of design, efficiency, and low-maintenance living in this mo... |
5 beds | N/A baths | N/A |
$1,749,000 |
Airbnb cash on cash: -0.02%
|
4043 Serenbe StreetMiddleton, WIA 2025 Parade Home showcasing contemporary design and abundant natural light in Belle Farm... |
5 beds | N/A baths | N/A |
$1,799,000 |
Airbnb cash on cash: -0.03%
|
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: -0.43%
|
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: 2.3%
|
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: 1.08%
|
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: -1.73%
|
6741 Frank Lloyd Wright Avenue #200Middleton, WISunny, bright END unit w/high ceilings & exposed beams and ductwork. Open concept allows y... |
1 beds | 1 baths | 950 sq.ft. |
$364,900 |
Airbnb cash on cash: -0.33%
|
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%
|
10013 Shadow Ridge TrailMiddleton, WIVRP $1,500,000-$1,650,000. Dig ready Southwest Transitional in Blackhawk! No detail spared... |
4 beds | 4 baths | 4,068 sq.ft. |
$1,500,000 |
Airbnb cash on cash: 0.44%
|
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. |
$473,900 |
Airbnb cash on cash: 0.89%
|
9106 Waterside StreetMiddleton, WIMaintenance-free living meets single-family privacy! This stunning duplex-style condo is m... |
4 beds | 3 baths | 2,611 sq.ft. |
$549,900 |
Airbnb cash on cash: 2.01%
|
7135 Johann Farm RoadMiddleton, WIMove-in ready 5/4/26. This Emerald home features a thoughtfully designed, open-concept lay... |
3 beds | 3 baths | 1,647 sq.ft. |
$589,900 |
Airbnb cash on cash: 0.1%
|
5003 Wenlock Rose CourtMiddleton, WIExperience refined living on Bishopâs Bay golf course in this fully renovated condo. Rec... |
3 beds | 3 baths | 2,626 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -0.96%
|
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 |
$960,000 |
Airbnb cash on cash: 0.07%
|
7127 Johann Farm RoadMiddleton, WIMove-in ready 5/19/26. This Beryl home features a thoughtfully designed, open-concept layo... |
3 beds | 3 baths | 1,519 sq.ft. |
$569,900 |
Airbnb cash on cash: 0.2%
|
625 Schewe RoadMiddleton, WIMove-in ready 5/1/26. This Chelsea home features a thoughtfully designed, open-concept lay... |
3 beds | 3 baths | 1,667 sq.ft. |
$432,900 |
Airbnb cash on cash: 1.19%
|
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: 0.65%
|
Real Estate investment in Middleton, WI
There are 68 properties for sale in the city of Middleton . The median list price in Middleton is $549,900 and the average price per square foot is $235. In May 2026, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,587.