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 |
|---|---|---|---|
5029 St Cyr RoadMiddleton, WIExceptional custom-built lakefront home showcasing impeccable design + craftsmanship thru-... |
4 beds | 5 baths | 5,494 sq.ft. |
$3,450,000 |
Airbnb cash on cash: -0.58%
|
8530 Greenway Boulevard #101Middleton, WIMany 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%
|
1030 Rooster RunMiddleton, WIMAJOR PRICE DROP! Enjoy the privacy of a single-family residence with the convenience of c... |
3 beds | 3 baths | 2,474 sq.ft. |
$585,000 |
Airbnb cash on cash: 0.39%
|
3114 Creek View Drive #3Middleton, WIWelcome 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%
|
7009 Fortune DriveMiddleton, WIPeaceful 3-Bedroom Condo Near Downtown Middleton & Madison Welcome to your serene retreat ... |
3 beds | 2 baths | 1,390 sq.ft. |
$335,000 |
Airbnb cash on cash: 2.75%
|
4029 Serenbe StreetMiddleton, WICharm meets new construction at Belle Farm, Middletonâs sustainable, health & wellness c... |
5 beds | N/A baths | N/A |
$1,799,000 |
Airbnb cash on cash: -0.29%
|
4043 Serenbe StreetMiddleton, WIInspired by coastal gems, this move~in ready contemporary home at Belle Farm blends a sens... |
5 beds | N/A baths | N/A |
$1,850,000 |
Airbnb cash on cash: -0.36%
|
6833 Phil Lewis WayMiddleton, WIThis exceptional Middleton Hills home offers architectural character, modern convenience, ... |
4 beds | 5 baths | 4,656 sq.ft. |
$1,499,000 |
Airbnb cash on cash: 1.18%
|
3114 Creek View Drive #4Middleton, WIWelcome to Harbor Village! Inviting 2nd fl end unit condo has a lot to offer in 1500+ sq f... |
2 beds | 2 baths | 1,510 sq.ft. |
$299,000 |
Airbnb cash on cash: 0.79%
|
3716 Lexington CircleMiddleton, WIRare second chance! Tucked away on a quiet cul-de-sac, this beautifully cared-for property... |
4 beds | 3 baths | 3,275 sq.ft. |
$685,000 |
Airbnb cash on cash: 4.52%
|
3108 Creek View Drive #7Middleton, WIDiscover your dream home in Middleton, Wisconsin! This stunning 2nd-floor, end unit offer... |
2 beds | 2 baths | 1,468 sq.ft. |
$309,900 |
Airbnb cash on cash: 0.82%
|
6205 Mendota AvenueMiddleton, WIRanch 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%
|
5511 Mendota DriveMiddleton, WIDiscover 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: -0.14%
|
5805 Roosevelt StreetMiddleton, WILocation, location, location! This home is not only just a block from Lake Mendota, but it... |
2 beds | 1 baths | 864 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.61%
|
10122 Mosaic WayMiddleton, WIMove-in Ready 1/6/26! This Aldo home features a smart, open layout and checks off all your... |
3 beds | 3 baths | 1,891 sq.ft. |
$444,900 |
Airbnb cash on cash: 0.79%
|
3615 John Muir DriveMiddleton, WIA 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%
|
3702 Nathan Hale CourtMiddleton, WIThis 4 bedroom, 2 1/2 bath, 2 story Colonial home has it all! Brand new large kitchen from... |
4 beds | 3 baths | 2,444 sq.ft. |
$649,900 |
Airbnb cash on cash: 5.08%
|
639 Schewe RoadMiddleton, WIMove-in Ready 1/13/26! This Chelsea home features a smart, open layout and checks off all ... |
3 beds | 3 baths | 1,690 sq.ft. |
$424,900 |
Airbnb cash on cash: 0.96%
|
709 Cricket Lane #2Middleton, WIAn affordable opportunity to own a low-maintenance home in the Middleton School District. ... |
2 beds | 3 baths | 1,520 sq.ft. |
$323,000 |
Airbnb cash on cash: 0.21%
|
6251 Charing Cross Lane #DMiddleton, WILots to love in this renovated 2bd Middleton condo! The main living area (living, dining,... |
2 beds | 2 baths | 862 sq.ft. |
$245,000 |
Airbnb cash on cash: 1.72%
|
613 Tabby Turn DriveMiddleton, WIMove-in Ready 1/20/26! This Astor home features a smart, open layout and checks off all yo... |
2 beds | 3 baths | 1,408 sq.ft. |
$409,900 |
Airbnb cash on cash: -0.69%
|
6829 Cooper AvenueMiddleton, WIShow 11/7. This charming, light-filled home offers easy single-level living with three bed... |
3 beds | 2 baths | 1,455 sq.ft. |
$449,900 |
Airbnb cash on cash: 1.45%
|
6811 Aldo Leopold WayMiddleton, WIThis Middleton Hills gem blends easy living with classic Craftsman style! Everything you n... |
3 beds | 3 baths | 2,352 sq.ft. |
$820,000 |
Airbnb cash on cash: -0.49%
|
7418 Century AvenueMiddleton, WIThis 6-unit apartment\condo complex offers the perfect blend of convenience and comfort. E... |
6 beds | N/A baths | N/A |
$1,185,000 |
Airbnb cash on cash: 1.83%
|
9329 Cobalt StreetMiddleton, WIWelcome to this high-quality 2 bedroom, 2 bathroom home offering an inviting open-concept ... |
2 beds | 2 baths | 1,533 sq.ft. |
$499,900 |
Airbnb cash on cash: -0.98%
|
624 Tabby Turn DriveMiddleton, WIMove-in Ready 2/11/26! This Jade home features a smart, open layout and checks off all you... |
3 beds | 3 baths | 1,547 sq.ft. |
$499,900 |
Airbnb cash on cash: 0.4%
|
7142 Johann Farm RoadMiddleton, WIMove-in Ready 3/16/26! This Sawyer home features a smart, open layout and checks off all y... |
3 beds | 3 baths | 1,861 sq.ft. |
$609,900 |
Airbnb cash on cash: -0.21%
|
7134 Johann Farm RoadMiddleton, WIMove-in Ready 3/20/26! This Harlequin home features a smart, open layout and checks off al... |
3 beds | 3 baths | 1,568 sq.ft. |
$539,900 |
Airbnb cash on cash: 0.13%
|
Real Estate investment in Middleton, WI
There are 37 properties for sale in the city of Middleton . The median list price in Middleton is $509,000 and the average price per square foot is $234. In December 2025, the average monthly cash on cash return in Middleton is 2.00%. The average monthly rental income in Middleton is $2,472.