Real Estate Investment Properties for Sale in Winnetka, CA
Looking for investment property in Winnetka, CA with high ROI ?
Explore a variety of short-term homes & houses in Winnetka, CA. Invest wisely with VRBO & Winnetka, CA 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 Winnetka, CA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
20134 Leadwell St #133Winnetka, CA20134 Leadwell St #133, Winnetka, CA 91306 | Condo/Coop |
2 beds | 2 baths | 884 sq.ft. |
$380,000 |
Airbnb cash on cash: 8.81%
|
20134 Leadwell Street #159Winnetka, CADonât miss this rare opportunity to own a premier ground-floor, 2-bedroom, 2-bathroom re... |
2 beds | 2 baths | 884 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.43%
|
20254 Stagg StreetWinnetka, CAWelcome to this beautiful recently renovated home that blends timeless character with mode... |
4 beds | 3 baths | 2,288 sq.ft. |
$928,500 |
Airbnb cash on cash: 9.96%
|
20253 Keswick St #326Winnetka, CANO ONE ABOVE YOU. ALL APPLIANCES INCLUDED. Charming and move-in ready 1-bedroom, 1-bath co... |
1 beds | 1 baths | 630 sq.ft. |
$345,000 |
Airbnb cash on cash: 3.83%
|
20428 Roscoe BoulevardWinnetka, CAWelcome to 20428 Roscoe Blvd, Winnetka, CA. A Thoughtfully Updated Home in the Heart of th... |
3 beds | 2 baths | 1,380 sq.ft. |
$878,000 |
Airbnb cash on cash: 6.39%
|
20341 Schoenborn StreetWinnetka, CA*MAJOR PRICE IMPROVEMENT!* Fully remodeled from top to bottom, this beautifully designed W... |
3 beds | 2 baths | 1,330 sq.ft. |
$899,900 |
Airbnb cash on cash: 6.54%
|
20308 Mobile StWinnetka, CAAmazing opportunity to own a newly renovated, immaculate, move in ready home in Winnetka's... |
5 beds | 4 baths | 2,500 sq.ft. |
$1,295,000 |
Airbnb cash on cash: 8.05%
|
8467 Penfield AvenueWinnetka, CAThe front of the home is beautifully manicured and features impressive Roman-style pillars... |
3 beds | 3 baths | 2,276 sq.ft. |
$959,000 |
Airbnb cash on cash: 5.71%
|
19714 Lull StreetWinnetka, CAThis two-story home is on a quiet cul-de-sac in a charming neighborhood in Winnetka. It fe... |
4 beds | 3 baths | 1,974 sq.ft. |
$939,000 |
Airbnb cash on cash: 9.73%
|
7812 Fairchild AvenueWinnetka, CAWelcome to your next home in the heart of Winnetka! Nestled on a peaceful, tree-lined stre... |
3 beds | 2 baths | 1,787 sq.ft. |
$925,000 |
Airbnb cash on cash: 5.98%
|
8328 N Cooper PlaceWinnetka, CAWelcome to Cooper Place! This newer-built traditional Modern Farmhouse features 4 bedrooms... |
4 beds | 3 baths | 2,507 sq.ft. |
$1,249,000 |
Airbnb cash on cash: 6.95%
|
20134 Leadwell St #156Winnetka, CA20134 Leadwell St #156, Winnetka, CA 91306 | Condo/Coop |
2 beds | 1 baths | 855 sq.ft. |
$399,999 |
Airbnb cash on cash: 8%
|
7640 Oso Avenue #316Winnetka, CAThis incredible 1+1 freshly painted penthouse unit with vaulted ceiling is very bright wit... |
1 beds | 1 baths | 648 sq.ft. |
$319,990 |
Airbnb cash on cash: 4.83%
|
20551 Saticoy StreetWinnetka, CAWOW!!! Great Opportunity for a large family. Fully remodeled, new roof, new copper plumbi... |
3 beds | 2 baths | 1,543 sq.ft. |
$865,000 |
Airbnb cash on cash: 6.52%
|
20329 Stagg StWinnetka, CAA newly constructed Spanish-style masterpiece offering top-of-the-line 2025 construction. ... |
5 beds | 5 baths | 3,700 sq.ft. |
$1,795,000 |
Airbnb cash on cash: 5.2%
|
7463 Mason AvenueWinnetka, CAFantastic Opportunity for you to own your own Private Oasis! You are welcomed by a beauti... |
3 beds | 2 baths | 1,636 sq.ft. |
$899,990 |
Airbnb cash on cash: 5.94%
|
7306 Jumilla AvenueWinnetka, CASFR, Standard ADU, and JR ADU! This stunning turn key home with its 2 ADUs is nestled in ... |
4 beds | 3 baths | 1,970 sq.ft. |
$1,350,000 |
Airbnb cash on cash: 6.31%
|
8101 Sunnybrae AvenueWinnetka, CASeller is offering a $10,000 CREDIT TO THE BUYER! Step into this beautifully remodeled sin... |
3 beds | 2 baths | 1,572 sq.ft. |
$885,000 |
Airbnb cash on cash: 6.33%
|
7812 Fairchild Avenue 7812Winnetka, CAWelcome to your next home in the heart of Winnetka! Nestled on a peaceful, tree-lined stre... |
3 beds | 2 baths | 1,787 sq.ft. |
$925,000 |
Airbnb cash on cash: 5.98%
|
20651 Roscoe Boulevard #LWinnetka, CAThis two-story, three-bedroom 2.5 bath townhouse is a rare find!! With features like an e... |
3 beds | 2 baths | 1,586 sq.ft. |
$670,000 |
Airbnb cash on cash: 7.98%
|
20224 Sherman Way #26Winnetka, CA20224 Sherman Way #26, Winnetka, CA 91306 | Townhouse |
3 beds | 3 baths | 1,843 sq.ft. |
$599,000 |
Airbnb cash on cash: 9.3%
|
6210 Penfield AveWinnetka, CA6210 Penfield Ave, Winnetka, CA 91367 | Single Family Residential |
4 beds | 3 baths | 2,682 sq.ft. |
$2,295,000 |
Airbnb cash on cash: 2.87%
|
7230 Kelvin Avenue #6Winnetka, CAWelcome to Kelvin Court, a gated and well maintained community where comfort meets conveni... |
3 beds | 2 baths | 1,488 sq.ft. |
$589,000 |
Airbnb cash on cash: 9.42%
|
19545 Sherman Way #74Winnetka, CAWelcome to this stunning, updated condo with pool view in Reseda! This updated 2-bedroom, ... |
2 beds | 1 baths | 1,319 sq.ft. |
$559,000 |
Airbnb cash on cash: 5.5%
|
20253 Keswick #233Winnetka, CAWelcome to 20253 Keswick Street, a beautifully maintained 2-bedroom, 2-bath condo located ... |
2 beds | 2 baths | 880 sq.ft. |
$430,000 |
Airbnb cash on cash: 7.35%
|
20253 Keswick Street #103Winnetka, CADon't miss this Upgraded, Open Floor Plan, Two Bedroom, Two Bathroom Condominium with a Hu... |
2 beds | 2 baths | 880 sq.ft. |
$435,000 |
Airbnb cash on cash: 7.25%
|
20243 Lanark StreetWinnetka, CAThis stunning 2,932-square-foot Winnetka home features 4 bedrooms, 3 baths, and 3 versatil... |
4 beds | 3 baths | 2,932 sq.ft. |
$1,079,000 |
Airbnb cash on cash: 8.33%
|
20258 Cohasset St unit: 4 #4Winnetka, CABeautiful bright 2 level townhouse with back patio. 2 bedroom and 1 1/2 bath. Central Heat... |
2 beds | 2 baths | 1,050 sq.ft. |
$456,000 |
Airbnb cash on cash: 7.07%
|
7107 CozycroftWinnetka, CA7107 Cozycroft, Winnetka, CA 91306 | Single Family Residential |
9 beds | 8 baths | 3,624 sq.ft. |
$2,200,000 |
Airbnb cash on cash: 4.03%
|
20617 SchoenbornWinnetka, CA"This beautifully remodeled home features an open floor plan, a stunning modern kitchen, a... |
3 beds | 2 baths | 1,392 sq.ft. |
$799,000 |
Airbnb cash on cash: 7.2%
|
8429 SunnybraeWinnetka, CAWelcome Home! Discover this beautifully remodeled 4-bedroom, 2-bathroom residence nestled... |
4 beds | 2 baths | 1,479 sq.ft. |
$977,000 |
Airbnb cash on cash: 9.38%
|
20134 Leadwell Street unit: 374 #374Winnetka, CASeller is motivated. Modern construction, the condo is situated on the top 3rd level. Feau... |
2 beds | 2 baths | 888 sq.ft. |
$405,000 |
Airbnb cash on cash: 7.88%
|
20231 ElkwoodWinnetka, CAStep into modern luxury with this fully remodeled 2-story home offering 4 bedrooms, 4 bath... |
5 beds | 4 baths | 3,229 sq.ft. |
$1,249,999 |
Airbnb cash on cash: 8.4%
|
7414 QuartzWinnetka, CAThis beautiful home in nestled on one of Winnetkaâs most sought-after family neighborhoo... |
3 beds | 2 baths | 1,588 sq.ft. |
$950,000 |
Airbnb cash on cash: 5.78%
|
20737 Roscoe #704Winnetka, CAWindsor Park 2 + 2 1/2 Townhome with Great Floorplan. Laminate Floors, Recessed Lights, Gr... |
2 beds | 1 baths | 1,580 sq.ft. |
$620,000 |
Airbnb cash on cash: 4.6%
|
Real Estate investment in Winnetka, CA
There are 57 properties for sale in the city of Winnetka . The median list price in Winnetka is $870,000 and the average price per square foot is $527. In December 2025, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $4,000.