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%
|
8213 Lurline AveWinnetka, CACharming Updated Winnetka Home! Spectacular curb appeal with an immaculate lawn & garden, ... |
3 beds | 2 baths | 1,385 sq.ft. |
$929,000 |
Airbnb cash on cash: 6.05%
|
20134 Leadwell St #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%
|
8446 Penfield AveWinnetka, CAMASSIVE 22,000 SQ FT FLAT LOT!!! Located just minutes away from Northridge Mall. What sets... |
6 beds | 5 baths | 2,697 sq.ft. |
$1,574,000 |
Airbnb cash on cash: 6.99%
|
20254 Stagg StWinnetka, 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%
|
20242 Gresham StreetWinnetka, CAWelcome to your new home in the Heart of Winnetka! Perfectly situated on a quiet, tree-lin... |
3 beds | 2 baths | 1,650 sq.ft. |
$749,900 |
Airbnb cash on cash: 8.13%
|
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 | 3 baths | 2,500 sq.ft. |
$1,295,000 |
Airbnb cash on cash: 8.05%
|
8467 Penfield AveWinnetka, 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%
|
20134 Leadwell St #263Winnetka, CABring in the New Year with a remodeled 2 Bedroom, 2Bathroom Condo in Winnetka. This unit h... |
2 beds | 2 baths | 884 sq.ft. |
$419,000 |
Airbnb cash on cash: 7.43%
|
8600 Mason AveWinnetka, CAThis home is currently set up for SOBER LIVING ARRANGEMENTS and the details can be found i... |
4 beds | 3 baths | 1,958 sq.ft. |
$874,999 |
Airbnb cash on cash: 9.45%
|
20630 Chase StWinnetka, CAPool homes in Winnetka are always in demandâand this one delivers. Welcome to 20630 Chas... |
4 beds | 2 baths | 1,839 sq.ft. |
$949,000 |
Airbnb cash on cash: 9.71%
|
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%
|
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 Ave #316Winnetka, CAThis incredible 1+1 freshly painted penthouse unit with vaulted ceiling is very bright wit... |
1 beds | 1 baths | 648 sq.ft. |
$315,990 |
Airbnb cash on cash: 4.91%
|
20551 Saticoy StWinnetka, 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 AveWinnetka, 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 AveWinnetka, 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. |
$1,300,000 |
Airbnb cash on cash: 6.62%
|
7812-7812 Fairchild AveWinnetka, 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 Blvd #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%
|
7230 Kelvin Ave #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%
|
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%
|
20243 Lanark StWinnetka, 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 #4Winnetka, CABeautiful bright 2 level townhouse with back patio. 2 bedroom and 1 1/2 bath. Central Heat... |
2 beds | 1 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%
|
20134 Leadwell St #374Winnetka, CASeller is very motivated. Lots of amenities . style Modern construction, the condo is situ... |
2 beds | 2 baths | 888 sq.ft. |
$395,000 |
Airbnb cash on cash: 8.12%
|
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%
|
20838 Bryant StWinnetka, CAWelcome to 20838 Bryant Street, a beautifully maintained two-story contemporary home in th... |
4 beds | 2 baths | 2,171 sq.ft. |
$928,888 |
Airbnb cash on cash: 9.95%
|
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 | 2 baths | 1,580 sq.ft. |
$620,000 |
Airbnb cash on cash: 4.6%
|
20528 Hamlin StWinnetka, CA20528-& 20526 Hamlin St, Winnetka, CA 91306 | Single Family Residential |
5 beds | 3 baths | 1,788 sq.ft. |
$1,259,777 |
Airbnb cash on cash: 8.33%
|
20247 LanarkWinnetka, CAâCharming triplex in Winnetka â this well-maintained property offers a rare opportunit... |
14 beds | 6 baths | 2,520 sq.ft. |
$1,900,000 |
Airbnb cash on cash: 5.35%
|
8021 NW Mcnulty AveWinnetka, CA8021 NW Mcnulty Ave, Los Angeles, CA 91306 | Single Family Residential |
3 beds | 2 baths | 1,592 sq.ft. |
$1,450,000 |
Airbnb cash on cash: 3.19%
|
20224 Sherman #14Winnetka, CAWelcome to this spacious and well-maintained 4-bedroom, 3-bath townhome located in a desir... |
3 beds | 3 baths | 1,843 sq.ft. |
$639,000 |
Airbnb cash on cash: 8.5%
|
20234 CantaraWinnetka, CAThis is a one bedroom STUDIO which has a partition for privacy. It is still considered a S... |
1 beds | 1 baths | 444 sq.ft. |
$279,000 |
Airbnb cash on cash: 5.4%
|
Real Estate investment in Winnetka, CA
There are 54 properties for sale in the city of Winnetka . The median list price in Winnetka is $890,000 and the average price per square foot is $531. In January 2026, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $4,047.