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 |
|---|---|---|---|
20146 Cohasset Street #5Winnetka, CAWelcome to this spacious and inviting two-story condominium offering 1,340 square feet of ... |
3 beds | 2 baths | 1,340 sq.ft. |
$459,000 |
Airbnb cash on cash: 7.56%
|
19928 Chase Street #23Winnetka, CAMove-in ready 3-bedroom, 3-bathroom townhome situated on a quiet residential street surrou... |
3 beds | 3 baths | 1,459 sq.ft. |
$599,000 |
Airbnb cash on cash: 5%
|
20253 Keswick Street #331Winnetka, CAWelcome To The Terramar * Updated Top Floor Condo * Bright * 2 Bedrooms / 2 Bathrooms * 88... |
2 beds | 2 baths | 880 sq.ft. |
$370,000 |
Airbnb cash on cash: 2.69%
|
8340 Penfield Ave #35Winnetka, CAWelcome to this beautifully updated two-story townhome located in the heart of Winnetka. N... |
3 beds | 2 baths | 1,282 sq.ft. |
$625,000 |
Airbnb cash on cash: 4.9%
|
7640 Oso Avenue #311Winnetka, CAA little charm, a lot of opportunity! Welcome to 7640 Oso Avenue in the heart of Winnetka.... |
1 beds | 1 baths | 648 sq.ft. |
$295,000 |
Airbnb cash on cash: 3.51%
|
20358 Strathern StreetWinnetka, CAWelcome to this beautifully updated single-story ranch home in a highly sought-after pocke... |
3 beds | 2 baths | 2,256 sq.ft. |
$1,275,000 |
Airbnb cash on cash: 2.53%
|
7916 Mason AvenueWinnetka, CAWelcome to this beautifully updated 4-bedroom, 2-bathroom home offering bright, open livin... |
4 beds | 1 baths | 1,923 sq.ft. |
$939,900 |
Airbnb cash on cash: 2.2%
|
6952 Cozycroft AvenueWinnetka, CAWelcome to 6952 & 6954 Cozycroft Avenue! This beautifully remodeled, resort-style property... |
4 beds | 3 baths | 2,251 sq.ft. |
$1,379,000 |
Airbnb cash on cash: 0.94%
|
8430 Winnetka Avenue #20Winnetka, CAPrice Reduction!!! Rare opportunity with unlimited potential in this spacious and inviting... |
3 beds | 3 baths | 1,587 sq.ft. |
$509,000 |
Airbnb cash on cash: 6.27%
|
20329 Stagg StWinnetka, CA** NEWLY REDUCED! TOP-OF-THE-LINE 2025 construction. A newly constructed Spanish-style mas... |
5 beds | 4 baths | 3,700 sq.ft. |
$1,590,000 |
Airbnb cash on cash: 2.7%
|
20234 Cantara #214Winnetka, CAWelcome home to this bright and spacious 925 sq ft condo featuring a highly desirable open... |
2 beds | 2 baths | 925 sq.ft. |
$320,000 |
Airbnb cash on cash: 3.63%
|
20253 Keswick #322Winnetka, CAWelcome to this beautifully updated condominium offering comfort, style, and exceptional v... |
2 beds | 2 baths | 880 sq.ft. |
$395,000 |
Airbnb cash on cash: 2.43%
|
20155 Keswick #209Winnetka, CAFHA Approved Townhome!!! **New A/C, new dishwasher, and fresh new paint**... Beautiful and... |
2 beds | 2 baths | 1,125 sq.ft. |
$460,000 |
Airbnb cash on cash: 1.95%
|
20458 MaldenWinnetka, CAGreat Home needs updating Great location |
4 beds | 2 baths | 1,572 sq.ft. |
$800,000 |
Airbnb cash on cash: 2.89%
|
20253 Keswick Street #318Winnetka, CAGreat new price and lender warrantable! Yay! Priced to sell! Don't miss this amazing op... |
2 beds | 2 baths | 880 sq.ft. |
$365,000 |
Airbnb cash on cash: 2.69%
|
20134 Leadwell #126Winnetka, CASpacious first-floor 2-bedroom, 1-bath condo in a quiet gated community in Winnetka. This ... |
2 beds | 1 baths | 786 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.22%
|
20701 SchoolcraftWinnetka, CABeautifully renovated four-bedroom, two-bathroom home. Thoughtfully updated living space. ... |
4 beds | 2 baths | 1,350 sq.ft. |
$875,000 |
Airbnb cash on cash: 2.49%
|
20748 VoseWinnetka, CAWelcome to this beautiful home in the heart of the San Fernando Valley. Boasting lovely cu... |
4 beds | 3 baths | 2,109 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.16%
|
20134 Leadwell #307Winnetka, CAWelcome to this beautifully renovated corner unit, thoughtfully updated with comfort, styl... |
3 beds | 2 baths | 1,113 sq.ft. |
$519,900 |
Airbnb cash on cash: 5.96%
|
20214 Cohasset Street #16Winnetka, CAWelcome to this bright and inviting 2-bedroom, 1-bath end-unit condo, ideally located on t... |
2 beds | 1 baths | 880 sq.ft. |
$339,000 |
Airbnb cash on cash: 3.43%
|
20230 Keswick #3Winnetka, CAHome can qualify for up to $15,000 towards down payment assistance, closing costs, or rate... |
3 beds | 2 baths | 1,463 sq.ft. |
$680,000 |
Airbnb cash on cash: 5.07%
|
6547 KelvinWinnetka, CALocated in one of Winnetka's most sought-after neighborhoods, this upgraded property offer... |
4 beds | 3 baths | 1,740 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.62%
|
20253 Hamlin StWinnetka, CAExperience classic California living in this beautifully remodeled Winnetka home, set in a... |
4 beds | 2 baths | 1,344 sq.ft. |
$949,000 |
Airbnb cash on cash: 2.16%
|
20224 Sherman #48Winnetka, CAMOTIVATED SELLER! Welcome to Sherman Courts â One of Winnetka's Most Sought-After Gated ... |
3 beds | 3 baths | 1,843 sq.ft. |
$599,999 |
Airbnb cash on cash: 5.15%
|
20234 Cantara #342Winnetka, CAThis is perhaps the lowest price point for entry in the area today, you can be a homeowner... |
N/A beds | 1 baths | 484 sq.ft. |
$250,000 |
Airbnb cash on cash: 3.26%
|
20355 MobileWinnetka, CAMAJOR PRICE IMPROVEMENT! An exceptional opportunity in Winnetka â beautifully remodeled ... |
4 beds | 1 baths | 1,693 sq.ft. |
$897,000 |
Airbnb cash on cash: 2.39%
|
8231 Mason Avenue #CWinnetka, CAWelcome to this spacious 3-bedroom, 2.5-bathroom townhome with approximately 1,424 square ... |
3 beds | 2 baths | 1,424 sq.ft. |
$550,000 |
Airbnb cash on cash: 5.61%
|
7329 KelvinWinnetka, CANEW CONSTRUCTION â Turn Key Home. Welcome to gated Kelvin Homes! Modern home 4 bed/4.5 b... |
4 beds | 4 baths | 3,090 sq.ft. |
$1,549,000 |
Airbnb cash on cash: 0.55%
|
20310 LondeliusWinnetka, CAAfter a new price improvement, this home is now one of the best values in the neighborhood... |
3 beds | 2 baths | 1,462 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.82%
|
20811 W Seeasons LaneWinnetka, CANEW CONSTRUCTION â Turn Key Home. Welcome to gated Kelvin Homes! Modern home 4 bed/4.5 b... |
4 beds | 4 baths | 2,925 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 0.67%
|
20146 HartlandWinnetka, CAPrice Improvement! Now $849,000. Come see us at the open house next Sunday, 10/18, from 1:... |
3 beds | 2 baths | 1,202 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.82%
|
8018 Winnetka AvenueWinnetka, CAExtensively renovated from top to bottom, this stunning single-story Winnetka home offers ... |
4 beds | 2 baths | 2,038 sq.ft. |
$999,999 |
Airbnb cash on cash: 1.96%
|
8518 Fullbright AvenueWinnetka, CABack on market, Opportunity Awaits in Winnetka! This single-story Ranch-style home offers ... |
3 beds | 2 baths | 1,749 sq.ft. |
$790,000 |
Airbnb cash on cash: 4.23%
|
8434 Oakdale AvenueWinnetka, CAWelcome to this rare opportunity featuring three detached homes on one expansive 9,461 sqf... |
6 beds | N/A baths | 2,848 sq.ft. |
$1,649,950 |
Airbnb cash on cash: 1.23%
|
20253 Keswick #211Winnetka, CAHome for the Holidays!! Ready to move in, 2-bedroom, 2 bath condo, master bedroom with its... |
2 beds | 2 baths | 880 sq.ft. |
$363,500 |
Airbnb cash on cash: 2.71%
|
20562 SkourasWinnetka, CAWelcome to this stylish 3-bedroom home in Winnetka, offering a unique modern feel with an ... |
3 beds | 2 baths | 1,362 sq.ft. |
$949,000 |
Airbnb cash on cash: 2.9%
|
19700 LullWinnetka, CAWelcome home! This spacious and beautifully updated 4-bedroom, 3.5-bath home with 2,070 SF... |
4 beds | 2 baths | 2,070 sq.ft. |
$1,249,000 |
Airbnb cash on cash: 1.22%
|
20224 Cohasset Street #9Winnetka, CAWelcome home to the desirable Forest Glen Community in Winnetka! This updated end unit tow... |
2 beds | 2 baths | 1,050 sq.ft. |
$449,000 |
Airbnb cash on cash: 2.17%
|
20234 Cantara Street #224Winnetka, CABeautifully updated, move-in ready studio in Winnetka. This bright and inviting unit featu... |
N/A beds | 1 baths | 444 sq.ft. |
$229,000 |
Airbnb cash on cash: 3.4%
|
19860 Arminta StreetWinnetka, CATucked in a quiet, private neighborhood, imagine your holidays in this adorable corner lot... |
4 beds | 1 baths | 2,165 sq.ft. |
$839,995 |
Airbnb cash on cash: 2.77%
|
Real Estate investment in Winnetka, CA
There are 71 properties for sale in the city of Winnetka . The median list price in Winnetka is $780,000 and the average price per square foot is $461. In October 2026, the average monthly cash on cash return in Winnetka is 4.00%. The average monthly rental income in Winnetka is $3,891.