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 |
|---|---|---|---|
19803 Bassett StWinnetka, CA19803 Bassett St, Winnetka, CA 91306 | Single Family Residential |
3 beds | 2 baths | 1,417 sq.ft. |
$849,990 |
Airbnb cash on cash: 3.92%
|
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. |
$620,000 |
Airbnb cash on cash: 4.8%
|
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%
|
7708 Oakdale AvenueWinnetka, CAStunning 2 Story Winnetka Beauty. This Beautiful home boasts 2294 sq ft of living space, 4... |
4 beds | 3 baths | 2,294 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.16%
|
20134 Leadwell St #334Winnetka, CABack On Market. SOLD with Multiple Offers last time! Buyer did not perform. This beautiful... |
3 beds | 2 baths | 1,113 sq.ft. |
$475,000 |
Airbnb cash on cash: 6.68%
|
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%
|
6915 Laramie AveWinnetka, CAPositioned on an oversized lot with mature trees, is this charming post-war traditional st... |
6 beds | 5 baths | 2,825 sq.ft. |
$1,499,999 |
Airbnb cash on cash: 3.91%
|
7445 Oakdale AvenueWinnetka, CAExceptional Investment Opportunity in Prime Winnetka â Generating $11,050/month in Renta... |
6 beds | 4 baths | 2,570 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 3.18%
|
20234 Cantara St #229Winnetka, CACharming 1-bedroom unit featuring abundance of natural light, a tastefully updated bathroo... |
1 beds | 1 baths | 744 sq.ft. |
$379,000 |
Airbnb cash on cash: 1.9%
|
6952 Cozycroft AvenueWinnetka, CAWelcome to 6952 & 6954 Cozycroft Avenue! This beautifully remodeled, resort-style property... |
4 beds | 3 baths | 2,251 sq.ft. |
$1,395,000 |
Airbnb cash on cash: 0.91%
|
6564 Kelvin AveWinnetka, CACall or text Jennifer for more information at 818-425-7907. Ask about the video of the hou... |
5 beds | 3 baths | 1,880 sq.ft. |
$999,000 |
Airbnb cash on cash: 5.71%
|
20112 Runnymede St #3Winnetka, CAWELCOME TO THIS BEAUTIFUL 3 BEDROOM WITH 2.5 BATH TOWNHOME IN A GATED COMMUNITY. LIVING R... |
3 beds | 2 baths | 1,329 sq.ft. |
$599,999 |
Airbnb cash on cash: 5.22%
|
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%
|
20327 Saticoy Street #102Winnetka, CAAn affordable opportunity to own in the San Fernando Valley! This well-maintained, freshly... |
1 beds | 1 baths | 640 sq.ft. |
$280,000 |
Airbnb cash on cash: 4.3%
|
8353 Lurline AveWinnetka, CA8353 Lurline Ave, Winnetka, CA 91306 | Single Family Residential |
3 beds | 2 baths | 1,482 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.82%
|
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%
|
20309 RoscoeWinnetka, CABeautifully updated 3-bedroom, 2-bath home featuring modern upgrades throughout. This move... |
3 beds | 2 baths | 1,321 sq.ft. |
$799,000 |
Airbnb cash on cash: 4.17%
|
7211 Cozycroft #32Winnetka, CA$35000 Price Reduction WOW WOW WOW Lowest Available in the complex Come see and fall in LO... |
2 beds | 2 baths | 1,033 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.11%
|
20253 Keswick Street #318Winnetka, CAGreat new price...Priced to sell! Don't miss this Light and Bright, Move-in Ready Third F... |
2 beds | 2 baths | 880 sq.ft. |
$385,000 |
Airbnb cash on cash: 2.46%
|
20234 Cantara Street #314Winnetka, CAWelcome to this inviting 2-bedroom, 2-bathroom top-floor condo Unit 314 at 20234 Cantara S... |
2 beds | 2 baths | 925 sq.ft. |
$360,000 |
Airbnb cash on cash: 3.04%
|
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 offering approximately 1,300 square ... |
4 beds | 2 baths | 1,350 sq.ft. |
$888,888 |
Airbnb cash on cash: 2.42%
|
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 may qualify for up to $15,000 towards down payment assistance or closing costs! Where... |
3 beds | 2 baths | 1,463 sq.ft. |
$695,999 |
Airbnb cash on cash: 4.92%
|
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%
|
20146 Cohasset #11Winnetka, CAWelcome to this bright and inviting 3-bedroom, 2-bath home located in a lovely neighborhoo... |
3 beds | 1 baths | 1,340 sq.ft. |
$495,000 |
Airbnb cash on cash: 6.69%
|
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. |
$625,000 |
Airbnb cash on cash: 4.88%
|
20710 Haynes StWinnetka, CASold before processing |
4 beds | 2 baths | 1,920 sq.ft. |
$1,199,999 |
Airbnb cash on cash: 1.87%
|
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%
|
20247 PartheniaWinnetka, CA20247 Parthenia, Winnetka, CA 91306 | Single Family Residential |
6 beds | 3 baths | 2,180 sq.ft. |
$1,090,000 |
Airbnb cash on cash: 5.09%
|
20355 MobileWinnetka, CABeautifully renovated pool home with detached ADU in the heart of Winnetka. Situated on an... |
4 beds | 1 baths | 1,800 sq.ft. |
$997,000 |
Airbnb cash on cash: 1.97%
|
20457 Schoolcraft StreetWinnetka, CAWelcome home to 20457 Schoolcraft St, a refreshed single-story in the heart of central Win... |
3 beds | 2 baths | 1,225 sq.ft. |
$749,950 |
Airbnb cash on cash: 4.37%
|
Real Estate investment in Winnetka, CA
There are 95 properties for sale in the city of Winnetka . The median list price in Winnetka is $835,000 and the average price per square foot is $470. In September 2026, the average monthly cash on cash return in Winnetka is 4.00%. The average monthly rental income in Winnetka is $3,946.