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 |
|---|---|---|---|
20439 Malden StreetWinnetka, CACharming single-story home in Winnetka featuring 3 bedrooms and 2 bathrooms with recent up... |
3 beds | 1 baths | 2,085 sq.ft. |
$799,900 |
Airbnb cash on cash: 4.16%
|
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. |
$644,000 |
Airbnb cash on cash: 4.58%
|
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. |
$375,000 |
Airbnb cash on cash: 2.64%
|
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%
|
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: 1.63%
|
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%
|
20737 Roscoe Boulevard #203Winnetka, CAWelcome to this beautifully updated townhome in the highly desirable Windsor Park communit... |
2 beds | 3 baths | 1,580 sq.ft. |
$559,990 |
Airbnb cash on cash: 1.19%
|
8430 Winnetka Avenue #20Winnetka, CAPrice Reduction!!! Rare opportunity with unlimited potential in this spacious and inviting... |
3 beds | 3 baths | 1,587 sq.ft. |
$524,000 |
Airbnb cash on cash: 6.04%
|
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. |
$335,000 |
Airbnb cash on cash: 3.4%
|
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%
|
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!!! Beautiful and renovated large two bedroom townhome features an op... |
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%
|
7211 Cozycroft #19Winnetka, CAWelcome to this nicely updated, move-in-ready 1-bedroom, 1-bathroom corner unit in the Par... |
1 beds | 1 baths | 839 sq.ft. |
$379,000 |
Airbnb cash on cash: 1.65%
|
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. |
$389,000 |
Airbnb cash on cash: 2.42%
|
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. |
$404,404 |
Airbnb cash on cash: 2.17%
|
20701 SchoolcraftWinnetka, CABeautifully renovated four-bedroom, two-bathroom home offering approximately 1,300 square ... |
4 beds | 2 baths | 1,216 sq.ft. |
$899,950 |
Airbnb cash on cash: 2.37%
|
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. |
$955,000 |
Airbnb cash on cash: 2.14%
|
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, CAWelcome to Sherman Courts â One of Winnetka's Most Sought-After Gated Communities This ... |
3 beds | 3 baths | 1,843 sq.ft. |
$635,000 |
Airbnb cash on cash: 4.77%
|
8330 Penfield #11Winnetka, CAThis inviting Winnetka townhouse perfectly combines comfort, convenience, and charm in a d... |
2 beds | 3 baths | 1,123 sq.ft. |
$495,000 |
Airbnb cash on cash: 1.63%
|
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, 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. |
$774,950 |
Airbnb cash on cash: 4.19%
|
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%
|
20327 Saticoy #309Winnetka, CACondo in the City of Winnetka sounds like a Great Opportunity for a New Owner or Investor ... |
1 beds | 1 baths | 640 sq.ft. |
$339,995 |
Airbnb cash on cash: 3.24%
|
20756 Saticoy StreetWinnetka, CAWelcome to this beautifully remodeled single-story home in the heart of Winnetka â a tur... |
3 beds | 2 baths | 1,569 sq.ft. |
$924,500 |
Airbnb cash on cash: 3.37%
|
8241 Mason Avenue #CWinnetka, CAWelcome to this beautifully remodeled 3 bedroom 2.5 bathroom Townhome offering the perfect... |
3 beds | 2 baths | 1,424 sq.ft. |
$599,000 |
Airbnb cash on cash: 5.02%
|
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. |
$1,675,000 |
Airbnb cash on cash: 0.38%
|
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%
|
8469 FullbrightWinnetka, CAWelcome to 8469 Fulbright Ave, a beautifully updated single-story home with great curb app... |
3 beds | 2 baths | 1,375 sq.ft. |
$899,000 |
Airbnb cash on cash: 3.51%
|
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. |
$1,575,000 |
Airbnb cash on cash: 0.51%
|
20146 HartlandWinnetka, CAPrice Improvement! Now $849,000. Come see us at the open house this Sunday, 8/30, from 1-4... |
3 beds | 2 baths | 1,202 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.82%
|
Real Estate investment in Winnetka, CA
There are 72 properties for sale in the city of Winnetka . The median list price in Winnetka is $799,450 and the average price per square foot is $465. In September 2026, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $3,843.