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 |
|---|---|---|---|
7647 Mason AvenueWinnetka, CALush Pool Home with Solar & Fruit Trees in the Heart of Winnetka! Discover comfort, style,... |
3 beds | 2 baths | 2,073 sq.ft. |
$868,000 |
Airbnb cash on cash: 6.49%
|
20253 Keswick St #325Winnetka, CAMotivated Seller. Welcome home to this light and bright unit with 2B/2B. Quiet luxury buil... |
2 beds | 2 baths | 880 sq.ft. |
$429,500 |
Airbnb cash on cash: 7.29%
|
20234 Cantara St #136Winnetka, CA**PRICE IMPROVEMENT** Turnkey vs fixer opportunity Welcome to this charming studio that ... |
N/A beds | 1 baths | 444 sq.ft. |
$259,000 |
Airbnb cash on cash: 6.19%
|
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: 9.69%
|
20428 Roscoe BlvdWinnetka, CAWelcome to 20428 Roscoe Blvd, Winnetka, CA. A Thoughtfully Updated Home in the Heart of th... |
3 beds | 2 baths | 1,380 sq.ft. |
$899,000 |
Airbnb cash on cash: 6.21%
|
8620 Lubao AvenueWinnetka, CAThis exceptional income property offers the potential to generate approximately $10,900 (!... |
7 beds | 7 baths | 3,280 sq.ft. |
$1,785,000 |
Airbnb cash on cash: 2.83%
|
7445 Oakdale AvenueWinnetka, CAExceptional Investment Opportunity in Prime Winnetka â Generating $10,500/month in Renta... |
6 beds | 4 baths | 2,570 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 3.02%
|
7916 Mason AveWinnetka, CAWelcome to this beautifully updated 4-bedroom, 2-bathroom home offering bright, open livin... |
4 beds | 1 baths | 1,923 sq.ft. |
$949,000 |
Airbnb cash on cash: 9.71%
|
7410 Cozycroft AvenueWinnetka, CAThis beautifully remodeled home is nestled on a picturesque tree lined street in one of Wi... |
4 beds | 4 baths | 1,557 sq.ft. |
$999,900 |
Airbnb cash on cash: 9.77%
|
7211 Cozycroft Ave #50Winnetka, CAMotivated seller!!!!!!Nestled in one of the most sought after neighborhoods of Winnetka th... |
2 beds | 2 baths | 1,033 sq.ft. |
$455,000 |
Airbnb cash on cash: 6.87%
|
20851 Community St #10Winnetka, CAStunning Remodeled Home in Gated Community â Move-In Ready! Step into Style and Comfort ... |
3 beds | 3 baths | 1,460 sq.ft. |
$650,000 |
Airbnb cash on cash: 8.37%
|
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. |
$599,900 |
Airbnb cash on cash: 4.77%
|
20454 W Strathern StWinnetka, CA20454 W Strathern St, Los Angeles, CA 91306 | Single Family Residential |
8 beds | 5 baths | 3,022 sq.ft. |
$1,549,000 |
Airbnb cash on cash: 6.45%
|
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. |
$874,950 |
Airbnb cash on cash: 9.45%
|
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%
|
7640 Oso Ave #316Winnetka, CAThis stunning 1-bedroom, 1-bath condo offers an abundance of natural light, soaring ceilin... |
1 beds | 1 baths | 648 sq.ft. |
$295,000 |
Airbnb cash on cash: 5.38%
|
20401 Napa StreetWinnetka, CAWelcome to this beautifully maintained turnkey 3-bedroom, 2-bath home featuring a bonus co... |
3 beds | 2 baths | 1,627 sq.ft. |
$869,000 |
Airbnb cash on cash: 6.48%
|
20329 Stagg StWinnetka, CATOP-OF-THE-LINE 2025 construction. A newly constructed Spanish-style masterpiece- still in... |
5 beds | 5 baths | 3,700 sq.ft. |
$1,695,000 |
Airbnb cash on cash: 5.56%
|
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%
|
7230 Kelvin Ave #6Winnetka, CAWelcome to Kelvin Court, a gated and well maintained community where comfort meets conveni... |
3 beds | 3 baths | 1,488 sq.ft. |
$579,000 |
Airbnb cash on cash: 9.61%
|
20819 W Seasons LnWinnetka, CANEW CONSTRUCTION â Welcome to gated Kelvin Homes! Modern home 4 bed/3 bath with a Great ... |
4 beds | 3 baths | 2,575 sq.ft. |
$1,395,000 |
Airbnb cash on cash: 5.95%
|
20456 W Strathern StWinnetka, CA20456 W Strathern St, Los Angeles, CA 91306 | Single Family Residential |
8 beds | N/A baths | 3,022 sq.ft. |
$1,549,000 |
Airbnb cash on cash: 5.28%
|
20327 Saticoy #304Winnetka, CAWelcome home to this beautifully maintained and thoughtfully laid-out residence that blend... |
1 beds | 1 baths | 640 sq.ft. |
$344,000 |
Airbnb cash on cash: 4.77%
|
20422-20424 SchoenbornWinnetka, CA**HUGE PRICE IMPROVEMENT** plus **SELLER OFFERING CREDITS up to $20,000 TOWARD BUYER'S CLO... |
4 beds | 3 baths | 2,392 sq.ft. |
$1,129,000 |
Airbnb cash on cash: 7.89%
|
20155 Keswick #209Winnetka, CAFHA Approved Townhome!!! Beautiful and renovated large two bedroom townhome features an op... |
2 beds | 2 baths | 1,125 sq.ft. |
$470,000 |
Airbnb cash on cash: 6.71%
|
20234 Cantara St #130Winnetka, CA20234 Cantara St #130, Winnetka, CA 91306 | Condo/Coop |
1 beds | 1 baths | 444 sq.ft. |
$229,000 |
Airbnb cash on cash: 6.93%
|
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. |
$389,000 |
Airbnb cash on cash: 2.97%
|
7101 Oso Avenue #16Winnetka, CAWelcome to 7101 Oso Ave #16, a charming free standing detached home tucked inside an intim... |
3 beds | 3 baths | 1,926 sq.ft. |
$830,000 |
Airbnb cash on cash: 6.3%
|
19918 KittridgeWinnetka, CA19918 Kittridge, Winnetka, CA 91306 | Single Family Residential |
8 beds | 6 baths | 3,395 sq.ft. |
$1,850,000 |
Airbnb cash on cash: 5.12%
|
20309 RoscoeWinnetka, CABeautifully updated 3-bedroom, 2-bath home featuring modern upgrades throughout. This move... |
3 beds | 2 baths | 1,321 sq.ft. |
$879,000 |
Airbnb cash on cash: 6.39%
|
7211 Cozycroft #32Winnetka, CAHOT HOT HOT...DO NOT MISS THIS ONE! Generous Buyers' incentive and new lower price. Move ... |
2 beds | 2 baths | 1,033 sq.ft. |
$434,900 |
Airbnb cash on cash: 7%
|
19928 Chase St #27Winnetka, CA19928 Chase St #27, Winnetka, CA 91306 | Townhouse |
2 beds | 3 baths | 1,270 sq.ft. |
$519,000 |
Airbnb cash on cash: 5.86%
|
20237 Hartland StWinnetka, CA20237 Hartland St, Winnetka, CA 91306 | Single Family Residential |
9 beds | 8 baths | 3,343 sq.ft. |
$1,599,999 |
Airbnb cash on cash: 6.19%
|
7640 Oso #318Winnetka, CAFirst Team Real Estate welcomes you home to your private retreat in the heart of Winnetka.... |
2 beds | 2 baths | 899 sq.ft. |
$420,000 |
Airbnb cash on cash: 7.83%
|
7118 SunnybraeWinnetka, CAUpdated Corner Lot Multi-Unit Property with ADU + SB9 + Jr ADU in the San Fernando Valley!... |
11 beds | 7 baths | 4,012 sq.ft. |
$1,599,000 |
Airbnb cash on cash: 1.22%
|
20221 BaltarWinnetka, CAWelcome to this spacious 4-bedroom, 3-bathroom home in the heart of Winnetka, offering ove... |
4 beds | 3 baths | 3,045 sq.ft. |
$1,195,000 |
Airbnb cash on cash: 7.36%
|
20234 Cantara St #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. |
$375,000 |
Airbnb cash on cash: 8.87%
|
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. |
$410,000 |
Airbnb cash on cash: 7.63%
|
20855 Baltar StWinnetka, CAThis prime Winnetka fixer-upper at 20855 Baltar St presents a rare "diamond in the rough" ... |
3 beds | 2 baths | 1,383 sq.ft. |
$765,000 |
Airbnb cash on cash: 7.59%
|
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. |
$960,000 |
Airbnb cash on cash: 9.58%
|
Real Estate investment in Winnetka, CA
There are 70 properties for sale in the city of Winnetka . The median list price in Winnetka is $834,975 and the average price per square foot is $448. In May 2026, the average monthly cash on cash return in Winnetka is 4.00%. The average monthly rental income in Winnetka is $3,869.