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: 3.33%
|
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. |
$409,900 |
Airbnb cash on cash: 4.02%
|
20439 Malden StWinnetka, CACharming single-story home in Winnetka featuring 3 bedrooms and 2 bathrooms with recent up... |
3 beds | 2 baths | 2,085 sq.ft. |
$799,900 |
Airbnb cash on cash: 3.76%
|
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: 5.05%
|
20737 Roscoe Blvd #704Winnetka, CAStunning Move-In Ready Townhouse, located towards the back of the Windsor Park neighborhoo... |
2 beds | 3 baths | 1,580 sq.ft. |
$585,000 |
Airbnb cash on cash: 2.66%
|
20606 Skouras DrWinnetka, CAThis inviting single-story home in a quiet Winnetka neighborhood offers 4 bedrooms and 2 b... |
4 beds | 2 baths | 1,362 sq.ft. |
$899,000 |
Airbnb cash on cash: 5.37%
|
20126 Runnymede St #22Winnetka, CALocated in a well-established Winnetka townhome community, this stunning corner unit offer... |
3 beds | 3 baths | 1,615 sq.ft. |
$629,999 |
Airbnb cash on cash: 4.34%
|
8341 Delco AveWinnetka, CAGracious living is exemplified in this reimagined 4+ 3 mid century modern home with a ONE ... |
5 beds | 4 baths | 2,000 sq.ft. |
$1,040,000 |
Airbnb cash on cash: 6.08%
|
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. |
$525,000 |
Airbnb cash on cash: 5.28%
|
20428 Roscoe BoulevardWinnetka, 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: 3.16%
|
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: 1.29%
|
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: N/A
|
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: 4.86%
|
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: 3.53%
|
20851 Community Street 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: 4.17%
|
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: 2.23%
|
20235 Keswick St #212Winnetka, CAWelcome to this beautifully updated condo located at 20235 Keswick Street, Unit 212 in Win... |
2 beds | 2 baths | 1,021 sq.ft. |
$499,000 |
Airbnb cash on cash: 3.15%
|
7754 Delco AveWinnetka, CA7754 Delco Ave, Los Angeles, CA 91306 | Multi Family |
8 beds | 5 baths | 2,980 sq.ft. |
$1,400,000 |
Airbnb cash on cash: 0.43%
|
19918 Kittridge StWinnetka, CA3 bedroom/1 bath residence offers tremendous potential for those with a vision to transfor... |
8 beds | 6 baths | 3,395 sq.ft. |
$1,725,000 |
Airbnb cash on cash: 2.58%
|
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: 3.08%
|
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: 4.2%
|
8430 Winnetka Ave #20Winnetka, CARare opportunity with unlimited potential in this spacious and inviting townhome! Offering... |
3 beds | 3 baths | 1,587 sq.ft. |
$589,000 |
Airbnb cash on cash: 4.65%
|
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: 3.02%
|
20329 Stagg StWinnetka, CA** NEWLY REDUCED! TOP-OF-THE-LINE 2025 construction. A newly constructed Spanish-style mas... |
5 beds | 5 baths | 3,700 sq.ft. |
$1,695,000 |
Airbnb cash on cash: 2.47%
|
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: 3.02%
|
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: 4.89%
|
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: 2.65%
|
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: 2.31%
|
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: 3.48%
|
20458 MaldenWinnetka, CAGreat Home needs updating Great location |
4 beds | 2 baths | 1,572 sq.ft. |
$800,000 |
Airbnb cash on cash: 6.09%
|
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: 2.35%
|
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: 0.3%
|
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: 3%
|
20309 RoscoeWinnetka, CABeautifully updated 3-bedroom, 2-bath home featuring modern upgrades throughout. This move... |
3 beds | 2 baths | 1,321 sq.ft. |
$859,000 |
Airbnb cash on cash: 3.39%
|
19843 Enadia RiseWinnetka, CA
|
6 beds | 5 baths | 2,454 sq.ft. |
$1,075,000 |
Airbnb cash on cash: 5.2%
|
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: 3.51%
|
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: 2.93%
|
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: 2.92%
|
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: 4.21%
|
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: 0.26%
|
Real Estate investment in Winnetka, CA
There are 94 properties for sale in the city of Winnetka . The median list price in Winnetka is $799,975 and the average price per square foot is $432. In June 2026, the average monthly cash on cash return in Winnetka is 4.00%. The average monthly rental income in Winnetka is $3,879.