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 |
|---|---|---|---|
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. |
$399,500 |
Airbnb cash on cash: 4.17%
|
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%
|
20146 Cohasset St #5Winnetka, CA
|
3 beds | 2 baths | 1,340 sq.ft. |
$459,000 |
Airbnb cash on cash: 6.87%
|
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. |
$249,000 |
Airbnb cash on cash: 5.32%
|
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%
|
7509 Winnetka AveWinnetka, CAGATED COMMUNITY - DUAL EN-SUITE BEDROOMS - QUARTZ COUNTERTOPS - RECENTLY INSTALLED AC - PR... |
2 beds | 2 baths | 1,337 sq.ft. |
$529,000 |
Airbnb cash on cash: 3.07%
|
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. |
$846,600 |
Airbnb cash on cash: 5.76%
|
8340 Penfield Ave #35Winnetka, CAGated Private Townhouse community, only 37 units. This townhome is at the back of the comp... |
3 beds | 2 baths | 1,282 sq.ft. |
$640,000 |
Airbnb cash on cash: 4.27%
|
7708 Oakdale AveWinnetka, CA
|
4 beds | 3 baths | 2,294 sq.ft. |
$950,000 |
Airbnb cash on cash: 4.86%
|
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%
|
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. |
$499,000 |
Airbnb cash on cash: 5.64%
|
20155 Keswick St #107Winnetka, CAAmazing well maintained 2-story townhouse, 2 bedrooms and 1 1/2 bathrooms. This cozy unit... |
2 beds | 2 baths | 1,040 sq.ft. |
$475,000 |
Airbnb cash on cash: 3.17%
|
19932 Sherman Way #BWinnetka, CA
|
3 beds | 3 baths | 1,766 sq.ft. |
$645,000 |
Airbnb cash on cash: 3.51%
|
20428 Roscoe BlvdWinnetka, CAWelcome to 20428 Roscoe Blvd. A Thoughtfully Updated Home in the Heart of the Valley Step ... |
3 beds | 2 baths | 1,380 sq.ft. |
$838,800 |
Airbnb cash on cash: 3.51%
|
7445 Oakdale AveWinnetka, 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: 1.45%
|
7032 Penfield AveWinnetka, CAExceptional opportunity in the heart of Winneka! This versatile property features a beauti... |
5 beds | N/A baths | N/A |
$1,169,000 |
Airbnb cash on cash: 1.9%
|
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. |
$939,900 |
Airbnb cash on cash: 4.93%
|
20253 Keswick St #323Winnetka, CA20253 Keswick St #323, Los Angeles, CA 91306 | Condo/Coop |
2 beds | 2 baths | 880 sq.ft. |
$465,000 |
Airbnb cash on cash: 3.34%
|
6952 Cozycroft AveWinnetka, CAFixer-upper Opportunity in a Beautiful Neighborhood. Looking for your next project in a pr... |
4 beds | 3 baths | 2,251 sq.ft. |
$1,395,000 |
Airbnb cash on cash: 2.75%
|
20737 Roscoe Blvd #203Winnetka, CA
|
2 beds | 3 baths | 1,580 sq.ft. |
$559,990 |
Airbnb cash on cash: 2.52%
|
20235 Keswick St #212Winnetka, CA
|
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. |
$1,350,000 |
Airbnb cash on cash: 0.51%
|
20531 Covello StWinnetka, CALocation, Location, Location!!!! This property includes a three bedroom two bath house, ... |
4 beds | 3 baths | 1,693 sq.ft. |
$999,000 |
Airbnb cash on cash: 4.13%
|
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. |
$1,495,000 |
Airbnb cash on cash: 3.24%
|
8430 Winnetka Ave #20Winnetka, CARare opportunity with unlimited potential in this spacious and inviting townhome! Offering... |
3 beds | 3 baths | 1,587 sq.ft. |
$549,000 |
Airbnb cash on cash: 5.12%
|
19950 Sherman Way #AWinnetka, CAArchitecturally distinctive and filled with natural light, this 3-bedroom, 3.5-bath gated ... |
3 beds | 3 baths | 1,860 sq.ft. |
$519,900 |
Airbnb cash on cash: 4.97%
|
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%
|
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. |
$1,495,000 |
Airbnb cash on cash: 2.44%
|
20327 Saticoy St #102Winnetka, CAIn the heart of Winnetka, this well-maintained 1-bedroom condo offers a secured entrance a... |
1 beds | 1 baths | 640 sq.ft. |
$299,999 |
Airbnb cash on cash: 2.2%
|
8353 Lurline AveWinnetka, CA8353 Lurline Ave, Winnetka, CA 91306 | Single Family Residential |
3 beds | 2 baths | 1,482 sq.ft. |
$869,000 |
Airbnb cash on cash: 3.33%
|
20458 MaldenWinnetka, CAGreat Home needs updating Great location |
4 beds | 2 baths | 1,572 sq.ft. |
$800,000 |
Airbnb cash on cash: 6.09%
|
7101 Oso Ave #16Winnetka, CAMotivated Seller: Welcome to 7101 Oso Ave #16, a charming free standing detached home tuck... |
3 beds | 3 baths | 1,926 sq.ft. |
$779,999 |
Airbnb cash on cash: 3.31%
|
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: 3.77%
|
7211 Cozycroft #32Winnetka, CAHOT HOT HOT...DO NOT MISS THIS ONE! SELLER WILL COVER BUYERS' FIRST 6 MONTHS OF HOA PAYM... |
2 beds | 2 baths | 1,033 sq.ft. |
$399,000 |
Airbnb cash on cash: 3.51%
|
7640 Oso #318Winnetka, CA
|
2 beds | 2 baths | 899 sq.ft. |
$420,000 |
Airbnb cash on cash: 4.21%
|
20253 Keswick St #318Winnetka, CAGreat Third Floor 2 + 2 Condominium with Open Tree-top View and no one above. Move in read... |
2 beds | 2 baths | 880 sq.ft. |
$418,950 |
Airbnb cash on cash: 3.9%
|
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: 4.83%
|
20134 Leadwell #126Winnetka, CAFully updated first-floor condo with a rare oversized private patio in a quiet gated Winne... |
2 beds | 1 baths | 786 sq.ft. |
$410,000 |
Airbnb cash on cash: 3.93%
|
Real Estate investment in Winnetka, CA
There are 93 properties for sale in the city of Winnetka . The median list price in Winnetka is $799,000 and the average price per square foot is $449. In July 2026, the average monthly cash on cash return in Winnetka is 4.00%. The average monthly rental income in Winnetka is $3,916.