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 |
|---|---|---|---|
7020 Oakdale AveWinnetka, CAOne of the most versatile homes in Winnetka remodeled, income-producing, and designed for ... |
4 beds | 2 baths | 1,290 sq.ft. |
$1,000,000 |
Airbnb cash on cash: 9.13%
|
20234 Cantara St #136Winnetka, CAWelcome to this charming studio that offers a warm, inviting ambiance from the moment you ... |
N/A beds | 1 baths | 444 sq.ft. |
$299,000 |
Airbnb cash on cash: 5.14%
|
20134 Leadwell Street #332Winnetka, CAWelcome to this move-in ready top-floor unit located in the heart of Winnetka. Inside, the... |
2 beds | 2 baths | 884 sq.ft. |
$399,000 |
Airbnb cash on cash: 7.89%
|
8846 Laramie AvenueWinnetka, CAINCREDIBLE PRICE! This is a rare opportunity in a prime location! Itâs not often you fin... |
4 beds | 3 baths | 2,399 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 7.71%
|
20134 Leadwell Street #159Winnetka, CADonât miss this rare opportunity to own a premier ground-floor, 2-bedroom, 2-bathroom re... |
2 beds | 2 baths | 884 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.43%
|
8620 Lubao AvenueWinnetka, CAThis exceptional income property offers the potential to generate approximately $10,900 (!... |
7 beds | 7 baths | 3,280 sq.ft. |
$1,795,000 |
Airbnb cash on cash: 5.89%
|
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: 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. |
$999,000 |
Airbnb cash on cash: 9.14%
|
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%
|
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: 8.37%
|
20308 Mobile StWinnetka, CAAmazing opportunity to own a newly renovated, immaculate, move in ready home in Winnetka's... |
5 beds | 4 baths | 2,500 sq.ft. |
$1,295,000 |
Airbnb cash on cash: 8.05%
|
20235 Keswick Street #212Winnetka, CAWelcome to this beautifully updated condo located at 20235 Keswick Street, Unit 212 in Win... |
2 beds | 2 baths | 1,021 sq.ft. |
$535,000 |
Airbnb cash on cash: 5.67%
|
8467 Penfield AvenueWinnetka, CAThe front of the home is beautifully manicured and features impressive Roman-style pillars... |
3 beds | 3 baths | 2,276 sq.ft. |
$939,000 |
Airbnb cash on cash: 5.87%
|
19844 Hemmingway StreetWinnetka, CA**POOL, SINGLE LEVEL, 4-BED** Stop scrolling â this is the one! Welcome home to 19844 He... |
4 beds | 2 baths | 1,602 sq.ft. |
$949,000 |
Airbnb cash on cash: 9.71%
|
7640 Oso Ave #217Winnetka, CA7640 Oso Ave #217, Los Angeles, CA 91306 | Condo/Coop |
1 beds | 1 baths | 648 sq.ft. |
$285,000 |
Airbnb cash on cash: 5.6%
|
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 Avenue #316Winnetka, CAThis incredible 1+1 freshly painted penthouse unit with vaulted ceiling is very bright wit... |
1 beds | 1 baths | 648 sq.ft. |
$315,990 |
Airbnb cash on cash: 4.91%
|
20329 Stagg StWinnetka, CAA newly constructed Spanish-style masterpiece offering top-of-the-line 2025 construction -... |
5 beds | 5 baths | 3,700 sq.ft. |
$1,795,000 |
Airbnb cash on cash: 5.2%
|
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 Avenue #6Winnetka, CAWelcome to Kelvin Court, a gated and well maintained community where comfort meets conveni... |
3 beds | 2 baths | 1,488 sq.ft. |
$589,000 |
Airbnb cash on cash: 9.42%
|
20656 Acre StWinnetka, CAIncredible opportunity to own a newly remodeled single-family pool home in the highly desi... |
3 beds | 2 baths | 1,392 sq.ft. |
$935,000 |
Airbnb cash on cash: 5.9%
|
20258 Cohasset St unit: 4Winnetka, CABeautiful bright 2 level townhouse with back patio. 2 bedroom and 1 1/2 bath. Central Heat... |
2 beds | 2 baths | 1,050 sq.ft. |
$438,000 |
Airbnb cash on cash: 7.44%
|
7414 QuartzWinnetka, CAThis beautiful home in nestled on one of Winnetkaâs most sought-after family neighborhoo... |
3 beds | 2 baths | 1,588 sq.ft. |
$950,000 |
Airbnb cash on cash: 5.78%
|
20737 Roscoe #704Winnetka, CAFor a private Showing Contact Regina at 1(818) 772-1562 |
2 beds | 3 baths | 1,580 sq.ft. |
$620,000 |
Airbnb cash on cash: 4.56%
|
20247 LanarkWinnetka, CAâCharming triplex in Winnetka â this well-maintained property offers a rare opportunit... |
14 beds | 6 baths | 2,520 sq.ft. |
$1,900,000 |
Airbnb cash on cash: 5.35%
|
20819 W Seasons LaneWinnetka, 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%
|
20528 Hamlin StreetWinnetka, CAOutstanding Modern Masterpiecce | Welcome To This 2 Homes In One Lot Beautifully Designed ... |
5 beds | 3 baths | 1,788 sq.ft. |
$1,229,777 |
Airbnb cash on cash: 4.39%
|
20327 Saticoy Street #102Winnetka, CAIn the heart of Winnetka, this well-maintained 1-bedroom condo offers a secured entrance a... |
1 beds | 1 baths | 640 sq.ft. |
$289,999 |
Airbnb cash on cash: 5.97%
|
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%
|
19950 Sherman Way #A #AWinnetka, CASpectacular 3BD/3.5BA Townhouse corner unit highlighting refined finishes and effortless l... |
3 beds | 4 baths | 1,860 sq.ft. |
$549,000 |
Airbnb cash on cash: 9.59%
|
20010 Eccles StreetWinnetka, CAWelcome to this beautifully updated home, completely reimagined with quality upgrades thro... |
3 beds | 2 baths | 1,407 sq.ft. |
$834,900 |
Airbnb cash on cash: 6.66%
|
20120 Runnymede Street #17Winnetka, CAWelcome to this charming move-in ready townhome located in a quiet and well-maintained com... |
3 beds | 3 baths | 1,329 sq.ft. |
$579,000 |
Airbnb cash on cash: 9.59%
|
20252 Archwood StWinnetka, CAMore photos coming soon! Investor opportunity in the heart of Winnetka, California! This s... |
3 beds | 2 baths | 1,543 sq.ft. |
$775,000 |
Airbnb cash on cash: 7.02%
|
7101 Oso Ave #16Winnetka, CAWelcome to 7101 Oso Ave #16, a charming home tucked inside an intimate 16-home private cul... |
3 beds | 3 baths | 1,926 sq.ft. |
$850,000 |
Airbnb cash on cash: 6.11%
|
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. |
$899,000 |
Airbnb cash on cash: 6.21%
|
20211 Schoolcraft StWinnetka, CA20211 Schoolcraft St, Winnetka, CA 91306 | Single Family Residential |
3 beds | 2 baths | 1,754 sq.ft. |
$760,000 |
Airbnb cash on cash: 7.65%
|
7211 Cozycroft #32Winnetka, CA7211 Cozycroft #32, Winnetka, CA 91306 | Condo/Coop |
2 beds | 2 baths | 1,033 sq.ft. |
$455,900 |
Airbnb cash on cash: 6.78%
|
6947 Sunnybrae AveWinnetka, CAWelcome to a quiet peaceful Winnetka cul-de-sac. If your are seeking location convenience,... |
3 beds | 2 baths | 1,201 sq.ft. |
$849,990 |
Airbnb cash on cash: 6.66%
|
Real Estate investment in Winnetka, CA
There are 54 properties for sale in the city of Winnetka . The median list price in Winnetka is $868,000 and the average price per square foot is $459. In March 2026, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $3,956.