Airbnb Properties for Sale in Winnetka, CA

Looking for a vacation rental investment in Winnetka, CA with high ROI ?

Explore a range of newly added short-term rental homes in Winnetka, CA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winnetka, CA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
19803 Bassett St Winnetka, CA 19803 Bassett St, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,417 sq.ft.	$849,990	Airbnb cash on cash: 3.92% Traditional cash on cash: 3.4% Airbnb Rental Income: $5628 Traditional Rental Income: $4093 Airbnb ROI: 3.92% Traditional ROI: 3.4%
20146 Cohasset Street #5 Winnetka, CA Welcome 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% Traditional cash on cash: 5.94% Airbnb Rental Income: $5628 Traditional Rental Income: $3806 Airbnb ROI: 7.56% Traditional ROI: 5.94%
19928 Chase Street #23 Winnetka, CA Move-in ready 3-bedroom, 3-bathroom townhome situated on a quiet residential street surrou...	3 beds \| 3 baths \| 1,459 sq.ft.	$620,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 3.9% Airbnb Rental Income: $5628 Traditional Rental Income: $3984 Airbnb ROI: 4.8% Traditional ROI: 3.9%
8340 Penfield Ave #35 Winnetka, CA Welcome 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% Traditional cash on cash: 2.07% Airbnb Rental Income: $5628 Traditional Rental Income: $2851 Airbnb ROI: 4.9% Traditional ROI: 2.07%
20134 Leadwell St #334 Winnetka, CA Back On Market. SOLD with Multiple Offers last time! Buyer did not perform. This beautiful...	3 beds \| 2 baths \| 1,113 sq.ft.	$475,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 3.44% Airbnb Rental Income: $5628 Traditional Rental Income: $3064 Airbnb ROI: 6.68% Traditional ROI: 3.44%
20358 Strathern Street Winnetka, CA Welcome to this beautifully updated single-story ranch home in a highly sought-after pocke...	3 beds \| 2 baths \| 2,256 sq.ft.	$1,275,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 0.71% Airbnb Rental Income: $5628 Traditional Rental Income: $2344 Airbnb ROI: 2.53% Traditional ROI: 0.71%
20428 Roscoe Blvd Winnetka, CA Welcome 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: 3.89% Traditional cash on cash: 1.44% Airbnb Rental Income: $5628 Traditional Rental Income: $2592 Airbnb ROI: 3.89% Traditional ROI: 1.44%
7445 Oakdale Ave Winnetka, CA Exceptional 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% Traditional cash on cash: 0.82% Airbnb Rental Income: $5628 Traditional Rental Income: $3313 Airbnb ROI: 1.63% Traditional ROI: 0.82%
20234 Cantara St #229 Winnetka, CA Charming 1-bedroom unit featuring abundance of natural light, a tastefully updated bathroo...	1 beds \| 1 baths \| 744 sq.ft.	$379,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.86% Airbnb Rental Income: $2613 Traditional Rental Income: $1972 Airbnb ROI: 1.9% Traditional ROI: 1.86%
6952 Cozycroft Avenue Winnetka, CA Welcome 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% Traditional cash on cash: 0.83% Airbnb Rental Income: $4489 Traditional Rental Income: $3449 Airbnb ROI: 0.91% Traditional ROI: 0.83%
20112 Runnymede St #3 Winnetka, CA WELCOME TO THIS BEAUTIFUL 3 BEDROOM WITH 2.5 BATH TOWNHOME IN A GATED COMMUNITY. LIVING R...	3 beds \| 2 baths \| 1,329 sq.ft.	$599,999	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.26% Airbnb Rental Income: $5628 Traditional Rental Income: $3963 Airbnb ROI: 5.22% Traditional ROI: 4.26%
8430 Winnetka Avenue #20 Winnetka, CA Price Reduction!!! Rare opportunity with unlimited potential in this spacious and inviting...	3 beds \| 3 baths \| 1,587 sq.ft.	$509,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 5.69% Airbnb Rental Income: $5628 Traditional Rental Income: $4226 Airbnb ROI: 6.27% Traditional ROI: 5.69%
20234 Cantara #214 Winnetka, CA Welcome home to this bright and spacious 925 sq ft condo featuring a highly desirable open...	2 beds \| 2 baths \| 925 sq.ft.	$320,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 1.73% Airbnb Rental Income: $2918 Traditional Rental Income: $1670 Airbnb ROI: 3.63% Traditional ROI: 1.73%
20327 Saticoy Street #102 Winnetka, CA An 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% Traditional cash on cash: 4.18% Airbnb Rental Income: $2613 Traditional Rental Income: $1959 Airbnb ROI: 4.3% Traditional ROI: 4.18%
8353 Lurline Ave Winnetka, CA 8353 Lurline Ave, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,482 sq.ft.	$849,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.33% Airbnb Rental Income: $5628 Traditional Rental Income: $3325 Airbnb ROI: 3.82% Traditional ROI: 2.33%
20309 Roscoe Winnetka, CA Beautifully 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% Traditional cash on cash: 3.42% Airbnb Rental Income: $5628 Traditional Rental Income: $3946 Airbnb ROI: 4.17% Traditional ROI: 3.42%
20134 Leadwell #307 Winnetka, CA Welcome to this beautifully renovated corner unit, thoughtfully updated with comfort, styl...	3 beds \| 2 baths \| 1,113 sq.ft.	$519,900	Airbnb cash on cash: 5.96% Traditional cash on cash: 3.04% Airbnb Rental Income: $5628 Traditional Rental Income: $3083 Airbnb ROI: 5.96% Traditional ROI: 3.04%
20230 Keswick #3 Winnetka, CA Home 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% Traditional cash on cash: 3.26% Airbnb Rental Income: $5628 Traditional Rental Income: $3426 Airbnb ROI: 4.92% Traditional ROI: 3.26%
20146 Cohasset #11 Winnetka, CA Welcome 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% Traditional cash on cash: 3.34% Airbnb Rental Income: $5628 Traditional Rental Income: $2952 Airbnb ROI: 6.69% Traditional ROI: 3.34%
20224 Sherman #48 Winnetka, CA MOTIVATED SELLER! Welcome to Sherman Courts â One of Winnetka's Most Sought-After Gated ...	3 beds \| 3 baths \| 1,843 sq.ft.	$625,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 4.18% Airbnb Rental Income: $5628 Traditional Rental Income: $4096 Airbnb ROI: 4.88% Traditional ROI: 4.18%
20234 Cantara #342 Winnetka, CA This 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% Traditional cash on cash: 2.31% Airbnb Rental Income: $2393 Traditional Rental Income: $1581 Airbnb ROI: 3.26% Traditional ROI: 2.31%
20247 Parthenia Winnetka, CA 20247 Parthenia, Winnetka, CA 91306 \| Single Family Residential	6 beds \| 3 baths \| 2,180 sq.ft.	$1,090,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3.01% Airbnb Rental Income: $8665 Traditional Rental Income: $4921 Airbnb ROI: 5.09% Traditional ROI: 3.01%
20457 Schoolcraft Street Winnetka, CA Welcome home to 20457 Schoolcraft St, a refreshed single-story in the heart of central Win...	3 beds \| 2 baths \| 1,225 sq.ft.	$749,950	Airbnb cash on cash: 4.37% Traditional cash on cash: 3.57% Airbnb Rental Income: $5628 Traditional Rental Income: $3946 Airbnb ROI: 4.37% Traditional ROI: 3.57%
8231 Mason Avenue #C Winnetka, CA Welcome 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% Traditional cash on cash: 3.3% Airbnb Rental Income: $5628 Traditional Rental Income: $3314 Airbnb ROI: 5.61% Traditional ROI: 3.3%
20327 Saticoy #309 Winnetka, CA Condo 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% Traditional cash on cash: 3.15% Airbnb Rental Income: $2613 Traditional Rental Income: $1959 Airbnb ROI: 3.24% Traditional ROI: 3.15%
20310 Londelius Winnetka, CA After 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% Traditional cash on cash: 2.89% Airbnb Rental Income: $5628 Traditional Rental Income: $3770 Airbnb ROI: 3.82% Traditional ROI: 2.89%
20146 Hartland Winnetka, CA Price Improvement! Now $849,000. Come see us at the open house this Sunday, 9/13, from 2-4...	3 beds \| 2 baths \| 1,202 sq.ft.	$849,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.68% Airbnb Rental Income: $5628 Traditional Rental Income: $3603 Airbnb ROI: 3.82% Traditional ROI: 2.68%
7509 Sunnybrae Winnetka, CA Welcome to your dream homeâan incredible opportunity you donât want to miss! This beau...	3 beds \| 2 baths \| 1,216 sq.ft.	$799,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 3.46% Airbnb Rental Income: $5628 Traditional Rental Income: $3974 Airbnb ROI: 4.17% Traditional ROI: 3.46%
8012 Comanche Winnetka, CA Why settle for ordinary when you can have retro-inspired charm, modern updates, and your o...	3 beds \| 2 baths \| 1,733 sq.ft.	$949,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.43% Airbnb Rental Income: $5628 Traditional Rental Income: $3790 Airbnb ROI: 3.24% Traditional ROI: 2.43%
8043 Sunnybrae Winnetka, CA Welcome to 8043 Sunnybrae Avenue, a beautifully updated single-story home tucked away on a...	3 beds \| 2 baths \| 1,219 sq.ft.	$780,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3.33% Airbnb Rental Income: $5628 Traditional Rental Income: $3787 Airbnb ROI: 4.31% Traditional ROI: 3.33%
7907 Casaba Winnetka, CA 7907 Casaba, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 4 baths \| 2,998 sq.ft.	$1,185,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 4.01% Airbnb Rental Income: $8665 Traditional Rental Income: $6450 Airbnb ROI: 4.54% Traditional ROI: 4.01%
20562 Skouras Winnetka, CA Welcome to this stylish 3-bedroom home in Winnetka, offering a unique modern feel with an ...	3 beds \| 2 baths \| 1,362 sq.ft.	$949,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 2.56% Airbnb Rental Income: $5628 Traditional Rental Income: $4201 Airbnb ROI: 2.9% Traditional ROI: 2.56%
8612 Mason Winnetka, CA 8612 Mason, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 4 baths \| 2,518 sq.ft.	$1,150,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 3.8% Airbnb Rental Income: $8665 Traditional Rental Income: $6033 Airbnb ROI: 4.73% Traditional ROI: 3.8%
8132 Hatillo Winnetka, CA 8132 Hatillo, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 3 baths \| 1,830 sq.ft.	$1,099,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 1.78% Airbnb Rental Income: $8665 Traditional Rental Income: $3708 Airbnb ROI: 5.03% Traditional ROI: 1.78%
7746 Sunnybrae Winnetka, CA Welcome to this beautifully remodeled property featuring a 4-bedroom, 3-bath main residenc...	5 beds \| 4 baths \| 2,049 sq.ft.	$1,175,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 4.35% Airbnb Rental Income: $8665 Traditional Rental Income: $6055 Airbnb ROI: 5.24% Traditional ROI: 4.35%
20259 Ingomar St Winnetka, CA 20259 Ingomar St, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 3 baths \| 2,477 sq.ft.	$849,995	Airbnb cash on cash: 7.01% Traditional cash on cash: 4.32% Airbnb Rental Income: $8665 Traditional Rental Income: $4899 Airbnb ROI: 7.01% Traditional ROI: 4.32%
20737 Roscoe Boulevard #204 Winnetka, CA Set within the gated Windsor Park community, this south-facing end-unit townhome offers a ...	3 beds \| 2 baths \| 1,641 sq.ft.	$575,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 4.52% Airbnb Rental Income: $5628 Traditional Rental Income: $4075 Airbnb ROI: 5.32% Traditional ROI: 4.52%
6903 Winnetka Winnetka, CA First Time on the Market in Over 50 Years! Discover an exceptional value-add opportunity i...	3 beds \| 2 baths \| 1,215 sq.ft.	$670,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.33% Airbnb Rental Income: $5628 Traditional Rental Income: $3896 Airbnb ROI: 5.3% Traditional ROI: 4.33%

Vacation Rentals in Winnetka

There are 48 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $835,000 and the average price per square foot is $471. The cash on cash return on vacation rentals in Winnetka is 3.00%. The average monthly short term rental income in Winnetka is $4,489.

Winnetka, CA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 48 Airbnb properties available for sale in Winnetka.

In 2026, the best neighborhood to buy short term rental property is Winnetka.

In September 2026, the average Airbnb occupancy rate in Winnetka is 34%.

Airbnb data on vacation rentals in Winnetka, CA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winnetka, CA market insights, guest information and booking details, seasonality trends and historical Winnetka, CA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winnetka, CA

19803 Bassett St

Winnetka, CA

3 beds | 2 baths | 1,417 sq.ft.

$849,990

Airbnb cash on cash: 3.92%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $5628

Traditional Rental Income: $4093

Airbnb ROI: 3.92%

Traditional ROI: 3.4%

20146 Cohasset Street #5

Winnetka, CA

3 beds | 2 baths | 1,340 sq.ft.

$459,000

Airbnb cash on cash: 7.56%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $5628

Traditional Rental Income: $3806

Airbnb ROI: 7.56%

Traditional ROI: 5.94%

19928 Chase Street #23

Winnetka, CA

3 beds | 3 baths | 1,459 sq.ft.

$620,000

Airbnb cash on cash: 4.8%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $5628

Traditional Rental Income: $3984

Airbnb ROI: 4.8%

Traditional ROI: 3.9%

8340 Penfield Ave #35

Winnetka, CA

3 beds | 2 baths | 1,282 sq.ft.

$625,000

Airbnb cash on cash: 4.9%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $5628

Traditional Rental Income: $2851

Airbnb ROI: 4.9%

Traditional ROI: 2.07%

20134 Leadwell St #334

Winnetka, CA

3 beds | 2 baths | 1,113 sq.ft.

$475,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5628

Traditional Rental Income: $3064

Airbnb ROI: 6.68%

Traditional ROI: 3.44%

20358 Strathern Street

Winnetka, CA

3 beds | 2 baths | 2,256 sq.ft.

$1,275,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $5628

Traditional Rental Income: $2344

Airbnb ROI: 2.53%

Traditional ROI: 0.71%

20428 Roscoe Blvd

Winnetka, CA

3 beds | 2 baths | 1,380 sq.ft.

$838,800

Airbnb cash on cash: 3.89%

Traditional cash on cash: 1.44%

Airbnb Rental Income: $5628

Traditional Rental Income: $2592

Airbnb ROI: 3.89%

Traditional ROI: 1.44%

7445 Oakdale Ave

Winnetka, CA

6 beds | 4 baths | 2,570 sq.ft.

$1,750,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $5628

Traditional Rental Income: $3313

Airbnb ROI: 1.63%