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
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.	$644,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.72% Airbnb Rental Income: $5628 Traditional Rental Income: $3984 Airbnb ROI: 4.58% Traditional ROI: 3.72%
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%
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%
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.	$524,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 5.48% Airbnb Rental Income: $5628 Traditional Rental Income: $4226 Airbnb ROI: 6.04% Traditional ROI: 5.48%
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.	$335,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 1.58% Airbnb Rental Income: $2918 Traditional Rental Income: $1670 Airbnb ROI: 3.4% Traditional ROI: 1.58%
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%
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%
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 Welcome to Sherman Courts â One of Winnetka's Most Sought-After Gated Communities This ...	3 beds \| 3 baths \| 1,843 sq.ft.	$635,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.09% Airbnb Rental Income: $5628 Traditional Rental Income: $4096 Airbnb ROI: 4.77% Traditional ROI: 4.09%
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%
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.	$774,950	Airbnb cash on cash: 4.19% Traditional cash on cash: 3.42% Airbnb Rental Income: $5628 Traditional Rental Income: $3946 Airbnb ROI: 4.19% Traditional ROI: 3.42%
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%
8241 Mason Avenue #C Winnetka, CA Welcome to this beautifully remodeled 3 bedroom 2.5 bathroom Townhome offering the perfect...	3 beds \| 2 baths \| 1,424 sq.ft.	$599,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.83% Airbnb Rental Income: $5628 Traditional Rental Income: $3280 Airbnb ROI: 5.02% Traditional ROI: 2.83%
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%
8469 Fullbright Winnetka, CA Welcome to 8469 Fulbright Ave, a beautifully updated single-story home with great curb app...	3 beds \| 2 baths \| 1,375 sq.ft.	$899,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 2.45% Airbnb Rental Income: $5628 Traditional Rental Income: $3613 Airbnb ROI: 3.51% Traditional ROI: 2.45%
20146 Hartland Winnetka, CA Price Improvement! Now $849,000. Come see us at the open house this Sunday, 8/30, from 1-4...	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%
20271 Mobile Winnetka, CA Back on Market! Tucked away in this Winnetka neighborhood sits this 3 bedroom 2 bath doll ...	3 beds \| 2 baths \| 1,365 sq.ft.	$835,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 2.85% Airbnb Rental Income: $5628 Traditional Rental Income: $3671 Airbnb ROI: 3.91% Traditional ROI: 2.85%
7509 Sunnybrae Winnetka, CA Welcome to your dream homeâan incredible opportunity you donât want to miss! This beau...	3 beds \| 2 baths \| 1,496 sq.ft.	$829,900	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.26% Airbnb Rental Income: $5628 Traditional Rental Income: $3974 Airbnb ROI: 3.95% Traditional ROI: 3.26%
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%
8518 Fullbright Avenue Winnetka, CA Back on market, Opportunity Awaits in Winnetka! This single-story Ranch-style home offers ...	3 beds \| 2 baths \| 1,749 sq.ft.	$800,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 3.46% Airbnb Rental Income: $5628 Traditional Rental Income: $3983 Airbnb ROI: 4.16% Traditional ROI: 3.46%
20371 Schoenborn Winnetka, CA Beautifully upgraded Winnetka home located on a private corner lot. 3 bedrooms and 2 bathr...	3 beds \| 2 baths \| 1,538 sq.ft.	$849,500	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.03% Airbnb Rental Income: $5628 Traditional Rental Income: $3879 Airbnb ROI: 3.82% Traditional ROI: 3.03%
7032 Penfield Ave Winnetka, CA Look at this exceptional opportunity in the heart of Winneka! This versatile property feat...	5 beds \| N/A baths \| N/A	$1,169,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 0.54% Airbnb Rental Income: $5628 Traditional Rental Income: $2732 Airbnb ROI: 2.17% Traditional ROI: 0.54%
20058 Lorne St Winnetka, CA 3-bedroom, 3-bathroom home in Winnetka with approximately 1,673 square feet of living spac...	3 beds \| 3 baths \| 1,673 sq.ft.	$950,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.09% Airbnb Rental Income: $5628 Traditional Rental Income: $4374 Airbnb ROI: 3.23% Traditional ROI: 3.09%
20776 Skouras Drive Winnetka, CA Welcome to this beautifully updated single-story residence offering the perfect blend of c...	3 beds \| 2 baths \| 1,430 sq.ft.	$795,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 3.33% Airbnb Rental Income: $5628 Traditional Rental Income: $3863 Airbnb ROI: 4.2% Traditional ROI: 3.33%

Vacation Rentals in Winnetka

There are 33 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $799,450 and the average price per square foot is $465. 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 33 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

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.

$644,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $5628

Traditional Rental Income: $3984

Airbnb ROI: 4.58%

Traditional ROI: 3.72%

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%

6952 Cozycroft Avenue

Winnetka, CA

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%

8430 Winnetka Avenue #20

Winnetka, CA

3 beds | 3 baths | 1,587 sq.ft.

$524,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $5628

Traditional Rental Income: $4226

Airbnb ROI: 6.04%

Traditional ROI: 5.48%

20234 Cantara #214

Winnetka, CA

2 beds | 2 baths | 925 sq.ft.

$335,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $2918

Traditional Rental Income: $1670

Airbnb ROI: 3.4%

Traditional ROI: 1.58%

20327 Saticoy Street #102

Winnetka, CA

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%

20309 Roscoe

Winnetka, CA

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%