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
20155 Keswick Street #209 Winnetka, CA Welcome to this beautifully updated 2 bedroom 1 1/2 bathroom townhome offering stylish com...	2 beds \| 2 baths \| 1,125 sq.ft.	$475,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 4.08% Airbnb Rental Income: $5460 Traditional Rental Income: $3209 Airbnb ROI: 6.67% Traditional ROI: 4.08%
20134 Leadwell St #133 Winnetka, CA 20134 Leadwell St #133, Winnetka, CA 91306 \| Condo/Coop	2 beds \| 2 baths \| 884 sq.ft.	$399,000	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.31% Airbnb Rental Income: $5460 Traditional Rental Income: $2849 Airbnb ROI: 8.35% Traditional ROI: 4.31%
20216 Roscoe Boulevard #19 Winnetka, CA Step into this freshly updated 2-bedroom, 3-bath condo. Featuring new flooring and fresh p...	2 beds \| 1 baths \| 1,133 sq.ft.	$484,000	Airbnb cash on cash: 6.81% Traditional cash on cash: 3.32% Airbnb Rental Income: $5460 Traditional Rental Income: $2779 Airbnb ROI: 6.81% Traditional ROI: 3.32%
20352 Keswick Street Winnetka, CA Welcome home to this beautifully updated single-story residence in the heart of Winnetka. ...	4 beds \| 3 baths \| 2,178 sq.ft.	$999,000	Airbnb cash on cash: 9.15% Traditional cash on cash: 1.31% Airbnb Rental Income: $12488 Traditional Rental Income: $2936 Airbnb ROI: 9.15% Traditional ROI: 1.31%
19947 Cantara Street Winnetka, CA Price Improvement.!!!!!Welcome to your private resort style retreat, tucked away on a sere...	4 beds \| 3 baths \| 1,924 sq.ft.	$1,015,000	Airbnb cash on cash: 8.94% Traditional cash on cash: 3.28% Airbnb Rental Income: $12488 Traditional Rental Income: $4865 Airbnb ROI: 8.94% Traditional ROI: 3.28%
20737 Roscoe Boulevard #301 Winnetka, CA BUY THIS TOWNHOUSE WITH 1% DOWN-SEE SUPPLEMENTS. The seller is willing to negotiate either...	3 beds \| 3 baths \| 1,641 sq.ft.	$658,780	Airbnb cash on cash: 8.18% Traditional cash on cash: 4.07% Airbnb Rental Income: $8334 Traditional Rental Income: $4230 Airbnb ROI: 8.18% Traditional ROI: 4.07%
8231 Mason Avenue #E Winnetka, CA Tucked away in a peaceful and well-maintained Winnetka community, this bright and spacious...	2 beds \| 2 baths \| 1,202 sq.ft.	$549,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 2.71% Airbnb Rental Income: $5460 Traditional Rental Income: $2993 Airbnb ROI: 5.37% Traditional ROI: 2.71%
20254 Stagg Street Winnetka, CA Welcome to this beautiful recently renovated home that blends timeless character with mode...	4 beds \| 3 baths \| 2,288 sq.ft.	$948,500	Airbnb cash on cash: 9.71% Traditional cash on cash: 2.03% Airbnb Rental Income: $12488 Traditional Rental Income: $3433 Airbnb ROI: 9.71% Traditional ROI: 2.03%
20253 Keswick St #326 Winnetka, CA NO ONE ABOVE YOU. ALL APPLIANCES INCLUDED. $10,938 CREDIT FOR FIRST TIME HOME BUYERS. Char...	1 beds \| 1 baths \| 630 sq.ft.	$345,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 2.1% Airbnb Rental Income: $3229 Traditional Rental Income: $1943 Airbnb ROI: 3.83% Traditional ROI: 2.1%
20341 Schoenborn Street Winnetka, CA MAJOR PRICE IMPROVEMENT! Fully remodeled from top to bottom, this beautifully designed W...	3 beds \| 2 baths \| 1,330 sq.ft.	$899,900	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.29% Airbnb Rental Income: $8334 Traditional Rental Income: $4038 Airbnb ROI: 6.54% Traditional ROI: 3.29%
19714 Lull Street Winnetka, CA This two-story home is on a quiet cul-de-sac in a charming neighborhood in Winnetka. It fe...	4 beds \| 3 baths \| 1,974 sq.ft.	$939,000	Airbnb cash on cash: 9.73% Traditional cash on cash: 4.19% Airbnb Rental Income: $12488 Traditional Rental Income: $5379 Airbnb ROI: 9.73% Traditional ROI: 4.19%
19910 Cantara Street Winnetka, CA Beautiful 2 story home in Winnetka. This well maintained home features hardwood floors and...	4 beds \| 3 baths \| 2,140 sq.ft.	$949,000	Airbnb cash on cash: 9.71% Traditional cash on cash: 2.88% Airbnb Rental Income: $12488 Traditional Rental Income: $4184 Airbnb ROI: 9.71% Traditional ROI: 2.88%
5853 Keokuk Ave Winnetka, CA Major Price Adjustment! Exceptional value in one of Woodland Hillsâ highly sought-after ...	4 beds \| 3 baths \| 2,008 sq.ft.	$1,695,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 1.01% Airbnb Rental Income: $12488 Traditional Rental Income: $4442 Airbnb ROI: 4.68% Traditional ROI: 1.01%
7812 Fairchild Avenue Winnetka, CA Welcome 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% Traditional cash on cash: 2.66% Airbnb Rental Income: $8334 Traditional Rental Income: $3893 Airbnb ROI: 5.98% Traditional ROI: 2.66%
7800 Winnetka Ave Winnetka, CA Charming Winnetka Home with endless potential! Welcome to 7800 Winnetka Ave, offer a sp...	3 beds \| 2 baths \| 2,039 sq.ft.	$760,000	Airbnb cash on cash: 7.65% Traditional cash on cash: 4.26% Airbnb Rental Income: $8334 Traditional Rental Income: $4353 Airbnb ROI: 7.65% Traditional ROI: 4.26%
8328 N Cooper Place Winnetka, CA Welcome to Cooper Place! This newer-built traditional Modern Farmhouse features 4 bedrooms...	4 beds \| 3 baths \| 2,507 sq.ft.	$1,249,000	Airbnb cash on cash: 6.95% Traditional cash on cash: 3.13% Airbnb Rental Income: $12488 Traditional Rental Income: $5779 Airbnb ROI: 6.95% Traditional ROI: 3.13%
20134 Leadwell St #156 Winnetka, CA 20134 Leadwell St #156, Winnetka, CA 91306 \| Condo/Coop	2 beds \| 1 baths \| 855 sq.ft.	$399,999	Airbnb cash on cash: 8% Traditional cash on cash: 2.76% Airbnb Rental Income: $5460 Traditional Rental Income: $2397 Airbnb ROI: 8% Traditional ROI: 2.76%
20109 Archwood St Winnetka, CA 20109 Archwood St, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 4 baths \| 2,720 sq.ft.	$1,249,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.14% Airbnb Rental Income: $14506 Traditional Rental Income: $6940 Airbnb ROI: 8.41% Traditional ROI: 4.14%
20828 Blythe Street Winnetka, CA Price Reduction & EASY to SHOW. Here's the deal of the month! An amazing opportunity to ro...	3 beds \| 2 baths \| 2,258 sq.ft.	$829,950	Airbnb cash on cash: 6.86% Traditional cash on cash: 3.56% Airbnb Rental Income: $8334 Traditional Rental Income: $4204 Airbnb ROI: 6.86% Traditional ROI: 3.56%
7830 Fairchild Avenue Winnetka, CA Stylishly Renovated Pool Home in Winnetka Welcome to 7830 Fairchild Ave â a 4-bedroom...	4 beds \| 2 baths \| 1,704 sq.ft.	$950,000	Airbnb cash on cash: 9.69% Traditional cash on cash: 3.3% Airbnb Rental Income: $12488 Traditional Rental Income: $4561 Airbnb ROI: 9.69% Traditional ROI: 3.3%
19803 Covello Street Winnetka, CA This beautiful home is nestled in one of Winnetkaâs most sought-after neighborhoods and ...	3 beds \| 1 baths \| 1,327 sq.ft.	$824,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 2.9% Airbnb Rental Income: $8334 Traditional Rental Income: $3671 Airbnb ROI: 6.92% Traditional ROI: 2.9%
7463 Mason Ave Winnetka, CA Fantastic Opportunity for you to own your own Private Oasis! You are welcomed by a beauti...	3 beds \| 2 baths \| 1,636 sq.ft.	$899,990	Airbnb cash on cash: 5.94% Traditional cash on cash: 3.52% Airbnb Rental Income: $8334 Traditional Rental Income: $4726 Airbnb ROI: 5.94% Traditional ROI: 3.52%
7306 Jumilla Avenue Winnetka, CA SFR, Standard ADU, and JR ADU! This stunning turn key home with its 2 ADUs is nestled in ...	4 beds \| 3 baths \| 1,970 sq.ft.	$1,350,000	Airbnb cash on cash: 6.31% Traditional cash on cash: 2.3% Airbnb Rental Income: $12488 Traditional Rental Income: $5176 Airbnb ROI: 6.31% Traditional ROI: 2.3%
20110 Cohasset Winnetka, CA Welcome to this stunning, fully remodeled townhouse offering style, comfort, and convenien...	3 beds \| 2 baths \| 1,595 sq.ft.	$645,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 3.58% Airbnb Rental Income: $8334 Traditional Rental Income: $3750 Airbnb ROI: 8.58% Traditional ROI: 3.58%
20224 Sherman Way #26 Winnetka, CA 20224 Sherman Way #26, Winnetka, CA 91306 \| Townhouse	3 beds \| 3 baths \| 1,843 sq.ft.	$599,000	Airbnb cash on cash: 9.3% Traditional cash on cash: 4.55% Airbnb Rental Income: $8334 Traditional Rental Income: $4104 Airbnb ROI: 9.3% Traditional ROI: 4.55%
20251 Vanowen Winnetka, CA Welcome to a fantastic opportunity in the heart of Winnetka! This 3-bedroom, 2-bathroom ho...	3 beds \| 2 baths \| 1,420 sq.ft.	$699,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 3.96% Airbnb Rental Income: $8334 Traditional Rental Income: $3818 Airbnb ROI: 8.47% Traditional ROI: 3.96%
6210 Penfield Ave Winnetka, CA 6210 Penfield Ave, Winnetka, CA 91367 \| Single Family Residential	4 beds \| 3 baths \| 2,682 sq.ft.	$2,295,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 0.46% Airbnb Rental Income: $12488 Traditional Rental Income: $5084 Airbnb ROI: 2.87% Traditional ROI: 0.46%
7230 Kelvin Ave #6 Winnetka, CA Welcome 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% Traditional cash on cash: 3.66% Airbnb Rental Income: $8334 Traditional Rental Income: $3588 Airbnb ROI: 9.42% Traditional ROI: 3.66%
19545 Sherman Way #74 Winnetka, CA Welcome to this stunning, updated condo with pool view in Reseda! This updated 2-bedroom, ...	2 beds \| 1 baths \| 1,319 sq.ft.	$559,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 2.74% Airbnb Rental Income: $5460 Traditional Rental Income: $2917 Airbnb ROI: 5.5% Traditional ROI: 2.74%
20253 Keswick #233 Winnetka, CA Welcome to 20253 Keswick Street, a beautifully maintained 2-bedroom, 2-bath condo located ...	2 beds \| 2 baths \| 880 sq.ft.	$449,999	Airbnb cash on cash: 6.95% Traditional cash on cash: 2.86% Airbnb Rental Income: $5460 Traditional Rental Income: $2637 Airbnb ROI: 6.95% Traditional ROI: 2.86%
20253 Keswick Street #103 Winnetka, CA Don't miss this Upgraded, Open Floor Plan, Two Bedroom, Two Bathroom Condominium with a Hu...	2 beds \| 2 baths \| 880 sq.ft.	$435,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 3.02% Airbnb Rental Income: $5460 Traditional Rental Income: $2637 Airbnb ROI: 7.25% Traditional ROI: 3.02%
7107 Cozycroft Winnetka, CA 7107 Cozycroft, Winnetka, CA 91306 \| Single Family Residential	9 beds \| 8 baths \| 3,624 sq.ft.	$2,200,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.01% Airbnb Rental Income: $14506 Traditional Rental Income: $9823 Airbnb ROI: 4.03% Traditional ROI: 3.01%
20617 Schoenborn Winnetka, CA "This beautifully remodeled home features an open floor plan, a stunning remodel kitchen, ...	3 beds \| 2 baths \| 1,392 sq.ft.	$799,000	Airbnb cash on cash: 7.2% Traditional cash on cash: 3.04% Airbnb Rental Income: $8334 Traditional Rental Income: $3660 Airbnb ROI: 7.2% Traditional ROI: 3.04%

Vacation Rentals in Winnetka

There are 53 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $824,950 and the average price per square foot is $488. The cash on cash return on vacation rentals in Winnetka is 7.00%. The average monthly short term rental income in Winnetka is $8,334.

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

There are 53 Airbnb properties available for sale in Winnetka.

In 2025, the best neighborhood to buy short term rental property is Winnetka.

In December 2025, the average Airbnb occupancy rate in Winnetka is 89%.

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

20155 Keswick Street #209

Winnetka, CA

2 beds | 2 baths | 1,125 sq.ft.

$475,000

Airbnb cash on cash: 6.67%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $5460

Traditional Rental Income: $3209

Airbnb ROI: 6.67%

Traditional ROI: 4.08%

20134 Leadwell St #133

Winnetka, CA

2 beds | 2 baths | 884 sq.ft.

$399,000

Airbnb cash on cash: 8.35%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $5460

Traditional Rental Income: $2849

Airbnb ROI: 8.35%

Traditional ROI: 4.31%

20216 Roscoe Boulevard #19

Winnetka, CA

2 beds | 1 baths | 1,133 sq.ft.

$484,000

Airbnb cash on cash: 6.81%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5460

Traditional Rental Income: $2779

Airbnb ROI: 6.81%

Traditional ROI: 3.32%

20352 Keswick Street

Winnetka, CA

4 beds | 3 baths | 2,178 sq.ft.

$999,000

Airbnb cash on cash: 9.15%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $12488

Traditional Rental Income: $2936

Airbnb ROI: 9.15%

Traditional ROI: 1.31%

19947 Cantara Street

Winnetka, CA

4 beds | 3 baths | 1,924 sq.ft.

$1,015,000

Airbnb cash on cash: 8.94%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $12488

Traditional Rental Income: $4865

Airbnb ROI: 8.94%

Traditional ROI: 3.28%

20737 Roscoe Boulevard #301

Winnetka, CA

3 beds | 3 baths | 1,641 sq.ft.

$658,780

Airbnb cash on cash: 8.18%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $8334

Traditional Rental Income: $4230

Airbnb ROI: 8.18%

Traditional ROI: 4.07%

8231 Mason Avenue #E

Winnetka, CA

2 beds | 2 baths | 1,202 sq.ft.

$549,000

Airbnb cash on cash: 5.37%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $5460

Traditional Rental Income: $2993

Airbnb ROI: 5.37%

Traditional ROI: 2.71%

20254 Stagg Street

Winnetka, CA

4 beds | 3 baths | 2,288 sq.ft.

$948,500

Airbnb cash on cash: 9.71%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $12488

Traditional Rental Income: $3433

Airbnb ROI: 9.71%