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
7647 Mason Avenue Winnetka, CA Lush Pool Home with Solar & Fruit Trees in the Heart of Winnetka! Discover comfort, style,...	3 beds \| 2 baths \| 2,073 sq.ft.	$868,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 4.04% Airbnb Rental Income: $8334 Traditional Rental Income: $4775 Airbnb ROI: 6.49% Traditional ROI: 4.04%
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.	$499,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 3.8% Airbnb Rental Income: $5460 Traditional Rental Income: $3209 Airbnb ROI: 6.27% Traditional ROI: 3.8%
8140 Quartz Avenue Winnetka, CA PRICE IMPROVEMENT Welcome to 8140 Quartz Avenueâa beautifully maintained two-story h...	4 beds \| 3 baths \| 2,791 sq.ft.	$1,150,000	Airbnb cash on cash: 7.71% Traditional cash on cash: 4.76% Airbnb Rental Income: $12488 Traditional Rental Income: $7056 Airbnb ROI: 7.71% Traditional ROI: 4.76%
20253 Keswick Street #105 Winnetka, CA Bright one bedroom unit on the first floor. Featuring a nicely renovated kitchen and bathr...	1 beds \| 1 baths \| 630 sq.ft.	$375,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 2.97% Airbnb Rental Income: $3229 Traditional Rental Income: $2266 Airbnb ROI: 3.64% Traditional ROI: 2.97%
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.	$1,049,900	Airbnb cash on cash: 8.61% Traditional cash on cash: 3.13% Airbnb Rental Income: $12488 Traditional Rental Income: $4865 Airbnb ROI: 8.61% Traditional ROI: 3.13%
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.	$660,000	Airbnb cash on cash: 8.16% Traditional cash on cash: 4.06% Airbnb Rental Income: $8334 Traditional Rental Income: $4230 Airbnb ROI: 8.16% Traditional ROI: 4.06%
7936 Laramie Avenue Winnetka, CA NEW NEW NEW Elegant 4-Bed, 3-Bath Pool Home with Solar. Welcome to this beautifully upgrad...	4 beds \| 1 baths \| 2,212 sq.ft.	$970,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 4.19% Airbnb Rental Income: $12488 Traditional Rental Income: $5460 Airbnb ROI: 9.46% Traditional ROI: 4.19%
20028 Strathern Street Winnetka, CA Welcome to 20028 Strathern St.âa truly exceptional residence nestled in the heart of Win...	4 beds \| 2 baths \| 1,924 sq.ft.	$1,079,000	Airbnb cash on cash: 8.54% Traditional cash on cash: 2.16% Airbnb Rental Income: $12488 Traditional Rental Income: $3809 Airbnb ROI: 8.54% Traditional ROI: 2.16%
8513 Corbin Avenue Winnetka, CA Welcome to 8513 Corbin Ave, where comfort meets outdoors adventure in the heart of Winnetk...	3 beds \| 2 baths \| 1,704 sq.ft.	$1,098,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 2.59% Airbnb Rental Income: $8334 Traditional Rental Income: $4534 Airbnb ROI: 4.77% Traditional ROI: 2.59%
20254 Stagg Street Winnetka, CA Newly updated 4 BR 3BA detached home. 1 BR 1BA downstairs for easy living. Master BR with ...	4 beds \| 3 baths \| 2,288 sq.ft.	$998,500	Airbnb cash on cash: 9.14% Traditional cash on cash: 1.84% Airbnb Rental Income: $12488 Traditional Rental Income: $3433 Airbnb ROI: 9.14% Traditional ROI: 1.84%
20253 Keswick St #326 Winnetka, CA A Rare Gem! Step into luxury and exclusivity as you enter this stunning Terramar residence...	1 beds \| 1 baths \| 630 sq.ft.	$370,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 1.2% Airbnb Rental Income: $3229 Traditional Rental Income: $1943 Airbnb ROI: 2.81% Traditional ROI: 1.2%
7801 Kelvin Avenue Winnetka, CA Welcome to this stunning Winnetka corner-lot home sitting on a sprawling almost 11,000 sqf...	4 beds \| 3 baths \| 1,980 sq.ft.	$1,149,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 2.3% Airbnb Rental Income: $12488 Traditional Rental Income: $4423 Airbnb ROI: 7.72% Traditional ROI: 2.3%
20428 Roscoe Boulevard Winnetka, CA Welcome to 20428 Roscoe Blvd, Winnetka, CA. A Thoughtfully Updated Home in the Heart of th...	3 beds \| 2 baths \| 1,380 sq.ft.	$878,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 1.3% Airbnb Rental Income: $8334 Traditional Rental Income: $2592 Airbnb ROI: 6.39% Traditional ROI: 1.3%
20431 Stagg Street Winnetka, CA This light-filled home sits on a spacious corner lot with full block walls for privacy. Th...	3 beds \| 2 baths \| 1,313 sq.ft.	$799,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 3.12% Airbnb Rental Income: $8334 Traditional Rental Income: $3519 Airbnb ROI: 7.47% Traditional ROI: 3.12%
20139 Leadwell Street #5 Winnetka, CA THIS WON'T LAST LONG !!! Welcome to this beautifully maintained townhome-style residenc...	2 beds \| 2 baths \| 1,283 sq.ft.	$499,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 3.1% Airbnb Rental Income: $5460 Traditional Rental Income: $2809 Airbnb ROI: 6.43% Traditional ROI: 3.1%
8401 Fullbright Avenue Winnetka, CA Welcome to your dream home in the heart of Winnetka, where comfort, charm, and modern livi...	3 beds \| 3 baths \| 1,375 sq.ft.	$949,998	Airbnb cash on cash: 5.86% Traditional cash on cash: 3.25% Airbnb Rental Income: $8334 Traditional Rental Income: $4448 Airbnb ROI: 5.86% Traditional ROI: 3.25%
20341 Schoenborn Street Winnetka, CA Fully remodeled from top to bottom, this beautifully designed Winnetka home offers modern ...	3 beds \| 2 baths \| 1,330 sq.ft.	$979,900	Airbnb cash on cash: 5.93% Traditional cash on cash: 2.95% Airbnb Rental Income: $8334 Traditional Rental Income: $4038 Airbnb ROI: 5.93% Traditional ROI: 2.95%
20415 Roscoe Boulevard Winnetka, CA MAJOR PRICE REDUCTION!!! SELLER WANTS IT SOLD!!! Beautiful pool home in the city of Winn...	3 beds \| 2 baths \| 1,321 sq.ft.	$774,900	Airbnb cash on cash: 7.47% Traditional cash on cash: 2.98% Airbnb Rental Income: $8334 Traditional Rental Income: $3514 Airbnb ROI: 7.47% Traditional ROI: 2.98%
20851 Community Street #10 Winnetka, CA Stunning Remodeled Home in Gated Community â Move-In Ready! Step into Style and Comfort ...	3 beds \| 3 baths \| 1,460 sq.ft.	$647,000	Airbnb cash on cash: 8.42% Traditional cash on cash: 2.82% Airbnb Rental Income: $8334 Traditional Rental Income: $3377 Airbnb ROI: 8.42% Traditional ROI: 2.82%
20308 Mobile St Winnetka, CA Amazing opportunity for buyers looking for an income property. Nestled in Winnetka's covet...	5 beds \| 4 baths \| 2,600 sq.ft.	$1,295,000	Airbnb cash on cash: 8.05% Traditional cash on cash: 1.01% Airbnb Rental Income: $14506 Traditional Rental Income: $3427 Airbnb ROI: 8.05% Traditional ROI: 1.01%
7614 Mason Avenue Winnetka, CA This stunning quadruplex offers a diverse living arrangement, with Unit 1 featuring 3 bedr...	7 beds \| 6 baths \| 3,980 sq.ft.	$1,385,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 4.5% Airbnb Rental Income: $14506 Traditional Rental Income: $9018 Airbnb ROI: 6.94% Traditional ROI: 4.5%
8467 Penfield Avenue Winnetka, CA The front of the home is beautifully manicured and features impressive Roman-style pillars...	3 beds \| 3 baths \| 2,276 sq.ft.	$959,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 3.88% Airbnb Rental Income: $8334 Traditional Rental Income: $5118 Airbnb ROI: 5.71% Traditional ROI: 3.88%
20159 Cohasset St #9 Winnetka, CA This 2-bedroom, 1-bathroom single-story corner unit condo is located in the gated Forest G...	2 beds \| 1 baths \| 890 sq.ft.	$414,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 3.22% Airbnb Rental Income: $5460 Traditional Rental Income: $2521 Airbnb ROI: 7.96% Traditional ROI: 3.22%
20146 Cohasset Street #15 Winnetka, CA This remodeled townhome in Winnetka offers ample space with two bedrooms, one and a half b...	2 beds \| 1 baths \| 1,070 sq.ft.	$478,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.68% Airbnb Rental Income: $5460 Traditional Rental Income: $3021 Airbnb ROI: 6.67% Traditional ROI: 3.68%
20134 Leadwell St #217 Winnetka, CA Welcome to your beautifully renovated 2-bedroom, 2-bathroom condo in the highly sought-aft...	2 beds \| 2 baths \| 884 sq.ft.	$399,000	Airbnb cash on cash: 8.02% Traditional cash on cash: 5.73% Airbnb Rental Income: $5460 Traditional Rental Income: $3505 Airbnb ROI: 8.02% Traditional ROI: 5.73%
7826 Winnetka Avenue Winnetka, CA Enjoy the best of San Fernando Valley living in this spacious and updated two-story home o...	3 beds \| 3 baths \| 2,070 sq.ft.	$919,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 2.48% Airbnb Rental Income: $8334 Traditional Rental Income: $3714 Airbnb ROI: 6.03% Traditional ROI: 2.48%
6757 Stephanie Place Winnetka, CA Welcome to this beautifully renovated 3 Bedroom, 2 Bathroom single-family home in the hear...	3 beds \| 2 baths \| 1,246 sq.ft.	$848,800	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.04% Airbnb Rental Income: $8334 Traditional Rental Income: $3881 Airbnb ROI: 6.67% Traditional ROI: 3.04%
20234 Cohasset St #3 Winnetka, CA This beautiful totally remodeled 2-bedroom, 2-bathroom condo offers 1,040 square feet of m...	2 beds \| 2 baths \| 1,040 sq.ft.	$435,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 3.72% Airbnb Rental Income: $5460 Traditional Rental Income: $2825 Airbnb ROI: 7.5% Traditional ROI: 3.72%
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.	$979,900	Airbnb cash on cash: 9.35% Traditional cash on cash: 2.73% Airbnb Rental Income: $12488 Traditional Rental Income: $4184 Airbnb ROI: 9.35% Traditional ROI: 2.73%
20235 Keswick Street #102 Winnetka, CA Motivated Seller!!! Priced Reduced!!! Great Winnetka Location! Don't miss this Keswick Vi...	2 beds \| 2 baths \| 1,021 sq.ft.	$435,000	Airbnb cash on cash: 7.48% Traditional cash on cash: 3.84% Airbnb Rental Income: $5460 Traditional Rental Income: $2877 Airbnb ROI: 7.48% Traditional ROI: 3.84%
20322 Cantara Street Winnetka, CA Welcome to this beautifully updated 3bd/2ba home with a pool in Winnetka. Stunning curb ap...	3 beds \| 2 baths \| 1,241 sq.ft.	$950,000	Airbnb cash on cash: 5.62% Traditional cash on cash: 2.34% Airbnb Rental Income: $8334 Traditional Rental Income: $3858 Airbnb ROI: 5.62% Traditional ROI: 2.34%
20234 Cantara Street #107 Winnetka, CA This remodeled Wonderful Winnetka Condo unit has an open floor plan with 2 family bedrooms...	2 beds \| 2 baths \| 990 sq.ft.	$395,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 4.73% Airbnb Rental Income: $5460 Traditional Rental Income: $2908 Airbnb ROI: 8.65% Traditional ROI: 4.73%
19950 Sherman Way #A Winnetka, CA Reduced price!!Welcome to this beautiful, inviting multi-story townhouse in the heart of W...	3 beds \| 2 baths \| 1,860 sq.ft.	$640,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 4.68% Airbnb Rental Income: $8334 Traditional Rental Income: $4670 Airbnb ROI: 8.17% Traditional ROI: 4.68%
8366 Oakdale Avenue Winnetka, CA Versatile living with room to grow in the heart of Winnetka! This spacious and multi-funct...	3 beds \| 2 baths \| 2,115 sq.ft.	$1,019,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 2.59% Airbnb Rental Income: $8334 Traditional Rental Income: $4211 Airbnb ROI: 5.27% Traditional ROI: 2.59%

Vacation Rentals in Winnetka

There are 80 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $849,500 and the average price per square foot is $520. 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 80 Airbnb properties available for sale in Winnetka.

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

In September 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

7647 Mason Avenue

Winnetka, CA

3 beds | 2 baths | 2,073 sq.ft.

$868,000

Airbnb cash on cash: 6.49%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $8334

Traditional Rental Income: $4775

Airbnb ROI: 6.49%

Traditional ROI: 4.04%

20155 Keswick Street #209

Winnetka, CA

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

$499,000

Airbnb cash on cash: 6.27%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $5460

Traditional Rental Income: $3209

Airbnb ROI: 6.27%

Traditional ROI: 3.8%

8140 Quartz Avenue

Winnetka, CA

4 beds | 3 baths | 2,791 sq.ft.

$1,150,000

Airbnb cash on cash: 7.71%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $12488

Traditional Rental Income: $7056

Airbnb ROI: 7.71%

Traditional ROI: 4.76%

20253 Keswick Street #105

Winnetka, CA

1 beds | 1 baths | 630 sq.ft.

$375,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $3229

Traditional Rental Income: $2266

Airbnb ROI: 3.64%

Traditional ROI: 2.97%

19947 Cantara Street

Winnetka, CA

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

$1,049,900

Airbnb cash on cash: 8.61%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $12488

Traditional Rental Income: $4865

Airbnb ROI: 8.61%

Traditional ROI: 3.13%

20737 Roscoe Boulevard #301

Winnetka, CA

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

$660,000

Airbnb cash on cash: 8.16%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $8334

Traditional Rental Income: $4230

Airbnb ROI: 8.16%

Traditional ROI: 4.06%

7936 Laramie Avenue

Winnetka, CA

4 beds | 1 baths | 2,212 sq.ft.

$970,000

Airbnb cash on cash: 9.46%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $12488

Traditional Rental Income: $5460

Airbnb ROI: 9.46%

Traditional ROI: 4.19%

20028 Strathern Street

Winnetka, CA

4 beds | 2 baths | 1,924 sq.ft.

$1,079,000

Airbnb cash on cash: 8.54%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $12488

Traditional Rental Income: $3809

Airbnb ROI: 8.54%