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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20155 Keswick St #219 Winnetka, CA Welcome to this beautifully remodeled, move-in-ready modern townhouse in the heart of Winn...	2 beds \| 2 baths \| 1,078 sq.ft.	$499,999	Airbnb cash on cash: 6.17% Traditional cash on cash: 3.55% Airbnb Rental Income: $5460 Traditional Rental Income: $3136 Airbnb ROI: 6.17% Traditional ROI: 3.55%
20241 Baltar St Winnetka, CA Set in a quiet double cul-de-sac find this sweet Traditional where the essence of a happy ...	4 beds \| 3 baths \| 2,230 sq.ft.	$1,049,900	Airbnb cash on cash: 8.61% Traditional cash on cash: 3.14% Airbnb Rental Income: $12488 Traditional Rental Income: $4876 Airbnb ROI: 8.61% Traditional ROI: 3.14%
8846 Laramie Ave Winnetka, CA INCREDIBLE 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% Traditional cash on cash: 3.18% Airbnb Rental Income: $12488 Traditional Rental Income: $5370 Airbnb ROI: 7.71% Traditional ROI: 3.18%
20134 Leadwell St #159 Winnetka, CA Donât 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% Traditional cash on cash: 3.11% Airbnb Rental Income: $5460 Traditional Rental Income: $2640 Airbnb ROI: 7.43% Traditional ROI: 3.11%
8446 Penfield Ave Winnetka, CA MASSIVE 22,000 SQ FT FLAT LOT!!! Located just minutes away from Northridge Mall. What sets...	6 beds \| 4 baths \| 2,697 sq.ft.	$2,135,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 0.26% Airbnb Rental Income: $14506 Traditional Rental Income: $2727 Airbnb ROI: 4.89% Traditional ROI: 0.26%
7410 Cozycroft Ave Winnetka, CA This beautifully remodeled home is nestled on a picturesque tree lined street in one of Wi...	4 beds \| 2 baths \| 1,557 sq.ft.	$1,025,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 1.86% Airbnb Rental Income: $12488 Traditional Rental Income: $2923 Airbnb ROI: 9.51% Traditional ROI: 1.86%
20308 Mobile St Winnetka, CA Amazing opportunity to own a newly renovated, immaculate, move in ready home in Winnetka's...	5 beds \| 3 baths \| 2,500 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%
7439 Mason Ave Winnetka, CA Call Jessica Nieto (562) 714-2176 Cash only! Equity Opportunity in the City of Los Angel...	3 beds \| 2 baths \| 1,293 sq.ft.	$898,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 2.81% Airbnb Rental Income: $8334 Traditional Rental Income: $3914 Airbnb ROI: 6.21% Traditional ROI: 2.81%
8467 Penfield Ave Winnetka, CA The 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% Traditional cash on cash: 3.99% Airbnb Rental Income: $8334 Traditional Rental Income: $5118 Airbnb ROI: 5.87% Traditional ROI: 3.99%
8626 Lubao Ave Winnetka, CA A rare, high-performing investment opportunity with projected monthly income of up to $11,...	7 beds \| 7 baths \| 3,000 sq.ft.	$1,795,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 0.5% Airbnb Rental Income: $8334 Traditional Rental Income: $3013 Airbnb ROI: 2.85% Traditional ROI: 0.5%
20134 Leadwell St #263 Winnetka, CA Bring in the New Year with a remodeled 2 Bedroom, 2Bathroom Condo in Winnetka. This unit h...	2 beds \| 2 baths \| 884 sq.ft.	$419,000	Airbnb cash on cash: 7.43% Traditional cash on cash: 3.43% Airbnb Rental Income: $5460 Traditional Rental Income: $2789 Airbnb ROI: 7.43% Traditional ROI: 3.43%
8600 Mason Ave Winnetka, CA This home is currently set up for SOBER LIVING ARRANGEMENTS and the details can be found i...	4 beds \| 3 baths \| 1,958 sq.ft.	$874,950	Airbnb cash on cash: 9.45% Traditional cash on cash: -0.07% Airbnb Rental Income: $12488 Traditional Rental Income: $2460 Airbnb ROI: 9.45% Traditional ROI: -0.07%
20414 Haynes St Winnetka, CA Welcome to this beautifully updated Winnetka home, perfectly suited for the California lif...	4 beds \| 2 baths \| 1,362 sq.ft.	$998,000	Airbnb cash on cash: 9.15% Traditional cash on cash: 2.17% Airbnb Rental Income: $12488 Traditional Rental Income: $3738 Airbnb ROI: 9.15% Traditional ROI: 2.17%
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%
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%
7640 Oso Ave #316 Winnetka, CA This 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% Traditional cash on cash: 4.2% Airbnb Rental Income: $3229 Traditional Rental Income: $2291 Airbnb ROI: 4.91% Traditional ROI: 4.2%
20551 Saticoy St Winnetka, CA WOW!!! Great Opportunity for a large family. Fully remodeled, new roof, new copper plumbi...	3 beds \| 2 baths \| 1,543 sq.ft.	$865,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 3.88% Airbnb Rental Income: $8334 Traditional Rental Income: $4636 Airbnb ROI: 6.52% Traditional ROI: 3.88%
20329 Stagg St Winnetka, CA A 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% Traditional cash on cash: 4.76% Airbnb Rental Income: $14506 Traditional Rental Income: $11168 Airbnb ROI: 5.2% Traditional ROI: 4.76%
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 Ave 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.	$1,300,000	Airbnb cash on cash: 6.62% Traditional cash on cash: 2.45% Airbnb Rental Income: $12488 Traditional Rental Income: $5176 Airbnb ROI: 6.62% Traditional ROI: 2.45%
7812-7812 Fairchild Ave 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: 2.67% Airbnb Rental Income: $8334 Traditional Rental Income: $3905 Airbnb ROI: 5.98% Traditional ROI: 2.67%
20651 Roscoe Blvd #L Winnetka, CA Price Improvement!!! This two-story, three-bedroom 2.5 bath townhouse is a rare find!! W...	3 beds \| 2 baths \| 1,586 sq.ft.	$660,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 2.96% Airbnb Rental Income: $8334 Traditional Rental Income: $3577 Airbnb ROI: 8.12% Traditional ROI: 2.96%
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%
20243 Lanark St Winnetka, CA This stunning 2,932-square-foot Winnetka home features 4 bedrooms, 3 baths, and 3 versatil...	4 beds \| 3 baths \| 2,932 sq.ft.	$1,079,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 2.87% Airbnb Rental Income: $12488 Traditional Rental Income: $4734 Airbnb ROI: 8.33% Traditional ROI: 2.87%
20258 Cohasset St #4 Winnetka, CA Beautiful bright 2 level townhouse with back patio. 2 bedroom and 1 1/2 bath. Central Heat...	2 beds \| 1 baths \| 1,050 sq.ft.	$456,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 3.18% Airbnb Rental Income: $5460 Traditional Rental Income: $2697 Airbnb ROI: 7.07% Traditional ROI: 3.18%
7107 Cozycroft Winnetka, CA 7107 Cozycroft, Winnetka, CA 91306 \| Single Family Residential	9 beds \| 8 baths \| 3,624 sq.ft.	$1,998,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 3.49% Airbnb Rental Income: $14506 Traditional Rental Income: $9823 Airbnb ROI: 4.61% Traditional ROI: 3.49%
20134 Leadwell St #374 Winnetka, CA Seller is very motivated. Lots of amenities . style Modern construction, the condo is situ...	2 beds \| 2 baths \| 888 sq.ft.	$395,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 3.48% Airbnb Rental Income: $5460 Traditional Rental Income: $2641 Airbnb ROI: 8.12% Traditional ROI: 3.48%
7414 Quartz Winnetka, CA This 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% Traditional cash on cash: 3.35% Airbnb Rental Income: $8334 Traditional Rental Income: $4609 Airbnb ROI: 5.78% Traditional ROI: 3.35%
20737 Roscoe #704 Winnetka, CA Windsor Park 2 + 2 1/2 Townhome with Great Floorplan. Laminate Floors, Recessed Lights, Gr...	2 beds \| 2 baths \| 1,580 sq.ft.	$620,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 2.92% Airbnb Rental Income: $5460 Traditional Rental Income: $3410 Airbnb ROI: 4.56% Traditional ROI: 2.92%
20528 Hamlin St Winnetka, CA 20528-& 20526 Hamlin St, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 3 baths \| 1,788 sq.ft.	$1,249,777	Airbnb cash on cash: 8.41% Traditional cash on cash: 2.16% Airbnb Rental Income: $14506 Traditional Rental Income: $4646 Airbnb ROI: 8.41% Traditional ROI: 2.16%
20247 Lanark Winnetka, CA âCharming 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% Traditional cash on cash: 2.04% Airbnb Rental Income: $14506 Traditional Rental Income: $6058 Airbnb ROI: 5.35% Traditional ROI: 2.04%
8021 NW Mcnulty Ave Winnetka, CA 8021 NW Mcnulty Ave, Los Angeles, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,592 sq.ft.	$1,450,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 1.08% Airbnb Rental Income: $8334 Traditional Rental Income: $3916 Airbnb ROI: 3.19% Traditional ROI: 1.08%
20234 Cantara Winnetka, CA This is a one bedroom STUDIO which has a partition for privacy. It is still considered a S...	1 beds \| 1 baths \| 444 sq.ft.	$279,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 2.23% Airbnb Rental Income: $3229 Traditional Rental Income: $1670 Airbnb ROI: 5.4% Traditional ROI: 2.23%
20819 W Seasons Ln Winnetka, CA NEW 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% Traditional cash on cash: 1.73% Airbnb Rental Income: $12488 Traditional Rental Income: $4753 Airbnb ROI: 5.95% Traditional ROI: 1.73%
8636-8636 Delco Winnetka, CA Welcome to this spacious single-story retreat, perfectly tucked away at the end of a cul-d...	3 beds \| 2 baths \| 2,024 sq.ft.	$929,900	Airbnb cash on cash: 5.94% Traditional cash on cash: 2.91% Airbnb Rental Income: $8334 Traditional Rental Income: $4134 Airbnb ROI: 5.94% Traditional ROI: 2.91%
20456 W Strathern St Winnetka, CA 20456 W Strathern St, Los Angeles, CA 91306 \| Single Family Residential	8 beds \| 5 baths \| 3,022 sq.ft.	$1,589,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 2.84% Airbnb Rental Income: $14506 Traditional Rental Income: $6868 Airbnb ROI: 6.24% Traditional ROI: 2.84%
20528 Hamlin Street Winnetka, CA Outstanding Modern Masterpiecce \| Welcome To This 2 Homes In One Lot Beautifully Designed ...	5 beds \| 3 baths \| 1,788 sq.ft.	$1,249,777	Airbnb cash on cash: 8.73% Traditional cash on cash: 1.74% Airbnb Rental Income: $14506 Traditional Rental Income: $3774 Airbnb ROI: 8.73% Traditional ROI: 1.74%
20327 Saticoy St #102 Winnetka, CA In the heart of Winnetka, this well-maintained 1-bedroom condo offers a secured entrance a...	1 beds \| 1 baths \| 640 sq.ft.	$299,999	Airbnb cash on cash: 5.72% Traditional cash on cash: 3.79% Airbnb Rental Income: $3229 Traditional Rental Income: $1959 Airbnb ROI: 5.72% Traditional ROI: 3.79%
19832 Welby Way Winnetka, CA Welcome to this serene Winnetka retreat, where comfort, space, and relaxation come togethe...	3 beds \| 2 baths \| 1,663 sq.ft.	$890,000	Airbnb cash on cash: 6.28% Traditional cash on cash: 3.56% Airbnb Rental Income: $8334 Traditional Rental Income: $4501 Airbnb ROI: 6.28% Traditional ROI: 3.56%
8353 Lurline Ave Winnetka, CA 8353 Lurline Ave, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,482 sq.ft.	$849,950	Airbnb cash on cash: 6.66% Traditional cash on cash: 2.33% Airbnb Rental Income: $8334 Traditional Rental Income: $3325 Airbnb ROI: 6.66% Traditional ROI: 2.33%

Vacation Rentals in Winnetka

There are 62 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $872,425 and the average price per square foot is $505. 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 62 Airbnb properties available for sale in Winnetka.

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

In February 2026, 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 St #219

Winnetka, CA

2 beds | 2 baths | 1,078 sq.ft.

$499,999

Airbnb cash on cash: 6.17%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $5460

Traditional Rental Income: $3136

Airbnb ROI: 6.17%

Traditional ROI: 3.55%

20241 Baltar St

Winnetka, CA

4 beds | 3 baths | 2,230 sq.ft.

$1,049,900

Airbnb cash on cash: 8.61%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $12488

Traditional Rental Income: $4876

Airbnb ROI: 8.61%

Traditional ROI: 3.14%

8846 Laramie Ave

Winnetka, CA

4 beds | 3 baths | 2,399 sq.ft.

$1,150,000

Airbnb cash on cash: 7.71%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $12488

Traditional Rental Income: $5370

Airbnb ROI: 7.71%

Traditional ROI: 3.18%

20134 Leadwell St #159

Winnetka, CA

2 beds | 2 baths | 884 sq.ft.

$425,000

Airbnb cash on cash: 7.43%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $5460

Traditional Rental Income: $2640

Airbnb ROI: 7.43%

Traditional ROI: 3.11%

8446 Penfield Ave

Winnetka, CA

6 beds | 4 baths | 2,697 sq.ft.

$2,135,000

Airbnb cash on cash: 4.89%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $14506

Traditional Rental Income: $2727

Airbnb ROI: 4.89%

Traditional ROI: 0.26%

7410 Cozycroft Ave

Winnetka, CA

4 beds | 2 baths | 1,557 sq.ft.

$1,025,000

Airbnb cash on cash: 9.51%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $12488

Traditional Rental Income: $2923

Airbnb ROI: 9.51%

Traditional ROI: 1.86%

20308 Mobile St

Winnetka, CA

5 beds | 3 baths | 2,500 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%

7439 Mason Ave

Winnetka, CA

3 beds | 2 baths | 1,293 sq.ft.

$898,000

Airbnb cash on cash: 6.21%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $8334

Traditional Rental Income: $3914

Airbnb ROI: 6.21%