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
20134 Leadwell St #133 Winnetka, CA 20134 Leadwell St #133, Winnetka, CA 91306 \| Condo/Coop	2 beds \| 2 baths \| 884 sq.ft.	$380,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 4.57% Airbnb Rental Income: $5460 Traditional Rental Income: $2849 Airbnb ROI: 8.81% Traditional ROI: 4.57%
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.	$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 Bright and charming 1-bedroom, 1-bath condo with 630 sq. ft., high ceilings, fireplace, an...	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%
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%
20308 Mobile St Winnetka, CA Amazing opportunity to own a newly renovated, immaculate, move in ready home in Winnetka's...	5 beds \| 4 baths \| 2,500 sq.ft.	$1,325,000	Airbnb cash on cash: 7.83% Traditional cash on cash: 0.95% Airbnb Rental Income: $14506 Traditional Rental Income: $3427 Airbnb ROI: 7.83% Traditional ROI: 0.95%
19714 Lull St 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%
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.	$889,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.22% Airbnb Rental Income: $8334 Traditional Rental Income: $4211 Airbnb ROI: 6.29% Traditional ROI: 3.22%
8527 Casaba Avenue Winnetka, CA Freshly painted andMove-In-Ready 3 Bed \| 2 Bath Pool Home on Oversized Lot in Winnetka, CA...	3 beds \| 2 baths \| 1,300 sq.ft.	$895,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 2.45% Airbnb Rental Income: $8334 Traditional Rental Income: $3601 Airbnb ROI: 6.24% Traditional ROI: 2.45%
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%
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 Avenue Winnetka, CA Main House: 7306 Jumilla= 3 Bedrooms, 2.5 Bathrooms, 1385 Sq.Ft. Jr. ADU: 7308 J...	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%
19709 Strathern Street Winnetka, CA Beautiful Winnetka Pool Home on a Corner Lot. Welcome home to this charming single-story p...	3 beds \| 2 baths \| 1,316 sq.ft.	$859,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 2.67% Airbnb Rental Income: $8334 Traditional Rental Income: $3630 Airbnb ROI: 6.57% Traditional ROI: 2.67%
7812 Fairchild Avenue 7812 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%
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%
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%
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%
20258 Cohasset St unit: 4 #4 Winnetka, CA Beautiful bright 2 level townhouse with remodeled kitchen and a back patio. 2 bedroom and ...	2 beds \| 2 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.	$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 modern kitchen, a...	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%
20134 Leadwell Street #374 Winnetka, CA Seller is motivated. Modern construction, the condo is situated on the top 3rd level. ...	2 beds \| 2 baths \| 888 sq.ft.	$405,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 3.35% Airbnb Rental Income: $5460 Traditional Rental Income: $2641 Airbnb ROI: 7.88% Traditional ROI: 3.35%
20231 Elkwood Winnetka, CA Step into modern luxury with this fully remodeled 2-story home offering 4 bedrooms, 4 bath...	5 beds \| 4 baths \| 3,229 sq.ft.	$1,249,999	Airbnb cash on cash: 8.4% Traditional cash on cash: 4.07% Airbnb Rental Income: $14506 Traditional Rental Income: $6861 Airbnb ROI: 8.4% Traditional ROI: 4.07%
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 For a private Showing Contact Regina at 1(818) 772-1562	2 beds \| 3 baths \| 1,580 sq.ft.	$620,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 2.96% Airbnb Rental Income: $5460 Traditional Rental Income: $3410 Airbnb ROI: 4.6% Traditional ROI: 2.96%
20528 Hamlin St Winnetka, CA 20528-& 20526 Hamlin St, Winnetka, CA 91306 \| Single Family Residential	5 beds \| 3 baths \| 1,788 sq.ft.	$1,259,777	Airbnb cash on cash: 8.33% Traditional cash on cash: 2.13% Airbnb Rental Income: $14506 Traditional Rental Income: $4646 Airbnb ROI: 8.33% Traditional ROI: 2.13%
7138 Lurline Winnetka, CA Welcome to 7138 Lurline, a beautifully remodeled home in the heart of Winnetka, CA. This c...	3 beds \| 2 baths \| 1,212 sq.ft.	$799,000	Airbnb cash on cash: 7.2% Traditional cash on cash: 2.88% Airbnb Rental Income: $8334 Traditional Rental Income: $3545 Airbnb ROI: 7.2% Traditional ROI: 2.88%
20224 Sherman #14 Winnetka, CA Welcome to this spacious and well-maintained 4-bedroom, 3-bath townhome located in a desir...	3 beds \| 3 baths \| 1,843 sq.ft.	$639,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 4.06% Airbnb Rental Income: $8334 Traditional Rental Income: $4109 Airbnb ROI: 8.5% Traditional ROI: 4.06%
20258 Runnymede St Winnetka, CA Charming Newly Renovated Tri-Level Corner-Lot Home in Winnetka! Welcome to 20258 Runnymed...	3 beds \| 2 baths \| 2,095 sq.ft.	$769,950	Airbnb cash on cash: 7.53% Traditional cash on cash: 4.04% Airbnb Rental Income: $8334 Traditional Rental Income: $4248 Airbnb ROI: 7.53% Traditional ROI: 4.04%
20442 Runnymede Winnetka, CA Welcome to your next chapter in this warm, inviting Winnetka retreat! This charming two-st...	4 beds \| 3 baths \| 2,010 sq.ft.	$929,000	Airbnb cash on cash: 9.95% Traditional cash on cash: 3.2% Airbnb Rental Income: $12488 Traditional Rental Income: $4375 Airbnb ROI: 9.95% Traditional ROI: 3.2%
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%

Vacation Rentals in Winnetka

There are 45 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $889,000 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 45 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

20134 Leadwell St #133

Winnetka, CA

2 beds | 2 baths | 884 sq.ft.

$380,000

Airbnb cash on cash: 8.81%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $5460

Traditional Rental Income: $2849

Airbnb ROI: 8.81%

Traditional ROI: 4.57%

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%

Traditional ROI: 2.03%

20253 Keswick St #326

Winnetka, CA

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%

20428 Roscoe Boulevard

Winnetka, CA

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%

20308 Mobile St

Winnetka, CA

5 beds | 4 baths | 2,500 sq.ft.

$1,325,000

Airbnb cash on cash: 7.83%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $14506

Traditional Rental Income: $3427

Airbnb ROI: 7.83%

Traditional ROI: 0.95%

19714 Lull St

Winnetka, CA

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%

8366 Oakdale Avenue

Winnetka, CA

3 beds | 2 baths | 2,115 sq.ft.

$889,000

Airbnb cash on cash: 6.29%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $8334

Traditional Rental Income: $4211

Airbnb ROI: 6.29%

Traditional ROI: 3.22%

8527 Casaba Avenue

Winnetka, CA

3 beds | 2 baths | 1,300 sq.ft.

$895,000

Airbnb cash on cash: 6.24%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $8334

Traditional Rental Income: $3601

Airbnb ROI: 6.24%