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
20253 Keswick St #325 Winnetka, CA Motivated Seller. Welcome home to this light and bright unit with 2B/2B. Quiet luxury buil...	2 beds \| 2 baths \| 880 sq.ft.	$399,500	Airbnb cash on cash: 4.17% Traditional cash on cash: 2.47% Airbnb Rental Income: $3753 Traditional Rental Income: $2305 Airbnb ROI: 4.17% Traditional ROI: 2.47%
20146 Cohasset St #5 Winnetka, CA	3 beds \| 2 baths \| 1,340 sq.ft.	$459,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 5.94% Airbnb Rental Income: $5274 Traditional Rental Income: $3806 Airbnb ROI: 6.87% Traditional ROI: 5.94%
20234 Cantara St #136 Winnetka, CA PRICE IMPROVEMENT Turnkey vs fixer opportunity Welcome to this charming studio that ...	N/A beds \| 1 baths \| 444 sq.ft.	$249,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 2.54% Airbnb Rental Income: $2969 Traditional Rental Income: $1631 Airbnb ROI: 5.32% Traditional ROI: 2.54%
20606 Skouras Dr Winnetka, CA This inviting single-story home in a quiet Winnetka neighborhood offers 4 bedrooms and 2 b...	4 beds \| 2 baths \| 1,362 sq.ft.	$846,600	Airbnb cash on cash: 5.76% Traditional cash on cash: 3.66% Airbnb Rental Income: $7353 Traditional Rental Income: $4285 Airbnb ROI: 5.76% Traditional ROI: 3.66%
8340 Penfield Ave #35 Winnetka, CA Gated Private Townhouse community, only 37 units. This townhome is at the back of the comp...	3 beds \| 2 baths \| 1,282 sq.ft.	$640,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 2% Airbnb Rental Income: $5274 Traditional Rental Income: $2851 Airbnb ROI: 4.27% Traditional ROI: 2%
7708 Oakdale Ave Winnetka, CA	4 beds \| 3 baths \| 2,294 sq.ft.	$950,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 3.63% Airbnb Rental Income: $7353 Traditional Rental Income: $4851 Airbnb ROI: 4.86% Traditional ROI: 3.63%
20126 Runnymede St #22 Winnetka, CA Located in a well-established Winnetka townhome community, this stunning corner unit offer...	3 beds \| 3 baths \| 1,615 sq.ft.	$629,999	Airbnb cash on cash: 4.34% Traditional cash on cash: 4.25% Airbnb Rental Income: $5274 Traditional Rental Income: $4149 Airbnb ROI: 4.34% Traditional ROI: 4.25%
20134 Leadwell St #334 Winnetka, CA Back On Market. SOLD with Multiple Offers last time! Buyer did not perform. This beautiful...	3 beds \| 2 baths \| 1,113 sq.ft.	$499,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 3.19% Airbnb Rental Income: $5274 Traditional Rental Income: $3064 Airbnb ROI: 5.64% Traditional ROI: 3.19%
20428 Roscoe Blvd Winnetka, CA Welcome to 20428 Roscoe Blvd. A Thoughtfully Updated Home in the Heart of the Valley Step ...	3 beds \| 2 baths \| 1,380 sq.ft.	$838,800	Airbnb cash on cash: 3.51% Traditional cash on cash: 1.44% Airbnb Rental Income: $5274 Traditional Rental Income: $2592 Airbnb ROI: 3.51% Traditional ROI: 1.44%
7445 Oakdale Ave Winnetka, CA Exceptional Investment Opportunity in Prime Winnetka â Generating $11,050/month in Renta...	6 beds \| 4 baths \| 2,570 sq.ft.	$1,750,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.82% Airbnb Rental Income: $5274 Traditional Rental Income: $3313 Airbnb ROI: 1.45% Traditional ROI: 0.82%
7032 Penfield Ave Winnetka, CA Exceptional opportunity in the heart of Winneka! This versatile property features a beauti...	5 beds \| N/A baths \| N/A	$1,169,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 0.54% Airbnb Rental Income: $5274 Traditional Rental Income: $2732 Airbnb ROI: 1.9% Traditional ROI: 0.54%
7916 Mason Ave Winnetka, CA Welcome to this beautifully updated 4-bedroom, 2-bathroom home offering bright, open livin...	4 beds \| 1 baths \| 1,923 sq.ft.	$939,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 0.97% Airbnb Rental Income: $7353 Traditional Rental Income: $2480 Airbnb ROI: 4.93% Traditional ROI: 0.97%
20253 Keswick St #323 Winnetka, CA 20253 Keswick St #323, Los Angeles, CA 91306 \| Condo/Coop	2 beds \| 2 baths \| 880 sq.ft.	$465,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.24% Airbnb Rental Income: $3753 Traditional Rental Income: $2459 Airbnb ROI: 3.34% Traditional ROI: 2.24%
6952 Cozycroft Ave Winnetka, CA Fixer-upper Opportunity in a Beautiful Neighborhood. Looking for your next project in a pr...	4 beds \| 3 baths \| 2,251 sq.ft.	$1,395,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 0.83% Airbnb Rental Income: $7353 Traditional Rental Income: $3449 Airbnb ROI: 2.75% Traditional ROI: 0.83%
20737 Roscoe Blvd #203 Winnetka, CA	2 beds \| 3 baths \| 1,580 sq.ft.	$559,990	Airbnb cash on cash: 2.52% Traditional cash on cash: 2.38% Airbnb Rental Income: $3753 Traditional Rental Income: $2866 Airbnb ROI: 2.52% Traditional ROI: 2.38%
20531 Covello St Winnetka, CA Location, Location, Location!!!! This property includes a three bedroom two bath house, ...	4 beds \| 3 baths \| 1,693 sq.ft.	$999,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 2.05% Airbnb Rental Income: $7353 Traditional Rental Income: $4006 Airbnb ROI: 4.13% Traditional ROI: 2.05%
19918 Kittridge St Winnetka, CA 3 bedroom/1 bath residence offers tremendous potential for those with a vision to transfor...	8 beds \| 6 baths \| 3,395 sq.ft.	$1,675,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 0.2% Airbnb Rental Income: $8679 Traditional Rental Income: $3228 Airbnb ROI: 2.58% Traditional ROI: 0.2%
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: 2.65% Traditional cash on cash: 1.73% Airbnb Rental Income: $7353 Traditional Rental Income: $4753 Airbnb ROI: 2.65% Traditional ROI: 1.73%
8353 Lurline Ave Winnetka, CA 8353 Lurline Ave, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,482 sq.ft.	$869,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 2.24% Airbnb Rental Income: $5274 Traditional Rental Income: $3325 Airbnb ROI: 3.33% Traditional ROI: 2.24%
20458 Malden Winnetka, CA Great Home needs updating Great location	4 beds \| 2 baths \| 1,572 sq.ft.	$800,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 3.28% Airbnb Rental Income: $7353 Traditional Rental Income: $3843 Airbnb ROI: 6.09% Traditional ROI: 3.28%
7101 Oso Ave #16 Winnetka, CA Motivated Seller: Welcome to 7101 Oso Ave #16, a charming free standing detached home tuck...	3 beds \| 3 baths \| 1,926 sq.ft.	$750,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 3.28% Airbnb Rental Income: $5274 Traditional Rental Income: $4184 Airbnb ROI: 3.31% Traditional ROI: 3.28%
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: 3.77% Traditional cash on cash: 3.42% Airbnb Rental Income: $5274 Traditional Rental Income: $3946 Airbnb ROI: 3.77% Traditional ROI: 3.42%
7211 Cozycroft #32 Winnetka, CA HOT HOT HOT...DO NOT MISS THIS ONE! SELLER WILL COVER BUYERS' FIRST 6 MONTHS OF HOA PAYM...	2 beds \| 2 baths \| 1,033 sq.ft.	$399,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.4% Airbnb Rental Income: $3753 Traditional Rental Income: $2896 Airbnb ROI: 3.51% Traditional ROI: 3.4%
7640 Oso #318 Winnetka, CA	2 beds \| 2 baths \| 899 sq.ft.	$420,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 4.01% Airbnb Rental Income: $3753 Traditional Rental Income: $2859 Airbnb ROI: 4.21% Traditional ROI: 4.01%
20253 Keswick St #318 Winnetka, CA Great Third Floor 2 + 2 Condominium with Open Tree-top View and no one above. Move in read...	2 beds \| 2 baths \| 880 sq.ft.	$418,950	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.09% Airbnb Rental Income: $3753 Traditional Rental Income: $2623 Airbnb ROI: 3.9% Traditional ROI: 3.09%
20234 Cantara St #314 Winnetka, CA Welcome to this inviting 2-bedroom, 2-bathroom top-floor condo Unit 314 at 20234 Cantara S...	2 beds \| 2 baths \| 925 sq.ft.	$375,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 4.1% Airbnb Rental Income: $3753 Traditional Rental Income: $2681 Airbnb ROI: 4.83% Traditional ROI: 4.1%
20134 Leadwell #126 Winnetka, CA Fully updated first-floor condo with a rare oversized private patio in a quiet gated Winne...	2 beds \| 1 baths \| 786 sq.ft.	$410,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.8% Airbnb Rental Income: $3753 Traditional Rental Income: $2503 Airbnb ROI: 3.93% Traditional ROI: 2.8%
20214 Cohasset St #16 Winnetka, CA	2 beds \| 1 baths \| 880 sq.ft.	$379,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.32% Airbnb Rental Income: $3753 Traditional Rental Income: $2396 Airbnb ROI: 4.85% Traditional ROI: 3.32%
20230 Keswick #3 Winnetka, CA $70/ HOA and $87/ Solar Panels, and home qualifies for Credits towards Rate Buy Down and o...	3 beds \| 2 baths \| 1,463 sq.ft.	$699,999	Airbnb cash on cash: 4.43% Traditional cash on cash: 3.23% Airbnb Rental Income: $5274 Traditional Rental Income: $3426 Airbnb ROI: 4.43% Traditional ROI: 3.23%
6547 Kelvin Winnetka, CA Located in one of Winnetka's most sought-after neighborhoods, this upgraded property offer...	4 beds \| 3 baths \| 1,740 sq.ft.	$1,200,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.06% Airbnb Rental Income: $7353 Traditional Rental Income: $5164 Airbnb ROI: 2.76% Traditional ROI: 2.06%
20146 Cohasset #11 Winnetka, CA	3 beds \| 1 baths \| 1,340 sq.ft.	$495,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 3.34% Airbnb Rental Income: $5274 Traditional Rental Income: $2952 Airbnb ROI: 6.05% 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.	$655,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.91% Airbnb Rental Income: $5274 Traditional Rental Income: $4096 Airbnb ROI: 4.09% Traditional ROI: 3.91%
20234 Cohasset #7 Winnetka, CA Why continue paying rent when you can start building equity and ownership in a place to ca...	2 beds \| 2 baths \| 1,040 sq.ft.	$399,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 4.44% Airbnb Rental Income: $3753 Traditional Rental Income: $2909 Airbnb ROI: 4.52% Traditional ROI: 4.44%
7211 Cozycroft #16 Winnetka, CA	2 beds \| 2 baths \| 1,033 sq.ft.	$400,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 4.07% Airbnb Rental Income: $3753 Traditional Rental Income: $2902 Airbnb ROI: 4.17% Traditional ROI: 4.07%
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: 5.3% Traditional cash on cash: 2.31% Airbnb Rental Income: $2969 Traditional Rental Income: $1581 Airbnb ROI: 5.3% Traditional ROI: 2.31%
7058 Fullbright Winnetka, CA This beautifully maintained three bed, two bath Winnetka residence blends modern upgrades ...	3 beds \| 2 baths \| 1,300 sq.ft.	$909,995	Airbnb cash on cash: 3.1% Traditional cash on cash: 2.31% Airbnb Rental Income: $5274 Traditional Rental Income: $3536 Airbnb ROI: 3.1% Traditional ROI: 2.31%
20247 Parthenia Winnetka, CA 20247 Parthenia, Winnetka, CA 91306 \| Single Family Residential	6 beds \| 3 baths \| 2,180 sq.ft.	$1,150,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 2.57% Airbnb Rental Income: $8679 Traditional Rental Income: $4921 Airbnb ROI: 4.48% Traditional ROI: 2.57%
20608 Valerio Winnetka, CA	3 beds \| 2 baths \| 1,293 sq.ft.	$874,999	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.59% Airbnb Rental Income: $5274 Traditional Rental Income: $3677 Airbnb ROI: 3.24% Traditional ROI: 2.59%
20158 Gresham St Winnetka, CA 20158 Gresham St, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,650 sq.ft.	$875,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.91% Airbnb Rental Income: $5274 Traditional Rental Income: $3898 Airbnb ROI: 3.29% Traditional ROI: 2.91%
6923 Comanche Ave Winnetka, CA Welcome to this inviting single story home in Winnetka, ideally located near Warner Center...	3 beds \| 2 baths \| 1,267 sq.ft.	$825,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.95% Airbnb Rental Income: $5274 Traditional Rental Income: $3713 Airbnb ROI: 3.6% Traditional ROI: 2.95%

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 $799,000 and the average price per square foot is $449. The cash on cash return on vacation rentals in Winnetka is 4.00%. The average monthly short term rental income in Winnetka is $5,274.

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 July 2026, the average Airbnb occupancy rate in Winnetka is 43%.

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

20253 Keswick St #325

Winnetka, CA

2 beds | 2 baths | 880 sq.ft.

$399,500

Airbnb cash on cash: 4.17%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $3753

Traditional Rental Income: $2305

Airbnb ROI: 4.17%

Traditional ROI: 2.47%

20146 Cohasset St #5

Winnetka, CA

3 beds | 2 baths | 1,340 sq.ft.

$459,000

Airbnb cash on cash: 6.87%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $5274

Traditional Rental Income: $3806

Airbnb ROI: 6.87%

Traditional ROI: 5.94%

20234 Cantara St #136

Winnetka, CA

N/A beds | 1 baths | 444 sq.ft.

$249,000

Airbnb cash on cash: 5.32%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $2969

Traditional Rental Income: $1631

Airbnb ROI: 5.32%

Traditional ROI: 2.54%

20606 Skouras Dr

Winnetka, CA

4 beds | 2 baths | 1,362 sq.ft.

$846,600

Airbnb cash on cash: 5.76%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $7353

Traditional Rental Income: $4285

Airbnb ROI: 5.76%

Traditional ROI: 3.66%

8340 Penfield Ave #35

Winnetka, CA

3 beds | 2 baths | 1,282 sq.ft.

$640,000

Airbnb cash on cash: 4.27%

Traditional cash on cash: 2%

Airbnb Rental Income: $5274

Traditional Rental Income: $2851

Airbnb ROI: 4.27%

Traditional ROI: 2%

7708 Oakdale Ave

Winnetka, CA

4 beds | 3 baths | 2,294 sq.ft.

$950,000

Airbnb cash on cash: 4.86%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $7353

Traditional Rental Income: $4851

Airbnb ROI: 4.86%

Traditional ROI: 3.63%

20126 Runnymede St #22

Winnetka, CA

3 beds | 3 baths | 1,615 sq.ft.

$629,999

Airbnb cash on cash: 4.34%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $5274

Traditional Rental Income: $4149

Airbnb ROI: 4.34%

Traditional ROI: 4.25%

20134 Leadwell St #334

Winnetka, CA

3 beds | 2 baths | 1,113 sq.ft.

$499,000

Airbnb cash on cash: 5.64%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $5274

Traditional Rental Income: $3064

Airbnb ROI: 5.64%