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 Welcome home to this light and bright unit with 2B/2B. Quiet luxury building in great area...	2 beds \| 2 baths \| 880 sq.ft.	$434,500	Airbnb cash on cash: 7.19% Traditional cash on cash: 2.14% Airbnb Rental Income: $5460 Traditional Rental Income: $2305 Airbnb ROI: 7.19% Traditional ROI: 2.14%
7020 Oakdale Ave Winnetka, CA One of the most versatile homes in Winnetka remodeled, income-producing, and designed for ...	4 beds \| 2 baths \| 1,290 sq.ft.	$1,000,000	Airbnb cash on cash: 9.13% Traditional cash on cash: 2.61% Airbnb Rental Income: $12488 Traditional Rental Income: $4152 Airbnb ROI: 9.13% Traditional ROI: 2.61%
20234 Cantara St #136 Winnetka, CA Welcome to this charming studio that offers a warm, inviting ambiance from the moment you ...	N/A beds \| 1 baths \| 444 sq.ft.	$299,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 1.84% Airbnb Rental Income: $3301 Traditional Rental Income: $1631 Airbnb ROI: 5.14% Traditional ROI: 1.84%
19833 Bassett St Winnetka, CA Immaculate remodeled Winnetka home located in a quiet family neighborhood has 4 bedrooms a...	4 beds \| 2 baths \| 1,742 sq.ft.	$1,099,000	Airbnb cash on cash: 8.15% Traditional cash on cash: 3.02% Airbnb Rental Income: $12488 Traditional Rental Income: $4976 Airbnb ROI: 8.15% Traditional ROI: 3.02%
20134 Leadwell St #332 Winnetka, CA Welcome to this move-in ready top-floor unit located in the heart of Winnetka. Inside, the...	2 beds \| 2 baths \| 884 sq.ft.	$399,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.76% Airbnb Rental Income: $5460 Traditional Rental Income: $3191 Airbnb ROI: 7.89% Traditional ROI: 4.76%
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%
20027 Community St #55 Winnetka, CA Located in the desirable Woodlands in Winnetka, this beautifully remodeled 1,587 sq ft tow...	3 beds \| 3 baths \| 1,587 sq.ft.	$645,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 3.76% Airbnb Rental Income: $8334 Traditional Rental Income: $3815 Airbnb ROI: 8.65% Traditional ROI: 3.76%
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%
8620 Lubao Ave Winnetka, CA This exceptional income property offers the potential to generate approximately $10,900 (!...	7 beds \| 7 baths \| 3,280 sq.ft.	$1,795,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 0.97% Airbnb Rental Income: $14506 Traditional Rental Income: $3780 Airbnb ROI: 5.89% Traditional ROI: 0.97%
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.	$999,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 0.81% Airbnb Rental Income: $12488 Traditional Rental Income: $2480 Airbnb ROI: 9.14% Traditional ROI: 0.81%
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.	$999,900	Airbnb cash on cash: 9.77% Traditional cash on cash: 1.93% Airbnb Rental Income: $12488 Traditional Rental Income: $2923 Airbnb ROI: 9.77% Traditional ROI: 1.93%
20851 Community St #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.	$650,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 2.8% Airbnb Rental Income: $8334 Traditional Rental Income: $3377 Airbnb ROI: 8.37% Traditional ROI: 2.8%
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%
20235 Keswick Street #212 Winnetka, CA Welcome to this beautifully updated condo located at 20235 Keswick Street, Unit 212 in Win...	2 beds \| 2 baths \| 1,021 sq.ft.	$535,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.25% Airbnb Rental Income: $5460 Traditional Rental Income: $3150 Airbnb ROI: 5.67% Traditional ROI: 3.25%
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%
19844 Hemmingway St Winnetka, CA POOL, SINGLE LEVEL, 4-BED Stop scrolling â this is the one! Welcome home to 19844 He...	4 beds \| 2 baths \| 1,602 sq.ft.	$949,000	Airbnb cash on cash: 9.71% Traditional cash on cash: 2.4% Airbnb Rental Income: $12488 Traditional Rental Income: $3767 Airbnb ROI: 9.71% Traditional ROI: 2.4%
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%
7640 Oso Ave #217 Winnetka, CA 7640 Oso Ave #217, Los Angeles, CA 91306 \| Condo/Coop	1 beds \| 1 baths \| 648 sq.ft.	$285,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 3.78% Airbnb Rental Income: $3229 Traditional Rental Income: $2012 Airbnb ROI: 5.6% Traditional ROI: 3.78%
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.	$835,000	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.95% Airbnb Rental Income: $8334 Traditional Rental Income: $4636 Airbnb ROI: 6.61% Traditional ROI: 3.95%
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%
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%
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%
20656 Acre St Winnetka, CA Incredible opportunity to own a newly remodeled single-family pool home in the highly desi...	3 beds \| 2 baths \| 1,392 sq.ft.	$935,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 2.34% Airbnb Rental Income: $8334 Traditional Rental Income: $3659 Airbnb ROI: 5.9% Traditional ROI: 2.34%
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.	$438,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 3.38% Airbnb Rental Income: $5460 Traditional Rental Income: $2697 Airbnb ROI: 7.44% Traditional ROI: 3.38%
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 \| 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.	$1,229,777	Airbnb cash on cash: 8.57% Traditional cash on cash: 2.23% Airbnb Rental Income: $14506 Traditional Rental Income: $4646 Airbnb ROI: 8.57% Traditional ROI: 2.23%
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%
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%
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.	$1,229,777	Airbnb cash on cash: 4.39% Traditional cash on cash: 1.78% Airbnb Rental Income: $8334 Traditional Rental Income: $3774 Airbnb ROI: 4.39% Traditional ROI: 1.78%
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.	$289,999	Airbnb cash on cash: 5.97% Traditional cash on cash: 3.98% Airbnb Rental Income: $3229 Traditional Rental Income: $1959 Airbnb ROI: 5.97% Traditional ROI: 3.98%
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%
20327 Saticoy #304 Winnetka, CA Welcome home to this beautifully maintained and thoughtfully laid-out residence that blend...	1 beds \| 1 baths \| 640 sq.ft.	$344,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 2.79% Airbnb Rental Income: $3229 Traditional Rental Income: $1861 Airbnb ROI: 4.77% Traditional ROI: 2.79%
19950 Sherman Way #A #A Winnetka, CA Spectacular 3BD/3.5BA Townhouse corner unit highlighting refined finishes and effortless l...	3 beds \| 4 baths \| 1,860 sq.ft.	$549,000	Airbnb cash on cash: 9.59% Traditional cash on cash: 4.87% Airbnb Rental Income: $8334 Traditional Rental Income: $4338 Airbnb ROI: 9.59% Traditional ROI: 4.87%
20422-20424 Schoenborn Winnetka, CA HUGE PRICE IMPROVEMENT plus **SELLER OFFERING CREDITS up to $20,000 TOWARD BUYER'S CLO...	4 beds \| 3 baths \| 2,392 sq.ft.	$1,129,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 2.64% Airbnb Rental Income: $12488 Traditional Rental Income: $4874 Airbnb ROI: 7.56% Traditional ROI: 2.64%
20010 Eccles St Winnetka, CA Welcome to this beautifully updated home, completely reimagined with quality upgrades thro...	3 beds \| 2 baths \| 1,407 sq.ft.	$834,900	Airbnb cash on cash: 6.66% Traditional cash on cash: 2.22% Airbnb Rental Income: $8334 Traditional Rental Income: $3240 Airbnb ROI: 6.66% Traditional ROI: 2.22%
20155 Keswick #209 Winnetka, CA FHA Approved Townhome!!! Beautiful and renovated large two bedroom townhome features an op...	2 beds \| 2 baths \| 1,125 sq.ft.	$485,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 3.15% Airbnb Rental Income: $5460 Traditional Rental Income: $2861 Airbnb ROI: 6.45% Traditional ROI: 3.15%

Vacation Rentals in Winnetka

There are 65 vacation rental properties available for sale in the city of Winnetka . The median list price of Airbnb properties available for sale in Winnetka is $868,000 and the average price per square foot is $459. The cash on cash return on vacation rentals in Winnetka is 8.00%. 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 65 Airbnb properties available for sale in Winnetka.

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

In March 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

20253 Keswick St #325

Winnetka, CA

2 beds | 2 baths | 880 sq.ft.

$434,500

Airbnb cash on cash: 7.19%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $5460

Traditional Rental Income: $2305

Airbnb ROI: 7.19%

Traditional ROI: 2.14%

7020 Oakdale Ave

Winnetka, CA

4 beds | 2 baths | 1,290 sq.ft.

$1,000,000

Airbnb cash on cash: 9.13%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $12488

Traditional Rental Income: $4152

Airbnb ROI: 9.13%

Traditional ROI: 2.61%

20234 Cantara St #136

Winnetka, CA

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

$299,000

Airbnb cash on cash: 5.14%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $3301

Traditional Rental Income: $1631

Airbnb ROI: 5.14%

Traditional ROI: 1.84%

19833 Bassett St

Winnetka, CA

4 beds | 2 baths | 1,742 sq.ft.

$1,099,000

Airbnb cash on cash: 8.15%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $12488

Traditional Rental Income: $4976

Airbnb ROI: 8.15%

Traditional ROI: 3.02%

20134 Leadwell St #332

Winnetka, CA

2 beds | 2 baths | 884 sq.ft.

$399,000

Airbnb cash on cash: 7.89%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $5460

Traditional Rental Income: $3191

Airbnb ROI: 7.89%

Traditional ROI: 4.76%

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%

20027 Community St #55

Winnetka, CA

3 beds | 3 baths | 1,587 sq.ft.

$645,000

Airbnb cash on cash: 8.65%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $8334

Traditional Rental Income: $3815

Airbnb ROI: 8.65%

Traditional ROI: 3.76%

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%