Real Estate Investment Properties for Sale in Winnetka, CA

Looking for investment property in Winnetka, CA with high ROI ?

Explore a variety of short-term homes & houses in Winnetka, CA. Invest wisely with VRBO & Winnetka, CA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Winnetka, CA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20253 Keswick Street #109 Winnetka, CA Located in a quiet residential neighborhood, close to shopping and entertainment, this rar...	1 beds \| 1 baths \| 630 sq.ft.	$389,921	Airbnb cash on cash: 3.19% Traditional cash on cash: 2.03% Airbnb Rental Income: $3229 Traditional Rental Income: $2076 Airbnb ROI: 3.19% Traditional ROI: 2.03%
20609 Hartland Street Winnetka, CA 12 Units!! 20609-17 Hartland St., Winnetka in two six unit buildings next door to each oth...	8 beds \| N/A baths \| 4,064 sq.ft.	$2,760,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.65% Airbnb Rental Income: $null Traditional Rental Income: $4931 Airbnb ROI: N/A Traditional ROI: 0.65%
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%
19916 Cantara Street Winnetka, CA *PRICE REDUCED*With a fresh, modern look, 19916 Cantera is back on the market! From ne...	4 beds \| 3 baths \| 2,350 sq.ft.	$1,025,000	Airbnb cash on cash: 8.86% Traditional cash on cash: 3.56% Airbnb Rental Income: $12488 Traditional Rental Income: $5166 Airbnb ROI: 8.86% Traditional ROI: 3.56%
20327 Saticoy Street #203 Winnetka, CA Back on the Market and an Opportunity for you to own this Beautifully Maintained Secured E...	1 beds \| 1 baths \| 640 sq.ft.	$339,999	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.3% Airbnb Rental Income: $3229 Traditional Rental Income: $2008 Airbnb ROI: 4.85% Traditional ROI: 3.3%
20344 Mobile Street Winnetka, CA Welcome to this stunning, fully reimagined Mid-Century Modern home in Winnetka, perfectly ...	4 beds \| 3 baths \| 1,870 sq.ft.	$1,099,900	Airbnb cash on cash: 8.14% Traditional cash on cash: 2.18% Airbnb Rental Income: $12488 Traditional Rental Income: $4119 Airbnb ROI: 8.14% Traditional ROI: 2.18%
8513 Fullbright Avenue Winnetka, CA Welcome to 8513 Fullbright Ave, paired with a fully permitted, private ADU at 8515 Fullbri...	4 beds \| 2 baths \| 2,288 sq.ft.	$1,249,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 2.72% Airbnb Rental Income: $12488 Traditional Rental Income: $5294 Airbnb ROI: 6.96% Traditional ROI: 2.72%
20356 Gresham Street Winnetka, CA If youâre looking for your dream home, here it isâyouâre in the right place! Welcome...	4 beds \| 2 baths \| 1,850 sq.ft.	$1,200,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 2.32% Airbnb Rental Income: $12488 Traditional Rental Income: $4642 Airbnb ROI: 7.32% Traditional ROI: 2.32%
7614 Mason Avenue Winnetka, CA Outstanding residential income opportunity in the heart of Winnetka! Welcome to 7614 Mason...	7 beds \| 6 baths \| 3,980 sq.ft.	$1,398,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.45% Airbnb Rental Income: $null Traditional Rental Income: $9018 Airbnb ROI: N/A Traditional ROI: 4.45%
20754 Hartland Winnetka, CA 3 separate apartment buildings side by side. 20754 Hartland is a six unit apartment buildi...	6 beds \| N/A baths \| 3,862 sq.ft.	$3,995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.67% Airbnb Rental Income: $null Traditional Rental Income: $6334 Airbnb ROI: N/A Traditional ROI: 0.67%
8467 Penfield Avenue Winnetka, CA REDUCTION-REDUCTION-REDUCTION !! Take furniture too ! UNIQUE GEM !! this beautiful home...	3 beds \| 3 baths \| 2,276 sq.ft.	$989,000	Airbnb cash on cash: 5.49% Traditional cash on cash: 3.71% Airbnb Rental Income: $8334 Traditional Rental Income: $5118 Airbnb ROI: 5.49% Traditional ROI: 3.71%
20760 Hartland Street Winnetka, CA Four Buildings, 50 Units, Multi-residential Portfolio. Three of the buildings are in Winne...	10 beds \| N/A baths \| 4,878 sq.ft.	$11,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.43% Airbnb Rental Income: $null Traditional Rental Income: $6339 Airbnb ROI: N/A Traditional ROI: -0.43%
8856 Fullbright Avenue Winnetka, CA Property taken off market due to uncooperative tenants. Unlawful detainer action in proce...	4 beds \| 1 baths \| 1,687 sq.ft.	$950,000	Airbnb cash on cash: 9.81% Traditional cash on cash: 2.2% Airbnb Rental Income: $12488 Traditional Rental Income: $3487 Airbnb ROI: 9.81% Traditional ROI: 2.2%
20224 Sherman Way #28 Winnetka, CA Back on the market at no fault to seller. Located in the heart of Winnetka, this well-main...	3 beds \| 3 baths \| 1,843 sq.ft.	$649,000	Airbnb cash on cash: 8.53% Traditional cash on cash: 4.74% Airbnb Rental Income: $8334 Traditional Rental Income: $4464 Airbnb ROI: 8.53% Traditional ROI: 4.74%
20807 Vose Street Winnetka, CA Fantastic single level remodeled home with sparkling pool features 3 bedrooms, and 2.5 bat...	3 beds \| 2 baths \| 1,380 sq.ft.	$975,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 2.44% Airbnb Rental Income: $8334 Traditional Rental Income: $3901 Airbnb ROI: 5.59% Traditional ROI: 2.44%
20155 Keswick Street #214 Winnetka, CA If you're looking for a great deal in town look no further! Located in the serene city of ...	2 beds \| 3 baths \| 1,114 sq.ft.	$514,750	Airbnb cash on cash: 6.07% Traditional cash on cash: 4.17% Airbnb Rental Income: $5460 Traditional Rental Income: $3446 Airbnb ROI: 6.07% Traditional ROI: 4.17%
20134 Leadwell Street #314 Winnetka, CA Fabulously Renovated Condo in Amenity-Rich Community. Exceptionally Remodeled and Stylish ...	2 beds \| 2 baths \| 884 sq.ft.	$399,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 4.2% Airbnb Rental Income: $5460 Traditional Rental Income: $2870 Airbnb ROI: 8.18% Traditional ROI: 4.2%
7211 Cozycroft Avenue #34 Winnetka, CA Welcome home to your oasis in the middle of a city-living lifestyle, in one of Winnetka's ...	2 beds \| 2 baths \| 1,033 sq.ft.	$465,000	Airbnb cash on cash: 6.65% Traditional cash on cash: 3.87% Airbnb Rental Income: $5460 Traditional Rental Income: $3153 Airbnb ROI: 6.65% Traditional ROI: 3.87%
20134 Leadwell Street #263 Winnetka, CA	2 beds \| 2 baths \| 884 sq.ft.	$395,000	Airbnb cash on cash: 8.28% Traditional cash on cash: 4.04% Airbnb Rental Income: $5460 Traditional Rental Income: $2789 Airbnb ROI: 8.28% Traditional ROI: 4.04%
20347 Haynes Street Winnetka, CA Move-in ready, beautifully remodeled private single-story home in the Winnetka community. ...	4 beds \| 2 baths \| 2,131 sq.ft.	$999,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 3.4% Airbnb Rental Income: $12488 Traditional Rental Income: $4881 Airbnb ROI: 9.14% Traditional ROI: 3.4%
8351 Quartz Avenue Winnetka, CA Charming Winnetka Home with Fruitful Oasis Rare Opportunity: This classic Winnetka home...	3 beds \| 2 baths \| 2,047 sq.ft.	$1,035,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 3.2% Airbnb Rental Income: $8334 Traditional Rental Income: $4867 Airbnb ROI: 5.16% Traditional ROI: 3.2%
20801 Keswick Street Winnetka, CA Discover your dream home! Located in a quiet and highly sought-after Winnetka neighborhoo...	3 beds \| 2 baths \| 1,691 sq.ft.	$800,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 3.9% Airbnb Rental Income: $8334 Traditional Rental Income: $4214 Airbnb ROI: 7.31% Traditional ROI: 3.9%
7038 Quakertown Avenue Winnetka, CA This Wonderful Winnetka home located in a quiet family neighborhood has 4 bedrooms & 1.75 ...	4 beds \| 2 baths \| 2,371 sq.ft.	$1,149,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 3.29% Airbnb Rental Income: $12488 Traditional Rental Income: $5483 Airbnb ROI: 7.72% Traditional ROI: 3.29%
20605 Desert Ash Lane Winnetka, CA Discover your dream home brought to you by the prestigious builder Meritage homes. This wo...	3 beds \| 3 baths \| 1,894 sq.ft.	$799,900	Airbnb cash on cash: 6.98% Traditional cash on cash: 4.73% Airbnb Rental Income: $8334 Traditional Rental Income: $5078 Airbnb ROI: 6.98% Traditional ROI: 4.73%
7101 Hatillo Avenue Winnetka, CA Welcome to this Charming and unique two-story home in Winnetka, a perfect blend of space a...	4 beds \| 4 baths \| 2,219 sq.ft.	$1,125,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 2.83% Airbnb Rental Income: $12488 Traditional Rental Income: $4892 Airbnb ROI: 7.92% Traditional ROI: 2.83%
20134 Leadwell Street #303 Winnetka, CA Price improvement! Incredible opportunity to own a beautiful 2 bedroom 2 bath condo that h...	2 beds \| 2 baths \| 884 sq.ft.	$399,900	Airbnb cash on cash: 8.16% Traditional cash on cash: 4.09% Airbnb Rental Income: $5460 Traditional Rental Income: $2834 Airbnb ROI: 8.16% Traditional ROI: 4.09%
6852 Hatillo Avenue #A Winnetka, CA Discover tranquility in this beautifully designed multi-level townhome in Winnetka! With 3...	3 beds \| 3 baths \| 1,528 sq.ft.	$615,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 1.29% Airbnb Rental Income: $8334 Traditional Rental Income: $2286 Airbnb ROI: 9.08% Traditional ROI: 1.29%
20055 Dampa Lane Winnetka, CA Back on Market at no fault of the seller! Buyer did not perform - Welcome to 20055 Dampa L...	3 beds \| 2 baths \| 1,822 sq.ft.	$819,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 1.57% Airbnb Rental Income: $8334 Traditional Rental Income: $2860 Airbnb ROI: 6.68% Traditional ROI: 1.57%
7745 Stagg Lane Winnetka, CA Enviably set in a gated Winnetka community, this newer-build residence offers modern livin...	4 beds \| 4 baths \| 3,047 sq.ft.	$1,339,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 2.78% Airbnb Rental Income: $12488 Traditional Rental Income: $5872 Airbnb ROI: 6.27% Traditional ROI: 2.78%
6738 Laramie Avenue Winnetka, CA Reduced to $785,000- take another look at this cute house with big backyard- Convenient Lo...	3 beds \| 2 baths \| 1,284 sq.ft.	$785,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 3.36% Airbnb Rental Income: $8334 Traditional Rental Income: $3838 Airbnb ROI: 7.35% Traditional ROI: 3.36%
20140 Cohasset Street Winnetka, CA !!Fixer Alert!! 2 bed 2 bath townhome in lovely gated community in the heart of Winnetka i...	2 beds \| 2 baths \| 1,283 sq.ft.	$429,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 5.9% Airbnb Rental Income: $5460 Traditional Rental Income: $3612 Airbnb ROI: 7.76% Traditional ROI: 5.9%
19735 Blythe Street Winnetka, CA HUGE $200,000 PRICE REDUCTION!! DON'T MISS OUT!! Beautiful 4 bed 3 bath 2,473 sq ft 2 stor...	4 beds \| 3 baths \| 2,473 sq.ft.	$999,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 3.72% Airbnb Rental Income: $12488 Traditional Rental Income: $5184 Airbnb ROI: 9.14% Traditional ROI: 3.72%
20327 Saticoy Street #205 Winnetka, CA This condo in the City of Winnetka sounds like a great opportunity for a new owner. Secure...	2 beds \| 2 baths \| 850 sq.ft.	$425,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 4.67% Airbnb Rental Income: $5460 Traditional Rental Income: $2949 Airbnb ROI: 8.21% Traditional ROI: 4.67%
20011 Eccles Street Winnetka, CA Welcome to your charming home in Winnetka! Nestled on a tranquil cul-de-sac, this delightf...	3 beds \| 2 baths \| 1,407 sq.ft.	$775,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 2.77% Airbnb Rental Income: $8334 Traditional Rental Income: $3358 Airbnb ROI: 7.47% Traditional ROI: 2.77%

Real Estate investment in Winnetka, CA

There are 57 properties for sale in the city of Winnetka . The median list price in Winnetka is $875,000 and the average price per square foot is $490. In November 2024, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $4,176.

Winnetka, CA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 57 investment properties available for sale in Winnetka.

In 2024, the best neighborhood to buy investment property is Winnetka.

The ROI for Short-Term is higher than the Long-Term in Winnetka with average rental income of $8,334.

Your search for investment property begins and ends here

Investment Property for Sale in Winnetka, CA

20253 Keswick Street #109

Winnetka, CA

1 beds | 1 baths | 630 sq.ft.

$389,921

Airbnb cash on cash: 3.19%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $3229

Traditional Rental Income: $2076

Airbnb ROI: 3.19%

Traditional ROI: 2.03%

20609 Hartland Street

Winnetka, CA

8 beds | N/A baths | 4,064 sq.ft.

$2,760,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.65%

Airbnb Rental Income: $null

Traditional Rental Income: $4931

Airbnb ROI: N/A

Traditional ROI: 0.65%

8513 Corbin Avenue

Winnetka, CA

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%

19916 Cantara Street

Winnetka, CA

4 beds | 3 baths | 2,350 sq.ft.

$1,025,000

Airbnb cash on cash: 8.86%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $12488

Traditional Rental Income: $5166

Airbnb ROI: 8.86%

Traditional ROI: 3.56%

20327 Saticoy Street #203

Winnetka, CA

1 beds | 1 baths | 640 sq.ft.

$339,999

Airbnb cash on cash: 4.85%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $3229

Traditional Rental Income: $2008

Airbnb ROI: 4.85%

Traditional ROI: 3.3%

20344 Mobile Street

Winnetka, CA

4 beds | 3 baths | 1,870 sq.ft.

$1,099,900

Airbnb cash on cash: 8.14%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $12488

Traditional Rental Income: $4119

Airbnb ROI: 8.14%

Traditional ROI: 2.18%

8513 Fullbright Avenue

Winnetka, CA

4 beds | 2 baths | 2,288 sq.ft.

$1,249,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $12488

Traditional Rental Income: $5294

Airbnb ROI: 6.96%

Traditional ROI: 2.72%

20356 Gresham Street

Winnetka, CA

4 beds | 2 baths | 1,850 sq.ft.

$1,200,000

Airbnb cash on cash: 7.32%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $12488

Traditional Rental Income: $4642

Airbnb ROI: 7.32%