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
8140 Quartz Avenue Winnetka, CA Welcome to 8140 Quartz Avenueâa beautifully maintained two-story home offering over 2,70...	4 beds \| 3 baths \| 2,791 sq.ft.	$1,100,000	Airbnb cash on cash: 8.14% Traditional cash on cash: 5.05% Airbnb Rental Income: $12488 Traditional Rental Income: $7056 Airbnb ROI: 8.14% Traditional ROI: 5.05%
19947 Cantara Street Winnetka, CA Price Improvement .!!!! Welcome to your private resort style oasis. This exquisitely renov...	4 beds \| 3 baths \| 1,924 sq.ft.	$1,015,000	Airbnb cash on cash: 8.94% Traditional cash on cash: 3.28% Airbnb Rental Income: $12488 Traditional Rental Income: $4865 Airbnb ROI: 8.94% Traditional ROI: 3.28%
20737 Roscoe Boulevard #301 Winnetka, CA Split Level Windsor Park Townhouse! This 3 BR/3 BA End Unit Offers w/Open Concept Floorpla...	3 beds \| 3 baths \| 1,641 sq.ft.	$660,000	Airbnb cash on cash: 8.16% Traditional cash on cash: 4.06% Airbnb Rental Income: $8334 Traditional Rental Income: $4230 Airbnb ROI: 8.16% Traditional ROI: 4.06%
20028 Strathern Street Winnetka, CA Welcome to 20028 Strathern St.âa truly exceptional residence nestled in the heart of Win...	4 beds \| 3 baths \| 1,924 sq.ft.	$1,039,000	Airbnb cash on cash: 8.91% Traditional cash on cash: 2.28% Airbnb Rental Income: $12488 Traditional Rental Income: $3809 Airbnb ROI: 8.91% Traditional ROI: 2.28%
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.	$355,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 1.99% Airbnb Rental Income: $3229 Traditional Rental Income: $1943 Airbnb ROI: 3.67% Traditional ROI: 1.99%
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%
20341 Schoenborn Street Winnetka, CA MAJOR PRICE IMPROVEMENT! Fully remodeled from top to bottom, this beautifully designed W...	3 beds \| 2 baths \| 1,330 sq.ft.	$899,900	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.29% Airbnb Rental Income: $8334 Traditional Rental Income: $4038 Airbnb ROI: 6.54% Traditional ROI: 3.29%
7614 Mason Avenue Winnetka, CA This stunning quadruplex offers a diverse living arrangement, with Unit 1 featuring 3 bedr...	7 beds \| 6 baths \| 3,980 sq.ft.	$1,350,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.65% Airbnb Rental Income: $8334 Traditional Rental Income: $9018 Airbnb ROI: 3.04% Traditional ROI: 4.65%
20134 Leadwell St #217 Winnetka, CA Welcome to your beautifully renovated 2-bedroom, 2-bathroom condo in the highly sought-aft...	2 beds \| 2 baths \| 884 sq.ft.	$399,000	Airbnb cash on cash: 8.02% Traditional cash on cash: 5.73% Airbnb Rental Income: $5460 Traditional Rental Income: $3505 Airbnb ROI: 8.02% Traditional ROI: 5.73%
6757 Stephanie Place Winnetka, CA Welcome to this beautifully renovated 3 Bedroom, 2 Bathroom single-family home in the hear...	3 beds \| 2 baths \| 1,246 sq.ft.	$800,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 3.33% Airbnb Rental Income: $8334 Traditional Rental Income: $3881 Airbnb ROI: 7.18% Traditional ROI: 3.33%
20235 Keswick Street #102 Winnetka, CA Back on the market! Don't let this one pass you by. Motivated Seller!!! Priced Reduced!!...	2 beds \| 2 baths \| 1,021 sq.ft.	$427,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 3.82% Airbnb Rental Income: $5460 Traditional Rental Income: $2877 Airbnb ROI: 7.53% Traditional ROI: 3.82%
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.	$945,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 2.93% Airbnb Rental Income: $8334 Traditional Rental Income: $4211 Airbnb ROI: 5.82% Traditional ROI: 2.93%
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%
19931 LORNE Winnetka, CA Winnetka great location, this beautiful one story home located peaceful nice street. with...	3 beds \| 2 baths \| 1,627 sq.ft.	$799,000	Airbnb cash on cash: 7.2% Traditional cash on cash: 3.85% Airbnb Rental Income: $8334 Traditional Rental Income: $4263 Airbnb ROI: 7.2% Traditional ROI: 3.85%
20122 Cohasset Street Winnetka, CA LOTS OF UPDATES!! Beautiful 2bed 2.5bath Winnetka townhome in gorgeous, gated Franciscan P...	2 beds \| 3 baths \| 1,337 sq.ft.	$550,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 3.44% Airbnb Rental Income: $5460 Traditional Rental Income: $3205 Airbnb ROI: 5.69% Traditional ROI: 3.44%
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%
19803 Covello Street Winnetka, CA 3 Bedrooms, 2 Baths, Pool , $824,900, This beautiful home is nestled in one of Winnetkaâ...	3 beds \| 2 baths \| 1,327 sq.ft.	$824,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 2.9% Airbnb Rental Income: $8334 Traditional Rental Income: $3671 Airbnb ROI: 6.92% Traditional ROI: 2.9%
19928 Chase Street #17 Winnetka, CA Beautifully Updated 2-Bedroom Townhome in Prime LocationStep into this light-filled, highl...	2 beds \| 3 baths \| 1,270 sq.ft.	$594,999	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.32% Airbnb Rental Income: $5460 Traditional Rental Income: $3534 Airbnb ROI: 4.81% Traditional ROI: 3.32%
19952 Vanowen St Winnetka, CA CUTE HOME UNDER $699K W LARGE YARD! ; MOVE IN CONDITION! ...but yes, it needs some paint ...	3 beds \| 1 baths \| 1,072 sq.ft.	$679,000	Airbnb cash on cash: 8.77% Traditional cash on cash: 3.67% Airbnb Rental Income: $8334 Traditional Rental Income: $3527 Airbnb ROI: 8.77% Traditional ROI: 3.67%
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%
20134 Leadwell St #306 Winnetka, CA Bright & Updated 2-Bedroom Winnetka Condominium This top-floor unit offers comfort, style...	2 beds \| 2 baths \| 884 sq.ft.	$375,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 3.76% Airbnb Rental Income: $5460 Traditional Rental Income: $2644 Airbnb ROI: 8.64% Traditional ROI: 3.76%
20110 Cohasset Winnetka, CA Welcome to this stunning, fully remodeled townhouse offering style, comfort, and convenien...	3 beds \| 3 baths \| 1,595 sq.ft.	$645,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 3.58% Airbnb Rental Income: $8334 Traditional Rental Income: $3750 Airbnb ROI: 8.58% Traditional ROI: 3.58%
20323 Haynes Street Winnetka, CA Welcome to this charming 1-story home in the heart of Winnetka. Featuring 3 bedrooms and 2...	3 beds \| 2 baths \| 1,841 sq.ft.	$899,900	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.05% Airbnb Rental Income: $8334 Traditional Rental Income: $4117 Airbnb ROI: 6.2% Traditional ROI: 3.05%
8101 Sunnybrae Avenue Winnetka, CA Step into this beautifully remodeled single-story home featuring 3 spacious bedrooms and v...	3 beds \| 2 baths \| 1,572 sq.ft.	$895,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 2.82% Airbnb Rental Income: $8334 Traditional Rental Income: $3908 Airbnb ROI: 6.24% Traditional ROI: 2.82%
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.	$889,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 2.52% Airbnb Rental Income: $8334 Traditional Rental Income: $3630 Airbnb ROI: 6.29% Traditional ROI: 2.52%
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%
20251 Vanowen Winnetka, CA Welcome to a fantastic opportunity in the heart of Winnetka! This 3-bedroom, 2-bathroom ho...	3 beds \| 2 baths \| 1,420 sq.ft.	$699,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 3.96% Airbnb Rental Income: $8334 Traditional Rental Income: $3818 Airbnb ROI: 8.47% Traditional ROI: 3.96%
20150 Hemmingway Street Winnetka, CA Nestled on a quiet, residential cul-de-sac in Winnetka, this beautifully maintained 5-bedr...	5 beds \| 4 baths \| 3,276 sq.ft.	$1,195,000	Airbnb cash on cash: 8.87% Traditional cash on cash: 3.87% Airbnb Rental Income: $14506 Traditional Rental Income: $6344 Airbnb ROI: 8.87% Traditional ROI: 3.87%
19931 Lanark Street Winnetka, CA Welcoming family home in Winnetka! This 3 bedroom, 3 bathroom home offers a large living ...	3 beds \| 3 baths \| 2,108 sq.ft.	$985,000	Airbnb cash on cash: 5.51% Traditional cash on cash: 2.74% Airbnb Rental Income: $8334 Traditional Rental Income: $4212 Airbnb ROI: 5.51% Traditional ROI: 2.74%
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.	$459,999	Airbnb cash on cash: 6.77% Traditional cash on cash: 2.76% Airbnb Rental Income: $5460 Traditional Rental Income: $2637 Airbnb ROI: 6.77% Traditional ROI: 2.76%
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.	$455,000	Airbnb cash on cash: 6.86% Traditional cash on cash: 2.81% Airbnb Rental Income: $5460 Traditional Rental Income: $2637 Airbnb ROI: 6.86% Traditional ROI: 2.81%
20258 Cohasset St #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.	$468,888	Airbnb cash on cash: 6.84% Traditional cash on cash: 3.04% Airbnb Rental Income: $5460 Traditional Rental Income: $2697 Airbnb ROI: 6.84% Traditional ROI: 3.04%
20307 Mobile St Winnetka, CA 20307 Mobile St, Winnetka, CA 91306 \| Single Family Residential	3 beds \| 2 baths \| 1,529 sq.ft.	$899,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 2.87% Airbnb Rental Income: $8334 Traditional Rental Income: $3960 Airbnb ROI: 6.21% Traditional ROI: 2.87%

Real Estate investment in Winnetka, CA

There are 43 properties for sale in the city of Winnetka . The median list price in Winnetka is $873,000 and the average price per square foot is $499. In October 2025, the average monthly cash on cash return in Winnetka is 3.00%. The average monthly rental income in Winnetka is $4,000.

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

There are 43 investment properties available for sale in Winnetka.

In 2025, 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

8140 Quartz Avenue

Winnetka, CA

4 beds | 3 baths | 2,791 sq.ft.

$1,100,000

Airbnb cash on cash: 8.14%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $12488

Traditional Rental Income: $7056

Airbnb ROI: 8.14%

Traditional ROI: 5.05%

19947 Cantara Street

Winnetka, CA

4 beds | 3 baths | 1,924 sq.ft.

$1,015,000

Airbnb cash on cash: 8.94%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $12488

Traditional Rental Income: $4865

Airbnb ROI: 8.94%

Traditional ROI: 3.28%

20737 Roscoe Boulevard #301

Winnetka, CA

3 beds | 3 baths | 1,641 sq.ft.

$660,000

Airbnb cash on cash: 8.16%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $8334

Traditional Rental Income: $4230

Airbnb ROI: 8.16%

Traditional ROI: 4.06%

20028 Strathern Street

Winnetka, CA

4 beds | 3 baths | 1,924 sq.ft.

$1,039,000

Airbnb cash on cash: 8.91%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $12488

Traditional Rental Income: $3809

Airbnb ROI: 8.91%

Traditional ROI: 2.28%

20253 Keswick St #326

Winnetka, CA

1 beds | 1 baths | 630 sq.ft.

$355,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $3229

Traditional Rental Income: $1943

Airbnb ROI: 3.67%

Traditional ROI: 1.99%

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%

20341 Schoenborn Street

Winnetka, CA

3 beds | 2 baths | 1,330 sq.ft.

$899,900

Airbnb cash on cash: 6.54%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $8334

Traditional Rental Income: $4038

Airbnb ROI: 6.54%

Traditional ROI: 3.29%

7614 Mason Avenue

Winnetka, CA

7 beds | 6 baths | 3,980 sq.ft.

$1,350,000

Airbnb cash on cash: 3.04%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $8334

Traditional Rental Income: $9018

Airbnb ROI: 3.04%