Real Estate Investment Properties for Sale in Winchester, CA

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

Explore a variety of short-term homes & houses in Winchester, CA. Invest wisely with VRBO & Winchester, 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 Winchester, CA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
33043 Wesley Street Winchester, CA Tucked into a peaceful neighborhood with true small-town charm, this hard-to-find 4-unit p...	9 beds \| 6 baths \| 2,272 sq.ft.	$1,075,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.56% Airbnb Rental Income: $null Traditional Rental Income: $1714 Airbnb ROI: N/A Traditional ROI: 0.56%
32900 Bootlegg Winchester, CA Set on 5 fully usable acres with no HOA, this 5-bedroom, 3-bathroom ranch-style home offer...	5 beds \| 4 baths \| 2,536 sq.ft.	$999,999	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.35% Airbnb Rental Income: $1983 Traditional Rental Income: $5554 Airbnb ROI: -0.04% Traditional ROI: 4.35%
Investment Properties for Sale in Other Cities of California
16632 Calle Jermaine Pacific Palisades , CA Perched in the exclusive Summit Club of the Palisades Highlands, this immaculate Mediterra...	4 beds \| 3 baths \| 2,781 sq.ft.	$2,895,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 0.91% Airbnb Rental Income: $14891 Traditional Rental Income: $7719 Airbnb ROI: 2.58% Traditional ROI: 0.91%
23026 Mobile Street West Hills , CA Stunning Smart Home with Designer Finishes and Luxury Features. Welcome to this exception...	5 beds \| 5 baths \| 2,515 sq.ft.	$1,480,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.48% Airbnb Rental Income: $3431 Traditional Rental Income: $7284 Airbnb ROI: 0.12% Traditional ROI: 3.48%
5417 Allott Ave SHERMAN OAKS , CA This Is The One Of A Kind Super Sharp Gated 5 Bedroom Dream Home That You Have Been Waitin...	5 beds \| 4 baths \| 3,048 sq.ft.	$1,799,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.4% Airbnb Rental Income: $4174 Traditional Rental Income: $8704 Airbnb ROI: 0.16% Traditional ROI: 3.4%
15020 Encanto Dr SHERMAN OAKS , CA Spacious 5-Bedroom Retreat in Prime Sherman Oaks. South of the Boulevard. Tucked away in o...	5 beds \| 5 baths \| 4,222 sq.ft.	$2,444,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 0.2% Airbnb Rental Income: $4174 Traditional Rental Income: $4537 Airbnb ROI: -0.35% Traditional ROI: 0.2%
16857 San Fernando Mission Boulevard #24 GRANADA HILLS , CA Welcome to Granada Groveâthe only townhome community within a half-mile of this prime Gr...	2 beds \| 3 baths \| 1,228 sq.ft.	$525,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 3.58% Airbnb Rental Income: $4232 Traditional Rental Income: $3214 Airbnb ROI: 3.84% Traditional ROI: 3.58%
10215 Variel Avenue 11 Chatsworth , CA Cozy, Charming, and Convenient Living in Chatsworth. This spacious and renovated three ...	3 beds \| 4 baths \| 1,604 sq.ft.	$615,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 6.44% Airbnb Rental Income: $3231 Traditional Rental Income: $4797 Airbnb ROI: 2.44% Traditional ROI: 6.44%
4900 Queen Victoria Rd Woodland Hills , CA This mid-century modern gem offers the perfect blend of style, comfort, and privacy. A str...	5 beds \| 4 baths \| 3,806 sq.ft.	$2,199,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.3% Airbnb Rental Income: $2820 Traditional Rental Income: $6355 Airbnb ROI: -0.75% Traditional ROI: 1.3%
19633 Wells Dr Tarzana , CA Elegant East Coast inspired gated residence in Tarzana, built in 2014, situated on an expa...	5 beds \| 5 baths \| 4,518 sq.ft.	$3,157,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.86% Airbnb Rental Income: $3529 Traditional Rental Income: $7743 Airbnb ROI: -0.85% Traditional ROI: 0.86%
22460 Venido Rd Woodland Hills , CA Tucked away in the highly desirable Woodland Hills South, within the private and picturesq...	3 beds \| 2 baths \| 1,509 sq.ft.	$1,195,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.81% Airbnb Rental Income: $3027 Traditional Rental Income: $4054 Airbnb ROI: 0.26% Traditional ROI: 1.81%
22239 Erwin Street Woodland Hills , CA Welcome home! Check out this beautifully upgraded condo located in one of Woodland Hills' ...	2 beds \| 2 baths \| 1,416 sq.ft.	$669,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 3.18% Airbnb Rental Income: $4330 Traditional Rental Income: $3852 Airbnb ROI: 2.49% Traditional ROI: 3.18%
3812 Park Blvd #209 San Diego , CA 3812 Park Blvd #209, San Diego, CA 92103 \| Condo/Coop	2 beds \| 2 baths \| 1,431 sq.ft.	$849,999	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.26% Airbnb Rental Income: $3713 Traditional Rental Income: $3535 Airbnb ROI: 0.47% Traditional ROI: 1.26%
3979 Nobel Dr #305 San Diego , CA 3979 Nobel Dr #305, San Diego, CA 92122 \| Condo/Coop	1 beds \| 1 baths \| 600 sq.ft.	$474,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.92% Airbnb Rental Income: $3339 Traditional Rental Income: $1950 Airbnb ROI: 3.36% Traditional ROI: 1.92%
4435 Nobel Dr #19 San Diego , CA 4435 Nobel Dr #19, San Diego, CA 92122 \| Condo/Coop	1 beds \| 1 baths \| 656 sq.ft.	$488,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 1.52% Airbnb Rental Income: $3339 Traditional Rental Income: $2213 Airbnb ROI: 2.36% Traditional ROI: 1.52%
1483 Caminito Diadema La Jolla , CA Single-story coastal living in La Jolla! This popular floor plan in the gated Crystal Bay ...	3 beds \| 3 baths \| 2,571 sq.ft.	$2,649,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.15% Airbnb Rental Income: $7460 Traditional Rental Income: $5207 Airbnb ROI: 0.49% Traditional ROI: 0.15%
574 26th Ave #3 San Francisco , CA 574 26th Ave #3, San Francisco, CA 94121 \| Condo/Coop	4 beds \| 3 baths \| 1,520 sq.ft.	$1,498,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 0.76% Airbnb Rental Income: $8778 Traditional Rental Income: $4342 Airbnb ROI: 2.76% Traditional ROI: 0.76%

Real Estate investment in Winchester, CA

There are 2 properties for sale in the city of Winchester . The median list price in Winchester is $1,037,500 and the average price per square foot is $432. In October 2025, the average monthly cash on cash return in Winchester is 3.00%. The average monthly rental income in Winchester is $3,391.

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

There are 2 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $1,803.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CA

33043 Wesley Street

Winchester, CA

9 beds | 6 baths | 2,272 sq.ft.

$1,075,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1714

Airbnb ROI: N/A

Traditional ROI: 0.56%

32900 Bootlegg

Winchester, CA

5 beds | 4 baths | 2,536 sq.ft.

$999,999

Airbnb cash on cash: -0.04%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $1983

Traditional Rental Income: $5554

Airbnb ROI: -0.04%

Traditional ROI: 4.35%

Investment Properties for Sale in Other Cities of California

Pacific Palisades , CA

4 beds | 3 baths | 2,781 sq.ft.

$2,895,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $14891

Traditional Rental Income: $7719

Airbnb ROI: 2.58%

Traditional ROI: 0.91%

West Hills , CA

5 beds | 5 baths | 2,515 sq.ft.

$1,480,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $3431

Traditional Rental Income: $7284

Airbnb ROI: 0.12%

Traditional ROI: 3.48%

SHERMAN OAKS , CA

5 beds | 4 baths | 3,048 sq.ft.

$1,799,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $4174

Traditional Rental Income: $8704

Airbnb ROI: 0.16%

Traditional ROI: 3.4%

SHERMAN OAKS , CA

5 beds | 5 baths | 4,222 sq.ft.

$2,444,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $4174

Traditional Rental Income: $4537

Airbnb ROI: -0.35%

Traditional ROI: 0.2%

GRANADA HILLS , CA

2 beds | 3 baths | 1,228 sq.ft.

$525,000

Airbnb cash on cash: 3.84%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $4232

Traditional Rental Income: $3214

Airbnb ROI: 3.84%

Traditional ROI: 3.58%

Chatsworth , CA

3 beds | 4 baths | 1,604 sq.ft.

$615,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $3231

Traditional Rental Income: $4797

Airbnb ROI: 2.44%

Traditional ROI: 6.44%

Woodland Hills , CA

5 beds | 4 baths | 3,806 sq.ft.

$2,199,000

Airbnb cash on cash: -0.75%