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
34826 Mediterra Circle Winchester, CA This inviting single-story residence offers comfort, space, and styleâperfect for famili...	4 beds \| 2 baths \| 2,307 sq.ft.	$655,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.62% Airbnb Rental Income: $1622 Traditional Rental Income: $3422 Airbnb ROI: -0.08% Traditional ROI: 3.62%
32591 Shadyview Street Winchester, CA This amazing home is a true gem, that seamlessly blends comfort, sophistication, and pract...	5 beds \| 4 baths \| 3,363 sq.ft.	$999,998	Airbnb cash on cash: -0.47% Traditional cash on cash: 4.18% Airbnb Rental Income: $1983 Traditional Rental Income: $5793 Airbnb ROI: -0.47% Traditional ROI: 4.18%
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: -0.06% Traditional cash on cash: 0.56% Airbnb Rental Income: $1622 Traditional Rental Income: $1714 Airbnb ROI: -0.06% Traditional ROI: 0.56%
26816 Calico Court Winchester, CA Welcome to Calico Ct! Discover the perfect blend of comfort, style, and convenience in thi...	4 beds \| 3 baths \| 2,216 sq.ft.	$552,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 4.53% Airbnb Rental Income: $1622 Traditional Rental Income: $3337 Airbnb ROI: 0.31% Traditional ROI: 4.53%
35442 Marabella Court Winchester, CA This spacious home offers 3 bedrooms, 3.5 baths, and a versatile layout. Enjoy the comfort...	3 beds \| 4 baths \| 2,082 sq.ft.	$520,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 4.74% Airbnb Rental Income: $2276 Traditional Rental Income: $3632 Airbnb ROI: 0.78% Traditional ROI: 4.74%
35582 Laurel Tree Court Winchester, CA Price Improvement! An incredible opportunity to own a turnkey home in the highly desirable...	4 beds \| 3 baths \| 2,998 sq.ft.	$834,900	Airbnb cash on cash: -0.65% Traditional cash on cash: 3.33% Airbnb Rental Income: $1622 Traditional Rental Income: $4259 Airbnb ROI: -0.65% Traditional ROI: 3.33%
35405 Calendula Cir. Winchester, CA A MUST SEE! IMMACULATE SINGLE STORY SPOOL HOME in the exclusive Morningstar Ranch. This ST...	4 beds \| 3 baths \| 2,740 sq.ft.	$799,999	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.07% Airbnb Rental Income: $1622 Traditional Rental Income: $3704 Airbnb ROI: -0.34% Traditional ROI: 3.07%
32063 Yosemite Street Winchester, CA Step into this beautifully upgraded Winchester home where curb appeal meets modern living!...	4 beds \| 3 baths \| 3,333 sq.ft.	$685,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 4.39% Airbnb Rental Income: $1622 Traditional Rental Income: $4022 Airbnb ROI: -0.08% Traditional ROI: 4.39%
31809 Delfina Way Winchester, CA MAJOR PRICE REDUCTION! Step into this meticulously maintained, light-filled 2-bed, 2-bath ...	2 beds \| 2 baths \| 1,056 sq.ft.	$400,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 4.42% Airbnb Rental Income: $1528 Traditional Rental Income: $2764 Airbnb ROI: -0.06% Traditional ROI: 4.42%
36316 Cosimo Lane Winchester, CA Welcome to resort style living at Casabella located in French Valley! Luxury at an afforda...	2 beds \| 2 baths \| 1,304 sq.ft.	$435,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.55% Airbnb Rental Income: $1528 Traditional Rental Income: $3088 Airbnb ROI: -0.37% Traditional ROI: 4.55%
28425 Pinon Court Winchester, CA Multi gen living with room for family or the guests! This newer built home has so much to ...	4 beds \| 4 baths \| 2,612 sq.ft.	$695,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.84% Airbnb Rental Income: $1622 Traditional Rental Income: $3716 Airbnb ROI: -0.1% Traditional ROI: 3.84%
29644 Bonneville Ct Winchester, CA *PAID OFF SOLAR* Beautiful 2022-Built Home with Paid Off Solar in Winchester! Welcome ...	4 beds \| 3 baths \| 2,624 sq.ft.	$649,999	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.32% Airbnb Rental Income: $1622 Traditional Rental Income: $3421 Airbnb ROI: 0.6% Traditional ROI: 4.32%
34671 Dalea Road Winchester, CA VERY LOW TAXES- NO HOA- STUNNING SINGLE STORY DREAM HOME! 3 Bedrooms with 2.5 Bathrooms....	3 beds \| 3 baths \| 2,447 sq.ft.	$709,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.21% Airbnb Rental Income: $2276 Traditional Rental Income: $3221 Airbnb ROI: 0.92% Traditional ROI: 3.21%
36462 Sweet Berry Court Winchester, CA Welcome to 36462 Sweet Berry Ct, a spacious corner-lot home featuring 4 bedrooms, 4 baths,...	5 beds \| 4 baths \| 3,912 sq.ft.	$699,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.87% Airbnb Rental Income: $1983 Traditional Rental Income: $4112 Airbnb ROI: -0.19% Traditional ROI: 3.87%
31138 Euclid Loop Winchester, CA Coming Soonâa charming single-story home in a sought-after Winchester neighborhood. This...	4 beds \| 2 baths \| 1,843 sq.ft.	$649,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.26% Airbnb Rental Income: $1622 Traditional Rental Income: $3141 Airbnb ROI: -0.01% Traditional ROI: 3.26%
31659 Poppy Street Winchester, CA Tastefully remodeled home near Temecula's wine country. Offering four bedrooms, three full...	4 beds \| 3 baths \| 3,037 sq.ft.	$765,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.12% Airbnb Rental Income: $1622 Traditional Rental Income: $3604 Airbnb ROI: -0.3% Traditional ROI: 3.12%
35543 Laurel Tree Court Winchester, CA Luxury Single-Story with Designer Upgrades & Breathtaking Views! Welcome to this stunning ...	3 beds \| 3 baths \| 2,560 sq.ft.	$865,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 2.38% Airbnb Rental Income: $2276 Traditional Rental Income: $3483 Airbnb ROI: 0.18% Traditional ROI: 2.38%
34250 Olive Avenue Winchester, CA Welcome to 34250 Olive Ave, located in the THRIVING City of Winchester, Ca. This incredibl...	5 beds \| 3 baths \| 1,800 sq.ft.	$8,499,989	Airbnb cash on cash: -1.58% Traditional cash on cash: -1.28% Airbnb Rental Income: $1983 Traditional Rental Income: $3850 Airbnb ROI: -1.58% Traditional ROI: -1.28%
29604 Kyles Circle Winchester, CA Contact Complete Real Estate at 951-676-5820 for additional info. Better than new, this am...	3 beds \| 3 baths \| 2,054 sq.ft.	$524,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 4.55% Airbnb Rental Income: $2276 Traditional Rental Income: $3257 Airbnb ROI: 1.39% Traditional ROI: 4.55%
32581 Prairie Crossing Drive Winchester, CA LOOKING FOR A SINGLE LEVEL HOME? DON'T MISS THIS BEAUTIFUL, CORNER, CALIFORNIA SPANISH STY...	4 beds \| 3 baths \| 2,319 sq.ft.	$649,500	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.02% Airbnb Rental Income: $1622 Traditional Rental Income: $3701 Airbnb ROI: -0.17% Traditional ROI: 4.02%
32526 Presidio Hills Lane Winchester, CA Don't miss this incredibly beautiful home just reduced and ready to make family memories f...	5 beds \| 3 baths \| 3,213 sq.ft.	$814,999	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.33% Airbnb Rental Income: $1983 Traditional Rental Income: $4242 Airbnb ROI: -0.33% Traditional ROI: 3.33%
32144 Yosemite Street Winchester, CA Location, Privacy & Breathtaking ViewsâThis Home Has It All! Welcome to your dream retr...	4 beds \| 3 baths \| 2,771 sq.ft.	$1,024,990	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.52% Airbnb Rental Income: $1622 Traditional Rental Income: $4293 Airbnb ROI: -0.77% Traditional ROI: 2.52%
34936 Old Vine Road Winchester, CA Location, Location, Location!!! This amazing POOL home is very close to amazing schools (w...	4 beds \| 3 baths \| 2,320 sq.ft.	$700,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 2.44% Airbnb Rental Income: $1622 Traditional Rental Income: $3373 Airbnb ROI: -0.95% Traditional ROI: 2.44%
33761 Leon Rd Winchester, CA Welcome to this incredible 5-acre lot property located on a prime corner in the fast-growi...	3 beds \| 3 baths \| 2,040 sq.ft.	$939,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.22% Airbnb Rental Income: $2276 Traditional Rental Income: $3482 Airbnb ROI: 0.19% Traditional ROI: 2.22%
32593 Cumulus Lane Winchester, CA Welcome to 32593 Cumulus Lane, a thoughtfully designed home featuring an open-concept layo...	4 beds \| 3 baths \| 2,239 sq.ft.	$649,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.43% Airbnb Rental Income: $1622 Traditional Rental Income: $3722 Airbnb ROI: -0.79% Traditional ROI: 3.43%
31556 Umbria Ln. Winchester, CA An Exceptional Residence in Winchester Welcome to a home where comfort, and modern living...	4 beds \| 3 baths \| 2,492 sq.ft.	$660,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.53% Airbnb Rental Income: $1622 Traditional Rental Income: $3530 Airbnb ROI: -0.31% Traditional ROI: 3.53%
30853 Pony Express Drive Winchester, CA Welcome to this beautiful home located in the desirable community of Winchester, CA! This ...	4 beds \| 3 baths \| 2,227 sq.ft.	$614,500	Airbnb cash on cash: -0.83% Traditional cash on cash: 3.35% Airbnb Rental Income: $1622 Traditional Rental Income: $3561 Airbnb ROI: -0.83% Traditional ROI: 3.35%
32768 Westport Way Winchester, CA Elegant, open concept 4 bedroom home. Well maintained, spacious rooms, with bonus rooms p...	4 beds \| 3 baths \| 2,647 sq.ft.	$719,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.24% Airbnb Rental Income: $1622 Traditional Rental Income: $3465 Airbnb ROI: -0.2% Traditional ROI: 3.24%
32181 Kale Lane Winchester, CA Just Reduced! Beautiful Single Story Home with NO HOA, VERY LOW TAXES and Temecula Schools...	3 beds \| 2 baths \| 1,690 sq.ft.	$578,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.97% Airbnb Rental Income: $2276 Traditional Rental Income: $3138 Airbnb ROI: 1.32% Traditional ROI: 3.97%
36055 Maddalena Road Winchester, CA Expansive and usable 2.5 acre lot with a beautiful home on it is located in beautiful Winc...	5 beds \| 3 baths \| 1,988 sq.ft.	$899,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.74% Airbnb Rental Income: $1983 Traditional Rental Income: $3851 Airbnb ROI: -0.12% Traditional ROI: 2.74%
33168 Toledo Bend Court Winchester, CA PRICE IMPROVEMENT! STUNNING EXECUTIVE LENNAR NEXT GEN/ADU home nestled in the rapidly grow...	5 beds \| 4 baths \| 4,134 sq.ft.	$885,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 5.7% Airbnb Rental Income: $1983 Traditional Rental Income: $6237 Airbnb ROI: -0.09% Traditional ROI: 5.7%
29392 Tourmaline Way Winchester, CA PRICED WELL BELOW MARKET - LOTS OF ROOM FOR INSTANT EQUITY! SOLAR IS PAID OFF!! SELLER ...	3 beds \| 3 baths \| 1,397 sq.ft.	$494,999	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.35% Airbnb Rental Income: $2276 Traditional Rental Income: $3066 Airbnb ROI: 1.41% Traditional ROI: 4.35%
29425 Bovenzi Way Winchester, CA Welcome to Copper Sky, one of Winchesterâs most desirable communities by Tri Pointe Home...	3 beds \| 3 baths \| 1,754 sq.ft.	$510,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.13% Airbnb Rental Income: $2276 Traditional Rental Income: $3498 Airbnb ROI: 0.38% Traditional ROI: 4.13%
35604 Suzette Court Winchester, CA Step into beauty and comfort in this immaculate 3-bedroom home, complete with a large bonu...	3 beds \| 3 baths \| 2,415 sq.ft.	$659,999	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.57% Airbnb Rental Income: $2276 Traditional Rental Income: $3413 Airbnb ROI: 0.8% Traditional ROI: 3.57%
32433 Marietta Court Winchester, CA Welcome to this previous model home. 5 bedrooms 3.5 baths, an office and a 4 car tandem ga...	5 beds \| 4 baths \| 3,369 sq.ft.	$1,000,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 3.32% Airbnb Rental Income: $1983 Traditional Rental Income: $5400 Airbnb ROI: -0.91% Traditional ROI: 3.32%
32684 Salvia Circle Winchester, CA Executive Living in the Desirable Morning Star Ranch Community of Winchester Welcome to t...	4 beds \| 3 baths \| 3,157 sq.ft.	$775,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.97% Airbnb Rental Income: $1622 Traditional Rental Income: $3683 Airbnb ROI: -0.52% Traditional ROI: 2.97%
31771 Biagio Way Winchester, CA **This Beautiful Condo located in the extremely well-kept Casabella Community is the ideal...	3 beds \| 3 baths \| 1,696 sq.ft.	$463,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.95% Airbnb Rental Income: $2276 Traditional Rental Income: $3142 Airbnb ROI: 0.64% Traditional ROI: 3.95%
30876 Epiplaneia Way Winchester, CA Seller is willing to pay closing cost!!! Jump on this amazing opportunity. House is a 3 be...	3 beds \| 2 baths \| 1,152 sq.ft.	$699,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.68% Airbnb Rental Income: $2276 Traditional Rental Income: $2982 Airbnb ROI: 0.72% Traditional ROI: 2.68%
30982 Foxhollow Drive Winchester, CA Absolutely Gorgeous!! This incredible single-story ranch style home sits on an amazing and...	4 beds \| 3 baths \| 2,474 sq.ft.	$600,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 4.21% Airbnb Rental Income: $1622 Traditional Rental Income: $3822 Airbnb ROI: -0.54% Traditional ROI: 4.21%
29363 Water Glass Court Winchester, CA Discover comfort and convenience in this light-filled, two-story detached condo located in...	3 beds \| 3 baths \| 1,397 sq.ft.	$505,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.68% Airbnb Rental Income: $2276 Traditional Rental Income: $3246 Airbnb ROI: 1.42% Traditional ROI: 4.68%

Real Estate investment in Winchester, CA

There are 80 properties for sale in the city of Winchester . The median list price in Winchester is $656,500 and the average price per square foot is $286. In October 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,530.

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

There are 80 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 $1,983.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CA

34826 Mediterra Circle

Winchester, CA

4 beds | 2 baths | 2,307 sq.ft.

$655,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1622

Traditional Rental Income: $3422

Airbnb ROI: -0.08%

Traditional ROI: 3.62%

32591 Shadyview Street

Winchester, CA

5 beds | 4 baths | 3,363 sq.ft.

$999,998

Airbnb cash on cash: -0.47%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $1983

Traditional Rental Income: $5793

Airbnb ROI: -0.47%

Traditional ROI: 4.18%

33043 Wesley Street

Winchester, CA

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

$1,075,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 0.56%

Airbnb Rental Income: $1622

Traditional Rental Income: $1714

Airbnb ROI: -0.06%

Traditional ROI: 0.56%

26816 Calico Court

Winchester, CA

4 beds | 3 baths | 2,216 sq.ft.

$552,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1622

Traditional Rental Income: $3337

Airbnb ROI: 0.31%

Traditional ROI: 4.53%

35442 Marabella Court

Winchester, CA

3 beds | 4 baths | 2,082 sq.ft.

$520,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $2276

Traditional Rental Income: $3632

Airbnb ROI: 0.78%

Traditional ROI: 4.74%

35582 Laurel Tree Court

Winchester, CA

4 beds | 3 baths | 2,998 sq.ft.

$834,900

Airbnb cash on cash: -0.65%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $1622

Traditional Rental Income: $4259

Airbnb ROI: -0.65%

Traditional ROI: 3.33%

35405 Calendula Cir.

Winchester, CA

4 beds | 3 baths | 2,740 sq.ft.

$799,999

Airbnb cash on cash: -0.34%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $1622

Traditional Rental Income: $3704

Airbnb ROI: -0.34%

Traditional ROI: 3.07%

32063 Yosemite Street

Winchester, CA

4 beds | 3 baths | 3,333 sq.ft.

$685,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $1622

Traditional Rental Income: $4022

Airbnb ROI: -0.08%