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.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.67% Airbnb Rental Income: $null Traditional Rental Income: $1714 Airbnb ROI: N/A Traditional ROI: 0.67%
36675 Sauterne Street Winchester, CA This beautifully upgraded home features 4 bedrooms, 2 baths, fresh exterior paint, and stu...	4 beds \| 2 baths \| 1,720 sq.ft.	$660,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.03% Airbnb Rental Income: $1622 Traditional Rental Income: $3010 Airbnb ROI: 0.03% Traditional ROI: 3.03%
29382 Marblewood Court Winchester, CA Welcome to this stunning Winchester home, ideally situated on a quiet cul-de-sac with brea...	4 beds \| 3 baths \| 1,972 sq.ft.	$599,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.47% Airbnb Rental Income: $1622 Traditional Rental Income: $3240 Airbnb ROI: 0.77% Traditional ROI: 4.47%
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.	$775,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.22% Airbnb Rental Income: $1622 Traditional Rental Income: $3704 Airbnb ROI: -0.3% Traditional ROI: 3.22%
32431 Roman Warren Way Winchester, CA Looking for space? This home sits on a huge 9,000+ sq ft lotâplenty of room to entertain...	3 beds \| 2 baths \| 2,021 sq.ft.	$610,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.04% Airbnb Rental Income: $2276 Traditional Rental Income: $3392 Airbnb ROI: 1.08% Traditional ROI: 4.04%
34184 Pink Place Winchester, CA Discover the perfect blend of new construction luxury, custom upgrades, and modern design ...	4 beds \| 3 baths \| 3,035 sq.ft.	$724,999	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.46% Airbnb Rental Income: $1622 Traditional Rental Income: $3711 Airbnb ROI: -0.31% Traditional ROI: 3.46%
31659 Poppy St Winchester, CA Tastefully remodeled home near Temecula's wine country. Offering four bedrooms, three full...	4 beds \| 3 baths \| 3,037 sq.ft.	$775,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.07% Airbnb Rental Income: $1622 Traditional Rental Income: $3604 Airbnb ROI: -0.31% Traditional ROI: 3.07%
30927 Tempest Court Winchester, CA Welcome to your new home in the heart of Winchester at Pradera Place! This stunning newly ...	3 beds \| 2 baths \| 1,375 sq.ft.	$499,999	Airbnb cash on cash: 1.42% Traditional cash on cash: 3.87% Airbnb Rental Income: $2276 Traditional Rental Income: $2852 Airbnb ROI: 1.42% Traditional ROI: 3.87%
30551 Bel Air Court Winchester, CA Welcome to this nearly new, energy-efficient 4-bedroom, 2.5-bath home built in 2024 by DR ...	4 beds \| 2 baths \| 1,835 sq.ft.	$559,999	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.88% Airbnb Rental Income: $1622 Traditional Rental Income: $3152 Airbnb ROI: 0.07% Traditional ROI: 3.88%
28386 Corvair Court Winchester, CA Dreaming of a new construction home? Look no further. This barely lived-in, nearly brand-...	3 beds \| 3 baths \| 1,567 sq.ft.	$554,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.54% Airbnb Rental Income: $2276 Traditional Rental Income: $2966 Airbnb ROI: 1.11% Traditional ROI: 3.54%
32297 Wild West Court Winchester, CA Beautifully maintained single-story home offering the perfect blend of comfort, style, and...	4 beds \| 2 baths \| 2,033 sq.ft.	$598,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.81% Airbnb Rental Income: $1622 Traditional Rental Income: $3209 Airbnb ROI: -0.85% Traditional ROI: 2.81%
32198 Rambling Court Winchester, CA This charming 4-bedroom, 3-bath home spans 2,591 sqft on a spacious 6,970 sqft lot, ensuri...	4 beds \| 3 baths \| 2,591 sq.ft.	$625,240	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.39% Airbnb Rental Income: $1622 Traditional Rental Income: $3685 Airbnb ROI: -0.94% Traditional ROI: 3.39%
34495 Agave Dr #20106 Winchester, CA Back on Market!!! Don't miss your chance to Check out this 2024 home, located in the heart...	3 beds \| 2 baths \| 1,484 sq.ft.	$455,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.65% Airbnb Rental Income: $2276 Traditional Rental Income: $3204 Airbnb ROI: 1.13% Traditional ROI: 4.65%
31556 Umbria Ln Winchester, CA Exceptional Brindisi Community Home Offering Style, Comfort, and Modern Living! This st...	4 beds \| 3 baths \| 2,492 sq.ft.	$649,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.61% Airbnb Rental Income: $1622 Traditional Rental Income: $3530 Airbnb ROI: -0.3% Traditional ROI: 3.61%
34495 Agave Dr #34103 Winchester, CA Sevilla View Home! VA Approved! Fast move in OK. This never-lived-in townhome features lux...	3 beds \| 2 baths \| 1,399 sq.ft.	$479,950	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.69% Airbnb Rental Income: $2276 Traditional Rental Income: $3215 Airbnb ROI: 0.33% Traditional ROI: 3.69%
30560 Paul Lane Winchester, CA This spacious two-story home in Winchester offers elevated comfort, generous living spaces...	4 beds \| 3 baths \| 2,503 sq.ft.	$643,990	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.13% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.03% Traditional ROI: 4.13%
30548 Paul Lane Winchester, CA This brand new two-story home in Winchester comes with no HOA fees and is designed for eas...	3 beds \| 2 baths \| 2,274 sq.ft.	$599,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.2% Airbnb Rental Income: $2276 Traditional Rental Income: $3427 Airbnb ROI: 1.13% Traditional ROI: 4.2%
30536 Paul Lane Winchester, CA This brand new two-story home in Winchester comes with no HOA fees and is designed for eas...	3 beds \| 2 baths \| 2,033 sq.ft.	$579,990	Airbnb cash on cash: 1.23% Traditional cash on cash: 4.23% Airbnb Rental Income: $2276 Traditional Rental Income: $3333 Airbnb ROI: 1.23% Traditional ROI: 4.23%
29425 Bovenzi Way Winchester, CA Welcome to Copper Sky, one of Winchesterâs most desirable communities by Tri Pointe Home...	3 beds \| 2 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%
34495 Agave Dr #34107 Winchester, CA MODEl HOME! Fast move in OK! Welcome to this charming two-story townhome in the desirable ...	3 beds \| 2 baths \| 1,399 sq.ft.	$469,950	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.84% Airbnb Rental Income: $2276 Traditional Rental Income: $3215 Airbnb ROI: 0.42% Traditional ROI: 3.84%
34495 Agave Dr #10110 Winchester, CA Stunning, Move-In Ready Townhome with Fully Paid Solar in Temeculaâs Top School District...	3 beds \| 2 baths \| 1,408 sq.ft.	$460,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.55% Airbnb Rental Income: $2276 Traditional Rental Income: $3163 Airbnb ROI: 0.17% Traditional ROI: 3.55%
32684 Salvia Cir Winchester, CA Executive Living in the Highly Desirable Morning Star Ranch Community of Winchester Welco...	4 beds \| 2 baths \| 3,157 sq.ft.	$765,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.02% Airbnb Rental Income: $1622 Traditional Rental Income: $3683 Airbnb ROI: -0.51% Traditional ROI: 3.02%
33305 Rusty Court Winchester, CA This stunning two-story home offers four bedrooms and is perfectly situated within the Tem...	4 beds \| 3 baths \| 2,429 sq.ft.	$659,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 4.14% Airbnb Rental Income: $1622 Traditional Rental Income: $3722 Airbnb ROI: -0.02% Traditional ROI: 4.14%
31309 Van Ruysdael Ln Winchester, CA Welcome to 31309 Van Ruysdael Ln, Winchester! This charming 3-bedroom, 2-bathroom single-...	3 beds \| 2 baths \| 1,509 sq.ft.	$599,999	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.7% Airbnb Rental Income: $2276 Traditional Rental Income: $3231 Airbnb ROI: 0.98% Traditional ROI: 3.7%
33063 Table Rock Drive Winchester, CA Turnkey 4-Bedroom Home with Designer Upgrades in Temecula â PAID FOR SOLAR, Built in 202...	4 beds \| 3 baths \| 2,590 sq.ft.	$725,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 3.03% Airbnb Rental Income: $1622 Traditional Rental Income: $3912 Airbnb ROI: -1.04% Traditional ROI: 3.03%
31289 Pine Oak Road Winchester, CA Beautiful Hudson community- KBhome's newest Community in Winchester, CA with all electric,...	4 beds \| 3 baths \| 1,741 sq.ft.	$684,990	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.22% Airbnb Rental Income: $1622 Traditional Rental Income: $3272 Airbnb ROI: -0.08% Traditional ROI: 3.22%
30709 Expedition Drive Winchester, CA Welcome to this 4-bedroom, 3-bathroom home with 2,277 sq. ft. of living space, built in 20...	4 beds \| 3 baths \| 2,227 sq.ft.	$615,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.77% Airbnb Rental Income: $1622 Traditional Rental Income: $3772 Airbnb ROI: -0.78% Traditional ROI: 3.77%
31579 Mccartney Dr Winchester, CA Popular single-story home on a Corner Lot with Open Floorplan. No rear neighbors! 3 Spacio...	3 beds \| 2 baths \| 1,856 sq.ft.	$610,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.72% Airbnb Rental Income: $2276 Traditional Rental Income: $3277 Airbnb ROI: 0.96% Traditional ROI: 3.72%
29212 Santa Fe Springs Court Winchester, CA Highlights of the two-story Leander plan include open dining and great rooms, a main-floor...	4 beds \| 3 baths \| 1,992 sq.ft.	$597,990	Airbnb cash on cash: -0.12% Traditional cash on cash: 4.22% Airbnb Rental Income: $1622 Traditional Rental Income: $3585 Airbnb ROI: -0.12% Traditional ROI: 4.22%
31354 Trappers Loop Winchester, CA The two-story Lark plan greets guests with a welcoming covered porch and continues to impr...	4 beds \| 2 baths \| 1,912 sq.ft.	$584,990	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.91% Airbnb Rental Income: $1622 Traditional Rental Income: $3342 Airbnb ROI: -0.08% Traditional ROI: 3.91%
35056 Knollview Winchester, CA Welcome to Horizon at Morningstar Ranch! Tucked away on a quiet cul-de-sac in one of the ...	4 beds \| 3 baths \| 3,369 sq.ft.	$795,500	Airbnb cash on cash: -1.09% Traditional cash on cash: 4.56% Airbnb Rental Income: $1622 Traditional Rental Income: $5352 Airbnb ROI: -1.09% Traditional ROI: 4.56%

Real Estate investment in Winchester, CA

There are 221 properties for sale in the city of Winchester . The median list price in Winchester is $624,990 and the average price per square foot is $285. In February 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,410.

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

There are 221 investment properties available for sale in Winchester.

In 2026, 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

33043 Wesley Street

Winchester, CA

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

$899,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.67%

Airbnb Rental Income: $null

Traditional Rental Income: $1714

Airbnb ROI: N/A

Traditional ROI: 0.67%

36675 Sauterne Street

Winchester, CA

4 beds | 2 baths | 1,720 sq.ft.

$660,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $1622

Traditional Rental Income: $3010

Airbnb ROI: 0.03%

Traditional ROI: 3.03%

29382 Marblewood Court

Winchester, CA

4 beds | 3 baths | 1,972 sq.ft.

$599,900

Airbnb cash on cash: 0.77%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $1622

Traditional Rental Income: $3240

Airbnb ROI: 0.77%

Traditional ROI: 4.47%

35405 Calendula Cir

Winchester, CA

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

$775,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1622

Traditional Rental Income: $3704

Airbnb ROI: -0.3%

Traditional ROI: 3.22%

32431 Roman Warren Way

Winchester, CA

3 beds | 2 baths | 2,021 sq.ft.

$610,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $2276

Traditional Rental Income: $3392

Airbnb ROI: 1.08%

Traditional ROI: 4.04%

34184 Pink Place

Winchester, CA

4 beds | 3 baths | 3,035 sq.ft.

$724,999

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1622

Traditional Rental Income: $3711

Airbnb ROI: -0.31%

Traditional ROI: 3.46%

31659 Poppy St

Winchester, CA

4 beds | 3 baths | 3,037 sq.ft.

$775,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $1622

Traditional Rental Income: $3604

Airbnb ROI: -0.31%

Traditional ROI: 3.07%

30927 Tempest Court

Winchester, CA

3 beds | 2 baths | 1,375 sq.ft.

$499,999

Airbnb cash on cash: 1.42%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $2276

Traditional Rental Income: $2852

Airbnb ROI: 1.42%