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
29339 Opal Skye Way Winchester, CA Don't miss out â this is your last chance to make Opal Skye home! This stunning model ho...	3 beds \| 2 baths \| 1,882 sq.ft.	$539,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.82% Airbnb Rental Income: $2276 Traditional Rental Income: $3087 Airbnb ROI: 1.08% Traditional ROI: 3.82%
29500 Opal Skye Way Winchester, CA Move-in Ready! Plan 5 at Opal Skye offers the perfect balance of comfort and space in this...	3 beds \| 2 baths \| 1,882 sq.ft.	$484,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.61% Airbnb Rental Income: $2276 Traditional Rental Income: $3159 Airbnb ROI: 1.4% Traditional ROI: 4.61%
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%
34929 Sage Canyon Court Winchester, CA UPGRADED \| SINGLE STORY \| CUL-DE-SAC \| SOLAR PANELS \| 10,000+ SQFT LOT \| LOW TAXES \| LOW H...	3 beds \| 2 baths \| 2,217 sq.ft.	$600,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3% Airbnb Rental Income: $2276 Traditional Rental Income: $3112 Airbnb ROI: 0.49% Traditional ROI: 3%
36358 Matino Lane Winchester, CA This beautifully maintained home offers an inviting open-concept layout perfect for both e...	3 beds \| 2 baths \| 1,550 sq.ft.	$454,998	Airbnb cash on cash: 1.03% Traditional cash on cash: 4.11% Airbnb Rental Income: $2276 Traditional Rental Income: $3019 Airbnb ROI: 1.03% Traditional ROI: 4.11%
35059 KNOLLVIEW COURT Winchester, CA * * * Price Improvement * * * Welcome to Your Private Resort Oasis at 35059 Knollview Ct,...	4 beds \| 3 baths \| 3,213 sq.ft.	$898,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.82% Airbnb Rental Income: $1622 Traditional Rental Income: $4159 Airbnb ROI: -0.77% Traditional ROI: 2.82%
29046 Delores Lane Winchester, CA Welcome to this charming 3-bedroom, 2-bathroom Spanish-style home in the heart of Winchest...	3 beds \| 2 baths \| 1,750 sq.ft.	$565,880	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.7% Airbnb Rental Income: $2276 Traditional Rental Income: $3185 Airbnb ROI: 1.9% Traditional ROI: 4.7%
35908 Curie Court Winchester, CA Beautifully remodeled single-story home in the desirable French Valley community. This hom...	4 beds \| 2 baths \| 1,749 sq.ft.	$591,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.71% Airbnb Rental Income: $1622 Traditional Rental Income: $3146 Airbnb ROI: 0.12% Traditional ROI: 3.71%
29460 Bamboo Court Winchester, CA Your Dream Home AwaitsâMountain Views, Modern Comfort, and a Warm Welcome from the Momen...	3 beds \| 2 baths \| 1,868 sq.ft.	$585,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.4% Airbnb Rental Income: $2276 Traditional Rental Income: $2912 Airbnb ROI: 1.2% Traditional ROI: 3.4%
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%
29644 Bonneville Court Winchester, CA OWNED SOLAR!! BUILT IN 2022 - 4 BEDROOMS + LOFT + DOWNSTAIRS BED & BATH ON A CUL-DE-SAC!! ...	4 beds \| 3 baths \| 2,624 sq.ft.	$644,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 4.37% Airbnb Rental Income: $1622 Traditional Rental Income: $3421 Airbnb ROI: 0.61% Traditional ROI: 4.37%
34611 Persian Lilac Street Winchester, CA Beautiful Move-In Ready Home - See this before you buy elsewhere! Welcome to this beautif...	4 beds \| 3 baths \| 2,821 sq.ft.	$769,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.74% Airbnb Rental Income: $1622 Traditional Rental Income: $3683 Airbnb ROI: -0.78% Traditional ROI: 2.74%
34671 Dalea Road Winchester, CA VERY LOW TAXES- NO HOA- STUNNING SINGLE STORY DREAM HOME! 3 Bedrooms with 2.5 Bathrooms....	3 beds \| 2 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%
33143 Big Range Drive Winchester, CA Nestled within the desirable newer community of Winchester Trails, this property is a true...	4 beds \| 3 baths \| 2,273 sq.ft.	$579,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.81% Airbnb Rental Income: $1622 Traditional Rental Income: $3191 Airbnb ROI: 0.06% Traditional ROI: 3.81%
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.	$517,500	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.68% Airbnb Rental Income: $2276 Traditional Rental Income: $2852 Airbnb ROI: 1.32% Traditional ROI: 3.68%
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%
34936 Old Vine Road Winchester, CA Hot New Price!!! Amazing home in a great Location!!! This amazing POOL home is very close ...	4 beds \| 2 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 This property features paid-off solar, its own water well, and a well-maintained septic sy...	3 beds \| 3 baths \| 2,040 sq.ft.	$869,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.48% Airbnb Rental Income: $2276 Traditional Rental Income: $3482 Airbnb ROI: 0.29% Traditional ROI: 2.48%
29388 Opal Skye Way Winchester, CA Move-in Ready! Donât miss your final chance to own a home with Plan 6 at Opal Skye! This...	3 beds \| 2 baths \| 2,054 sq.ft.	$529,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 4.87% Airbnb Rental Income: $2276 Traditional Rental Income: $3545 Airbnb ROI: 1.16% Traditional ROI: 4.87%
31556 Umbria Ln. Winchester, CA Back on the Market! Exceptional Residence in the most desirable Community of Brindisi. Wh...	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%
32768 Westport Way Winchester, CA Elegant, open concept 4 bedroom home. Well maintained, spacious rooms, with bonus rooms p...	4 beds \| 2 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%
34495 Agave Drive #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.	$485,950	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.63% Airbnb Rental Income: $2276 Traditional Rental Income: $3215 Airbnb ROI: 0.32% Traditional ROI: 3.63%
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.	$650,990	Airbnb cash on cash: 0.01% Traditional cash on cash: 4.07% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.01% Traditional ROI: 4.07%
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.	$624,990	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.96% Airbnb Rental Income: $2276 Traditional Rental Income: $3427 Airbnb ROI: 1.01% Traditional ROI: 3.96%
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.	$610,990	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.93% Airbnb Rental Income: $2276 Traditional Rental Income: $3333 Airbnb ROI: 1.08% Traditional ROI: 3.93%
29550 Woodcreek Trail Winchester, CA Welcome to this stylish and energy-efficient 4-bedroom, 3-bath home with everything youâ...	4 beds \| 3 baths \| 2,722 sq.ft.	$640,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.51% Airbnb Rental Income: $1622 Traditional Rental Income: $3797 Airbnb ROI: -0.9% Traditional ROI: 3.51%
34495 Agave Drive #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.	$475,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.79% Airbnb Rental Income: $2276 Traditional Rental Income: $3215 Airbnb ROI: 0.4% Traditional ROI: 3.79%
32684 Salvia Circle Winchester, CA Executive Living in the Highly Desirable Morning Star Ranch Community of Winchester Welco...	4 beds \| 2 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%
31664 Viviante Drive Winchester, CA NEW CONSTRUCTION! Ready for Quick Move-in! Includes Upgraded Flooring! This new four-bedro...	4 beds \| 3 baths \| 2,597 sq.ft.	$669,290	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.63% Airbnb Rental Income: $1622 Traditional Rental Income: $3851 Airbnb ROI: -0.68% Traditional ROI: 3.63%
31771 Biagio Way Winchester, CA **This Beautiful Condo located in the extremely well-kept Casabella Community is the ideal...	3 beds \| 2 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%
33057 Powell Lane Winchester, CA Back on Market. Buyer Could Not Perform. Your Dream Pool Home Awaits! Prepare to fall i...	3 beds \| 2 baths \| 1,611 sq.ft.	$639,400	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.66% Airbnb Rental Income: $2276 Traditional Rental Income: $3249 Airbnb ROI: 0.07% Traditional ROI: 2.66%
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%
28307 Memory Lane Winchester, CA Welcome to this stunning 4-bedroom, 3.5 bathroom single-family home, built in 2022 and loc...	4 beds \| 3 baths \| 2,612 sq.ft.	$699,999	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.83% Airbnb Rental Income: $1622 Traditional Rental Income: $3639 Airbnb ROI: -0.96% Traditional ROI: 2.83%
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%
29213 Victoria Beach Boulevard Winchester, CA New Construction â Ready Now! Built by America's Most Trusted Homebuilder. Welcome to th...	4 beds \| 3 baths \| 2,375 sq.ft.	$549,990	Airbnb cash on cash: 0.55% Traditional cash on cash: 5.35% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.55% Traditional ROI: 5.35%
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.	$759,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 2.85% Airbnb Rental Income: $1622 Traditional Rental Income: $3912 Airbnb ROI: -1.03% Traditional ROI: 2.85%
33157 Big Range Drive Winchester, CA PAID SOLAR! LOW TAXES AND LOW HOA! TURN-KEY HOME, WITH NEXT-GEN SUITE AND RARE DOWNSTAIRS ...	4 beds \| 2 baths \| 2,273 sq.ft.	$549,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 4.37% Airbnb Rental Income: $1622 Traditional Rental Income: $3584 Airbnb ROI: -0.34% Traditional ROI: 4.37%
35591 Denver Circle Winchester, CA ASSUMABLE LOAN AT 2.25%! TURNKEY SINGLE-LEVEL HOME ON A QUIET CUL-DE-SAC! LOW HOA, LOW TAX...	3 beds \| 2 baths \| 1,856 sq.ft.	$599,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.97% Airbnb Rental Income: $2276 Traditional Rental Income: $3436 Airbnb ROI: 0.88% Traditional ROI: 3.97%

Real Estate investment in Winchester, CA

There are 155 properties for sale in the city of Winchester . The median list price in Winchester is $599,500 and the average price per square foot is $291. In December 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,416.

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

There are 155 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

29339 Opal Skye Way

Winchester, CA

3 beds | 2 baths | 1,882 sq.ft.

$539,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $2276

Traditional Rental Income: $3087

Airbnb ROI: 1.08%

Traditional ROI: 3.82%

29500 Opal Skye Way

Winchester, CA

3 beds | 2 baths | 1,882 sq.ft.

$484,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $2276

Traditional Rental Income: $3159

Airbnb ROI: 1.4%

Traditional ROI: 4.61%

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%

34929 Sage Canyon Court

Winchester, CA

3 beds | 2 baths | 2,217 sq.ft.

$600,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 3%

Airbnb Rental Income: $2276

Traditional Rental Income: $3112

Airbnb ROI: 0.49%

Traditional ROI: 3%

36358 Matino Lane

Winchester, CA

3 beds | 2 baths | 1,550 sq.ft.

$454,998

Airbnb cash on cash: 1.03%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $2276

Traditional Rental Income: $3019

Airbnb ROI: 1.03%

Traditional ROI: 4.11%

35059 KNOLLVIEW COURT

Winchester, CA

4 beds | 3 baths | 3,213 sq.ft.

$898,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $1622

Traditional Rental Income: $4159

Airbnb ROI: -0.77%

Traditional ROI: 2.82%

29046 Delores Lane

Winchester, CA

3 beds | 2 baths | 1,750 sq.ft.

$565,880

Airbnb cash on cash: 1.9%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $2276

Traditional Rental Income: $3185

Airbnb ROI: 1.9%

Traditional ROI: 4.7%

35908 Curie Court

Winchester, CA

4 beds | 2 baths | 1,749 sq.ft.

$591,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1622

Traditional Rental Income: $3146

Airbnb ROI: 0.12%