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%
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.	$535,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.02% Airbnb Rental Income: $2276 Traditional Rental Income: $3185 Airbnb ROI: 2.07% Traditional ROI: 5.02%
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.	$580,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 3.45% Airbnb Rental Income: $2276 Traditional Rental Income: $2912 Airbnb ROI: 1.23% Traditional ROI: 3.45%
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.	$749,999	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.29% Airbnb Rental Income: $1622 Traditional Rental Income: $3711 Airbnb ROI: -0.36% Traditional ROI: 3.29%
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.	$510,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.76% Airbnb Rental Income: $2276 Traditional Rental Income: $2852 Airbnb ROI: 1.36% Traditional ROI: 3.76%
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: 1.09% Traditional cash on cash: 3.52% Airbnb Rental Income: $2276 Traditional Rental Income: $2966 Airbnb ROI: 1.09% Traditional ROI: 3.52%
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%
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%
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%
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.	$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.	$639,990	Airbnb cash on cash: 0.04% Traditional cash on cash: 4.17% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.04% Traditional ROI: 4.17%
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.	$619,990	Airbnb cash on cash: 1.03% Traditional cash on cash: 4.01% Airbnb Rental Income: $2276 Traditional Rental Income: $3427 Airbnb ROI: 1.03% Traditional ROI: 4.01%
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.	$599,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.03% Airbnb Rental Income: $2276 Traditional Rental Income: $3333 Airbnb ROI: 1.13% Traditional ROI: 4.03%
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 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.	$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%
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.	$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%
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.	$654,290	Airbnb cash on cash: -0.65% Traditional cash on cash: 3.75% Airbnb Rental Income: $1622 Traditional Rental Income: $3851 Airbnb ROI: -0.65% Traditional ROI: 3.75%
31771 Biagio Way Winchester, CA Now Move-In Ready. **This Beautiful, Condo located in the extremely well-kept Casabella C...	3 beds \| 2 baths \| 1,696 sq.ft.	$459,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.99% Airbnb Rental Income: $2276 Traditional Rental Income: $3142 Airbnb ROI: 0.66% Traditional ROI: 3.99%
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.	$729,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 3% Airbnb Rental Income: $1622 Traditional Rental Income: $3912 Airbnb ROI: -1.04% Traditional ROI: 3%
31300 Pine Oak Road Winchester, CA Beautiful Hudson community KBhome's newest Community in Winchester, CA with electric, sola...	3 beds \| 2 baths \| 1,741 sq.ft.	$598,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.82% Airbnb Rental Income: $2276 Traditional Rental Income: $3211 Airbnb ROI: 1.13% Traditional ROI: 3.82%
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.	$639,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.58% Airbnb Rental Income: $1622 Traditional Rental Income: $3772 Airbnb ROI: -0.79% Traditional ROI: 3.58%
33187 Muscadelle Ct Winchester, CA Welcome to 33187 Muscadelle Court in Winchester! This stunning single-story home, built in...	4 beds \| 4 baths \| 2,641 sq.ft.	$825,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 3.5% Airbnb Rental Income: $1622 Traditional Rental Income: $4508 Airbnb ROI: -0.85% Traditional ROI: 3.5%
31579 Mccartney Drive 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.	$624,888	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.61% Airbnb Rental Income: $2276 Traditional Rental Income: $3277 Airbnb ROI: 0.92% Traditional ROI: 3.61%
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%
31250 Loretta Ave. Winchester, CA Welcome to your ideal blend of comfort and equestrian lifestyle in Winchester. Built in 20...	3 beds \| 2 baths \| 1,701 sq.ft.	$945,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.09% Airbnb Rental Income: $2276 Traditional Rental Income: $3315 Airbnb ROI: 0.26% Traditional ROI: 2.09%
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.	$799,999	Airbnb cash on cash: -1.09% Traditional cash on cash: 4.53% Airbnb Rental Income: $1622 Traditional Rental Income: $5352 Airbnb ROI: -1.09% Traditional ROI: 4.53%
30765 Expedition Winchester, CA This luxurious, like-new home is packed with upgrades and ready for you to move in! Highl...	3 beds \| 2 baths \| 2,042 sq.ft.	$598,888	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.35% Airbnb Rental Income: $2276 Traditional Rental Income: $3465 Airbnb ROI: 0.2% Traditional ROI: 3.35%
29571 Grizzly Winchester, CA Shows like a Model Home and thoughtfully upgraded throughout, itâs a must-see. Inside, y...	3 beds \| 2 baths \| 1,882 sq.ft.	$539,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 5.77% Airbnb Rental Income: $2276 Traditional Rental Income: $4015 Airbnb ROI: 1.19% Traditional ROI: 5.77%
36415 Flare Dr Winchester, CA Award-winning Temecula School district /Paid-off Solar/downstairs bedroom/Energy-efficient...	4 beds \| 3 baths \| 1,861 sq.ft.	$619,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 3.24% Airbnb Rental Income: $1622 Traditional Rental Income: $3475 Airbnb ROI: -0.76% Traditional ROI: 3.24%
31352 Osage Trail Court Winchester, CA Discover this inspired Lexis home. Included features: a charming covered entry; an invitin...	4 beds \| 2 baths \| 2,307 sq.ft.	$611,326	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.77% Airbnb Rental Income: $1622 Traditional Rental Income: $3402 Airbnb ROI: -0.15% Traditional ROI: 3.77%
31365 Osage Trail Court Winchester, CA The main floor of this eye-catching Lander home offers a spacious great room and an open d...	3 beds \| 2 baths \| 2,201 sq.ft.	$602,990	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.87% Airbnb Rental Income: $2276 Traditional Rental Income: $3415 Airbnb ROI: 0.84% Traditional ROI: 3.87%
31339 Siskiyou Pass Court Winchester, CA A charming covered entry welcomes guests to the handsome Logan plan. Pass a study and powd...	4 beds \| 2 baths \| 2,402 sq.ft.	$621,347	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.7% Airbnb Rental Income: $1622 Traditional Rental Income: $3410 Airbnb ROI: -0.18% Traditional ROI: 3.7%
29554 Aramina Ct Winchester, CA Beautiful 4BD/3BA Home in Gated Winchester Community â Built in 2023! This modern, mov...	4 beds \| 3 baths \| 2,193 sq.ft.	$564,990	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.65% Airbnb Rental Income: $1622 Traditional Rental Income: $3545 Airbnb ROI: -0.86% Traditional ROI: 3.65%

Real Estate investment in Winchester, CA

There are 165 properties for sale in the city of Winchester . The median list price in Winchester is $619,800 and the average price per square foot is $295. In January 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,427.

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

There are 165 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%

29046 Delores Lane

Winchester, CA

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

$535,000

Airbnb cash on cash: 2.07%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $2276

Traditional Rental Income: $3185

Airbnb ROI: 2.07%

Traditional ROI: 5.02%

29460 Bamboo Court

Winchester, CA

3 beds | 2 baths | 1,868 sq.ft.

$580,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2276

Traditional Rental Income: $2912

Airbnb ROI: 1.23%

Traditional ROI: 3.45%

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.

$749,999

Airbnb cash on cash: -0.36%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1622

Traditional Rental Income: $3711

Airbnb ROI: -0.36%

Traditional ROI: 3.29%

33143 Big Range Drive

Winchester, CA

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

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

$510,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $2276

Traditional Rental Income: $2852

Airbnb ROI: 1.36%