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
30750 Gazing Star Lane Winchester, CA Built in 2020 and located in Spencer's Crossing, 30750 Gazing Star Lane offers modern comf...	5 beds \| 3 baths \| 3,046 sq.ft.	$725,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.27% Airbnb Rental Income: $1983 Traditional Rental Income: $4278 Airbnb ROI: 0.11% Traditional ROI: 4.27%
31832 Granville Drive Winchester, CA Great single-story home in the French Valley area. This home offers 3 bedroom, 2 bathrooms...	3 beds \| 2 baths \| 1,509 sq.ft.	$586,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 4.33% Airbnb Rental Income: $2276 Traditional Rental Income: $3294 Airbnb ROI: 1.44% Traditional ROI: 4.33%
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.	$968,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 0.62% Airbnb Rental Income: $2276 Traditional Rental Income: $1714 Airbnb ROI: 0.65% Traditional ROI: 0.62%
29460 Bamboo Court Winchester, CA Your Dream Home AwaitsâMountain Views, Modern Comfort, and a Warm Welcome from the Momen...	3 beds \| 3 baths \| 1,868 sq.ft.	$578,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.47% Airbnb Rental Income: $2276 Traditional Rental Income: $2912 Airbnb ROI: 1.24% Traditional ROI: 3.47%
31082 Branches Circle Winchester, CA Welcome to the former MODEL HOMEâwhere luxury, design, and upgrades are taken to the nex...	3 beds \| 2 baths \| 2,293 sq.ft.	$715,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.39% Airbnb Rental Income: $2276 Traditional Rental Income: $3560 Airbnb ROI: 0.61% Traditional ROI: 3.39%
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%
31923 Corte De Pinos Winchester, CA Pool home â¢ Main-level primary suite â¢ 3-car garage Located on a cul-de-sac, this 4...	4 beds \| 4 baths \| 2,822 sq.ft.	$775,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.07% Airbnb Rental Income: $1622 Traditional Rental Income: $3434 Airbnb ROI: -0.08% Traditional ROI: 3.07%
35028 Orchard Crest Court Winchester, CA Welcome to this beautifully UPGRADED 5-bedroom home with over 3,000 sqft of living space, ...	5 beds \| 3 baths \| 2,998 sq.ft.	$799,999	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.89% Airbnb Rental Income: $1983 Traditional Rental Income: $3778 Airbnb ROI: -0.22% Traditional ROI: 2.89%
26812 Rodeo Court Winchester, CA Welcome to 26812 Rodeo Ct, located in the desirable Winchester Trails community! This beau...	4 beds \| 1 baths \| 2,315 sq.ft.	$585,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.81% Airbnb Rental Income: $1622 Traditional Rental Income: $2640 Airbnb ROI: 0.11% Traditional ROI: 2.81%
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%
31659 Poppy Street Winchester, CA Beautifully renovated in 2024, this expansive 4BR/3BA home offers approximately 3,037 sq f...	4 beds \| 3 baths \| 3,037 sq.ft.	$770,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.1% Airbnb Rental Income: $1622 Traditional Rental Income: $3604 Airbnb ROI: -0.3% Traditional ROI: 3.1%
31324 Scrub Jay Rd. Winchester, CA Welcome to this beautifully built 2024 home in the rapidly growing community of Winchester...	4 beds \| 3 baths \| 2,239 sq.ft.	$649,999	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.68% Airbnb Rental Income: $1622 Traditional Rental Income: $3613 Airbnb ROI: 0.64% Traditional ROI: 4.68%
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%
31214 Linden Flower Road Winchester, CA Welcome to this turnkey 4-bedroom home with an in-law suite, located in the beautiful and ...	4 beds \| 3 baths \| 2,612 sq.ft.	$708,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 2.94% Airbnb Rental Income: $1622 Traditional Rental Income: $3773 Airbnb ROI: -1.01% Traditional ROI: 2.94%
28395 Matador Road Winchester, CA Welcome to Paradera Place community of Winchester! An opportunity to own a New Constructio...	3 beds \| 2 baths \| 1,567 sq.ft.	$559,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.08% Airbnb Rental Income: $2276 Traditional Rental Income: $3276 Airbnb ROI: 1.08% Traditional ROI: 4.08%
33134 Celadon Avenue Winchester, CA Step into a lifestyle of effortless elegance and turnkey sophistication. This 2025-built s...	3 beds \| 2 baths \| 2,021 sq.ft.	$689,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.03% Airbnb Rental Income: $2276 Traditional Rental Income: $3307 Airbnb ROI: 0.54% Traditional ROI: 3.03%
31961 Honeysuckle Circle Winchester, CA NO HOA! Paid-off Solar! This home is immaculate with beautiful tile flooring and granite c...	4 beds \| 3 baths \| 2,877 sq.ft.	$690,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.82% Airbnb Rental Income: $1622 Traditional Rental Income: $3874 Airbnb ROI: -0.39% Traditional ROI: 3.82%
29562 Winterstorm Court Winchester, CA PAID OFF SOLAR Welcome to this stunning 2023-built residence located in a premier, gro...	4 beds \| 3 baths \| 2,193 sq.ft.	$549,999	Airbnb cash on cash: 0.04% Traditional cash on cash: 4.62% Airbnb Rental Income: $1622 Traditional Rental Income: $3515 Airbnb ROI: 0.04% Traditional ROI: 4.62%
34495 Agave Drive #34103 Winchester, CA Sevilla View Home! VA Approved! This never-lived-in townhome features luxurious upgraded f...	3 beds \| 2 baths \| 1,408 sq.ft.	$474,950	Airbnb cash on cash: 0.35% Traditional cash on cash: 3.74% Airbnb Rental Income: $2276 Traditional Rental Income: $3215 Airbnb ROI: 0.35% Traditional ROI: 3.74%
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.	$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%
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.	$699,999	Airbnb cash on cash: -1.04% Traditional cash on cash: 3.17% Airbnb Rental Income: $1622 Traditional Rental Income: $3912 Airbnb ROI: -1.04% Traditional ROI: 3.17%
31381 Linden Flower Road Winchester, CA The floorplan is ideal for multi generational families, house sharing or just room for eve...	5 beds \| 3 baths \| 2,540 sq.ft.	$680,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 3.45% Airbnb Rental Income: $1983 Traditional Rental Income: $3909 Airbnb ROI: -0.41% Traditional ROI: 3.45%
32935 9th Street 32935 Winchester, CA Discover a rare multi-use ranch property in the heart of Old Town Winchester, offering the...	2 beds \| 2 baths \| 1,248 sq.ft.	$749,990	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.63% Airbnb Rental Income: $1528 Traditional Rental Income: $2900 Airbnb ROI: 0.03% Traditional ROI: 2.63%
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.	$616,326	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.73% Airbnb Rental Income: $1622 Traditional Rental Income: $3402 Airbnb ROI: -0.17% Traditional ROI: 3.73%
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.	$607,990	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.82% Airbnb Rental Income: $2276 Traditional Rental Income: $3415 Airbnb ROI: 0.82% Traditional ROI: 3.82%
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.	$626,347	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.65% Airbnb Rental Income: $1622 Traditional Rental Income: $3410 Airbnb ROI: -0.19% Traditional ROI: 3.65%
28625 Shady Tree Winchester, CA Subject to cancellation of current listing Entirely renovated ranch-style home on 1.25 ACR...	4 beds \| 2 baths \| 2,707 sq.ft.	$879,999	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.7% Airbnb Rental Income: $1622 Traditional Rental Income: $4151 Airbnb ROI: 0.06% Traditional ROI: 3.7%
31820 Gimbal Winchester, CA Better than New opportunity to own this highly sought after home in the Tierra Del Sol com...	3 beds \| 3 baths \| 1,677 sq.ft.	$585,999	Airbnb cash on cash: 0.29% Traditional cash on cash: 3.11% Airbnb Rental Income: $2276 Traditional Rental Income: $3252 Airbnb ROI: 0.29% Traditional ROI: 3.11%
31679 Palo Verde Court Winchester, CA Welcome to your dream single-story pool home nestled in a peaceful cul-de-sac in one of Wi...	3 beds \| 4 baths \| 2,402 sq.ft.	$715,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 4.17% Airbnb Rental Income: $2276 Traditional Rental Income: $3927 Airbnb ROI: 0.84% Traditional ROI: 4.17%
29689 Crockett Court Winchester, CA Experience the ideal combination of comfort and modern style in Alder Plan 1 at Luminary. ...	3 beds \| 2 baths \| 1,569 sq.ft.	$569,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 4.45% Airbnb Rental Income: $2276 Traditional Rental Income: $3113 Airbnb ROI: 1.8% Traditional ROI: 4.45%
36562 Van Gaale Winchester, CA The Sunset Ranch on Benton prevents ample opportunities. Currently zoned for a single-fami...	4 beds \| 3 baths \| 2,813 sq.ft.	$1,650,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.23% Airbnb Rental Income: $1622 Traditional Rental Income: $4360 Airbnb ROI: -0.85% Traditional ROI: 1.23%
28110 Winchester Winchester, CA LOCATION, LOCATION, LOCATION, EXCELLENT OPPORTUNITY IN THE HEART OF WWINCHESTER FOR FIRST ...	3 beds \| 2 baths \| 1,450 sq.ft.	$475,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 5.25% Airbnb Rental Income: $2276 Traditional Rental Income: $2980 Airbnb ROI: 2.39% Traditional ROI: 5.25%
32764 Lambeth Winchester, CA 10,000+ sq ft lot with a pool and outdoor Kitchen! Paid Solar! And Next Gen suite! Beauti...	4 beds \| 3 baths \| 3,119 sq.ft.	$839,999	Airbnb cash on cash: -0.98% Traditional cash on cash: 2.3% Airbnb Rental Income: $1622 Traditional Rental Income: $3726 Airbnb ROI: -0.98% Traditional ROI: 2.3%
30681 Expedition Winchester, CA Stunning Turnkey home nestled in the heart of Winchester with beautiful Mountain Views! Bu...	3 beds \| 2 baths \| 2,042 sq.ft.	$599,999	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.95% Airbnb Rental Income: $2276 Traditional Rental Income: $3261 Airbnb ROI: 0.17% Traditional ROI: 2.95%
31372 Trappers Loop Winchester, CA Welcome to this lovely Lancaster home, ready for quick move-in. Included features: an invi...	3 beds \| 2 baths \| 1,795 sq.ft.	$577,990	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.88% Airbnb Rental Income: $2276 Traditional Rental Income: $3292 Airbnb ROI: 0.95% Traditional ROI: 3.88%
29205 Santa Fe Springs Court 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: 3.83% Airbnb Rental Income: $1622 Traditional Rental Income: $3300 Airbnb ROI: -0.08% Traditional ROI: 3.83%
31351 Siskiyou Court Winchester, CA Discover this inspired Lexis home. Included features: a charming covered entry; an invitin...	3 beds \| 2 baths \| 2,307 sq.ft.	$618,990	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.76% Airbnb Rental Income: $2276 Traditional Rental Income: $3437 Airbnb ROI: 0.77% Traditional ROI: 3.76%
31353 Osage Trail 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.	$584,990	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.97% Airbnb Rental Income: $1622 Traditional Rental Income: $3377 Airbnb ROI: -0.08% Traditional ROI: 3.97%
31341 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.	$613,990	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.74% Airbnb Rental Income: $2276 Traditional Rental Income: $3397 Airbnb ROI: 0.79% Traditional ROI: 3.74%
32619 Cottonwood Road Winchester, CA Spacious home in a desirable location featuring 3,107 square feet, 5 bedrooms, 3 bathrooms...	5 beds \| 3 baths \| 3,157 sq.ft.	$719,999	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.77% Airbnb Rental Income: $1983 Traditional Rental Income: $4034 Airbnb ROI: -0.06% Traditional ROI: 3.77%

Real Estate investment in Winchester, CA

There are 201 properties for sale in the city of Winchester . The median list price in Winchester is $609,990 and the average price per square foot is $288. In April 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,357.

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

There are 201 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

30750 Gazing Star Lane

Winchester, CA

5 beds | 3 baths | 3,046 sq.ft.

$725,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $1983

Traditional Rental Income: $4278

Airbnb ROI: 0.11%

Traditional ROI: 4.27%

31832 Granville Drive

Winchester, CA

3 beds | 2 baths | 1,509 sq.ft.

$586,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $2276

Traditional Rental Income: $3294

Airbnb ROI: 1.44%

Traditional ROI: 4.33%

33043 Wesley Street

Winchester, CA

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

$968,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $2276

Traditional Rental Income: $1714

Airbnb ROI: 0.65%

Traditional ROI: 0.62%

29460 Bamboo Court

Winchester, CA

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

$578,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $2276

Traditional Rental Income: $2912

Airbnb ROI: 1.24%

Traditional ROI: 3.47%

31082 Branches Circle

Winchester, CA

3 beds | 2 baths | 2,293 sq.ft.

$715,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $2276

Traditional Rental Income: $3560

Airbnb ROI: 0.61%

Traditional ROI: 3.39%

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%

31923 Corte De Pinos

Winchester, CA

4 beds | 4 baths | 2,822 sq.ft.

$775,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $1622

Traditional Rental Income: $3434

Airbnb ROI: -0.08%

Traditional ROI: 3.07%

35028 Orchard Crest Court

Winchester, CA

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

$799,999

Airbnb cash on cash: -0.22%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $1983

Traditional Rental Income: $3778

Airbnb ROI: -0.22%