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
31832 Granville Dr Winchester, CA	3 beds \| 2 baths \| 1,509 sq.ft.	$585,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 4.34% Airbnb Rental Income: $2276 Traditional Rental Income: $3294 Airbnb ROI: 1.44% Traditional ROI: 4.34%
29341 Wyatt Earp Way Winchester, CA	4 beds \| 3 baths \| 2,203 sq.ft.	$615,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 5.1% Airbnb Rental Income: $1622 Traditional Rental Income: $3643 Airbnb ROI: 0.78% Traditional ROI: 5.1%
35342 Marabella Ct Winchester, CA	3 beds \| 2 baths \| 1,925 sq.ft.	$569,999	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.98% Airbnb Rental Income: $2276 Traditional Rental Income: $3016 Airbnb ROI: 1.53% Traditional ROI: 3.98%
35473 Marabella Ct Winchester, CA Welcome to this beautifully upgraded 3-bedroom, 2.5-bath home located within the gated com...	3 beds \| 2 baths \| 1,775 sq.ft.	$530,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.67% Airbnb Rental Income: $2276 Traditional Rental Income: $3649 Airbnb ROI: 0.75% Traditional ROI: 4.67%
30753 Alister Lane Winchester, CA	5 beds \| 3 baths \| 2,534 sq.ft.	$649,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.95% Airbnb Rental Income: $1983 Traditional Rental Income: $3549 Airbnb ROI: 0.51% Traditional ROI: 3.95%
29230 Hondo Ln Winchester, CA	3 beds \| 2 baths \| 1,919 sq.ft.	$595,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.86% Airbnb Rental Income: $2276 Traditional Rental Income: $3213 Airbnb ROI: 1.15% Traditional ROI: 3.86%
36462 Sweet Berry Ct Winchester, CA	5 beds \| 4 baths \| 3,912 sq.ft.	$749,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 3.55% Airbnb Rental Income: $1983 Traditional Rental Income: $4112 Airbnb ROI: -0.25% Traditional ROI: 3.55%
30402 Concord Coach Court Winchester, CA	5 beds \| 3 baths \| 2,540 sq.ft.	$779,990	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.96% Airbnb Rental Income: $1983 Traditional Rental Income: $4335 Airbnb ROI: 0.01% Traditional ROI: 3.96%
31324 Scrub Jay Rd. Winchester, CA	4 beds \| 3 baths \| 2,239 sq.ft.	$664,999	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.55% Airbnb Rental Income: $1622 Traditional Rental Income: $3613 Airbnb ROI: 0.6% Traditional ROI: 4.55%
29640 Barrel Court Winchester, CA	4 beds \| 3 baths \| 2,624 sq.ft.	$749,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.28% Airbnb Rental Income: $1622 Traditional Rental Income: $3382 Airbnb ROI: -0.9% Traditional ROI: 2.28%
28395 Matador Road Winchester, CA	3 beds \| 3 baths \| 1,567 sq.ft.	$557,900	Airbnb cash on cash: 1.09% Traditional cash on cash: 4.1% Airbnb Rental Income: $2276 Traditional Rental Income: $3276 Airbnb ROI: 1.09% Traditional ROI: 4.1%
29562 Winterstorm Court Winchester, CA	4 beds \| 3 baths \| 2,193 sq.ft.	$549,900	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%
29550 Woodcreek Trail Winchester, CA	4 beds \| 3 baths \| 2,722 sq.ft.	$630,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.58% Airbnb Rental Income: $1622 Traditional Rental Income: $3797 Airbnb ROI: -0.9% Traditional ROI: 3.58%
29554 Bisbee Court Winchester, CA	4 beds \| 3 baths \| 2,591 sq.ft.	$630,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.54% Airbnb Rental Income: $1622 Traditional Rental Income: $3619 Airbnb ROI: -0.64% Traditional ROI: 3.54%
32201 Rambling Court Winchester, CA	3 beds \| 3 baths \| 1,824 sq.ft.	$495,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.15% Airbnb Rental Income: $2276 Traditional Rental Income: $3498 Airbnb ROI: 0.29% Traditional ROI: 4.15%
31381 Linden Flower Road Winchester, CA	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%
32935-32935 9th Street Winchester, CA	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%
35160 Mahogany Glen Dr Winchester, CA	4 beds \| 3 baths \| 3,810 sq.ft.	$795,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.02% Airbnb Rental Income: $1622 Traditional Rental Income: $5427 Airbnb ROI: -0.74% Traditional ROI: 5.02%
31820 Gimbal Winchester, CA	3 beds \| 2 baths \| 1,677 sq.ft.	$585,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 3.12% Airbnb Rental Income: $2276 Traditional Rental Income: $3252 Airbnb ROI: 0.29% Traditional ROI: 3.12%
36562 Van Gaale Winchester, CA	4 beds \| 3 baths \| 2,813 sq.ft.	$1,250,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 1.94% Airbnb Rental Income: $1622 Traditional Rental Income: $4360 Airbnb ROI: -0.81% Traditional ROI: 1.94%
28110 Winchester Winchester, CA	3 beds \| 2 baths \| 1,450 sq.ft.	$460,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 5.45% Airbnb Rental Income: $2276 Traditional Rental Income: $2980 Airbnb ROI: 2.5% Traditional ROI: 5.45%
34936 Old Vine Winchester, CA	3 beds \| 2 baths \| 2,320 sq.ft.	$664,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.37% Airbnb Rental Income: $2276 Traditional Rental Income: $3864 Airbnb ROI: -0.11% Traditional ROI: 3.37%
31615 Leon Winchester, CA	4 beds \| 2 baths \| 1,954 sq.ft.	$810,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.17% Airbnb Rental Income: $1622 Traditional Rental Income: $3437 Airbnb ROI: 0.15% Traditional ROI: 3.17%
31672 Settlers Road Winchester, CA	3 beds \| 2 baths \| 1,569 sq.ft.	$624,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.47% Airbnb Rental Income: $2276 Traditional Rental Income: $3036 Airbnb ROI: 0.19% Traditional ROI: 2.47%
35604 Shadow Winchester, CA	4 beds \| 3 baths \| 2,995 sq.ft.	$739,800	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.31% Airbnb Rental Income: $1622 Traditional Rental Income: $3599 Airbnb ROI: -0.22% Traditional ROI: 3.31%
32810 Olive Winchester, CA	4 beds \| 2 baths \| 2,280 sq.ft.	$510,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 4.17% Airbnb Rental Income: $1622 Traditional Rental Income: $3119 Airbnb ROI: 0.07% Traditional ROI: 4.17%
31831 Ridge Berry Winchester, CA	3 beds \| 3 baths \| 2,356 sq.ft.	$725,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.13% Airbnb Rental Income: $2276 Traditional Rental Income: $3445 Airbnb ROI: 0.56% Traditional ROI: 3.13%
35069 Painted Rock Winchester, CA	5 beds \| 3 baths \| 3,001 sq.ft.	$699,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 3.71% Airbnb Rental Income: $1983 Traditional Rental Income: $3718 Airbnb ROI: 0.26% Traditional ROI: 3.71%
34495 Agave #23106 Winchester, CA	3 beds \| 2 baths \| 1,484 sq.ft.	$448,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.63% Airbnb Rental Income: $2276 Traditional Rental Income: $3569 Airbnb ROI: 0.2% Traditional ROI: 4.63%
31935 Violet Dr Winchester, CA	4 beds \| 3 baths \| 2,995 sq.ft.	$730,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.75% Airbnb Rental Income: $1622 Traditional Rental Income: $4530 Airbnb ROI: -0.2% Traditional ROI: 4.75%
36761 Pebley Ct Winchester, CA	5 beds \| 3 baths \| 3,217 sq.ft.	$960,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.24% Airbnb Rental Income: $1983 Traditional Rental Income: $4882 Airbnb ROI: -0.58% Traditional ROI: 3.24%
32074 Bandelier Rd Winchester, CA	4 beds \| 3 baths \| 3,331 sq.ft.	$649,950	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.58% Airbnb Rental Income: $1622 Traditional Rental Income: $4212 Airbnb ROI: -0.45% Traditional ROI: 4.58%
30897 Alister Lane Winchester, CA	4 beds \| 2 baths \| 2,033 sq.ft.	$639,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.29% Airbnb Rental Income: $1622 Traditional Rental Income: $3245 Airbnb ROI: -0.2% Traditional ROI: 3.29%
32576 Crystal Cove Court Winchester, CA	4 beds \| 3 baths \| 2,368 sq.ft.	$579,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 3.7% Airbnb Rental Income: $1622 Traditional Rental Income: $3707 Airbnb ROI: -1.01% Traditional ROI: 3.7%
35554 Yellowstone Winchester, CA	4 beds \| 2 baths \| 2,712 sq.ft.	$703,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.94% Airbnb Rental Income: $1622 Traditional Rental Income: $3942 Airbnb ROI: -0.29% Traditional ROI: 3.94%
29741 Ryegrass Winchester, CA	4 beds \| 4 baths \| 2,705 sq.ft.	$745,500	Airbnb cash on cash: -1.06% Traditional cash on cash: 3.64% Airbnb Rental Income: $1622 Traditional Rental Income: $4428 Airbnb ROI: -1.06% Traditional ROI: 3.64%
32184 Rambling Court Winchester, CA	3 beds \| 3 baths \| 1,824 sq.ft.	$599,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.42% Airbnb Rental Income: $2276 Traditional Rental Income: $3569 Airbnb ROI: 0.09% Traditional ROI: 3.42%
32394 Orange Blossom Winchester, CA	4 beds \| 3 baths \| 2,500 sq.ft.	$800,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.33% Airbnb Rental Income: $1622 Traditional Rental Income: $4001 Airbnb ROI: -0.48% Traditional ROI: 3.33%
31070 Florence Ct Winchester, CA	4 beds \| 3 baths \| 2,644 sq.ft.	$775,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.43% Airbnb Rental Income: $1622 Traditional Rental Income: $4254 Airbnb ROI: 0.15% Traditional ROI: 4.43%
30608 Expedition Winchester, CA	5 beds \| 3 baths \| 2,540 sq.ft.	$689,500	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.73% Airbnb Rental Income: $1983 Traditional Rental Income: $3728 Airbnb ROI: 0.21% Traditional ROI: 3.73%

Real Estate investment in Winchester, CA

There are 110 properties for sale in the city of Winchester . The median list price in Winchester is $640,617 and the average price per square foot is $266. In July 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,394.

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

There are 110 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

31832 Granville Dr

Winchester, CA

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

$585,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $2276

Traditional Rental Income: $3294

Airbnb ROI: 1.44%

Traditional ROI: 4.34%

29341 Wyatt Earp Way

Winchester, CA

4 beds | 3 baths | 2,203 sq.ft.

$615,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $1622

Traditional Rental Income: $3643

Airbnb ROI: 0.78%

Traditional ROI: 5.1%

35342 Marabella Ct

Winchester, CA

3 beds | 2 baths | 1,925 sq.ft.

$569,999

Airbnb cash on cash: 1.53%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $2276

Traditional Rental Income: $3016

Airbnb ROI: 1.53%

Traditional ROI: 3.98%

35473 Marabella Ct

Winchester, CA

3 beds | 2 baths | 1,775 sq.ft.

$530,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $2276

Traditional Rental Income: $3649

Airbnb ROI: 0.75%

Traditional ROI: 4.67%

30753 Alister Lane

Winchester, CA

5 beds | 3 baths | 2,534 sq.ft.

$649,000

Airbnb cash on cash: 0.51%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1983

Traditional Rental Income: $3549

Airbnb ROI: 0.51%

Traditional ROI: 3.95%

29230 Hondo Ln

Winchester, CA

3 beds | 2 baths | 1,919 sq.ft.

$595,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $2276

Traditional Rental Income: $3213

Airbnb ROI: 1.15%

Traditional ROI: 3.86%

36462 Sweet Berry Ct

Winchester, CA

5 beds | 4 baths | 3,912 sq.ft.

$749,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1983

Traditional Rental Income: $4112

Airbnb ROI: -0.25%

Traditional ROI: 3.55%

30402 Concord Coach Court

Winchester, CA

5 beds | 3 baths | 2,540 sq.ft.

$779,990

Airbnb cash on cash: 0.01%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $1983

Traditional Rental Income: $4335

Airbnb ROI: 0.01%