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.	$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%
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%
32764 Lambeth Street Winchester, CA Welcome to this stunning two-story home located on a desirable corner lot in Winchester. W...	4 beds \| 3 baths \| 3,119 sq.ft.	$850,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.62% Airbnb Rental Income: $1622 Traditional Rental Income: $3474 Airbnb ROI: -1.3% Traditional ROI: 1.62%
29388 Opal Skye Way Winchester, CA Don't miss out on this last chance to secure a home with Plan 6 at Opal Skye! Take full ad...	3 beds \| 2 baths \| 2,054 sq.ft.	$569,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 4.41% Airbnb Rental Income: $2276 Traditional Rental Income: $3545 Airbnb ROI: 0.96% Traditional ROI: 4.41%
30765 Expedition Drive Winchester, CA Back on the market! Welcome home to prestigious Winchester Ridge development. This luxurio...	3 beds \| 2 baths \| 2,042 sq.ft.	$608,888	Airbnb cash on cash: 0.92% Traditional cash on cash: 4.14% Airbnb Rental Income: $2276 Traditional Rental Income: $3534 Airbnb ROI: 0.92% Traditional ROI: 4.14%
29339 Opal Skye Way Winchester, CA This stunning Former Model Homeboasts an open floorplan, 3 bedrooms with a loft and 2.5 ba...	3 beds \| 2 baths \| 1,882 sq.ft.	$549,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.72% Airbnb Rental Income: $2276 Traditional Rental Income: $3087 Airbnb ROI: 1.03% Traditional ROI: 3.72%
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%
29068 Aubrey Circle Winchester, CA Welcome to this beautifully maintained 3-bedroom, 2 bath home with a flexible floorpan tha...	3 beds \| 2 baths \| 1,857 sq.ft.	$598,999	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.49% Airbnb Rental Income: $2276 Traditional Rental Income: $3265 Airbnb ROI: 0.7% Traditional ROI: 3.49%
32529 Presidio Hills Lane Winchester, CA Welcome to 32529 Presidio Hills Lane, a stunning home with over $100K in upgrades in Morni...	4 beds \| 2 baths \| 2,909 sq.ft.	$835,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.75% Airbnb Rental Income: $1622 Traditional Rental Income: $4050 Airbnb ROI: -0.96% Traditional ROI: 2.75%
32133 Kale Lane Winchester, CA Get ready for summer in this stunning pool home featuring a heated saltwater pool and spaâ...	4 beds \| 2 baths \| 2,184 sq.ft.	$650,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.55% Airbnb Rental Income: $1622 Traditional Rental Income: $3318 Airbnb ROI: -0.01% Traditional ROI: 3.55%
33045 Chiffon Lane Winchester, CA Priced improvement on this almost new home. Actually, it's BETTER than NEW! And has PAID S...	4 beds \| 3 baths \| 2,429 sq.ft.	$679,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.47% Airbnb Rental Income: $1622 Traditional Rental Income: $3548 Airbnb ROI: -0.29% Traditional ROI: 3.47%
31759 Delfina Way Winchester, CA Welcome to this beautifully maintained 4-bedroom, 3-bathroom condo in the sought-after Cas...	4 beds \| 2 baths \| 2,016 sq.ft.	$499,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 4.66% Airbnb Rental Income: $1622 Traditional Rental Income: $3539 Airbnb ROI: -0.42% Traditional ROI: 4.66%
31556 Umbria Ln. Winchester, CA An Exceptional Residence in Winchester Welcome to a home where comfort, and modern living...	4 beds \| 3 baths \| 2,492 sq.ft.	$667,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.49% Airbnb Rental Income: $1622 Traditional Rental Income: $3530 Airbnb ROI: -0.32% Traditional ROI: 3.49%
30527 Expedition Drive Winchester, CA ASSUMABLE 4.5% LOAN \| $5,000 SELLER CREDIT \| PAID-OFF SOLAR \| 0.35-ACRE LOT \| NEXT-GEN CAS...	4 beds \| 3 baths \| 2,428 sq.ft.	$699,889	Airbnb cash on cash: -0.96% Traditional cash on cash: 4.01% Airbnb Rental Income: $1622 Traditional Rental Income: $4405 Airbnb ROI: -0.96% Traditional ROI: 4.01%
30853 Pony Express Drive Winchester, CA Welcome to this beautiful home located in the desirable community of Winchester, CA! This ...	4 beds \| 3 baths \| 2,227 sq.ft.	$614,500	Airbnb cash on cash: -0.83% Traditional cash on cash: 3.35% Airbnb Rental Income: $1622 Traditional Rental Income: $3561 Airbnb ROI: -0.83% Traditional ROI: 3.35%
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%
29562 Winterstorm Court Winchester, CA Better Than New & Never Lived In! This beautifully upgraded Opal-Skye 4-bedroom, 3-bath ho...	4 beds \| 3 baths \| 2,193 sq.ft.	$590,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 4.24% Airbnb Rental Income: $1622 Traditional Rental Income: $3515 Airbnb ROI: -0.03% Traditional ROI: 4.24%
30666 Corte Avila Winchester, CA NEW CONSTRUCTION and QUICK MOVE-IN in WINCHESTER - NO HOA and SOLAR INCLUDED!! This 1,890...	4 beds \| 3 baths \| 1,890 sq.ft.	$639,990	Airbnb cash on cash: 0.04% Traditional cash on cash: 4.12% Airbnb Rental Income: $1622 Traditional Rental Income: $3604 Airbnb ROI: 0.04% Traditional ROI: 4.12%
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.	$619,990	Airbnb cash on cash: 0.09% Traditional cash on cash: 4.36% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.09% Traditional ROI: 4.36%
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.	$604,990	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.15% Airbnb Rental Income: $2276 Traditional Rental Income: $3427 Airbnb ROI: 1.1% Traditional ROI: 4.15%
30643 Corte Avila Winchester, CA NEW CONSTRUCTION and QUICK MOVE-IN in WINCHESTER - NO HOA and SOLAR INCLUDED!! This 2,259-...	4 beds \| 3 baths \| 2,259 sq.ft.	$649,990	Airbnb cash on cash: 0.01% Traditional cash on cash: 4.32% Airbnb Rental Income: $1622 Traditional Rental Income: $3779 Airbnb ROI: 0.01% Traditional ROI: 4.32%
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%
35430 Azalea Circle Winchester, CA This Transitional style home lies in the middle of the quiet and peaceful neighborhood of ...	4 beds \| 3 baths \| 3,170 sq.ft.	$777,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.56% Airbnb Rental Income: $1622 Traditional Rental Income: $3955 Airbnb ROI: -0.29% Traditional ROI: 3.56%
35582 Laurel Tree Court Winchester, CA Price Improvement! An incredible opportunity to own a turnkey home in the highly desirable...	4 beds \| 3 baths \| 2,998 sq.ft.	$834,900	Airbnb cash on cash: -0.65% Traditional cash on cash: 3.33% Airbnb Rental Income: $1622 Traditional Rental Income: $4259 Airbnb ROI: -0.65% Traditional ROI: 3.33%
32144 Yosemite Street Winchester, CA Location, Privacy & Breathtaking ViewsâThis Home Has It All! Welcome to your dream retr...	4 beds \| 3 baths \| 2,771 sq.ft.	$1,049,900	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.43% Airbnb Rental Income: $1622 Traditional Rental Income: $4293 Airbnb ROI: -0.77% Traditional ROI: 2.43%
35414 Laurel Tree Court Winchester, CA Price Improvment! This is a wonderful home in the desirable Morningstar Ranch II communit...	4 beds \| 2 baths \| 2,560 sq.ft.	$709,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.18% Airbnb Rental Income: $1622 Traditional Rental Income: $3641 Airbnb ROI: -0.57% Traditional ROI: 3.18%
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%
32593 Cumulus Lane Winchester, CA Welcome to 32593 Cumulus Lane â a stunning, thoughtfully designed home with an open-conc...	4 beds \| 3 baths \| 2,239 sq.ft.	$649,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.43% Airbnb Rental Income: $1622 Traditional Rental Income: $3722 Airbnb ROI: -0.79% Traditional ROI: 3.43%
34495 Agave Drive #34101 Winchester, CA View home! Fast move in OK! VA APPROVED. Spacious Four-Bedroom Home in Desirable Sevilla C...	4 beds \| 2 baths \| 1,714 sq.ft.	$499,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 3.81% Airbnb Rental Income: $1622 Traditional Rental Income: $3314 Airbnb ROI: -0.8% Traditional ROI: 3.81%
32458 Daisy Drive Winchester, CA DRASTIC PRICE REDUCTION! One of the best values in the area! Donât miss this highly UP...	3 beds \| 2 baths \| 2,560 sq.ft.	$709,990	Airbnb cash on cash: 0.29% Traditional cash on cash: 3.05% Airbnb Rental Income: $2276 Traditional Rental Income: $3537 Airbnb ROI: 0.29% Traditional ROI: 3.05%
29604 Kyles Circle Winchester, CA Better than new, this amazing home is located in a desirable community. You enter this gor...	3 beds \| 2 baths \| 2,054 sq.ft.	$529,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.5% Airbnb Rental Income: $2276 Traditional Rental Income: $3257 Airbnb ROI: 1.37% Traditional ROI: 4.5%
32420 Apricot Tree Road Winchester, CA This beautiful Mediterranean-Spanish home features 4 bedrooms 3.5 bathrooms plus an offic...	4 beds \| 3 baths \| 3,362 sq.ft.	$799,999	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.01% Airbnb Rental Income: $1622 Traditional Rental Income: $3740 Airbnb ROI: -0.45% Traditional ROI: 3.01%
29271 Citrus Glen Drive Winchester, CA Beautiful designed single-story home located just off Domenigoni Parkway, offering quick a...	4 beds \| 3 baths \| 2,083 sq.ft.	$598,990	Airbnb cash on cash: 0.16% Traditional cash on cash: 4.18% Airbnb Rental Income: $1622 Traditional Rental Income: $3411 Airbnb ROI: 0.16% Traditional ROI: 4.18%
29343 Windy Willow Lane Winchester, CA Single-Story Home with Modern Upgrades Located just off Domenigoni Parkway with quick acce...	4 beds \| 3 baths \| 2,083 sq.ft.	$658,990	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.64% Airbnb Rental Income: $1622 Traditional Rental Income: $3409 Airbnb ROI: -0.01% Traditional ROI: 3.64%
32181 Kale Lane Winchester, CA Just Reduced! Beautiful Single Story Home with No Hoa, Low Taxes and Temecula Schools!! Th...	3 beds \| 2 baths \| 1,690 sq.ft.	$599,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.8% Airbnb Rental Income: $2276 Traditional Rental Income: $3138 Airbnb ROI: 1.24% Traditional ROI: 3.8%
31851 Pepper Tree Street Winchester, CA Welcome to this beautiful 3 bedroom + an office / 3 bathroom single story pool home with R...	4 beds \| 3 baths \| 2,774 sq.ft.	$825,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.23% Airbnb Rental Income: $1622 Traditional Rental Income: $3938 Airbnb ROI: -0.38% Traditional ROI: 3.23%
31809 Delfina Way Winchester, CA Step into this meticulously maintained, light-filled 2-bed, 2-bath condo nestled in the se...	2 beds \| 2 baths \| 1,056 sq.ft.	$412,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 4.24% Airbnb Rental Income: $1528 Traditional Rental Income: $2764 Airbnb ROI: -0.11% Traditional ROI: 4.24%
31844 Gimbal Way Winchester, CA Welcome to your next home in the heart of Winchester! This beautifully maintained 3-bedroo...	3 beds \| 2 baths \| 1,677 sq.ft.	$579,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.38% Airbnb Rental Income: $2276 Traditional Rental Income: $2951 Airbnb ROI: 1.08% Traditional ROI: 3.38%
29045 Silver Stirrup Way Winchester, CA This beautifully maintained single-story residence offers the perfect blend of comfort, st...	4 beds \| 2 baths \| 2,033 sq.ft.	$599,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 3.02% Airbnb Rental Income: $1622 Traditional Rental Income: $3246 Airbnb ROI: -0.7% Traditional ROI: 3.02%
28332 Fressia Drive Winchester, CA PRICE IMPROVEMENT!! Over $100K in upgrades including RV PARKING, GOLF PUTTING GREEN and SP...	4 beds \| 3 baths \| 1,896 sq.ft.	$615,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.99% Airbnb Rental Income: $1622 Traditional Rental Income: $3389 Airbnb ROI: 0.11% Traditional ROI: 3.99%

Real Estate investment in Winchester, CA

There are 182 properties for sale in the city of Winchester . The median list price in Winchester is $599,000 and the average price per square foot is $292. In September 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,411.

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

There are 182 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 $1,622.

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.

$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%

32198 Rambling Court

Winchester, CA

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%

32764 Lambeth Street

Winchester, CA

4 beds | 3 baths | 3,119 sq.ft.

$850,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1622

Traditional Rental Income: $3474

Airbnb ROI: -1.3%

Traditional ROI: 1.62%

29388 Opal Skye Way

Winchester, CA

3 beds | 2 baths | 2,054 sq.ft.

$569,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2276

Traditional Rental Income: $3545

Airbnb ROI: 0.96%

Traditional ROI: 4.41%

30765 Expedition Drive

Winchester, CA

3 beds | 2 baths | 2,042 sq.ft.

$608,888

Airbnb cash on cash: 0.92%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $2276

Traditional Rental Income: $3534

Airbnb ROI: 0.92%

Traditional ROI: 4.14%

29339 Opal Skye Way

Winchester, CA

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

$549,000

Airbnb cash on cash: 1.03%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $2276

Traditional Rental Income: $3087

Airbnb ROI: 1.03%

Traditional ROI: 3.72%

34936 Old Vine Road

Winchester, CA

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%

29068 Aubrey Circle

Winchester, CA

3 beds | 2 baths | 1,857 sq.ft.

$598,999

Airbnb cash on cash: 0.7%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $2276

Traditional Rental Income: $3265

Airbnb ROI: 0.7%