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

separator

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%
35622 Denver Cir Winchester, CA Beautiful home in the heart of French Valley. Spacious 4 bedroom, 3 bath home within walki...	4 beds \| 3 baths \| 2,202 sq.ft.	$615,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.65% Airbnb Rental Income: $1622 Traditional Rental Income: $3223 Airbnb ROI: 0.07% Traditional ROI: 3.65%
34701 Portarosa St Winchester, CA Enjoy energy efficient California living in this top of the line single story home with dr...	4 beds \| 2 baths \| 1,945 sq.ft.	$650,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.9% Airbnb Rental Income: $1622 Traditional Rental Income: $3171 Airbnb ROI: -0.41% Traditional ROI: 2.9%
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%
34592 Wintersweet Ln Winchester, CA THIS IS A MUST-SEE HOME! This beautiful property features 3 Spacious Bedrooms PLUS an OFFI...	3 beds \| 3 baths \| 2,024 sq.ft.	$625,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.47% Airbnb Rental Income: $2276 Traditional Rental Income: $3062 Airbnb ROI: 1.15% Traditional ROI: 3.47%
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%
35392 Corte Los Flores Winchester, CA Gorgeous 4 bedroom, 2.5 bathroom, single story home on a large lot and situated on a cul-d...	4 beds \| 2 baths \| 2,081 sq.ft.	$745,500	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.81% Airbnb Rental Income: $1622 Traditional Rental Income: $3279 Airbnb ROI: -0.23% Traditional ROI: 2.81%
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%
36462 Sweet Berry Ct 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 St 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.	$775,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.07% Airbnb Rental Income: $1622 Traditional Rental Income: $3604 Airbnb ROI: -0.31% Traditional ROI: 3.07%
30551 Bel Air Court Winchester, CA Welcome to this nearly new, energy-efficient 4-bedroom, 2.5-bath home built in 2024 by DR ...	4 beds \| 2 baths \| 1,835 sq.ft.	$559,999	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.88% Airbnb Rental Income: $1622 Traditional Rental Income: $3152 Airbnb ROI: 0.07% Traditional ROI: 3.88%
32297 Wild West Court Winchester, CA Beautifully maintained single-story home offering the perfect blend of comfort, style, and...	4 beds \| 2 baths \| 2,033 sq.ft.	$594,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.84% Airbnb Rental Income: $1622 Traditional Rental Income: $3209 Airbnb ROI: -0.85% Traditional ROI: 2.84%
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%
32768 Westport Way Winchester, CA 32768 Westport Way in Winchester, CA, is a 2,647 sq. ft. single-family Solar home built in...	4 beds \| 2 baths \| 2,647 sq.ft.	$699,999	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.35% Airbnb Rental Income: $1622 Traditional Rental Income: $3465 Airbnb ROI: -0.18% Traditional ROI: 3.35%
34495 Agave Dr #34103 Winchester, CA Sevilla View Home! VA Approved! This never-lived-in townhome features luxurious upgraded f...	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.	$643,990	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.13% Airbnb Rental Income: $1622 Traditional Rental Income: $3631 Airbnb ROI: 0.03% Traditional ROI: 4.13%
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.	$599,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.2% Airbnb Rental Income: $2276 Traditional Rental Income: $3427 Airbnb ROI: 1.13% Traditional ROI: 4.2%
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.	$579,990	Airbnb cash on cash: 1.23% Traditional cash on cash: 4.23% Airbnb Rental Income: $2276 Traditional Rental Income: $3333 Airbnb ROI: 1.23% Traditional ROI: 4.23%
34495 Agave Dr #34107 Winchester, CA MODEl HOME! Welcome to this charming two-story townhome in the desirable Sevilla community...	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%
34495 Agave Dr #10110 Winchester, CA Stunning, Move-In Ready Townhome with Fully Paid Solar in Temeculaâs Top School District...	3 beds \| 2 baths \| 1,408 sq.ft.	$455,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.6% Airbnb Rental Income: $2276 Traditional Rental Income: $3163 Airbnb ROI: 0.18% Traditional ROI: 3.6%
32684 Salvia Cir 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%
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%
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.	$725,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 3.03% Airbnb Rental Income: $1622 Traditional Rental Income: $3912 Airbnb ROI: -1.04% Traditional ROI: 3.03%
31289 Pine Oak Road Winchester, CA Beautiful Hudson community- KBhome's newest Community in Winchester, CA with all electric,...	4 beds \| 3 baths \| 2,763 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.	$615,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.77% Airbnb Rental Income: $1622 Traditional Rental Income: $3772 Airbnb ROI: -0.78% Traditional ROI: 3.77%
32461 Marietta Winchester, CA Incredible opportunity to own this formal model home, and it qualifies for a $20,000 grant...	4 beds \| 2 baths \| 2,909 sq.ft.	$785,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 2.47% Airbnb Rental Income: $1622 Traditional Rental Income: $3562 Airbnb ROI: -0.81% Traditional ROI: 2.47%
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%
35160 Mahogany Glen Dr Winchester, CA "Where Elegance Meets Everyday Living"! Welcome to a beautiful 4 bedroom Estate in Winches...	4 beds \| 3 baths \| 3,810 sq.ft.	$800,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 4.98% Airbnb Rental Income: $1622 Traditional Rental Income: $5427 Airbnb ROI: -0.74% Traditional ROI: 4.98%
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%
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%
28625 Shady Tree Winchester, CA Entirely renovated ranch-style home on 1.25 ACRES OF FLAT, FULLY USABLE LAND in beautiful ...	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 STUNNING Tierra Del Sol COMMUNITY! LOW HOA, TOP RATED TEMECULA SCHOOL DISTRICTS! THIS HOME...	3 beds \| 2 baths \| 1,677 sq.ft.	$589,999	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.08% Airbnb Rental Income: $2276 Traditional Rental Income: $3252 Airbnb ROI: 0.28% Traditional ROI: 3.08%
36143 Tahoe St Winchester, CA Welcome to this bright and inviting single-story home featuring an open floor plan filled ...	3 beds \| 2 baths \| 2,122 sq.ft.	$610,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.51% Airbnb Rental Income: $2276 Traditional Rental Income: $3462 Airbnb ROI: 0.43% Traditional ROI: 3.51%
32051 Clear Springs Dr Winchester, CA Welcome to this beautifully maintained 4 bedroom, 3.5 bath home, located in the peaceful a...	4 beds \| 3 baths \| 2,946 sq.ft.	$719,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.06% Airbnb Rental Income: $1622 Traditional Rental Income: $3942 Airbnb ROI: -0.09% Traditional ROI: 4.06%
34609 Clementine St Winchester, CA What's Special: High Ceilings \| Loft \| East Facing Lot. New Construction â Ready Now! Bu...	4 beds \| 3 baths \| 2,421 sq.ft.	$703,320	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.34% Airbnb Rental Income: $1622 Traditional Rental Income: $3547 Airbnb ROI: -0.29% Traditional ROI: 3.34%
36562 Van Gaale Winchester, CA The Sunset Ranch on Benton provides ample opportunities. Currently zoned for a single-fami...	4 beds \| 3 baths \| 2,813 sq.ft.	$2,000,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.84% Airbnb Rental Income: $1622 Traditional Rental Income: $4360 Airbnb ROI: -0.88% Traditional ROI: 0.84%
34495 Agave #15107 Winchester, CA Welcome to this 3 bedroom, 2.5 bathroom home offering 1,674 square feet, located in the Se...	3 beds \| 2 baths \| 1,674 sq.ft.	$473,500	Airbnb cash on cash: 0.05% Traditional cash on cash: 3.99% Airbnb Rental Income: $2276 Traditional Rental Income: $3453 Airbnb ROI: 0.05% Traditional ROI: 3.99%
36616 Chantecler Winchester, CA If youâve been searching for a home that offers meaningful space, functional layout, and...	5 beds \| 3 baths \| 2,731 sq.ft.	$724,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.61% Airbnb Rental Income: $1983 Traditional Rental Income: $4057 Airbnb ROI: -0.22% Traditional ROI: 3.61%

Real Estate investment in Winchester, CA

There are 180 properties for sale in the city of Winchester . The median list price in Winchester is $625,000 and the average price per square foot is $275. In March 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,413.

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

There are 180 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%

35622 Denver Cir

Winchester, CA

4 beds | 3 baths | 2,202 sq.ft.

$615,900

Airbnb cash on cash: 0.07%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $1622

Traditional Rental Income: $3223

Airbnb ROI: 0.07%

Traditional ROI: 3.65%

34701 Portarosa St

Winchester, CA

4 beds | 2 baths | 1,945 sq.ft.

$650,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $1622

Traditional Rental Income: $3171

Airbnb ROI: -0.41%

Traditional ROI: 2.9%

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%

34592 Wintersweet Ln

Winchester, CA

3 beds | 3 baths | 2,024 sq.ft.

$625,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $2276

Traditional Rental Income: $3062

Airbnb ROI: 1.15%

Traditional ROI: 3.47%

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%

35392 Corte Los Flores

Winchester, CA

4 beds | 2 baths | 2,081 sq.ft.

$745,500

Airbnb cash on cash: -0.23%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $1622

Traditional Rental Income: $3279

Airbnb ROI: -0.23%

Traditional ROI: 2.81%

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%