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
30897 Rushing Water Street Winchester, CA Fairview at Creekstone is a beautiful resort-style community.This thoughtfully designed tw...	3 beds \| 2 baths \| 2,076 sq.ft.	$502,990	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.92% Airbnb Rental Income: $2373 Traditional Rental Income: $3038 Airbnb ROI: 1.26% Traditional ROI: 3.92%
30873 Rushing Water Street Winchester, CA Fairview at Creekstone is a beautiful resort-style community.This thoughtfully designed tw...	3 beds \| 2 baths \| 2,076 sq.ft.	$550,217	Airbnb cash on cash: 1.01% Traditional cash on cash: 4.2% Airbnb Rental Income: $2373 Traditional Rental Income: $3428 Airbnb ROI: 1.01% Traditional ROI: 4.2%
34253 Aspen Alley Winchester, CA Beautiful Bordeaux community 2-story home in French Valley. Close to award winning schools...	3 beds \| 2 baths \| 2,198 sq.ft.	$680,990	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.38% Airbnb Rental Income: $2373 Traditional Rental Income: $3354 Airbnb ROI: 0.92% Traditional ROI: 3.38%
34257 Cherrystone Way Winchester, CA Beautiful Bordeaux community 2-story home in French Valley. Close to award winning schools...	4 beds \| 3 baths \| 2,198 sq.ft.	$695,990	Airbnb cash on cash: 2.56% Traditional cash on cash: 3.64% Airbnb Rental Income: $3701 Traditional Rental Income: $3595 Airbnb ROI: 2.56% Traditional ROI: 3.64%
34259 Aspen Alley Winchester, CA Beautiful single-story home in French Valley. Close to award winning schools, family frien...	3 beds \| 2 baths \| 1,882 sq.ft.	$664,990	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.21% Airbnb Rental Income: $2373 Traditional Rental Income: $3174 Airbnb ROI: 0.98% Traditional ROI: 3.21%
34254 Slough Road Winchester, CA Beautiful single-story home in French Valley. Close to award winning schools, family frien...	3 beds \| 2 baths \| 1,882 sq.ft.	$639,990	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.83% Airbnb Rental Income: $2373 Traditional Rental Income: $3427 Airbnb ROI: 1.08% Traditional ROI: 3.83%
35482 Calendula Circle Winchester, CA WOW! Beautiful Home with Plenty of Space and Endless Possibilities! Welcome to this wonder...	4 beds \| 3 baths \| 2,950 sq.ft.	$699,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.16% Airbnb Rental Income: $3701 Traditional Rental Income: $3969 Airbnb ROI: 2.51% Traditional ROI: 4.16%
32479 Spun Cotton Drive Winchester, CA Welcome to this beautifully refreshed single-story Winchester home offering 3 bedrooms, 2....	3 beds \| 2 baths \| 2,050 sq.ft.	$639,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.54% Airbnb Rental Income: $2373 Traditional Rental Income: $3332 Airbnb ROI: 0.96% Traditional ROI: 3.54%
32675 Asbury Street Winchester, CA 100% USDA RURAL LOAN FINANCING MAY BE POSSIBLE! There are TWO Master Suites in this Beaut...	3 beds \| 3 baths \| 1,799 sq.ft.	$599,999	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.73% Airbnb Rental Income: $2373 Traditional Rental Income: $3488 Airbnb ROI: 1.69% Traditional ROI: 4.73%
31565 Hamburg Circle Winchester, CA Welcome to this beautifully maintained and thoughtfully updated single-story Winchester ho...	4 beds \| 2 baths \| 1,704 sq.ft.	$569,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 4.81% Airbnb Rental Income: $3701 Traditional Rental Income: $3549 Airbnb ROI: 3.58% Traditional ROI: 4.81%
35612 Loggins Court Winchester, CA Welcome to 35612 Loggins Court, where space, style, and comfort come together in one of Wi...	4 beds \| 3 baths \| 2,786 sq.ft.	$650,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 4.31% Airbnb Rental Income: $3701 Traditional Rental Income: $3868 Airbnb ROI: 2.71% Traditional ROI: 4.31%
34592 Wintersweet Lane Winchester, CA BEST DEAL IN THE NEIGHBORHOOD! \| SHORT SALE OPPORTUNITY. Welcome to 34592 Wintersweet Lane...	4 beds \| 2 baths \| 2,024 sq.ft.	$559,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 3.99% Airbnb Rental Income: $3701 Traditional Rental Income: $3062 Airbnb ROI: 3.67% Traditional ROI: 3.99%
34829 Sweet Bells Dr Winchester, CA 2.875% ASSUMABLE VA LOAN! Welcome to 34829 Sweet Bells Drive! This inviting single-story h...	3 beds \| 2 baths \| 1,691 sq.ft.	$639,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.53% Airbnb Rental Income: $2373 Traditional Rental Income: $3282 Airbnb ROI: 1.03% Traditional ROI: 3.53%
31623 Granville Drive Winchester, CA Located in Winchester within the highly rated Temecula school district, this bright and be...	4 beds \| 2 baths \| 1,936 sq.ft.	$639,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 3.6% Airbnb Rental Income: $3701 Traditional Rental Income: $3323 Airbnb ROI: 2.88% Traditional ROI: 3.6%
36287 Tahoe Street Winchester, CA Welcome to this inviting French Valley residence where comfortable living meets an easy, c...	4 beds \| 2 baths \| 1,999 sq.ft.	$619,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 3.98% Airbnb Rental Income: $3701 Traditional Rental Income: $3427 Airbnb ROI: 3.06% Traditional ROI: 3.98%
33108 Toledo Bend Court Winchester, CA Beautifully maintained 2022-built home at the end of a quiet Winchester cul-de-sac, set on...	4 beds \| 3 baths \| 2,590 sq.ft.	$710,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 3.71% Airbnb Rental Income: $3701 Traditional Rental Income: $3713 Airbnb ROI: 2.48% Traditional ROI: 3.71%
33143 Big Range Drive Winchester, CA Back on market through no fault of the property. Seller withdrew the home from the market ...	4 beds \| 3 baths \| 2,273 sq.ft.	$579,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.81% Airbnb Rental Income: $3701 Traditional Rental Income: $3191 Airbnb ROI: 3.27% Traditional ROI: 3.81%
30780 Impala Court Winchester, CA FHA Assumable Mortgage Loan at 5.75% subject to lender approval. Beautifully Upgraded Winc...	4 beds \| 2 baths \| 1,774 sq.ft.	$555,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.87% Airbnb Rental Income: $3701 Traditional Rental Income: $3145 Airbnb ROI: 3.39% Traditional ROI: 3.87%
34782 Grotto Hills Drive Winchester, CA Welcome to 34782 Grotto Hills Drive in the highly sought after Whispering Heights communit...	4 beds \| 3 baths \| 3,212 sq.ft.	$778,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 2.72% Airbnb Rental Income: $3701 Traditional Rental Income: $3741 Airbnb ROI: 1.55% Traditional ROI: 2.72%
28395 Matador Road Winchester, CA * ASSUMABLE LOAN- 4.99% RATE* Welcome to Paradera Place community of Winchester! An op...	3 beds \| 2 baths \| 1,567 sq.ft.	$554,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.13% Airbnb Rental Income: $2373 Traditional Rental Income: $3276 Airbnb ROI: 1.26% Traditional ROI: 4.13%
32593 Cumulus Lane Winchester, CA Stop scrolling. This is the one. 32593 Cumulus Ln in Winchester, CA 92596 is not just a...	4 beds \| 3 baths \| 2,239 sq.ft.	$699,500	Airbnb cash on cash: 1.85% Traditional cash on cash: 3.12% Airbnb Rental Income: $3701 Traditional Rental Income: $3722 Airbnb ROI: 1.85% Traditional ROI: 3.12%
29554 Bisbee Court Winchester, CA Welcome to 29554 Bisbee Court a beautiful home tucked away in a quiet Winchester cul-de-sa...	4 beds \| 3 baths \| 2,591 sq.ft.	$630,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 3.54% Airbnb Rental Income: $3701 Traditional Rental Income: $3619 Airbnb ROI: 2.31% Traditional ROI: 3.54%
36562 Van Gaale Winchester, CA The Sunset Ranch sits on 4.36 acres and is currently zoned for a primary home and a Guest ...	4 beds \| 3 baths \| 2,813 sq.ft.	$1,000,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.67% Airbnb Rental Income: $3701 Traditional Rental Income: $4360 Airbnb ROI: 1.1% Traditional ROI: 2.67%
31384 Pine Oak Road Winchester, CA Check out KBhome's Hudson Community in Winchester, CA! 4-bedroom, 2-bath home, enjoy the ...	4 beds \| 2 baths \| 2,026 sq.ft.	$649,990	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.53% Airbnb Rental Income: $3701 Traditional Rental Income: $3297 Airbnb ROI: 2.87% Traditional ROI: 3.53%
31667 Cobalite Winchester, CA Welcome to this beautiful 2025-built home in Murrieta, ideally situated on a desirable cor...	4 beds \| 3 baths \| 1,856 sq.ft.	$574,999	Airbnb cash on cash: 2.05% Traditional cash on cash: 3.14% Airbnb Rental Income: $3701 Traditional Rental Income: $3477 Airbnb ROI: 2.05% Traditional ROI: 3.14%
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.	$590,990	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.78% Airbnb Rental Income: $3701 Traditional Rental Income: $3300 Airbnb ROI: 3.04% Traditional ROI: 3.78%
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.	$621,990	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.74% Airbnb Rental Income: $2373 Traditional Rental Income: $3437 Airbnb ROI: 0.9% Traditional ROI: 3.74%
31353 Osage Trail Winchester, CA The Logan home is a 4 Bed 2.5 Bath with downstairs office/den with so many nice features a...	4 beds \| 3 baths \| 2,402 sq.ft.	$634,347	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.53% Airbnb Rental Income: $3701 Traditional Rental Income: $3377 Airbnb ROI: 2.72% Traditional ROI: 3.53%
31341 Osage Trail Court Winchester, CA Your Sanctuary Awaits: Low-Maintenance Living at The Woods Whether you are recovering ...	3 beds \| 2 baths \| 2,201 sq.ft.	$616,990	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.71% Airbnb Rental Income: $2373 Traditional Rental Income: $3397 Airbnb ROI: 0.92% Traditional ROI: 3.71%
29658 Lewis Circle Winchester, CA The Torrey Plan 4 at Luminary showcases the very best in modern home design. This thoughtf...	4 beds \| 3 baths \| 2,216 sq.ft.	$599,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.91% Airbnb Rental Income: $3701 Traditional Rental Income: $3525 Airbnb ROI: 3.79% Traditional ROI: 4.91%
31935 Violet Drive Winchester, CA Back on the market with New Price! Welcome to this beautiful pool and spa home located Fr...	4 beds \| 3 baths \| 2,995 sq.ft.	$725,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 4.79% Airbnb Rental Income: $3701 Traditional Rental Income: $4530 Airbnb ROI: 2.37% Traditional ROI: 4.79%
30901 Mossy Brook Street Winchester, CA Beautiful Deerfield community Craftsman style 2 story home, single level living. Featuring...	3 beds \| 2 baths \| 1,510 sq.ft.	$439,990	Airbnb cash on cash: 1.29% Traditional cash on cash: 4.71% Airbnb Rental Income: $2373 Traditional Rental Income: $3197 Airbnb ROI: 1.29% Traditional ROI: 4.71%
30893 Mossy Brook Street Winchester, CA Welcome to this beautifully designed two-story Spanish style home offering 1760sq. ft of v...	4 beds \| 3 baths \| 1,760 sq.ft.	$477,454	Airbnb cash on cash: 3.53% Traditional cash on cash: 4.25% Airbnb Rental Income: $3701 Traditional Rental Income: $3216 Airbnb ROI: 3.53% Traditional ROI: 4.25%
31048 Ferguson Court Winchester, CA Get the extra space youâve been looking for at Carson at Leon Ridge in Winchester, a bra...	4 beds \| 3 baths \| 2,305 sq.ft.	$689,990	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.49% Airbnb Rental Income: $3701 Traditional Rental Income: $3577 Airbnb ROI: 2.43% Traditional ROI: 3.49%
29741 Ryegrass Winchester, CA HUGE price reduction! Beautifully maintained 4-bedroom, 3.5-bathroom home in Winchester fe...	4 beds \| 3 baths \| 2,705 sq.ft.	$745,500	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.64% Airbnb Rental Income: $3701 Traditional Rental Income: $4428 Airbnb ROI: 1.44% Traditional ROI: 3.64%
32564 Quiet Trail Winchester, CA REDUCED!! Check out this rare opportunity to own a turnkey 3,670 sq. ft. home featurin...	4 beds \| 4 baths \| 3,687 sq.ft.	$795,899	Airbnb cash on cash: 1.91% Traditional cash on cash: 4.68% Airbnb Rental Income: $3701 Traditional Rental Income: $4945 Airbnb ROI: 1.91% Traditional ROI: 4.68%
31385 lolite Drive Winchester, CA Incredible opportunity to own this better than new townhome in highly sought after Winches...	3 beds \| 2 baths \| 1,711 sq.ft.	$525,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.1% Airbnb Rental Income: $2373 Traditional Rental Income: $3365 Airbnb ROI: 0.88% Traditional ROI: 4.1%
32350 Iron Trail Winchester, CA Welcome to 32350 Iron Trail Road, a stunning newly built home located in the highly desira...	3 beds \| 2 baths \| 1,672 sq.ft.	$539,900	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.25% Airbnb Rental Income: $2373 Traditional Rental Income: $3231 Airbnb ROI: 0.39% Traditional ROI: 3.25%
30661 Albiflora Way Winchester, CA This new Acadia residence offers the opportunity to own a detached single-family home with...	3 beds \| 2 baths \| 2,033 sq.ft.	$609,990	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.41% Airbnb Rental Income: $2373 Traditional Rental Income: $3337 Airbnb ROI: 1.69% Traditional ROI: 4.41%
31202 Morgan Trail Winchester, CA Experience the ease of single-story living at Carson at Leon Ridge, a new home community i...	4 beds \| 3 baths \| 2,085 sq.ft.	$659,990	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.45% Airbnb Rental Income: $3701 Traditional Rental Income: $3410 Airbnb ROI: 2.62% Traditional ROI: 3.45%

Real Estate investment in Winchester, CA

There are 195 properties for sale in the city of Winchester . The median list price in Winchester is $666,655 and the average price per square foot is $322. In October 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,383.

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

There are 195 investment properties available for sale in Winchester.

In 2026, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $3,383.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CA

30897 Rushing Water Street

Winchester, CA

3 beds | 2 baths | 2,076 sq.ft.

$502,990

Airbnb cash on cash: 1.26%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $2373

Traditional Rental Income: $3038

Airbnb ROI: 1.26%

Traditional ROI: 3.92%

30873 Rushing Water Street

Winchester, CA

3 beds | 2 baths | 2,076 sq.ft.

$550,217

Airbnb cash on cash: 1.01%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $2373

Traditional Rental Income: $3428

Airbnb ROI: 1.01%

Traditional ROI: 4.2%

34253 Aspen Alley

Winchester, CA

3 beds | 2 baths | 2,198 sq.ft.

$680,990

Airbnb cash on cash: 0.92%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $2373

Traditional Rental Income: $3354

Airbnb ROI: 0.92%

Traditional ROI: 3.38%

34257 Cherrystone Way

Winchester, CA

4 beds | 3 baths | 2,198 sq.ft.

$695,990

Airbnb cash on cash: 2.56%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3701

Traditional Rental Income: $3595

Airbnb ROI: 2.56%

Traditional ROI: 3.64%

34259 Aspen Alley

Winchester, CA

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

$664,990

Airbnb cash on cash: 0.98%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $2373

Traditional Rental Income: $3174

Airbnb ROI: 0.98%

Traditional ROI: 3.21%

34254 Slough Road

Winchester, CA

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

$639,990

Airbnb cash on cash: 1.08%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $2373

Traditional Rental Income: $3427

Airbnb ROI: 1.08%

Traditional ROI: 3.83%

35482 Calendula Circle

Winchester, CA

4 beds | 3 baths | 2,950 sq.ft.

$699,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $3701

Traditional Rental Income: $3969

Airbnb ROI: 2.51%

Traditional ROI: 4.16%

32479 Spun Cotton Drive

Winchester, CA

3 beds | 2 baths | 2,050 sq.ft.

$639,900

Airbnb cash on cash: 0.96%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $2373

Traditional Rental Income: $3332

Airbnb ROI: 0.96%