Real Estate Investment Properties for Sale in Winchester, VA

Looking for investment property in Winchester, VA with high ROI ?

Explore a variety of short-term homes & houses in Winchester, VA. Invest wisely with VRBO & Winchester, VA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Winchester, VA

Search for Single Family Residential for Sale in Winchester, Virginia. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 26 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
608 GREEN Street Winchester, VA Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 full bath. Hardwo...	3 beds \| 1 baths \| 1,040 sq.ft.	$289,999	Airbnb cash on cash: 2.33% Traditional cash on cash: 4.37% Airbnb Rental Income: $1643 Traditional Rental Income: $1737 Airbnb ROI: 2.33% Traditional ROI: 4.37%
939 WOODLAND AVE Winchester, VA Motivated sellers, Price Reduced!!! Need your Own Space? or you're looking to Downsize or ...	2 beds \| 2 baths \| N/A	$279,900	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.95% Airbnb Rental Income: $1436 Traditional Rental Income: $1298 Airbnb ROI: 1.85% Traditional ROI: 2.95%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$494,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.32%
339 LANNY Drive Winchester, VA Right off of Amherst St. in sought after Whittier Acres, we are proud to present 339 Lanny...	3 beds \| 3 baths \| 2,444 sq.ft.	$515,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.57% Airbnb Rental Income: $1643 Traditional Rental Income: $2584 Airbnb ROI: 0.66% Traditional ROI: 3.57%
121 SWEETBRIAR Lane Winchester, VA "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors...	4 beds \| 3 baths \| 3,442 sq.ft.	$643,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.18% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 3.18%
22 HORIZON DR Winchester, VA No HOA! 1 LEVEL LIVING home - 3 BR / 2 BA offers spacious kitchen with granite counters, f...	3 beds \| 2 baths \| 2,092 sq.ft.	$700,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.17% Airbnb Rental Income: $1643 Traditional Rental Income: $2485 Airbnb ROI: 0.17% Traditional ROI: 2.17%
1049 LAUREL GROVE RD Winchester, VA Tucked away on a quiet cul-de-sac, this custom 3-bedroom, 3-bath home is sited on a privat...	3 beds \| 3 baths \| N/A	$767,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.85% Airbnb Rental Income: $1643 Traditional Rental Income: $2366 Airbnb ROI: 0.19% Traditional ROI: 1.85%
881 ADAMS RD Winchester, VA Back on the Market and fully Certified! Appraised over asking, All inspections completed (...	3 beds \| 2 baths \| N/A	$689,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.1% Airbnb Rental Income: $1643 Traditional Rental Income: $2286 Airbnb ROI: 0.38% Traditional ROI: 2.1%
164 BETHEL GRANGE Road Winchester, VA Beautiful brick ranch in a lovely, country rural setting with mountain views and only minu...	3 beds \| 2 baths \| 1,952 sq.ft.	$435,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.07% Airbnb Rental Income: $1643 Traditional Rental Income: $2287 Airbnb ROI: 1.35% Traditional ROI: 4.07%
421 SUPERIOR AVE Winchester, VA Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt drivew...	3 beds \| 2 baths \| 1,800 sq.ft.	$455,700	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.38% Airbnb Rental Income: $1643 Traditional Rental Income: $2192 Airbnb ROI: 1.01% Traditional ROI: 3.38%
128 RAVEN OAKS DR Winchester, VA Back on the market with no fault to the seller. This is your second chance to snatch this ...	4 beds \| 3 baths \| N/A	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $2484 Airbnb ROI: N/A Traditional ROI: 2.23%
120 ARMSTRONG Place Winchester, VA Your opportunity to live next to the Golf course/Winchester Country Club in Fairway Estate...	4 beds \| 3 baths \| 3,490 sq.ft.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.55% Airbnb Rental Income: $null Traditional Rental Income: $3161 Airbnb ROI: N/A Traditional ROI: 4.55%
2723 WINDWOOD DR Winchester, VA Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, presti...	3 beds \| 3 baths \| N/A	$549,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.04% Airbnb Rental Income: $1643 Traditional Rental Income: $2551 Airbnb ROI: 0.37% Traditional ROI: 3.04%
280 PLOW RUN Lane Winchester, VA Now available: a custom-built, one-level home situated on 3.02 peaceful acres. This proper...	3 beds \| 3 baths \| 2,348 sq.ft.	$668,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.88% Airbnb Rental Income: $1643 Traditional Rental Income: $2790 Airbnb ROI: 0.29% Traditional ROI: 2.88%
428 WESTSIDE STATION DR Winchester, VA Buyer credit $10,000 at settlement with ratified contract by Nov 3, 2025, Beautiful, state...	5 beds \| 4 baths \| N/A	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 3.29%
112 STAR FORT DR Winchester, VA Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a qu...	3 beds \| 2 baths \| N/A	$300,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 5.58% Airbnb Rental Income: $1643 Traditional Rental Income: $2062 Airbnb ROI: 2.45% Traditional ROI: 5.58%
461 IMPERIAL Street Winchester, VA Charming Rancher In Winchester, VA! Beautifully updated 4-bedroom, 2 full bath home offers...	4 beds \| 2 baths \| 2,450 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 5.27%
525 E CORK ST Winchester, VA Beautiful and affordable Gem in the middle of Winchester City. Private, fully fenced yard ...	2 beds \| 1 baths \| N/A	$305,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 3.24% Airbnb Rental Income: $1436 Traditional Rental Income: $1483 Airbnb ROI: 1.59% Traditional ROI: 3.24%
2294 FRONT ROYAL Winchester, VA 3 Beds \| 1 Bath \| Partially Finished Basement \| .60 Acres \| New Roof WELCOME HOME!!!! Char...	3 beds \| 1 baths \| 1,974 sq.ft.	$320,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 4.36% Airbnb Rental Income: $1643 Traditional Rental Income: $1838 Airbnb ROI: 2.18% Traditional ROI: 4.36%
852 BUTLER AVE Winchester, VA Nestled in a fantastic location near shopping, schools, and historic downtown Winchester, ...	3 beds \| 2 baths \| N/A	$279,900	Airbnb cash on cash: 2.64% Traditional cash on cash: 6.11% Airbnb Rental Income: $1643 Traditional Rental Income: $2095 Airbnb ROI: 2.64% Traditional ROI: 6.11%
534 Grouse Drive Winchester, VA Like new construction without the wait! Lovely 2024, ranch home with partially finished ba...	3 beds \| 3 baths \| 1,966 sq.ft.	$330,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 6.03% Airbnb Rental Income: $1643 Traditional Rental Income: $2532 Airbnb ROI: 1.67% Traditional ROI: 6.03%
113 WILLIAMSON RD Winchester, VA Charming All-Brick Ranch just minutes from in Prime Winchester Location. Beautifully main...	3 beds \| 2 baths \| N/A	$450,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.61% Airbnb Rental Income: $1643 Traditional Rental Income: $2179 Airbnb ROI: 1.24% Traditional ROI: 3.61%
1133 TOMAHAWK TRL TRL Winchester, VA Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers ...	3 beds \| 2 baths \| 876 sq.ft.	$439,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.14% Airbnb Rental Income: $1643 Traditional Rental Income: $1917 Airbnb ROI: 1.35% Traditional ROI: 3.14%
107 DALE CT Winchester, VA Welcome to Heritage Hills! Tucked away on a quiet, private cul-de-sac, this property offer...	4 beds \| 2 baths \| 1,608 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2395 Airbnb ROI: N/A Traditional ROI: 4.8%
204 RIDGE Road Winchester, VA Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) o...	3 beds \| 2 baths \| 2,131 sq.ft.	$419,999	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.8% Airbnb Rental Income: $1643 Traditional Rental Income: $2510 Airbnb ROI: 1.42% Traditional ROI: 4.8%
312 FOX Drive Winchester, VA Welcome to this charming all brick ranch style home nestled on a spacious 0.34-acre lot co...	3 beds \| 1 baths \| 1,105 sq.ft.	$375,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.32% Airbnb Rental Income: $1643 Traditional Rental Income: $1827 Airbnb ROI: 1.48% Traditional ROI: 3.32%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

608 GREEN Street

Winchester, VA

3 beds | 1 baths | 1,040 sq.ft.

$289,999

Airbnb cash on cash: 2.33%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1643

Traditional Rental Income: $1737

Airbnb ROI: 2.33%

Traditional ROI: 4.37%

939 WOODLAND AVE

Winchester, VA

2 beds | 2 baths | N/A

$279,900

Airbnb cash on cash: 1.85%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $1436

Traditional Rental Income: $1298

Airbnb ROI: 1.85%

Traditional ROI: 2.95%

110 CARTER PL

Winchester, VA

5 beds | 3 baths | N/A

$494,970

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2719

Airbnb ROI: N/A

Traditional ROI: 4.32%

339 LANNY Drive

Winchester, VA

3 beds | 3 baths | 2,444 sq.ft.

$515,900

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1643

Traditional Rental Income: $2584

Airbnb ROI: 0.66%

Traditional ROI: 3.57%

121 SWEETBRIAR Lane

Winchester, VA

4 beds | 3 baths | 3,442 sq.ft.

$643,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2788

Airbnb ROI: N/A

Traditional ROI: 3.18%

22 HORIZON DR

Winchester, VA

3 beds | 2 baths | 2,092 sq.ft.

$700,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1643

Traditional Rental Income: $2485

Airbnb ROI: 0.17%

Traditional ROI: 2.17%

1049 LAUREL GROVE RD

Winchester, VA

3 beds | 3 baths | N/A

$767,900

Airbnb cash on cash: 0.19%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1643

Traditional Rental Income: $2366

Airbnb ROI: 0.19%

Traditional ROI: 1.85%

881 ADAMS RD

Winchester, VA

3 beds | 2 baths | N/A

$689,900

Airbnb cash on cash: 0.38%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $1643

Traditional Rental Income: $2286

Airbnb ROI: 0.38%