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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
159 Abrams Pointe Blvd Winchester, VA ***You could get up to $3,000 with use of preferred lender for closing cost assistance or ...	5 beds \| 4 baths \| 3,963 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $4656 Airbnb ROI: N/A Traditional ROI: 4.87%
101 Locust Ave Winchester, VA Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This sol...	3 beds \| 2 baths \| 1,566 sq.ft.	$330,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 4.77% Airbnb Rental Income: $1519 Traditional Rental Income: $2225 Airbnb ROI: 1.27% Traditional ROI: 4.77%
108 Norfolk Ct Winchester, VA Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home ...	4 beds \| 4 baths \| 4,918 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $4402 Airbnb ROI: N/A Traditional ROI: 5.06%
775 Pack Horse Rd Winchester, VA Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in F...	3 beds \| 2 baths \| 1,188 sq.ft.	$420,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.41% Airbnb Rental Income: $1519 Traditional Rental Income: $1940 Airbnb ROI: 1.22% Traditional ROI: 3.41%
116 Mcclure Way Winchester, VA If you have been waiting to move into Red Fox Run there is no better opportunity than this...	4 beds \| 2 baths \| 2,360 sq.ft.	$524,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 3.81%
1004 Heth Pl Winchester, VA Stepping onto the Southern style covered front porc.h you enter the large foyer with a Sc...	4 beds \| 3 baths \| 4,970 sq.ft.	$1,179,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $4479 Airbnb ROI: N/A Traditional ROI: 2.4%
101 Charlton Rd Winchester, VA Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desira...	4 beds \| 2 baths \| 1,714 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $2498 Airbnb ROI: N/A Traditional ROI: 4.63%
802 E Cork St Winchester, VA Motivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, ...	4 beds \| 2 baths \| 1,996 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.51% Airbnb Rental Income: $null Traditional Rental Income: $2505 Airbnb ROI: N/A Traditional ROI: 6.51%
420 E Pall Mall St Winchester, VA "Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is r...	2 beds \| 2 baths \| 1,395 sq.ft.	$339,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.45% Airbnb Rental Income: $1126 Traditional Rental Income: $2081 Airbnb ROI: 0.34% Traditional ROI: 4.45%
122 Armstrong Pl Winchester, VA "Welcome to 122 Armstrong Place, a beautifully maintained 4-bedroom, 3-bath retreat locate...	4 beds \| 3 baths \| 2,706 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 4.73%
369 Charles St Winchester, VA This two-story home offers classic charm with a covered front porch, fenced backyard, and ...	3 beds \| 2 baths \| 1,526 sq.ft.	$225,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 8.07% Airbnb Rental Income: $1519 Traditional Rental Income: $2212 Airbnb ROI: 2.74% Traditional ROI: 8.07%
1950 Melvor Ln Winchester, VA Step into this meticulously maintained colonial home, a testament to quality craftsmanship...	4 beds \| 2 baths \| 3,108 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.45%
1851 MELVOR Lane Winchester, VA Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottag...	2 beds \| 2 baths \| 1,405 sq.ft.	$379,900	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.55% Airbnb Rental Income: $1126 Traditional Rental Income: $2144 Airbnb ROI: -0.36% Traditional ROI: 3.55%
146 Darby Dr Winchester, VA Beautiful brick-front home in sought-after Ravenwing offering three finished levels and ex...	4 beds \| 3 baths \| 3,924 sq.ft.	$674,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $3494 Airbnb ROI: N/A Traditional ROI: 3.95%
100 Oakmont Cir Winchester, VA Move-in ready! Welcome to 100 Oakmont Circle, a beautifully updated 3-bedroom, 1.5-bat...	3 beds \| 1 baths \| 1,248 sq.ft.	$355,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 4.48% Airbnb Rental Income: $1519 Traditional Rental Income: $2063 Airbnb ROI: 1.53% Traditional ROI: 4.48%
137 Old Forest Cir Winchester, VA Nestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded p...	4 beds \| 3 baths \| 4,152 sq.ft.	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $3872 Airbnb ROI: N/A Traditional ROI: 2.81%
110 Rugby Pl Winchester, VA Bank approved Short sale price opportunity with a significant price reduction-bring ...	3 beds \| 2 baths \| 1,625 sq.ft.	$370,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.93% Airbnb Rental Income: $1519 Traditional Rental Income: $2358 Airbnb ROI: 1.24% Traditional ROI: 4.93%
304 Shenandoah Ave Winchester, VA Classic charm in this brick Cape Cod located in Winchester City, just minutes from shoppin...	3 beds \| 1 baths \| 1,094 sq.ft.	$285,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 5.31% Airbnb Rental Income: $1519 Traditional Rental Income: $2009 Airbnb ROI: 1.84% Traditional ROI: 5.31%
115 Marion Dr Winchester, VA Situated on approximately 2.57 acres in Frederick County, this 4-bedroom, 2.5-bath Traditi...	4 beds \| 2 baths \| 2,967 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2963 Airbnb ROI: N/A Traditional ROI: 3.35%
121 Cherokee Trl Winchester, VA Lake and mountain views, a private in-ground pool, and an adjoining .63-acre lot - this be...	3 beds \| 3 baths \| 2,650 sq.ft.	$474,500	Airbnb cash on cash: 0.84% Traditional cash on cash: 5.89% Airbnb Rental Income: $1519 Traditional Rental Income: $3319 Airbnb ROI: 0.84% Traditional ROI: 5.89%
832 Winder Ct Winchester, VA Back on the market, at no fault of the seller. All-brick rancher located in the sought-aft...	3 beds \| 2 baths \| 1,974 sq.ft.	$519,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.57% Airbnb Rental Income: $1519 Traditional Rental Income: $2436 Airbnb ROI: -0.2% Traditional ROI: 2.57%
593 N Kent St Winchester, VA This charming home, a short walk from historic Winchester, underwent a complete studs up r...	3 beds \| 2 baths \| 1,310 sq.ft.	$319,950	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.15% Airbnb Rental Income: $1519 Traditional Rental Income: $2297 Airbnb ROI: 2.1% Traditional ROI: 6.15%
621 Patterson Ave Winchester, VA Enchanting Cape Cod in an ideal in""Ã¢â¬Ëtown location, this home has a welcoming ease t...	4 beds \| 2 baths \| 2,050 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $2408 Airbnb ROI: N/A Traditional ROI: 5.03%
104 Bramble Ct Winchester, VA Welcome home to this beautifully maintained 3-level Colonial, perfectly situated on a quie...	4 beds \| 2 baths \| 2,904 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 3.24%
109 Gannentaha Trl Winchester, VA Pride of ownership shines throughout this exceptionally well-maintained and thoughtfully u...	2 beds \| 2 baths \| 1,555 sq.ft.	$325,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.61% Airbnb Rental Income: $1126 Traditional Rental Income: $1680 Airbnb ROI: 0.56% Traditional ROI: 3.61%
516 Deer Creek Rd Winchester, VA Nestled on a private 2-acre lot in the desirable Hogue Creek subdivision, this charming 3-...	3 beds \| 3 baths \| 1,814 sq.ft.	$495,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.21% Airbnb Rental Income: $1519 Traditional Rental Income: $2697 Airbnb ROI: 0.71% Traditional ROI: 4.21%
1015 Redbud Rd Winchester, VA Set on over 10private acres in the quiet Locust Level Estates community, this beautifully ...	4 beds \| 4 baths \| 4,188 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $4576 Airbnb ROI: N/A Traditional ROI: 3%
151 Travis Ct Winchester, VA Welcome to 151 Travis Court, a beautifully maintained 5-bedroom, 3.5-bath Colonial tucked ...	5 beds \| 3 baths \| 3,518 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $3546 Airbnb ROI: N/A Traditional ROI: 5.11%
321 N Kent St Winchester, VA Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall...	3 beds \| 1 baths \| 1,280 sq.ft.	$262,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 5.79% Airbnb Rental Income: $1519 Traditional Rental Income: $1969 Airbnb ROI: 2.28% Traditional ROI: 5.79%
211 Flanagan Dr Winchester, VA Pictures coming soon. Prime Location in Raven Wing! This beautiful Colonial home offers th...	4 beds \| 3 baths \| 4,120 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $3412 Airbnb ROI: N/A Traditional ROI: 4.17%
528 Battle Ave Winchester, VA Adorable Cape Cod in the heart of Winchester! Beautifully appointed with hardwood floors, ...	3 beds \| 1 baths \| 1,988 sq.ft.	$320,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.69% Airbnb Rental Income: $1519 Traditional Rental Income: $1689 Airbnb ROI: 1.65% Traditional ROI: 3.69%
605 Dunlap St Winchester, VA Priced to reflect the need for some updating, this home offers opportunities and personali...	5 beds \| 2 baths \| 1,011 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2388 Airbnb ROI: N/A Traditional ROI: 4.84%
127 GERONIMO Trail Winchester, VA Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfe...	3 beds \| 1 baths \| 970 sq.ft.	$199,900	Airbnb cash on cash: 3.75% Traditional cash on cash: 7% Airbnb Rental Income: $1519 Traditional Rental Income: $1693 Airbnb ROI: 3.75% Traditional ROI: 7%
703 S Loudoun St Winchester, VA *4.25% INTEREST RATE AVAILABLE* Located in the heart of Winchester's Historic District...	3 beds \| 2 baths \| 1,992 sq.ft.	$450,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.82% Airbnb Rental Income: $1519 Traditional Rental Income: $2427 Airbnb ROI: 0.61% Traditional ROI: 3.82%
1617 Tomahawk Winchester, VA Welcome home to this beautifully maintained split-foyer residence offering the perfect ble...	3 beds \| 3 baths \| 1,850 sq.ft.	$389,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.14% Airbnb Rental Income: $1519 Traditional Rental Income: $2265 Airbnb ROI: 0.88% Traditional ROI: 4.14%
145 Wilkins Dr Winchester, VA Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! Welcome home t...	4 beds \| 2 baths \| 2,572 sq.ft.	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: 3.68%
132 Geronimo Trl Winchester, VA Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet ...	3 beds \| 2 baths \| 1,232 sq.ft.	$290,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 4.87% Airbnb Rental Income: $1519 Traditional Rental Income: $1847 Airbnb ROI: 2.05% Traditional ROI: 4.87%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

159 Abrams Pointe Blvd

Winchester, VA

5 beds | 4 baths | 3,963 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $4656

Airbnb ROI: N/A

Traditional ROI: 4.87%

101 Locust Ave

Winchester, VA

3 beds | 2 baths | 1,566 sq.ft.

$330,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1519

Traditional Rental Income: $2225

Airbnb ROI: 1.27%

Traditional ROI: 4.77%

108 Norfolk Ct

Winchester, VA

4 beds | 4 baths | 4,918 sq.ft.

$690,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.06%

Airbnb Rental Income: $null

Traditional Rental Income: $4402

Airbnb ROI: N/A

Traditional ROI: 5.06%

775 Pack Horse Rd

Winchester, VA

3 beds | 2 baths | 1,188 sq.ft.

$420,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $1519

Traditional Rental Income: $1940

Airbnb ROI: 1.22%

Traditional ROI: 3.41%

116 Mcclure Way

Winchester, VA

4 beds | 2 baths | 2,360 sq.ft.

$524,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2666

Airbnb ROI: N/A

Traditional ROI: 3.81%

1004 Heth Pl

Winchester, VA

4 beds | 3 baths | 4,970 sq.ft.

$1,179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.4%

Airbnb Rental Income: $null

Traditional Rental Income: $4479

Airbnb ROI: N/A

Traditional ROI: 2.4%

101 Charlton Rd

Winchester, VA

4 beds | 2 baths | 1,714 sq.ft.

$420,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2498

Airbnb ROI: N/A

Traditional ROI: 4.63%

802 E Cork St

Winchester, VA

4 beds | 2 baths | 1,996 sq.ft.

$309,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2505

Airbnb ROI: N/A