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 196 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
218 Flanagan Dr Winchester, VA Fabulous Renovated Colonial w/all the bling. Hardwood Flooring on the main w/Plenty of Nat...	4 beds \| 4 baths \| 4,354 sq.ft.	$642,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 2.91%
3466 Middle Rd Winchester, VA Quiet Elegance with Blue Ridge Views: A Remarkable All-Brick Home Tucked away in a peacefu...	3 beds \| 3 baths \| 2,483 sq.ft.	$519,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.36% Airbnb Rental Income: $1134 Traditional Rental Income: $2446 Airbnb ROI: -0.09% Traditional ROI: 3.36%
127 Kinross Dr Winchester, VA A peaceful setting at the edge of Winchester pairs nicely with everyday convenience in thi...	5 beds \| 3 baths \| 3,494 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.83% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.83%
152 DOE TRL Winchester, VA Tucked away on a private, wooded .4-acre lot in Shawneeland, this charming 2-bedroom, 2-ba...	2 beds \| 2 baths \| N/A	$274,900	Airbnb cash on cash: 0.29% Traditional cash on cash: 5.22% Airbnb Rental Income: $956 Traditional Rental Income: $1885 Airbnb ROI: 0.29% Traditional ROI: 5.22%
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.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.47%
519 Whitacre St Winchester, VA Ideally located within one of Winchester's most desirable neighborhoods, Whittier Acres, a...	4 beds \| 2 baths \| 2,408 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2564 Airbnb ROI: N/A Traditional ROI: 4.32%
832 Winder Ct Winchester, VA All-brick rancher located in the sought-after Early's Green at Meadow Branch community, of...	3 beds \| 2 baths \| 1,974 sq.ft.	$589,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.19% Airbnb Rental Income: $1134 Traditional Rental Income: $2436 Airbnb ROI: -0.87% Traditional ROI: 2.19%
199 Meeting House Dr Winchester, VA Legendary Living on 3.46 Acres - 5BR Estate With Mountain Views, Luxe Updates & Iconic His...	5 beds \| 4 baths \| 3,767 sq.ft.	$834,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $4682 Airbnb ROI: N/A Traditional ROI: 4.58%
501 Battle Ave Winchester, VA Relax on the front covered porch of this stone Cape Cod, situated on a large corner lot, s...	3 beds \| 1 baths \| 1,789 sq.ft.	$300,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.71% Airbnb Rental Income: $1134 Traditional Rental Income: $1549 Airbnb ROI: 0.9% Traditional ROI: 3.71%
815 Pheasant Dr Winchester, VA Affordable and move-in ready ranch-style home on a little more than a half acre. The matur...	2 beds \| 1 baths \| 960 sq.ft.	$245,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.36% Airbnb Rental Income: $956 Traditional Rental Income: $1452 Airbnb ROI: 0.71% Traditional ROI: 4.36%
189 Babbs Mountain Rd Winchester, VA Stunning 4 Bed / 3.5 Bath Chalet on 3.26 Acres with Over 6,300 Sq Ft - Minutes from Winche...	4 beds \| 3 baths \| 6,339 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.61% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 1.61%
157 Oak Dr Winchester, VA OPEN HOUSE SPECIAL! This weekend only, seller credit of $10,000 towards buyer closing cost...	4 beds \| 2 baths \| 2,280 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 3.51%
407 Jefferson St Winchester, VA A TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling ...	3 beds \| 1 baths \| 2,805 sq.ft.	$459,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 4.62% Airbnb Rental Income: $1134 Traditional Rental Income: $2824 Airbnb ROI: -0.14% Traditional ROI: 4.62%
132 Amherst St Winchester, VA Charming Victorian home in the Heart of Historic downtown Winchester and located just off ...	4 beds \| 3 baths \| 3,474 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2922 Airbnb ROI: N/A Traditional ROI: 2.91%
129 Doonbeg Ct Winchester, VA ENJOY AN AFFORDABLE RETIREMENT! Newer, beautifully maintained 4-bedroom home with open flo...	4 beds \| 2 baths \| 2,072 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $2623 Airbnb ROI: N/A Traditional ROI: 3.99%
1105 Henry Dr Winchester, VA Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring throu...	4 beds \| 2 baths \| 2,850 sq.ft.	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.22%
2952 Grace St Winchester, VA Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winch...	3 beds \| 1 baths \| 960 sq.ft.	$339,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.93% Airbnb Rental Income: $1134 Traditional Rental Income: $1568 Airbnb ROI: 0.46% Traditional ROI: 2.93%
177 Dicks Hollow Rd Winchester, VA Newly remodeled 2-bedroom, 1-bath rancher just minutes from Winchester! This charming home...	2 beds \| 1 baths \| 650 sq.ft.	$245,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.96% Airbnb Rental Income: $956 Traditional Rental Income: $1301 Airbnb ROI: 0.97% Traditional ROI: 3.96%
511 Grouse Dr Winchester, VA Estimated completion March 2026 This is a fantastic opportunity to purchase a new cons...	3 beds \| 2 baths \| 1,333 sq.ft.	$304,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.55% Airbnb Rental Income: $1134 Traditional Rental Income: $1713 Airbnb ROI: 0.27% Traditional ROI: 3.55%
703 S Loudoun St Winchester, VA Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Ch...	3 beds \| 2 baths \| 1,992 sq.ft.	$484,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.43% Airbnb Rental Income: $1134 Traditional Rental Income: $2427 Airbnb ROI: -0.22% Traditional ROI: 3.43%
100 Winns Cir Winchester, VA Welcome home to Winns Circle! This lovely home is well maintained and ideally located on a...	4 beds \| 2 baths \| 2,636 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.52% Airbnb Rental Income: $null Traditional Rental Income: $3058 Airbnb ROI: N/A Traditional ROI: 5.52%
247 Mcguire Rd Winchester, VA Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot...	4 beds \| 2 baths \| 2,894 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.58% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 1.58%
101 Delaware Trl Winchester, VA Welcome to 101 Delaware Trail, a thoughtfully updated home nestled in the highly desirable...	3 beds \| 2 baths \| 2,094 sq.ft.	$475,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.9% Airbnb Rental Income: $1134 Traditional Rental Income: $2053 Airbnb ROI: 0.12% Traditional ROI: 2.9%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$489,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.37%
129 Indiana Winchester, VA I am done! Large lot on private street with valley views and private. HW floors entire mai...	3 beds \| 2 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.31% Airbnb Rental Income: $1134 Traditional Rental Income: $2388 Airbnb ROI: -0.04% Traditional ROI: 4.31%
Lot 2 Tonto Trl Winchester, VA New Construction: 100% Hardwood - No Carpet! Move into this pristine 3-bed, 2.5-bath Colon...	3 beds \| 2 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.68% Airbnb Rental Income: $1134 Traditional Rental Income: $2529 Airbnb ROI: -0.04% Traditional ROI: 4.68%
1619 Tomahawk Trl Winchester, VA Discover the best value for square footage in this stunning 3 bed, 3 bath home. Perched on...	3 beds \| 3 baths \| 1,914 sq.ft.	$379,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.87% Airbnb Rental Income: $1134 Traditional Rental Income: $2474 Airbnb ROI: 0.05% Traditional ROI: 4.87%
126 Armstrong Pl Winchester, VA SHORT SALE: All brick ranch home with 4 bedrooms close to town and a short walk to the gol...	4 beds \| 3 baths \| 1,617 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $2603 Airbnb ROI: N/A Traditional ROI: 5.66%
230 Tranquil Wood Ln Winchester, VA Are you in search of a spacious, one-level living home that combines privacy and the freed...	3 beds \| 2 baths \| 3,476 sq.ft.	$780,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 2.37% Airbnb Rental Income: $1134 Traditional Rental Income: $2570 Airbnb ROI: -0.13% Traditional ROI: 2.37%
129 Jalapa Trl Winchester, VA Close to Route 81 and 45 minutes to Metro to Dc, Buyer Credit - This beautifully tradition...	3 beds \| 2 baths \| 2,075 sq.ft.	$329,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.08% Airbnb Rental Income: $1134 Traditional Rental Income: $2400 Airbnb ROI: 0.45% Traditional ROI: 5.08%
1049 Laurel Grove Rd Winchester, VA This CUSTOM 3-bedroom, 3-bath home is sited on a private, wooded lot offering stunning mou...	3 beds \| 3 baths \| 2,112 sq.ft.	$767,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.85% Airbnb Rental Income: $1134 Traditional Rental Income: $2366 Airbnb ROI: -0.4% Traditional ROI: 1.85%
21 W Pall Mall St Winchester, VA This inviting Winchester home offers a comfortable blend of character, functionality, and ...	4 beds \| 2 baths \| 1,634 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $1776 Airbnb ROI: N/A Traditional ROI: 2.51%
112 Westwood Cir Winchester, VA Welcome to this ALL brick rambler nestled on 1/2 an acre of mature trees on a corner lot ...	4 beds \| 3 baths \| 2,652 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $3113 Airbnb ROI: N/A Traditional ROI: 4.21%
711 E Cork St Winchester, VA This stunning property boasts a brand-new kitchen with quartz countertops, new appliances ...	2 beds \| 1 baths \| 1,186 sq.ft.	$384,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.93% Airbnb Rental Income: $956 Traditional Rental Income: $2085 Airbnb ROI: -0.16% Traditional ROI: 3.93%
553 Highland Ave Winchester, VA Don't miss taking a LOOK at this property with the new low price of $319K. One Way street ...	3 beds \| 2 baths \| 1,362 sq.ft.	$319,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.52% Airbnb Rental Income: $1134 Traditional Rental Income: $2164 Airbnb ROI: 0.83% Traditional ROI: 5.52%
769 Seldon Dr Winchester, VA Welcome to 769 Seldon Drive-an elegant brick-front colonial situated on nearly half an acr...	5 beds \| 4 baths \| 4,438 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $4891 Airbnb ROI: N/A Traditional ROI: 4.51%
323 Russelcroft Rd Winchester, VA Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living ...	4 beds \| 2 baths \| 1,534 sq.ft.	$358,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: 5.31%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

218 Flanagan Dr

Winchester, VA

4 beds | 4 baths | 4,354 sq.ft.

$642,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2975

Airbnb ROI: N/A

Traditional ROI: 2.91%

3466 Middle Rd

Winchester, VA

3 beds | 3 baths | 2,483 sq.ft.

$519,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1134

Traditional Rental Income: $2446

Airbnb ROI: -0.09%

Traditional ROI: 3.36%

127 Kinross Dr

Winchester, VA

5 beds | 3 baths | 3,494 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.83%

Airbnb Rental Income: $null

Traditional Rental Income: $3737

Airbnb ROI: N/A

Traditional ROI: 4.83%

152 DOE TRL

Winchester, VA

2 beds | 2 baths | N/A

$274,900

Airbnb cash on cash: 0.29%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $956

Traditional Rental Income: $1885

Airbnb ROI: 0.29%

Traditional ROI: 5.22%

1950 Melvor Ln

Winchester, VA

4 beds | 2 baths | 3,108 sq.ft.

$685,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2732

Airbnb ROI: N/A

Traditional ROI: 2.47%

519 Whitacre St

Winchester, VA

4 beds | 2 baths | 2,408 sq.ft.

$435,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2564

Airbnb ROI: N/A

Traditional ROI: 4.32%

832 Winder Ct

Winchester, VA

3 beds | 2 baths | 1,974 sq.ft.

$589,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1134

Traditional Rental Income: $2436

Airbnb ROI: -0.87%

Traditional ROI: 2.19%

199 Meeting House Dr

Winchester, VA

5 beds | 4 baths | 3,767 sq.ft.

$834,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.58%

Airbnb Rental Income: $null

Traditional Rental Income: $4682

Airbnb ROI: N/A