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 113 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
226 TAGGART DRIVE Winchester, VA Welcome to 226 Taggart Drive a sunlit Colonial in the heart of Winchester's sought-after R...	4 beds \| 4 baths \| 4,411 sq.ft.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3501 Airbnb ROI: N/A Traditional ROI: 3.84%
316 VIRGINIA AVENUE Winchester, VA Well maintained Colonial offering timeless character and modern potential in the heart of ...	3 beds \| 1 baths \| 1,192 sq.ft.	$349,900	Airbnb cash on cash: 6.47% Traditional cash on cash: 3.97% Airbnb Rental Income: $3402 Traditional Rental Income: $1825 Airbnb ROI: 6.47% Traditional ROI: 3.97%
2321 STONERIDGE ROAD Winchester, VA Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The o...	4 beds \| 3 baths \| 3,512 sq.ft.	$659,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $2979 Airbnb ROI: N/A Traditional ROI: 2.94%
320 LINDEN DR Winchester, VA 2-1 Buydown being offered. Contact Agent for Details! Experience generational refined l...	4 beds \| 3 baths \| N/A	$633,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 2.43%
224 LAUCK DRIVE Winchester, VA Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buye...	3 beds \| 3 baths \| 2,296 sq.ft.	$525,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 4.12% Airbnb Rental Income: $3402 Traditional Rental Income: $2759 Airbnb ROI: 3.89% Traditional ROI: 4.12%
127 KINROSS DRIVE Winchester, VA Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers...	5 beds \| 4 baths \| 3,494 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.81% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.81%
1517 BROOKDALE COURT Winchester, VA A rare opportunity to own the largest model in the Morlyn Hills neighborhood--more than 65...	4 beds \| 5 baths \| 6,368 sq.ft.	$869,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.89% Airbnb Rental Income: $null Traditional Rental Income: $4616 Airbnb ROI: N/A Traditional ROI: 3.89%
104 AZTEC TRL Winchester, VA Spacious & Renovated 3-Bedroom Home with Den, Patio & Basketball Hoop! Welcome to this bea...	3 beds \| 3 baths \| N/A	$359,900	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.08% Airbnb Rental Income: $3402 Traditional Rental Income: $1631 Airbnb ROI: 6.08% Traditional ROI: 3.08%
369 CHARLES STREET 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.	$305,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 5.73% Airbnb Rental Income: $3402 Traditional Rental Income: $2212 Airbnb ROI: 7.24% Traditional ROI: 5.73%
1950 MELVOR LANE Winchester, VA <html> <head> <title>1950 Melvor Ln</title> <style> body { font-family: sans-serif; margi...	4 beds \| 3 baths \| 3,108 sq.ft.	$690,000	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%
208 OPOSSUM TRAIL Winchester, VA Welcome to this charming two-story home nestled in a peaceful country setting, surrounded ...	3 beds \| 1 baths \| 946 sq.ft.	$249,500	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.65% Airbnb Rental Income: $3402 Traditional Rental Income: $1832 Airbnb ROI: 9.11% Traditional ROI: 5.65%
966 WOODSTOCK LANE Winchester, VA Beautiful 3-bedroom, 2-bath split-foyer home in the heart of Winchester City! The main lev...	3 beds \| 2 baths \| 1,529 sq.ft.	$349,900	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.7% Airbnb Rental Income: $3402 Traditional Rental Income: $2203 Airbnb ROI: 6.04% Traditional ROI: 4.7%
822 PHEASANT DRIVE Winchester, VA PRICE IMPROVEMENT! Welcome to this charming ranch home with spacious backyard and unfinish...	3 beds \| 2 baths \| 1,152 sq.ft.	$274,900	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $3402 Traditional Rental Income: $1986 Airbnb ROI: 8.17% Traditional ROI: 5.62%
3980 MIDDLE ROAD Winchester, VA Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lov...	4 beds \| 4 baths \| 3,504 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3466 Airbnb ROI: N/A Traditional ROI: 3.26%
275 GREENWOOD ROAD Winchester, VA Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access...	3 beds \| 3 baths \| 1,924 sq.ft.	$439,900	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.73% Airbnb Rental Income: $3402 Traditional Rental Income: $2611 Airbnb ROI: 4.82% Traditional ROI: 4.73%
1709 REAVES STREET Winchester, VA Please take off shoes and give feedback. Step into this beautifully cared-for home featuri...	4 beds \| 2 baths \| 1,092 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $2341 Airbnb ROI: N/A Traditional ROI: 3.52%
756 BROOKNEIL DRIVE Winchester, VA Some homes are lived in. Others are lived for. This one? It's the kind of place you wait f...	4 beds \| 4 baths \| 3,942 sq.ft.	$815,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.23% Airbnb Rental Income: $null Traditional Rental Income: $3600 Airbnb ROI: N/A Traditional ROI: 3.23%
601 GROVE STREET Winchester, VA 601 Grove Street, is a single-family home offering a blend of comfort and convenience. Bui...	5 beds \| 2 baths \| 1,152 sq.ft.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.17% Airbnb Rental Income: $null Traditional Rental Income: $2409 Airbnb ROI: N/A Traditional ROI: 6.17%
408 S WASHINGTON STREET Winchester, VA Apple Blossom Parade Route! Opportunities like this dont come around often A beautifully m...	4 beds \| 2 baths \| 2,011 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 3.02%
320 HIGHLAND AVENUE Winchester, VA Welcome to this centrally located home in the heart of Winchester. With easy access to I-8...	3 beds \| 2 baths \| 1,313 sq.ft.	$299,900	Airbnb cash on cash: 7.54% Traditional cash on cash: 5.58% Airbnb Rental Income: $3402 Traditional Rental Income: $2093 Airbnb ROI: 7.54% Traditional ROI: 5.58%
121 N WASHINGTON STREET Winchester, VA A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet k...	3 beds \| 3 baths \| 3,100 sq.ft.	$550,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.77% Airbnb Rental Income: $3402 Traditional Rental Income: $2409 Airbnb ROI: 3.24% Traditional ROI: 2.77%
2623 MIDDLE ROAD Winchester, VA Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located ne...	3 beds \| 3 baths \| 1,984 sq.ft.	$515,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.68% Airbnb Rental Income: $3402 Traditional Rental Income: $2715 Airbnb ROI: 3.54% Traditional ROI: 3.68%
292 FORTRESS DRIVE Winchester, VA Welcome to 292 Fortress Drive, where pride of ownership shines throughout! This stunning h...	5 beds \| 4 baths \| 3,360 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $3608 Airbnb ROI: N/A Traditional ROI: 5.49%
425 BEECHCROFT ROAD Winchester, VA One level living in a sturdy, large (over 2000+/- SF) brick rancher close to all amenities...	4 beds \| 3 baths \| 2,056 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.74% Airbnb Rental Income: $null Traditional Rental Income: $3086 Airbnb ROI: N/A Traditional ROI: 7.74%
621 PANTHER DRIVE Winchester, VA Wilde Acres offers peaceful country living just 1520 minutes from Winchester City. The pro...	2 beds \| 1 baths \| 856 sq.ft.	$279,999	Airbnb cash on cash: 5.31% Traditional cash on cash: 3.86% Airbnb Rental Income: $2499 Traditional Rental Income: $1511 Airbnb ROI: 5.31% Traditional ROI: 3.86%
201 PARKWAY STREET Winchester, VA Freshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated...	4 beds \| 4 baths \| 1,627 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 2.43%
560 FAIR LANE Winchester, VA Welcome home to 560 Fair Lane in Winchester, Virginia. This beautifully maintained Ranch/R...	3 beds \| 3 baths \| 2,491 sq.ft.	$675,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.17% Airbnb Rental Income: $3402 Traditional Rental Income: $2318 Airbnb ROI: 2.69% Traditional ROI: 2.17%
1006 S CAMERON STREET Winchester, VA Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring t...	4 beds \| 1 baths \| 1,732 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $1414 Airbnb ROI: N/A Traditional ROI: 3.67%
247 MCGUIRE ROAD Winchester, VA Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial was fully r...	4 beds \| 3 baths \| 2,859 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 1.55%
109 CRANBERRY COURT Winchester, VA Beautiful 2 bedroom, 2 full bath home in one of Winchester's most sought after 55+ communi...	2 beds \| 2 baths \| 1,686 sq.ft.	$399,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 3.15% Airbnb Rental Income: $2499 Traditional Rental Income: $2028 Airbnb ROI: 2.79% Traditional ROI: 3.15%
101 DELAWARE TRAIL Winchester, VA Price Reduced! Be in before the leaves start to change! You must see this home to believe ...	3 beds \| 2 baths \| 2,302 sq.ft.	$497,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 2.96% Airbnb Rental Income: $3402 Traditional Rental Income: $2053 Airbnb ROI: 4.24% Traditional ROI: 2.96%
110 CARTER PL Winchester, VA Contract fell through! Extensive Renovations: The home has been fully renovated in 2025, ...	5 beds \| 3 baths \| N/A	$499,870	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.27%
707 S BRADDOCK STREET Winchester, VA Welcome to this charming, fully remodeled home located in the heart of Winchester. Experie...	5 beds \| 2 baths \| 2,363 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $1996 Airbnb ROI: N/A Traditional ROI: 3.36%
214 S BRADDOCK STREET Winchester, VA This property is currently zoned as fully commercial but has the potential to be changed t...	5 beds \| 2 baths \| 2,186 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $2451 Airbnb ROI: N/A Traditional ROI: 4.86%
3336 HUNTING RIDGE ROAD Winchester, VA IMPROVED PRICE! Come home to this beautifully designed POOL HOUSE featuring 4-bedrooms, 3-...	4 beds \| 3 baths \| 3,036 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 4.62%
1460 PITCOCK LANE Winchester, VA Escape to Your Private Retreat Just 10 Minutes from Winchester! Dont miss the 3D tour atta...	4 beds \| 4 baths \| 4,949 sq.ft.	$1,125,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.85% Airbnb Rental Income: $null Traditional Rental Income: $3425 Airbnb ROI: N/A Traditional ROI: 1.85%
129 INDIANA Winchester, VA $10,000 CLOSING COSTS WITH ACCEPTABLE CONTRACT. Done and ready! Large lot on private stree...	3 beds \| 3 baths \| 1,660 sq.ft.	$389,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.46% Airbnb Rental Income: $3402 Traditional Rental Income: $2388 Airbnb ROI: 5.17% Traditional ROI: 4.46%
103 FENWICK COURT Winchester, VA REDUCED! REDUCED!! REDUCED!!! Don't miss this well cared for home featuring 5 bedrooms and...	5 beds \| 4 baths \| 1,776 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 5.04%
126 ARMSTRONG PLACE Winchester, VA All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Ma...	4 beds \| 3 baths \| 1,617 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2603 Airbnb ROI: N/A Traditional ROI: 5.27%
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.	$664,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 3.05%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

226 TAGGART DRIVE

Winchester, VA

4 beds | 4 baths | 4,411 sq.ft.

$689,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3501

Airbnb ROI: N/A

Traditional ROI: 3.84%

316 VIRGINIA AVENUE

Winchester, VA

3 beds | 1 baths | 1,192 sq.ft.

$349,900

Airbnb cash on cash: 6.47%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $3402

Traditional Rental Income: $1825

Airbnb ROI: 6.47%

Traditional ROI: 3.97%

2321 STONERIDGE ROAD

Winchester, VA

4 beds | 3 baths | 3,512 sq.ft.

$659,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.94%

Airbnb Rental Income: $null

Traditional Rental Income: $2979

Airbnb ROI: N/A

Traditional ROI: 2.94%

320 LINDEN DR

Winchester, VA

4 beds | 3 baths | N/A

$633,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2624

Airbnb ROI: N/A

Traditional ROI: 2.43%

224 LAUCK DRIVE

Winchester, VA

3 beds | 3 baths | 2,296 sq.ft.

$525,000

Airbnb cash on cash: 3.89%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $3402

Traditional Rental Income: $2759

Airbnb ROI: 3.89%

Traditional ROI: 4.12%

127 KINROSS DRIVE

Winchester, VA

5 beds | 4 baths | 3,494 sq.ft.

$630,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.81%

Airbnb Rental Income: $null

Traditional Rental Income: $3737

Airbnb ROI: N/A

Traditional ROI: 4.81%

1517 BROOKDALE COURT

Winchester, VA

4 beds | 5 baths | 6,368 sq.ft.

$869,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.89%

Airbnb Rental Income: $null

Traditional Rental Income: $4616

Airbnb ROI: N/A

Traditional ROI: 3.89%

104 AZTEC TRL

Winchester, VA

3 beds | 3 baths | N/A

$359,900

Airbnb cash on cash: 6.08%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $3402

Traditional Rental Income: $1631

Airbnb ROI: 6.08%