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.
Investment Property for Sale in Winchester, VA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
226 TAGGART DRIVEWinchester, VAWelcome 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
|
316 VIRGINIA AVENUEWinchester, VAWell 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%
|
2321 STONERIDGE ROADWinchester, VAMust 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
|
209 S BRADDOCK STWinchester, VAOpportunity is knocking! Here's your chance to purchase a unique home in the beautiful Win... |
2 beds | 2 baths | N/A |
$285,000 |
Airbnb cash on cash: 4.77%
|
320 LINDEN DRWinchester, 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
|
224 LAUCK DRIVEWinchester, VACustom 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%
|
127 KINROSS DRIVEWinchester, VAWelcome 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
|
1517 BROOKDALE COURTWinchester, VAA 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
|
104 AZTEC TRLWinchester, VASpacious & 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%
|
216 MONTICELLO SQWinchester, VASeller is offering $5,000 toward purchasers closing cost with acceptable offer! Step into ... |
3 beds | 3 baths | N/A |
$350,000 |
Airbnb cash on cash: 6.26%
|
369 CHARLES STREETWinchester, VAThis 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%
|
1950 MELVOR LANEWinchester, 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
|
208 OPOSSUM TRAILWinchester, VAWelcome 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%
|
966 WOODSTOCK LANEWinchester, VABeautiful 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%
|
822 PHEASANT DRIVEWinchester, VAPRICE 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%
|
102 ZEPHYR LANEWinchester, VAMotivated Sellers! Carpet allowance and Professional Cleaning will be provided prior to cl... |
3 beds | 2 baths | 1,634 sq.ft. |
$317,500 |
Airbnb cash on cash: 6.94%
|
3980 MIDDLE ROADWinchester, VACustom, 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
|
275 GREENWOOD ROADWinchester, VACharming 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%
|
1709 REAVES STREETWinchester, VAPlease 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
|
510 N LOUDOUN STREETWinchester, VAAll brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD... |
N/A beds | N/A baths | 2,376 sq.ft. |
$499,900 |
Airbnb cash on cash: 1.27%
|
756 BROOKNEIL DRIVEWinchester, VASome 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
|
601 GROVE STREETWinchester, VA601 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
|
408 S WASHINGTON STREETWinchester, VAApple 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
|
320 HIGHLAND AVENUEWinchester, VAWelcome 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%
|
121 N WASHINGTON STREETWinchester, VAA 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%
|
2623 MIDDLE ROADWinchester, VAWelcome 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%
|
292 FORTRESS DRIVEWinchester, VAWelcome 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
|
425 BEECHCROFT ROADWinchester, VAOne 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
|
621 PANTHER DRIVEWinchester, VAWilde 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%
|
201 PARKWAY STREETWinchester, VAFreshly 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
|
560 FAIR LANEWinchester, VAWelcome 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%
|
1006 S CAMERON STREETWinchester, VADon'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
|
247 MCGUIRE ROADWinchester, VATucked 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
|
109 CRANBERRY COURTWinchester, VABeautiful 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%
|
101 DELAWARE TRAILWinchester, VAPrice 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%
|
110 CARTER PLWinchester, VAContract 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
|
707 S BRADDOCK STREETWinchester, VAWelcome 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
|
214 S BRADDOCK STREETWinchester, VAThis 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
|
3336 HUNTING RIDGE ROADWinchester, VAIMPROVED 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
|
1460 PITCOCK LANEWinchester, VAEscape 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
|
Real Estate investment in Winchester, VA
There are 132 properties for sale in the city of Winchester . The median list price in Winchester is $479,900 and the average price per square foot is $194. In September 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,551.