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 |
|---|---|---|---|
2643 MIDDLE RoadWinchester, VALocation Location Location! NO HOA!!! Hardwood floors on the main level. Formal living and... |
4 beds | 4 baths | 2,524 sq.ft. |
$500,000 |
Airbnb cash on cash: N/A
|
719 Smithfield AvenueWinchester, VABringing all the bungalow love! This 2 bed/1 bath home is move-in ready after a 2025 Refre... |
2 beds | 1 baths | 720 sq.ft. |
$275,000 |
Airbnb cash on cash: 1.2%
|
3466 MIDDLE RDWinchester, VAQuiet Elegance with Blue Ridge Views: A Remarkable All-Brick Home Tucked away in a peacefu... |
3 beds | 3 baths | N/A |
$489,999 |
Airbnb cash on cash: -0.24%
|
108 NORFOLK CourtWinchester, VAWelcome to 108 Norfolk Court in Winchester, where luxury, comfort, and an impressive amoun... |
4 beds | 5 baths | 5,020 sq.ft. |
$689,900 |
Airbnb cash on cash: N/A
|
171 LAUREL GROVE RoadWinchester, VAHistoric 1800s farmhouse on 5 unrestricted acres just outside Winchester, Virginia, in des... |
3 beds | 3 baths | 3,052 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.56%
|
127 KINROSS DriveWinchester, VAA peaceful setting at the edge of Winchester pairs nicely with everyday convenience in thi... |
5 beds | 4 baths | 3,494 sq.ft. |
$600,000 |
Airbnb cash on cash: N/A
|
110 MEADOWVIEW CourtWinchester, VAReady for new owners, this welllocated home on Winchester's east side offers commuter conv... |
4 beds | 3 baths | 1,680 sq.ft. |
$364,999 |
Airbnb cash on cash: N/A
|
1950 MELVOR LaneWinchester, VAStep into this meticulously maintained colonial home, a testament to quality craftsmanship... |
4 beds | 3 baths | 3,108 sq.ft. |
$685,000 |
Airbnb cash on cash: N/A
|
1851 MELVOR LaneWinchester, VAExtremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottag... |
2 beds | 2 baths | 1,405 sq.ft. |
$399,900 |
Airbnb cash on cash: -0.5%
|
145 Graywolf TrailWinchester, VALooking for privacy, modern finishes, and a extra lot? This 2021-built Colonial checks all... |
3 beds | 3 baths | 1,660 sq.ft. |
$375,000 |
Airbnb cash on cash: -0.21%
|
832 WINDER CourtWinchester, VAAll-brick rancher located in the sought-after Early's Green at Meadow Branch community, of... |
3 beds | 2 baths | 1,974 sq.ft. |
$550,000 |
Airbnb cash on cash: -1.05%
|
610 PUMA TrailWinchester, VATucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl of... |
2 beds | 1 baths | 560 sq.ft. |
$224,990 |
Airbnb cash on cash: 1.39%
|
157 OAK DriveWinchester, VANEW PRICE ALERT! <br><br> Welcome home to 157 Oak Dr. in Winchester, VA-an inviting proper... |
4 beds | 3 baths | 2,280 sq.ft. |
$550,000 |
Airbnb cash on cash: N/A
|
321 COPPERFIELD LaneWinchester, VASuper cute 3 level townhome with a great design, two full baths one in the basement one in... |
3 beds | 3 baths | 1,840 sq.ft. |
$324,989 |
Airbnb cash on cash: -0.2%
|
104 INCA TrailWinchester, VAFantastic Opportunity! Unique home features newer stainless appliances, newer roof, and ne... |
2 beds | 1 baths | 900 sq.ft. |
$155,000 |
Airbnb cash on cash: 2.53%
|
132 AMHERST StreetWinchester, VACharming Victorian home in the heart of Winchester's historic downtown, move-in ready and ... |
4 beds | 4 baths | 3,474 sq.ft. |
$650,000 |
Airbnb cash on cash: N/A
|
129 DOONBEG CourtWinchester, VAENJOY YOUR RETIREMENT! Newer, beautifully maintained 4-bedroom home with open floor plan a... |
4 beds | 3 baths | 2,072 sq.ft. |
$450,000 |
Airbnb cash on cash: N/A
|
1105 HENRY DriveWinchester, VAHome offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring throu... |
4 beds | 3 baths | 2,850 sq.ft. |
$434,999 |
Airbnb cash on cash: N/A
|
317 GRAY AvenueWinchester, VAWelcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic ch... |
4 beds | 3 baths | 1,536 sq.ft. |
$389,990 |
Airbnb cash on cash: N/A
|
2952 GRACE StreetWinchester, VACharming 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: 0.19%
|
177 DICKS HOLLOW RoadWinchester, VANewly remodeled turn-key starter home with modern updates. 2-bedroom 1-bathroom rancher ju... |
2 beds | 1 baths | 650 sq.ft. |
$245,000 |
Airbnb cash on cash: 1.4%
|
174 WILLIAMSON RoadWinchester, VAIf you want more space and are priced out of Northern Virginia, come to Winchester! If you... |
5 beds | 4 baths | 4,008 sq.ft. |
$775,000 |
Airbnb cash on cash: N/A
|
511 GROUSE DriveWinchester, VA**Estimated completion by end of March 2026** This is a fantastic opportunity to purchase ... |
3 beds | 2 baths | 1,333 sq.ft. |
$304,900 |
Airbnb cash on cash: -0.04%
|
Real Estate investment in Winchester, VA
There are 202 properties for sale in the city of Winchester . The median list price in Winchester is $414,900 and the average price per square foot is $197. In March 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,328.