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 |
|---|---|---|---|
159 Abrams Pointe BlvdWinchester, 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
|
101 Locust AveWinchester, VAWelcome 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%
|
110 Brookland Ct #10Winchester, VAWelcome home to this one-of-a-kind, fully renovated penthouse condo that has been transfor... |
2 beds | 2 baths | 1,173 sq.ft. |
$299,900 |
Airbnb cash on cash: 0.26%
|
108 Norfolk CtWinchester, VAWelcome 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
|
775 Pack Horse RdWinchester, VACompletely 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%
|
900 ENFIELD DriveWinchester, VARecently renovated 4 bedroom, 2 1/2 bath county home with beautiful views! Corner lot on p... |
4 beds | 3 baths | 2,550 sq.ft. |
$370,000 |
Airbnb cash on cash: N/A
|
116 Mcclure WayWinchester, VAIf 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
|
2967 SORRELL CourtWinchester, VAThis diamond in the rough has solid bones and plenty of potential for the right buyer. The... |
2 beds | 3 baths | 1,280 sq.ft. |
$249,000 |
Airbnb cash on cash: 1.03%
|
1004 Heth PlWinchester, VAStepping 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
|
101 Charlton RdWinchester, VAWelcome 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
|
802 E Cork StWinchester, VAMotivated 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
|
420 E Pall Mall StWinchester, 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%
|
122 Armstrong PlWinchester, 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
|
369 Charles StWinchester, VAThis 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%
|
1950 Melvor LnWinchester, VAStep 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
|
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. |
$379,900 |
Airbnb cash on cash: -0.36%
|
118 1/2 E Cork StWinchester, VASeeking the perfect blend of historic character and modern urban living? This exceptional ... |
2 beds | 2 baths | 1,419 sq.ft. |
$399,900 |
Airbnb cash on cash: -0.1%
|
146 Darby DrWinchester, VABeautiful 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
|
100 Oakmont CirWinchester, 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%
|
137 Old Forest CirWinchester, VANestled 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
|
110 Rugby PlWinchester, 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%
|
304 Shenandoah AveWinchester, VAClassic 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%
|
115 Marion DrWinchester, VASituated 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
|
121 Cherokee TrlWinchester, VALake 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%
|
832 Winder CtWinchester, VABack 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%
|
824 APPLESEED CourtWinchester, VAWelcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hil... |
3 beds | 3 baths | 2,052 sq.ft. |
$365,000 |
Airbnb cash on cash: 1.15%
|
593 N Kent StWinchester, VAThis 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%
|
135 S Kent St #202Winchester, VAStep into the charm of Historic Downtown Winchester with this beautifully renovated Urban ... |
1 beds | 1 baths | 740 sq.ft. |
$259,000 |
Airbnb cash on cash: -0.31%
|
621 Patterson AveWinchester, VAEnchanting Cape Cod in an ideal in""ââ¬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
|
104 Bramble CtWinchester, VAWelcome 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
|
115 Brockham CtWinchester, VAExcellent value in the neighborhood!! Beautifully upgraded, like-new 3-bedroom, 2 full and... |
4 beds | 2 baths | 2,376 sq.ft. |
$400,000 |
Airbnb cash on cash: 1.09%
|
109 Gannentaha TrlWinchester, VAPride 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%
|
Real Estate investment in Winchester, VA
There are 363 properties for sale in the city of Winchester . The median list price in Winchester is $373,272 and the average price per square foot is $163. In August 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,457.