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 BoulevardWinchester, VA***You could get up to $3,000 with use of preferred lender for closing cost assistance or ... |
5 beds | 5 baths | 3,963 sq.ft. |
$775,000 |
Airbnb cash on cash: N/A
|
101 LOCUST AvenueWinchester, VAWelcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This sol... |
3 beds | 3 baths | 1,566 sq.ft. |
$349,000 |
Airbnb cash on cash: 1.4%
|
110 BROOKLAND Court #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: 0.74%
|
110 GRINDSTONE DriveWinchester, VAPrivate pool, half-acre homesite, main-level living, and a fully finished lower-level livi... |
4 beds | 4 baths | 4,055 sq.ft. |
$529,900 |
Airbnb cash on cash: N/A
|
108 NORFOLK CourtWinchester, VAWelcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home ... |
4 beds | 5 baths | 4,918 sq.ft. |
$700,000 |
Airbnb cash on cash: N/A
|
775 PACK HORSE RoadWinchester, 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: 1.33%
|
13 E LEICESTER StreetWinchester, VAIncredible location, incredible home! Relax on the elevated front porch overlooking Leices... |
3 beds | 2 baths | 1,601 sq.ft. |
$385,000 |
Airbnb cash on cash: 1.48%
|
167 FALCON TRLWinchester, VADiscover the perfect blend of comfort and charm of this contemporary home nestled on a lar... |
3 beds | 2 baths | 1,470 sq.ft. |
$349,000 |
Airbnb cash on cash: 1.71%
|
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. |
$255,000 |
Airbnb cash on cash: 1.55%
|
1004 HETH PLWinchester, VAStepping onto the Southern style covered front porc.h you enter the large foyer with a Sc... |
4 beds | 5 baths | N/A |
$1,179,000 |
Airbnb cash on cash: N/A
|
101 CHARLTON RoadWinchester, VAWelcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desira... |
4 beds | 3 baths | 1,714 sq.ft. |
$429,900 |
Airbnb cash on cash: N/A
|
405 SPRING VALLEY DriveWinchester, VANEW PRICE REDUCTION! NO HOA!!! Built in 1971, this 4 Bed/2.5 Bath home is located on over ... |
4 beds | 3 baths | 4,050 sq.ft. |
$679,900 |
Airbnb cash on cash: N/A
|
802 E CORK StreetWinchester, VAMotivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, ... |
4 beds | 2 baths | 1,996 sq.ft. |
$324,000 |
Airbnb cash on cash: N/A
|
420 E PALL MALL StreetWinchester, 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. |
$344,900 |
Airbnb cash on cash: 0.76%
|
122 ARMSTRONG PlaceWinchester, VA"Welcome to 122 Armstrong Place, a beautifully maintained 4-bedroom, 3-bath retreat locate... |
4 beds | 3 baths | 2,706 sq.ft. |
$549,000 |
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. |
$689,000 |
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: 0.02%
|
118 1/2 E CORK StreetWinchester, VASeeking the perfect blend of historic character and modern urban living? This exceptional ... |
2 beds | 2 baths | 1,031 sq.ft. |
$429,000 |
Airbnb cash on cash: 0.2%
|
137 OLD FOREST CircleWinchester, VANestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded p... |
4 beds | 4 baths | 4,152 sq.ft. |
$989,000 |
Airbnb cash on cash: N/A
|
110 RUGBY PlaceWinchester, VA** Bank approved Short sale price ** opportunity with a significant price reduction-bring ... |
3 beds | 3 baths | 1,625 sq.ft. |
$370,000 |
Airbnb cash on cash: 1.37%
|
121 CHEROKEE TrailWinchester, VALake and mountain views, a private in-ground pool, and an adjoining .63-acre lot - this be... |
3 beds | 4 baths | 2,650 sq.ft. |
$474,500 |
Airbnb cash on cash: 0.94%
|
593 N KENT StreetWinchester, VAThis charming home, a short walk from historic Winchester, underwent a complete studs up r... |
3 beds | 3 baths | 1,310 sq.ft. |
$319,950 |
Airbnb cash on cash: 2.24%
|
621 PATTERSON AVEWinchester, VAEnchanting Cape Cod in an ideal in""ââ¬Ëtown location, this home has a welcoming ease t... |
4 beds | 3 baths | N/A |
$364,900 |
Airbnb cash on cash: N/A
|
104 BRAMBLE CourtWinchester, VAWelcome home to this beautifully maintained 3-level Colonial, perfectly situated on a quie... |
4 beds | 3 baths | 2,904 sq.ft. |
$665,000 |
Airbnb cash on cash: N/A
|
2561 APPLE PIE RIDGE RoadWinchester, VAWelcome home to this beautifully updated rambler, offering comfort, character, and room to... |
3 beds | 2 baths | 1,412 sq.ft. |
$349,900 |
Airbnb cash on cash: 1.77%
|
115 BROCKHAM CourtWinchester, VABeautifully upgraded, like-new 3-bedroom, 2 full and 2 half bath townhouse with a 2-car ga... |
3 beds | 4 baths | 2,376 sq.ft. |
$409,000 |
Airbnb cash on cash: 1.16%
|
516 DEER CREEK RoadWinchester, VANestled on a private 2-acre lot in the desirable Hogue Creek subdivision, this charming 3-... |
3 beds | 4 baths | 1,814 sq.ft. |
$515,000 |
Airbnb cash on cash: 0.74%
|
Real Estate investment in Winchester, VA
There are 267 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 $167. In July 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,461.