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 |
|---|---|---|---|
719 Smithfield AvenueWinchester, VABringing all the bungalow love! . **$8,000 closing cost credit to buyer with acceptable of... |
2 beds | 1 baths | 720 sq.ft. |
$274,900 |
Airbnb cash on cash: 1.06%
|
3466 MIDDLE RDWinchester, VAWelcome to a private retreat where timeless charm meets peaceful mountain beauty. Set on 0... |
3 beds | 3 baths | N/A |
$489,999 |
Airbnb cash on cash: -0.72%
|
109 HURON TRLWinchester, VADiscover this inviting 3-bedroom, 2-bath tri""ââ¬Ëlevel home, offering flexible living ... |
3 beds | 2 baths | N/A |
$369,900 |
Airbnb cash on cash: -0.4%
|
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: -0.88%
|
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: -0.42%
|
13 E LEICESTER StreetWinchester, VAIncredible location, incredible home! Relax on the elevated front porch overlooking Leices... |
3 beds | 2 baths | 1,601 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.44%
|
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
|
1239 CEDAR GROVE RoadWinchester, VAExperience the perfect blend of historic artistry and modern convenience in this stunning ... |
3 beds | 2 baths | 1,793 sq.ft. |
$575,000 |
Airbnb cash on cash: -0.68%
|
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. |
$273,000 |
Airbnb cash on cash: 0.55%
|
704 WATSON AvenueWinchester, VABeautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 ... |
2 beds | 2 baths | 864 sq.ft. |
$295,000 |
Airbnb cash on cash: 0.52%
|
16 S PLEASANT VALLEY RoadWinchester, VAWelcome to this one-of-a-kind property offering a unique and inviting layout designed with... |
3 beds | 3 baths | 1,600 sq.ft. |
$360,000 |
Airbnb cash on cash: -0.69%
|
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. |
$399,900 |
Airbnb cash on cash: -0.6%
|
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: -1.48%
|
199 MEETING HOUSE DriveWinchester, VALegendary Living on 3.46 Acres - 5BR Estate With Mountain Views, Luxe Updates & Iconic His... |
5 beds | 5 baths | 3,767 sq.ft. |
$795,000 |
Airbnb cash on cash: N/A
|
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: 1.21%
|
540 Eagle PlaceWinchester, VAGreat opportunity for a rental investment! This well-maintained one-level rancher is tucke... |
3 beds | 2 baths | 1,450 sq.ft. |
$385,000 |
Airbnb cash on cash: -0.65%
|
157 OAK DriveWinchester, VASTOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring i... |
4 beds | 3 baths | 2,280 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
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
|
127 GERONIMO TrailWinchester, VANestled in the serene Shawneeland community, this charming ranch-style home offers a perfe... |
3 beds | 1 baths | 970 sq.ft. |
$235,000 |
Airbnb cash on cash: 0.17%
|
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
|
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. |
$749,000 |
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: -0.82%
|
25 W SOUTHWERK StreetWinchester, VAWelcome to this beautifully updated gem in the heart of Winchester! From the moment you ar... |
3 beds | 3 baths | 1,904 sq.ft. |
$449,000 |
Airbnb cash on cash: -0.6%
|
105 AMBERFIELD CourtWinchester, VAMove in Ready!!! Low $150/month HOA fee. Nestled in the serene enclave of Abram's Chase an... |
2 beds | 2 baths | 1,800 sq.ft. |
$515,000 |
Airbnb cash on cash: -0.56%
|
153 HARVEST RIDGE DriveWinchester, VAWelcome to 153 Harvest Ridge Drive, a beautifully appointed home tucked within the highly ... |
4 beds | 3 baths | 3,157 sq.ft. |
$642,900 |
Airbnb cash on cash: N/A
|
221 BROAD AvenueWinchester, VAThoughtfully designed for comfortable everyday living, this home offers a warm and invitin... |
3 beds | 3 baths | 800 sq.ft. |
$325,000 |
Airbnb cash on cash: -0.2%
|
433 BEECHCROFT RoadWinchester, VAExplore 433 Beechcroft Road, located in the desirable Cedarmeade community. This lovely on... |
4 beds | 2 baths | 1,328 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
307 FOX RUN LaneWinchester, VAWake up to breathtaking views of the Shenandoah Valley every day in this peaceful, beautif... |
3 beds | 1 baths | 2,683 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.47%
|
540 MONTICELLO StreetWinchester, VAWelcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Dow... |
N/A beds | N/A baths | 4,396 sq.ft. |
$605,000 |
Airbnb cash on cash: -0.72%
|
616 CARDINAL DriveWinchester, VANestled in the serene Wilde Acres community, this exquisite split foyer home, built in 202... |
3 beds | 2 baths | 1,510 sq.ft. |
$370,000 |
Airbnb cash on cash: -0.41%
|
128 LITTLE RIVER DriveWinchester, VA3% SELLER SUBSIDY TO BUYER AT CLOSING! TURN KEY and in EXCELLENT CONDITION! Finished basem... |
2 beds | 2 baths | 1,600 sq.ft. |
$279,000 |
Airbnb cash on cash: 0.66%
|
2431 CEDAR CREEK GradeWinchester, VAThis is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/... |
3 beds | 2 baths | 1,036 sq.ft. |
$370,000 |
Airbnb cash on cash: -0.35%
|
112 W GERMAIN StreetWinchester, VA100-Year-Old Downtown Winchester Charmer - Fully Reimagined in 2025! This stunning, fully ... |
3 beds | 3 baths | 1,650 sq.ft. |
$675,000 |
Airbnb cash on cash: -0.62%
|
1049 LAUREL GROVE RDWinchester, VAThis custom-built 3-bedroom, 3-bath home is perfectly positioned on a private, wooded lot ... |
3 beds | 3 baths | N/A |
$767,900 |
Airbnb cash on cash: -0.85%
|
1419 RAMSEUR LaneWinchester, VAThis property is NOT in a 55+ community. A rare opportunity for one-level living with over... |
4 beds | 3 baths | 3,482 sq.ft. |
$735,000 |
Airbnb cash on cash: N/A
|
711 E CORK StreetWinchester, VAThis stunning property boasts a brand-new kitchen with quartz countertops, new appliances ... |
2 beds | 2 baths | 1,186 sq.ft. |
$384,900 |
Airbnb cash on cash: 0.02%
|
769 SELDON DriveWinchester, VAWelcome to 769 Seldon Drive-an elegant brick-front colonial situated on nearly half an acr... |
5 beds | 5 baths | 4,438 sq.ft. |
$884,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, VA
There are 149 properties for sale in the city of Winchester . The median list price in Winchester is $424,900 and the average price per square foot is $195. In April 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,400.