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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
218 Flanagan Dr Winchester, VA Fabulous Renovated Colonial w/all the bling. Hardwood Flooring on the main w/Plenty of Nat...	4 beds \| 4 baths \| 4,354 sq.ft.	$642,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 2.91%
3466 Middle Rd Winchester, VA Quiet Elegance with Blue Ridge Views: A Remarkable All-Brick Home Tucked away in a peacefu...	3 beds \| 3 baths \| 2,483 sq.ft.	$519,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.36% Airbnb Rental Income: $1134 Traditional Rental Income: $2446 Airbnb ROI: -0.09% Traditional ROI: 3.36%
127 Kinross Dr Winchester, VA A peaceful setting at the edge of Winchester pairs nicely with everyday convenience in thi...	5 beds \| 3 baths \| 3,494 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.83% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.83%
152 DOE TRL Winchester, VA Tucked away on a private, wooded .4-acre lot in Shawneeland, this charming 2-bedroom, 2-ba...	2 beds \| 2 baths \| N/A	$274,900	Airbnb cash on cash: 0.29% Traditional cash on cash: 5.22% Airbnb Rental Income: $956 Traditional Rental Income: $1885 Airbnb ROI: 0.29% Traditional ROI: 5.22%
369 Charles St Winchester, VA This 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: 1.23% Traditional cash on cash: 8.07% Airbnb Rental Income: $1134 Traditional Rental Income: $2212 Airbnb ROI: 1.23% Traditional ROI: 8.07%
1950 Melvor Ln Winchester, VA Step into this meticulously maintained colonial home, a testament to quality craftsmanship...	4 beds \| 2 baths \| 3,108 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.47%
519 Whitacre St Winchester, VA Ideally located within one of Winchester's most desirable neighborhoods, Whittier Acres, a...	4 beds \| 2 baths \| 2,408 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2564 Airbnb ROI: N/A Traditional ROI: 4.32%
832 Winder Ct Winchester, VA All-brick rancher located in the sought-after Early's Green at Meadow Branch community, of...	3 beds \| 2 baths \| 1,974 sq.ft.	$589,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.19% Airbnb Rental Income: $1134 Traditional Rental Income: $2436 Airbnb ROI: -0.87% Traditional ROI: 2.19%
199 Meeting House Dr Winchester, VA Legendary Living on 3.46 Acres - 5BR Estate With Mountain Views, Luxe Updates & Iconic His...	5 beds \| 4 baths \| 3,767 sq.ft.	$834,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $4682 Airbnb ROI: N/A Traditional ROI: 4.58%
501 Battle Ave Winchester, VA Relax on the front covered porch of this stone Cape Cod, situated on a large corner lot, s...	3 beds \| 1 baths \| 1,789 sq.ft.	$300,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.71% Airbnb Rental Income: $1134 Traditional Rental Income: $1549 Airbnb ROI: 0.9% Traditional ROI: 3.71%
815 Pheasant Dr Winchester, VA Affordable and move-in ready ranch-style home on a little more than a half acre. The matur...	2 beds \| 1 baths \| 960 sq.ft.	$245,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.36% Airbnb Rental Income: $956 Traditional Rental Income: $1452 Airbnb ROI: 0.71% Traditional ROI: 4.36%
125 Cheshire Ct Winchester, VA Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s...	4 beds \| 3 baths \| 2,261 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.63%
510 N Loudoun St Winchester, VA All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD...	5 beds \| N/A baths \| 2,376 sq.ft.	$419,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.69% Airbnb Rental Income: $867 Traditional Rental Income: $1444 Airbnb ROI: -0.52% Traditional ROI: 1.69%
189 Babbs Mountain Rd Winchester, VA Stunning 4 Bed / 3.5 Bath Chalet on 3.26 Acres with Over 6,300 Sq Ft - Minutes from Winche...	4 beds \| 3 baths \| 6,339 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.61% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 1.61%
157 Oak Dr Winchester, VA OPEN HOUSE SPECIAL! This weekend only, seller credit of $10,000 towards buyer closing cost...	4 beds \| 2 baths \| 2,280 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 3.51%
354 Valley Mill Rd Winchester, VA Two level townhome, Hardwood Floors * Huge Eat-In Kitchen * Full size Washer & Dryer * Dec...	2 beds \| 1 baths \| 1,200 sq.ft.	$274,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.72% Airbnb Rental Income: $956 Traditional Rental Income: $1232 Airbnb ROI: 0.3% Traditional ROI: 2.72%
407 Jefferson St Winchester, VA A TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling ...	3 beds \| 1 baths \| 2,805 sq.ft.	$464,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 4.62% Airbnb Rental Income: $1134 Traditional Rental Income: $2824 Airbnb ROI: -0.14% Traditional ROI: 4.62%
132 Amherst St Winchester, VA Charming Victorian home in the Heart of Historic downtown Winchester and located just off ...	4 beds \| 3 baths \| 3,474 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2922 Airbnb ROI: N/A Traditional ROI: 2.91%
129 Doonbeg Ct Winchester, VA ENJOY AN AFFORDABLE RETIREMENT! Newer, beautifully maintained 4-bedroom home with open flo...	4 beds \| 2 baths \| 2,072 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $2623 Airbnb ROI: N/A Traditional ROI: 3.99%
1105 Henry Dr Winchester, VA Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring throu...	4 beds \| 2 baths \| 2,850 sq.ft.	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.22%
2952 Grace St Winchester, VA Charming 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: 0.46% Traditional cash on cash: 2.93% Airbnb Rental Income: $1134 Traditional Rental Income: $1568 Airbnb ROI: 0.46% Traditional ROI: 2.93%
177 Dicks Hollow Rd Winchester, VA Newly remodeled 2-bedroom, 1-bath rancher just minutes from Winchester! This charming home...	2 beds \| 1 baths \| 650 sq.ft.	$245,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.96% Airbnb Rental Income: $956 Traditional Rental Income: $1301 Airbnb ROI: 0.97% Traditional ROI: 3.96%
511 Grouse Dr Winchester, VA Estimated completion March 2026 This is a fantastic opportunity to purchase a new cons...	3 beds \| 2 baths \| 1,333 sq.ft.	$304,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.55% Airbnb Rental Income: $1134 Traditional Rental Income: $1713 Airbnb ROI: 0.27% Traditional ROI: 3.55%
703 S Loudoun St Winchester, VA Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Ch...	3 beds \| 2 baths \| 1,992 sq.ft.	$484,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.43% Airbnb Rental Income: $1134 Traditional Rental Income: $2427 Airbnb ROI: -0.22% Traditional ROI: 3.43%
139 Biscane Ct Winchester, VA Welcome to 139 Biscane Ct., a beautiful townhome located in desirable Fieldstone community...	3 beds \| 3 baths \| 2,250 sq.ft.	$414,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.77% Airbnb Rental Income: $1134 Traditional Rental Income: $2228 Airbnb ROI: -0.02% Traditional ROI: 3.77%
247 Mcguire Rd Winchester, VA Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot...	4 beds \| 2 baths \| 2,894 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.58% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 1.58%
101 Delaware Trl Winchester, VA Welcome to 101 Delaware Trail, a thoughtfully updated home nestled in the highly desirable...	3 beds \| 2 baths \| 2,094 sq.ft.	$475,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.9% Airbnb Rental Income: $1134 Traditional Rental Income: $2053 Airbnb ROI: 0.12% Traditional ROI: 2.9%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$489,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.37%
129 Indiana Winchester, VA I am done! Large lot on private street with valley views and private. HW floors entire mai...	3 beds \| 2 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.31% Airbnb Rental Income: $1134 Traditional Rental Income: $2388 Airbnb ROI: -0.04% Traditional ROI: 4.31%
Lot 2 Tonto Trl Winchester, VA New Construction: 100% Hardwood - No Carpet! Move into this pristine 3-bed, 2.5-bath Colon...	3 beds \| 2 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.68% Airbnb Rental Income: $1134 Traditional Rental Income: $2529 Airbnb ROI: -0.04% Traditional ROI: 4.68%
1619 Tomahawk Trl Winchester, VA Discover the best value for square footage in this stunning 3 bed, 3 bath home. Perched on...	3 beds \| 3 baths \| 1,850 sq.ft.	$379,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.87% Airbnb Rental Income: $1134 Traditional Rental Income: $2474 Airbnb ROI: 0.05% Traditional ROI: 4.87%
126 Armstrong Pl Winchester, VA SHORT SALE: All brick ranch home with 4 bedrooms close to town and a short walk to the gol...	4 beds \| 3 baths \| 1,617 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $2603 Airbnb ROI: N/A Traditional ROI: 5.66%
376 CHARLES Street Winchester, VA Welcome to this charming Winchester home full of character and potential. Featuring a func...	3 beds \| 1 baths \| 1,232 sq.ft.	$185,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 6.34% Airbnb Rental Income: $1134 Traditional Rental Income: $1500 Airbnb ROI: 2.12% Traditional ROI: 6.34%
540 Monticello St Winchester, VA Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Dow...	9 beds \| 4 baths \| 4,396 sq.ft.	$605,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.94% Airbnb Rental Income: $867 Traditional Rental Income: $1529 Airbnb ROI: -0.82% Traditional ROI: 0.94%
181 Oak Dr Winchester, VA Very private community all paved road. Close to town with wooded lots 10 minutes to town. ...	N/A beds \| N/A baths \| 3,056 sq.ft.	$250,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 11.6% Airbnb Rental Income: $867 Traditional Rental Income: $3107 Airbnb ROI: 0.71% Traditional ROI: 11.6%
230 Tranquil Wood Ln Winchester, VA Are you in search of a spacious, one-level living home that combines privacy and the freed...	3 beds \| 2 baths \| 3,476 sq.ft.	$780,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 2.37% Airbnb Rental Income: $1134 Traditional Rental Income: $2570 Airbnb ROI: -0.13% Traditional ROI: 2.37%
129 Jalapa Trl Winchester, VA Close to Route 81 and 45 minutes to Metro to Dc, Buyer Credit - This beautifully tradition...	3 beds \| 2 baths \| 2,075 sq.ft.	$329,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.08% Airbnb Rental Income: $1134 Traditional Rental Income: $2400 Airbnb ROI: 0.45% Traditional ROI: 5.08%
2431 Cedar Creek Grade Winchester, VA This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/...	3 beds \| 1 baths \| 1,036 sq.ft.	$370,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.11% Airbnb Rental Income: $1134 Traditional Rental Income: $2331 Airbnb ROI: 0.58% Traditional ROI: 5.11%
1049 Laurel Grove Rd Winchester, VA This CUSTOM 3-bedroom, 3-bath home is sited on a private, wooded lot offering stunning mou...	3 beds \| 3 baths \| 2,112 sq.ft.	$767,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.85% Airbnb Rental Income: $1134 Traditional Rental Income: $2366 Airbnb ROI: -0.4% Traditional ROI: 1.85%

Real Estate investment in Winchester, VA

There are 325 properties for sale in the city of Winchester . The median list price in Winchester is $452,694 and the average price per square foot is $194. In March 2026, the average monthly cash on cash return in Winchester is 3.00%. The average monthly rental income in Winchester is $2,126.

Winchester, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 325 investment properties available for sale in Winchester.

In 2026, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $1,134.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

218 Flanagan Dr

Winchester, VA

4 beds | 4 baths | 4,354 sq.ft.

$642,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2975

Airbnb ROI: N/A

Traditional ROI: 2.91%

3466 Middle Rd

Winchester, VA

3 beds | 3 baths | 2,483 sq.ft.

$519,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1134

Traditional Rental Income: $2446

Airbnb ROI: -0.09%

Traditional ROI: 3.36%

127 Kinross Dr

Winchester, VA

5 beds | 3 baths | 3,494 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.83%

Airbnb Rental Income: $null

Traditional Rental Income: $3737

Airbnb ROI: N/A

Traditional ROI: 4.83%

152 DOE TRL

Winchester, VA

2 beds | 2 baths | N/A

$274,900

Airbnb cash on cash: 0.29%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $956

Traditional Rental Income: $1885

Airbnb ROI: 0.29%

Traditional ROI: 5.22%

369 Charles St

Winchester, VA

3 beds | 2 baths | 1,526 sq.ft.

$225,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 8.07%

Airbnb Rental Income: $1134

Traditional Rental Income: $2212

Airbnb ROI: 1.23%

Traditional ROI: 8.07%

1950 Melvor Ln

Winchester, VA

4 beds | 2 baths | 3,108 sq.ft.

$685,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2732

Airbnb ROI: N/A

Traditional ROI: 2.47%

519 Whitacre St

Winchester, VA

4 beds | 2 baths | 2,408 sq.ft.

$435,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2564

Airbnb ROI: N/A

Traditional ROI: 4.32%

832 Winder Ct

Winchester, VA

3 beds | 2 baths | 1,974 sq.ft.

$589,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1134

Traditional Rental Income: $2436

Airbnb ROI: -0.87%