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.

Condos for Sale in Winchester, VA

Search for Condo for Sale in Winchester, Virginia. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 4 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
140 Mccormick Cir #302 Winchester, VA Welcome home to this gorgeous, like-new condo located in scenic and historic Winchester! T...	2 beds \| 2 baths \| 1,156 sq.ft.	$314,900	Airbnb cash on cash: -0.18% Traditional cash on cash: 5.17% Airbnb Rental Income: $956 Traditional Rental Income: $2193 Airbnb ROI: -0.18% Traditional ROI: 5.17%
140 Mccormick Cir #403 Winchester, VA Motivated Sellers! Bring all offers. Nearly-new 55+ condominium located in Winchester Land...	2 beds \| 2 baths \| 1,156 sq.ft.	$305,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 4.98% Airbnb Rental Income: $956 Traditional Rental Income: $2125 Airbnb ROI: -0.3% Traditional ROI: 4.98%
151 Mccormick Cir #201 Winchester, VA Price improvement!! Experience Effortless 55+ Living at Winchester Landing - The Sapphire ...	2 beds \| 2 baths \| 1,554 sq.ft.	$385,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 3.65% Airbnb Rental Income: $956 Traditional Rental Income: $2334 Airbnb ROI: -1.13% Traditional ROI: 3.65%
151 Mccormick #203 Winchester, VA Welcome to Winchester Landing, a 55+ condominium community offering comfort, convenience, ...	2 beds \| 2 baths \| 1,156 sq.ft.	$311,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.72% Airbnb Rental Income: $956 Traditional Rental Income: $2161 Airbnb ROI: -0.59% Traditional ROI: 4.72%
Other Investment Properties for Sale in Winchester
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%
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%

Your search for investment property begins and ends here

Condos for Sale in Winchester, VA

140 Mccormick Cir #302

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$314,900

Airbnb cash on cash: -0.18%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $956

Traditional Rental Income: $2193

Airbnb ROI: -0.18%

Traditional ROI: 5.17%

140 Mccormick Cir #403

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$305,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $956

Traditional Rental Income: $2125

Airbnb ROI: -0.3%

Traditional ROI: 4.98%

151 Mccormick Cir #201

Winchester, VA

2 beds | 2 baths | 1,554 sq.ft.

$385,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $956

Traditional Rental Income: $2334

Airbnb ROI: -1.13%

Traditional ROI: 3.65%

151 Mccormick #203

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$311,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $956

Traditional Rental Income: $2161

Airbnb ROI: -0.59%

Traditional ROI: 4.72%

Other Investment Properties for Sale in Winchester

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%

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%

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%

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%

Winchester , VA

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