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.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
140 MCCORMICK Circle unit: 302 #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: -0.48% Traditional cash on cash: 4.87% Airbnb Rental Income: $956 Traditional Rental Income: $2193 Airbnb ROI: -0.48% Traditional ROI: 4.87%
140 MCCORMICK Circle unit: 403 #403 Winchester, VA Motivated Sellers! Bring all offers. Nearly-new 55+ condominium located in Winchester Land...	2 beds \| 2 baths \| 1,156 sq.ft.	$315,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.7% Airbnb Rental Income: $956 Traditional Rental Income: $2125 Airbnb ROI: 0.58% Traditional ROI: 5.7%
157 BROOKLAND TERRACE unit: 11 #11 Winchester, VA Top-Floor Gem with Vaulted Ceilings, Modern Upgrades & Quick Seller Move-Out! Welcome home...	2 beds \| 2 baths \| 1,173 sq.ft.	$235,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 6.82% Airbnb Rental Income: $956 Traditional Rental Income: $1928 Airbnb ROI: 0.88% Traditional ROI: 6.82%
115-12 BROOKLAND Terrace unit: 12 #12 Winchester, VA Ready for Occupancy-Penthouse condo in excellent condition The cathedral ceilings and skyl...	2 beds \| 2 baths \| 1,173 sq.ft.	$250,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 6.73% Airbnb Rental Income: $956 Traditional Rental Income: $2016 Airbnb ROI: 0.77% Traditional ROI: 6.73%
Other Investment Properties for Sale in Winchester
701 HICKORY Trail Winchester , VA Newer construction colonial in the Shawneeland community offering 3 bedrooms, 2.5 baths, a...	3 beds \| 3 baths \| 1,660 sq.ft.	$365,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.11% Airbnb Rental Income: $1134 Traditional Rental Income: $1995 Airbnb ROI: 0.49% Traditional ROI: 4.11%
534 N KENT Street Winchester , VA Just minutes from the downtown walking mall, this single family home offers three bedrooms...	3 beds \| 2 baths \| 1,152 sq.ft.	$295,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 5.34% Airbnb Rental Income: $1134 Traditional Rental Income: $2073 Airbnb ROI: 0.6% Traditional ROI: 5.34%
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 \| N/A	$529,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.32% Airbnb Rental Income: $1134 Traditional Rental Income: $2446 Airbnb ROI: -0.09% Traditional ROI: 3.32%
219 MILAM Drive Winchester , VA Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet nei...	4 beds \| 3 baths \| 2,654 sq.ft.	$467,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.46% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 5.46%
369 CHARLES Street 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 Lane Winchester , VA Step into this meticulously maintained colonial home, a testament to quality craftsmanship...	4 beds \| 3 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%
330 W CECIL Street Winchester , VA The perfect Downtown Winchester location! Welcome to this charming brick Colonial in the h...	3 beds \| 2 baths \| 1,820 sq.ft.	$529,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.04% Airbnb Rental Income: $1134 Traditional Rental Income: $2341 Airbnb ROI: -0.16% Traditional ROI: 3.04%
519 WHITACRE Street Winchester , VA This spacious split-level home offers a versatile layout with multiple living areas, provi...	4 beds \| 2 baths \| 2,408 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 3.8%
126 PLAINFIELD Drive Winchester , VA Live in town on south end with a viable yard with two sheds, 4 bedrooms, some simple updat...	4 beds \| 2 baths \| 1,456 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $2350 Airbnb ROI: N/A Traditional ROI: 5.9%
199 MEETING HOUSE Drive Winchester , VA Legendary Living on 3.46 Acres - 5BR Estate With Mountain Views, Luxe Updates & Iconic His...	5 beds \| 5 baths \| 3,767 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $4682 Airbnb ROI: N/A Traditional ROI: 4.48%
163 DENNY Lane Winchester , VA Saturdauy, January 4pm-6pm and Sunday, January 18th 11am-1pm. Excellent outdoor workspace ...	3 beds \| 2 baths \| 1,152 sq.ft.	$339,990	Airbnb cash on cash: 0.7% Traditional cash on cash: 5.14% Airbnb Rental Income: $1134 Traditional Rental Income: $2173 Airbnb ROI: 0.7% Traditional ROI: 5.14%
815 PHEASANT Drive 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: 0.66% Traditional cash on cash: 4.3% Airbnb Rental Income: $956 Traditional Rental Income: $1452 Airbnb ROI: 0.66% Traditional ROI: 4.3%
147 HARVEST RIDGE Drive Winchester , VA NEW HVAC system 2026! Main level system replaced in January. New Roof in 2023. Quick closi...	3 beds \| 3 baths \| 3,153 sq.ft.	$639,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.64% Airbnb Rental Income: $1134 Traditional Rental Income: $2734 Airbnb ROI: -0.67% Traditional ROI: 2.64%
125 CHESHIRE Court Winchester , VA Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s...	4 beds \| 4 baths \| 2,261 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.67%
242 FOOTSTONE Lane Winchester , VA Peaceful Country Retreat on 4.7 Acres - Minutes from Winchester This private country home ...	1 beds \| 1 baths \| 1,348 sq.ft.	$319,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.86% Airbnb Rental Income: $842 Traditional Rental Income: $1669 Airbnb ROI: 0% Traditional ROI: 3.86%

Your search for investment property begins and ends here

Condos for Sale in Winchester, VA

140 MCCORMICK Circle unit: 302 #302

Winchester, VA

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

$314,900

Airbnb cash on cash: -0.48%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $956

Traditional Rental Income: $2193

Airbnb ROI: -0.48%

Traditional ROI: 4.87%

140 MCCORMICK Circle unit: 403 #403

Winchester, VA

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

$315,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 5.7%

Airbnb Rental Income: $956

Traditional Rental Income: $2125

Airbnb ROI: 0.58%

Traditional ROI: 5.7%

157 BROOKLAND TERRACE unit: 11 #11

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$235,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 6.82%

Airbnb Rental Income: $956

Traditional Rental Income: $1928

Airbnb ROI: 0.88%

Traditional ROI: 6.82%

115-12 BROOKLAND Terrace unit: 12 #12

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$250,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $956

Traditional Rental Income: $2016

Airbnb ROI: 0.77%

Traditional ROI: 6.73%

Other Investment Properties for Sale in Winchester

Winchester , VA

3 beds | 3 baths | 1,660 sq.ft.

$365,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $1134

Traditional Rental Income: $1995

Airbnb ROI: 0.49%

Traditional ROI: 4.11%

Winchester , VA

3 beds | 2 baths | 1,152 sq.ft.

$295,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $1134

Traditional Rental Income: $2073

Airbnb ROI: 0.6%

Traditional ROI: 5.34%

Winchester , VA

3 beds | 3 baths | N/A

$529,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1134

Traditional Rental Income: $2446

Airbnb ROI: -0.09%

Traditional ROI: 3.32%

Winchester , VA

4 beds | 3 baths | 2,654 sq.ft.

$467,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3073

Airbnb ROI: N/A

Traditional ROI: 5.46%

Winchester , VA

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