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.

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winchester, VA

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

Showing 199 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential 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
2643 MIDDLE Road Winchester, VA Location Location Location! NO HOA!!! Hardwood floors on the main level. Formal living and...	4 beds \| 4 baths \| 2,524 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.52% Airbnb Rental Income: $null Traditional Rental Income: $3058 Airbnb ROI: N/A Traditional ROI: 4.52%
719 Smithfield Avenue Winchester, VA Bringing all the bungalow love! This 2 bed/1 bath home is move-in ready after a 2025 Refre...	2 beds \| 1 baths \| 720 sq.ft.	$275,000	Airbnb cash on cash: 6.38% Traditional cash on cash: 3.74% Airbnb Rental Income: $2689 Traditional Rental Income: $1368 Airbnb ROI: 6.38% Traditional ROI: 3.74%
3466 MIDDLE RD Winchester, VA Welcome 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: 0.35% Traditional cash on cash: 3.67% Airbnb Rental Income: $1337 Traditional Rental Income: $2446 Airbnb ROI: 0.35% Traditional ROI: 3.67%
108 NORFOLK Court Winchester, VA Welcome to 108 Norfolk Court in Winchester, where luxury, comfort, and an impressive amoun...	4 beds \| 5 baths \| 5,020 sq.ft.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $4402 Airbnb ROI: N/A Traditional ROI: 5.15%
171 LAUREL GROVE Road Winchester, VA Historic 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: -0.16% Traditional cash on cash: 3.19% Airbnb Rental Income: $1337 Traditional Rental Income: $3189 Airbnb ROI: -0.16% Traditional ROI: 3.19%
127 KINROSS Drive Winchester, VA A 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 Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 5.07%
110 MEADOWVIEW Court Winchester, VA Ready for new owners, this welllocated home on Winchester's east side offers commuter conv...	4 beds \| 3 baths \| 1,680 sq.ft.	$364,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2364 Airbnb ROI: N/A Traditional ROI: 5.19%
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%
1851 MELVOR Lane Winchester, VA Extremely 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: 3.08% Traditional cash on cash: 1.74% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 3.08% Traditional ROI: 1.74%
145 Graywolf Trail Winchester, VA Looking for privacy, modern finishes, and a extra lot? This 2021-built Colonial checks all...	3 beds \| 3 baths \| 1,660 sq.ft.	$375,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.54% Airbnb Rental Income: $1337 Traditional Rental Income: $2327 Airbnb ROI: 0.55% Traditional ROI: 4.54%
832 WINDER Court 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.	$550,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 2.41% Airbnb Rental Income: $1337 Traditional Rental Income: $2436 Airbnb ROI: -0.53% Traditional ROI: 2.41%
610 PUMA Trail Winchester, VA Tucked 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: 7.7% Traditional cash on cash: 4.09% Airbnb Rental Income: $2689 Traditional Rental Income: $1284 Airbnb ROI: 7.7% Traditional ROI: 4.09%
540 Eagle Place Winchester, VA Welcome to this well-maintained one-level rancher tucked away in a quiet cul-de-sac. This ...	3 beds \| 2 baths \| 1,450 sq.ft.	$385,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.41% Airbnb Rental Income: $1337 Traditional Rental Income: $2263 Airbnb ROI: 0.71% Traditional ROI: 4.41%
157 OAK Drive Winchester, VA STOP 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 Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 4.06%
321 COPPERFIELD Lane Winchester, VA Super cute 3 level townhome with a great design, two full baths one in the basement one in...	3 beds \| 3 baths \| 1,840 sq.ft.	$315,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 5.69% Airbnb Rental Income: $1337 Traditional Rental Income: $2394 Airbnb ROI: 0.73% Traditional ROI: 5.69%
132 AMHERST Street Winchester, VA Charming 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 Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2922 Airbnb ROI: N/A Traditional ROI: 2.91%
129 DOONBEG Court Winchester, VA ENJOY 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 Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $2623 Airbnb ROI: N/A Traditional ROI: 3.99%
1105 HENRY Drive Winchester, VA Home 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 Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.36%
317 GRAY Avenue Winchester, VA Welcome 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 Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $1909 Airbnb ROI: N/A Traditional ROI: 3.49%
177 DICKS HOLLOW Road Winchester, VA Newly remodeled turn-key starter home with modern updates. 2-bedroom 1-bathroom rancher ju...	2 beds \| 1 baths \| 650 sq.ft.	$245,000	Airbnb cash on cash: 7.21% Traditional cash on cash: 3.96% Airbnb Rental Income: $2689 Traditional Rental Income: $1301 Airbnb ROI: 7.21% Traditional ROI: 3.96%
174 WILLIAMSON Road Winchester, VA If you want more space and are priced out of Northern Virginia, come to Winchester! If you...	5 beds \| 4 baths \| 4,008 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.21% Airbnb Rental Income: $null Traditional Rental Income: $2770 Airbnb ROI: N/A Traditional ROI: 2.21%
511 GROUSE Drive Winchester, 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: 0.89% Traditional cash on cash: 3.64% Airbnb Rental Income: $1337 Traditional Rental Income: $1713 Airbnb ROI: 0.89% Traditional ROI: 3.64%
25 W SOUTHWERK Street Winchester, VA Welcome 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: 0.57% Traditional cash on cash: 2.08% Airbnb Rental Income: $1337 Traditional Rental Income: $1558 Airbnb ROI: 0.57% Traditional ROI: 2.08%
105 AMBERFIELD Court Winchester, VA Move in Ready!!! Nestled in the serene enclave of Abram's Chase and located within minutes...	2 beds \| 2 baths \| 1,800 sq.ft.	$529,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.01% Airbnb Rental Income: $2689 Traditional Rental Income: $1949 Airbnb ROI: 2.22% Traditional ROI: 2.01%
703 S LOUDOUN Street Winchester, VA Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Ch...	3 beds \| 3 baths \| 1,992 sq.ft.	$479,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.52% Airbnb Rental Income: $1337 Traditional Rental Income: $2427 Airbnb ROI: 0.18% Traditional ROI: 3.52%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winchester, VA

2643 MIDDLE Road

Winchester, VA

4 beds | 4 baths | 2,524 sq.ft.

$500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.52%

Airbnb Rental Income: $null

Traditional Rental Income: $3058

Airbnb ROI: N/A

Traditional ROI: 4.52%

719 Smithfield Avenue

Winchester, VA

2 beds | 1 baths | 720 sq.ft.

$275,000

Airbnb cash on cash: 6.38%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2689

Traditional Rental Income: $1368

Airbnb ROI: 6.38%

Traditional ROI: 3.74%

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$489,999

Airbnb cash on cash: 0.35%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1337

Traditional Rental Income: $2446

Airbnb ROI: 0.35%

Traditional ROI: 3.67%

108 NORFOLK Court

Winchester, VA

4 beds | 5 baths | 5,020 sq.ft.

$689,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.15%

Airbnb Rental Income: $null

Traditional Rental Income: $4402

Airbnb ROI: N/A

Traditional ROI: 5.15%

171 LAUREL GROVE Road

Winchester, VA

3 beds | 3 baths | 3,052 sq.ft.

$725,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1337

Traditional Rental Income: $3189

Airbnb ROI: -0.16%

Traditional ROI: 3.19%

127 KINROSS Drive

Winchester, VA

5 beds | 4 baths | 3,494 sq.ft.

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.07%

Airbnb Rental Income: $null

Traditional Rental Income: $3737

Airbnb ROI: N/A

Traditional ROI: 5.07%

110 MEADOWVIEW Court

Winchester, VA

4 beds | 3 baths | 1,680 sq.ft.

$364,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2364

Airbnb ROI: N/A

Traditional ROI: 5.19%

1950 MELVOR Lane

Winchester, VA

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