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
802 Chesley Street Winchester, VA This brand-new construction nestled in an established neighborhood offers the perfect blen...	3 beds \| 2 baths \| 1,730 sq.ft.	$380,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.81% Airbnb Rental Income: $3564 Traditional Rental Income: $2164 Airbnb ROI: 5.54% Traditional ROI: 3.81%
798 Chesley Street Winchester, VA This brand-new construction nestled in an established neighborhood offers the perfect blen...	3 beds \| 2 baths \| 1,730 sq.ft.	$380,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 4.29% Airbnb Rental Income: $3564 Traditional Rental Income: $2334 Airbnb ROI: 5.54% Traditional ROI: 4.29%
12481 SUPINLICK RIDGE RD Winchester, VA Charming 1940 Custom Home with Unique Features on 4 Acres near Bryce Resort Step into hist...	3 beds \| 2 baths \| 879 sq.ft.	$449,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 3.26% Airbnb Rental Income: $3564 Traditional Rental Income: $1978 Airbnb ROI: 5.17% Traditional ROI: 3.26%
3118 Mitchells Mill Road Winchester, VA Beautiful new Ranch home with 3 bedrooms and 2 full baths on 12 acres with pond access, vi...	3 beds \| 2 baths \| 1,400 sq.ft.	$369,950	Airbnb cash on cash: 6.2% Traditional cash on cash: 4.78% Airbnb Rental Income: $3564 Traditional Rental Income: $2287 Airbnb ROI: 6.2% Traditional ROI: 4.78%
Investment Properties for Sale in Other Cities of Virginia
1700 CLARENDON BLVD #153 Arlington , VA Huge Price Reduction - Now Priced Below $1 Million! Seize this rare opportunity to own a ...	2 beds \| 2 baths \| N/A	$999,999	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.8% Airbnb Rental Income: $3824 Traditional Rental Income: $2692 Airbnb ROI: 1.13% Traditional ROI: 0.8%
2711 E Clay Street Richmond , VA A Charming Historic Home in the Heart of Church Hill! Welcome to this delightful home bri...	2 beds \| 2 baths \| 960 sq.ft.	$350,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.03% Airbnb Rental Income: $2251 Traditional Rental Income: $1785 Airbnb ROI: 2.73% Traditional ROI: 3.03%
4005 Atlantic Avenue #217 Virginia Beach , VA Nestled within the Oceans II Condo community, this exceptional unit is more than just a be...	1 beds \| 1 baths \| 300 sq.ft.	$375,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.28% Airbnb Rental Income: $1539 Traditional Rental Income: $1503 Airbnb ROI: 0.12% Traditional ROI: 1.28%
105 Wentworth Williamsburg , VA Introducing an exceptional home in the prestigious Fords Colony! This remarkable residence...	4 beds \| 3 baths \| 4,100 sq.ft.	$974,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.67% Airbnb Rental Income: $4092 Traditional Rental Income: $3103 Airbnb ROI: 1.8% Traditional ROI: 1.67%
1233 STUART ROBESON DRIVE McLean , VA Nestled in sought after -MERRYHILL- this Georgian style Flemish bond brick residence exude...	3 beds \| 6 baths \| 5,821 sq.ft.	$2,500,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 0.15% Airbnb Rental Income: $5659 Traditional Rental Income: $5843 Airbnb ROI: -0.42% Traditional ROI: 0.15%
201 N New Avenue Highland Springs , VA Great opportunity for rental or first time home owner. This home offers 3 bedrooms, 2 bat...	3 beds \| 2 baths \| 1,319 sq.ft.	$254,000	Airbnb cash on cash: 8.19% Traditional cash on cash: 6.39% Airbnb Rental Income: $3220 Traditional Rental Income: $2062 Airbnb ROI: 8.19% Traditional ROI: 6.39%
3012 Estates Lane Portsmouth , VA Enjoy easy living in this end unit condo with 2 car garage in The Villas at River Pointe g...	3 beds \| 3 baths \| 1,742 sq.ft.	$275,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.64% Airbnb Rental Income: $2358 Traditional Rental Income: $2113 Airbnb ROI: 3.34% Traditional ROI: 4.64%
2226 Monument Avenue Richmond , VA Looking for a move-in ready luxury home in the Fan? Welcome to this finely renovated and r...	4 beds \| 5 baths \| 4,339 sq.ft.	$1,995,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 0.52% Airbnb Rental Income: $7281 Traditional Rental Income: $4704 Airbnb ROI: 1.16% Traditional ROI: 0.52%
4402 Brook Road Richmond , VA Welcome to 4402 Brook Rd, a whimsical and charming 3-bedroom, 1.5-bathroom Tudor-style cot...	3 beds \| 2 baths \| 1,344 sq.ft.	$435,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 3.19% Airbnb Rental Income: $3960 Traditional Rental Income: $2142 Airbnb ROI: 5.57% Traditional ROI: 3.19%
7409 Red Hill Club Court Richmond , VA Best value in Settlers Ridge's 55+ community of homes. Enjoy this wonderful 2 bedroom 2 ba...	2 beds \| 2 baths \| 1,396 sq.ft.	$325,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 3.38% Airbnb Rental Income: $3384 Traditional Rental Income: $2021 Airbnb ROI: 5.38% Traditional ROI: 3.38%
665 Fairfax Way Williamsburg , VA This beautifully maintained Colonial home is located in the desirable Kingsmill community....	4 beds \| 5 baths \| 3,421 sq.ft.	$675,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 5.03% Airbnb Rental Income: $4092 Traditional Rental Income: $4527 Airbnb ROI: 2.95% Traditional ROI: 5.03%
4704 Lady Slipper Path Williamsburg , VA Great home & location. Graylin Woods is a highly desirable neighborhood offering nature &...	3 beds \| 2 baths \| 1,870 sq.ft.	$476,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 3.15% Airbnb Rental Income: $2563 Traditional Rental Income: $2236 Airbnb ROI: 2.5% Traditional ROI: 3.15%
8772 Marlfield Road Gloucester , VA Compact home but gives you everything you need is just north of Gloucester Courthouse. Gre...	3 beds \| 2 baths \| 1,058 sq.ft.	$264,900	Airbnb cash on cash: 6.21% Traditional cash on cash: 5.73% Airbnb Rental Income: $2640 Traditional Rental Income: $1890 Airbnb ROI: 6.21% Traditional ROI: 5.73%
108 Spindrift Road White Stone , VA "Gray Stone" is an exquisite French Provincial/Georgian home in area of upscale homes near...	4 beds \| 5 baths \| 4,065 sq.ft.	$1,150,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.98% Airbnb Rental Income: $4922 Traditional Rental Income: $4904 Airbnb ROI: 2.05% Traditional ROI: 2.98%
12000 MARKET STREET #145 Reston , VA Welcome to this beautiful move-in ready 1-bedroom, 1-bath condo at The Savoy. Featuring hi...	1 beds \| 1 baths \| 754 sq.ft.	$350,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 4.19% Airbnb Rental Income: $2555 Traditional Rental Income: $2148 Airbnb ROI: 3.56% Traditional ROI: 4.19%

Real Estate investment in Winchester, VA

There are 4 properties for sale in the city of Winchester . The median list price in Winchester is $419,900 and the average price per square foot is $185. In December 2024, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,344.

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

There are 4 investment properties available for sale in Winchester.

In 2024, 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 $3,564.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

802 Chesley Street

Winchester, VA

3 beds | 2 baths | 1,730 sq.ft.

$380,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $3564

Traditional Rental Income: $2164

Airbnb ROI: 5.54%

Traditional ROI: 3.81%

798 Chesley Street

Winchester, VA

3 beds | 2 baths | 1,730 sq.ft.

$380,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $3564

Traditional Rental Income: $2334

Airbnb ROI: 5.54%

Traditional ROI: 4.29%

12481 SUPINLICK RIDGE RD

Winchester, VA

3 beds | 2 baths | 879 sq.ft.

$449,900

Airbnb cash on cash: 5.17%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $3564

Traditional Rental Income: $1978

Airbnb ROI: 5.17%

Traditional ROI: 3.26%

3118 Mitchells Mill Road

Winchester, VA

3 beds | 2 baths | 1,400 sq.ft.

$369,950

Airbnb cash on cash: 6.2%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3564

Traditional Rental Income: $2287

Airbnb ROI: 6.2%

Traditional ROI: 4.78%

Investment Properties for Sale in Other Cities of Virginia

Arlington , VA

2 beds | 2 baths | N/A

$999,999

Airbnb cash on cash: 1.13%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $3824

Traditional Rental Income: $2692

Airbnb ROI: 1.13%

Traditional ROI: 0.8%

Richmond , VA

2 beds | 2 baths | 960 sq.ft.

$350,000

Airbnb cash on cash: 2.73%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2251

Traditional Rental Income: $1785

Airbnb ROI: 2.73%

Traditional ROI: 3.03%

Virginia Beach , VA

1 beds | 1 baths | 300 sq.ft.

$375,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $1539

Traditional Rental Income: $1503

Airbnb ROI: 0.12%

Traditional ROI: 1.28%

Williamsburg , VA

4 beds | 3 baths | 4,100 sq.ft.

$974,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $4092

Traditional Rental Income: $3103

Airbnb ROI: 1.8%

Traditional ROI: 1.67%

McLean , VA

3 beds | 6 baths | 5,821 sq.ft.