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
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: 2.34% Airbnb Rental Income: $1134 Traditional Rental Income: $1995 Airbnb ROI: -0.16% Traditional ROI: 2.34%
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%
162 JANES Way Winchester, VA Discover this beautifully updated home on 5 private acres in the sought-after Brookneill S...	4 beds \| 4 baths \| 4,461 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $3435 Airbnb ROI: N/A Traditional ROI: 2.99%
157 OAK Drive Winchester, VA Welcome home to 157 Oak Dr. in Winchester, VA-an inviting property offering comfort, thoug...	4 beds \| 3 baths \| 2,280 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 2.78%
236 MILLER Street Winchester, VA New roof and HVAC system (2022) Charming 3-Bedroom/ 2.5 Bath with a garage! Only blocks fr...	3 beds \| 3 baths \| 1,978 sq.ft.	$475,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.88% Airbnb Rental Income: $1134 Traditional Rental Income: $2602 Airbnb ROI: -0.27% Traditional ROI: 3.88%
204 SHENANDOAH Avenue Winchester, VA Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes...	2 beds \| 1 baths \| 882 sq.ft.	$265,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.17% Airbnb Rental Income: $956 Traditional Rental Income: $1541 Airbnb ROI: 0.44% Traditional ROI: 4.17%
132 AMHERST Street Winchester, VA Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a tr...	4 beds \| 4 baths \| 3,475 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2922 Airbnb ROI: N/A Traditional ROI: 2.64%
129 DOONBEG Court Winchester, VA ENJOY AN AFFORDABLE RETIREMENT! Newer, beautifully maintained 4-bedroom home with open flo...	4 beds \| 3 baths \| 2,072 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $2623 Airbnb ROI: N/A Traditional ROI: 4.06%
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.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.19%
126 N EUCLID Avenue Winchester, VA Discover this charming brick home that offers a perfect blend of classic character and mod...	4 beds \| 3 baths \| 1,868 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2111 Airbnb ROI: N/A Traditional ROI: 4.12%
511 GROUSE Drive Winchester, VA This is a fantastic opportunity to purchase a new construction home and have the ability t...	3 beds \| 2 baths \| 1,333 sq.ft.	$309,900	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%
681 HILLMAN Drive Winchester, VA No HOA and only two years young, this beautifully designed and meticulously maintained hom...	5 beds \| 4 baths \| 3,550 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3163 Airbnb ROI: N/A Traditional ROI: 3.75%
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 \| 3 baths \| 1,660 sq.ft.	$379,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.62% Airbnb Rental Income: $1134 Traditional Rental Income: $2388 Airbnb ROI: 0.05% Traditional ROI: 4.62%
126 ARMSTRONG Place 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%
355 FISHEL Road Winchester, VA Experience the epitome of homeownership with this stunning colonial home property perfectl...	3 beds \| 4 baths \| 3,008 sq.ft.	$669,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.54% Airbnb Rental Income: $1134 Traditional Rental Income: $3174 Airbnb ROI: -0.33% Traditional ROI: 3.54%
129 JALAPA Trail Winchester, VA Buyer Credit - This beautifully traditional home in Winchester, it offers a perfect blend ...	3 beds \| 2 baths \| 2,075 sq.ft.	$399,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.78% Airbnb Rental Income: $1134 Traditional Rental Income: $2400 Airbnb ROI: 0.38% Traditional ROI: 4.78%
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 \| N/A	$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%
1412 MAGRUDER COURT Winchester, VA Finally, an all-brick, very well-maintained home in The Downs of Meadow Branch. Just shut ...	3 beds \| 2 baths \| 2,154 sq.ft.	$569,900	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.69% Airbnb Rental Income: $1134 Traditional Rental Income: $2165 Airbnb ROI: -0.95% Traditional ROI: 1.69%
21 W PALL MALL Street Winchester, VA This inviting Winchester home offers a comfortable blend of character, functionality, and ...	4 beds \| 3 baths \| 1,634 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $1776 Airbnb ROI: N/A Traditional ROI: 2.4%
114 NASSAU Drive Winchester, VA 4 bed/ 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. ...	4 beds \| 4 baths \| 3,829 sq.ft.	$559,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $3215 Airbnb ROI: N/A Traditional ROI: 4.41%
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%
421 SUPERIOR AVE Winchester, VA Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt drivew...	3 beds \| 2 baths \| 1,800 sq.ft.	$441,700	Airbnb cash on cash: 0.05% Traditional cash on cash: 3.52% Airbnb Rental Income: $1134 Traditional Rental Income: $2192 Airbnb ROI: 0.05% Traditional ROI: 3.52%
711 E CORK Street Winchester, VA This stunning property boasts a brand-new kitchen with quartz countertops, new appliances ...	2 beds \| 2 baths \| 1,186 sq.ft.	$384,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.93% Airbnb Rental Income: $956 Traditional Rental Income: $2085 Airbnb ROI: -0.16% Traditional ROI: 3.93%
553 HIGHLAND Avenue Winchester, VA Don't miss taking a LOOK at this property with the new low price of $319K. One Way street ...	3 beds \| 2 baths \| 1,362 sq.ft.	$319,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.52% Airbnb Rental Income: $1134 Traditional Rental Income: $2164 Airbnb ROI: 0.83% Traditional ROI: 5.52%
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%
769 SELDON Drive Winchester, VA Welcome to 769 Seldon Drive-an elegant brick-front colonial situated on nearly half an acr...	5 beds \| 5 baths \| 4,438 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $4891 Airbnb ROI: N/A Traditional ROI: 4.1%
323 RUSSELCROFT Road Winchester, VA Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living ...	4 beds \| 2 baths \| 1,534 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: 5.19%

Real Estate investment in Winchester, VA

There are 104 properties for sale in the city of Winchester . The median list price in Winchester is $382,400 and the average price per square foot is $189. In January 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,321.

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

There are 104 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

701 HICKORY Trail

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%

534 N KENT Street

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%

3466 MIDDLE RD

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%

219 MILAM Drive

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%

369 CHARLES Street

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 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

Traditional ROI: 2.47%

330 W CECIL Street

Winchester, VA

3 beds | 2 baths | 1,820 sq.ft.

$529,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $1134

Traditional Rental Income: $1995

Airbnb ROI: -0.16%

Traditional ROI: 2.34%

126 PLAINFIELD Drive

Winchester, VA

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