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: 5.25% Airbnb Rental Income: $1134 Traditional Rental Income: $2386 Airbnb ROI: 0.49% Traditional ROI: 5.25%
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%
1610 S LOUDOUN Street Winchester, VA Welcome to this charming Cape Cod located in the heart of Winchester. Centrally situated j...	4 beds \| 2 baths \| 1,344 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $2207 Airbnb ROI: N/A Traditional ROI: 5.6%
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%
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.	$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: 3.9% Airbnb Rental Income: $956 Traditional Rental Income: $1544 Airbnb ROI: 0.29% Traditional ROI: 3.9%
105 W OATES Avenue Winchester, VA This beautifully updated and lovingly maintained home is located in the much loved heart o...	3 beds \| 2 baths \| 1,066 sq.ft.	$345,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.57% Airbnb Rental Income: $1134 Traditional Rental Income: $2075 Airbnb ROI: 0.5% Traditional ROI: 4.57%
156 SOLARA Drive Winchester, VA Showstopper Custom Townhouse on Winchester's Sought-After East Side. This exceptional thre...	4 beds \| 4 baths \| 2,281 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $2848 Airbnb ROI: N/A Traditional ROI: 5.29%
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%
110 RUGBY Place Winchester, VA Welcome to 110 Rugby-a striking 3-bedroom, 2.5-bath home designed with space, style, and m...	3 beds \| 3 baths \| 1,625 sq.ft.	$450,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.89% Airbnb Rental Income: $1134 Traditional Rental Income: $2358 Airbnb ROI: 0.09% Traditional ROI: 3.89%
519 WHITACRE Street Winchester, VA Ideally located within one of Winchester's most desirable neighborhoods, Whittier Acres, a...	4 beds \| 2 baths \| 2,408 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $2564 Airbnb ROI: N/A Traditional ROI: 4.26%
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.	$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 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%
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: 0.71% Traditional cash on cash: 4.36% Airbnb Rental Income: $956 Traditional Rental Income: $1452 Airbnb ROI: 0.71% Traditional ROI: 4.36%
125 CHESHIRE 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: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.63%
510 N LOUDOUN Street Winchester, VA All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD...	N/A beds \| N/A baths \| 2,376 sq.ft.	$449,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.63% Airbnb Rental Income: $867 Traditional Rental Income: $1444 Airbnb ROI: -0.53% Traditional ROI: 1.63%
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: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 3.51%
407 JEFFERSON Street Winchester, VA ON SALE! Your PERFECT TURN KEY classic colonial, fully UPDATED, and PHENOMENALLY LOCATED! ...	3 beds \| 3 baths \| 2,805 sq.ft.	$476,500	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.47% Airbnb Rental Income: $1134 Traditional Rental Income: $2824 Airbnb ROI: -0.17% Traditional ROI: 4.47%
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: 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.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.15%
2952 GRACE Street Winchester, VA Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winch...	3 beds \| 1 baths \| 960 sq.ft.	$359,900	Airbnb cash on cash: 0.42% Traditional cash on cash: 2.82% Airbnb Rental Income: $1134 Traditional Rental Income: $1568 Airbnb ROI: 0.42% Traditional ROI: 2.82%
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 Estimated completion March 2026 This is a fantastic opportunity to purchase a new cons...	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%
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.	$489,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.49% Airbnb Rental Income: $1134 Traditional Rental Income: $1995 Airbnb ROI: -0.22% Traditional ROI: 2.49%
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.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $3163 Airbnb ROI: N/A Traditional ROI: 4.18%
247 MCGUIRE Road Winchester, VA Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot...	4 beds \| 3 baths \| 2,894 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.58% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 1.58%
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%
TONTO Trail lot: 2 Winchester, VA New Construction: 100% Hardwood - No Carpet! Move into this pristine 3-bed, 2.5-bath Colon...	3 beds \| 3 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.68% Airbnb Rental Income: $1134 Traditional Rental Income: $2529 Airbnb ROI: -0.04% Traditional ROI: 4.68%
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%
230 TRANQUIL WOOD Lane Winchester, VA Are you in search of a spacious, one-level living home that combines privacy and the freed...	3 beds \| 3 baths \| 3,476 sq.ft.	$790,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.33% Airbnb Rental Income: $1134 Traditional Rental Income: $2570 Airbnb ROI: -0.14% Traditional ROI: 2.33%
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 Close to Route 81 and 45 minutes to Metro to Dc, Buyer Credit - This beautifully tradition...	3 beds \| 2 baths \| 2,075 sq.ft.	$379,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.08% Airbnb Rental Income: $1134 Traditional Rental Income: $2400 Airbnb ROI: 0.45% Traditional ROI: 5.08%
2431 CEDAR CREEK Grade Winchester, VA This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/...	3 beds \| 2 baths \| 1,036 sq.ft.	$370,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.11% Airbnb Rental Income: $1134 Traditional Rental Income: $2331 Airbnb ROI: 0.58% Traditional ROI: 5.11%
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%

Real Estate investment in Winchester, VA

There are 149 properties for sale in the city of Winchester . The median list price in Winchester is $412,500 and the average price per square foot is $199. In February 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,449.

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

There are 149 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: 5.25%

Airbnb Rental Income: $1134

Traditional Rental Income: $2386

Airbnb ROI: 0.49%

Traditional ROI: 5.25%

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%

1610 S LOUDOUN Street

Winchester, VA

4 beds | 2 baths | 1,344 sq.ft.

$320,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2207

Airbnb ROI: N/A

Traditional ROI: 5.6%

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%

127 KINROSS Drive

Winchester, VA

5 beds | 4 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

2 beds | 2 baths | N/A

$274,900

Airbnb cash on cash: 0.29%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $956

Traditional Rental Income: $1544

Airbnb ROI: 0.29%

Traditional ROI: 3.9%

105 W OATES Avenue

Winchester, VA

3 beds | 2 baths | 1,066 sq.ft.

$345,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $1134

Traditional Rental Income: $2075

Airbnb ROI: 0.5%

Traditional ROI: 4.57%

156 SOLARA Drive

Winchester, VA

4 beds | 4 baths | 2,281 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2848

Airbnb ROI: N/A