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
719 Smithfield Avenue Winchester, VA Bringing all the bungalow love! . **$8,000 closing cost credit to buyer with acceptable of...	2 beds \| 1 baths \| 720 sq.ft.	$274,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.74% Airbnb Rental Income: $897 Traditional Rental Income: $1368 Airbnb ROI: 0.62% 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: -0.62% Traditional cash on cash: 3.67% Airbnb Rental Income: $805 Traditional Rental Income: $2446 Airbnb ROI: -0.62% Traditional ROI: 3.67%
120 WORSHAM Terrace Winchester, VA This beautifully maintained 3 level townhome is a great place to call home. Perfectly situ...	3 beds \| 4 baths \| 1,336 sq.ft.	$324,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 5.41% Airbnb Rental Income: $805 Traditional Rental Income: $2184 Airbnb ROI: -0.17% Traditional ROI: 5.41%
109 HURON TRL Winchester, VA Discover this inviting 3-bedroom, 2-bath tri""Ã¢â¬Ëlevel home, offering flexible living ...	3 beds \| 2 baths \| N/A	$359,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.59% Airbnb Rental Income: $805 Traditional Rental Income: $2112 Airbnb ROI: -0.24% Traditional ROI: 4.59%
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.	$699,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.34% Airbnb Rental Income: $805 Traditional Rental Income: $3189 Airbnb ROI: -0.81% Traditional ROI: 3.34%
775 PACK HORSE Road Winchester, VA Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in F...	3 beds \| 2 baths \| 1,188 sq.ft.	$420,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.41% Airbnb Rental Income: $805 Traditional Rental Income: $1940 Airbnb ROI: -0.3% Traditional ROI: 3.41%
13 E LEICESTER Street Winchester, VA Incredible location, incredible home! Relax on the elevated front porch overlooking Leices...	3 beds \| 2 baths \| 1,601 sq.ft.	$399,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 4.03% Airbnb Rental Income: $805 Traditional Rental Income: $2108 Airbnb ROI: -0.31% Traditional ROI: 4.03%
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%
1239 CEDAR GROVE Road Winchester, VA Experience the perfect blend of historic artistry and modern convenience in this stunning ...	3 beds \| 2 baths \| 1,793 sq.ft.	$560,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.91% Airbnb Rental Income: $805 Traditional Rental Income: $2305 Airbnb ROI: -0.58% Traditional ROI: 2.91%
2967 SORRELL Court Winchester, VA This diamond in the rough has solid bones and plenty of potential for the right buyer. The...	2 beds \| 3 baths \| 1,280 sq.ft.	$273,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.19% Airbnb Rental Income: $897 Traditional Rental Income: $1609 Airbnb ROI: 0.11% Traditional ROI: 4.19%
704 WATSON Avenue Winchester, VA Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 ...	2 beds \| 2 baths \| 864 sq.ft.	$280,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.35% Airbnb Rental Income: $897 Traditional Rental Income: $1397 Airbnb ROI: 0.18% Traditional ROI: 3.35%
104 VAN BUREN Place Winchester, VA Move-in ready 4-bedroom, 2.5-bath home on the east side of Winchester with numerous upgrad...	4 beds \| 3 baths \| 1,714 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2519 Airbnb ROI: N/A Traditional ROI: 4.8%
405 SPRING VALLEY Drive Winchester, VA NO HOA!!! Square footage: total: 4,050/ above ground: 2,688. Basement partially finished 8...	4 beds \| 3 baths \| 4,050 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3086 Airbnb ROI: N/A Traditional ROI: 3.22%
802 E CORK Street Winchester, VA Check out the Virtual Tour! Rich with character and steeped in history, this spacious vint...	4 beds \| 2 baths \| 1,996 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $2505 Airbnb ROI: N/A Traditional ROI: 5.66%
16 S PLEASANT VALLEY Road Winchester, VA Welcome to 16 S Pleasant Valley Rd - a beautifully updated home just minutes from the hear...	3 beds \| 3 baths \| 1,600 sq.ft.	$354,999	Airbnb cash on cash: -0.54% Traditional cash on cash: 5.06% Airbnb Rental Income: $805 Traditional Rental Income: $2349 Airbnb ROI: -0.54% Traditional ROI: 5.06%
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: -0.06% Traditional cash on cash: 8.07% Airbnb Rental Income: $805 Traditional Rental Income: $2212 Airbnb ROI: -0.06% 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.	$689,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.45%
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.	$389,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.43% Airbnb Rental Income: $897 Traditional Rental Income: $2144 Airbnb ROI: -0.9% Traditional ROI: 3.43%
146 DARBY Drive Winchester, VA Beautiful brick-front home in sought-after Ravenwing offering three finished levels and ex...	4 beds \| 4 baths \| 3,924 sq.ft.	$674,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $3494 Airbnb ROI: N/A Traditional ROI: 3.95%
450 FISHEL Road Winchester, VA Welcome to this 3-bed, 3-and-a-half-bath all-brick estate offering the perfect blend of pr...	3 beds \| 4 baths \| 3,465 sq.ft.	$585,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 3.92% Airbnb Rental Income: $805 Traditional Rental Income: $3030 Airbnb ROI: -0.75% Traditional ROI: 3.92%
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.	$539,900	Airbnb cash on cash: -1.4% Traditional cash on cash: 2.47% Airbnb Rental Income: $805 Traditional Rental Income: $2436 Airbnb ROI: -1.4% Traditional ROI: 2.47%
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.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $4682 Airbnb ROI: N/A Traditional ROI: 4.86%
31 E GERMAIN Street Winchester, VA IMPROVED PRICING! Nestled in the heart of Winchester City's Historic District and walkable...	2 beds \| 2 baths \| 1,382 sq.ft.	$319,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 4.98% Airbnb Rental Income: $897 Traditional Rental Income: $2060 Airbnb ROI: -0.02% Traditional ROI: 4.98%
540 Eagle Place Winchester, VA Great opportunity for a rental investment! This well-maintained one-level rancher is tucke...	3 beds \| 2 baths \| 1,450 sq.ft.	$382,500	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.45% Airbnb Rental Income: $805 Traditional Rental Income: $2263 Airbnb ROI: -0.52% Traditional ROI: 4.45%
115 BROCKHAM Court Winchester, VA Beautifully upgraded, like-new 3-bedroom, 2 full and 2 half bath townhouse with a 2-car ga...	3 beds \| 4 baths \| 2,376 sq.ft.	$429,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 5.04% Airbnb Rental Income: $805 Traditional Rental Income: $2724 Airbnb ROI: -0.53% Traditional ROI: 5.04%
332 OPEQUON Avenue Winchester, VA Adorable ranch home with great potential - TLC needed. The home has a large family room fo...	3 beds \| 1 baths \| 1,404 sq.ft.	$257,500	Airbnb cash on cash: -0.22% Traditional cash on cash: 4.58% Airbnb Rental Income: $805 Traditional Rental Income: $1650 Airbnb ROI: -0.22% Traditional ROI: 4.58%
1015 REDBUD Winchester, VA Set on over 10 private acres in the quiet Locust Level Estates community, this beautifully...	4 beds \| 5 baths \| 4,188 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $4576 Airbnb ROI: N/A Traditional ROI: 2.61%
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%
605 DUNLAP Street Winchester, VA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-ba...	5 beds \| 2 baths \| 1,011 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $2388 Airbnb ROI: N/A Traditional ROI: 4.69%
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.	$424,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.51% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 5.51%
104 HILLTOP Terrace Winchester, VA THIS HOME IS A MUST SEE! THIS WELL CARED FOR MOVE IN READY HOME HAS NEW UPDATED STAINLESS ...	3 beds \| 1 baths \| 1,360 sq.ft.	$349,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.87% Airbnb Rental Income: $805 Traditional Rental Income: $1811 Airbnb ROI: -0.17% Traditional ROI: 3.87%
357 HUNTING RIDGE Road Winchester, VA Completely remodeled in 2023, this 3-bedroom, 2-bath rancher offers modern updates and a f...	3 beds \| 2 baths \| 3,029 sq.ft.	$525,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.12% Airbnb Rental Income: $805 Traditional Rental Income: $2351 Airbnb ROI: -0.69% Traditional ROI: 3.12%
127 GERONIMO Trail Winchester, VA Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfe...	3 beds \| 1 baths \| 970 sq.ft.	$235,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.83% Airbnb Rental Income: $805 Traditional Rental Income: $1693 Airbnb ROI: 0.38% Traditional ROI: 5.83%
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.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $1909 Airbnb ROI: N/A Traditional ROI: 3.6%
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.	$329,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.18% Airbnb Rental Income: $805 Traditional Rental Income: $1568 Airbnb ROI: -0.33% Traditional ROI: 3.18%

Real Estate investment in Winchester, VA

There are 186 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 $197. In May 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,427.

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

There are 186 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 $805.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

719 Smithfield Avenue

Winchester, VA

2 beds | 1 baths | 720 sq.ft.

$274,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $897

Traditional Rental Income: $1368

Airbnb ROI: 0.62%

Traditional ROI: 3.74%

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$489,999

Airbnb cash on cash: -0.62%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $805

Traditional Rental Income: $2446

Airbnb ROI: -0.62%

Traditional ROI: 3.67%

120 WORSHAM Terrace

Winchester, VA

3 beds | 4 baths | 1,336 sq.ft.

$324,900

Airbnb cash on cash: -0.17%

Traditional cash on cash: 5.41%

Airbnb Rental Income: $805

Traditional Rental Income: $2184

Airbnb ROI: -0.17%

Traditional ROI: 5.41%

109 HURON TRL

Winchester, VA

3 beds | 2 baths | N/A

$359,900

Airbnb cash on cash: -0.24%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $805

Traditional Rental Income: $2112

Airbnb ROI: -0.24%

Traditional ROI: 4.59%

171 LAUREL GROVE Road

Winchester, VA

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

$699,900

Airbnb cash on cash: -0.81%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $805

Traditional Rental Income: $3189

Airbnb ROI: -0.81%

Traditional ROI: 3.34%

775 PACK HORSE Road

Winchester, VA

3 beds | 2 baths | 1,188 sq.ft.

$420,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $805

Traditional Rental Income: $1940

Airbnb ROI: -0.3%

Traditional ROI: 3.41%

13 E LEICESTER Street

Winchester, VA

3 beds | 2 baths | 1,601 sq.ft.

$399,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $805

Traditional Rental Income: $2108

Airbnb ROI: -0.31%

Traditional ROI: 4.03%

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