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
159 Abrams Pointe Blvd Winchester, VA ***You could get up to $3,000 with use of preferred lender for closing cost assistance or ...	5 beds \| 4 baths \| 3,963 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $4656 Airbnb ROI: N/A Traditional ROI: 4.87%
110 Brookland Ct #10 Winchester, VA Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transfor...	2 beds \| 2 baths \| 1,173 sq.ft.	$289,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 4.83% Airbnb Rental Income: $1126 Traditional Rental Income: $2042 Airbnb ROI: 0.26% Traditional ROI: 4.83%
108 Norfolk Ct Winchester, VA Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home ...	4 beds \| 4 baths \| 4,918 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $4402 Airbnb ROI: N/A Traditional ROI: 5.06%
775 Pack Horse Rd 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: 1.22% Traditional cash on cash: 3.41% Airbnb Rental Income: $1519 Traditional Rental Income: $1940 Airbnb ROI: 1.22% Traditional ROI: 3.41%
900 Enfield Dr Winchester, VA Recently renovated 4 bedroom, 2 1/2 bath county home with beautiful views! Corner lot on p...	4 beds \| 2 baths \| 2,243 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.25% Airbnb Rental Income: $null Traditional Rental Income: $2844 Airbnb ROI: N/A Traditional ROI: 6.25%
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.	$249,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 4.68% Airbnb Rental Income: $1126 Traditional Rental Income: $1609 Airbnb ROI: 1.03% Traditional ROI: 4.68%
1004 Heth Pl Winchester, VA Stepping onto the Southern style covered front porc.h you enter the large foyer with a Sc...	4 beds \| 3 baths \| 4,970 sq.ft.	$1,179,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $4479 Airbnb ROI: N/A Traditional ROI: 2.4%
802 E Cork St Winchester, VA Motivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, ...	4 beds \| 2 baths \| 1,996 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.51% Airbnb Rental Income: $null Traditional Rental Income: $2505 Airbnb ROI: N/A Traditional ROI: 6.51%
1950 Melvor Ln Winchester, VA Step into this meticulously maintained colonial home, a testament to quality craftsmanship...	4 beds \| 2 baths \| 3,108 sq.ft.	$665,000	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.	$379,900	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.55% Airbnb Rental Income: $1126 Traditional Rental Income: $2144 Airbnb ROI: -0.36% Traditional ROI: 3.55%
118 1/2 E Cork St Winchester, VA Seeking the perfect blend of historic character and modern urban living? This exceptional ...	2 beds \| 2 baths \| 1,419 sq.ft.	$399,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.69% Airbnb Rental Income: $1126 Traditional Rental Income: $1836 Airbnb ROI: -0.1% Traditional ROI: 2.69%
146 Darby Dr Winchester, VA Beautiful brick-front home in sought-after Ravenwing offering three finished levels and ex...	4 beds \| 3 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%
137 Old Forest Cir Winchester, VA Nestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded p...	4 beds \| 3 baths \| 4,152 sq.ft.	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $3872 Airbnb ROI: N/A Traditional ROI: 2.81%
110 Rugby Pl Winchester, VA Bank approved Short sale price opportunity with a significant price reduction-bring ...	3 beds \| 2 baths \| 1,625 sq.ft.	$370,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.93% Airbnb Rental Income: $1519 Traditional Rental Income: $2358 Airbnb ROI: 1.24% Traditional ROI: 4.93%
304 Shenandoah Ave Winchester, VA Classic charm in this brick Cape Cod located in Winchester City, just minutes from shoppin...	3 beds \| 1 baths \| 1,094 sq.ft.	$285,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 5.31% Airbnb Rental Income: $1519 Traditional Rental Income: $2009 Airbnb ROI: 1.84% Traditional ROI: 5.31%
115 Marion Dr Winchester, VA Situated on approximately 2.57 acres in Frederick County, this 4-bedroom, 2.5-bath Traditi...	4 beds \| 2 baths \| 2,967 sq.ft.	$629,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2963 Airbnb ROI: N/A Traditional ROI: 3.35%
121 Cherokee Trl Winchester, VA Lake and mountain views, a private in-ground pool, and an adjoining .63-acre lot - this be...	3 beds \| 3 baths \| 2,650 sq.ft.	$474,500	Airbnb cash on cash: 0.84% Traditional cash on cash: 5.89% Airbnb Rental Income: $1519 Traditional Rental Income: $3319 Airbnb ROI: 0.84% Traditional ROI: 5.89%
832 Winder Ct Winchester, VA Back on the market, at no fault of the seller. All-brick rancher located in the sought-aft...	3 beds \| 2 baths \| 1,974 sq.ft.	$480,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.57% Airbnb Rental Income: $1519 Traditional Rental Income: $2436 Airbnb ROI: -0.2% Traditional ROI: 2.57%
824 APPLESEED Court Winchester, VA Welcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hil...	3 beds \| 3 baths \| 2,052 sq.ft.	$365,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.43% Airbnb Rental Income: $1519 Traditional Rental Income: $2545 Airbnb ROI: 1.15% Traditional ROI: 5.43%
593 N Kent St Winchester, VA This charming home, a short walk from historic Winchester, underwent a complete studs up r...	3 beds \| 2 baths \| 1,310 sq.ft.	$319,950	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.15% Airbnb Rental Income: $1519 Traditional Rental Income: $2297 Airbnb ROI: 2.1% Traditional ROI: 6.15%
135 S Kent St #202 Winchester, VA Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban ...	1 beds \| 1 baths \| 740 sq.ft.	$250,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.61% Airbnb Rental Income: $762 Traditional Rental Income: $1462 Airbnb ROI: -0.31% Traditional ROI: 3.61%
621 Patterson Ave Winchester, VA Enchanting Cape Cod in an ideal in""Ã¢â¬Ëtown location, this home has a welcoming ease t...	4 beds \| 2 baths \| 2,050 sq.ft.	$357,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $2408 Airbnb ROI: N/A Traditional ROI: 5.03%
104 Bramble Ct Winchester, VA Welcome home to this beautifully maintained 3-level Colonial, perfectly situated on a quie...	4 beds \| 2 baths \| 2,904 sq.ft.	$624,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 3.24%
109 Gannentaha Trl Winchester, VA Pride of ownership shines throughout this exceptionally well-maintained and thoughtfully u...	2 beds \| 2 baths \| 1,555 sq.ft.	$325,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.61% Airbnb Rental Income: $1126 Traditional Rental Income: $1680 Airbnb ROI: 0.56% Traditional ROI: 3.61%

Real Estate investment in Winchester, VA

There are 394 properties for sale in the city of Winchester . The median list price in Winchester is $373,272 and the average price per square foot is $163. In October 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,457.

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

There are 394 investment properties available for sale in Winchester.

In 2026, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $2,457.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

159 Abrams Pointe Blvd

Winchester, VA

5 beds | 4 baths | 3,963 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $4656

Airbnb ROI: N/A

Traditional ROI: 4.87%

110 Brookland Ct #10

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$289,000

Airbnb cash on cash: 0.26%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1126

Traditional Rental Income: $2042

Airbnb ROI: 0.26%

Traditional ROI: 4.83%

108 Norfolk Ct

Winchester, VA

4 beds | 4 baths | 4,918 sq.ft.

$685,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.06%

Airbnb Rental Income: $null

Traditional Rental Income: $4402

Airbnb ROI: N/A

Traditional ROI: 5.06%

775 Pack Horse Rd

Winchester, VA

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

$420,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $1519

Traditional Rental Income: $1940

Airbnb ROI: 1.22%

Traditional ROI: 3.41%

900 Enfield Dr

Winchester, VA

4 beds | 2 baths | 2,243 sq.ft.

$380,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.25%

Airbnb Rental Income: $null

Traditional Rental Income: $2844

Airbnb ROI: N/A

Traditional ROI: 6.25%

2967 SORRELL Court

Winchester, VA

2 beds | 3 baths | 1,280 sq.ft.

$249,000

Airbnb cash on cash: 1.03%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1126

Traditional Rental Income: $1609

Airbnb ROI: 1.03%

Traditional ROI: 4.68%

1004 Heth Pl

Winchester, VA

4 beds | 3 baths | 4,970 sq.ft.

$1,179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.4%

Airbnb Rental Income: $null

Traditional Rental Income: $4479

Airbnb ROI: N/A

Traditional ROI: 2.4%

802 E Cork St

Winchester, VA

4 beds | 2 baths | 1,996 sq.ft.

$309,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2505

Airbnb ROI: N/A