Real Estate Investment Properties for Sale in Windsor, VA

Looking for investment property in Windsor, VA with high ROI ?

Explore a variety of short-term homes & houses in Windsor, VA. Invest wisely with VRBO & Windsor, 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 Windsor, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
13067 Poor House Road Windsor, VA Welcome to this beautifully updated 3-bedroom, 2-bath rancher on a spacious lot! This home...	3 beds \| 2 baths \| 1,515 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $1884 Airbnb ROI: N/A Traditional ROI: 4.39%
12199 Ava Lane Windsor, VA The Asheboro in Windsor Station is a four-bedroom, three-and-a-half-bath home featuring a ...	4 beds \| 4 baths \| 3,201 sq.ft.	$599,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $3398 Airbnb ROI: N/A Traditional ROI: 4.29%
15023 Five Forks Road Windsor, VA 12-acres of exceptional beauty and privacy features a welcoming picket fence and crepe myr...	3 beds \| 4 baths \| 2,919 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $3631 Airbnb ROI: N/A Traditional ROI: 1.71%
MM Roanoke Windsor, VA Welcome to the Roanoke by Eastwood Homes at Windsor Station! This beautifully designed two...	5 beds \| 4 baths \| 3,691 sq.ft.	$589,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3497 Airbnb ROI: N/A Traditional ROI: 4.32%
MM Davidson Windsor, VA The Davidson is a two-story, five-bedroom, three-bath home with a formal living room, form...	5 beds \| 3 baths \| 3,047 sq.ft.	$544,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $3123 Airbnb ROI: N/A Traditional ROI: 4.02%
MM WINDSOR STATION (Drexel) Windsor, VA The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living roo...	4 beds \| 3 baths \| 2,591 sq.ft.	$519,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $2919 Airbnb ROI: N/A Traditional ROI: 3.92%
12169 Ava Lane Windsor, VA The Cypress is a two-story, four-bedroom, three-bath home with a formal dining room, a fir...	4 beds \| 3 baths \| 2,430 sq.ft.	$549,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 3.83%
MM Caldwell Windsor, VA The Caldwell is a ranch-style home with three bedrooms, two full baths, a first-floor prim...	3 beds \| 2 baths \| 2,071 sq.ft.	$499,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2554 Airbnb ROI: N/A Traditional ROI: 3.35%
MM Raleigh Windsor, VA The Raleigh is a two-story, four-bedroom, two-and-a-half-bath home with a first-floor prim...	4 beds \| 4 baths \| 2,449 sq.ft.	$509,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $2972 Airbnb ROI: N/A Traditional ROI: 4.13%
MM Charleston Windsor, VA The Charleston at Windsor Station is a stunning two-story, five-bedroom, three-bath home w...	5 beds \| 3 baths \| 3,483 sq.ft.	$579,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $3124 Airbnb ROI: N/A Traditional ROI: 3.72%
MM Asheboro Windsor, VA The Asheboro at Windsor Station is a three-bedroom, two-and-a-half-bath home with a first-...	3 beds \| 3 baths \| 2,583 sq.ft.	$534,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $2833 Airbnb ROI: N/A Traditional ROI: 3.53%
MM McDowell Windsor, VA The McDowell at Windsor Station is a two-story, four-bedroom, three-and-a-half-bath home w...	4 beds \| 4 baths \| 3,294 sq.ft.	$574,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $3403 Airbnb ROI: N/A Traditional ROI: 4.28%
10174 Bank Street Windsor, VA New construction with premium upgrades by an award-winning builderâmove-in ready and bui...	3 beds \| 2 baths \| 1,725 sq.ft.	$384,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.81% Airbnb Rental Income: $null Traditional Rental Income: $2222 Airbnb ROI: N/A Traditional ROI: 4.81%
.47AC Holland Drive Windsor, VA WELCOME TO THE CAPRON, THE LATEST CREATION FROM SOUTHEASTERN VIRGINIA'S PREMIER RURAL CUST...	4 beds \| 3 baths \| 2,901 sq.ft.	$714,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: 1.4%

Real Estate investment in Windsor, VA

There are 14 properties for sale in the city of Windsor . The median list price in Windsor is $625,000 and the average price per square foot is $194. In February 2026, the average monthly cash on cash return in Windsor is 4.00%. The average monthly rental income in Windsor is $2,919.

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

There are 14 investment properties available for sale in Windsor.

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, VA

13067 Poor House Road

Windsor, VA

3 beds | 2 baths | 1,515 sq.ft.

$329,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.39%

Airbnb Rental Income: $null

Traditional Rental Income: $1884

Airbnb ROI: N/A

Traditional ROI: 4.39%

12199 Ava Lane

Windsor, VA

4 beds | 4 baths | 3,201 sq.ft.

$599,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.29%

Airbnb Rental Income: $null

Traditional Rental Income: $3398

Airbnb ROI: N/A

Traditional ROI: 4.29%

15023 Five Forks Road

Windsor, VA

3 beds | 4 baths | 2,919 sq.ft.

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.71%

Airbnb Rental Income: $null

Traditional Rental Income: $3631

Airbnb ROI: N/A

Traditional ROI: 1.71%

MM Roanoke

Windsor, VA

5 beds | 4 baths | 3,691 sq.ft.

$589,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $3497

Airbnb ROI: N/A

Traditional ROI: 4.32%

MM Davidson

Windsor, VA

5 beds | 3 baths | 3,047 sq.ft.

$544,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.02%

Airbnb Rental Income: $null

Traditional Rental Income: $3123

Airbnb ROI: N/A

Traditional ROI: 4.02%

MM WINDSOR STATION (Drexel)

Windsor, VA

4 beds | 3 baths | 2,591 sq.ft.

$519,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2919

Airbnb ROI: N/A

Traditional ROI: 3.92%

12169 Ava Lane

Windsor, VA

4 beds | 3 baths | 2,430 sq.ft.

$549,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A

Traditional ROI: 3.83%

MM Caldwell

Windsor, VA

3 beds | 2 baths | 2,071 sq.ft.

$499,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2554

Airbnb ROI: N/A