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
17050 Florida Avenue Windsor, VA Beautifully maintained and thoughtfully updated 3-bedroom, 2-bath ranch situated on a scen...	3 beds \| 2 baths \| 1,200 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $1928 Airbnb ROI: N/A Traditional ROI: 4.93%
7501 Rhodes Drive Windsor, VA Great Purchase Opportunity for a Brick Home with an Oversized Concrete Block Detached Gara...	3 beds \| 2 baths \| 1,536 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $1945 Airbnb ROI: N/A Traditional ROI: 5.31%
25253 KELSIE Street Windsor, VA Beautiful home located in a sought-after Windsor neighborhood, set on a private wooded lot...	5 beds \| 3 baths \| 2,500 sq.ft.	$459,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $2828 Airbnb ROI: N/A Traditional ROI: 4.68%
14242 Trump Town Road Windsor, VA Modern Luxury Meets Country Living in Windsor! Experience the perfect blend of high-end st...	2 beds \| 1 baths \| 931 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $1530 Airbnb ROI: N/A Traditional ROI: 2.88%
12199 Ava Lane Windsor, VA Move in Ready-Quick Close for this Stunning Asheboro Ranch floorplan at Windsor Station! F...	4 beds \| 4 baths \| 3,201 sq.ft.	$569,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $3398 Airbnb ROI: N/A Traditional ROI: 4.56%
25452 Walters Highway Windsor, VA Looking for space and privacy? Look no further! This 5-bed, 2-bath, 2,500-square-foot ranc...	5 beds \| 2 baths \| 2,500 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2924 Airbnb ROI: N/A Traditional ROI: 5.19%
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 Move in Ready-Quick Close - The Cypress at Windsor Station! Experience the perfect blend o...	4 beds \| 3 baths \| 2,430 sq.ft.	$529,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 4.01%
.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: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $2929 Airbnb ROI: N/A Traditional ROI: 2.19%
44 N Court Street Windsor, VA This 4-bedroom, 2-bath ranch offers comfortable one-level living with a spacious and funct...	4 beds \| 2 baths \| 2,086 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.44% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 7.44%
12185 Ava Lane Windsor, VA This NEW Kestrel Ranch in Windsor Station is move-in ready in May! Beautiful Craftsman tou...	4 beds \| 4 baths \| 2,618 sq.ft.	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $3039 Airbnb ROI: N/A Traditional ROI: 3.43%
24456 Walters Highway Windsor, VA Nice 3 Bedroom, 2.5 Bath home on large corner lot. Stainless Steel Side by Side Refrigerat...	3 beds \| 3 baths \| 1,600 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $2133 Airbnb ROI: N/A Traditional ROI: 5.06%
11563 Savannah Street Windsor, VA This NEW Kestrel Ranch is move-in ready in June! Cozy cottage style on the outside leads t...	4 beds \| 4 baths \| 2,347 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2833 Airbnb ROI: N/A Traditional ROI: 3.16%
10455 Sylvia Circle Windsor, VA Welcome to this well-maintained transitional home in Windsor Woods in Windsor, Virginia. B...	4 beds \| 3 baths \| 2,535 sq.ft.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 4.44%
12236 Ava Lane Windsor, VA Welcome to Windsor Station! This stunning Halena model will be move-in ready this July and...	4 beds \| 4 baths \| 2,311 sq.ft.	$572,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $2781 Airbnb ROI: N/A Traditional ROI: 3.02%
12177 Ava Lane Windsor, VA Welcome to Windsor Station! This stunning Oakville model will be move-in ready this August...	4 beds \| 4 baths \| 2,650 sq.ft.	$583,800	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $2954 Airbnb ROI: N/A Traditional ROI: 3.25%
11564 Savannah Street Windsor, VA Welcome to Windsor Station! This stunning Halena model, elevation B,will be move-in ready ...	4 beds \| 4 baths \| 2,311 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $2794 Airbnb ROI: N/A Traditional ROI: 3.25%
25092 Tyler Drive Windsor, VA 3 bed 2.5 bath brick home, wooded 4.71 ac lot. 2 car attached garage. Large, detached 2 st...	3 beds \| 3 baths \| 2,567 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.92% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 2.92%
MM Kestrel (Ranch) Windsor Station Windsor, VA Welcome to the NEW Kestrel Ranch Model in Windsor Station, which combines country-style li...	3 beds \| 3 baths \| 1,979 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $2562 Airbnb ROI: N/A Traditional ROI: 3.19%

Real Estate investment in Windsor, VA

There are 19 properties for sale in the city of Windsor . The median list price in Windsor is $605,000 and the average price per square foot is $192. In June 2026, the average monthly cash on cash return in Windsor is 4.00%. The average monthly rental income in Windsor is $2,794.

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

There are 19 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

17050 Florida Avenue

Windsor, VA

3 beds | 2 baths | 1,200 sq.ft.

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.93%

Airbnb Rental Income: $null

Traditional Rental Income: $1928

Airbnb ROI: N/A

Traditional ROI: 4.93%

7501 Rhodes Drive

Windsor, VA

3 beds | 2 baths | 1,536 sq.ft.

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.31%

Airbnb Rental Income: $null

Traditional Rental Income: $1945

Airbnb ROI: N/A

Traditional ROI: 5.31%

25253 KELSIE Street

Windsor, VA

5 beds | 3 baths | 2,500 sq.ft.

$459,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2828

Airbnb ROI: N/A

Traditional ROI: 4.68%

14242 Trump Town Road

Windsor, VA

2 beds | 1 baths | 931 sq.ft.

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1530

Airbnb ROI: N/A

Traditional ROI: 2.88%

12199 Ava Lane

Windsor, VA

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

$569,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.56%

Airbnb Rental Income: $null

Traditional Rental Income: $3398

Airbnb ROI: N/A

Traditional ROI: 4.56%

25452 Walters Highway

Windsor, VA

5 beds | 2 baths | 2,500 sq.ft.

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2924

Airbnb ROI: N/A

Traditional ROI: 5.19%

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.

$529,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A