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
17036 N Carolina Avenue Windsor, VA Quiet Country Living with Modern Comforts Enjoy peaceful country living in this well-main...	3 beds \| 1 baths \| 1,104 sq.ft.	$224,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.32% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 7.32%
25 E Griffin Street Windsor, VA This home features 4 spacious bedrooms and a large full size bathroom, home is move-in rea...	4 beds \| 1 baths \| 2,133 sq.ft.	$345,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $1646 Airbnb ROI: N/A Traditional ROI: 3.16%
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.	$598,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $3398 Airbnb ROI: N/A Traditional ROI: 4.3%
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 Windsor Station (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 Windsor Station (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.	$548,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 3.84%
MM Windsor Station (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 Windsor Station (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 Windsor Station (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 Windsor Station (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 Windsor Station (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%
.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%
Roanoke Plan Windsor, VA Roanoke Plan, Windsor, VA 23487 \| Single Family Residential	5 beds \| 4 baths \| 3,691 sq.ft.	$589,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $2862 Airbnb ROI: N/A Traditional ROI: 3.06%
Cypress Plan Windsor, VA Cypress Plan, Windsor, VA 23487 \| Single Family Residential	4 beds \| 3 baths \| 2,430 sq.ft.	$514,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: 2.8%
Caldwell Plan Windsor, VA Caldwell Plan, Windsor, VA 23487 \| Single Family Residential	3 beds \| 2 baths \| 2,071 sq.ft.	$499,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.78% Airbnb Rental Income: $null Traditional Rental Income: $1857 Airbnb ROI: N/A Traditional ROI: 1.78%
McDowell Plan Windsor, VA McDowell Plan, Windsor, VA 23487 \| Single Family Residential	4 beds \| 3 baths \| 3,294 sq.ft.	$574,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $2157 Airbnb ROI: N/A Traditional ROI: 1.87%
Asheboro Plan Windsor, VA Asheboro Plan, Windsor, VA 23487 \| Single Family Residential	3 beds \| 2 baths \| 2,583 sq.ft.	$534,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 1.82%
Raleigh Plan Windsor, VA Raleigh Plan, Windsor, VA 23487 \| Single Family Residential	4 beds \| 2 baths \| 2,449 sq.ft.	$509,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: 2.85%
15+AC Courthouse Hwy Windsor, VA 15+AC Courthouse Hwy, Windsor, VA 23487 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $1284 Airbnb ROI: N/A Traditional ROI: 2.78%
.71 Ac E Windsor Blvd Windsor, VA .71 Ac E Windsor Blvd, Windsor, VA 23487 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.9% Airbnb Rental Income: $null Traditional Rental Income: $545 Airbnb ROI: N/A Traditional ROI: 0.9%
Drexel Plan Windsor, VA Drexel Plan, Windsor, VA 23487 \| Single Family Residential	4 beds \| 2 baths \| 2,591 sq.ft.	$519,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.93% Airbnb Rental Income: $null Traditional Rental Income: $1996 Airbnb ROI: N/A Traditional ROI: 1.93%
Charleston Plan Windsor, VA Charleston Plan, Windsor, VA 23487 \| Single Family Residential	5 beds \| 3 baths \| 3,483 sq.ft.	$579,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 2.26%
105 S Court Street Windsor, VA New construction with premium upgrades by an award-winning builder-move-in ready and built...	3 beds \| 3 baths \| 1,480 sq.ft.	$354,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 4.68%
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: 6.39% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: 6.39%
10176 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: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 3.37%
16290 Trump Town Road Windsor, VA Welcome Home to 16290 Trump Town Road in Windsor, VA! Nestled on over 3 peaceful acres in ...	3 beds \| 2 baths \| 2,022 sq.ft.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.34% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 2.34%

Real Estate investment in Windsor, VA

There are 28 properties for sale in the city of Windsor . The median list price in Windsor is $599,900 and the average price per square foot is $190. In March 2026, the average monthly cash on cash return in Windsor is 3.00%. The average monthly rental income in Windsor is $2,399.

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

There are 28 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

17036 N Carolina Avenue

Windsor, VA

3 beds | 1 baths | 1,104 sq.ft.

$224,999

Airbnb cash on cash: N/A

Traditional cash on cash: 7.32%

Airbnb Rental Income: $null

Traditional Rental Income: $1995

Airbnb ROI: N/A

Traditional ROI: 7.32%

25 E Griffin Street

Windsor, VA

4 beds | 1 baths | 2,133 sq.ft.

$345,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.16%

Airbnb Rental Income: $null

Traditional Rental Income: $1646

Airbnb ROI: N/A

Traditional ROI: 3.16%

12199 Ava Lane

Windsor, VA

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

$598,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.3%

Airbnb Rental Income: $null

Traditional Rental Income: $3398

Airbnb ROI: N/A

Traditional ROI: 4.3%

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 Windsor Station (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 Windsor Station (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.

$548,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A