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
24209 Lovers Ln Windsor, VA Welcome to 24209 Lovers Ln! This spacious home offers multiple living areas, thoughtful up...	3 beds \| 2 baths \| 2,160 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $2317 Airbnb ROI: N/A Traditional ROI: 5.28%
25253 Kelsie St 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%
25452 Walters Hwy 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.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2924 Airbnb ROI: N/A Traditional ROI: 5.4%
12169 Ava Ln 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.	$538,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 3.93%
.47AC Holland Dr Windsor, VA WELCOME TO THE MAYFIELD, ANOTHER FABULOUS HOME FROM SUFFOLK & ISLE OF WIGHTS PREMIER CUSTO...	4 beds \| 2 baths \| 2,342 sq.ft.	$588,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2929 Airbnb ROI: N/A Traditional ROI: 3.38%
Davidson Plan Windsor, VA Davidson Plan, Windsor, VA 23487 \| Single Family Residential	5 beds \| 3 baths \| 3,047 sq.ft.	$544,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2576 Airbnb ROI: N/A Traditional ROI: 2.9%
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: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 2.66%
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%
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: 2.13% Airbnb Rental Income: $null Traditional Rental Income: $2056 Airbnb ROI: N/A Traditional ROI: 2.13%
15+AC Courthouse Hwy Windsor, VA 15+AC Courthouse Hwy, Windsor, VA 23487 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.02% Airbnb Rental Income: $null Traditional Rental Income: $632 Airbnb ROI: N/A Traditional ROI: 1.02%
.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%
44 N Court St 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 Ln Windsor, VA This NEW Kestrel Ranch in Windsor Station is move-in ready NOW!! Beautiful Craftsman touch...	4 beds \| 3 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%
11563 Savannah St Windsor, VA This NEW Kestrel Ranch is move-in ready, only finishing touches remain!! Cozy cottage styl...	4 beds \| 3 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%
12236 Ava Ln Windsor, VA Welcome to Windsor Station! This stunning Halena model will be move-in ready this July and...	4 beds \| 3 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 Ln Windsor, VA Welcome to Windsor Station! This stunning Oakville model will be move-in ready this August...	4 beds \| 3 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 St Windsor, VA Welcome to Windsor Station! This stunning Halena model, elevation B,will be move-in ready ...	4 beds \| 3 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 Dr Windsor, VA Instant equity potential! Appraised 2026 $600K. 4.71 acres & no HOA in Windsor VA. 1994 br...	3 beds \| 2 baths \| 2,567 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 3.38%
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%
MM Drexel Windsor, VA The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living roo...	4 beds \| 2 baths \| 2,591 sq.ft.	$519,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2924 Airbnb ROI: N/A Traditional ROI: 3.93%
MM Davidson Windsor, VA Enter into The Davidson by Eastwood Homes at Windsor Station, a beautifully designed two-s...	5 beds \| 3 baths \| 3,047 sq.ft.	$544,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $3135 Airbnb ROI: N/A Traditional ROI: 4.04%
MM Caldwell Windsor, VA Experience effortless living in The Caldwell by Eastwood Homes at Windsor Station, a beaut...	3 beds \| 2 baths \| 2,071 sq.ft.	$499,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.4% Airbnb Rental Income: $null Traditional Rental Income: $2575 Airbnb ROI: N/A Traditional ROI: 3.4%
MM Mcdowell Windsor, VA Welcome to The McDowell by Eastwood Homes at Windsor Station, a stunning two-story home de...	4 beds \| 3 baths \| 3,294 sq.ft.	$574,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3425 Airbnb ROI: N/A Traditional ROI: 4.32%
MM Raleigh Windsor, VA Discover luxury living in The Raleigh by Eastwood Homes at Windsor Station, a stunning two...	4 beds \| 2 baths \| 2,449 sq.ft.	$509,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $2926 Airbnb ROI: N/A Traditional ROI: 4.03%
MM Cypress (windsor Station) Windsor, VA Discover The Cypress by Eastwood Homes at Windsor Station, where modern elegance meets tim...	4 beds \| 3 baths \| 2,430 sq.ft.	$514,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.89% Airbnb Rental Income: $null Traditional Rental Income: $2923 Airbnb ROI: N/A Traditional ROI: 3.89%
24129 Johnson Ave Windsor, VA Come and make your new home in Windsor Virginia, voted the friendliest community by Nextdo...	3 beds \| 2 baths \| 1,225 sq.ft.	$308,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $1974 Airbnb ROI: N/A Traditional ROI: 4.86%
9269 Whispering Pines Trl Windsor, VA Hunter's paradise on 5.93 private acres! Zoned Rural Residential, this peaceful property o...	3 beds \| 2 baths \| 1,452 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.08% Airbnb Rental Income: $null Traditional Rental Income: $2127 Airbnb ROI: N/A Traditional ROI: 4.08%
8368 Whispering Pines Trail Windsor, VA Welcome to Whispering Pines Trail, a rare opportunity to own a beautifully updated home on...	3 beds \| 2 baths \| 2,208 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $2303 Airbnb ROI: N/A Traditional ROI: 3.57%
12330 Ava Lane Windsor, VA Step into The Davidson by Eastwood Homes at Windsor Station, a beautifully designed two-st...	5 beds \| 3 baths \| 3,047 sq.ft.	$609,595	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $3015 Airbnb ROI: N/A Traditional ROI: 3.45%
12242 Ava Ln Windsor, VA 12242 Ava Ln, Windsor, VA 23487 \| Single Family Residential	6 beds \| 3 baths \| 3,958 sq.ft.	$639,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $2462 Airbnb ROI: N/A Traditional ROI: 2.01%
12162 Ava Ln Windsor, VA 12162 Ava Ln, Windsor, VA 23487 \| Single Family Residential	5 beds \| 3 baths \| 2,990 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.54% Airbnb Rental Income: $null Traditional Rental Income: $2612 Airbnb ROI: N/A Traditional ROI: 2.54%
18517 Shady Pine LN Windsor, VA Escape to your own private 14.84-Acre wooded retreat in Windsor! Discover ultimate privacy...	5 beds \| 5 baths \| N/A	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.83% Airbnb Rental Income: $null Traditional Rental Income: $4708 Airbnb ROI: N/A Traditional ROI: 5.83%
9545 Windsor Boulevard Windsor, VA Charming rancher on almost 5 acres of land! This cute home features a completely freshly p...	2 beds \| 1 baths \| 1,086 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $1622 Airbnb ROI: N/A Traditional ROI: 4.48%

Real Estate investment in Windsor, VA

There are 35 properties for sale in the city of Windsor . The median list price in Windsor is $384,719 and the average price per square foot is $123. In July 2026, the average monthly cash on cash return in Windsor is 3.00%. The average monthly rental income in Windsor is $2,694.

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

There are 35 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

24209 Lovers Ln

Windsor, VA

3 beds | 2 baths | 2,160 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2317

Airbnb ROI: N/A

Traditional ROI: 5.28%

25253 Kelsie St

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%

25452 Walters Hwy

Windsor, VA

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

$435,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2924

Airbnb ROI: N/A

Traditional ROI: 5.4%

12169 Ava Ln

Windsor, VA

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

$538,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A

Traditional ROI: 3.93%

.47AC Holland Dr

Windsor, VA

4 beds | 2 baths | 2,342 sq.ft.

$588,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2929

Airbnb ROI: N/A

Traditional ROI: 3.38%

Davidson Plan

Windsor, VA

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

$544,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2576

Airbnb ROI: N/A

Traditional ROI: 2.9%

Cypress Plan

Windsor, VA

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

$514,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.66%

Airbnb Rental Income: $null

Traditional Rental Income: $2331

Airbnb ROI: N/A

Traditional ROI: 2.66%

Caldwell Plan

Windsor, VA

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