Real Estate Investment Properties for Sale in Windsor, PA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2402 CRALEY Road Windsor, PA Completely renovated in 2020, this 3 bedroom, 2 bath cape cod with wrap around porch just ...	3 beds \| 2 baths \| 1,713 sq.ft.	$297,500	Airbnb cash on cash: 0.91% Traditional cash on cash: 5.18% Airbnb Rental Income: $1480 Traditional Rental Income: $2241 Airbnb ROI: 0.91% Traditional ROI: 5.18%
333 NEWCOMER RD Windsor, PA Owner is retiring and moving, The property features Two Homes and buildings that were part...	4 beds \| 3 baths \| 2,488 sq.ft.	$949,900	Airbnb cash on cash: -1.72% Traditional cash on cash: 1.26% Airbnb Rental Income: $779 Traditional Rental Income: $3095 Airbnb ROI: -1.72% Traditional ROI: 1.26%
10 AZALEA Drive Windsor, PA Sunday 1/4/26 - Open House 1-3 pm. Featuring an open-concept layout, this 2-3 bedroom, 2 f...	3 beds \| 2 baths \| 3,185 sq.ft.	$465,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.91% Airbnb Rental Income: $1480 Traditional Rental Income: $2092 Airbnb ROI: -0.5% Traditional ROI: 1.91%
88 E MAIN Street Windsor, PA SELLER FINANCING AVAILABLE* Welcome to this beautifully maintained townhome that blends ...	2 beds \| 1 baths \| 1,440 sq.ft.	$199,900	Airbnb cash on cash: -1.02% Traditional cash on cash: 4.94% Airbnb Rental Income: $652 Traditional Rental Income: $1484 Airbnb ROI: -1.02% Traditional ROI: 4.94%
2 Windsor Acrs Windsor, PA 2 Windsor Acrs, Windsor, PA 17366 \| Manufactured Home	2 beds \| 1 baths \| 800 sq.ft.	$59,500	Airbnb cash on cash: 1.87% Traditional cash on cash: 10.89% Airbnb Rental Income: $652 Traditional Rental Income: $893 Airbnb ROI: 1.87% Traditional ROI: 10.89%
42 Water St Windsor, PA 42 Water St, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 1,686 sq.ft.	$199,900	Airbnb cash on cash: -0.62% Traditional cash on cash: 6.73% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -0.62% Traditional ROI: 6.73%
307 Boxwood Dr Windsor, PA 307 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$451,990	Airbnb cash on cash: -1.78% Traditional cash on cash: 1.98% Airbnb Rental Income: $779 Traditional Rental Income: $2055 Airbnb ROI: -1.78% Traditional ROI: 1.98%
311 Boxwood Dr Windsor, PA 311 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$455,990	Airbnb cash on cash: -1.79% Traditional cash on cash: 1.95% Airbnb Rental Income: $779 Traditional Rental Income: $2058 Airbnb ROI: -1.79% Traditional ROI: 1.95%
100 Schoolhouse Ln #MAGNOLIA Windsor, PA 100 Schoolhouse Ln #MAGNOLIA, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,953 sq.ft.	$493,763	Airbnb cash on cash: -1.85% Traditional cash on cash: 1.9% Airbnb Rental Income: $779 Traditional Rental Income: $2191 Airbnb ROI: -1.85% Traditional ROI: 1.9%
309 Boxwood Dr Windsor, PA 309 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$449,990	Airbnb cash on cash: -1.78% Traditional cash on cash: 2% Airbnb Rental Income: $779 Traditional Rental Income: $2053 Airbnb ROI: -1.78% Traditional ROI: 2%
100 Schoolhouse Ln #HAWTHORNE Windsor, PA 100 Schoolhouse Ln #HAWTHORNE, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 3,646 sq.ft.	$520,038	Airbnb cash on cash: -1.89% Traditional cash on cash: 1.13% Airbnb Rental Income: $779 Traditional Rental Income: $1929 Airbnb ROI: -1.89% Traditional ROI: 1.13%
Caldwell Plan Windsor, PA	3 beds \| 2 baths \| 1,664 sq.ft.	$433,103	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.94% Airbnb Rental Income: $1480 Traditional Rental Income: $2325 Airbnb ROI: -0.22% Traditional ROI: 2.94%
Harrison Plan Windsor, PA	3 beds \| 2 baths \| 2,002 sq.ft.	$447,588	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.76% Airbnb Rental Income: $1480 Traditional Rental Income: $2325 Airbnb ROI: -0.29% Traditional ROI: 2.76%
100 Schoolhouse Ln #SEBASTIAN Windsor, PA 100 Schoolhouse Ln #SEBASTIAN, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,701 sq.ft.	$477,116	Airbnb cash on cash: -1.83% Traditional cash on cash: 1.94% Airbnb Rental Income: $779 Traditional Rental Income: $2140 Airbnb ROI: -1.83% Traditional ROI: 1.94%
Arcadia Plan Windsor, PA	3 beds \| 2 baths \| 1,982 sq.ft.	$487,945	Airbnb cash on cash: -0.48% Traditional cash on cash: 2.32% Airbnb Rental Income: $1480 Traditional Rental Income: $2325 Airbnb ROI: -0.48% Traditional ROI: 2.32%
Kipling Plan Windsor, PA Kipling Plan, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 2,801 sq.ft.	$515,302	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.15% Airbnb Rental Income: $1480 Traditional Rental Income: $1884 Airbnb ROI: -0.59% Traditional ROI: 1.15%
100 Schoolhouse Ln #COVINGTON Windsor, PA 100 Schoolhouse Ln #COVINGTON, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 3,405 sq.ft.	$506,570	Airbnb cash on cash: -1.87% Traditional cash on cash: 1.23% Airbnb Rental Income: $779 Traditional Rental Income: $1929 Airbnb ROI: -1.87% Traditional ROI: 1.23%
100 Schoolhouse Ln #LACHLAN Windsor, PA 100 Schoolhouse Ln #LACHLAN, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,346 sq.ft.	$465,697	Airbnb cash on cash: -1.81% Traditional cash on cash: 1.89% Airbnb Rental Income: $779 Traditional Rental Income: $2073 Airbnb ROI: -1.81% Traditional ROI: 1.89%
100 Schoolhouse Ln #ADDISON Windsor, PA 100 Schoolhouse Ln #ADDISON, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,594 sq.ft.	$478,290	Airbnb cash on cash: -1.83% Traditional cash on cash: 1.29% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.83% Traditional ROI: 1.29%
Parker Plan Windsor, PA	4 beds \| 2 baths \| 2,705 sq.ft.	$475,516	Airbnb cash on cash: -1.74% Traditional cash on cash: 1.39% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.74% Traditional ROI: 1.39%
100 Schoolhouse Ln #ANDREWS Windsor, PA 100 Schoolhouse Ln #ANDREWS, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 1,819 sq.ft.	$441,472	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.7% Airbnb Rental Income: $1480 Traditional Rental Income: $1892 Airbnb ROI: -0.35% Traditional ROI: 1.7%
Andrews Plan Windsor, PA	3 beds \| 2 baths \| 1,819 sq.ft.	$441,472	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.46% Airbnb Rental Income: $1480 Traditional Rental Income: $1758 Airbnb ROI: -0.26% Traditional ROI: 1.46%
Sebastian Plan Windsor, PA	4 beds \| 2 baths \| 2,701 sq.ft.	$477,116	Airbnb cash on cash: -1.74% Traditional cash on cash: 1.38% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.74% Traditional ROI: 1.38%
Magnolia Plan Windsor, PA	4 beds \| 2 baths \| 2,953 sq.ft.	$493,763	Airbnb cash on cash: -1.77% Traditional cash on cash: 1.25% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.77% Traditional ROI: 1.25%
Addison Plan Windsor, PA	4 beds \| 2 baths \| 2,595 sq.ft.	$478,290	Airbnb cash on cash: -1.75% Traditional cash on cash: 1.37% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.75% Traditional ROI: 1.37%
Nottingham Plan Windsor, PA	4 beds \| 2 baths \| 3,600 sq.ft.	$526,009	Airbnb cash on cash: -1.82% Traditional cash on cash: 0.93% Airbnb Rental Income: $779 Traditional Rental Income: $1814 Airbnb ROI: -1.82% Traditional ROI: 0.93%
Lachlan Plan Windsor, PA	4 beds \| 2 baths \| 2,346 sq.ft.	$465,697	Airbnb cash on cash: -1.72% Traditional cash on cash: 1.76% Airbnb Rental Income: $779 Traditional Rental Income: $1978 Airbnb ROI: -1.72% Traditional ROI: 1.76%
Woodford Plan Windsor, PA	3 beds \| 2 baths \| 2,468 sq.ft.	$472,060	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.49% Airbnb Rental Income: $1480 Traditional Rental Income: $2325 Airbnb ROI: -0.41% Traditional ROI: 2.49%
Ethan Plan Windsor, PA	4 beds \| 2 baths \| 3,211 sq.ft.	$498,032	Airbnb cash on cash: -1.78% Traditional cash on cash: 1.22% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.78% Traditional ROI: 1.22%
Devonshire Plan Windsor, PA Devonshire Plan, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 4,016 sq.ft.	$548,418	Airbnb cash on cash: -1.85% Traditional cash on cash: 0.79% Airbnb Rental Income: $779 Traditional Rental Income: $1814 Airbnb ROI: -1.85% Traditional ROI: 0.79%
Covington Plan Windsor, PA	4 beds \| 2 baths \| 3,405 sq.ft.	$506,570	Airbnb cash on cash: -1.79% Traditional cash on cash: 1.07% Airbnb Rental Income: $779 Traditional Rental Income: $1814 Airbnb ROI: -1.79% Traditional ROI: 1.07%
Brentwood Plan Windsor, PA	4 beds \| 2 baths \| 2,074 sq.ft.	$446,541	Airbnb cash on cash: -1.69% Traditional cash on cash: 1.65% Airbnb Rental Income: $779 Traditional Rental Income: $1855 Airbnb ROI: -1.69% Traditional ROI: 1.65%
1155 Gebhart Rd Lot B Windsor, PA 1155 Gebhart Rd Lot B, Windsor, PA 17366 \| Other	N/A beds \| N/A baths \| N/A	$79,900	Airbnb cash on cash: 8.12% Traditional cash on cash: 2.63% Airbnb Rental Income: $1342 Traditional Rental Income: $498 Airbnb ROI: 8.12% Traditional ROI: 2.63%

Real Estate investment in Windsor, PA

There are 33 properties for sale in the city of Windsor . The median list price in Windsor is $596,000 and the average price per square foot is $190. In January 2026, the average monthly cash on cash return in Windsor is 2.00%. The average monthly rental income in Windsor is $1,991.

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

There are 33 investment properties available for sale in Windsor.

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

The ROI for Long-Term is higher than the Short-Term in Windsor with average rental income of $1,991.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, PA

2402 CRALEY Road

Windsor, PA

3 beds | 2 baths | 1,713 sq.ft.

$297,500

Airbnb cash on cash: 0.91%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $1480

Traditional Rental Income: $2241

Airbnb ROI: 0.91%

Traditional ROI: 5.18%

333 NEWCOMER RD

Windsor, PA

4 beds | 3 baths | 2,488 sq.ft.

$949,900

Airbnb cash on cash: -1.72%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $779

Traditional Rental Income: $3095

Airbnb ROI: -1.72%

Traditional ROI: 1.26%

10 AZALEA Drive

Windsor, PA

3 beds | 2 baths | 3,185 sq.ft.

$465,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $1480

Traditional Rental Income: $2092

Airbnb ROI: -0.5%

Traditional ROI: 1.91%

88 E MAIN Street

Windsor, PA

2 beds | 1 baths | 1,440 sq.ft.

$199,900

Airbnb cash on cash: -1.02%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $652

Traditional Rental Income: $1484

Airbnb ROI: -1.02%

Traditional ROI: 4.94%

2 Windsor Acrs

Windsor, PA

2 beds | 1 baths | 800 sq.ft.

$59,500

Airbnb cash on cash: 1.87%

Traditional cash on cash: 10.89%

Airbnb Rental Income: $652

Traditional Rental Income: $893

Airbnb ROI: 1.87%

Traditional ROI: 10.89%

42 Water St

Windsor, PA

4 beds | 2 baths | 1,686 sq.ft.

$199,900

Airbnb cash on cash: -0.62%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $779

Traditional Rental Income: $1855

Airbnb ROI: -0.62%

Traditional ROI: 6.73%

307 Boxwood Dr

Windsor, PA

4 beds | 2 baths | 2,277 sq.ft.

$451,990

Airbnb cash on cash: -1.78%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $779

Traditional Rental Income: $2055

Airbnb ROI: -1.78%

Traditional ROI: 1.98%

311 Boxwood Dr

Windsor, PA

4 beds | 2 baths | 2,277 sq.ft.

$455,990

Airbnb cash on cash: -1.79%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $779

Traditional Rental Income: $2058

Airbnb ROI: -1.79%