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
57 2nd St Windsor, PA Cute rancher with updated kitchen, brand new bath, new vinyl plank flooring, plus all new ...	2 beds \| 1 baths \| 1,045 sq.ft.	$245,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 4.61% Airbnb Rental Income: $1966 Traditional Rental Income: $1637 Airbnb ROI: 3.8% Traditional ROI: 4.61%
1883 Craley Rd Windsor, PA Step foot into this beautiful, recently remodeled, 4 bedroom, 2 bath home, in Eastern scho...	4 beds \| 2 baths \| 1,696 sq.ft.	$295,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 5.53% Airbnb Rental Income: $2808 Traditional Rental Income: $2170 Airbnb ROI: 5.46% Traditional ROI: 5.53%
40 2nd St Windsor, PA Charming Home in quaint town of Windsor is just what you're looking for: spacious, open r...	4 beds \| 1 baths \| 2,151 sq.ft.	$274,900	Airbnb cash on cash: 5.84% Traditional cash on cash: 4.74% Airbnb Rental Income: $2808 Traditional Rental Income: $1865 Airbnb ROI: 5.84% Traditional ROI: 4.74%
333 Newcomer Rd Windsor, PA Nestled on nearly 8 picturesque acres, this exceptional property offers the perfect blend ...	4 beds \| 2 baths \| 2,488 sq.ft.	$885,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 1.35% Airbnb Rental Income: $2808 Traditional Rental Income: $3095 Airbnb ROI: 0.2% Traditional ROI: 1.35%
307 Boxwood Dr Windsor, PA 307 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$404,990	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.51% Airbnb Rental Income: $2808 Traditional Rental Income: $2055 Airbnb ROI: 2.76% Traditional ROI: 2.51%
311 Boxwood Dr Windsor, PA 311 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$409,990	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.45% Airbnb Rental Income: $2808 Traditional Rental Income: $2058 Airbnb ROI: 2.7% Traditional ROI: 2.45%
100 Schoolhouse Ln #MAGNOLIA Windsor, PA 100 Schoolhouse Ln #MAGNOLIA, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,953 sq.ft.	$502,503	Airbnb cash on cash: 1.73% Traditional cash on cash: 1.82% Airbnb Rental Income: $2808 Traditional Rental Income: $2191 Airbnb ROI: 1.73% Traditional ROI: 1.82%
309 Boxwood Dr Windsor, PA 309 Boxwood Dr, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,277 sq.ft.	$399,990	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.56% Airbnb Rental Income: $2808 Traditional Rental Income: $2053 Airbnb ROI: 2.82% Traditional ROI: 2.56%
100 Schoolhouse Ln #HAWTHORNE Windsor, PA 100 Schoolhouse Ln #HAWTHORNE, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 3,646 sq.ft.	$528,778	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.07% Airbnb Rental Income: $2808 Traditional Rental Income: $1929 Airbnb ROI: 1.52% Traditional ROI: 1.07%
Caldwell Plan Windsor, PA	3 beds \| 2 baths \| 1,664 sq.ft.	$441,843	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.33% Airbnb Rental Income: $2598 Traditional Rental Income: $1705 Airbnb ROI: 1.99% Traditional ROI: 1.33%
Harrison Plan Windsor, PA	3 beds \| 2 baths \| 2,002 sq.ft.	$456,328	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.53% Airbnb Rental Income: $2598 Traditional Rental Income: $1841 Airbnb ROI: 1.84% Traditional ROI: 1.53%
100 Schoolhouse Ln #SEBASTIAN Windsor, PA 100 Schoolhouse Ln #SEBASTIAN, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,701 sq.ft.	$485,856	Airbnb cash on cash: 1.88% Traditional cash on cash: 1.86% Airbnb Rental Income: $2808 Traditional Rental Income: $2140 Airbnb ROI: 1.88% Traditional ROI: 1.86%
Arcadia Plan Windsor, PA Arcadia Plan, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 1,982 sq.ft.	$496,685	Airbnb cash on cash: 1.49% Traditional cash on cash: 1.2% Airbnb Rental Income: $2598 Traditional Rental Income: $1841 Airbnb ROI: 1.49% Traditional ROI: 1.2%
Kipling Plan Windsor, PA Kipling Plan, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 2,837 sq.ft.	$524,042	Airbnb cash on cash: 1.28% Traditional cash on cash: 1.09% Airbnb Rental Income: $2598 Traditional Rental Income: $1884 Airbnb ROI: 1.28% Traditional ROI: 1.09%
100 Schoolhouse Ln #COVINGTON Windsor, PA 100 Schoolhouse Ln #COVINGTON, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 3,405 sq.ft.	$515,310	Airbnb cash on cash: 1.63% Traditional cash on cash: 1.17% Airbnb Rental Income: $2808 Traditional Rental Income: $1929 Airbnb ROI: 1.63% Traditional ROI: 1.17%
100 Schoolhouse Ln #LACHLAN Windsor, PA 100 Schoolhouse Ln #LACHLAN, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,346 sq.ft.	$474,437	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.81% Airbnb Rental Income: $2808 Traditional Rental Income: $2073 Airbnb ROI: 1.99% Traditional ROI: 1.81%
100 Schoolhouse Ln #ADDISON Windsor, PA 100 Schoolhouse Ln #ADDISON, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 2,594 sq.ft.	$487,030	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.77% Airbnb Rental Income: $2808 Traditional Rental Income: $2104 Airbnb ROI: 1.87% Traditional ROI: 1.77%
Parker Plan Windsor, PA	4 beds \| 2 baths \| 2,705 sq.ft.	$484,256	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.74% Airbnb Rental Income: $2808 Traditional Rental Income: $2043 Airbnb ROI: 1.98% Traditional ROI: 1.74%
100 Schoolhouse Ln #ANDREWS Windsor, PA 100 Schoolhouse Ln #ANDREWS, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 1,819 sq.ft.	$450,212	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.61% Airbnb Rental Income: $2598 Traditional Rental Income: $1892 Airbnb ROI: 1.81% Traditional ROI: 1.61%
Andrews Plan Windsor, PA	3 beds \| 2 baths \| 1,819 sq.ft.	$450,212	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.38% Airbnb Rental Income: $2598 Traditional Rental Income: $1758 Airbnb ROI: 1.9% Traditional ROI: 1.38%
Sebastian Plan Windsor, PA	4 beds \| 2 baths \| 2,701 sq.ft.	$485,856	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.72% Airbnb Rental Income: $2808 Traditional Rental Income: $2043 Airbnb ROI: 1.96% Traditional ROI: 1.72%
Magnolia Plan Windsor, PA	4 beds \| 2 baths \| 2,953 sq.ft.	$502,503	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.67% Airbnb Rental Income: $2808 Traditional Rental Income: $2083 Airbnb ROI: 1.81% Traditional ROI: 1.67%
Addison Plan Windsor, PA	4 beds \| 2 baths \| 2,595 sq.ft.	$487,030	Airbnb cash on cash: 1.95% Traditional cash on cash: 1.64% Airbnb Rental Income: $2808 Traditional Rental Income: $2007 Airbnb ROI: 1.95% Traditional ROI: 1.64%
Nottingham Plan Windsor, PA	4 beds \| 2 baths \| 3,600 sq.ft.	$534,749	Airbnb cash on cash: 1.55% Traditional cash on cash: 0.88% Airbnb Rental Income: $2808 Traditional Rental Income: $1814 Airbnb ROI: 1.55% Traditional ROI: 0.88%
Lachlan Plan Windsor, PA	4 beds \| 2 baths \| 2,346 sq.ft.	$474,437	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.68% Airbnb Rental Income: $2808 Traditional Rental Income: $1978 Airbnb ROI: 2.07% Traditional ROI: 1.68%
Woodford Plan Windsor, PA	3 beds \| 2 baths \| 2,468 sq.ft.	$480,800	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.42% Airbnb Rental Income: $2598 Traditional Rental Income: $1888 Airbnb ROI: 1.62% Traditional ROI: 1.42%
Ethan Plan Windsor, PA	4 beds \| 2 baths \| 3,211 sq.ft.	$506,772	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.07% Airbnb Rental Income: $2808 Traditional Rental Income: $1814 Airbnb ROI: 1.78% Traditional ROI: 1.07%
Devonshire Plan Windsor, PA Devonshire Plan, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 4,016 sq.ft.	$557,158	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.74% Airbnb Rental Income: $2808 Traditional Rental Income: $1814 Airbnb ROI: 1.39% Traditional ROI: 0.74%
Covington Plan Windsor, PA Covington Plan, Windsor, PA 17366 \| Single Family Residential	4 beds \| 2 baths \| 3,405 sq.ft.	$515,310	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.01% Airbnb Rental Income: $2808 Traditional Rental Income: $1814 Airbnb ROI: 1.71% Traditional ROI: 1.01%
Brentwood Plan Windsor, PA	4 beds \| 2 baths \| 2,074 sq.ft.	$455,281	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.79% Airbnb Rental Income: $2808 Traditional Rental Income: $1948 Airbnb ROI: 2.26% Traditional ROI: 1.79%
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: 0.91% Traditional cash on cash: 2.63% Airbnb Rental Income: $662 Traditional Rental Income: $498 Airbnb ROI: 0.91% Traditional ROI: 2.63%
215 Azalea Dr Windsor, PA Over 4,000 finished sq. ft! Seeing is believing! Buy with confidence - the home recently a...	4 beds \| 3 baths \| 4,722 sq.ft.	$429,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 5.62% Airbnb Rental Income: $2808 Traditional Rental Income: $3645 Airbnb ROI: 1.9% Traditional ROI: 5.62%
1025 White Oak Rd Windsor, PA SIX. CAR. GARAGE. I could stop there, but I won't...Welcome to 1025 White Oak Rd, where pr...	3 beds \| 2 baths \| 1,716 sq.ft.	$545,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.26% Airbnb Rental Income: $2598 Traditional Rental Income: $2321 Airbnb ROI: 1.58% Traditional ROI: 2.26%
1685 Bahns Mill Rd Windsor, PA Welcome to 1685 Bahns Mill Road-an exceptional private estate set on 7.56 scenic acres in ...	4 beds \| 3 baths \| 6,310 sq.ft.	$1,050,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 1.79% Airbnb Rental Income: $2808 Traditional Rental Income: $4061 Airbnb ROI: -0.16% Traditional ROI: 1.79%
30-34 Abby Rd Windsor, PA 30-34 Abby Rd, Windsor, PA 17366 \| Other	N/A beds \| N/A baths \| N/A	$139,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 1% Airbnb Rental Income: $662 Traditional Rental Income: $568 Airbnb ROI: -0.53% Traditional ROI: 1%
1708 Manor Rd Windsor, PA 1708 Manor Rd, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 1,352 sq.ft.	$309,900	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.79% Airbnb Rental Income: $2598 Traditional Rental Income: $1654 Airbnb ROI: 3.9% Traditional ROI: 2.79%
325 Thomas Armor Dr Windsor, PA Welcome home to the highly sought-after Chatham Creek community, where opportunities like ...	4 beds \| 2 baths \| 3,707 sq.ft.	$449,990	Airbnb cash on cash: 2.16% Traditional cash on cash: 3.14% Airbnb Rental Income: $2808 Traditional Rental Income: $2563 Airbnb ROI: 2.16% Traditional ROI: 3.14%
185 Biglar Ct Windsor, PA Welcome home to this meticulously maintained rancher offering the perfect combination of c...	3 beds \| 2 baths \| 1,545 sq.ft.	$325,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 4.12% Airbnb Rental Income: $2598 Traditional Rental Income: $2180 Airbnb ROI: 3.45% Traditional ROI: 4.12%
100 Fawn Circle Dr Windsor, PA 100 Fawn Circle Dr, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 924 sq.ft.	$160,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 7.4% Airbnb Rental Income: $2598 Traditional Rental Income: $1614 Airbnb ROI: 9.77% Traditional ROI: 7.4%
Berkeley Plan Windsor, PA Berkeley Plan, Windsor, PA 17366 \| Single Family Residential	3 beds \| 2 baths \| 2,404 sq.ft.	$494,692	Airbnb cash on cash: 1.5% Traditional cash on cash: 1.46% Airbnb Rental Income: $2598 Traditional Rental Income: $1955 Airbnb ROI: 1.5% Traditional ROI: 1.46%

Real Estate investment in Windsor, PA

There are 46 properties for sale in the city of Windsor . The median list price in Windsor is $246,328 and the average price per square foot is $79. In October 2026, the average monthly cash on cash return in Windsor is 2.00%. The average monthly rental income in Windsor is $2,054.

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

There are 46 investment properties available for sale in Windsor.

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

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $2,808.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, PA

57 2nd St

Windsor, PA

2 beds | 1 baths | 1,045 sq.ft.

$245,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $1966

Traditional Rental Income: $1637

Airbnb ROI: 3.8%

Traditional ROI: 4.61%

1883 Craley Rd

Windsor, PA

4 beds | 2 baths | 1,696 sq.ft.

$295,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 5.53%

Airbnb Rental Income: $2808

Traditional Rental Income: $2170

Airbnb ROI: 5.46%

Traditional ROI: 5.53%

40 2nd St

Windsor, PA

4 beds | 1 baths | 2,151 sq.ft.

$274,900

Airbnb cash on cash: 5.84%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $2808

Traditional Rental Income: $1865

Airbnb ROI: 5.84%

Traditional ROI: 4.74%

333 Newcomer Rd

Windsor, PA

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

$885,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $2808

Traditional Rental Income: $3095

Airbnb ROI: 0.2%

Traditional ROI: 1.35%

307 Boxwood Dr

Windsor, PA

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

$404,990

Airbnb cash on cash: 2.76%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2808

Traditional Rental Income: $2055

Airbnb ROI: 2.76%

Traditional ROI: 2.51%

311 Boxwood Dr

Windsor, PA

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

$409,990

Airbnb cash on cash: 2.7%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $2808

Traditional Rental Income: $2058

Airbnb ROI: 2.7%

Traditional ROI: 2.45%

100 Schoolhouse Ln #MAGNOLIA

Windsor, PA

4 beds | 2 baths | 2,953 sq.ft.

$502,503

Airbnb cash on cash: 1.73%

Traditional cash on cash: 1.82%

Airbnb Rental Income: $2808

Traditional Rental Income: $2191

Airbnb ROI: 1.73%

Traditional ROI: 1.82%

309 Boxwood Dr

Windsor, PA

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

$399,990

Airbnb cash on cash: 2.82%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $2808

Traditional Rental Income: $2053

Airbnb ROI: 2.82%