Real Estate Investment Properties for Sale in Windsor, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
214 Augusta Rockland Road Windsor, ME This beautiful contemporary 3 bedroom/2.5 bath home offers over 2,500 SF of living space d...	3 beds \| 4 baths \| N/A	$700,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 5.27% Airbnb Rental Income: $1600 Traditional Rental Income: $4463 Airbnb ROI: 0.19% Traditional ROI: 5.27%
70 Greeley Road Windsor, ME This classic Maine farmhouse has it all. If you are looking for a quiet lifestyle that's o...	4 beds \| N/A baths \| 1,935 sq.ft.	$534,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $3753 Airbnb ROI: N/A Traditional ROI: 5.86%
20 Pit Road Windsor, ME Beautiful 1997, fully updated four bedroom home on 3.4 acres in Windsor. Super low energy ...	3 beds \| N/A baths \| 2,240 sq.ft.	$450,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 7.28% Airbnb Rental Income: $1600 Traditional Rental Income: $3587 Airbnb ROI: 1.48% Traditional ROI: 7.28%
282 Pierces Point Road Windsor, ME Location, Location - Privacy, Privacy! WATER FRONT YEAR ROUND Tucked away on 2.5 private...	3 beds \| N/A baths \| 2,474 sq.ft.	$779,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.26% Airbnb Rental Income: $1600 Traditional Rental Income: $3780 Airbnb ROI: -0.37% Traditional ROI: 3.26%
3 Stone Hedge Lane Windsor, ME Brand new - currently under construction- 3 bedroom, 2 bath ranch in a peaceful subdivisio...	3 beds \| N/A baths \| 1,302 sq.ft.	$349,900	Airbnb cash on cash: 2.01% Traditional cash on cash: 7.9% Airbnb Rental Income: $1600 Traditional Rental Income: $3078 Airbnb ROI: 2.01% Traditional ROI: 7.9%
24 Taylor Road Windsor, ME Very comfortable 1 floor living with this brand new 1680 square foot home. Offering 3 bedr...	3 beds \| N/A baths \| 1,680 sq.ft.	$414,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 6.06% Airbnb Rental Income: $1600 Traditional Rental Income: $3360 Airbnb ROI: 0.36% Traditional ROI: 6.06%
25 Rockwood Estates Windsor, ME Custom Built Ranch Style Home in a Great Location in one of Windsor's Best New Subdivision...	3 beds \| N/A baths \| 1,477 sq.ft.	$419,899	Airbnb cash on cash: 0.21% Traditional cash on cash: 5.45% Airbnb Rental Income: $1600 Traditional Rental Income: $3206 Airbnb ROI: 0.21% Traditional ROI: 5.45%
21 Rockwood Estates Windsor, ME This home is now completely finished and ready for it's new owner! Custom Built Colonial S...	3 beds \| 3 baths \| 1,430 sq.ft.	$435,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 5.69% Airbnb Rental Income: $1600 Traditional Rental Income: $3421 Airbnb ROI: 0.11% Traditional ROI: 5.69%
217 Reed Road Windsor, ME Looking for an investment? Look no further! This thoughtfully designed duplex in Windsor i...	N/A beds \| N/A baths \| 1,700 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 4.64%

Real Estate investment in Windsor, ME

There are 9 properties for sale in the city of Windsor . The median list price in Windsor is $442,950 and the average price per square foot is $254. In October 2025, the average monthly cash on cash return in Windsor is 6.00%. The average monthly rental income in Windsor is $3,391.

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

There are 9 investment properties available for sale in Windsor.

In 2025, 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 $1,600.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, ME

214 Augusta Rockland Road

Windsor, ME

3 beds | 4 baths | N/A

$700,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $1600

Traditional Rental Income: $4463

Airbnb ROI: 0.19%

Traditional ROI: 5.27%

70 Greeley Road

Windsor, ME

4 beds | N/A baths | 1,935 sq.ft.

$534,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3753

Airbnb ROI: N/A

Traditional ROI: 5.86%

20 Pit Road

Windsor, ME

3 beds | N/A baths | 2,240 sq.ft.

$450,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 7.28%

Airbnb Rental Income: $1600

Traditional Rental Income: $3587

Airbnb ROI: 1.48%

Traditional ROI: 7.28%

282 Pierces Point Road

Windsor, ME

3 beds | N/A baths | 2,474 sq.ft.

$779,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $1600

Traditional Rental Income: $3780

Airbnb ROI: -0.37%

Traditional ROI: 3.26%

3 Stone Hedge Lane

Windsor, ME

3 beds | N/A baths | 1,302 sq.ft.

$349,900

Airbnb cash on cash: 2.01%

Traditional cash on cash: 7.9%

Airbnb Rental Income: $1600

Traditional Rental Income: $3078

Airbnb ROI: 2.01%

Traditional ROI: 7.9%

24 Taylor Road

Windsor, ME

3 beds | N/A baths | 1,680 sq.ft.

$414,900

Airbnb cash on cash: 0.36%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $1600

Traditional Rental Income: $3360

Airbnb ROI: 0.36%

Traditional ROI: 6.06%

25 Rockwood Estates

Windsor, ME

3 beds | N/A baths | 1,477 sq.ft.

$419,899

Airbnb cash on cash: 0.21%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $1600

Traditional Rental Income: $3206

Airbnb ROI: 0.21%

Traditional ROI: 5.45%

21 Rockwood Estates

Windsor, ME

3 beds | 3 baths | 1,430 sq.ft.

$435,900

Airbnb cash on cash: 0.11%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1600

Traditional Rental Income: $3421

Airbnb ROI: 0.11%