Real Estate Investment Properties for Sale in Windham, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
29 Victoria Lane Windham, ME This beautifully designed sprawling ranch offers a functional and inviting layout. The pri...	4 beds \| N/A baths \| 3,128 sq.ft.	$854,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.23% Airbnb Rental Income: $2909 Traditional Rental Income: $4139 Airbnb ROI: 0.84% Traditional ROI: 3.23%
99 Land Of Nod Road Windham, ME Move in ready & neat as a pin! A 'must see' on the list!...This 2003, custom...	3 beds \| 3 baths \| 2,831 sq.ft.	$767,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 3.33% Airbnb Rental Income: $2516 Traditional Rental Income: $3879 Airbnb ROI: 0.57% Traditional ROI: 3.33%
37 Swan Road Windham, ME SHARED DEEDED HIGHLAND LAKE FRONTAGE Welcome to 37 Swan Road, a charming year round home ...	3 beds \| N/A baths \| 1,938 sq.ft.	$419,900	Airbnb cash on cash: 2.91% Traditional cash on cash: 5.6% Airbnb Rental Income: $2516 Traditional Rental Income: $2966 Airbnb ROI: 2.91% Traditional ROI: 5.6%
11 Belvedere Drive Windham, ME This standout Colonial delivers space, light, and modern comfort in a location that keeps ...	3 beds \| N/A baths \| 1,736 sq.ft.	$560,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.42% Airbnb Rental Income: $2516 Traditional Rental Income: $2793 Airbnb ROI: 1.73% Traditional ROI: 3.42%
81 Hall Road Windham, ME Move-in ready and recently remodeled, this low-maintenance Windham split-entry sits on jus...	4 beds \| N/A baths \| 1,429 sq.ft.	$467,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 1.86% Airbnb Rental Income: $2909 Traditional Rental Income: $1932 Airbnb ROI: 2.55% Traditional ROI: 1.86%
3 Lilac Lane Windham, ME Taxes TBD.	3 beds \| N/A baths \| 1,636 sq.ft.	$525,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 5.66% Airbnb Rental Income: $2516 Traditional Rental Income: $3366 Airbnb ROI: 2.69% Traditional ROI: 5.66%
30 Marshall Valley Road Windham, ME Build Your Dream Home With One Of Maines's Premier Builders!! Welcome To 30 Marshall Valle...	3 beds \| N/A baths \| 1,620 sq.ft.	$550,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.24% Airbnb Rental Income: $2516 Traditional Rental Income: $3306 Airbnb ROI: 2.52% Traditional ROI: 5.24%
103 Basin Road Windham, ME This a great opportunity to own a classic lakeside home on the shores of the Sebago Lake B...	2 beds \| N/A baths \| 813 sq.ft.	$1,000,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.22% Airbnb Rental Income: $3089 Traditional Rental Income: $2177 Airbnb ROI: 1.44% Traditional ROI: 1.22%
19 Moss Road Windham, ME Welcome to 19 Moss Road, a remodeled four bedroom, three bathroom home complete with a two...	4 beds \| N/A baths \| 2,170 sq.ft.	$500,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.81% Airbnb Rental Income: $2909 Traditional Rental Income: $3907 Airbnb ROI: 2.23% Traditional ROI: 5.81%
1083 Roosevelt Trail Windham, ME Welcome to this charming 3-bedroom, 1.5-bath home offering comfort, style, and convenience...	4 beds \| N/A baths \| 1,586 sq.ft.	$380,000	Airbnb cash on cash: 5% Traditional cash on cash: 8.27% Airbnb Rental Income: $2909 Traditional Rental Income: $3403 Airbnb ROI: 5% Traditional ROI: 8.27%
66 James Way Windham, ME Versatile Quonset Hut-Style Building - Live & Work Opportunity. Discover a unique chance ...	1 beds \| N/A baths \| 2,674 sq.ft.	$299,900	Airbnb cash on cash: 2.32% Traditional cash on cash: 6.32% Airbnb Rental Income: $1470 Traditional Rental Income: $2164 Airbnb ROI: 2.32% Traditional ROI: 6.32%
763 River Road Windham, ME Move right into this beautifully updated 2-bedroom, 1-bath home, perfectly blending comfor...	2 beds \| N/A baths \| 1,120 sq.ft.	$375,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 4.89% Airbnb Rental Income: $3089 Traditional Rental Income: $2169 Airbnb ROI: 5.5% Traditional ROI: 4.89%
324 Roosevelt Trail unit: A-B #A-B Windham, ME Rare opportunity for the creative. Currently property consists of a ranch style duplex wit...	N/A beds \| N/A baths \| 1,408 sq.ft.	$565,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.12% Airbnb Rental Income: $671 Traditional Rental Income: $2160 Airbnb ROI: -1.27% Traditional ROI: 2.12%
16 Shepherd Lane Windham, ME Welcome to Shepherd Lane, Windham's newest subdivision! Located off Falmouth Road, Shepher...	3 beds \| N/A baths \| 1,352 sq.ft.	$475,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 5.01% Airbnb Rental Income: $2516 Traditional Rental Income: $2768 Airbnb ROI: 3.07% Traditional ROI: 5.01%
14 Sabbady Point Road Windham, ME 4 Sabbady Point Road recently remodeled home with updates and a 2 car garage. This afforda...	2 beds \| N/A baths \| 1,008 sq.ft.	$274,500	Airbnb cash on cash: 7.84% Traditional cash on cash: 7.41% Airbnb Rental Income: $3089 Traditional Rental Income: $2274 Airbnb ROI: 7.84% Traditional ROI: 7.41%
336 Pope Road Windham, ME Nestled in private, wooded enclave, this peaceful and charming 2-bedroom, 1-bath condo is ...	2 beds \| N/A baths \| 1,010 sq.ft.	$269,900	Airbnb cash on cash: 7.98% Traditional cash on cash: 7.41% Airbnb Rental Income: $3089 Traditional Rental Income: $2240 Airbnb ROI: 7.98% Traditional ROI: 7.41%
15 Read Road Windham, ME 1840's home with lots of charm. Level lot with lots of fruit trees. Detached shed/barn. Th...	3 beds \| N/A baths \| 1,784 sq.ft.	$375,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 5.12% Airbnb Rental Income: $2516 Traditional Rental Income: $2720 Airbnb ROI: 2.81% Traditional ROI: 5.12%
8 Staples Lane Windham, ME Welcome Home to 8 Staples Lane, Windham! This isn't just a house; it's a beautifully renov...	3 beds \| N/A baths \| 1,500 sq.ft.	$435,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 5.77% Airbnb Rental Income: $2516 Traditional Rental Income: $2856 Airbnb ROI: 3.44% Traditional ROI: 5.77%
18 Victoria Lane Windham, ME Welcome to 18 Victoria Lane Ã¢â¬â an immaculately maintained home offering generous liv...	4 beds \| N/A baths \| 3,049 sq.ft.	$830,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.95% Airbnb Rental Income: $2909 Traditional Rental Income: $3147 Airbnb ROI: 1.77% Traditional ROI: 2.95%
26 Marshall Valley Road Windham, ME Great Opportunity, Motivated Sellers, In An Amazing Windham Location!! Welcome to 26 Marsh...	2 beds \| N/A baths \| 2,703 sq.ft.	$540,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.34% Airbnb Rental Income: $3089 Traditional Rental Income: $2286 Airbnb ROI: 3.53% Traditional ROI: 3.34%
7 Baxter Woods Trail Windham, ME Don't miss this charming 2BR, 1.5BA townhouse-style condo nestled in a peaceful wooded set...	2 beds \| N/A baths \| 910 sq.ft.	$275,000	Airbnb cash on cash: 7.82% Traditional cash on cash: 6.57% Airbnb Rental Income: $3089 Traditional Rental Income: $2061 Airbnb ROI: 7.82% Traditional ROI: 6.57%
3 Peavey Avenue Windham, ME Ranch style home with 3 bedrooms, located on a corner lot, in a quiet neighborhood within ...	3 beds \| N/A baths \| 1,464 sq.ft.	$369,900	Airbnb cash on cash: 4.21% Traditional cash on cash: 6.58% Airbnb Rental Income: $2516 Traditional Rental Income: $2729 Airbnb ROI: 4.21% Traditional ROI: 6.58%
80 Sky Drive Windham, ME WINDHAM: Discover refined living in this exceptional new construction Colonial, offering 2...	3 beds \| N/A baths \| 2,650 sq.ft.	$949,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.91% Airbnb Rental Income: $2516 Traditional Rental Income: $2977 Airbnb ROI: -0.3% Traditional ROI: 0.91%
7 Haven Road Windham, ME Newly completed Windham home is located only minutes to Portland in an established neighbo...	3 beds \| N/A baths \| 1,792 sq.ft.	$565,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 4.3% Airbnb Rental Income: $2516 Traditional Rental Income: $2897 Airbnb ROI: 2.43% Traditional ROI: 4.3%
18 Shepherd Lane Windham, ME Welcome to Shepherd Lane, Windham's newest subdivision! Located off Falmouth Road, Shepher...	3 beds \| N/A baths \| 1,706 sq.ft.	$525,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.2% Airbnb Rental Income: $2516 Traditional Rental Income: $3308 Airbnb ROI: 1.35% Traditional ROI: 4.2%
1 Friendly Way Windham, ME Welcome to 1 Friendly Way Ã¢â¬â South Windham's newly built, luxury modern-style bungal...	3 beds \| N/A baths \| 2,016 sq.ft.	$765,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.64% Airbnb Rental Income: $2516 Traditional Rental Income: $2941 Airbnb ROI: 0.19% Traditional ROI: 1.64%
1 Matinicus Way Windham, ME Welcome to 1 Matinicus Way Ã¢â¬â a charming, low-maintenance single level condo offerin...	2 beds \| N/A baths \| 767 sq.ft.	$390,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 5.4% Airbnb Rental Income: $3089 Traditional Rental Income: $2437 Airbnb ROI: 5.25% Traditional ROI: 5.4%
114 Highland Cliff Road Windham, ME Another SHEEBEO SIGNATURE HOME just completed, ready for you! Situated on an elevated 2-a...	3 beds \| N/A baths \| 2,200 sq.ft.	$769,500	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.55% Airbnb Rental Income: $2516 Traditional Rental Income: $2892 Airbnb ROI: 0.18% Traditional ROI: 1.55%
18 Cook Road Windham, ME Move in ready at its finest! Set on a private lot, in a great location, this home is ready...	3 beds \| N/A baths \| 1,304 sq.ft.	$499,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 4.58% Airbnb Rental Income: $2516 Traditional Rental Income: $2700 Airbnb ROI: 2.88% Traditional ROI: 4.58%

Real Estate investment in Windham, ME

There are 29 properties for sale in the city of Windham . The median list price in Windham is $499,500 and the average price per square foot is $285. In December 2025, the average monthly cash on cash return in Windham is 5.00%. The average monthly rental income in Windham is $2,793.

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

There are 29 investment properties available for sale in Windham.

In 2025, the best neighborhood to buy investment property is Windham.

The ROI for Long-Term is higher than the Short-Term in Windham with average rental income of $2,793.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, ME

29 Victoria Lane

Windham, ME

4 beds | N/A baths | 3,128 sq.ft.

$854,900

Airbnb cash on cash: 0.84%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2909

Traditional Rental Income: $4139

Airbnb ROI: 0.84%

Traditional ROI: 3.23%

99 Land Of Nod Road

Windham, ME

3 beds | 3 baths | 2,831 sq.ft.

$767,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2516

Traditional Rental Income: $3879

Airbnb ROI: 0.57%

Traditional ROI: 3.33%

37 Swan Road

Windham, ME

3 beds | N/A baths | 1,938 sq.ft.

$419,900

Airbnb cash on cash: 2.91%

Traditional cash on cash: 5.6%

Airbnb Rental Income: $2516

Traditional Rental Income: $2966

Airbnb ROI: 2.91%

Traditional ROI: 5.6%

11 Belvedere Drive

Windham, ME

3 beds | N/A baths | 1,736 sq.ft.

$560,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $2516

Traditional Rental Income: $2793

Airbnb ROI: 1.73%

Traditional ROI: 3.42%

81 Hall Road

Windham, ME

4 beds | N/A baths | 1,429 sq.ft.

$467,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $2909

Traditional Rental Income: $1932

Airbnb ROI: 2.55%

Traditional ROI: 1.86%

3 Lilac Lane

Windham, ME

3 beds | N/A baths | 1,636 sq.ft.

$525,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $2516

Traditional Rental Income: $3366

Airbnb ROI: 2.69%

Traditional ROI: 5.66%

30 Marshall Valley Road

Windham, ME

3 beds | N/A baths | 1,620 sq.ft.

$550,000

Airbnb cash on cash: 2.52%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $2516

Traditional Rental Income: $3306

Airbnb ROI: 2.52%

Traditional ROI: 5.24%

103 Basin Road

Windham, ME

2 beds | N/A baths | 813 sq.ft.

$1,000,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $3089

Traditional Rental Income: $2177

Airbnb ROI: 1.44%