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.

Single Family Homes for Sale in Windham, ME

Search for Single Family Residential for Sale in Windham, Maine. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 51 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Twoey Dr Windham, ME Beautifully maintained split foyer home in excellent condition. Just 10 years old, this ho...	4 beds \| 2 baths \| 1,655 sq.ft.	$554,900	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.97% Airbnb Rental Income: $4051 Traditional Rental Income: $3517 Airbnb ROI: 4.33% Traditional ROI: 4.97%
214 Tandberg Trl Windham, ME Move in ready raised ranch with 3/4 bedrooms and two bathrooms. This home is on Tandberg T...	4 beds \| 2 baths \| 2,052 sq.ft.	$539,999	Airbnb cash on cash: 3.78% Traditional cash on cash: 4.62% Airbnb Rental Income: $4051 Traditional Rental Income: $3610 Airbnb ROI: 3.78% Traditional ROI: 4.62%
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: 0.64% Traditional cash on cash: 3.33% Airbnb Rental Income: $2581 Traditional Rental Income: $3879 Airbnb ROI: 0.64% Traditional ROI: 3.33%
104 Harvest Hill Rd Windham, ME Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concep...	3 beds \| 1 baths \| 1,164 sq.ft.	$520,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.25% Airbnb Rental Income: $2581 Traditional Rental Income: $2910 Airbnb ROI: 2.3% Traditional ROI: 4.25%
22 Montgomery Rd Windham, ME You will never find a setting like this! Owning over 300 ft of water frontage on 4 acres, ...	2 beds \| 2 baths \| 1,255 sq.ft.	$499,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.27% Airbnb Rental Income: $1554 Traditional Rental Income: $1926 Airbnb ROI: 0.52% Traditional ROI: 2.27%
20 Freeman Ct Windham, ME Set atop a private cul-de-sac in Windemere Estates community, 20 Freeman Court offers luxu...	4 beds \| 2 baths \| 4,602 sq.ft.	$1,485,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.64% Airbnb Rental Income: $4051 Traditional Rental Income: $4743 Airbnb ROI: 0.51% Traditional ROI: 1.64%
8 Environmental Way Windham, ME Welcome to Environmental Way with a contemporary flare and not your typical home! Surround...	3 beds \| 2 baths \| 2,024 sq.ft.	$499,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 3.02% Airbnb Rental Income: $2581 Traditional Rental Income: $2362 Airbnb ROI: 2.16% Traditional ROI: 3.02%
33 Spear Ave Windham, ME Move right into this well-maintained home, perfectly situated on a semi-private lot surrou...	3 beds \| 2 baths \| 1,518 sq.ft.	$419,900	Airbnb cash on cash: 3.06% Traditional cash on cash: 6.5% Airbnb Rental Income: $2581 Traditional Rental Income: $3318 Airbnb ROI: 3.06% Traditional ROI: 6.5%
80 Vista Dr Windham, ME Quiet, Lake Front 4-Season Home that can be yours to enjoy this summer. This three bedroo...	3 beds \| 1 baths \| 1,485 sq.ft.	$574,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 2.29% Airbnb Rental Income: $2581 Traditional Rental Income: $2362 Airbnb ROI: 1.54% Traditional ROI: 2.29%
44 Johnson Rd Windham, ME Luxury, Serenity, and Versatility Near Highland Lake Immerse yourself in a masterfully exe...	6 beds \| 5 baths \| 4,580 sq.ft.	$1,199,000	Airbnb cash on cash: 1.04% Traditional cash on cash: -0.33% Airbnb Rental Income: $4051 Traditional Rental Income: $1659 Airbnb ROI: 1.04% Traditional ROI: -0.33%
11 Belvedere Dr Windham, ME Well maintained and thoughtfully designed, this Colonial offers a functional layout, quali...	3 beds \| 2 baths \| 1,736 sq.ft.	$549,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.35% Airbnb Rental Income: $2581 Traditional Rental Income: $2793 Airbnb ROI: 1.73% Traditional ROI: 3.35%
36 Belvedere Dr Windham, ME Welcome to this meticulously maintained custom Colonial in Belvedere Estates - exactly wha...	3 beds \| 2 baths \| 1,962 sq.ft.	$575,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.21% Airbnb Rental Income: $2581 Traditional Rental Income: $2853 Airbnb ROI: 1.55% Traditional ROI: 3.21%
12 Arcadia Dr Windham, ME Welcome to your dream home nestled in the heart of the Brookhaven subdivision! This meticu...	4 beds \| 1 baths \| 2,623 sq.ft.	$529,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 2.82% Airbnb Rental Income: $4051 Traditional Rental Income: $2647 Airbnb ROI: 3.91% Traditional ROI: 2.82%
516 Falmouth Road Windham, ME BACK ON THE MARKET BY NO FAULT OF SELLER! Well-maintained and move-in ready, this bright a...	3 beds \| 2 baths \| 1,915 sq.ft.	$524,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.47% Airbnb Rental Income: $2581 Traditional Rental Income: $3187 Airbnb ROI: 1.98% Traditional ROI: 4.47%
32 Pennywhistle Dr Windham, ME This stunning home is bathed in natural light and beautifully appointed. It was purchased ...	3 beds \| 2 baths \| 2,600 sq.ft.	$829,500	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.47% Airbnb Rental Income: $2581 Traditional Rental Income: $3570 Airbnb ROI: 1.38% Traditional ROI: 3.47%
47 Running Brook Rd Windham, ME This 3 bedroom 1 bath ranch home is on a nice corner lot in a desireable neighborhood in t...	3 beds \| 1 baths \| 1,570 sq.ft.	$489,500	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.76% Airbnb Rental Income: $2581 Traditional Rental Income: $2650 Airbnb ROI: 2.26% Traditional ROI: 3.76%
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 \| 1 baths \| 813 sq.ft.	$850,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.6% Airbnb Rental Income: $1554 Traditional Rental Income: $2177 Airbnb ROI: 0.25% Traditional ROI: 1.6%
14 Emerson Dr Windham, ME Unique opportunity to own this 2005 built Contemporary located on Collins Pond with over 2...	4 beds \| 2 baths \| 3,444 sq.ft.	$499,900	Airbnb cash on cash: 4.27% Traditional cash on cash: 4.7% Airbnb Rental Income: $4051 Traditional Rental Income: $3391 Airbnb ROI: 4.27% Traditional ROI: 4.7%
594 River Road Rd Windham, ME 594 River Road Rd, Windham, ME 04062 \| Single Family Residential	2 beds \| 1 baths \| 780 sq.ft.	$1,060,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.49% Airbnb Rental Income: $1554 Traditional Rental Income: $1926 Airbnb ROI: -1.32% Traditional ROI: -0.49%
96 Mineral Spring Rd Windham, ME BACK ON THE MARKET! Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property wit...	6 beds \| 4 baths \| 2,940 sq.ft.	$559,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 1.33% Airbnb Rental Income: $4051 Traditional Rental Income: $2111 Airbnb ROI: 3.4% Traditional ROI: 1.33%
9 Shepherd Ln #13 Windham, ME Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and m...	3 beds \| 2 baths \| 1,632 sq.ft.	$494,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 5.76% Airbnb Rental Income: $2581 Traditional Rental Income: $3393 Airbnb ROI: 2.67% Traditional ROI: 5.76%
6 Shepherd Lane Windham, ME Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This...	3 beds \| 2 baths \| 1,632 sq.ft.	$499,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.81% Airbnb Rental Income: $2581 Traditional Rental Income: $3139 Airbnb ROI: 1.29% Traditional ROI: 3.81%
549 Roosevelt Trail Windham, ME New Price! Investor, builder, developers, home buyers! Exceptional opportunity on highly p...	1 beds \| 1 baths \| 798 sq.ft.	$339,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 4.37% Airbnb Rental Income: $1362 Traditional Rental Income: $1814 Airbnb ROI: 1.66% Traditional ROI: 4.37%
27 Independence Dr Windham, ME 4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built i...	4 beds \| 2 baths \| 2,746 sq.ft.	$875,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 0.51% Airbnb Rental Income: $4051 Traditional Rental Income: $2146 Airbnb ROI: 1.79% Traditional ROI: 0.51%
13 Maysens Way Windham, ME "AMAZING HOUSE, LOT, LOCATION & VALUE" This is the property you've been searching for with...	3 beds \| 2 baths \| 2,214 sq.ft.	$659,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 5.22% Airbnb Rental Income: $2581 Traditional Rental Income: $3920 Airbnb ROI: 2.03% Traditional ROI: 5.22%
9 Gunpowder Mill Road Windham, ME A striking expression of contemporary design, this exceptional residence commands attentio...	3 beds \| 3 baths \| 2,516 sq.ft.	$739,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 5% Airbnb Rental Income: $2581 Traditional Rental Income: $4235 Airbnb ROI: 1.7% Traditional ROI: 5%
21 Land Of Nod Rd Windham, ME Welcome to "The Tree House", where every window frames a view of nature. Set on nearly 10 ...	3 beds \| 3 baths \| 2,507 sq.ft.	$719,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 4.57% Airbnb Rental Income: $2581 Traditional Rental Income: $3829 Airbnb ROI: 1.78% Traditional ROI: 4.57%
7 Mancini Rd Windham, ME Nestled on a beautifully maintained 2.4-acre lot in Windham, Maine, this charming Cape-sty...	3 beds \| 2 baths \| 1,547 sq.ft.	$589,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.61% Airbnb Rental Income: $2581 Traditional Rental Income: $3183 Airbnb ROI: 2.39% Traditional ROI: 4.61%
14 Scout Ln Windham, ME Beautiful lot at end of private road. Big back and front yards. Open concept ranch with wo...	3 beds \| 2 baths \| 1,400 sq.ft.	$599,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 4.46% Airbnb Rental Income: $2581 Traditional Rental Income: $3151 Airbnb ROI: 2.33% Traditional ROI: 4.46%
25 Lake Avenue Windham, ME Timeless charm meets lakeside living at this beautifully restored 1920 bungalow just steps...	2 beds \| 3 baths \| 1,926 sq.ft.	$649,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 5.18% Airbnb Rental Income: $1554 Traditional Rental Income: $3838 Airbnb ROI: 0.67% Traditional ROI: 5.18%
14 Pope Rd Windham, ME Welcome to 14 Pope Road in Windham--a place that just feels like home the moment you pull ...	3 beds \| 1 baths \| 1,773 sq.ft.	$435,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 6.76% Airbnb Rental Income: $2581 Traditional Rental Income: $3258 Airbnb ROI: 3.58% Traditional ROI: 6.76%
305 Windham Center Road Windham, ME Charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 b...	4 beds \| 3 baths \| 3,217 sq.ft.	$625,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 6.28% Airbnb Rental Income: $4051 Traditional Rental Income: $4343 Airbnb ROI: 4.3% Traditional ROI: 6.28%
20 Cross Ridge Dr Windham, ME OPEN HOUSE Sunday 11-1!	3 beds \| 3 baths \| 2,875 sq.ft.	$699,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.95% Airbnb Rental Income: $2581 Traditional Rental Income: $4198 Airbnb ROI: 0.52% Traditional ROI: 3.95%
68 Outlet Cove Rd Windham, ME Set on a beautifully maintained peninsula in Outlet Cove, 68 Outlet Cove Road presents an ...	2 beds \| 3 baths \| 4,005 sq.ft.	$2,100,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.65% Airbnb Rental Income: $1554 Traditional Rental Income: $7243 Airbnb ROI: -0.5% Traditional ROI: 2.65%
77 Harvest Hill Rd Windham, ME 77 Harvest Hill Rd, Windham, ME 04062 \| Single Family Residential	3 beds \| 2 baths \| 2,052 sq.ft.	$599,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.71% Airbnb Rental Income: $2581 Traditional Rental Income: $2362 Airbnb ROI: 0.99% Traditional ROI: 1.71%
605 River Rd Windham, ME 605 River Rd, Windham, ME 04062 \| Single Family Residential	3 beds \| 2 baths \| 2,720 sq.ft.	$949,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.26% Airbnb Rental Income: $2581 Traditional Rental Income: $3286 Airbnb ROI: -0.24% Traditional ROI: 1.26%
78 Lakeside Dr Windham, ME 78 Lakeside Dr, Windham, ME 04062 \| Single Family Residential	3 beds \| 2 baths \| 1,600 sq.ft.	$650,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.87% Airbnb Rental Income: $2581 Traditional Rental Income: $3294 Airbnb ROI: 0.67% Traditional ROI: 2.87%
108 Highland Cliff Rd Windham, ME 108 Highland Cliff Rd, Windham, ME 04062 \| Single Family Residential	4 beds \| 2 baths \| 3,012 sq.ft.	$1,179,900	Airbnb cash on cash: 0.47% Traditional cash on cash: -0.02% Airbnb Rental Income: $4051 Traditional Rental Income: $2649 Airbnb ROI: 0.47% Traditional ROI: -0.02%
14 Family Cir #2 Windham, ME 14 Family Cir #2, Windham, ME 04062 \| Single Family Residential	2 beds \| 1 baths \| 1,135 sq.ft.	$509,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.47% Airbnb Rental Income: $1554 Traditional Rental Income: $2098 Airbnb ROI: -0.61% Traditional ROI: 1.47%
15 Sleepy Hollow Rd Windham, ME 15 Sleepy Hollow Rd, Windham, ME 04062 \| Single Family Residential	7 beds \| 4 baths \| 4,872 sq.ft.	$4,450,000	Airbnb cash on cash: -1.6% Traditional cash on cash: N/A Airbnb Rental Income: $4051 Traditional Rental Income: $0 Airbnb ROI: -1.6% Traditional ROI: N/A

Your search for investment property begins and ends here

Single Family Homes for Sale in Windham, ME

2 Twoey Dr

Windham, ME

4 beds | 2 baths | 1,655 sq.ft.

$554,900

Airbnb cash on cash: 4.33%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $4051

Traditional Rental Income: $3517

Airbnb ROI: 4.33%

Traditional ROI: 4.97%

214 Tandberg Trl

Windham, ME

4 beds | 2 baths | 2,052 sq.ft.

$539,999

Airbnb cash on cash: 3.78%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $4051

Traditional Rental Income: $3610

Airbnb ROI: 3.78%

Traditional ROI: 4.62%

99 Land Of Nod Road

Windham, ME

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

$767,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2581

Traditional Rental Income: $3879

Airbnb ROI: 0.64%

Traditional ROI: 3.33%

104 Harvest Hill Rd

Windham, ME

3 beds | 1 baths | 1,164 sq.ft.

$520,000

Airbnb cash on cash: 2.3%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $2581

Traditional Rental Income: $2910

Airbnb ROI: 2.3%

Traditional ROI: 4.25%

22 Montgomery Rd

Windham, ME

2 beds | 2 baths | 1,255 sq.ft.

$499,900

Airbnb cash on cash: 0.52%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $1554

Traditional Rental Income: $1926

Airbnb ROI: 0.52%

Traditional ROI: 2.27%

20 Freeman Ct

Windham, ME

4 beds | 2 baths | 4,602 sq.ft.

$1,485,000

Airbnb cash on cash: 0.51%

Traditional cash on cash: 1.64%

Airbnb Rental Income: $4051

Traditional Rental Income: $4743

Airbnb ROI: 0.51%

Traditional ROI: 1.64%

8 Environmental Way

Windham, ME

3 beds | 2 baths | 2,024 sq.ft.

$499,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $2581

Traditional Rental Income: $2362

Airbnb ROI: 2.16%

Traditional ROI: 3.02%

33 Spear Ave

Windham, ME

3 beds | 2 baths | 1,518 sq.ft.

$419,900

Airbnb cash on cash: 3.06%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $2581

Traditional Rental Income: $3318

Airbnb ROI: 3.06%