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
26 Whites Bridge Rd #26 Windham, ME Nice Townhouse style condo with large remodeled bathroom. Home features ceramic tile, bran...	2 beds \| 1 baths \| 1,250 sq.ft.	$299,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 2.89% Airbnb Rental Income: $1554 Traditional Rental Income: $1926 Airbnb ROI: -0.03% Traditional ROI: 2.89%
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%
41 Lotts Dr Windham, ME Welcome to your dream investment property ''at the rotary'' in the picturesque town of Win...	5 beds \| 2 baths \| 2,252 sq.ft.	$594,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.29% Airbnb Rental Income: $2581 Traditional Rental Income: $2134 Airbnb ROI: 1.98% Traditional ROI: 2.29%
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%
1112 Roosevelt Trl #15 Windham, ME This is the largest single Townhouse unit in the complex and features lake views from ever...	2 beds \| 2 baths \| 1,584 sq.ft.	$649,900	Airbnb cash on cash: -1.45% Traditional cash on cash: 1.98% Airbnb Rental Income: $1554 Traditional Rental Income: $3186 Airbnb ROI: -1.45% Traditional ROI: 1.98%
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%
1042 Roosevelt Trl Windham, ME Welcome to 1042 Roosevelt Trail. This home is looking for it's next owner. Perfect home f...	N/A beds \| N/A baths \| 1,390 sq.ft.	$325,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.95% Airbnb Rental Income: $1028 Traditional Rental Income: $2527 Airbnb ROI: 0.86% Traditional ROI: 6.95%
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%
22 Daybreak Ln Windham, ME 22 Daybreak Ln, Windham, ME 04062 \| Condo/Coop	3 beds \| 3 baths \| 2,400 sq.ft.	$850,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 2.91% Airbnb Rental Income: $2581 Traditional Rental Income: $4259 Airbnb ROI: 0.01% Traditional ROI: 2.91%
0 Turning Leaf Dr Windham, ME 0 Turning Leaf Dr, Windham, ME 04062 \| Other	N/A beds \| N/A baths \| N/A	$1,995,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -1.67% Airbnb Rental Income: $1028 Traditional Rental Income: $1353 Airbnb ROI: -2.04% Traditional ROI: -1.67%
99 Enterprise Dr Windham, ME 99 Enterprise Dr, Windham, ME 04062 \| Other	N/A beds \| N/A baths \| N/A	$399,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 1.01% Airbnb Rental Income: $1028 Traditional Rental Income: $1353 Airbnb ROI: -0.81% Traditional ROI: 1.01%
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%
0 Tavern Hl Windham, ME 0 Tavern Hl, Windham, ME 04062 \| Other	N/A beds \| N/A baths \| N/A	$495,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.39% Airbnb Rental Income: $1028 Traditional Rental Income: $1432 Airbnb ROI: -1.26% Traditional ROI: 0.39%
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 Dolley Farm Rd #3 Windham, ME Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offe...	3 beds \| 2 baths \| 1,550 sq.ft.	$479,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.66% Airbnb Rental Income: $2581 Traditional Rental Income: $3595 Airbnb ROI: 1.02% Traditional ROI: 4.66%
26 Dolley Farm Rd #12 Windham, ME Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offe...	3 beds \| 2 baths \| 1,540 sq.ft.	$484,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.59% Airbnb Rental Income: $2581 Traditional Rental Income: $3595 Airbnb ROI: 0.98% Traditional ROI: 4.59%
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%
8 Shepherd Ln #4 Windham, ME This brand new home offers a blend of thoughtfully designed living spaces set in a peacefu...	3 beds \| 2 baths \| 1,352 sq.ft.	$469,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 6.35% Airbnb Rental Income: $2581 Traditional Rental Income: $3490 Airbnb ROI: 2.87% Traditional ROI: 6.35%
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%
243 Windham Center Rd Windham, ME Turn-key duplex in a convenient Windham location. Both units offer 2 bedrooms and 1 bathro...	4 beds \| 2 baths \| 1,728 sq.ft.	$575,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 2.87% Airbnb Rental Income: $4051 Traditional Rental Income: $2638 Airbnb ROI: 3.89% Traditional ROI: 2.87%
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%
12 Turkey Trail Windham, ME Excellent Opportunity: Very nice 2 bedroom, 1.5 bath Condominium with a full basement and ...	2 beds \| 2 baths \| 1,098 sq.ft.	$325,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 7.09% Airbnb Rental Income: $1554 Traditional Rental Income: $2570 Airbnb ROI: 2.3% Traditional ROI: 7.09%
10 Stillwater Drive Windham, ME The Highland offers a peaceful retreat designed for simple, modern living. With 766 square...	1 beds \| 1 baths \| 766 sq.ft.	$314,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.1% Airbnb Rental Income: $1362 Traditional Rental Income: $2297 Airbnb ROI: 0.53% Traditional ROI: 5.1%
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%

Real Estate investment in Windham, ME

There are 83 properties for sale in the city of Windham . The median list price in Windham is $499,701 and the average price per square foot is $234. In August 2026, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $2,648.

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

There are 83 investment properties available for sale in Windham.

In 2026, 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 $2,648.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, ME

26 Whites Bridge Rd #26

Windham, ME

2 beds | 1 baths | 1,250 sq.ft.

$299,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $1554

Traditional Rental Income: $1926

Airbnb ROI: -0.03%

Traditional ROI: 2.89%

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%