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Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

1 Bedroom with Beach Access

This beautifully converted 1860s carriage house loft blends historic charm with modern comfort. Tall vaulted ceilings showcase the exposed beams of the original timber framing, while a sliding barn door adds rustic character to the space. Nestled in a tranquil neighborhood, the apartment offers beach access to our neighborhood's pond—perfect for swimming or kayaking on sunny days. Conveniently located near North Windham businesses, 9 minutes from I-95 in Gray and 25 minutes from Portland.

cozy 3 bedroom ranch with deck and screen porch

Discover Maine in this spacious and serene space. Located within 5 miles to Gray turnpike or Windham shopping. On top of Adams hill one mile to Little Sebago lake. Recreational Trails on property for hiking, skiing, biking and 4 wheeling. It is advised to check ATV clubs and snowmobile clubs before deciding to come just for those activities, Ocean beaches, Old Port shopping dining and lake access near by. Great central location looking for space while visiting friends or family.

Maine Vacation Home on the Water

Create memories with family and friends at this well loved waterfront home with plenty of fun to be had whether you’re spending the day floating down the lazy ‘river’, swimming at the small association beach, kayaking on the pond or enjoying meals and games inside. Downtown Windham is minutes away (there is some traffic noise at the property) and has nice shopping and sweet restaurants while Portland is just 16 miles with everything Maine’s largest city has to offer.

Sebago Sunrise Yurt - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.

Sebago Lakehouse: Hot Tub and Private Beach Access

Lovely 3 bedroom/2 bathroom house in the woods with a Hot Tub and access to the private shared beach! Sebago Lake is a perfect family destination for swimming, boating, and fishing. It is ideally located for a day trip to Portland, Old Orchard Beach, Kennebunkport, or Freeport. Or stay home, enjoy the Lake or watch the stars from the Hot Tub. Close to grocery stores and restaurants. Lake and beach access is only a 5-minute walk.

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Cozy cottage near Sebago Lake

Cozy & adorable house (cottage) close to Sebago Lake. Backyard with fire pit. Great for those who like boating, swimming, fishing, skiing, snowmobiling. You are close to everything; Sebago Lake State Parks, several areas to launch a boat or visit one of the area beaches (house does not have lake access but plenty of access nearby). Less than 2 miles from grocery stores & restaurants/bars. Sorry no pets!l

Windham Lake Retreat | Knotty Pine Cabin Fire pit

Private knotty pine cabin with access to Pentingill Pond. 8 minutes to Sebago Lake w/fire pit and lawn games & 300Mbps WiFi workspace station. Newly remodeled. Walking distance to Bob’s Seafood & Lake House Tavern restaurants for lobster and live music. Sleeps 7, 2 king suites, 1 double bed, & couch. AC and smart TVs. Guest Favorite with 4.93 and 5.0 for check-in & communication. 20 min. to Portland.

Cozy Private Lake Getaway (Seasonal)

If you love the traditional camp, this place is for you! Located on Forest Lake bordering Gray, Cumberland and Windham, Maine, this cozy place is off the beaten path yet only 20-30 minutes from Portland and all it has to offer. Perfect for a couple looking for a quiet lake getaway. The one bedroom has a full size bed. The living room couch pulls out to a queen size bed for extra guests.

Christmas Tree Farm apartment

It's comfortable and cozy at this peaceful and centrally-located quiet one bedroom apartment on a Christmas Tree Farm. We are close to the city where you’ll find great breweries, restaurants, sporting events, and concerts. We are also near area skiing and snowshoeing in the winter along with golf courses, lakes and beaches in the summer.

Pond View Cottage

Pond View Cottage is a special place to rejuvenate in nature and foster deep connections. Overlooking the serene North Gorham Pond, the cottage is centrally located, only 5 minutes from Windham Shopping Center and 30 minutes from Portland, offering an ideal place to decompress or launch your next Southern Maine excursion.