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$549,000
2 Beds ⋅ 2 Baths
Some properties sell a house. This one sells a lifestyle. Set on the shores of Sebago Lake with your own boat mooring, sandy beach access, and sweeping views of the water and mountains beyond, this condominium offers four seasons of the good life -- boating and swimming in summer, ice fishing and snowshoeing in winter, and quiet lakefront mornings year-round. Inside, hardwood floors and lake views set the tone in the living room, while the kitchen impresses with bright white beadboard cabinets, granite countertops, and full-sized appliances. Two comfortable bedrooms offer flexible living with a primary suite and a spacious second bedroom with plenty of room for bunks, perfect for guests or a full crew of weekend visitors. Community amenities include tennis, basketball, and pickleball courts and a shared dock, all managed by a rock-solid association that covers nearly everything and hasn't assessed in over ten years. Portland, Windham, and Point Sebago Golf Resort are all minutes away, but once you're here, you won't want to leave.

1112 Roosevelt Trl Unit 16, Windham

Listing courtesy of RE/MAX By The Bay.

$325,000
This .79 +/- acre lot has deeded rights to pass and repass on foot by the right of way from the County Road to Sebago Lake, and to pass and repass on foot along the shore of said Sebago Lake. The site offers an opportunity to build a spacious new home set back from the road along with an in-home business use and/or accessory apartment Alternatively, this site offers an opportunity to develop a 2,000 +/- Sq. Ft. medical arts building with town approval.

1042 Roosevelt Trl, Windham

Listing courtesy of Butts Commercial Brokers.

$235,000
Rare opportunity to build your dream home/getaway destination or private sanctuary away from it all, yet with conveniences of daily living still nearby. Nestled on a quiet street near the Pleasant River, with sloping hills, mature trees & majestic natural beauty as far as the eye can see, this buildeable Lot of just under 3 Acres, sits in the heart of Town and promises not only the wholesome peace & serenity of rural living, but views of the most breathtaking long sunsets, making it the ideal place to call 'home'. With soil tests, surveys, septic/ house plans & delineations now completed & driveways almost in - Summer in sweet Lakes Region awaits! Driveway for Lot to come off driveway of 37 Cook Rd./not accessible via the private property dirt road located after the stop sign/mailboxes at the end of the paved portion of Cook Road

39 Cook Rd, Windham

Listing courtesy of Keller Williams Realty.

$849,900
3 Beds ⋅ 4 Baths
Welcome to 23 Pennywhistle Drive, a beautifully designed contemporary farmhouse located in one of Windham's most desirable neighborhoods. Built in 2022 and thoughtfully crafted with both comfort and style in mind, this stunning home offers over 2,400 square feet of beautifully finished living space on a private 1+ acre lot. Inside, you'll find a bright and inviting open-concept layout filled with natural light, modern finishes, and quality craftsmanship throughout. The spacious kitchen flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. Luxury vinyl plank flooring, a cozy fireplace, and clean contemporary farmhouse design elements add warmth and character throughout the home. The home features three bedrooms, including a spacious primary suite complete with a private bath and custom built-ins in the closet. In addition to the bedrooms, there is a large bonus room above the garage offering flexible space for a media room, playroom, guest area, or home office. The walkout basement includes an additional bonus room and a convenient half bath, providing even more versatility and functionality. An expansive oversized three-door, four-car garage provides exceptional storage and workspace, perfect for vehicles, outdoor equipment, recreational gear, or hobby space. Designed for efficiency and convenience, the property also features solar panels and a full sprinkler system. Enjoy the peaceful setting while being just minutes from Westbrook, North Windham amenities, shopping, dining, lakes, outdoor recreation, and an easy commute to Portland. This nearly new home offers the perfect blend of modern farmhouse charm, efficiency, and convenience in the heart of Southern Maine.

23 Pennywhistle Dr, Windham

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$399,900
The parcel has water stubbed at the road and a gravel curb cut already installed. Ideal location for manufacturing, private warehousing and high bay boat storage.

99 Enterprise Dr, Windham

Listing courtesy of Butts Commercial Brokers.

$785,000
4 Beds ⋅ 3 Baths
Welcome to your opportunity to build a stunning modern farmhouse in the heart of Windham. This thoughtfully designed new construction package blends timeless charm with clean, modern finishes, offering both style and functionality across 2,600 square feet of beautifully crafted living space. This farmhouse style home features 4 spacious bedrooms, 2.5 bathrooms, and a2 car garage, designed with today's lifestyle in mind. From the moment you step inside, you'll appreciate the open-concept layout, highlighted by quality craftsmanship and carefully selected finishes throughout. The complete build package includes everything needed to bring your home to life, from foundation to final finishes. Enjoy peace of mind with a full construction scope including framing, roofing, siding, windows, doors, electrical, plumbing, and a high-efficiency wall-hung combi boiler heating system. Inside, you'll find durable and stylish LVP flooring, beautifully tiled bathrooms, granite countertops, hardwood cabinetry, and a full appliance package including stove, hood, refrigerator, dishwasher, washer, and dryer. Attention to detail continues with 6' baseboards and clean-lined trim, recessed lighting in the kitchen, pendant lighting over the island and dining area, and standard fixtures throughout. Outdoor features include a garage, decks, excavation around the home, tree cutting, well and septic installation, and a finished yard with loam and seed--creating a solid foundation for your future outdoor vision.

014-17-J01 Mimi Ln, Windham

Listing courtesy of The Maine Real Estate Experience.

$829,500
3 Beds ⋅ 3 Baths
This stunning home is bathed in natural light and beautifully appointed. It was purchased 1 year ago as an unfinished new build 3 bed/1 bath home, that is now transformed into a light, bright 3 bedroom 3 bath (plumbed for a 4th bath in the unfinished high ceilinged daylight basement) with a new sunny primary suite, library, laundry and mudroom. Enter the front door to a 2 story foyer and living room which flows into a large open kitchen with cabinets galore. A dining room, powder room with laundry, and mudroom leading to the heated garage complete the main floor. Up the bright open stairway to a spacious loft for study or exercise which leads to a 3 room primary suite with sun filled full bath tucked away from the bedrooms 2&3 that share another full bath. An expansive, fully fenced, 0.7 acre yard surrounded by 34 acres of preserve on 2 sides and fronting onto a cul de sac of just 20 homes. Conveniently located 8 miles from Portland, 5 miles from Gorham center in the charming So Windham village along the Presumpscot River with all of it's recreational opportunities. This home offers much of the best of Southern Maine, with heat pump for year round comfort and a high efficiency FHW natural gas system. Come discover your new home.

32 Pennywhistle Dr, Windham

Listing courtesy of Keller Williams Realty.

$1,995,000
•Approved State and Town for a 9,018± SF commercial building, including DEP, DOT, and Portland Water District •DEP & DOT permits approved in 2023 for the 2 building concept •Commercial District 1 Zoning suitable for a variety of uses •Rare parcel of land in one of Maine's fastest growing communities •Easy access to I-95 and other major corridors •Growing community with strong demand for commercial services, making this site well-positioned for both local businesses and regional operators •Situated in a growing commercial area of Windham, just minutes from Windham's busy Route 302 corridor with retail, dining, and service amenities •Great accessibility from nearby major routes, including Windham's busy Route 302 corridor, which serves as the commercial hub for the Lakes Region

Turning Leaf Dr, Windham

Listing courtesy of Malone Commercial Brokers, Inc..

$525,000
Welcome To Lot 4 Highland Cliff Road. This Beautiful 49.7 +/- Acre Parcel Has A Lot Of Options. Located in Windham off of the very popular Highland Cliff Road, Property is partially through the subdivision process as Phase 2 of the Canada Hill Subdivision, but very developable as a new subdivision (Talk to the planning board), or even just a very private spacious single lot. There is also an option to buy the 1.03 Acre Lot abutting this parcel in the Canada Hill Subdivision. Please call Broker for more info. This Property is a must see!!

Lot 4 Highland Cliff, Windham

Listing courtesy of Getty Real Estate Services, LLC.

$399,900
1 Beds ⋅ 1 Baths
Nestled along the peaceful shores of Pettingill Pond, 12 Shore Road in Windham, Maine has the perfect blend of classic lakeside charm and modern comfort. This inviting property boasts stunning water views, direct access to the pond, and a serene setting ideal for both year-round living and seasonal escapes. Inside, you'll find a bright and welcoming layout with large windows that fill the home with natural light and showcase the surrounding beauty. The open-concept living and dining areas create an easy flow for entertaining, while the kitchen provides ample space for preparing meals after a day on the water. Need more space, you will be pleased to find that this property also has a bunkhouse, perfect for overnight guests. Step outside to enjoy your private slice of Maine's natural beauty--whether it's morning coffee overlooking the water, afternoons spent boating or swimming, or evenings around the firepit under the stars. The property offers convenient pond access, making it easy to embrace the full waterfront lifestyle. Located just a short drive from local shops, restaurants, and all of Windhams amenities. This home combines tranquility with accessibility. Whether you're looking for a permanent residence, a vacation getaway, or an investment opportunity, 12 Shore Road is a rare chance to own a piece of Maine's sought-after waterfront living.

12 Shore Rd, Windham

Listing courtesy of Rockstar Real Estate.

$1,595,000
3 Beds ⋅ 3 Baths
New construction on Little Sebago Lake is a once-in-a-decade event. And this is that event. A sun drenched contemporary three-story residence modeled after a Maine Home + Design award winning home and sited on a private dead-end road shared by just six year-round properties. This home faces DUE WEST, so that every room on the waterside catches the full arc of sunset through the floor-to-ceiling glass. The colors were selected to blend in the surrounding woods and is custom shingled in cedar. Rare public water from the Portland Water District from May-October plus a drilled well for winter months. The 38-foot-deep garage serves for convenient storage and is 10 feet tall. There is opportunity to finish part ! Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was added. Inside, new hardwood floors run throughout. The kitchen anchors the open-concept main level with a ten-foot quartz island with double waterfall features. Subzero fridge and Viking induction range plus a double pantry. Central HVAC and a propane fireplace keep the home comfortable year-round. Two decks extend the living space toward the water -- one for morning, one for the long western light. The primary suite has a private door leading to the 3rd floor deck, where you may relax and soak in the views and sounds of the lake. At the water's edge, an original boathouse and a second storage screened structure remain from the property's earlier life, and both can make wonderful bunk or playhouses, fishing shacks or storage for all the recreational needs. For a individual who values waterfront access and flexibility, these buildings represent options that would NOT be permitted today. Water is 8 ft. deep at the dock! Little Sebago is one of southern Maine's finest lakes with over 6 miles of water to explore and enjoy. 30 minutes to the Portland Jetport/Amtrak station, 2 hours to Logan Airport. less than 1 hour to local ski mountains create end

20 Ladyslipper Dr, Windham

Listing courtesy of Judy George Realty.

$494,900
3 Beds ⋅ 2 Baths
Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

9 Shepherd Ln Unit 13, Windham

Listing courtesy of RE/MAX By The Bay.

$750,000
This is a quality constructed commercial building that is ideal for anyone on the trades. The front section is configured as offices. The rear section has high bay space with 2 overhead doors along with 2 other rooms; secure storage room and workshop room. Great exposure on Rt. 302 and high traffic count.

989 Roosevelt Trl, Windham

Listing courtesy of Butts Commercial Brokers.

$494,900
3 Beds ⋅ 2 Baths
Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

9 Shepherd Ln Unit 13, Windham

Listing courtesy of RE/MAX By The Bay.

$559,000
6 Beds ⋅ 4 Baths
BACK ON THE MARKET! Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property with Huge Potential or make it your home with an inlaw. Opportunity awaits. This unique property offers incredible potential for investors, contractors, or buyers looking to create value. Located just a short walk to association access on beautiful Sebago Lake, the property features multiple units and flexible living space with the possibility for rental income or multi-generational use. While the property does REQUIRE updates and improvements, the location and potential make it a rare opportunity in the Windham/Sebago Lake area. Enjoy the benefits of lake access while being conveniently located near local amenities, restaurants, and year-round recreation. Whether you're looking for an investment project, seasonal retreat, or property with income potential, this is a chance to bring your vision to life in one of Southern Maine's most desirable lake regions.

96 Mineral Spring Rd, Windham

Listing courtesy of Krainin Real Estate.

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