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$445,000
3 Beds ⋅ 2 Baths
This brand new home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a full bathroom, a functional mudroom entry, and a great back deck. Upstairs includes three bedrooms, and 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!

8 Shepherd Ln Unit 4, Windham

Listing courtesy of RE/MAX By The Bay.

$699,000
2 Beds ⋅ 3 Baths
Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 25 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes provide both first and second floor primary suite options. Multi-generational, Companion, and Guest-Friendly, owners of these units can opt for stacked or side-by-side laundry on one or both floors of living. This inner unit features two full baths, a functionality first open concept kitchen, a front porch and back deck for sipping in the scenic surrounds, 18ft cathedral ceilings, and not one but two bonus spaces, fit for an office, spare bed, hobbying, or entertaining! This unit also has the option to finish its full-daylight walkout basement for an additional 500 SF of living area. Community Amenities to Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the over 50 acre parcel with over 6000 feet of nature trails, more than 500 feet of manicured lake front to carry in kayaks, canoes and paddleboards, plus a community maintained dock. Located just 10 miles from downtown Portland, residents will enjoy unbeatable proximity to top rated health care and hospitals, as well as Maine's finest dining and entertainment options. Boating, skiing, golf, shopping, dining, sports & activity clubs... The way 55+ life should be, and you can have it all in The Cove at Highland Lake! Reserve now & for a limited time you may customize your home's finishes!

25 Daybreak Ln Unit 8, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com
$479,900
3 Beds ⋅ 2 Baths
Welcome to 6 Shepherd Lane, 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. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$1,375,000
4 Beds ⋅ 3 Baths
Sebago Lake Lifestyle with 700' of gated private beach frontage and an exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, new roof, 5 bay garage & exclusive access to Maine's premier Sebago Lake - one of New England's top freshwater destinations for boating, recreation, and year-round beauty. Offering 4,602 square feet of finished living space, this estate features 4 bedrooms including a primary bedroom suite of over 1,000 sq ft gross living area, 2.5 baths, a 5-bay garage, set on over 2 acres providing privacy in every direction. The first-floor renovation creates an open-concept layout designed for effortless entertaining and everyday living. A stunning custom kitchen appointed with premium fixtures, Calacatta Brazil true white quartzite paired with contrasting black quartzite countertops, and waterfall-edge detailing that creates a sleek modern look. New flooring, recessed lighting, and an integrated sound system elevate the entire main living area. Additional recent improvements include a new 7,000+ sq ft roof, remodeled and updated baths, 15-zone irrigation system, new hot water heater, and a freshly resealed driveway. Multiple outdoor living spaces include a raised stone porch seating area, a large porch with a wooden trellis which is directly accessed from the first floor of the home, and a charming foot bridge overlooking a cascading stone fountain. A perfect way to let the world fade away as you relax in your own private backyard oasis after a day on the lake. Windemere Estates residents enjoy private Sebago Lake frontage with three beach areas, tennis courts, beach volleyball, gazebo, private boat launch, and a residents-only dock (boat slips available by tenure). Additionally, this estate is among a select few in the community to include its own mooring. Privacy, modern sophistication, and Maine lake living all come together at this must-see property. Shown by appointment only.

20 Freeman Ct, Windham

Listing courtesy of Holt Realty.

$479,900
3 Beds ⋅ 2 Baths
Welcome to 6 Shepherd Lane, 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. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$484,000
3 Beds ⋅ 3 Baths
Move in Ready! Come see why so many have chosen Dolley Farm Condominiums for their new home! The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas, while a rear patio extends your living space outdoors. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

26 Dolley Farm Rd Unit 12, Windham

Listing courtesy of The Flaherty Group.

$559,000
4 Baths
Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property with Huge Potential. 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.

$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.

$385,000
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.

$559,000
6 Beds ⋅ 4 Baths
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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