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$1,425,000
5 Beds ⋅ 3 Baths
Set on more than 100 feet of private sandy beach frontage on Little Sebago Lake, this completely renovated lake house offers a turn-key opportunity that rarely comes to market. The main home features five bedrooms and three full bathrooms, including a primary suite on the first floor. The stunning living room boasts cathedral ceilings with exposed beams, solar powered skylights, a floor-to-ceiling stone fireplace, and unobstructed views of the lake. Inside the kitchen you'll find all new stainless steel appliances including a gas range with a chef's hood, expansive cabinetry, and oversized windows. Outside, the 24x36 two car garage contains a work area and even more finished space above with a private deck overlooking the water. Entertaining here is effortless- the private dock and float provide boat, paddleboard, and swimming access just steps from the house, and sunsets can be enjoyed from the sprawling stone firepit. No detail was overlooked in this tasteful renovation; a new waterproof basement, drilled well, heat pumps, electrical, and roof are just some of the upgrades that make this home so special. This lakefront sanctuary is your opportunity to create memories in one of Maine's most exceptional settings.

112 Sabbady Point Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$475,000
3 Beds ⋅ 2 Baths
Welcome to this well-cared-for Cape in a park-like setting, with year-round water views of Highland Lake from the front deck. Enjoy your morning coffee watching the local bald eagles and listening for the loons, and in the evening gather around the fire pit in the flat back yard surrounded by hardwoods that show their colors in the fall. An extensive trail system starts right at the back property line so you can walk, snowshoe, or cross-country ski from your own yard. Inside you will find a spacious mudroom, a kitchen with granite counters, a breakfast nook, and updated appliances, and sun-filled dining and living rooms. A dedicated first-floor office is ready for remote work. Upstairs are three bedrooms and a second-floor laundry, with fresh paint and new carpet throughout. the big-ticket items have already been taken care of: new roof, new attic insulation installed by an Efficiency Maine certified vendor, a new high-efficiency propane boiler and a hybrid electric/heat pump water heater all keeping your heating and hot water costs down. Highland Lake is minutes away for kayaking, paddle boarding, ice skating and ice fishing, and the oversized shed is perfect to store all of those toys. This property offers privacy and plenty of open yard to garden, entertain, and play. Just 3.1 miles to shopping in Windham Center and an easy commute to Portland. Don't miss this one! Open Houses Saturday 9/12 10:00am-12:noon. Sunday 9/13 1:30-3:00pm.

96 Percy Hawkes Rd, Windham

Listing courtesy of RE/MAX Shoreline.

$415,000
3 Beds ⋅ 2 Baths
Indoor and outdoor living at it's best! Come see this great little cottage with water access on the shores of Pettingill Pond. This 3 bedroom 2 bath year round home has been thoughtfully updated and remodeled for ease of living. It features a thoughtfully designed new kitchen with modern features and artistic touches which leads to a giant deck perfect for entertaining. The 2 updated bathrooms and unique layout provides for separate and cozy spaces perfect for when guests arrive or house sharing. Every space feels fresh and ready for its new owner. Major improvements including a new roof and exterior stain have been completed recently so you can just bring your kayak and paddle and get on the water without the worry.

5 Shore Rd, Windham

Listing courtesy of RE/MAX Coastal.

$579,000
4 Beds ⋅ 3 Baths
Historic circa-1900 farmhouse on 4 acres of fields and forest in a desirable rural Windham location, adjacent to Bumbleroot Organic Farm and minutes to Westbrook and Gorham. Filled with vintage character and potential, the home features abundant custom cabinetry in the kitchen, dining, and office spaces; a separate bedroom suite with soaking tub and walk-in closet; and a sunroom overlooking a fenced garden, open field, and woods. A 1,200-square-foot post-and-beam barn provides outstanding possibilities for a workshop, studio, storage, animals, or hobby use. A rare chance to restore, reimagine, and make this remarkable property your own.

180 Highland Cliff Rd, Windham

Listing courtesy of A Team Realty.

$999,000
3 Beds ⋅ 2 Baths
Beautifully maintained and full of character, this inviting log sided home offers the quintessential Maine lakefront lifestyle on the shores of Little Sebago Lake. The home features three bedrooms and one and a half baths with a warm and welcoming open-concept kitchen/dining area that flows into a living room anchored by an impressive double-sided fireplace. Hardwood flooring throughout many of the rooms add to the home's timeless appeal. Upstairs, you'll find three generous bedrooms, including a primary with its own private screened-in porch—a peaceful place to enjoy your morning coffee while taking in the sights and sounds of the lake. A spacious family room with cathedral ceilings provides additional room to gather, relax, or accommodate guests. Just off the family room, a cozy nook offers the perfect spot for a home office, study, or quiet reading retreat. Beautiful wood detailing in the soaring upstairs ceilings enhances the warmth and craftsmanship of this special home. An attached one car garage provides excellent storage and offers potential for conversion into additional overflow living or recreational space. Outside, the large, level yard features established landscaping and plenty of room to enjoy the outdoors. At the water's edge, two docks provide easy access to Little Sebago Lake for boating, swimming, fishing, kayaking, or simply relaxing by the shore. With miles of water to explore, days here can be spent cruising the lake, enjoying time on the water, and returning home to your own private waterfront retreat. A dual purpose shed provides plenty of room for tools, gardening supplies, lake gear, and recreational toys, while a large woodshed and additional smaller shed provide even more storage. Offering the warmth and character of a classic Maine log style home, generous outdoor space, and direct access to one of the area's most desirable lakes, this property is equally suited for year-round living or a special Maine getaway of your own.

92 Sabbady Point Rd, Windham

Listing courtesy of Real Estate 2000 ME/NH.

$649,999
3 Beds ⋅ 2 Baths
Welcome to 51 Gambo Road in Windham, where peaceful waterfront living meets everyday convenience. Set along 144 feet of privately owned Presumpscot River frontage, this unique property offers a rare opportunity to enjoy nature right outside your door while remaining close to shopping, dining, walking trails, golf, beaches, fishing, kayaking, and canoeing. This 3 bedroom 2 bathroom home offers over 2400 total square feet and has seen numerous thoughtful renovations, including a newly renovated kitchen, bathroom, and basement. Enjoy your mornings on the screened-in front porch, then spend your afternoons by the river before unwinding in the hot tub or sauna. An outdoor patio and fire pit create the perfect setting for evenings with friends and family. Private riverfront, modern updates, endless recreation, and unmatched tranquility. Come experience 51 Gambo Road, and discover a home that feels like a getaway, without giving up the convenience of being close to most everything!

51 Gambo Rd, Windham

Listing courtesy of Landing Real Estate.

$786,000
3 Beds ⋅ 3 Baths
Stunning Private Estate Home with In-Law Suite - 2 Acres of Privacy. Welcome to this exceptional property offering the perfect blend of luxury living and versatile space. Nestled on a generous 2-acre lot, this home features a gourmet kitchen ideal for entertaining, three spacious bedrooms, and a private 1-bedroom in-law apartment/unit completely separate from the main house. Highlights: Master Suite - Expansive primary bedroom with full private bath and a spacious walk-in closet Gourmet Kitchen - Designed for the home chef and perfect for gatherings Separate 1-Bedroom In-Law Unit / Apartment - Ideal for guests, multigenerational living, or rental income Daylight Finished Basement - Bright, usable living space with natural light Two 2-Car Garages (one attached) - Both fully heated one with radiant floor heat and the other has a Modine heating system for year-round comfort Backyard Patio - Perfect for outdoor entertaining and relaxation 2 Acres - Private setting with room to enjoy nature and outdoor activities This rare offering combines comfort, functionality, and privacy in one outstanding package. The separate in-law unit, dual heated garages, and finished daylight basement provide flexibility few homes can match. Don't miss this unique opportunity! Contact us today to schedule your private showing.

6 Barbara Win Ln, Windham

Listing courtesy of EXP Realty.

$415,000
3 Beds ⋅ 1 Baths
Welcome home to this beautifully maintained 3-bedroom, 1-bath home with a two-car garage, ideally located with convenient access to Windham, Gorham, Portland and surrounding areas. Move-in ready and thoughtfully cared for, this home offers a wonderful combination of comfort, extensive improvements and pride of ownership. Major improvements completed in 2025 include new 1/2-inch foam board and 7/16-inch OSB, new vinyl siding, Matthews Brothers Sanford Series double-hung windows, new exterior doors with storm doors, blown-in insulation in the walls and attic, new seamless gutters on both the house and garage, and a new roof featuring ice and water shield. A new large capacity 200 amp electrical panel was also installed, along with a positive drainage system in the basement. Inside, you'll find a warm and inviting home with fresh paint throughout, a spacious living room, three comfortable bedrooms and a nicely appointed kitchen and bath. Step outside and enjoy the beautiful backyard, rear deck and newer 12' x 20' shed, providing plenty of additional storage for lawn equipment, recreational gear and more. One feature that really sets this home apart is the recessed RGB LED Wi-Fi soffit lighting. Customize the exterior lighting for holidays and special occasions, or simply create attractive accent lighting that showcases the home year-round. Additional improvements over the years include kitchen and bathroom renovations, living room flooring, chimney repointing, a replacement oil tank, garage roofing and vinyl siding, and the rear deck. With extensive recent improvements, added insulation, newer windows and doors, updated electrical, a two-car garage, great outdoor space and a convenient location, this is a home where much of the work has already been done. Move in, settle down and simply enjoy being home.

127 Main St, Windham

Listing courtesy of LAER.

$1,955,000
4 Beds ⋅ 4 Baths
A carefully curated and renovated mid-century modern home with full attention to details......this home has both waterfront privacy with a .56-acre yard and beautiful appointments! The builder purchased 3 lots and lined each side with now mature trees and hedges to create a rare oasis on Banjo Cove! These 3 lots, facing south, bring sunsets, sunrises and abundant wildlife viewings! The flat level entrance to a solid sandy bottom of 152 feet of waterfront is perfect for swimming, fishing and best of all, no steps, weeds or boulder rocks to content with!!! The original home was built in 1960, but an expansive addition of 800 square feet was added in 2023. In 2026, the owner worked with an experienced architect, removing walls to give a seamless flow to the first floor. The hardwood floors, exterior cedar shakes, floor to ceiling windows, open cable railings are stunning!! Two primary suites/bathrooms. A large deck makes outdoor dining and entertaining a pleasure! Three sets of double glass sliders bring in the gorgeous views, a bar sink and plumbing for an additional outdoor sink/prep area with both hot/cold water make cooking a breeze. A sunny downstairs daylight walk out basement with full lake views has a small kitchenette, an office/bedroom and a 640 square foot family room. The owner has used this space for weekly rentals for 11 years. A camp shower and bathroom and full laundry plus a modern gas fireplace and a separate entry are in place for you to enjoy or continue to rent. The kitchen and sitting area was added in 2023 upstairs with Viking/sub zero appliances. A modern vaulted ceiling with uplighting, a second gas fireplace, double pantries ......and a 9-foot quartz island complete it! Established perennials, irrigation lines, whole house generator, dock, and two hot water heaters. Little Sebago Lake is one of Maine's finest, stocked with trout annually! A haven to create a lifetime of lake memories!! Two hours to Boston, 30 minutes to Portland

233 Smith Rd, Windham

Listing courtesy of Judy George Realty.

$499,000
3 Beds ⋅ 2 Baths
Welcome to this wonderful 3-bedroom, 2-bathroom ranch-style home, offering comfortable living and thoughtful updates throughout. The large, renovated kitchen and open first-level floor plan create a fresh, inviting space for cooking, gathering, and everyday living. A newly built 2-car garage provides plenty of room for vehicles, storage, and more. Step outside onto the updated Trex deck, perfect for relaxing, entertaining, and enjoying the outdoors. The lower level offers flexible additional space that can easily serve as a work-from-home office, playroom, or extra storage. With its combination of modern improvements, versatile living spaces, and easy ranch-style living, this home is ready to welcome you!

3 Tucker Dr, Windham

Listing courtesy of Waypoint Brokers Collective. brandon@waypointbrokers.com
$495,000
1 Beds ⋅ 1 Baths
If you've been searching for a true, easy-living Maine camp feel with modern comfort, you've found it! 12 Getaway Road in Windham checks every box. Nestled right on the quiet Little Duck Pond, this charming, updated cottage offers peaceful waterfront living with the unbeatable convenience of an easy-access Windham location. Inside, the fresh space centers around the amazing views and a beautiful stone fireplace. This cottage has been beautifully updated with a new kitchen, bath, flooring and pine shiplap throughout. Enjoy this private, quaint cottage on a clean 35 +/- acre pond that is home to largemouth bass, perch, pickerel, etc. Kayak, paddle, swim or launch your motorized boat right from your front yard.

12 Getaway Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$275,000
Imagine building the home you've always wanted just steps from Highland Lake. Tucked into Windham's sought-after Highland Lake community, 58 Lower Beach Road offers a rare opportunity to create something entirely your own in a setting where lake life becomes part of everyday life. Located just one lot back from the water with points of access to Highland Lake, this is your chance to build near one of southern Maine's treasured lakes without settling for someone else's vision of what a lake home should be. Picture summer mornings heading to the lake, afternoons spent swimming, paddling and boating, and quiet Maine evenings returning home from the water. Here, the dream isn't simply owning a house, it's creating a lifestyle around the place you want to be. And the location makes it even better. Enjoy the natural beauty and recreation of Highland Lake while remaining close to everything Windham has to offer and within easy reach of Greater Portland. It's the kind of setting that lets you feel away from it all without actually being far away. Bring your own vision and builder or explore the property's separately offered build package for an opportunity to take much of the guesswork out of creating your new home. 58 Lower Beach Road isn't simply a piece of land. It's an opportunity to finally build the lake lifestyle you've been imagining. Shared water access to Highland Lake. The exact location, extent, and amount of shared water frontage are currently being confirmed by the attorney. **Also offered as a to-be-built home package -- see MLS #1676599 for additional details. **

58 Lower Beach Rd, Windham

Listing courtesy of Keller Williams Realty.

$975,000
3 Beds ⋅ 3 Baths
Welcome to 15 Alpine Drive, Windham--where modern living, incredible amenities, and exceptional garage space come together in one impressive property. Thoughtfully designed for everyday comfort and entertaining, this home is filled with the upgrades and little details you've been looking for.The kitchen features quartz countertops, glass tile backsplash, custom soft-close hickory cabinetry, Kohler cast-iron farmhouse sink, and hand-blown glass island lighting. Enjoy on-demand hot water, Daikin heat pump cooling, dimmable LED lighting, whole-house fire sprinklers, and extensive smart-home technology. Ethernet is wired throughout, along with integrated Sonos audio in multiple rooms, garage, deck, and pavilion.Outside is your own private retreat! The approximately 150'x100' fenced backyard features a 16'x37' heated inground pool with Roman end and LED lighting, 6-person Vita Spa hot tub, and 28' custom pavilion with power and lighting. Hunter WiFi-controlled multi-zone irrigation and rear gate access toward neighborhood ATV/snowmobile trails add even more convenience.Car enthusiasts, hobbyists, and anyone needing serious space will love the HEATED 32'x40' garage with 12' ceilings, three 10' doors, 9,000-lb Rotary automotive lift, sink, extensive overhead lighting, generator wiring, Ethernet, and multiple 120V/240V receptacles.Pool, pavilion, hot tub, smart-home features, privacy, trails, and an incredible heated garage--all the little things you've been looking for are already here. Why build when your dream home is right here? Windhams private community crossridge is waiting!

15 Alpine Dr, Windham

Listing courtesy of Elevate Maine Realty.

$525,000
3 Beds ⋅ 3 Baths
This brand new Cottonwood Colonial 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 functional mudroom and a great back deck. Upstairs includes a primary suite with walk-in closet, two additional bedrooms, a second full bathroom, and laundry hook-ups. 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!

2 Shepherd Ln Unit 1, Windham

Listing courtesy of RE/MAX By The Bay.

$599,000
4 Beds ⋅ 2 Baths
Opportunity meets versatility at 5 Cliff Drive in Windham. Set on a spacious 1.84-acre lot, in The C3 Zone, this property offers more than 2,000 square feet of living space, a flexible floor plan, and is set up with an ADU (check with the town for specifics) with a tenant already in place. The upper level offers generous living spaces and plenty of opportunity for a new owner to make it their own. While ready for some updating and personal touches, the property's layout, setting, and additional spaces provide an excellent foundation for creating something truly special. A standout feature is the walkout lower-level with a kitchenette and its own bathroom and entrance coupled with separation from the main living areas, this space offers tremendous flexibility for future possibilities; multigenerational living, extended-stay guests, or supplemental income. There's even more potential to explore. Above the attached garage is additional unfinished space that may offer an opportunity for future expansion--perhaps a home office, studio, bonus room, or additional finished space, subject to necessary approvals. For folks looking for a property they can improve and grow into over time, the possibilities here are particularly appealing. Outside, nearly two acres provide room to enjoy the Maine seasons, complemented by established outdoor spaces, stonework, a large deck and patio areas. The attached heated garage and additional outbuilding add valuable storage and functionality. Conveniently located near Windham's shopping, dining, recreation, and everyday amenities, 5 Cliff Drive presents an exciting opportunity for a buyer who sees the possibilities. With acreage, flexible living space, expansion potential, Commercial possibilities, and room to add value, this is a property ready for its new owner!

5 Cliff Dr, Windham

Listing courtesy of Rockstar Real Estate.

$499,900
3 Beds ⋅ 1 Baths
Offered for the first time in over 30 years, this charming 3 bedroom, 1 bathroom home with 1,331 square feet of living space sits on a private 0.41 acre lot tucked away on a quiet dead end road. Surrounded by mature greenery, fruit trees, and flowering shrubs, the setting provides a peaceful retreat with classic curb appeal highlighted by a red cedar shake exterior and a circular style paved driveway offering ample parking. Inside, the bright living area features original hardwood floors, abundant natural light, and a cozy brick fireplace that adds warmth and character. The home extends its living space outdoors with an expansive elevated rear deck spanning the width of the house, ideal for dining and entertaining, along with a covered lower level walkout patio perfect for relaxing in the shade. The finished lower level includes a spacious recreation room with wood paneling, ideal for a game room or home theater, and comes complete with a pool table. A dedicated workshop area offers built in benches, cabinetry, and pegboard storage, making it perfect for hobbies or projects. Enjoy deeded lake access just across the road via a shared right of way, offering easy opportunities for swimming, boating, and enjoying summer days by the water. This estate sale is being sold as is, presenting a wonderful opportunity to make this well loved home your own.

29 Lake Ave, Windham

Listing courtesy of Redfin Corporation.

$599,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION TO BE BUILT: Experience the best of lakeside living with this stunning new construction opportunity. This thoughtfully designed 3-bedroom, 2-bath home offers modern finishes, open-concept living, and the rare chance to personalize the home to fit your lifestyle. Nestled in a peaceful, scenic setting, the property includes two deeded access points to the lake, making it easy to enjoy swimming, kayaking, fishing, or simply taking in the tranquil waterfront surroundings. Surrounded by nature and nearby trails, this location offers the perfect balance of outdoor recreation and everyday comfort. The home can be customized, with additional options available such as a garage, daylight basement, expanded living space, and other upgrades to create your ideal home. Enjoy the serenity of lake life while remaining just 20 minutes from Portland, offering convenient access to shopping, dining, entertainment, and major commuting routes. Whether you're looking for a year-round residence or a peaceful retreat, this modern new construction home is a unique opportunity to build the lifestyle you've been dreaming of.

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$599,000
3 Beds ⋅ 3 Baths
This beautiful 3-bedroom, 2.5-bath home will have you celebrating your good luck! Life in this serenely situated Windham neighborhood strikes a perfect balance of comfort, convenience & idyllic charm. Inside, a seamless layout, hardwood floors, lofty ceilings, and mood-boosting natural light await. The kitchen's granite countertops, stainless steel appliances, gas stove, island with storage + seating, and large pantry will inspire every home chef. Open access to the dining area makes for easy chatting while cooking. Beautiful windows and a gas fireplace preside over the living room. A half bath with laundry rounds out the main floor. You'll love retreating to the primary suite upstairs, where peaceful nature views and a private bath create the perfect place to unwind. Two additional second-floor bedrooms and a full bath mean there's room for everyone. Opportunity abounds for entertainment, work, or play in the finished basement. Nature lovers & wildlife watchers will adore this tranquil, tree-lined spot, be it from the front porch, back deck, or around a campfire in the backyard. Evening strolls & bike rides are a breeze in the welcoming, walkable neighborhood. The attached 2-car garage adds everyday ease. North Windham's endless amenities mean you need not leave the bounds of town for a thing. Sebago Lake's public beach is a mere 5-minute drive away. This home will have you singing the praises of a life well-lived - a must-see! Showings begin Friday 7/31 OPEN HOUSE Sunday Aug 2nd 11-1

77 Harvest Hill Rd, Windham

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com
$450,000
2 Beds ⋅ 1 Baths
Don't miss this opportunity to own a year-round, two-bedroom cottage on beautiful Sebago Lake! Located in a five-member association, this property includes its own deep-water boat slip, making it ideal for boating enthusiasts. The renovation has already begun, as shown in the photos, giving the next owner a head start on creating their perfect lakeside retreat. The seller has decided to move on before completing the project, creating an excellent opportunity to add your own style and finishing touches. Enjoy the level common waterfront area featuring picnic tables, a fire pit, and plenty of space to relax and gather with family and friends. With a reduced list price, this cottage offers outstanding value and endless potential. Bring your vision and make this Sebago Lake getaway your own!

14 Family Cir Unit 2, Windham

Listing courtesy of Real Estate 2000 ME/NH.

$475,000
3 Beds ⋅ 1 Baths
Enjoy the best of both worlds with this charming 3-bedroom ranch featuring a 1-car garage, nestled in a peaceful rural setting in Windham while remaining just minutes from shopping, restaurants, and local businesses. The open-concept layout offers a spacious feel, highlighted by hardwood floors and a large front-to-back living room that's perfect for relaxing or entertaining. The primary bedroom provides a comfortable retreat, while city water and a spacious deck add to the home's convenience and appeal. Outside, you'll find two driveways, offering plenty of parking and flexibility. The property also presents future potential, with the town indicating it may be eligible for conversion to a duplex. Buyers are encouraged to perform their own due diligence to verify all zoning and conversion possibilities. Whether you're looking for a comfortable single-family home or an investment opportunity with expansion potential, this property is worth a look!

439 Falmouth Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$2,100,000
2 Beds ⋅ 6 Baths
Set on a beautifully maintained peninsula in Outlet Cove, 68 Outlet Cove Road presents an exceptional Little Sebago Lake setting with expansive waterfront, a private sandy beach, dock, and sweeping sunset views. The level lawn extends naturally to the shoreline, creating an inviting setting for swimming, boating, entertaining, or quiet mornings by the water. Every element reflects years of thoughtful care. Mature plantings, manicured gardens, stone retaining walls, and extensive hardscaping frame the home and lake views. A spacious paver patio and screened porch provide comfortable outdoor gathering spaces, while the sandy beach and dock make it easy to enjoy the lake throughout the day. Multiple outbuildings and garage spaces provide exceptional storage for boats, recreational equipment, tools, and seasonal belongings, while creating an ideal setting for entertaining. Inside, a sun-filled living room with a fireplace and wall of glass captures dramatic water views and flows into the dining area, kitchen, and lakeside deck. The primary suite includes a generous bath, laundry, and beautiful lake views. The walkout lower level features a second living room with a fireplace, an office, and a full bath, providing flexibility for guests or extended stays. Above the attached garage is an additional bedroom and loft area. A separate detached garage includes a heated room above, ideal for a studio, workshop, gym, home office, or additional storage. Recent improvements include a newer high-efficiency oil boiler, whole-home standby generator, drilled well, buried propane, and a septic system designed for four bedrooms. A pre-listing inspection and professionally measured floor plan are available for review. From the manicured grounds and carefully maintained outbuildings to the sandy shoreline and beautifully cared-for interior, this is a rare opportunity to enjoy Little Sebago Lake at its finest.

68 Outlet Cove Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$625,000
4 Beds ⋅ 3 Baths
*Back on the market - no fault of seller or property* This is your opportunity to enjoy and reap the rewards of this charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 bedroom, 1 bath In-Law apartment attached. Huge barn, w/work space/pottery studio, beautifully landscaped, pastoral 3.3 acre lot with gardens, flowers, blueberries, veggies and mature trees offered for the first time in 31 years. This classic home with modern accommodations has integrity and flexibility, it's just waiting for your design. Thoughtful and practical updates and upgrades made throughout the ownership. Lovingly maintained and enjoyed. Enchanting spaces inside and out. The farmhouse boasts a large, eat-in kitchen with a pantry and laundry room adjacent. Beautiful antique cast iron stove. Formal dining room and a 1st floor bedroom with a sizable dressing room/closet. Large, newer French doors lead to a sweet side deck overlooking green trees and fields. New roof on the main home 2024 as well as a heat pump for heating and cooling in 2023. The expansive mudroom separates the In-Law apartment from the farmhouse. In-Law apartment with its own deck was added in 1995. Perfect for personal, family use or for additional income. New roof on the apartment 2023, heat pump in apartment installed 2025. The barn and the back woodstock was used as the owner's pottery studio and wood fired kiln. A stunning piece of structural history, with tons of storage and space for your passions or practical uses. This truly special property offers a solid, warm and practical home on positively cinematic farm land. Tucked away from the hustle and bustle but only minutes away from walking trails and Windham Center for shopping, services, entertainment and dining. Less than 15 minutes to the Maine Turnpike, less than 30 minutes to Portland. Make this historic gem your own bucolic, rural paradise.

305 Windham Center Rd, Windham

Listing courtesy of Portside Real Estate Group.

$399,000
2 Beds ⋅ 2 Baths
Just in time to still soak up the most beautiful time here in Maine! Welcome to 47 Anglers, located on peaceful Pettingill pond. Water views, recent renovations, fresh paint throughout, original charm and outdoor recreation, all without the waterfront price tag! This 2 bedroom, 1.5 bath home is located on a private half-acre lot overlooking the pond. Just steps from your front door is your shared water access to put in your kayak, canoe or paddle board. When you aren't on the water you can still savor those views from your three season sun porch. Inside you'll enjoy your renovated kitchen, with stainless steel appliances, large living area, hardwood floors throughout creating warmth along with a cozy fireplace. First floor laundry is located in your half bath, and a full bath and two bedrooms are upstairs. A coveted mudroom, needed for every season here in Maine, whether you are kicking off your flip flops or winter boots. Outside, a one car garage and a large backyard perfect for games and entertaining. Conveniently located just minutes from North Windham shopping, dining and amenities, and centrally located just 30 minutes to Portland or Pleasant Mountain. Whether you are looking for yourself or for an investment property, this home, this location and this price point cannot be beat!

47 Anglers Rd, Windham

Listing courtesy of Portside Real Estate Group.

$4,200,000
7 Beds ⋅ 5 Baths
This is a rare opportunity to experience luxury lakefront living in this extraordinary, furnished waterfront residence on pristine Sebago Lake. Take in spectacular Mt. Washington views, breathtaking sunsets, abundant natural light and 113 feet of private shoreline.This area of Sebago's Jordan Bay is closest to the airport, the arts, world class restaurants and the ocean. Also just five minutes from local coffee shops, supermarkets, shopping and local restaurants. Multiple premier ski destinations are within an easy drive making this a true four season gem. Share what you will come to love about the Lakes Region with friends and family. Two attached guest suites/apartments seamlessly expand the home's living space for larger gatherings. Each has its own entrance and parking.The main level features a great room, an expansive kitchen, large island with seating for 6, a private office or formal dining room, and a luxurious primary suite complete with a walk-in closet and laundry. The spa-inspired ensuite bath includes a spacious steam shower with dual shower heads and jetted soaking tub. The fully finished walk-out lower level expands the home's possibilities with a dedicated media/theater room, an additional family room with kitchenette, bedroom and full bath--ideal for guests or extended family. Upstairs, you'll find another comfortable living area, two large bedrooms, a full bath, and an expansive deck where you can relax while enjoying panoramic views.Situated on 2.1 acres, the property features mature landscaping with fruit trees, an expansive lawn, playground, outdoor speakers, and a spacious patio with a fire pit--perfect for entertaining family and friends. Exceptional waterfront amenities include a permanent lakeside deck with seating, storage, and direct swimming access. The deep-water dock features a generous 12 x 20 ft seating area, Jet Ski lift, storage for lake toys, and a boat mooring with room for additional moorings.

15 Sleepy Hollow Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$499,900
2 Beds ⋅ 2 Baths
A year-round brook, your own private waterfalls, and a true Maine homestead on over 2 magical acres -- just 30 minutes to Portland. Some properties you tour. This one you fall for. Set on over two private acres along year-round Colley Wright Brook -- with over 300 feet of owned water frontage and your very own waterfalls -- this is the rare retreat where the land itself tells the story. Gather at one of two brookside fire pits, wander the gardens, or simply listen to the water from a porch tucked among mature trees. The 1969 log home is full of soul, built from logs harvested right up the road at Staples Farm. Inside, a cathedral-ceilinged living room is anchored by a grand wood-burning fireplace, while a heated three-season sunroom with radiant floors brings the woods-and-water views indoors all year. Enjoy easy one-floor living with two bedrooms and two full baths, plus a finished office/bonus room on the lower level for work, hobbies, or guests. For the self-sufficient at heart, this is a dream: an outdoor wood boiler can heat the entire home -- with soft or hard wood you harvest right from your own land -- backed by baseboard hot-water heat, a basement wood stove, and the sunroom's radiant floors. Heat your way, all year long. And the grounds are a love letter to the seasons: established perennial and raised-bed gardens, lilacs and dahlias, tulips and lilies, plus a true edible landscape -- apple trees, elderberries, serviceberries, rhubarb, blueberries, strawberry patches, and a full herb garden of chives, oregano, sage, and thyme. Private, peaceful, incredibly scenic -- yet only about 30 minutes to Portland. Additional acreage may be available; ask for details. Come stand by the brook and listen. You'll understand.

22 Montgomery Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$839,000
4 Baths
4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental history. Apartment features a small kitchen, washer and dryer, and private entrance separate. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. This Maine Cedar Log Home delivers exceptional space, comfort, and privacy. 1031 Exchange friendly. Broker offering free 1-year home warranty.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$839,000
4 Beds ⋅ 3 Baths
4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental history. Apartment features a small kitchen, washer and dryer, and private entrance separate. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. This Maine Cedar Log Home delivers exceptional space, comfort, and privacy. 1031 Exchange friendly. Broker offering FREE 1-year home warranty.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$180,000
Build your dream Maine home here! Discover 1.6 acres of open, peaceful land on Sky Drive in Windham. With a pond, generous space, and a private setting, this parcel offers the perfect canvas to create the home you've always envisioned. Enjoy the best of both worlds—peaceful country living with convenient access to downtown North Windham, the Maine Turnpike, and Portland, just approximately 35 minutes away. Outdoor enthusiasts will love being close to Sebago Lake and Little Sebago Lake, renowned for boating, fishing, and swimming. Property boundaries are clearly marked with visible pins. Opportunities to build in Windham don't come along every day—come see the possibilities and start planning your Maine getaway, year-round home, or future retreat!

68 Sky Dr, Windham

Listing courtesy of Locations Real Estate Group LLC.

$469,000
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

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