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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

$509,000

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!

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

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!

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

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.

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

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, pottery/artist 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.

4 Beds ⋅ 3 Baths

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, pottery/artist 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.

$649,000

Timeless charm meets lakeside living at this beautifully restored 1920 bungalow just steps from Big Sebago Lake. Rich in character and thoughtfully updated, this 2-bedroom, 2.5-bath home offers nearly 2,000 square feet of inviting living space with original details blended seamlessly with modern comfort. The warm and welcoming interior features a classic wood-burning fireplace, two comfortable living areas, a charming period-style kitchen, and two bedrooms with additional living space that's perfect for family and guests. Step outside to the spacious, west-facing deck where you'll enjoy breathtaking sunsets over Big Sebago Lake. Spend your days taking advantage of deeded access to the lake through the shared right of way directly across the road, offering an ideal setting for swimming, boating, and making lasting summer memories. Tucked away on a quiet dead-end private road, this well-landscaped property also features a new roof installed in 2025, adding peace of mind for years to come. Conveniently located near shopping, golf, and all the amenities of the Lakes Region, this exceptional home is equally suited as a year-round residence or a quintessential Maine getaway.

Timeless charm meets lakeside living at this beautifully restored 1920 bungalow just steps from Big Sebago Lake. Rich in character and thoughtfully updated, this 2-bedroom, 2.5-bath home offers nearly 2,000 square feet of inviting living space with original details blended seamlessly with modern comfort. The warm and welcoming interior features a classic wood-burning fireplace, two comfortable living areas, a charming period-style kitchen, and two bedrooms with additional living space that's perfect for family and guests. Step outside to the spacious, west-facing deck where you'll enjoy breathtaking sunsets over Big Sebago Lake. Spend your days taking advantage of deeded access to the lake through the shared right of way directly across the road, offering an ideal setting for swimming, boating, and making lasting summer memories. Tucked away on a quiet dead-end private road, this well-landscaped property also features a new roof installed in 2025, adding peace of mind for years to come. Conveniently located near shopping, golf, and all the amenities of the Lakes Region, this exceptional home is equally suited as a year-round residence or a quintessential Maine getaway.

25 Lake Ave, Windham

Listing courtesy of Keller Williams Realty.

$4,450,000

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.

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

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.

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.

$875,000

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 income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. 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. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

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 income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. 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. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$875,000

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 income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. 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. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

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 income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. 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. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$649,900

This is the largest single Townhouse unit in the complex and features lake views from every room, 33' width facing the lake and the full-length deck comes with an awning. Property comes with an existing mooring.

This is the largest single Townhouse unit in the complex and features lake views from every room, 33' width facing the lake and the full-length deck comes with an awning. Property comes with an existing mooring.

1112 Roosevelt Trl Unit 15, Windham

Listing courtesy of Allied Real Estate.

$499,000

Rare Sebago Lakefront Property! Don't miss this rare opportunity to own a beachfront home on the shores of stunning Sebago Lake with approximately 300 feet of private, sandy shoreline. This exceptional property offers breathtaking sunsets and panoramic views of Sebago Lake and Mount Washington. The home offers an updated kitchen with brand-new stainless steel appliances, modern cabinets and solid surface counter tops. Refreshed bathrooms feature modern vanities, fixtures, walk-in shower and tub/shower enclosure. Two large bedrooms with ensuite baths provide plenty of space, comfort and convenience. Additional interior improvements include new flooring, fresh paint, and updated lighting throughout, creating a comfortable blend of modern finishes and classic lakeside charm. Enjoy easy access to private community amenities including tennis, basketball, and pickleball courts, along with an expansive dock and a deeded mooring, ideal for boating, swimming, kayaking, and fishing. Year-round enjoyment continues through the winter months with ice fishing, snowshoeing, snowmobiling and peaceful lakefront living. Conveniently located near Windham Center, Point Sebago Golf Resort, area ski resorts, and just a short drive to Portland's Old Port and the Maine coastline. This property is well suited for year-round residence, seasonal getaways, or investment opportunity. Strong association finances have kept fees flat for the past three years and cover more than most associations, including exterior building maintenance, roofs, siding, water, septic, trash removal, plowing/shoveling, lawn care, dock, and tennis court, with no added assessments for over 10 years. Come experience all that this Sebago Lake community has to offer!

Rare Sebago Lakefront Property! Don't miss this rare opportunity to own a beachfront home on the shores of stunning Sebago Lake with approximately 300 feet of private, sandy shoreline. This exceptional property offers breathtaking sunsets and panoramic views of Sebago Lake and Mount Washington. The home offers an updated kitchen with brand-new stainless steel appliances, modern cabinets and solid surface counter tops. Refreshed bathrooms feature modern vanities, fixtures, walk-in shower and tub/shower enclosure. Two large bedrooms with ensuite baths provide plenty of space, comfort and convenience. Additional interior improvements include new flooring, fresh paint, and updated lighting throughout, creating a comfortable blend of modern finishes and classic lakeside charm. Enjoy easy access to private community amenities including tennis, basketball, and pickleball courts, along with an expansive dock and a deeded mooring, ideal for boating, swimming, kayaking, and fishing. Year-round enjoyment continues through the winter months with ice fishing, snowshoeing, snowmobiling and peaceful lakefront living. Conveniently located near Windham Center, Point Sebago Golf Resort, area ski resorts, and just a short drive to Portland's Old Port and the Maine coastline. This property is well suited for year-round residence, seasonal getaways, or investment opportunity. Strong association finances have kept fees flat for the past three years and cover more than most associations, including exterior building maintenance, roofs, siding, water, septic, trash removal, plowing/shoveling, lawn care, dock, and tennis court, with no added assessments for over 10 years. Come experience all that this Sebago Lake community has to offer!

1112 Roosevelt Trl Unit 8, Windham

Listing courtesy of Keller Williams Realty.

$180,000

The perfect spot to build your dream home in Windham! This 1.6-acre parcel offers a spacious, open lot with a peaceful pond. Sky Drive is a quiet, private road where you'll enjoy privacy and tranquility while still being just minutes from downtown North Windham and the Maine Turnpike. Enjoy the best of Maine living with nearby Sebago Lake and Little Sebago Lake, known for exceptional boating, fishing, and swimming. Plus, Portland is only a 35-minute drive away. Property boundaries are clearly marked with visible pins. An incredible opportunity to build in Windham!

68 Sky Dr, Windham

Listing courtesy of Locations Real Estate Group LLC.

$535,000

This brand new Maple 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 den or office, a functional mudroom entry, and a great back deck. Upstairs features three bedrooms, including a primary suite, plus laundry closet and 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!

This brand new Maple 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 den or office, a functional mudroom entry, and a great back deck. Upstairs features three bedrooms, including a primary suite, plus laundry closet and 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!

5 Shepherd Ln Unit 11, Windham

Listing courtesy of RE/MAX By The Bay.

$469,000

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!

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

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!

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

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!

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.

$525,000

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!

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!

10 Shepherd Ln Unit 5, Windham

Listing courtesy of RE/MAX By The Bay.

$1,485,000

Enjoy 700' of gated private Sebago Lake frontage with this exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, and exclusive access to the crystal-clear waters of Maine's premier Sebago Lake -- widely regarded as 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 and walk-in closet, 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

4 Beds ⋅ 3 Baths

Enjoy 700' of gated private Sebago Lake frontage with this exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, and exclusive access to the crystal-clear waters of Maine's premier Sebago Lake -- widely regarded as 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 and walk-in closet, 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.

$1,060,000

This large, cherished property has been lovingly preserved by the same family for decades, dating back to its early use by the Girl Scouts for camping and swimming. Encompassing just over 28 acres, the land offers exceptional privacy and includes a rare island in the river where children once camped. One of the property's most distinctive features is the river flowing from Sebago Lake, known for its sandy gravel bottom--ideal for wading, swimming, boating, and exploration. Fish often swim right up to visitors. Locals describe approximately seven miles of wild river corridor stretching in one direction to Dundee Dam and in the other beneath the historic covered bridge through North Gorham Pond to Gambo Falls, with additional access to the Pleasant River. The property is heavily wooded with towering century-old pine trees, filling the air with a pleasant pine scent in summer. There also appears to be potential for substantial gravel deposits. The existing 780± square foot cottage was built in the early 2000s by Woodcrafters of Maine and features a living room with wood stove, kitchen, bedroom, and bath on the first floor, plus a large second-floor space suitable for a bedroom, loft, or office. The home has a dug well and a two-bedroom septic system. Additional structures include a tool garage and a music studio. With approximately 844 feet of road frontage and about 743 feet of river frontage per town records, including the island, the property offers rare flexibility for a private estate, compound, campground, or potential subdivision, subject to approvals. Conveniently located just upstream from the historic covered bridge, with quick access to North Windham shopping, Portland, nearby towns, healthcare, and the interstate.

2 Beds ⋅ 1 Baths

This large, cherished property has been lovingly preserved by the same family for decades, dating back to its early use by the Girl Scouts for camping and swimming. Encompassing just over 28 acres, the land offers exceptional privacy and includes a rare island in the river where children once camped. One of the property's most distinctive features is the river flowing from Sebago Lake, known for its sandy gravel bottom--ideal for wading, swimming, boating, and exploration. Fish often swim right up to visitors. Locals describe approximately seven miles of wild river corridor stretching in one direction to Dundee Dam and in the other beneath the historic covered bridge through North Gorham Pond to Gambo Falls, with additional access to the Pleasant River. The property is heavily wooded with towering century-old pine trees, filling the air with a pleasant pine scent in summer. There also appears to be potential for substantial gravel deposits. The existing 780± square foot cottage was built in the early 2000s by Woodcrafters of Maine and features a living room with wood stove, kitchen, bedroom, and bath on the first floor, plus a large second-floor space suitable for a bedroom, loft, or office. The home has a dug well and a two-bedroom septic system. Additional structures include a tool garage and a music studio. With approximately 844 feet of road frontage and about 743 feet of river frontage per town records, including the island, the property offers rare flexibility for a private estate, compound, campground, or potential subdivision, subject to approvals. Conveniently located just upstream from the historic covered bridge, with quick access to North Windham shopping, Portland, nearby towns, healthcare, and the interstate.

594 River Road Rd, Windham

Listing courtesy of Plowman Realty Group.

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!

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.

$1,060,000

Rare opportunity to own a large surveyed waterfront parcel in Windham's Farm District offering a unique combination of rural character, natural resources, and recreation potential. The property features approximately 844 feet of road frontage and extensive river frontage including a private island, creating a rare setting for those seeking privacy, outdoor recreation, or rural land investment. A camp, well, septic system, and power already brought into the property allow immediate use while planning future possibilities. The land is covered with large mature pine trees, creating a beautiful forest setting with potential timber value while also preserving the natural character of the property. The parcel is located within Windham's Farm District, which is intended to protect farmland, woodlands, open space, wildlife habitat, and scenic areas while allowing compatible rural residential and agricultural uses. Permitted uses in this district include single-family and two-family homes, agriculture, forestry, farm enterprises, campgrounds (commercial or personal), riding stables, nurseries, sawmills, and mineral extraction, among other rural land uses. The property is believed to contain a substantial gravel deposit, which may offer additional resource value. Mineral extraction is a permitted use within the Farm District subject to local regulations and approvals. The river itself offers miles of recreation, running from Dundee Dam past the historic covered bridge through North Gorham Pond to Gambo Falls and out to the Pleasant River, making this location ideal for boating, kayaking, fishing, and wildlife viewing.With 844 feet of road frontage, river frontage with island ownership, existing utilities, mature forest, and flexible rural zoning, this property presents a rare opportunity for a private waterfront retreat, campground concept, agricultural use, or rural investment property.

594 River Road Rd, Windham

Listing courtesy of Plowman Realty Group.

$162,000

LAKESIDE LIVING: Bring your dream home to life on this exceptional, buildable lot offering privacy, natural beauty, and two separate deeded access points. Whether you're envisioning a year-round residence or the perfect lakefront getaway, this property is ready for your vision--with a custom building package available to simplify the process from start to finish. Much of the preparation has already been completed, including an existing well, a roughed-in driveway, and thoughtfully cleared building areas that maximize the property's potential while preserving its peaceful, wooded setting. Enjoy beautiful lake views and an ideal homesite ready for construction. Just steps from the end of your driveway, you'll have access to Forest Lake, a clean, private lake perfect for kayaking, boating, fishing, swimming, or simply relaxing by the water. Outdoor enthusiasts will also appreciate the nearby trail systems offering four-season recreation, including hiking, biking, snowmobiling, and more. Located just 20 minutes from Portland, this property offers the perfect balance of tranquility and convenience, with easy access to shopping, dining, and everyday amenities. This is a rare opportunity to own a ready-to-build lakeside property with the flexibility to create a home tailored to your lifestyle. Ask about the custom building package available and start planning your dream home today!

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$549,000

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.

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.

$849,900

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.

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.

$1,795,000

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. Enjoy 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 or all. Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was also 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. Little Sebago Lake 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 endless amenities

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. Enjoy 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 or all. Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was also 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. Little Sebago Lake 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 endless amenities

20 Ladyslipper Dr, Windham

Listing courtesy of Judy George Realty.

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!

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.

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!