Eliaslelandrealtor.com Search Results

$625,000

*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.

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.

$419,900

Move right into this well-maintained home, perfectly situated on a semi-private lot surrounded by mature greenery. Enjoy deeded right-of-way access to Pettingill Pond for swimming, kayaking, or simply relaxing by the water, all while being just one mile from Windham's shopping, dining, and everyday conveniences. Inside, the daylight basement with a cozy pellet stove offers flexible living space, while the deck just off the kitchen is perfect for grilling, entertaining, or enjoying your morning coffee. A second full bathroom adds extra convenience, making this move-in-ready home an ideal blend of comfort, privacy, and location.

3 Beds ⋅ 2 Baths

Move right into this well-maintained home, perfectly situated on a semi-private lot surrounded by mature greenery. Enjoy deeded right-of-way access to Pettingill Pond for swimming, kayaking, or simply relaxing by the water, all while being just one mile from Windham's shopping, dining, and everyday conveniences. Inside, the daylight basement with a cozy pellet stove offers flexible living space, while the deck just off the kitchen is perfect for grilling, entertaining, or enjoying your morning coffee. A second full bathroom adds extra convenience, making this move-in-ready home an ideal blend of comfort, privacy, and location.

33 Spear Ave, Windham

Listing courtesy of Coastal Pine Real Estate, LLC.

$399,000

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!

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.

$699,000

We call it 'The Tree House'--a ranch built bigger and bolder. Set on nearly 10 private acres, this beautifully renovated home is wide, solid, and built to impress: hardwood floors, solid wood doors, statement glass hardware, a true primary suite, and a kitchen with a gas range made for real cooking. This multi-level layout offers a finished lower level, which adds a bonus room and kitchenette, guest suite, in-law space, studio, or office--the choice is yours. Out front, a pollinator garden brings monarch butterflies all summer long. A heated barn rounds things out with its own oil tank, a pro-grade Kellogg air compressor, pull-down loft storage, and a serious workspace. Minutes from Windham Center, area lakes, and an easy Portland commute--with potential for two additional buildable lots behind the home (subject to municipal approval). A transformation, inside and out.

3 Beds ⋅ 3 Baths

We call it 'The Tree House'--a ranch built bigger and bolder. Set on nearly 10 private acres, this beautifully renovated home is wide, solid, and built to impress: hardwood floors, solid wood doors, statement glass hardware, a true primary suite, and a kitchen with a gas range made for real cooking. This multi-level layout offers a finished lower level, which adds a bonus room and kitchenette, guest suite, in-law space, studio, or office--the choice is yours. Out front, a pollinator garden brings monarch butterflies all summer long. A heated barn rounds things out with its own oil tank, a pro-grade Kellogg air compressor, pull-down loft storage, and a serious workspace. Minutes from Windham Center, area lakes, and an easy Portland commute--with potential for two additional buildable lots behind the home (subject to municipal approval). A transformation, inside and out.

21 Land Of Nod Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$4,200,000

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.

$520,000

Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concept with 9' high ceilings. Recent updates include all new windows and doors, flooring on 1st level and 2nd floor hallway and a Vermont Casting woodstove for an additional source of heat. Enjoy the seasonal views of the Western Mountains and amazing sunsets from your front windows or sitting outside in your Adirondack chairs sipping your morning coffee. You will understand why its named, ''Harvest'' Hill Rd on this natural piece of property with the likes of strawberries, blackberries, blueberries, witch hazel and mint! Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is 5 minutes to both Little Sebago Lake and Big Sebago Lake boat launches and a quick walk or bike ride to the private beachfront of Tassel Top on Sebago Lake. The shops and grocery stores are 7 minutes away as well as minutes from Chipman's Farm Stand and Good Life Market! You are nestled away, yet 20 minutes from the Maine Turnpike, 30 minutes to downtown Portland (South) and 45 min - 1 hr (North) from Pleasant Mountain and Sunday River Ski Resort. Don't miss out on this little piece of heaven and check it out with a private tour today! Seller is willing to give concessions to Buyer at closing.

3 Beds ⋅ 2 Baths

Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concept with 9' high ceilings. Recent updates include all new windows and doors, flooring on 1st level and 2nd floor hallway and a Vermont Casting woodstove for an additional source of heat. Enjoy the seasonal views of the Western Mountains and amazing sunsets from your front windows or sitting outside in your Adirondack chairs sipping your morning coffee. You will understand why its named, ''Harvest'' Hill Rd on this natural piece of property with the likes of strawberries, blackberries, blueberries, witch hazel and mint! Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is 5 minutes to both Little Sebago Lake and Big Sebago Lake boat launches and a quick walk or bike ride to the private beachfront of Tassel Top on Sebago Lake. The shops and grocery stores are 7 minutes away as well as minutes from Chipman's Farm Stand and Good Life Market! You are nestled away, yet 20 minutes from the Maine Turnpike, 30 minutes to downtown Portland (South) and 45 min - 1 hr (North) from Pleasant Mountain and Sunday River Ski Resort. Don't miss out on this little piece of heaven and check it out with a private tour today! Seller is willing to give concessions to Buyer at closing.

104 Harvest Hill Rd, Windham

Listing courtesy of www.HomeZu.com. 877-249-5478

$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.

$839,000

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 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.

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.

$799,000

Enjoy the perfect balance of a quiet lifestyle near the water and local grocery stores, with an effortless commute. Located on a peaceful street just 15 mins to downtown Portland and minutes to Westbrook, this custom home is just 5 mins to Gambo trails & kayak launch. The open main level features a propane fireplace, chef's kitchen with quartz counters and gas range, and a dining area opening to a grilling deck. A custom brick-floored drop station adds high-end utility. A flexible 1st-floor room is perfect for a home office, while the massive finished bonus room above the garage features a sleek wet bar built for entertaining. Retreat to the luxury primary suite featuring a walk-in closet & spa bath with dual separate vanities. Complete with premium finishes, a full-house automatic generator, and a low-maintenance yard, this turn-key home is ideal for professionals. Stunning custom-built 4BR layout with a 3BR septic design.

4 Beds ⋅ 3 Baths

Enjoy the perfect balance of a quiet lifestyle near the water and local grocery stores, with an effortless commute. Located on a peaceful street just 15 mins to downtown Portland and minutes to Westbrook, this custom home is just 5 mins to Gambo trails & kayak launch. The open main level features a propane fireplace, chef's kitchen with quartz counters and gas range, and a dining area opening to a grilling deck. A custom brick-floored drop station adds high-end utility. A flexible 1st-floor room is perfect for a home office, while the massive finished bonus room above the garage features a sleek wet bar built for entertaining. Retreat to the luxury primary suite featuring a walk-in closet & spa bath with dual separate vanities. Complete with premium finishes, a full-house automatic generator, and a low-maintenance yard, this turn-key home is ideal for professionals. Stunning custom-built 4BR layout with a 3BR septic design.

24 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$790,000

Welcome to 25 Leonards Way! Set on a beautifully maintained 0.84-acre lot in one of Windham's sought-after established neighborhoods, this exceptional property offers the perfect blend of elevated finishes, everyday comfort, & an unbeatable location. Built in 2021, this beautifully kept 4-bedroom, 2.5-bath home offers nearly 2,400 square feet of thoughtfully designed living space with high-end finishes & quality craftsmanship throughout. Step inside to discover hardwood flooring, abundant storage, and inviting spaces designed for both entertaining and everyday living. At the heart of the home is an entertainer's dream kitchen featuring beautiful stone countertops, a stylish tile backsplash, ample prep space, & seamless flow into a generously sized dining area perfect for hosting dinner parties or casual evenings with family and friends. The warm & inviting living room is anchored by a gas fireplace, creating the perfect atmosphere year-round. Upstairs, the home continues to impress with a convenient second-floor laundry room and a beautifully updated primary suite featuring a brand-new custom glass & tile shower designed to create a spa-like retreat & walk-in closet. Recent updates include a brand-new heat pump system providing efficient comfort and air conditioning for summer months. Outside, enjoy a spacious back deck, a brand-new patio, & refreshed landscaping with garden beds, fresh mulch, mature trees, & a beautifully maintained yard creating a private outdoor retreat. The oversized finished two-car garage features a custom wood interior finish and exceptional storage capacity. A full daylight walkout basement is already framed, offering easy potential for future finished living space. Greatest luxury of all is the location, 15 min to Portland 7perfectly positioned between Maine's coastline, ski mountains, & Lakes Region. New school being built in Windham as well. Sophisticated & perfectly located this is truly a must see! 3 bed septic design in disclosure.

4 Beds ⋅ 3 Baths

Welcome to 25 Leonards Way! Set on a beautifully maintained 0.84-acre lot in one of Windham's sought-after established neighborhoods, this exceptional property offers the perfect blend of elevated finishes, everyday comfort, & an unbeatable location. Built in 2021, this beautifully kept 4-bedroom, 2.5-bath home offers nearly 2,400 square feet of thoughtfully designed living space with high-end finishes & quality craftsmanship throughout. Step inside to discover hardwood flooring, abundant storage, and inviting spaces designed for both entertaining and everyday living. At the heart of the home is an entertainer's dream kitchen featuring beautiful stone countertops, a stylish tile backsplash, ample prep space, & seamless flow into a generously sized dining area perfect for hosting dinner parties or casual evenings with family and friends. The warm & inviting living room is anchored by a gas fireplace, creating the perfect atmosphere year-round. Upstairs, the home continues to impress with a convenient second-floor laundry room and a beautifully updated primary suite featuring a brand-new custom glass & tile shower designed to create a spa-like retreat & walk-in closet. Recent updates include a brand-new heat pump system providing efficient comfort and air conditioning for summer months. Outside, enjoy a spacious back deck, a brand-new patio, & refreshed landscaping with garden beds, fresh mulch, mature trees, & a beautifully maintained yard creating a private outdoor retreat. The oversized finished two-car garage features a custom wood interior finish and exceptional storage capacity. A full daylight walkout basement is already framed, offering easy potential for future finished living space. Greatest luxury of all is the location, 15 min to Portland 7perfectly positioned between Maine's coastline, ski mountains, & Lakes Region. New school being built in Windham as well. Sophisticated & perfectly located this is truly a must see! 3 bed septic design in disclosure.

25 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$325,000

Brand New Price! First time home buyers, down sizers, Investors, builders, developers! Excellent opportunity on highly popular Roosevelt Trail with flexible Residential (RM) zoning, offering potential for limited business use, a home occupation, or multi-unit development. This neat, clean, and sun-drenched property sits on a spacious lot. An asset for immediate expansion or development is the existing two-bedroom septic system already on site. The property features a turnkey, updated 1-bedroom home with an efficient newe heating system and spacious downstairs laundry--this home is perfect for immediate rental income while you plan your expansion or development of the property. Capitalize on the large open backyard, paved driveway with a 1+ car garage, and two powered storage sheds. Explore the possibilities under the town's RM land use ordinance. Very convenient to Greater Portland, the Sebago Lakes Region, North Windham and Auburn. Perfect lower price point for buyers just starting out! Better than a tiny condo!

1 Beds ⋅ 1 Baths

Brand New Price! First time home buyers, down sizers, Investors, builders, developers! Excellent opportunity on highly popular Roosevelt Trail with flexible Residential (RM) zoning, offering potential for limited business use, a home occupation, or multi-unit development. This neat, clean, and sun-drenched property sits on a spacious lot. An asset for immediate expansion or development is the existing two-bedroom septic system already on site. The property features a turnkey, updated 1-bedroom home with an efficient newe heating system and spacious downstairs laundry--this home is perfect for immediate rental income while you plan your expansion or development of the property. Capitalize on the large open backyard, paved driveway with a 1+ car garage, and two powered storage sheds. Explore the possibilities under the town's RM land use ordinance. Very convenient to Greater Portland, the Sebago Lakes Region, North Windham and Auburn. Perfect lower price point for buyers just starting out! Better than a tiny condo!

549 Roosevelt Trl, Windham

Listing courtesy of Pine Tree Realty of Maine.

$1,175,000

~ OPEN HOUSE SUNDAY ~ 8/23/26! 10:30-12pm ~ Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be seen.

6 Beds ⋅ 5 Baths

~ OPEN HOUSE SUNDAY ~ 8/23/26! 10:30-12pm ~ Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be seen.

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$279,900

Spacious old home on the river with century old character and charm on a large private lot. Conveniently located in the Little Falls area of South Windham. Unique property has not been offered to the market for 50+ years. Great bones, good candidate for sweat equity or a flip.

4 Beds ⋅ 2 Baths

Spacious old home on the river with century old character and charm on a large private lot. Conveniently located in the Little Falls area of South Windham. Unique property has not been offered to the market for 50+ years. Great bones, good candidate for sweat equity or a flip.

42 Main St, Windham

Listing courtesy of Albert Neal Real Estate Company.

$1,485,000

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

4 Beds ⋅ 3 Baths

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

20 Freeman Ct, Windham

Listing courtesy of Holt Realty.

$494,900

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!

3 Beds ⋅ 2 Baths

Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$799,500

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

3 Beds ⋅ 3 Baths

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

32 Pennywhistle Dr, Windham

Listing courtesy of Keller Williams Realty.

$385,000

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

1 Beds ⋅ 1 Baths

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

12 Shore Rd, Windham

Listing courtesy of Rockstar Real Estate.

$1,595,000

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

3 Beds ⋅ 3 Baths

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

20 Ladyslipper Dr, Windham

Listing courtesy of Judy George Realty.

$559,000

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

6 Beds ⋅ 4 Baths

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

96 Mineral Spring Rd, Windham

Listing courtesy of Krainin Real Estate.