Windham Real Estate

Welcome to Windham, Maine – a picturesque town nestled in the heart of Cumberland County. Known for its breathtaking natural beauty and vibrant community spirit, Windham is a hidden gem that offers the perfect blend of rural charm and modern convenience. With its stunning lakes, lush forests, and scenic views, residents and visitors alike are drawn to the area's outdoor recreational opportunities, including hiking, fishing, and boating.

Windham boasts a rich history, with roots dating back to the 18th century. Today, it thrives as a welcoming community that values both tradition and progress. The town is home to a variety of local shops, delightful eateries, and community events that foster a strong sense of belonging. The annual Windham Summerfest is a highlight, bringing together families and friends for a celebration of local culture, food, and fun.

Education is a cornerstone of the Windham community, with highly-rated schools that prioritize student success and engagement. Families will appreciate the safe, friendly neighborhoods that make Windham an ideal place to raise children.

For those commuting to nearby Portland or seeking a tranquil retreat from city life, Windham offers easy access to major roadways while maintaining its serene atmosphere. Whether you’re looking for a cozy home or an expansive property, Windham’s real estate market has something for everyone.

Embrace the charm of Windham, Maine, where community, nature, and opportunity come together to create a truly enchanting place to call home. Discover your new beginning in this captivating town!

Newest Listings in Windham

$475,000

3 Beds ⋅ 1 Baths

Welcome home to this beautifully remodeled split level ranch home, nestled in a scenic convenient location. Offering the perfect blend of modern updates and peaceful surroundings, this home boasts three generously sized bedrooms and thoughtfully laid out living spaces throughout. The completely remodeled interior showcases stylish granite countertops, durable tile finishes and modern laminate flooring. The exterior is just as trouble free. Durable, low maintenance finishes all recently added to help you get settled. Enjoy the beauty of Maine right outside your windows, or from your private deck. Overlook fields and wooded surroundings while you're entertaining, enjoying morning coffee, or relaxing at the end of a long day. This property offers the comfort and ease of fully updated, move in ready atmosphere that will make you wonder why you didn't buy it sooner!

18 Cook Rd, Windham

Listing courtesy of Right At Home Realty.

$299,900

2 Beds ⋅ 2 Baths

Convenient location in a quiet, peaceful setting! Move in ready 2 bedroom, 1.5 bathroom townhouse-style condominium with a monitor heater fueled by natural gas that is affordable and cozy. Reasonable condo fees include outdoor pool, landscaping, snow management, and more. Full basement has plenty of storage, bonus usable space, and a possible future finished room. Location is close to shopping, lakes, and other outdoor fun.

22 Baxter Woods Trail, Unit 22, Windham

Listing courtesy of Harborview Properties, Inc..

$280,000

1 Beds ⋅ 1 Baths

Enjoy the simplicity this charming 1-bedroom, 1-bath home set on a private 5-acre lot in desirable Windham. This property offers a comfortable layout, a 1-car attached garage, and a screened-in porch perfect for relaxing while enjoying the peaceful surroundings. A handicap-accessible ramp provides easy access to the home. Whether you're downsizing, or searching for a weekend retreat, this property offers plenty of room to enjoy the outdoors with five acres of land to explore, garden, or simply appreciate the privacy and natural setting. Conveniently located just minutes from local amenities while offering the tranquility of rural Maine living. Don't miss this unique opportunity to own an affordable slice of Windham with acreage, and convenience.

148 Chute Rd, Windham

Listing courtesy of Maine Real Estate Experts.

$525,000

3 Beds ⋅ 2 Baths

Hand-hewn beams overhead, a sunny four-season room, and a sandy beach just across the street—there's much to love about 32 Mill Pond Drive. The house was moved to its present location in the early 1970s and placed on a poured concrete foundation. Built in 1875, this three-bedroom, two-bath home pairs historic character with thoughtful improvements. Wood floors, built-in cupboards and shelving, and exposed timbers bring warmth and personality to approximately 2,003 square feet of living space. The granite-countered kitchen connects easily to everyday living, while a gas parlor stove makes the living room an inviting place to settle in. Enjoy morning coffee in the four-season sunroom, open the doors to the deck for outdoor dining, or head across the street to Mill Pond's sandy beach, reached by a deeded right-of-way. Almost half an acre on a dead-end street provides room to garden, play and unwind, with a separate fenced area behind the garage. Significant investments include a whole-house weatherization project, replacement windows, a five-zone System 2000 boiler, vinyl siding and gutters installed in 2015, and a complete roof replacement with underlayment in 2020. First-floor laundry hookups and a two-car garage with electricity and upper-level storage add practical convenience. With its distinctive architecture, welcoming spaces and beach access, this is a home with a story—and room for your next chapter. Beach association dues are just $50 per year.

32 Mill Pond Dr, Windham

Listing courtesy of PO-GO REALTY.

$375,000

2 Beds ⋅ 1 Baths

Welcome to 87 Cotton Drive in Windham, Maine, where waterfront living on Collins Pond offers a peaceful setting to enjoy throughout the year. This charming 2-bedroom, 1-bath home features 646 square feet of living space, a heat pump for year-round comfort, and southwest-facing waterfront with a beach area. Spend your days swimming, paddleboarding, kayaking, or simply relaxing by the water. The southwest exposure provides afternoon sunshine and beautiful sunset views across the pond, creating an inviting setting to enjoy Maine's changing seasons. Whether you're looking for a year-round residence or a waterfront getaway, this property offers an opportunity to enjoy the simplicity of life on the water without sacrificing convenience. Located close to Gray and North Windham, with shopping, restaurants, and everyday amenities nearby. Portland and the Portland International Jetport are also within easy reach, making this an appealing location for both year-round living and weekend escapes. Enjoy the beauty of Collins Pond and the ease of waterfront living at 87 Cotton Drive.

87 Cotton Dr, Windham

Listing courtesy of Gibson Sotheby's International Realty.

$449,900

4 Beds ⋅ 2 Baths

Enjoy room to spread out, exceptional garage space, and shared access to Mill Pond at 6 Mill Pond Road in Windham. A welcoming mudroom offers the perfect place to shed snowy boots and winter gear during Maine winters, while the open first-floor layout creates an easy flow for everyday living and entertaining. The detached two-car garage offers enough depth to accommodate up to four vehicles parked tandem, providing ample space for cars, recreational equipment, or hobbies. A large back deck extends your living space outdoors, overlooking a spacious backyard with plenty of room for games, gatherings, and relaxing evenings. The finished basement adds flexibility with a large family room and additional finished space offering potential for a fourth bedroom, home office, or guest space. Whether you need room to entertain, work from home, or unwind, this lower level offers options to suit your needs. Enjoy access to Mill Pond through 200 feet of shared frontage, with opportunities for swimming and boating throughout the summer. Conveniently located near downtown Windham's shopping, dining, and everyday amenities, with the area's many lakes nearby, this property brings together indoor flexibility, outdoor enjoyment, and a convenient Lakes Region location.

6 Mill Pond Dr, Windham

Listing courtesy of Willis Real Estate.

$469,900

3 Beds ⋅ 1 Baths

Completely renovated inside and out, this move-in-ready home is ready for its next chapter! A new roof, siding, and windows deliver fresh curb appeal, while the interior welcomes you with a brand-new kitchen featuring granite countertops, a newly renovated bath, and new flooring throughout, including new carpeting in the bedrooms. Fresh paint and new light fixtures bring a polished, inviting feel to every room. Enjoy a sunny corner lot in an established, walkable neighborhood, with a storage shed for your outdoor essentials and a chicken coop that adds a touch of backyard charm. With extensive renovations already complete, you can skip the projects and get straight to enjoying your new home. Unpack, settle in, and make it yours!

90 Forbes Ln, Windham

Listing courtesy of Your Real Estate Company.

$419,000

2 Beds ⋅ 1 Baths

Welcome home to 126 Main Street in Windham! Step outside to a spacious backyard with a private deck, ideal for summer cookouts, morning coffee, or quiet evenings. Inside, the kitchen fills with sunshine every afternoon, making it a bright and cheerful place to cook and gather. Upstairs, many of the light fixtures have been updated for a fresh, modern feel. The family room in the basement offers extra space for movie nights, a playroom, or a home gym. A new furnace installed in 2018 adds peace of mind. With less than 30 minutes to Portland and the Sebago Lakes Region just down the road, you get the best of both worlds: room to breathe, easy access to city life, and many lakes to explore. Come see it today!

126 Main St, Windham

Listing courtesy of Homestead Realty.

$300,000

3 Beds ⋅ 1 Baths

Opportunities like this do not come around very often! Located on the Falmouth/Windham town line, with deeded access to Highland Lake and a private beach, this cozy three-bedroom, one-bathroom single-family home is the perfect opportunity to bring your vision to life. Situated on a 0.83-acre lot in a Farm Residential zoning district, your dream of having backyard chickens could now become a reality! Just 20 minutes from Portland and 10 minutes from North Windham, 3 Pine Dr. is surrounded by land preserves, walking trails, and endless water activities making it the perfect balance of city amenities and outdoor recreation.

3 Pine Dr, Windham

Listing courtesy of Elevate Maine Realty.

$710,000

4 Beds ⋅ 4 Baths

Welcome to 55 Evergreen Lane, a classic New England Colonial nestled in Windham's desirable Hillcrest neighborhood. Set on just over 1 acre corner lot amid towering pines, mature hardwoods, and beautifully established landscaping, this inviting property offers a wonderful combination of timeless architecture, comfortable living spaces, and a peaceful neighborhood setting. The traditional Colonial design features a welcoming central entrance, classic proportions, and an attached two-car garage. Inside, four bedrooms plus a dedicated office provide flexibility for today's lifestyles, whether working from home, accommodating guests, or simply enjoying room to spread out across 2,500 square feet. A fireplace and pellet stove add warmth and character, while a breakfast nook in the kitchen and mudroom built-ins off the garage door offer practical organization for everyday living. Outside, an expansive front lawn, mature trees, and a rear deck create opportunities to enjoy Maine's changing seasons. From the brilliant colors of autumn to long summer evenings surrounded by greenery, the property's established landscape provides an inviting backdrop for outdoor living.

55 Evergreen Ln, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$515,000

3 Beds ⋅ 2 Baths

Nestled on a private wooded 2 acre lot, this beautiful well maintained Colonial, offers the perfect blend of comfort, privacy and modern convenience. Home features 1,560 sqft of living space, 3 large bedrooms, 1.5 baths. The fully equipped kitchen with high end appliances, center island which provides excellent storage, workspace for cooking and a convenient area for casual dining. The spacious dining room provides plenty of room for gatherings and features a sliding glass door leading to the large L shaped back deck, perfect for enjoyment and outdoor entertaining. With the spacious sun-filled living room provides a bright and inviting atmosphere for relaxing after a long day. The 2nd floor laundry closet includes washer & dryer adds to the homes everyday convenience. The walk out basement and oversized storage shed provide abundant storage space for all your belongings.

89 Falmouth Rd, Windham

Listing courtesy of EXP Realty.

$399,000

3 Beds ⋅ 2 Baths

Welcome to 324 Pope Road in Windham! Located in a desirable neighborhood, this well-maintained home offers comfort, charm, and convenient access to local amenities. Freshly painted and featuring a recently updated kitchen with granite countertops and stainless steel appliances, this home is move-in ready. Hardwood floors add warmth and character, while a newer pellet stove provides an inviting touch during Maine's colder months. The home offers a finished basement with a spacious great room, full bath and walk-in closet, providing additional flexible living space. Outside, enjoy the yard, a shed with electricity, and seasonal views of Mount Washington. A wonderful opportunity to own a well-cared-for home in a sought-after Windham location! The 3rd bedroom in the basement is not considered a legal bedroom, the home has a 2 bedroom septic design.

324 Pope Rd, Windham

Listing courtesy of A Team Realty.

Start Your Search

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.

Windham Real Estate

Newest Listings in Windham

How much is your home worth?

How much is your home worth?