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$409,000
2 Beds ⋅ 1 Baths
✨ Valuable Updates + Equity Potential = Smart Buy in Windham! MORE UPDATES! Not a new home -- but packed with brand-new updates where it counts! This move-in ready Cape features a new furnace, new kitchen, new bath, and beautifully refinished hardwood floors, giving you modern comfort without the renovation hassle. Want room to grow your value? The unfinished second floor offers built-in equity potential -- add bedrooms, another bath, or create the primary suite of your dreams. Plus, a large dry basement provides even more opportunity to finish additional living space, a gym, office, or media room. 💡 ✔️ Sunny yard ✔️ Detached 2-car garage ✔️ Close to shops, dining & lakes ✔️ Only 20 minutes to Portland Move in now. Add value later. Smart buying starts at 10 Abby Road in Windham!

10 Abby Rd, Windham

Listing courtesy of Dream Home Realty LLC.

Selling Office: Landing Real Estate.

$405,000
3 Beds ⋅ 1 Baths
Access to Highland Lake sets the stage for the lifestyle you've been looking for at 27 Beach Road in Windham. Tucked away on a dead-end street, (with the sweetest path over a creek to the Lake) this move-in-ready home offers the perfect opportunity to enjoy lake life without the upkeep of direct waterfront ownership. Spend summer days swimming, paddling, fishing, or simply relaxing by the water, then come home to a wonderful backyard with plenty of room to gather, garden, play, or unwind. The setting offers a welcome sense of retreat while keeping you close to Windham's restaurants, shopping, recreation (Lowell Preserve is just at the end of the road near fire station), and everyday conveniences. Comfortable and ready to enjoy from day one, the property offers wonderful versatility as a year-round residence, Maine getaway, or potential rental investment. Whether you're looking for a place to call home or an opportunity to enjoy everything the Lakes Region has to offer, 27 Beach Road delivers an appealing combination of location, lifestyle, and flexibility. Move in, head to the lake, and make the most of Maine living. Deadline of Sunday 8/16 at noon with a response by 8pm the same day.

27 Beach Rd, Windham

Listing courtesy of Rockstar Real Estate.

Selling Office: Breakwater Realty Group, LLC.

$405,000
4 Beds ⋅ 1 Baths
Offered for the first time ever, this lovingly maintained one-family owned home is a rare opportunity in the heart of South Windham. Situated on a beautifully landscaped lot featuring mature lilac trees, established perennial gardens, and plenty of outdoor space to enjoy, this property combines timeless charm with an unbeatable location. Inside, you'll find spacious bedrooms, inviting living areas, and a cozy den centered around a fireplace--perfect for relaxing on a quiet Maine evening. The home's thoughtful layout offers comfortable everyday living while providing the opportunity to update and personalize to suit your style. Outdoor enthusiasts will appreciate being directly across the street from the Mountain Division Trail and Sebago to Sea Trail, offering miles of year-round recreation. The property is also just steps from the scenic Presumpscot River, a treasured local resource known for its natural beauty and recreational opportunities. Located in the growing South Windham Village area, this home enjoys convenient access to local favorites including the nearby Red City Ale House, shopping, schools, and everyday amenities. Combining a sought-after location, beautiful landscaping, one-family ownership, and endless potential, this is a special opportunity to own a home that has been cherished for generations and is ready for its next chapter.

41 Main St, Windham

Listing courtesy of FIV Realty Co Maine, LLC.

Selling Office: Smith & Company Realty.

$405,000
2 Beds ⋅ 2 Baths
This North Windham Ranch Condo is beautifully maintained, and move-in-ready. It offers a blend of natural tranquility and modern convenience. From the open fields to the wooded backyard, nature is all around you. The covered wrap deck is a welcome place to sit and relax or sip your morning coffee while listening to the birds chirping. As you enter the inside of the home, the open-concept and elegance, featuring cathedral ceilings and abundant natural light welcome you in. The hardwood and easy care vinyl flooring help make this home a breeze to maintain. The kitchen offers plenty of storage space along with spacious epoxy countertops and tile backsplash making this an ideal place for meal creation or buffet style entertaining, There are two well-sized bedrooms, including a Primary Suite with a private full en-suite bathroom. The 2nd full bath and first floor laundry room add to the convenience and easy living the home offers. The oversized 1 car garage is easily used for additional storage and a mudroom area to drop your boots and coats before entering the home. The full basement with high ceilings adds plenty of space to add a room or two or be used as storage overflow. Come see this amazing home today!

68 Provost Dr Unit 13, Windham

Listing courtesy of The Collective Real Estate Co.

Selling Office: RE/MAX Shoreline.

$400,000
2 Beds ⋅ 2 Baths
Beautifully updated and well-maintained home in a desirable Windham location! This move-in-ready property offers a thoughtfully improved interior with modern updates throughout, reflecting pride of ownership at every turn. The home features a bright, welcoming layout with comfortable living spaces ideal for both everyday living and entertaining. Recent updates enhance both style and functionality, while ongoing maintenance provides peace of mind for the next owner. Enjoy the meticulously landscaped grounds that create a welcoming outdoor setting and enhance the home's curb appeal. The lower level offers excellent potential and is ready for your personal touch, providing an opportunity to expand the home's finished living space with updated areas for a recreation room, home office, gym, guest space, or additional living area. Set in a quiet neighborhood yet conveniently located near shopping, schools, lakes, and commuter routes, this home offers the perfect blend of comfort, convenience, and value. A wonderful opportunity to own a turnkey Windham home with room to grow--don't miss it! Offer Deadline by 5 p.m. today, August 5th!

60 Forbes Ln, Windham

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

Selling Office: The Maine Real Estate Group.

$400,000
4 Beds ⋅ 1 Baths
Welcome to 442 River Road in Windham -- a spacious and inviting 4-bedroom home offering flexible living space in a desirable location. With two bedrooms on the first floor and two additional bedrooms upstairs, the layout provides comfort and versatility for a variety of living needs. The second floor was once used as an in-law style space, offering additional flexibility for guests, extended family, or private living quarters. The home also includes extra space that can be used for storage or adapted to fit your lifestyle -- whether as a home office, gym, playroom, or hobby area. Set on a generous lot with a two-car garage, the property offers plenty of room to enjoy both inside and out. Located in the sought-after town of Windham, you'll enjoy convenient access to local shops, restaurants, schools, and an easy commute to Portland. The area is also known for its proximity to the Sebago Lake region, offering boating, trails, and year-round outdoor recreation. This home combines space, flexibility, and a great location to enjoy all that Windham has to offer.

442 River Rd, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: Keller Williams Realty.

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

47 Anglers Rd, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Portside Real Estate Group.

$395,000
2 Beds ⋅ 1 Baths
Don't miss your chance to be on the water this season! This charming Maine bungalow on Collins Pond offers the kind of lifestyle people dream about all winter. Enjoying morning coffee while overlooking the water, afternoons spent swimming, paddling, boating or fishing, and peaceful evenings relaxing along the shore. Collins Pond is a private, approximately 43-acre pond with no public access, creating a quieter and more intimate setting for waterfront living. Known for warm-water fishing, including smallmouth bass, largemouth bass and chain pickerel, it is an inviting place to cast a line, launch a kayak or simply enjoy the view from your own piece of Maine. Set on a manageable lot with classic cottage character, the home is ready for immediate enjoyment while still offering opportunities to personalize and enhance it over time. Whether you envision a seasonal getaway, a comfortable year-round home or a waterfront property with exciting potential, this is a place where lasting memories can begin the moment you arrive. Windham offers the perfect balance of lakeside living and everyday convenience, with North Windham's shopping, restaurants and services just minutes away and Portland within an easy drive. Enjoy all the recreation of Maine's Lakes Region without giving up access to the amenities you use every day. Waterfront opportunities like this do not often arrive just as Maine's best season begins. Move in, settle back and make this the summer you finally start living on the water.

1 Fern Ave, Windham

Listing courtesy of Spectrum Real Estate.

Selling Office: Signature Homes Real Estate Group, LLC.

$389,000
2 Beds ⋅ 1 Baths
Rare Opportunity in Windham's Sought-After 55+ Community! Condo living opportunities in Windham are few and far between—don't miss your chance for easy, low-maintenance living in this desirable 55+ subdivision! Built in 2017, this beautifully maintained 2-bedroom, 1-bath ranch-style condominium offers comfort, convenience, and modern efficiency. Enjoy one-level living with hardwood and tile floors, granite countertops, and a bright open-concept layout. A sliding glass door in the living room leads to your private side deck—perfect for relaxing or entertaining. The first-floor laundry adds everyday ease, while the full unfinished basement provides abundant storage or potential for future expansion. You'll stay comfortable year-round with efficient natural gas heat and a heat pump with air conditioning. The attached one-car garage offers direct entry for added convenience. Public water, private sewer, and low-maintenance grounds make living here truly effortless. Located just minutes from shopping, dining, and all North Windham amenities, this condo blends peaceful living with in-town convenience. With so few condos available in the area, this is a rare opportunity to secure the easy lifestyle you've been waiting for! Affordable, Efficient, and Move-In Ready! Showings start on Sunday October 26th at the Open House from 10am - 1pm.

8 Matinicus Way Unit Plan#16, Windham

Listing courtesy of Maine Real Estate Experts. YvonneSellsMaine@gmail.com

Selling Office: Keller Williams Realty.

$385,000
3 Beds ⋅ 1 Baths
Move right into this beautifully updated 3-bed, 1-bath home in Windham, located just an easy drive from Portland! This home features wood floors and a stunning updated kitchen with granite countertops and stainless steel appliances. Stay cozy all winter long with the charming woodstove in the basement and a highly efficient Baxi on-demand natural gas heating system. You'll love the peace of mind that comes with big-ticket updates already taken care of, including a newer roof, vinyl siding, and windows. Entertain with ease on the spacious deck, accessible via a sliding glass door that opens to a fenced-in yard--perfect for pets or outdoor activities! A handy storage shed comes with the sale and provides ample room for all your tools and outdoor gear. A perfect blend of comfort, efficiency, and location!

528 Roosevelt Trl, Windham

Listing courtesy of Proper Real Estate Group LLC.

Selling Office: F.O. Bailey Real Estate.

$380,500
2 Beds ⋅ 1 Baths
This 2-bedroom, 1-bath home features comfortable single-level living with a bright, welcoming layout. The living room flows nicely into the kitchen and dining area, creating an easy and functional space for both everyday living and casual entertaining. Set on a manageable 0.26-acre lot, the property provides great outdoor space for gardening, pets, or simply enjoying the yard. Vinyl siding and an asphalt shingle roof add low-maintenance durability. Enjoy easy access to Windham's excellent outdoor amenities, including miles of hiking, biking, and nature trails nearby. Explore the scenic East Windham Conservation Area's multi-mile trail network with forested paths, water views, and connections to the Lowell Preserve system -- perfect for walks, runs, or mountain biking. Conveniently located just minutes from shopping, schools, Windham Center, and Sebago Lake, with an easy commute to Portland, this home combines comfort and convenience in a central location. A wonderful opportunity for first-time buyers, downsizers, or investors! This clean, move-in-ready home features brand-new kitchen appliances and 200-amp electrical service, offering both comfort and peace of mind.

175 Albion Rd, Windham

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

Selling Office: Keller Williams Realty.

$380,000
2 Beds ⋅ 1 Baths
Move right into this beautifully updated 2-bedroom, 1-bath home, perfectly blending comfort, style, and efficiency. With many recent upgrades — including a new kitchen, bathroom, flooring, fresh paint, exterior door, back steps, foundation floor, and roof shingles — this home is ready for you to enjoy. Stay cozy year-round with efficient heating, including a heat pump, and take advantage of the unfinished walkout basement featuring an egress window — ideal for finishing into additional living space, a home office, or guest suite. Soaked in natural light, the interior feels bright and welcoming. Step outside to your private yard, perfect for relaxing, gardening, or entertaining. Enjoy your morning coffee or unwind in the evening on the front deck, a perfect spot for bird watching or soaking in the peaceful surroundings. Located just minutes from town and the turnpike, this home offers the perfect balance of convenience and privacy. Don't miss out — schedule your showing today!

763 River Rd, Windham

Listing courtesy of Fontaine Family-The Real Estate Leader.

Selling Office: Locations Real Estate Group LLC.

$375,000
2 Beds ⋅ 1 Baths
''AMAZING WATERFRONT & SUPERIOR PRIVACY'' This is your chance to own this spectacular waterfront property on Highland Lake with nearly 400' of water frontage on a perfectly private 2.8 Acre setting located conveniently to everything! Take advantage of this chance to have your very own peacefully private oasis on the lake that features a year round home, large sunroom, deck overlooking the lake, dock, breathtaking views, 2 car garage, shed / bunk house, awesome yard & garden area, and more, with the potential for multiple options from it's current use, rentals, or build your own dream lake house! Enjoy the best that Highland Lake has to offer on the water or just relaxing with a cup of coffee listening to the loons or watching the sunrise & bald eagles soar by.... DON'T MISS THIS VERY UNIQUE ONCE IN GENERATIONS OPPORTUNITY!!

22 Dow Ln, Windham

Listing courtesy of Maine Realty 2000.

Selling Office: Keller Williams Realty.

$365,000
2 Beds ⋅ 2 Baths
Welcome to Birchwood Squares Condominiums, where convenience and comfort come together in this charming 2-bedroom, 1.5-bath Condomium. With an attached 1 car garage, durable metal roof, private deck, storage shed and fenced-in , pet friendly yard, this condo offers both low maintenance living and a peaceful retreat. Inside, you'll find tasteful updates, perfect for relaxing or entertaining. Located in the heart of North Windham, this home is only 16 miles from Portland, making for an easy commute. With quick access to I-95 only 6 miles away, travel is effortless. You'll also be just minutes from Windham's shopping, restaurants and entertainment, ensuring everything you need is right at your fingertips. Plus, being in the heart of the Lakes Region, you're surrounded by endless opportunities for outdoor activities, including boating, hiking, golfing, and skiing.

7 Walnut Dr Unit 7, Windham

Listing courtesy of Plowman Realty Group.

Selling Office: Home Port Realty.

$365,000
2 Beds ⋅ 1 Baths
Tucked away on a quiet dead-end road, this charming two-bedroom cottage-style home offers the perfect blend of comfort, privacy, and year-round enjoyment. Thoughtfully and completely remodeled, the home features a warm, welcoming layout filled with natural light and cozy finishes throughout. Unwind in the four-season porch while taking in peaceful winter water views, or enjoy an easy stroll to nearby Highland Lake access—perfect for boating, kayaking, swimming, and summer days on the water. When winter arrives, Highland Lake transforms into a hub for ice fishing and seasonal fun, making this a true four-season retreat. Whether you're seeking a serene weekend getaway or a low-maintenance year-round residence, this home delivers. With close proximity to Portland, you'll love the balance of peaceful lakeside living without sacrificing convenience. A rare opportunity to own a move-in-ready lake-area cottage that checks every box.

50 Overlook Rd, Windham

Listing courtesy of A Team Realty. info@ateammaine.com

Selling Office: A Team Realty.

$360,000
2 Beds ⋅ 2 Baths
Affordable, Move-in Ready Home in a Prime Location. Owned and impeccably maintained by the same family for decades, this charming property offers a rare opportunity for investors and homeowners alike. . The beautifully landscaped lot creates curb appeal with mature trees, while the brand-new roof provides peace of mind for years to come. Inside, you will find a well-cared for home that is ready for its new chapter. Located within walking distance of coffee shops, restaurants, shopping and everyday conveniences. Whether you're searching for your first home, downsizing, or a perfect investment opportunity, this home checks all the boxes. Affordable single-family homes in this price range are becoming increasingly difficult to find. Book your showing now

41 Tandberg Trl, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

Selling Office: Fontaine Family-The Real Estate Leader.

$350,000
3 Beds ⋅ 1 Baths
Nestled in the sought after town of Windham, this charming 1,364 square foot ranch offers the perfect blend of location, comfort, and a peaceful setting. With three spacious bedrooms, 1 bathroom, sizeable kitchen, large windows providing abundant natural light, sunroom, and pellet stove. A new heating system was installed in 2024. This home features a well-designed floor plan ideal for daily living and entertaining. The kitchen overlooks the backyard, offering a sunny spot to enjoy your morning coffee. Inside, you'll find hardwood floors in the living room, a full basement for storage, washer/dryer and a potential 3rd bedroom and or a workshop. This home is secure with a full home alarm and camera security system and two home safes for your valubles. The detached two-car garage boasts plenty of space with a back office. Entertain family and friends with cookouts on your large back deck patio as well roasting marshmellows over the fire pit in your sizable secluded back yard surrounded by trees and an abundance of wildlife. You may even find yourself feeding deer and watching them graze from time to time. Another of many factors that makes this home truly special is its location. Enjoy the convenience of being close to in-town shops, dining, and community events, yet still tucked into a neighborhood that feels calm and welcoming. If you are looking to get-away, you're just: 10 minutes to Sebago Lake for boating, swimming, and summer fun. 15 minutes to Windham's shopping and dining district. 25 minutes to Portland for world-class restaurants, culture, and the Old Port. 45 minutes to skiing at Pleasant Mountain for winter adventure. Whether you're seeking a first home, a right-sized downsize, or a place with room to grow, this property offers the perfect balance of Maine lifestyle and everyday convenience.

42 Barnes Rd, Windham

Listing courtesy of Atienza Commercial & Residential Real Estate Brokers LLC.

Selling Office: Atienza Commercial & Residential Real Estate Brokers LLC.

$347,900
2 Beds ⋅ 2 Baths
Welcome home to Windham Hill Woods, where comfort, convenience, and community come together! This beautifully maintained 2-bedroom, 1.5-bath townhouse offers bright, inviting living spaces and a versatile third-floor loft that's perfect for a home office, guest space, workout room, or cozy retreat. The open layout creates an easy flow for everyday living, while the private back deck provides the ideal spot to unwind and enjoy the peaceful surroundings. The full basement offers plenty of extra storage, giving you all the space you need to stay organized. Best of all, the association takes care of lawn maintenance, snow removal, and exterior upkeep, allowing you to enjoy a truly low-maintenance lifestyle. Windham Hill Woods is known for its outstanding amenities and welcoming community. Spend summer days at the in-ground pool, gather with neighbors in the community garden or gazebo, and enjoy the basketball and pickle ball courts just steps from your door. Conveniently located just minutes from North Windham's shopping, dining, and everyday conveniences, with easy access to the Sebago Lakes Region and only about 25 minutes to Portland, this home offers the perfect balance of recreation, relaxation, and accessibility. Whether you're looking for your first home, a place to simplify your lifestyle, or a move-in-ready property in one of Windham's most desirable communities, this townhouse is one you won't want to miss!

22 Turkey Trail, Unit 22, Windham

Listing courtesy of Dream Home Realty LLC.

Selling Office: Dream Home Realty LLC.

$345,000
3 Beds ⋅ 2 Baths
The picturesque surroundings on the large one-plus-acre lot provide a serene backdrop to your everyday life, offering both tranquility and convenience. The home's inviting layout is perfect for family gatherings or entertaining guests, with its open flow from the living room to the dining area and into the cozy family room. The two porches are perfect for enjoying your morning coffee or unwinding after a long day, while the partially finished basement presents endless possibilities. Whether you're looking to set up a home office, create an in-law suite, or start a small business, this home accommodates your needs with ease. This location puts you in the coveted lakes region, and with the practicality of proximity to Portland, this Bungalow seamlessly blends comfort and convenience, making it the ideal place to call home.

161 Main St, Windham

Listing courtesy of RE/MAX Shoreline.

Selling Office: Coldwell Banker Realty.

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