Homes for Sale near Windham Middle School

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  /28

  $399,900

  $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  10 Abby Rd, Windham, ME 04062

  ✨ 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

  

  Patricia Gallant

  Dream Home Realty LLC

  

  10 Abby Rd, Windham, ME 04062
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  Explore Windham Middle School

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  /82

  $499,900

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft

  22 Montgomery Rd, Windham, ME 04062

  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

  

  Jennifer Whitehead

  Dream Home Realty LLC

  

  22 Montgomery Rd, Windham, ME 04062
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  /35

  $589,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  36 Belvedere Dr, Windham, ME 04062

  Welcome to this beautifully maintained custom Colonial in the desirable Belvedere Estates, offering the feel of a nearly brand-new home with a bright, open-concept design perfect for modern living and entertaining. Gleaming hardwood floors run throughout the home, featuring a stunning kitchen with a large center island, granite countertops, and stainless steel appliances. The kitchen opens

  Megan McShane Redfin Corporation

  

  36 Belvedere Dr, Windham, ME 04062
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  /60

  $735,000

  • 3 Beds
  • 3 Baths
  • 2,520 Sq Ft

  25 Jeffrey Woods Rd, Windham, ME 04062

  If space is what you are looking for, 25 Jeffrey Woods is the property for you. Whether you need to store things in the full basement, have a workshop in the massive garage, build trails on your 12 wooded acres or house visitors in the attached suite, 25 Jeffrey Woods has the room you need. Whether its the floors, trim or cabinets this house is elegantly finished in natural wood tones which give

  Bennett Wade Real Broker

  

  25 Jeffrey Woods Rd, Windham, ME 04062
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  /21

  $479,000

  New Construction $5K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  6 Dolley Farm Rd Unit 3, Windham, ME 04062

  Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Harvest style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining

  Marie Flaherty The Flaherty Group

  

  6 Dolley Farm Rd Unit 3, Windham, ME 04062
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  /41

  $1,645,000

  $145K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,602 Sq Ft

  20 Freeman Ct, Windham, ME 04062

  Located at the end of a quiet cul-de-sac, this exceptional estate combines refined design, extensive recent renovations, and exclusive access to the crystal-clear waters of Maine's premier Sebago Lake -- widely regarded as one of New England's top freshwater destinations for boating, recreation, and year-round beauty. Offering 4,602 square feet of finished living space, this estate features 4

  Corinne Holt Holt Realty

  

  20 Freeman Ct, Windham, ME 04062
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  /16

  $175,000

  $60K PRICE DROP

  • Land
  • 40,075 Sq Ft
  • $190,217 per Acre

  78 Lakeside Dr, Windham, ME 04062

  LAKESIDE LIVING: Discover the perfect blend of privacy, natural beauty, and convenience with this serene, buildable lot featuring two separate deeded access points. Nestled in a peaceful, quiet setting, this property offers a rare opportunity to create your dream home or lakehouse retreat. Much of the groundwork has already been completed--an existing well is in place, the driveway has been

  Ciara Sanfino Engel & Volkers Portsmouth

  

  78 Lakeside Dr, Windham, ME 04062
• 

  

  /19

  $180,000

  • Land
  • 1.6 Acres
  • $112,500 per Acre

  68 Sky Dr, Windham, ME 04062

  The perfect spot to build your dream home in Windham! This 1.6-acre parcel offers a spacious, open lot with a peaceful pond. Sky Drive is a quiet, private road where you'll enjoy privacy and tranquility while still being just minutes from downtown North Windham and the Maine Turnpike. Enjoy the best of Maine living with nearby Sebago Lake and Little Sebago Lake, known for exceptional boating,

  Hannah Richard Locations Real Estate Group LLC

  

  68 Sky Dr, Windham, ME 04062
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  /11

  $1,995,000

  $255K PRICE DROP

  • Land
  • 5.91 Acres
  • $337,563 per Acre

  0 Turning Leaf Dr Unit 1640377, Windham, ME 04062

  •Approved State and Town for a 9,018± SF commercial building, including DEP, DOT, and Portland Water District•DEP & DOT permits approved in 2023 for the 2 building concept•Commercial District 1 Zoning suitable for a variety of uses•Rare parcel of land in one of Maine's fastest growing communities•Easy access to I-95 and other major corridors•Growing community with strong

  Michael Anderson Malone Commercial Brokers, Inc.

  

  0 Turning Leaf Dr Unit 1640377, Windham, ME 04062
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  /109

  $1,230,000

  $165K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,856 Sq Ft

  108 Highland Cliff Rd, Windham, ME 04062

  Welcome to this newly constructed masterpiece in Windham, Maine. Situated on a private, wooded lot, this home blends timeless craftsmanship with modern luxury. Wrapped in durable, low-maintenance LP SmartSide siding, this home is built to withstand Maine's changing seasons while maintaining a stunning aesthetic. The home features premium hydronic radiant heat underfoot, supplemented by

  Shawn Boulet Meservier & Associates

  

  108 Highland Cliff Rd, Windham, ME 04062
• 

  

  /13

  $314,900

  • 1 Bed
  • 1 Bath
  • 766 Sq Ft

  10 Stillwater Dr Unit 1128, Windham, ME 04092

  The Highland offers a peaceful retreat designed for simple, modern living. With 766 square feet of thoughtfully designed space, this one-bedroom, one-bathroom residence blends comfort, style, and convenience in a layout that feels both open and inviting.Inside, contemporary finishes meet everyday functionality with granite countertops, stainless steel appliances, and an in-unit washer and

  Amy Foley Signature Homes Real Estate Group, LLC

  

  10 Stillwater Dr Unit 1128, Windham, ME 04092
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  /74

  $918,500

  • 4 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  27 Independence Dr, Windham, ME 04062

  Escape to this stunning Maine Cedar Log Home! Built in 2003, this impeccably maintained property 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

  Scott Richard Coldwell Banker Team Real Estate

  

  27 Independence Dr, Windham, ME 04062
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  /46

  $594,900

  $25K PRICE DROP

  • 2 Baths
  • 2,252 Sq Ft

  41 Lotts Dr, Windham, ME 04062

  41 Lotts Dr, Windham, ME - Owner-Occupy Opportunity with Income Potential Live in one unit and let the other help pay your mortgage. This well-maintained 2-unit property offers a spacious 3-bedroom unit that will be delivered vacant at closing, paired with a 2-bedroom apartment currently leased to great tenants at $2,200/month. The 3-bedroom unit features single-level living with an open kitchen,

  Sarah Msuya Dream Home Realty LLC

  

  41 Lotts Dr, Windham, ME 04062
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  /32

  $462,000

  • 3 Beds
  • 1 Bath
  • 1,388 Sq Ft

  106 Highland Cliff Rd, Windham, ME 04062

  Tucked on a quiet 1.9-acre lot, this 3-bedroom, 1-bath split-entry home has room to spread out. The main level features an open kitchen that flows into the living room, with hardwood flooring, along with two bedrooms and a full bath. Downstairs, you'll find a third bedroom and a finished bonus room that can easily serve as a home office, gym, playroom, or guest space. A partial wrap-around deck

  Alicia Frechette Ramsey Pulkkinen A Team Realty

  

  106 Highland Cliff Rd, Windham, ME 04062
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  /96

  $975,000

  $24K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,555 Sq Ft

  35 Woldbrook Dr, Windham, ME 04062

  Welcome to the highly desirable Windemere neighborhood on Sebago Lake. This beautifully maintained custom Colonial offers over 3,550 sq. ft. of finished living space with a flexible floor plan designed to accommodate today's multi-generational living needs, including the potential for an in-law suite with kitchenette above the garage.The 5 bedroom and 3.5 baths, including primary suites on

  Jackie Griffeth Krainin Real Estate

  

  35 Woldbrook Dr, Windham, ME 04062
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  /4

  $39,000

  $10K PRICE DROP

  • Land
  • 4,791 Sq Ft
  • $354,545 per Acre

  1 Vista Dr, Windham, ME 04062

  AFFORDABLE WATER ACCESS ! This lot is Non Buildable, however can accommodate a camper or single wide trailer. It has an Easement Deed with Consolidated Communications to have a small equipment building on the property. Consolidated Communications pays all annual taxes. The property has ROW access to Highland Lake.

  William Holmes Cumberland County Realty

  

  1 Vista Dr, Windham, ME 04062
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  /3

  $399,900

  $29K PRICE DROP

  • Land
  • 3.7 Acres
  • $108,081 per Acre

  99 Enterprise Dr, Windham, ME 04062

  The parcel has water stubbed at the road and a gravel curb cut already installed. Ideal location for manufacturing, private warehousing and high bay boat storage.

  Larry Eliason Butts Commercial Brokers

  

  99 Enterprise Dr, Windham, ME 04062
• 

  

  /35

  $284,000

  • 2 Beds
  • 1.5 Baths
  • 833 Sq Ft

  18 Cosmic Way Unit 18, Windham, ME 04062

  Welcome home to this bright and cheerful 2-bedroom, 1.5-bath townhouse-style condo--an ideal opportunity for first-time buyers looking for comfort, value, and convenience. Move right in and enjoy an updated kitchen with granite countertops and stainless steel appliances, along with fresh finishes throughout that make the space feel modern and inviting. The recently added first-floor half bath is

  Susan Sinnett RE/MAX Shoreline

  

  18 Cosmic Way Unit 18, Windham, ME 04062
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  /33

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 1,098 Sq Ft

  12 Turkey Trail Unit 20, Windham, ME 04062

  Excellent Opportunity:Very nice 2 bedroom, 1.5 bath Condominium with a full basement and a nice small back deck. Located in a great Windham location with beautiful grounds and amenities that include a pool, tennis and pickle ball courts, planting area and more all run by an Excellent Association.The home itself has a nice layout and a good flow to it with the Townhouse design. Very

  Jay Weinberg Coldwell Banker Realty

  

  12 Turkey Trail Unit 20, Windham, ME 04062
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  /54

  $849,900

  New Construction $25K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,856 Sq Ft

  23 Pennywhistle Dr, Windham, ME 04062

  Welcome to 23 Pennywhistle Drive, a beautifully designed contemporary farmhouse located in one of Windham's most desirable neighborhoods. Built in 2022 and thoughtfully crafted with both comfort and style in mind, this stunning home offers over 2,400 square feet of beautifully finished living space on a private 1+ acre lot. Inside, you'll find a bright and inviting open-concept layout filled with

  Daneel Dafni Better Homes & Gardens Real Estate/The Masiello Group

  

  23 Pennywhistle Dr, Windham, ME 04062
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  /7

  $85,000

  $35K PRICE DROP

  • Land
  • 1.97 Acres
  • $43,147 per Acre

  8 Beaulieu Dr, Windham, ME 04062

  Buildable lot in great location-- surveyed and town approved. Great location that is close to everything. Beaulieu Drive must be improved to build upon this lot. Road plans and an estimate are in the disclosures.

  Liam McCusker NextHome NorthEast Realty

  

  8 Beaulieu Dr, Windham, ME 04062
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  /30

  $649,900

  • 2 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  1112 Roosevelt Trail Unit 15, Windham, ME 04062

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

  Tom Noonan Allied Real Estate

  

  1112 Roosevelt Trail Unit 15, Windham, ME 04062
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  /100

  $1,225,000

  $25K PRICE DROP

  • 5 Baths
  • 4,580 Sq Ft

  44 Johnson Rd, Windham, ME 04062

  Luxury, Serenity, and Versatility Near Highland Lake 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

  Laura Burden Beacon Realty

  

  44 Johnson Rd, Windham, ME 04062
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  /57

  $665,000

  • 4 Beds
  • 2 Baths
  • 3,444 Sq Ft

  14 Emerson Dr, Windham, ME 04062

  Unique opportunity to own this 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage.Boasting a Single Family home with attached apartment and over 3,000 square feet of finished space the possibilities are endless.

  Justin Robbins Excellence Realty

  

  14 Emerson Dr, Windham, ME 04062
• 

  

  /13

  $349,900

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft

  10 Stillwater Dr Unit 1126, Windham, ME 04092

  Offering 991 square feet of bright, open-concept living, this thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll find timeless shaker-style cabinetry, granite countertops, stainless steel appliances, and an in-unit

  Amy Foley Signature Homes Real Estate Group, LLC

  

  10 Stillwater Dr Unit 1126, Windham, ME 04092
• 

  

  /22

  $149,000

  $10K PRICE DROP

  • Land
  • 1.26 Acres
  • $118,254 per Acre

  53 Johnson Rd, Windham, ME 04062

  Why settle for a small in-town lot when you can enjoy space and privacy just minutes from Portland? This beautiful 1.2-acre parcel in Windham offers the best of both worlds--peaceful surroundings with convenient access to everything you need. The property features a level, wooded setting with mature pine trees, giving it natural character and a serene feel. Even better, it includes lake access,

  Stephen Welsh Plowman Realty Group

  

  53 Johnson Rd, Windham, ME 04062
• 

  /2

  $189,900

  • Land
  • 1.84 Acres
  • $103,207 per Acre

  40 Highland Cliff Rd, Windham, ME 04062

  Back line on a small trout brook with trees, most of the lot is beautiful fields. Nice level loamy lot.

  Reggie Butts Butts Commercial Brokers

  

  40 Highland Cliff Rd, Windham, ME 04062
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  /43

  $1,060,000

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  594 River Rd, Windham, ME 04062

  This large, cherished property has been lovingly preserved by the same family for decades, dating back to its early use by the Girl Scouts for camping and swimming. Encompassing just over 28 acres, the land offers exceptional privacy and includes a rare island in the river where children once camped. One of the property's most distinctive features is the river flowing from Sebago Lake, known for

  Stephen Welsh Plowman Realty Group

  

  594 River Rd, Windham, ME 04062
• 

  

  /13

  $349,900

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft

  10 Stillwater Dr Unit 3133, Windham, ME 04092

  This third floor unit features 9' ceilings and offers 991 square feet of bright, open-concept living. This thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll find timeless shaker-style cabinetry, granite

  Amy Foley Signature Homes Real Estate Group, LLC

  

  10 Stillwater Dr Unit 3133, Windham, ME 04092
• 

  /2

  $275,000

  • Land
  • 2.96 Acres
  • $92,905 per Acre

  0 Cook, Windham, ME 04062

  Rare opportunity to build your dream home/getaway destination or private sanctuary away from it all, yet with conveniences of daily living still nearby. Nestled on a quiet street near the Pleasant River, with sloping hills, mature trees & majestic natural beauty as far as the eye can see, this buildeable Lot of just under 3 Acres, sits in the heart of Town and promises not only the wholesome

  Cristina Eugen Keller Williams Realty

  

  0 Cook, Windham, ME 04062
• 

  

  /43

  $499,000

  $51K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  1112 Roosevelt Trail Unit 8, Windham, ME 04062

  Rare Sebago Lakefront Property! Don't miss this rare opportunity to own a beachfront home on the shores of stunning Sebago Lake with approximately 300 feet of private, sandy shoreline. This exceptional property offers breathtaking sunsets and panoramic views of Sebago Lake and Mount Washington. The home offers an updated kitchen with brand-new stainless steel appliances, modern cabinets and solid

  Brian DuBois Keller Williams Realty

  

  1112 Roosevelt Trail Unit 8, Windham, ME 04062
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  /40

  $699,000

  New Construction $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft

  9 Dusty Rhoades Ln, Windham, ME 04062

  This lovely new Windham property offers the perfect blend of privacy, comfort, and convenience. Inside you'll find an open concept layout with 9 foot ceilings creating a bright and airy atmosphere, with true hardwood oak flooring extending throughout the entire first floor and stairwell for added warmth and character. The home offers 3 bedrooms and 3 bathrooms, including a spacious primary suite,

  Catherine Hodge Salt Real Estate Co

  

  9 Dusty Rhoades Ln, Windham, ME 04062
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  /62

  $889,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  32 Pennywhistle Dr, Windham, ME 04062

  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

  John Hatcher Keller Williams Realty

  

  32 Pennywhistle Dr, Windham, ME 04062
• 

  

  /7

  $155,000

  • Land
  • 1.82 Acres
  • $85,165 per Acre

  132 Roosevelt Trail, Windham, ME 04062

  Ideal Commercial Lot. 1.82 acre lot with many possible uses such as professional office, retail sales, day care, warehousing, wireless tower, medical office, residential, convenience, recreation facility and more.

  Suphi Turker Keller Williams Realty

  

  132 Roosevelt Trail, Windham, ME 04062
• 

  

  /12

  $699,000

  • 2 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  25 Daybreak Ln Unit 8, Windham, ME 04062

  Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 25 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes provide both first and second floor primary suite options. Multi-generational, Companion, and Guest-Friendly, owners of these units can opt

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  25 Daybreak Ln Unit 8, Windham, ME 04062
• 

  

  /22

  $429,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  528 Roosevelt Trail, Windham, ME 04062

  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

  Melissa Ryan-Proper Proper Real Estate Group LLC

  

  528 Roosevelt Trail, Windham, ME 04062
• 

  

  /46

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 2,981 Sq Ft

  24 Leonards Way, Windham, ME 04062

  Welcome to this stunning custom-built 4-bedroom (3 bedroom septic) home nestled in one of Windham's most desirable neighborhoods. Perfectly situated just 15 minutes from Portland and 15 minutes from North Windham's shopping, dining and recreation. This property offers the ideal blend of convenience and peaceful living. Designed with both comfort and entertaining in mind, the home features an

  Brittany Copp Portside Real Estate Group

  

  24 Leonards Way, Windham, ME 04062
• 

  

  /49

  $450,000

  • 4 Beds
  • 1 Bath
  • 1,428 Sq Ft

  14 Birchwood Ave, Windham, ME 04062

  Classic Cape style dormered home in an ideal, quiet neighborhood setting very conveniently located to North Windham's shopping area! A first floor bedroom offers flexibility to use as desired. A large, fenced in backyard and deck provide many opportunities for indoor-outdoor living. The unfinished basement provides great extra storage and additional space to utilize. A well cared for home that is

  Amy Meader Harborview Properties, Inc.

  

  14 Birchwood Ave, Windham, ME 04062
• 

  

  /30

  $950,000

  $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft

  103 Basin Rd, Windham, ME 04062

  This a great opportunity to own a classic lakeside home on the shores of the Sebago Lake Basin. Built in the 1930s and full of timeless character, this charming cottage style home sits right at the water's edge, offering beautiful views of the lake and Lyndsay Island just across the way. Set on a .31 acre lot, the property includes a shed structure and deck perched directly on the shoreline

  David Banks RE/MAX By The Bay

  

  103 Basin Rd, Windham, ME 04062
• 

  

  /30

  $339,900

  $9K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 798 Sq Ft

  549 Roosevelt Trail, Windham, ME 04062

  New Price! Investor, builder, developers, home buyers! Exceptional 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 0.56-acre lot with 137 feet of prime road frontage. An asset for immediate expansion or

  Todd Harvey Pine Tree Realty of Maine

  

  549 Roosevelt Trail, Windham, ME 04062

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