Homes for Sale near Windham High School

• 

  

  

  /46

  $575,000

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft

  2 Chickadee Ln, Raymond, ME 04071

  Welcome to 2 Chickadee Lane in Raymond! This is a rare opportunity to own 40 feet of private sandy frontage on Panther Pond, a stunning 1,400+ acre lake known for its crystal clear water, great fishing, and year round recreation. Tucked into a quiet, protected cove, this property offers a peaceful setting where mornings begin calm and the day unfolds on your terms. With a sandy beach and gradual

  

  Michael Hamilton

  Keller Williams Realty

  (207) 489-2699

  

  2 Chickadee Ln, Raymond, ME 04071
• 

  Explore Windham High School

• 

  

  

  /60

  $975,000

  • 2 Beds
  • 1 Bath
  • 2,212 Sq Ft

  1254 Roosevelt Trail Unit A,B,C, Raymond, ME 04071

  Positioned along the highly desirable Route 302 corridor in the heart of Raymond's Lakes Region, 1254 Roosevelt Trail offers a unique opportunity for both residential enjoyment and investment potential. Set on approximately 0.60 acres, this property enjoys excellent visibility and accessibility while remaining close to the area's most sought-after natural amenities.The property features four

  

  Matthew Martino

  Elevate Maine Realty

  (207) 804-5840

  

  1254 Roosevelt Trail Unit A,B,C, Raymond, ME 04071
• 

  

  

  /18

  $122,500

  • Land
  • 3 Acres
  • $40,833 per Acre

  192 Mountain Rd, Raymond, ME 04071

  Embrace the beauty of Maine's four seasons on this wooded parcel in Raymond. Surrounded by mature trees that burst into brilliant color each autumn, this property offers a peaceful setting for your future home or getaway retreat. The land provides privacy with gently rolling terrain, stone walls, and natural character—ideal for creating trails, gardens, or simply enjoying nature at your doorstep.

  

  Kristen Roy

  Elevate Maine Realty

  (207) 709-0321

  

  192 Mountain Rd, Raymond, ME 04071
• 

  

  

  /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
• 

  

  

  /56

  $1,150,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,350 Sq Ft

  17 Betty Ln, Windham, ME 04062

  Welcome to Edgewood Estates, one of Windham's most sought-after new communities, offering a rare opportunity to own within a thoughtfully designed six-lot setting surrounded by natural beauty. Positioned at the edge of the neighborhood, this home offers a sense of retreat, where protected conservation land becomes your backdrop and everyday living feels quietly elevated. Inside, light pours

  Andrea Page Keller Williams Realty

  

  17 Betty Ln, Windham, ME 04062
• 

  

  /80

  $689,900

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  179 Egypt Rd, Raymond, ME 04071

  Beautifully maintained 3-bedroom, 3-bath ranch in Raymond offering the ease of single-level living with thoughtful upgrades throughout with. The open-concept kitchen and living area features cathedral ceilings, creating a bright and inviting space ideal for both everyday living and entertaining. Set on 5.9 acres and abutting conservation land with a pond and brook, this property offers a

  Lisa DiBiase Landing Real Estate

  

  179 Egypt Rd, Raymond, ME 04071
• 

  

  /96

  $999,000

  • 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
• 

  

  /53

  $874,900

  New Construction

  • 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
• 

  

  /42

  $680,000

  • 3 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  315 River Rd, Windham, ME 04062

  Welcome to 315 River Road in Windham, a well-maintained gambrel-style home offering space, flexibility, and privacy on 4.7 acres. This 3-bedroom, 3-bath home features a true primary suite along with recently updated bathrooms and hardwood flooring. Heat pumps provide efficient heating and cooling, and a whole-house generator offers added peace of mind year-round. The layout offers functional and

  Chris Gerrity Maine Real Estate Experts

  

  315 River Rd, Windham, ME 04062
• 

  

  /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
• 

  

  /44

  $739,000

  New Construction $10K 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 has 3 bedrooms and 3 bathrooms including it's primary suite along

  Catherine Hodge Salt Real Estate Co

  

  9 Dusty Rhoades Ln, Windham, ME 04062
• 

  

  /58

  $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
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  /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
• 

  

  /7

  $799,000

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

  014-17-J01 Mimi Ln, Windham, ME 04062

  Welcome to your opportunity to build a stunning modern farmhouse in the heart of Windham. This thoughtfully designed new construction package blends timeless charm with clean, modern finishes, offering both style and functionality across 2,600 square feet of beautifully crafted living space. This farmhouse style home features 4 spacious bedrooms, 2.5 bathrooms, and a2 car garage, designed with

  Jennifer Sumrall The Maine Real Estate Experience

  

  014-17-J01 Mimi Ln, Windham, ME 04062
• 

  

  /21

  $730,000

  • 2 Beds
  • 1.5 Baths
  • 1,420 Sq Ft

  86 Basin Rd, Windham, ME 04062

  Set in a quiet Sebago Basin setting, this fully renovated 2-bedroom, 1.5-bath home blends classic cottage character with thoughtful modern updates. Inside, the home has been extensively improved with updated systems and carefully selected finishes throughout. Bright, inviting living spaces are filled with natural light, while the renovated primary suite features a beautifully finished en-suite

  Stephanie Retrosi Engel & Volkers Portsmouth

  

  86 Basin Rd, Windham, ME 04062
• 

  

  /57

  $765,000

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  19 Treasure Ln, Windham, ME 04062

  Well-maintained 4-bedroom, 2.5-bath home located on just under 2 acres in desirable Windham. Situated at the end of a private way and surrounded by trees, the property offers a quiet, natural setting with frequent wildlife sightings. Built in 2023, the home has been carefully maintained by the current owners and features tasteful finishes throughout.Offering a balance of rural living and

  Garret Getch EXP Realty

  

  19 Treasure Ln, Windham, ME 04062
• 

  

  /21

  $474,000

  New Construction

  • 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
• 

  

  /37

  $259,000

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  1 Gilleys Ln Unit 5, Raymond, ME 04071

  Discover your own slice of paradise on Crescent Lake in Raymond! This charming, fully furnished cottage is move-in ready and offers the perfect blend of comfort, character, and lakeside living. Warm pine ceilings run throughout the home, with a stunning cathedral ceiling in the main living area creating an open, airy feel. A cozy loft provides additional sleeping space and extra storage, while

  Tiffany Libby Pamela Starnes Signature Homes Real Estate Group

  

  1 Gilleys Ln Unit 5, Raymond, ME 04071
• 

  

  /90

  $1,500,000

  • 3 Beds
  • 3 Baths
  • 3,390 Sq Ft

  23 Casselton Rd, Raymond, ME 04071

  Set in the highly desirable Cathedral Pines neighborhood on Sebago Lake, this exceptional property offers a rare blend of privacy, recreation, and refined lake living. The custom home spans over 3,300 square feet and sits on a beautifully landscaped private lot, paired with 410' of shared sandy beach access and a deeded boat slip, an uncommon offering on one of Maine's most sought after

  Carol Kline Kline Realty Group

  

  23 Casselton Rd, Raymond, ME 04071
• 

  

  /63

  $2,495,000

  • 5 Beds
  • 3.5 Baths
  • 4,311 Sq Ft

  71 Quarry Cove Rd, Raymond, ME 04071

  Set on over two private acres along coveted Jordan Bay of Sebago Lake, this exceptional lakefront retreat offers the perfect blend of luxury, comfort, and classic Maine charm. Tucked into a sheltered cove, the property boasts a rare sandy beach with a gradual entry--ideal for swimming, relaxing, and all-ages enjoyment. The classic post and beam main residence features 4 spacious bedrooms and 2.5

  Amber The Collective Real Estate Co

  

  71 Quarry Cove Rd, Raymond, ME 04071
• 

  

  /44

  $459,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  91 Vista Dr, Windham, ME 04062

  Welcome to 91 Vista Drive in Windham, a well-maintained Highland Lake property offering water views and not one, but two deeded rights of way to the lake. Ideally situated one back from the water, this home gives you the best of lake living without the waterfront taxes. The sellers have meticulously cared for and thoughtfully improved the property over the years. In 2014, the home was lifted and

  Tyler Tran Keller Williams Realty

  

  91 Vista Dr, Windham, ME 04062
• 

  

  /8

  $180,000

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

  68 Sky Dr, Windham, ME 04062

  Looking for land in Windham? Look no further! Check out this beautiful 1.6 acre parcel ready for your next build. A wonderful, open lot with a pond. Located on a quiet, private road only a few minutes to town and the Maine Turnpike. Tucked away, yet close to everything you need. Close to Sebago Lake and Little Sebago Lake for some of Maine's best boating, fishing and swimming. Only a 35 minute

  Hannah Richard Locations Real Estate Group LLC

  

  68 Sky Dr, Windham, ME 04062
• 

  

  /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
• 

  

  /63

  $535,000

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,052 Sq Ft

  97 Tenny Hill Rd, Raymond, ME 04071

  Experience the perfect blend of modern comfort and secluded serenity in this meticulous Raymond colonial. Set on 5 private acres of pristine Maine woodland, this property offers direct access to a walking trail right in your own backyard. The home's exterior has been freshly painted and is topped with a brand-new roof, providing immediate curb appeal and peace of mind. Inside, the main level

  Christina Connell Berkshire Hathaway HomeServices Verani Realty

  

  97 Tenny Hill Rd, Raymond, ME 04071
• 

  

  /46

  $609,900

  $10K 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
• 

  

  /91

  $624,900

  • 3 Beds
  • 2 Baths
  • 2,032 Sq Ft

  255 Raymond Hill Rd, Raymond, ME 04071

  Welcome to Gladstone Manor, a historic 1704 farmhouse beautifully set on two picturesque acres and rich with character. The property includes 30 feet of waterfront on pristine Raymond Pond, offering the potential for a private dock to enjoy boating, swimming, and easy lakeside living. The home features two kitchens, making it ideal for a potential in-law suite or guests, while upstairs you'll

  Terry Hewitt Keller Williams Realty

  

  255 Raymond Hill Rd, Raymond, ME 04071
• 

  

  /49

  $549,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,018 Sq Ft

  8 Colina Dr, Raymond, ME 04071

  This Cape-style home sits on 3 scenic acres with plenty of room for enjoying the outdoors. This home has so much to offer! Oversized attached garage with direct entry to the main level offering a mudroom, kitchen with a center island, dining area, living room, full bath with laundry, and a primary bedroom. Upstairs you'll find two more bedrooms and another full bath. The lower level features a

  Alicia Frechette Ramsey Pulkkinen A Team Realty

  

  8 Colina Dr, Raymond, ME 04071
• 

  

  /16

  $2,995,000

  New Construction

  28 Fire Lane 33, Raymond, ME 04071

  The setting is unparalleled, the plans are in place - this is a rare opportunity for a dream retreat on Sebago Lake! Set off of Raymond Cape Road, this 2 acre property has prime Western exposure, with views of the mountains, postcard sunsets, and direct access to your own sandy shoreline. Fully planned and ready for completion, this home offers a rare opportunity for a builder or visionary buyer

  David Banks RE/MAX By The Bay

  

  28 Fire Lane 33, Raymond, ME 04071
• 

  

  /5

  $203,000

  $7K PRICE DROP

  • Land
  • 5.1 Acres
  • $39,804 per Acre

  0 Mountain Rd, Raymond, ME 04071

  Come build your dream home on this beautiful wooded parcel in Raymond Maine! The 5.1 acres will provide privacy with gently rolling terrain and stone walls, ideal for creating gardens or simply enjoying nature at your doorstep. During Autumn, the trees transform into a stunning palette of colors, creating a breathtaking spectacle. Conveniently located near Sebago Lake, Crescent Lake, and Raymond

  Tina White Plowman Realty Group

  

  0 Mountain Rd, Raymond, ME 04071
• 

  

  /3

  $425,000

  $4K PRICE DROP

  • Land
  • 3.7 Acres
  • $114,865 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
• 

  

  /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
• 

  

  /30

  $1,499,000

  • 3 Beds
  • 1.5 Baths
  • 1,294 Sq Ft

  40 Dyer Rd, Raymond, ME 04071

  Some properties you tour, this one you feel. Tucked into 215 acres of genuine countryside - not manicured, not curated, just real land - this log home has the kind of character you can't manufacture. Hand-hewn walls, hardwood floors worn to a beautiful patina, and a stone fireplace big enough to gather around on a cold night. It doesn't feel like a retreat. It is one.The kitchen and dining

  Tim Flaherty The Flaherty Group

  

  40 Dyer Rd, Raymond, ME 04071
• 

  

  /100

  $1,632,000

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  114 Wild Acres Rd, Raymond, ME 04071

  SEBAGO LAKE - Jordan Bay Waterfront!Privately nestled down a quiet way, this exceptional 4BR, 3BA year-round lake home offers 90 feet of pristine, deep-water frontage on the crystal-clear waters of Jordan Bay. A rare highlight of this property is its true sandy beach, beautifully defined and usable at all water levels. Perfect for swimming, lounging, and effortless lake enjoyment all season

  Shannon Boyington Coldwell Banker Realty

  

  114 Wild Acres Rd, Raymond, ME 04071
• 

  

  /75

  $659,000

  • 3 Beds
  • 4 Baths
  • 2,609 Sq Ft

  Unlisted Address

  ''BEST OF EVERYTHING!'' This property is everything you've been looking for and more with an ideal combination of home, lot, location & value!! This magnificent property boasts a meticulously maintained custom Cape Cod style home ideally situated on a spectacular sun drenched well manicured 2.38 acre lot that is conveniently located near everything with a uniquely private & picturesque setting!

  Bruce Ludka Maine Realty 2000

  

  Unlisted Address
• 

  

  /22

  $159,000

  • Land
  • 1.26 Acres
  • $126,190 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
• 

  

  /43

  $3,500,000

  • 8 Beds
  • 5.5 Baths
  • 4,800 Sq Ft

  12 Bayview Dr, Raymond, ME 04071

  This unique lakefront setting provides convenient access to the pristine waters of Sebago Lake's Jordan Bay. The Sebago Lake Region is well known for its four-season recreational activities that include outstanding boating, swimming, fishing, golfing, and winter downhill skiing, all within 25± miles. This special lakefront property embraces everything that is Maine from the cry of loons on the

  John Saint-Amour LandVest, Inc.

  

  12 Bayview Dr, Raymond, ME 04071
• 

  /2

  $525,000

  • Land
  • 49.7 Acres
  • $10,563 per Acre

  Lot 4 Highland Cliff Rd, Windham, ME 04062

  Welcome To Lot 4 Highland Cliff Road. This Beautiful 49.7 +/- Acre Parcel Has A Lot Of Options. Located in Windham off of the very popular Highland Cliff Road, Property is partially through the subdivision process as Phase 2 of the Canada Hill Subdivision, but very developable as a new subdivision (Talk to the planning board), or even just a very private spacious single lot. There is also an

  William Noone Getty Real Estate Services, LLC

  

  Lot 4 Highland Cliff Rd, Windham, ME 04062
• 

  

  /61

  $589,000

  • 3 Beds
  • 2.5 Baths
  • 2,472 Sq Ft

  28 Adam Roberts Dr, Windham, ME 04062

  This beautifully updated Colonial Farmhouse is the perfect blend of charm, comfort, and modern upgrades in a truly picturesque setting. Just 10 minutes to Gorham and 20 minutes to Falmouth, Portland, and Sebago, this ideal location boasts both serenity and convenience. Surrounded by gorgeous perennial gardens, apple trees, and peaceful outdoor living spaces, the property features a welcoming

  Julie Court JC North East Real Estate

  

  28 Adam Roberts Dr, Windham, ME 04062
• 

  /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

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