101

Homes for Sale near Windham High School

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  • /58

    $599,000

    $46K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 3,553 Sq Ft

    28 Oakledge Hills Rd, Raymond, ME 04071

    Summer is here and Vacation is no further than your own back yard! This spacious, custom L-shaped ranch offers over 6.5 acres of privacy, space, and scenic beauty with an excellent opportunity for multigenerational living. Recently enhanced with a newly expanded yard (fresh grass coming in everyday), freshly painted interior, new flooring in the 3rd bedroom and a brand-new roof, this home is

    Agent Photo

    Ashley Fearon

    A Team Realty

    28 Oakledge Hills Rd, Raymond, ME 04071
  • /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

    Agent Photo

    Patricia Gallant

    Dream Home Realty LLC

    10 Abby Rd, Windham, ME 04062
  • /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

    Agent Photo

    Matthew Martino

    Elevate Maine Realty

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

    Agent Photo

    Jennifer Whitehead

    Dream Home Realty LLC

    22 Montgomery Rd, Windham, ME 04062
  • /78

    $4,400,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,080 Sq Ft

    32 Hutchins Rd, Raymond, ME 04071

    The moment you reach the driveway, the lake is already yours - a clear line of sight straight through the glass entry, across the great room, to the water beyond. Inside, an entire wall of glass folds wide open to 100 feet of private, sandy beachfront on Sebago, dissolving the line between indoors and shoreline until there is no division at all. This is a rare opportunity to own a true legacy

    Agent Photo

    Patricia Gallant

    Dream Home Realty LLC

    32 Hutchins Rd, Raymond, ME 04071
  • /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
  • /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
  • /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
  • /92

    $4,750,000

    Coming Soon
    • 6 Beds
    • 5 Baths
    • 4,872 Sq Ft

    15 Sleepy Hollow Rd, Windham, ME 04062

    This property was built for fun and relaxation. Sited on the most desirable spots on Big Sebago Lake's Gold Coast with wide open lake views, amazing sunsets and views of snowcapped Mt. Washington. 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.

    Karen Tufts Coldwell Banker Team Real Estate

    15 Sleepy Hollow Rd, Windham, ME 04062
  • /38

    $475,000

    • 4 Beds
    • 3 Baths
    • 3,820 Sq Ft

    23 Raymond Hill Rd, Raymond, ME 04071

    Duncan Smith EXP Realty

    23 Raymond Hill Rd, Raymond, ME 04071
  • /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
  • /70

    $1,395,000

    $105K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,390 Sq Ft

    23 Casselton Rd, Raymond, ME 04071

    Nestled in the highly sought after Cathedral Pines community on Sebago Lake, this exceptional property offers the perfect blend of luxury, recreation and year round enjoyment. Set on a beautifully landscaped private lot, this custom built home encompasses 3,300 sq ft and is just a quick minute golf cart ride from 410' of shared sandy beach, a deeded boat slip and a scenic lakeside point where

    Carol Kline Kline Realty Group

    23 Casselton Rd, Raymond, ME 04071
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /49

    $2,300,000

    • 4 Beds
    • 2 Baths
    • 1,707 Sq Ft

    102 Musson Rd, Raymond, ME 04071

    There is something truly special about this Sebago Lake property--where luxury, comfort, and unforgettable lake memories come together. This stunning waterfront compound delivers unmatched privacy, protected frontage, and exceptional craftsmanship. The main house and guesthouse sit on 1.26 acres, boasting 326 ft+/- of water frontage. The island in front serves as a picturesque landmark, while

    Heather Shields Legacy Properties Sotheby's International Realty

    102 Musson Rd, Raymond, ME 04071
  • /14

    $2,995,000

    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
  • /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
  • /45

    $374,900

    $4K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    6 Lookout Ln, Raymond, ME 04071

    Set at the end of a quiet road with no through traffic, this 1,300-square-foot contemporary colonial delivers a blend of privacy and potential on 3.6 wooded acres. The home features three bedrooms and one full bath over three levels of living space.The expansive lot creates opportunities to grow--whether that means future additions, an accessory dwelling unit, or a substantial garage or

    Bryce Hamilton Coldwell Banker Realty

    6 Lookout Ln, Raymond, ME 04071
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /19

    $509,900

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    130 Tenny Hill Rd, Raymond, ME 04071

    To be Built: Be the first to own this beautifully designed 1,300-square-foot ranch-style home set in a peaceful Raymond location. Offering 3 bedrooms, 2 full bathrooms, and an oversized attached 2-car garage, this thoughtfully planned home combines modern convenience with comfortable single-level living. The open-concept kitchen, dining, and living area serves as the heart of the home, creating

    Derek Drumtra Ray Landing Real Estate

    130 Tenny Hill Rd, Raymond, ME 04071
  • /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

    $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
  • /113

    $7,200,000

    • 5 Beds
    • 4 Baths
    • 3,763 Sq Ft

    19 Tapley Cove Rd, Raymond, ME 04071

    I'm thrilled to introduce a rare opportunity in the desirable Burnell Cove on Sebago Lake, Maine. This beautiful property offers 650 feet of private lakefront, a pristine private beach, breathtaking sunset views, and a recently renovated cottage. The main home spans 3,100 square feet and features multiple stone fireplaces, a three-season porch with panoramic views, and expansive living areas.

    Kaitlyn Mooers Coldwell Banker Realty

    19 Tapley Cove Rd, Raymond, ME 04071
  • /100

    $1,575,000

    $57K PRICE DROP
    • 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. The true highlight? Not one, but TWO incredible sandy beaches 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
  • /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
  • /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

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