101

Homes for Sale near Windham High School

Section Image
  • /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
  • /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
  • /51

    $565,000

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    10 Jones Rd, Raymond, ME 04071

    A Maine dream come true! This cozy, well-maintained year-round cottage offers private waterfront access with direct entry to beautiful Big Sebago Lake--one of New England's most sought-after destinations. Enjoy peaceful mornings and water views from the enclosed porch overlooking your private dock, excellent fishing opportunities await. Inside, you'll find an inviting open-concept layout

    Alicia Frechette Ramsey Pulkkinen A Team Realty

    10 Jones Rd, Raymond, ME 04071
  • /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
  • /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
  • /28

    $2,200,000

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 3,125 Sq Ft

    57 Andersen Rd, Raymond, ME 04071

    Welcome to Sebago Lake, where this state-of-the-art retreat awaits its new owners. Formed 14,000 years ago by retreating glaciers, this extraordinary setting of granite boulders and pristine shoreline frames Maine's 2ndlargest lake. Built into that landscape in 1984, the home has been thoughtfully enhanced during the current owner's stewardship with purposeful, creative improvements that honor

    Chessell McGee Legacy Properties Sotheby's International Realty

    57 Andersen Rd, Raymond, ME 04071
  • /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
  • /58

    $498,000

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft

    20 Swans Rd, Raymond, ME 04071

    Located directly across from the water, this multi-level home includes a deeded right of way to Raymond Pond shared by only four homes -- an easy way to enjoy lake life in the heart of Maine's Lakes Region. Enjoy water views and lake access without the cost of waterfront ownership. Inside, the home features an open-concept layout with soaring ceilings and a spacious feel throughout. The kitchen

    Lindsay Anderson Keller Williams Realty

    20 Swans Rd, Raymond, ME 04071
  • /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
  • /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
  • /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
  • /74

    $1,600,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,024 Sq Ft

    36 Whittemore Cove Rd, Raymond, ME 04071

    Enjoy exceptional waterfront living on Big Sebago Lake from this beautifully updated property set on 1.75 acres in a protected cove with 90 feet of sandy, gradual-entry frontage--ideal for swimming, boating, and relaxing at the shoreline. The property includes a modular dock system with jet ski lift, making lake access easy and convenient all season long. This furnished 4-bedroom, 3.5-bathroom

    Jackie Griffeth Krainin Real Estate

    36 Whittemore Cove Rd, Raymond, ME 04071
  • /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
  • /81

    $589,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,196 Sq Ft

    18 Martin Heights, Raymond, ME 04071

    Meticulously updated home nestled on a beautiful lot in the highly sought-after Martin Heights community. This property offers peace of mind with extensive recent improvements, including a new metal roof (2025), new well water system (2025), replaced radon air fan (2025), and generator hookup. Additional upgrades include mini split system, jet pump, air well, and a water softening system with ion

    Libby Brackett Real Broker

    18 Martin Heights, Raymond, ME 04071
  • /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
  • /29

    $479,000

    New Construction $10K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    12 Dolley Farm Rd Unit 6, 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

    12 Dolley Farm Rd Unit 6, Windham, ME 04062
  • /62

    $549,900

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,056 Sq Ft

    31 Brand Rd, Windham, ME 04062

    Come visit this oversized cape in a lovely part of town! This home offers ample space, a bonus room above the garage with little work to make it complete and beautiful frontage on Pleasant River to toss in a kayak right out your back door. Many desirable features including direct basement access from the garage, a full rear dormer on the second floor, a master suite, a formal dining room and

    Bonnie Kent Dan Anderson Real Estate, Inc.

    31 Brand Rd, Windham, ME 04062
  • /37

    $360,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,272 Sq Ft

    6 Outlaw Ridge Rd, Raymond, ME 04071

    Welcome to 6 Outlaw Ridge Rd! Conveniently located just minutes from New Gloucester, Poland, Windham, and Gray, this 3 bedroom, 1 bath home offers a great opportunity to add your personal style and build equity. Situated on 2.17 acres, the property features a peaceful natural setting with a small private pond, patio area, and room to enjoy the outdoors. Inside, you'll find additional partially

    Jennifer Sumrall The Maine Real Estate Experience

    6 Outlaw Ridge Rd, Raymond, ME 04071
  • /40

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft

    80 Vista Dr, Windham, ME 04062

    Perched along the shore of Highland Lake, this exceptional four season waterfront home offers the perfect combination of comfort, recreation, and convenience. Whether you envision quiet weekends by the lake, hosting family and friends all summer long, or generating seasonal rental income, this property delivers an unmatched lakefront lifestyle in one of Southern Maine's most desirable and

    Kelli Brewer Portside Real Estate Group

    80 Vista Dr, Windham, ME 04062
  • /67

    $2,000,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    20 Ladyslipper Dr, Windham, ME 04062

    New construction on Little Sebago Lake is a once-in-a-decade event. And this is that event. A sun drenched contemporary three-story residence modeled after a Maine Home + Design award winning home and sited on a private dead-end road shared by just six year-round properties. This home faces DUE WEST, so that every room on the waterside catches the full arc of sunset through the floor-to-ceiling

    Judy George Judy George Realty

    20 Ladyslipper Dr, Windham, ME 04062
  • /7

    $785,000

    $14K PRICE DROP
    • 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
  • /17

    $162,500

    $10K PRICE DROP
    • Land
    • 1.17 Acres
    • $138,889 per Acre

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

    Tucked away on a quiet dead end road, this beautiful 1.17-acre parcel offers the perfect blend of privacy and convenience in the heart of Windham. With no association fees and situated on a private road, this is your opportunity to create the lifestyle you've been dreaming of, without the restrictions. Enjoy the peaceful setting while being just minutes from shopping, dining, and everyday

    Jennifer Sumrall The Maine Real Estate Experience

    014-17-J01 Mimi Ln, Windham, ME 04062
  • /42

    $619,000

    $30K PRICE DROP
    • 2 Baths
    • 2,710 Sq Ft

    305 Gray Rd, Windham, ME 04062

    Gorgeous Duplex in Windham Offering Strong Rental Income! This well maintained property features long-term tenants. Rich in character, the home showcases beautiful exposed beams and warm wood features throughout, blending charm with functionality. Recent updates include a new roof, new back deck and stairs, and an oversized shed that conveys with the property for additional storage, currently

    Jennifer Sumrall The Maine Real Estate Experience

    305 Gray Rd, Windham, ME 04062
  • /55

    $575,000

    • 2 Baths
    • 1,728 Sq Ft

    243 Windham Center Rd, Windham, ME 04062

    Turn-key duplex in a convenient Windham location. Both units offer 2 bedrooms and 1 bathroom and have been freshly updated with new paint, newer siding, and a newer roof. Located close to schools with an easy commute to Portland. The property is vacant and ready for owner occupancy, or rent out both units for investment income. A great opportunity for an owner occupant or investor looking for a

    Samantha Bell Coldwell Banker Team Real Estate

    243 Windham Center Rd, Windham, ME 04062
  • /96

    $969,900

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

    35 Woldbrook Dr, Windham, ME 04062

    OPEN HOUSE SATURDAY JUNE 20th, 12 to 2. Experience the best of Sebago Lake living in the highly sought-after Windemere neighborhood. This custom-built Colonial offers over 3,550 square feet of beautifully finished living space with a versatile layout ideal for today's lifestyle, including the potential for an in-law suite or guest quarters above the garage with a kitchenette. The home features 5

    Jackie Griffeth Krainin Real Estate

    35 Woldbrook Dr, Windham, ME 04062
  • /41

    $550,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    3 Frenchmans Ln, Windham, ME 04062

    COMING SOON - Showings begin on Friday 7/3 Serene, private, and peaceful. The scent of Maine pines & the sight of deer meandering by. A quiet, welcoming neighborhood. This 3-bedroom, 3-bath colonial will always have you hustling home! Inside, lofty ceilings, natural light, hardwood & tile floors, and a floorplan that flows await. The kitchen's granite countertops, smart refrigerator, double oven,

    Bridget King Jason Miller King + Miller Real Estate

    3 Frenchmans Ln, Windham, ME 04062
  • /14

    $139,000

    $61K PRICE DROP
    • Land
    • 2.11 Acres
    • $65,877 per Acre

    30 Marshall Valley Rd, Windham, ME 04062

    Location, Location, Location!! Welcome to 30 Marshall Valley Road. This 2.11 Acre Buildable Lot has everything from privacy with a country setting, to a babbling brook in the back of the Lot. All perfectly Set off of Highland Cliff Road in Windham!! The Seller has removed the build package from the MLS, and opened the lot up to any sale, any Builder (bring your own Builder), any Developer, or

    William Noone Getty Real Estate Services, LLC

    30 Marshall Valley Rd, Windham, ME 04062
  • /50

    $659,000

    • 3 Beds
    • 2.5 Baths
    • 2,214 Sq Ft

    13 Maysens Way, Windham, ME 04062

    'AMAZING HOUSE, LOT, LOCATION & VALUE' This is the property you've been searching for with the perfect combination of everything you are looking for!! This beautifully cared for newer home has bright spacious rooms with an awesome plan that is both comfortable and versatile. Nestled on one of the prettiest lots in a very desirable small neighborhood with a dead end and gorgeous sun-drenched

    Bruce Ludka Maine Realty 2000

    13 Maysens Way, Windham, ME 04062
  • /61

    $825,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,366 Sq Ft

    25 Leonards Way, Windham, ME 04062

    Welcome to 25 Leonards Way! Set on a beautifully maintained 0.84-acre lot in one of Windham's sought-after established neighborhoods, this exceptional property offers the perfect blend of elevated finishes, everyday comfort, & an unbeatable location. Built in 2021, this beautifully kept 4-bedroom, 2.5-bath home offers nearly 2,400 square feet of thoughtfully designed living space with high-end

    Emilie Levecque Portside Real Estate Group

    25 Leonards Way, Windham, ME 04062
  • /5

    $325,000

    • Land
    • 34,412 Sq Ft
    • $411,392 per Acre

    1042 Roosevelt Trail, Windham, ME 04062

    This .79 +/- acre lot has deeded rights to pass and repass on foot by the right of way from the County Road to Sebago Lake, and to pass and repass on foot along the shore of said Sebago Lake. The site offers an opportunity to build a spacious new home set back from the road along with an in-home business use and/or accessory apartment Alternatively, this site offers an opportunity to develop a

    Larry Eliason Butts Commercial Brokers

    1042 Roosevelt Trail, Windham, ME 04062
  • /2

    $235,000

    • Land
    • 1.84 Acres
    • $127,717 per Acre

    39 Cook Rd, 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

    39 Cook Rd, Windham, ME 04062
  • /21

    $350,000

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 878 Sq Ft

    402 Roosevelt Trail, Windham, ME 04062

    402 Roosevelt Trail offers the perfect blend of recent updates, convenience, and space to enjoy Maine living. Situated on a generous 1.42-acre lot, this property features a spacious, fully fenced backyard--ideal for entertaining, pets, or simply relaxing in your own private outdoor setting.Significant improvements completed by the previous owner in 2024 include a new roof, new leach field,

    Amato Polselli Benchmark Real Estate

    402 Roosevelt Trail, Windham, ME 04062
  • /6

    $79,900

    • Land
    • 1.97 Acres
    • $40,558 per Acre

    8 Beaulieu Dr, Windham, ME 04062

    Lovely almost 2-acre lot in a great location.Surveyed and town approved. Beaulieu Drive needs to be improved by the buyer to Minor Road Standard. Road plans are available

    Richard Yost NextHome NorthEast Realty

    8 Beaulieu Dr, Windham, ME 04062
  • /52

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 2,494 Sq Ft

    58 Thrush Terrace, Windham, ME 04062

    Stunning Colonial set at the end of a quiet cul-de-sac, nestled along a tranquil pond and perfectly positioned for privacy. Situated on a lot larger than most in the neighborhood, this property offers exceptional outdoor space. Inside, the home features an open layout with beautiful hardwood flooring. The kitchen with center island flows into the dining area and family room with fireplace,

    Alicia Frechette Ramsey Pulkkinen A Team Realty

    58 Thrush Terrace, Windham, ME 04062

Showing Results 41 - 80, Page 2 of 3

How to Buy a Home How to Finance a Home How to Sell a Home