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12 Natalie Ln, Windham
$719,000
3 Beds ⋅ 2 Baths
Sprawling contemporary ranch home situated on a private 1.8 lush green lot which is impeccably landscaped. Over 2000 sq feet of living space including a sunny living room with gas fireplace and cathedral ceiling. Wonderfully planned out kitchen with pantry, center island and dining area, large flex space room with a wood stove, primary suite with full bath, 2 additional bedrooms and another full bath with laundry area. FHW propane radiant floor heat makes the floors warm in the winter. Solar panels supplement hot water for efficiency. Attached oversized two car garage and detached one car garage. Backyard oasis with covered patio area. The rear yard garden shed offers additional storage. Rarely does a property this private in such a wonderful setting become available. ABSOLUTE MUST SEE!

12 Natalie Ln, Windham

Listing courtesy of Portside Real Estate Group.

78 Lakeside Dr, Windham
$599,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION TO BE BUILT: Experience the best of lakeside living with this stunning new construction opportunity. This thoughtfully designed 3-bedroom, 2-bath home offers modern finishes, open-concept living, and the rare chance to personalize the home to fit your lifestyle. Nestled in a peaceful, scenic setting, the property includes two deeded access points to the lake, making it easy to enjoy swimming, kayaking, fishing, or simply taking in the tranquil waterfront surroundings. Surrounded by nature and nearby trails, this location offers the perfect balance of outdoor recreation and everyday comfort. The home can be customized, with additional options available such as a garage, daylight basement, expanded living space, and other upgrades to create your ideal home. Enjoy the serenity of lake life while remaining just 20 minutes from Portland, offering convenient access to shopping, dining, entertainment, and major commuting routes. Whether you're looking for a year-round residence or a peaceful retreat, this modern new construction home is a unique opportunity to build the lifestyle you've been dreaming of.

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

605 River Rd, Windham
$849,900
3 Beds ⋅ 3 Baths
Nestled on an extraordinary 16-acre estate in the heart of Windham, this one-of-a-kind farmhouse masterfully blends timeless New England charm with exceptional modern amenities. Surrounded by breathtaking stone walls, spectacular perennial gardens, and stunning custom hardscaping, the property offers an unparalleled setting of beauty, privacy, and tranquility. At the heart of the home is a dream chef's kitchen, thoughtfully designed for both everyday living and entertaining. Featuring gleaming granite countertops, stainless steel appliances, and a coveted Wolf gas range, this impressive space is as functional as it is beautiful. The home offers three spacious bedrooms and two-and-a-half baths, with inviting living spaces that embrace the surrounding landscape. Relax year-round in the passive solar sunroom, unwind on the spacious screened porch, or entertain on the deck before soaking in the hot tub beneath the stars. Additional highlights include a three-car garage, a garden shed, and an expansive third-floor attic with incredible potential to create additional finished living space, whether you envision a home office, studio, guest suite, or recreation room. Every inch of this remarkable property reflects thoughtful craftsmanship and pride of ownership. From the magnificent gardens to the picturesque stonework and peaceful acreage, this is a rare opportunity to own a truly exceptional country estate--offering the perfect balance of elegance, comfort, and natural beauty, just minutes from all that Windham has to offer. This home has even been pre-inspected for the buyer's convenience. Seller Concessions Available. For a video walk-thru go to YouTube and enter the property address.

605 River Rd, Windham

Listing courtesy of Keller Williams Realty.

14 Family Cir Unit 2, Windham
$399,900
2 Beds ⋅ 1 Baths
Don't miss this opportunity to own a year-round, two-bedroom cottage on beautiful Sebago Lake! Located in a five-member association, this property includes its own deep-water boat slip, making it ideal for boating enthusiasts. The renovation has already begun, as shown in the photos, giving the next owner a head start on creating their perfect lakeside retreat. The seller has decided to move on before completing the project, creating an excellent opportunity to add your own style and finishing touches. Enjoy the level common waterfront area featuring picnic tables, a fire pit, and plenty of space to relax and gather with family and friends. With a reduced list price, this cottage offers outstanding value and endless potential. Bring your vision and make this Sebago Lake getaway your own!

14 Family Cir Unit 2, Windham

Listing courtesy of Real Estate 2000 ME/NH.

26 Whites Bridge Rd Unit 26, Windham
$284,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and inviting three-bedroom condo, ideally located in the heart of Windham. Enjoy the convenience of being just minutes from shopping, restaurants, and everyday amenities while tucked away in a peaceful setting. The first floor features an open-concept layout with a spacious living room, kitchen, and dining area--perfect for both everyday living and entertaining. Just off the dining area, step onto the newer deck, an ideal spot to enjoy your morning coffee, dine outdoors, or unwind after a long day. Upstairs, you'll find two generously sized bedrooms with cathedral ceilings that create a bright and airy feel, along with a full bathroom. The finished walk-out basement offers valuable additional living space that can easily serve as a third bedroom, home office, fitness room, or family room, with direct access to the private backyard. Conveniently located near Sebago Lake and just a short drive to Portland, this move-in-ready condo offers the perfect blend of comfort, functionality, and location. Don't miss your opportunity to make this wonderful property your new home!

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

630 Roosevelt Trl Unit 1, Windham
$689,000
Prime commercial opportunity with outstanding exposure and ample parking! This stylish, modern office building offers excellent signage visibility along high-traffic Route 302 and flexible C-1 zoning that allows for a variety of uses. With 14 parking spaces and two separate entrances, the building is well-suited for owner occupancy with tenant income. The first level features a welcoming reception area, conference room with gas fireplace, kitchenette, private office with its own entrance, and an ADA-compliant half bath. The second floor includes five offices and a full bathroom. A full basement with double-door access from the parking lot provides excellent loading, storage, or future expansion potential. Built in 2017, the property features modern systems including central air conditioning, a full security system, and irrigation. The association covers plowing and landscaping, making this an attractive, low-maintenance investment. Don't miss the opportunity to elevate your business in this highly visible, turnkey location.

630 Roosevelt Trl Unit 1, Windham

Listing courtesy of Signature Homes Real Estate Group.

214 Tandberg Trl, Windham
$499,999
4 Beds ⋅ 2 Baths
Welcome to this beautifully maintained, move-in ready home in a highly desirable Windham location. Set back from the road with a spacious driveway, oversized two-car garage, and private backyard, this property combines comfort, privacy, and convenience. The recently renovated kitchen flows seamlessly into the updated living room, creating a bright and inviting space for everyday living and entertaining. Fresh paint throughout enhances the clean, modern feel, while the brand-new laundry room adds both style and functionality. With 3-4 bedrooms and two full bathrooms, the flexible floor plan provides a variety of possibilities, including guest accommodations, a home office, hobby space, or additional living areas. Natural gas and public water add to the convenience of ownership. Outside, enjoy the privacy of the backyard along with a generous driveway providing ample parking for multiple vehicles or recreational equipment. Located just minutes from Sebago Lake, local beaches, boating, hiking trails, shopping, dining, and everything the Windham area and the Lakes Region have to enjoy, this home features thoughtful updates, a functional layout, and an exceptional location. Don't miss the opportunity to make this beautifully updated property your next home.

214 Tandberg Trl, Windham

Listing courtesy of Maine Real Estate Co.

3 Lieutenants Dr, Windham
$599,900
3 Beds ⋅ 3 Baths
Built in 2019 and thoughtfully designed for today's lifestyle, this move-in ready Colonial offers the perfect balance of modern comfort, privacy, and convenience. Situated on a private 1.17-acre lot in the desirable Riverside Ridge neighborhood, this home provides a peaceful setting while remaining just minutes from shopping, restaurants, schools, the Maine Turnpike, and a short drive to the recreational opportunities of Sebago Lake. Designed with both everyday living and entertaining in mind, the open-concept main level features an eat-in kitchen with granite countertops, a center island, pantry, and seamless flow into the dining and living areas. In addition to the reported living area, the home features a fully finished and heated bonus room above the attached two-car garage, offering exceptional flexibility as a home office, media room, game room, fitness area, playroom, or guest retreat. Upstairs, the spacious primary suite offers a private bath and walk-in closet, while two additional bedrooms and second-floor laundry add comfort and convenience. Enjoy your morning coffee on the inviting front porch or unwind on the private rear deck overlooking the spacious backyard. Additional highlights include an attached two-car garage with direct entry, generator hookup, on-demand hot water, and an unfinished walk-out basement offering abundant storage or outstanding potential for future finished living space. Whether you're looking for newer construction, modern finishes, flexible living space, low-maintenance ownership, or a convenient location close to both everyday amenities and Maine's lakes region, 3 Lieutenants Drive offers an exceptional opportunity to enjoy the very best of Windham living.

3 Lieutenants Dr, Windham

Listing courtesy of Meservier & Associates.

14 Emerson Dr, Windham
$399,900
4 Beds ⋅ 2 Baths
Your Maine waterfront opportunity is knocking. This 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage was just pulled from Auction and has been reduced. Boasting a Single Family home with attached apartment and over 3,000 square feet of previous finished space the possibilities are endless. Images in this listing have been virtually staged.

14 Emerson Dr, Windham

Listing courtesy of Excellence Realty.

7 Hall Rd, Windham
$485,000
3 Beds ⋅ 2 Baths
Welcome to this private and tucked-away retreat, gracefully situated on 1.29 acres of peaceful countryside. Offering 3 spacious bedrooms, 1.5 bathrooms, and a 1-car garage, this inviting home blends comfort, efficiency, privacy, and convenience in a setting that feels wonderfully removed while still keeping everyday amenities close at hand. Freshly painted and thoughtfully maintained, the home offers a clean, welcoming feel throughout, along with energy-efficient heating and cooling designed to provide year-round comfort. Outside, a new shed adds valuable storage, while a dedicated garden area offers the perfect opportunity to grow flowers, vegetables, or create the outdoor space you've been envisioning. An existing chicken coop is also ready for its next flock, making it easy to embrace a simple and rewarding homestead lifestyle. One of the property's most appealing features is the freedom it offers. Tucked away in a peaceful rural setting, the home is not located within a subdivision governed by restrictive bylaws and carries no association fees, allowing you to enjoy your property with greater flexibility and independence. Despite its private setting, the location remains remarkably convenient. Public beaches, boat launches, shopping centers, local restaurants, and everyday necessities are all just a short drive away, while Portland is approximately 25 minutes from your doorstep. Whether your days are spent enjoying the water, tending a garden, gathering fresh eggs in the morning, relaxing in the privacy of your own backyard, or simply appreciating a home that offers both comfort and freedom, this exceptional property presents a wonderful opportunity to enjoy the best of Maine living.

7 Hall Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

305 Windham Center Rd, Windham
$599,900
3 Beds ⋅ 3 Baths
*Back on the market - no fault of seller or property* This is your opportunity to enjoy and reap the rewards of this charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 bedroom, 1 bath In-Law apartment attached. Huge barn, w/work space/pottery studio, beautifully landscaped, pastoral 3.3 acre lot with gardens, flowers, blueberries, veggies and mature trees offered for the first time in 31 years. This classic home with modern accommodations has integrity and flexibility, it's just waiting for your design. Thoughtful and practical updates and upgrades made throughout the ownership. Lovingly maintained and enjoyed. Enchanting spaces inside and out. The farmhouse boasts a large, eat-in kitchen with a pantry and laundry room adjacent. Beautiful antique cast iron stove. Formal dining room and a 1st floor bedroom with a sizable dressing room/closet. Large, newer French doors lead to a sweet side deck overlooking green trees and fields. New roof on the main home 2024 as well as a heat pump for heating and cooling in 2023. The expansive mudroom separates the In-Law apartment from the farmhouse. In-Law apartment with its own deck was added in 1995. Perfect for personal, family use or for additional income. New roof on the apartment 2023, heat pump in apartment installed 2025. The barn and the back woodstock was used as the owner's pottery studio and wood fired kiln. A stunning piece of structural history, with tons of storage and space for your passions or practical uses. This truly special property offers a solid, warm and practical home on positively cinematic farm land. Tucked away from the hustle and bustle but only minutes away from walking trails and Windham Center for shopping, services, entertainment and dining. Less than 15 minutes to the Maine Turnpike, less than 30 minutes to Portland. Make this historic gem your own bucolic, rural paradise.

305 Windham Center Rd, Windham

Listing courtesy of Portside Real Estate Group.

21 Land Of Nod Rd, Windham
$699,000
3 Beds ⋅ 3 Baths
We call it 'The Tree House'--a ranch built bigger and bolder. Set on nearly 10 private acres, this beautifully renovated home is wide, solid, and built to impress: hardwood floors, solid wood doors, statement glass hardware, a true primary suite, and a kitchen with a gas range made for real cooking. This multi-level layout offers a finished lower level, which adds a bonus room and kitchenette, guest suite, in-law space, studio, or office--the choice is yours. Out front, a pollinator garden brings monarch butterflies all summer long. A heated barn rounds things out with its own oil tank, a pro-grade Kellogg air compressor, pull-down loft storage, and a serious workspace. Minutes from Windham Center, area lakes, and an easy Portland commute--with potential for two additional buildable lots behind the home (subject to municipal approval). A transformation, inside and out.

21 Land Of Nod Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

15 Sleepy Hollow Rd, Windham
$4,200,000
7 Beds ⋅ 5 Baths
This is a rare opportunity to experience luxury lakefront living in this extraordinary, furnished waterfront residence on pristine Sebago Lake. Take in spectacular Mt. Washington views, breathtaking sunsets, abundant natural light and 113 feet of private shoreline.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. Multiple premier ski destinations are within an easy drive making this a true four season gem. Share what you will come to love about the Lakes Region with friends and family. Two attached guest suites/apartments seamlessly expand the home's living space for larger gatherings. Each has its own entrance and parking.The main level features a great room, an expansive kitchen, large island with seating for 6, a private office or formal dining room, and a luxurious primary suite complete with a walk-in closet and laundry. The spa-inspired ensuite bath includes a spacious steam shower with dual shower heads and jetted soaking tub. The fully finished walk-out lower level expands the home's possibilities with a dedicated media/theater room, an additional family room with kitchenette, bedroom and full bath--ideal for guests or extended family. Upstairs, you'll find another comfortable living area, two large bedrooms, a full bath, and an expansive deck where you can relax while enjoying panoramic views.Situated on 2.1 acres, the property features mature landscaping with fruit trees, an expansive lawn, playground, outdoor speakers, and a spacious patio with a fire pit--perfect for entertaining family and friends. Exceptional waterfront amenities include a permanent lakeside deck with seating, storage, and direct swimming access. The deep-water dock features a generous 12 x 20 ft seating area, Jet Ski lift, storage for lake toys, and a boat mooring with room for additional moorings.

15 Sleepy Hollow Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

104 Harvest Hill Rd, Windham
$520,000
3 Beds ⋅ 2 Baths
Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concept with 9' high ceilings. Recent updates include all new windows and doors, flooring on 1st level and 2nd floor hallway and a Vermont Casting woodstove for an additional source of heat. Enjoy the seasonal views of the Western Mountains and amazing sunsets from your front windows or sitting outside in your Adirondack chairs sipping your morning coffee. You will understand why its named, ''Harvest'' Hill Rd on this natural piece of property with the likes of strawberries, blackberries, blueberries, witch hazel and mint! Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is 5 minutes to both Little Sebago Lake and Big Sebago Lake boat launches and a quick walk or bike ride to the private beachfront of Tassel Top on Sebago Lake. The shops and grocery stores are 7 minutes away as well as minutes from Chipman's Farm Stand and Good Life Market! You are nestled away, yet 20 minutes from the Maine Turnpike, 30 minutes to downtown Portland (South) and 45 min - 1 hr (North) from Pleasant Mountain and Sunday River Ski Resort. Don't miss out on this little piece of heaven and check it out with a private tour today! Seller is willing to give concessions to Buyer at closing.

104 Harvest Hill Rd, Windham

Listing courtesy of www.HomeZu.com. 877-249-5478
22 Montgomery Rd, Windham
$499,900
2 Beds ⋅ 2 Baths
4.67 ACRES ON COLLEY WRIGHT BROOK — YEAR-ROUND WATER, YOUR OWN PRIVATE WATERFALLS, AND A POTENTIAL BUILDABLE LOT. The entire property conveys: all 4.67 acres, over 300 feet of owned water frontage, and a true Maine homestead just 30 minutes to Portland. Potential second building lot — buyer to confirm with the Town of Windham. Some properties you tour. This one you fall for. Set on 4.67 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 at one of two brookside fire pits, wander the gardens, or simply listen to the water from a porch tucked among mature trees. The 1969 log home is full of soul, built from logs harvested right up the road at Staples Farm. Inside, a cathedral-ceilinged living room is anchored by a grand wood-burning fireplace, while a heated three-season sunroom with radiant floors brings the woods-and-water views indoors all year. Enjoy easy one-floor living with two bedrooms and two full baths, plus a finished office/bonus room on the lower level for work, hobbies, or guests. For the self-sufficient at heart, this is a dream: an outdoor wood boiler can heat the entire home — with soft or hard wood you harvest right from your own land — backed by baseboard hot-water heat, a basement wood stove, and the sunroom's radiant floors. Heat your way, all year long. And the grounds are a love letter to the seasons: established perennial and raised-bed gardens, lilacs and dahlias, tulips and lilies, plus a true edible landscape — apple trees, elderberries, serviceberries, rhubarb, blueberries, strawberry patches, and a full herb garden of chives, oregano, sage, and thyme. Private, peaceful, incredibly scenic — yet only about 30 minutes to Portland. Come stand by the brook and listen. You'll understand.

22 Montgomery Rd, Windham

Listing courtesy of Dream Home Realty LLC.

Hall Rd, Windham
$749,900
Build your dream home--or explore the potential for future development--on this exceptional 8.85-acre parcel in desirable Windham. Situated on a paved, town-maintained side street, this expansive property offers a rare combination of privacy, convenience, and natural beauty. With over 400 feet of owned frontage along the scenic Pleasant River, you'll enjoy a picturesque setting perfect for relaxing and enjoying the outdoors. Conveniently located near local schools, popular running and walking trails, shopping, and some of the area's favorite restaurants, this property offers easy access to all that Windham has to offer. The generous acreage may offer subdivision potential, subject to town approvals and applicable ordinances, making it an attractive opportunity for builders, investors, or those looking to create a family compound. Whether you're envisioning a private waterfront retreat or considering future development possibilities, this unique property is full of potential.

Hall Rd, Windham

Listing courtesy of Dream Home Realty LLC.

8 Beaulieu Dr, Windham
$79,800
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

8 Beaulieu Dr, Windham

Listing courtesy of Maine Values Real Estate.

Tavern Hl, Windham
$445,000
Large 9.4 +/-acre tract with 908' frontage meets the dimensional standards for up to four lots, each requiring minimum 200' frontage and 1.84 acres. Great opportunity for a home builder to construct several homes or a buyer to build his/her home and split off the remainder for multiple lots. Tavern Hill is a private road with a homeowners association. A nearly six acre lot with 200' frontage in Tavern Hill sold this spring.

Tavern Hl, Windham

Listing courtesy of EXP Realty.

40 Highland Cliff Rd, Windham
$169,500
Back line on a small trout brook with trees, most of the lot is beautiful fields. Nice level loamy lot.

40 Highland Cliff Rd, Windham

Listing courtesy of Butts Commercial Brokers.

Cook Rd, Windham
$275,000
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 peace & serenity of rural living, but views of the most breathtaking long sunsets, making it the ideal place to call 'home'. With soil tests, surveys, septic/ house plans & delineations now completed & driveways almost in - Summer in sweet Lakes Region awaits! Driveway for Lot to come off driveway of 37 Cook Rd./not accessible via the private property dirt road located after the stop sign/mailboxes at the end of the paved portion of Cook Road

Cook Rd, Windham

Listing courtesy of Keller Williams Realty.

6 Dolley Farm Rd Unit 3, Windham
$479,000
3 Beds ⋅ 3 Baths
Come see why so many have chosen Dolley Farm Condominiums for their new home! 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 and living areas, while a rear patio extends your living space outdoors. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

30, 32, 34 Roosevelt, Windham
$1,800,000
Developable site. Three lots totaling over 16 acres, being sold together, on highly traveled Roosevelt Trail (Route 302). This prime location offers excellent visibility and accessibility just minutes from the Lakes Regionâ€'ideal for capturing both local and seasonal traffic. Zoned C-3, the land allows for a wide range of light commercial and mixed-use development including retail, office, contractor services, and residential options. Mostly level with strong road frontage, this is a rare opportunity to invest in a high-growth area with flexibility and scale.

30, 32, 34 Roosevelt, Windham

Listing courtesy of Keller Williams Realty.

25 Daybreak Ln Unit 8, Windham
$699,000
2 Beds ⋅ 3 Baths
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 for stacked or side-by-side laundry on one or both floors of living. This inner unit features two full baths, a functionality first open concept kitchen, a front porch and back deck for sipping in the scenic surrounds, 18ft cathedral ceilings, and not one but two bonus spaces, fit for an office, spare bed, hobbying, or entertaining! This unit also has the option to finish its full-daylight walkout basement for an additional 500 SF of living area. Community Amenities to Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the over 50 acre parcel with over 6000 feet of nature trails, more than 500 feet of manicured lake front to carry in kayaks, canoes and paddleboards, plus a community maintained dock. Located just 10 miles from downtown Portland, residents will enjoy unbeatable proximity to top rated health care and hospitals, as well as Maine's finest dining and entertainment options. Boating, skiing, golf, shopping, dining, sports & activity clubs... The way 55+ life should be, and you can have it all in The Cove at Highland Lake! Reserve now & for a limited time you may customize your home's finishes!

25 Daybreak Ln Unit 8, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com
14 Heathwood Dr, Windham
$525,000
The business currently at the location is not for sale, just the building and the grounds. The current tenant has a lease expiring on 7-1-2027 which will be transferred to the new owner. The monthly lease payment is $2500, triple net. Situated in a high traffic area with unmatched visibility. Make this location the home for your new business or franchise.

14 Heathwood Dr, Windham

Listing courtesy of Big Bear Real Estate Company.

20 Freeman Ct, Windham
$1,375,000
4 Beds ⋅ 3 Baths
Sebago Lake Lifestyle with 700' of gated private beach frontage and an exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, new roof, 5 bay garage & exclusive access to Maine's premier Sebago Lake - 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 bedrooms including a primary bedroom suite of over 1,000 sq ft gross living area, 2.5 baths, a 5-bay garage, set on over 2 acres providing privacy in every direction. The first-floor renovation creates an open-concept layout designed for effortless entertaining and everyday living. A stunning custom kitchen appointed with premium fixtures, Calacatta Brazil true white quartzite paired with contrasting black quartzite countertops, and waterfall-edge detailing that creates a sleek modern look. New flooring, recessed lighting, and an integrated sound system elevate the entire main living area. Additional recent improvements include a new 7,000+ sq ft roof, remodeled and updated baths, 15-zone irrigation system, new hot water heater, and a freshly resealed driveway. Multiple outdoor living spaces include a raised stone porch seating area, a large porch with a wooden trellis which is directly accessed from the first floor of the home, and a charming foot bridge overlooking a cascading stone fountain. A perfect way to let the world fade away as you relax in your own private backyard oasis after a day on the lake. Windemere Estates residents enjoy private Sebago Lake frontage with three beach areas, tennis courts, beach volleyball, gazebo, private boat launch, and a residents-only dock (boat slips available by tenure). Additionally, this estate is among a select few in the community to include its own mooring. Privacy, modern sophistication, and Maine lake living all come together at this must-see property. Shown by appointment only.

20 Freeman Ct, Windham

Listing courtesy of Holt Realty.

3-4 Mallison Falls Rd, Windham
$3,750,000

3-4 Mallison Falls Rd, Windham

Listing courtesy of Keller Williams Realty.

26 Dolley Farm Rd Unit 12, Windham
$479,000
3 Beds ⋅ 3 Baths
Move in Ready! Come see why so many have chosen Dolley Farm Condominiums for their new home! The Sunrise 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 and living areas, while a rear patio extends your living space outdoors. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

26 Dolley Farm Rd Unit 12, Windham

Listing courtesy of The Flaherty Group.

Lot #10 Goose Pond, Windham
$998,900
Discover a rare opportunity to own 35.97± acres of private, wooded land ideally positioned near the Windham, Falmouth, and Cumberland lines. Tucked into one of Southern Maine's most desirable and rapidly growing areas, this unique parcel offers exceptional privacy, natural beauty, and proximity to Portland, I-95, and surrounding higher-end communities. The land features mature woods, natural stream corridors, existing trails, and a peaceful setting surrounded by conservation land and outdoor recreation opportunities. A 10-acre town-owned parcel located within the surrounding boundaries creates a unique natural buffer and enhances the sense of privacy and seclusion. This property may appeal to buyers seeking a private estate setting, recreational retreat, long-term land investment, or future strategic opportunity. Survey recently completed reflecting 35.97± acres. Access is currently under review and buyers are encouraged to perform their own due diligence regarding access rights, insurability, intended use, development potential, and municipal approvals. Shown by appointment only.

Lot #10 Goose Pond, Windham

Listing courtesy of Keller Williams Realty.

Lot 10 Enterprise, Windham
$450,000
Discover the potential of this 4.59-acre parcel, perfectly situated in an area zoned for enterprise development—offering endless possibilities for commercial, industrial, or mixed-use projects. This prime location provides excellent accessibility and visibility, ideal for future growth. The lot is cleared and ready for your vision. Don't miss this chance to create something extraordinary in a thriving area!

Lot 10 Enterprise, Windham

Listing courtesy of A Team Realty.

30 Marshall Valley Rd, Windham
$125,000
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 just raw land. This Lot is a Must See!!

30 Marshall Valley Rd, Windham

Listing courtesy of Getty Real Estate Services, LLC.

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