229 properties for sale in South Windham, Windham town Cumberland County Maine

Welcome to 51 Gambo Road in Windham, where peaceful waterfront living meets everyday convenience. Set along 144 feet of privately owned Presumpscot River frontage, this unique property offers a rare opportunity to enjoy nature right outside your door while remaining close to shopping, dining, walking trails, golf, beaches, fishing, kayaking, and canoeing. This 3 bedroom 2 bathroom home offers over 2400 total square feet and has seen numerous thoughtful renovations, including a newly renovated kitchen, bathroom, and basement. Enjoy your mornings on the screened-in front porch, then spend your afternoons by the river before unwinding in the hot tub or sauna. An outdoor patio and fire pit create the perfect setting for evenings with friends and family. Private riverfront, modern updates, endless recreation, and unmatched tranquility. Come experience 51 Gambo Road, and discover a home that feels like a getaway, without giving up the convenience of being close to most everything!

Historic circa-1900 farmhouse on 4 acres of fields and forest in a desirable rural Windham location, adjacent to Bumbleroot Organic Farm and minutes to Westbrook and Gorham. Filled with vintage character and potential, the home features abundant custom cabinetry in the kitchen, dining, and office spaces; a separate bedroom suite with soaking tub and walk-in closet; and a sunroom overlooking a fenced garden, open field, and woods. A 1,200-square-foot post-and-beam barn provides outstanding possibilities for a workshop, studio, storage, animals, or hobby use. A rare chance to restore, reimagine, and make this remarkable property your own

Welcome to Windham Hill Woods, a well-established and desirable condominium community offering an exceptional combination of convenience, amenities and value. Ideally located on the south side of downtown Windham, this townhouse-style condo provides easy access to shopping, dining and area amenities while helping you avoid much of the traffic congestion found farther north. Inside, the thoughtfully designed floor plan offers comfortable living across three levels. The first floor features a granite kitchen, inviting living room with hardwood flooring, convenient half bath and a sliding glass door leading to your private deck overlooking the wooded edge. Upstairs, you'll find a spacious primary bedroom, second bedroom and full bathroom. Continue to the third-floor loft, an especially versatile space that works beautifully as a home office, reading area, hobby space or flex room. A full basement provides excellent storage and includes the convenience of an in-unit washer and dryer. The $

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!

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

This brand new Cottonwood Colonial home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a functional mudroom and a great back deck. Upstairs includes a primary suite with walk-in closet, two additional bedrooms, a second full bathroom, and laundry hook-ups. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

This beautiful 3-bedroom, 2.5-bath home will have you celebrating your good luck! Life in this serenely situated Windham neighborhood strikes a perfect balance of comfort, convenience and idyllic charm. Inside, a seamless layout, hardwood floors, lofty ceilings, and mood-boosting natural light await. The kitchen's granite countertops, stainless steel appliances, gas stove, island with storage + seating, and large pantry will inspire every home chef. Open access to the dining area makes for easy chatting while cooking. Beautiful windows and a gas fireplace preside over the living room. A half bath with laundry rounds out the main floor. You'll love retreating to the primary suite upstairs, where peaceful nature views and a private bath create the perfect place to unwind. Two additional second-floor bedrooms and a full bath mean there's room for everyone. Opportunity abounds for entertainment, work, or play in the finished basement. Nature lovers and wildlife watchers will adore this tra

If you've been searching for a prime location and space to entertain, you've found it! Welcome to your own backyard oasis in one of Windham's most desirable areas. Designed for hosting and everyday living, this 3-bedroom, 2-bathroom home features an above ground pool, hot tub, tiki bar, and expansive outdoor space ready for gatherings all year long. The large concrete pad currently used for grilling, is easily converted to a basketball court providing plenty of room for recreation. A second outbuilding has been transformed into an insulated, heated home gym giving you a dedicated workout space just steps from the house. Inside, you'll find floor to ceiling updates including a large kitchen, oversized living room with sliding glass doors to the backyard, spacious bedrooms, and the private primary bedroom with en-suite bath. The finished lower level adds even more living and entertainment space with your own movie theater, and two bonus rooms currently used for air hockey and poker night

Welcome to 1 Morgan Ln, a charming 3-bedroom, 2-bath home set on nearly 2 private acres in Windham. The home is thoughtfully laid out for convenient first-floor living, offering ease and functionality for everyday life. Enjoy the space and privacy of a generous lot while still being conveniently located for an easy commute to Portland and surrounding areas. A wonderful opportunity to enjoy peaceful living with the convenience of nearby amenities

Welcome to The Cove at Highland Lake! The first of its kind, Gold Cornerstone Award Winning 55+ Lakefront Community nestled on the pristine shores of Highland Lake. The PORTLAND floorplan is the perfect blend of one-level-living with plenty of space for guests and storage. At 1958 SF +/-, this 2 Bedroom 2.5 Bathroom attached condo with generously sized finished basement is an excellent option for those looking to 'rightsize' into retirement. The Portland offers cathedral ceilings in the main living area, primary bedroom with spacious en suite double vanity bathroom and oversized walk-in closet, plus a guest bathroom with main level laundry. With not one but TWO outdoor composite decks, spacious one level is easy to achieve! But if even more space is needed, you'll enjoy an additional bedroom and bathroom in the finished basement boasting 9ft tall ceiling height. With endless custom finish options and upgrades, owners can select natural stone or quartz countertops, soft-close cabinetry,

NEW CONSTRUCTION CONDO NOW AVAILABLE FOR 2026 OCCUPANCY - MUST SEE ONE OF A KIND DEVELOPMENT! Welcome to The Cove at Highland Lake: where low maintenance lake-life meets Portland-proximate convenience! The Freeport floorplan, our largest single level 2 Bed/2 Bath floor plan comes standard with 1340+/- sq ft, a large open concept living area with a spacious kitchen, soft-close cabinetry, Energy Efficient LED Lighting and Appliances. 22 Daybreak features a floor to ceiling Gas Fireplace feature, Upgraded Cafe Appliance Package, Light and Bright Granite and Quartz Countertops, Finished Basement with an additional bed and full bath, and 9Ft ceiling height! Custom tiled showers, spa like bath fixtures, and cathedral ceilings ensure your condo is well appointed and beaming with natural light. 18 x 12 (approximate) Primary Suite with double vanity bath and a walk-in closet. The Freeport also boasts a large front porch and an oversized single stall attached garage with extra room for storage.

129 Forbes Lane is ready for you to check out! Set on nearly half an acre in an established Windham neighborhood, this classic and alluring Cape offers 3 second level bedrooms, and a 1st floor bonus room which was designed as a primary bedroom! 2 full bathrooms that have been recently renovated and updated, and approximately 1,888 square feet of living space. A full bathroom on both the first and second levels provides added convenience and flexibility. Inside, hardwood flooring and a gas fireplace add warmth and character, while the traditional floor plan offers plenty of room to make the home your own. Additional features include a vaulted ceiling sun room with a wood burning stove, attached 3-car garage with overhead storage, partially finished basement space with a laundry room offers great potential, unfinished attic storage, a generous rear deck, large patio, and a storage shed. Enjoy a generous yard and a convenient location near Windham's shops, restaurants, schools, and outdoo

OPEN HOUSE THIS SUNDAY 9/27/26 FROM 11:30 TO 1:00. Don't miss this property with a recent price adjustment. Rarely seen on the market right now, large rooms, attention to details with upgrades AND a standalone condo with a two-car garage and full basement and low monthly fee of $70.00 for common area maintenance and insurance. From the moment you enter, you'll appreciate the bright, open floor plan, quality craftsmanship, and beautiful hardwood flooring that flows throughout both levels of the home. At the heart of the home is an inviting kitchen featuring granite countertops, a spacious center island, stainless steel appliances, and abundant cabinetry-creating the ideal space for everyday living, meal preparation, and entertaining. The kitchen opens into the welcoming living area highlighted by a custom feature wall with a contemporary fireplace, creating stylish space. Exit through the sliding glass doors to a generous deck overlooking a level backyard, offering plenty of room for su

This home sparkles! Immaculate and is ready for it's next owner. Beautiful landscaping, raised bed garden and a private back yard tucked away. in a great neighborhood on the Windham, Raymond town line. Public water, town maintained road and close to shopping. Five minutes from a Big Sebago beach. Open floorplan and great deck off of dining area. Perfect for summer grilling. Newer heat pump to keep things cool on those warmer days and nights

Stunning 11 y/o colonial on over 4 acres. This 2015 home offers 3 Bedrooms with prime suite offering double walk in closets, beautiful custom tile showing and tons of space. 3 full bathrooms with 1 on the main level and two more on the second floor. Also offering a 1/2 bath in the full finished and walk out basement with 700 more sf high quality finishes. Multiple heating sources include multiple heat pump heads, a pellet stove in the basement, and a viessimann high end boiler. Large eat in kitchen with high end appliances and cabinets plus all solid surface counters. Multiple built in cabinets throughout the first and second floor as wells as high end trip package. The main level offers a large office that can double as a bedroom next to the full bathroom. Now lets talk about outside: A massive back yard large enough to play football and entertain 100 people. A paved driveway large enough for 8-10 cars, A large rear deck that overlooks the private backyard sits above the slider to the

Beautiful contemporary cape with 1st floor primary suite! At the end of a cul-de-sac, in a quiet neighborhood, with the 5-acre community common space along the backside of the property, 14 Abenaki Drive is a peaceful retreat. Everyday conveniences and four-season recreation are close at hand. North Windham's shops, groceries, restaurants, and attractions like Seacoast Adventure are a short drive away, while Dundee Park's river beach, Lippman Park's trails and playground, and the Mountain Division Trail invite easy walks, bikes, and paddles. Sebago Lake and Little Sebago are nearby for swimming and boating, and Portland is only about twenty minutes down the road. North and South travel are at your doorstep! Enjoy small-town Maine charm and city access, gorgeous mornings and star filled nights from the deck off the dining room, or sweet summer days in the private back yard. If you are cozy to home, or delight in travel, this solidly built home will become your paradise. Check out the uni

New Construction Underway Crafted with exceptional attention to detail, this high-performance, Net Zero Ready home offers a rare blend of beauty, comfort, and cutting-edge efficiency. Designed with refined finishes and exceptional attention to detail, the home delivers a quiet, healthy living environment with significantly reduced energy use. Built to Passive House standard principles, it features a superior building envelope with advanced insulation, high-performance windows and doors, and durable, thoughtfully selected exterior materials for long-term beauty and resilience. Energy-efficient systems include Mitsubishi Electric ductless heating and cooling, a high-efficiency air exchanger, and a heat pump water heater. The home is solar-ready and includes a generator hookup for added convenience. Offering approximately 2,200 sq ft of living space, this home includes an 850 sq ft walk-out lower level with plumbing for a future bath, plus an oversized garage with storage above or future

Tucked in South Windham, an area experiencing exciting momentum as part of the town's ongoing Little Falls/South Windham Villages revitalization plan, this classic 1900 New Englander has been freshly painted from top to bottom and is ready to welcome its next chapter. Wood floors carry you through a sun-filled first floor, where the kitchen, dining room, and living room flow together with ease - the living room anchored by a cozy wood stove for those crisp Maine evenings. Upstairs, three bedrooms - including a comfortable primary suite - share a second full bath, while first-floor laundry keeps everyday living simple. With 2 full baths total and thoughtful updates throughout, this home is in truly move-in ready condition. Step outside and the possibilities open up. A level, beautifully landscaped 0.69-acre lot offers a patio and firepit made for gathering, plus a detached 2-car garage for storage and hobbies alike. And for buyers thinking ahead, the property's high-density VC zoning ma

Immaculately maintained and impressively spacious, this oversized ranch offers more than meets the eye. Boasting a footprint of nearly 2800 square feet, the daylight walkout basement with its 9 foot ceilings offers incredible potential to double the home's finished living space, with some framing already in place. Gleaming hardwood floors flow throughout much of the living space, while the thoughtfully designed layout includes an extra large primary bedroom with ensuite, three additional roomy bedrooms, a generous open-concept kitchen and dining area, a spacious living room, and a separate laundry room-providing plenty of space for everyday living and entertaining. Set on nearly two acres along a private dirt road, the property offers a peaceful setting surrounded by nature, while still being conveniently located near Sebago Lake and the North Windham business district with its restaurants, shopping, and amenities. Numerous upgrades and functional improvements add comfort and peace of

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 provides a private spot to relax and take in the surroundings, while the lot offers plenty of room to enjoy the outdoors. Despite its peaceful setting, the home is just a short drive to North Windham for shopping and everyday errands, with Portland also within easy reach

~ OPEN HOUSE SUNDAY ~ 8/23/26! 10:30-12pm ~ 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 entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites-one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations off

Space, privacy, and exceptional versatility come together in this beautifully maintained, one-owner Colonial. Built in 2006 and set on 1.17 wooded acres, this move-in-ready home offers four bedrooms, 2A½ baths, a bonus room, hardwood flooring, and thoughtful features for comfortable Maine living. The main level features a welcoming kitchen that flows into the dining room and a cozy den warmed by a pellet stove. A separate living room provides additional space for entertaining, relaxing, or gathering with family and friends. Upstairs, the spacious primary suite includes a private full bath. Three additional bedrooms and a versatile bonus room provide plenty of flexibility for a home office, playroom, hobby space, or guest accommodations. The attached two-car garage offers direct entry to the main level, along with the added convenience of separate access to the second floor. Practical year-round features include hot-water baseboard heat, two oil tanks, a pellet stove, and a whole-house

Welcome to 8 Port Drive, Unit 8, a well-maintained Windham condo offering a comfortable layout, thoughtful updates, and access to Collins Pond. Tucked into a quiet, secluded setting with little traffic, this home provides a peaceful atmosphere while keeping you close to the shops, restaurants, and conveniences of downtown North Windham. The main level offers the ease of single-floor living, with inviting living spaces and a kitchen enhanced by an updated backsplash and shelving. Fresh paint on walls and doors, updated lever-style door handles, new blinds and curtains throughout, and two new storm doors add to the move-in-ready feel. Upstairs, a flexible bonus room provides additional space for a den, workout room, home office, or other needs. Outside, enjoy the impressive Trex deck completed in November 2025, a fenced area, and a setting that offers a great extension of the home's living space. Additional improvements include a new roof in 2024, new washer and dryer in 2025, garage doo

Set on a beautifully maintained peninsula in Outlet Cove, 68 Outlet Cove Road presents an exceptional Little Sebago Lake setting with expansive waterfront, a private sandy beach, dock, and sweeping sunset views. The level lawn extends naturally to the shoreline, creating an inviting setting for swimming, boating, entertaining, or quiet mornings by the water. Every element reflects years of thoughtful care. Mature plantings, manicured gardens, stone retaining walls, and extensive hardscaping frame the home and lake views. A spacious paver patio and screened porch provide comfortable outdoor gathering spaces, while the sandy beach and dock make it easy to enjoy the lake throughout the day. Multiple outbuildings and garage spaces provide exceptional storage for boats, recreational equipment, tools, and seasonal belongings, while creating an ideal setting for entertaining. Inside, a sun-filled living room with a fireplace and wall of glass captures dramatic water views and flows into the d

Two Family building situated on a 0.69 acre lot. Sewer to be connected at Towns expense in the near future. Many development options for this site

Seller financing incentive available! With an acceptable offer, seller is willing to contribute up to two points toward a buyer's interest rate buydown. Set on 2.5 acres in a peaceful Windham setting, this three-bedroom, two-full-bath home offers privacy, space, and everyday convenience while remaining close to everything the area has to offer. Built in 2006, the home features a comfortable and functional layout with an open-concept kitchen and dining area flowing into the living room, creating an easy space for everyday living and gathering. A welcoming sitting room provides an additional place to relax, while first-floor laundry adds to the home's practical layout. Outside, there's plenty of space to enjoy the property throughout Maine's seasons. Spend summer days by the pool and cooler evenings relaxing in the hot tub, which conveys with the property. Keep chickens in the existing coop, or take advantage of the additional outbuilding for storage, hobbies, equipment, or projects. Mat

OPEN HOUSE, Saturday 10AM-12PM! Highland Lake doesn't close for the winter. Swim and paddle in July, skate and ice fish in January! At 15 Orchard Rd the lake is yours by deeded right, a short walk down the road. No launch fees, no hunting for parking, no waterfront tax bill. Just a towel, or a sled, and five minutes. The property was originally three lots, so there's room here most homes in this neighborhood don't have a€” garden, play, park the boat, spread out. Inside: hardwood floors and a kitchen freshly updated with new counters, backsplash, sink, and faucet. Woodstoves in both the kitchen and living room, plus a fireplace and multiple heat sources, so Maine winters are something to enjoy rather than endure. A first-floor bedroom keeps daily life easy, and several additional rooms flex into an office, hobby space, or a landing spot for guests. Septic is designed for three bedrooms; town records currently list the property as a 2-bedroom. Out back, a large shed handles storage with

Opportunity meets versatility at 5 Cliff Drive in Windham. Set on a spacious 1.84-acre lot, in The C3 Zone, this property offers more than 2,000 square feet of living space, a flexible floor plan, and is set up with an ADU (check with the town for specifics) with a tenant already in place. The upper level offers generous living spaces and plenty of opportunity for a new owner to make it their own. While ready for some updating and personal touches, the property's layout, setting, and additional spaces provide an excellent foundation for creating something truly special. A standout feature is the walkout lower-level with a kitchenette and its own bathroom and entrance coupled with separation from the main living areas, this space offers tremendous flexibility for future possibilities; multigenerational living, extended-stay guests, or supplemental income. There's even more potential to explore. Above the attached garage is additional unfinished space that may offer an opportunity for fu

BIG SKY VIEWS. FRESH DESIGN. Maine Living at its best! This light filled 3-bed Windham home delivers the space, style, and a setting you have been waiting for. The crisp interior features a striking kitchen with white cabinetry, stainless steel appliances, granite counters, and an open flow into the dining and living areas. Bright bedrooms, modern baths, 1st floor laundry, and warm wood floors make everyday living feel effortless. Full basement offers plenty of storgae space. Spend hours on a welcoming covered porch or rear deck, and take in the peaceful surroundings. Enjoy Highland Lake and Sebago Lake adventures, local trails, dining, and easy access to Portland. Schedule a private tour or join us at one of the Open Houses. Open House 1: Wednesday 9/23@4:30-6pm Open House 2: Sunday 9/27@10-11:30am

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!