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

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

Welcome to the final opportunity to own a brand-new home in Edgewood Estates, one of Windham's most sought-after communities. More than a neighborhood, Edgewood Estates is a thoughtfully crafted enclave where timeless architecture, generous homesites, and Maine's natural beauty come together to create a place where life's next chapter begins. One of the most exceptional advantages of purchasing during the construction process is the opportunity to work alongside your own dedicated Design and Construction Liaison. Rather than simply selecting from a standard list of finishes, you'll have the ability to thoughtfully personalize your home to reflect your vision, style, and the way you live. From design selections and scheduling to ongoing communication and coordination, your Design and Construction Liaison serves as your trusted guide throughout the building journey, creating a seamless, organized, and enjoyable experience from contract to completion. Crafted with an unwavering commitment

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

If you've been searching for a true, easy-living Maine camp feel with modern comfort, you've found it! 12 Getaway Road in Windham checks every box. Nestled right on the quiet Little Duck Pond, this charming, updated cottage offers peaceful waterfront living with the unbeatable convenience of an easy-access Windham location. Inside, the fresh space centers around the amazing views and a beautiful stone fireplace. This cottage has been beautifully updated with a new kitchen, bath, flooring and pine shiplap throughout. Enjoy this private, quaint cottage on a clean 35 +/- acre pond that is home to largemouth bass, perch, pickerel, etc. Kayak, paddle, swim or launch your motorized boat right from your front yard

A rare Highland Lake offering-a newly built, turnkey 4-bedroom waterfront home with 3 full baths and beautiful lake views. Open the door and begin your year-round vacation. Enjoy exceptional energy efficiency/performance for stress-free living, along with a solar system and low-maintenance exterior. Skylights, tongue and groove pine accents and exposed beams add character to the interior. The lake becomes part of everyday life, whether you're cooking breakfast, reading on the covered porch, or waking up to the sparkle of the water from your bedroom. In summer, relax on the deck or head out for a swim, paddle, or boat ride. In winter, cozy up by the wood stove or go ice fishing. A gradual sandy entry leads to 43 feet of privately owned waterfront with space for a dock and boat, plus an additional 40 feet of shared sandy waterfront access-all just 15 minutes from Portland

Large ranch with so much to provide. Over 3200 sq ft of finished living space. Kitchen is open to the living room and dining area, great layout for entertaining. Kitchen Includes new cabinets, granite countertop and appliances. New plumbing fixtures, cabinet and countertop in the first floor bathroom with laundry shoot. Epoxy floor recently installed in basement. Massive 780 sq ft primary suite features jetted tub, separate shower and 2 large walk-in closets. Large laundry room with wrap-around work counter. Relax and enjoy your favorite drink in the comfort of the screened porch. Two large rock walls enhance the beauty of this property located only a few minutes to North Windham's business district. This property sits on nearly 2 acres, plenty of room to savor the outdoors. For those with an entrepreneurial spirit, you can set up your business in the basement with your advertising sign on Rte 302. Property is located in Windham's C-3 zoning (see town ordinance for the types of busines

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

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!

Welcome to 513 Falmouth Rd in Windham, Maine! Move-in ready and freshly refreshed, this 3-bedroom home offers comfort, space, and plenty of storage for today's lifestyle. The interior features fresh new paint, giving the home a clean and inviting feel. Recent updates include new flooring in the primary bedroom, common bathroom, and basement. Outside, enjoy a large, fenced-in backyard with plenty of room for entertaining, gardening, recreation, or simply relaxing. A shed provides additional storage for outdoor equipment and tools. For those needing extra parking, storage, or workspace, this property offers an attached 2-car garage plus a detached 2-car garage, providing an impressive amount of space for vehicles, hobbies, equipment, or a workshop. Located in desirable Windham, this property combines recent updates, generous outdoor space, and exceptional garage capacity. Whether you're a first-time buyer, growing household, or simply looking for a home with room for vehicles and project

Welcome to this beautifully maintained and inviting two-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 bl

A rare Highland Lake offering-a newly built, turnkey 4-bedroom waterfront home with 3 full baths and beautiful lake views. Open the door and begin your year-round vacation. Enjoy exceptional energy efficiency/performance for stress-free living, along with a solar system and low-maintenance exterior. Skylights, tongue and groove pine accents and exposed beams add character to the interior. The lake becomes part of everyday life, whether you're cooking breakfast, reading on the covered porch, or waking up to the sparkle of the water from your bedroom. In summer, relax on the deck or head out for a swim, paddle, or boat ride. In winter, cozy up by the wood stove or go ice fishing. A gradual sandy entry leads to 43 feet of privately owned waterfront with space for a dock and boat, plus an additional 40 feet of shared sandy waterfront access-all just 15 minutes from Portland

Video Tour: Brand New Home with ROW access to Highland Lake! Experience Maine living in this move-in-ready custom home set on.47 acres. Offering 1,664 sq. ft 3 bedrooms, and 2.5 baths. The thoughtfully designed floor plan features a first-floor primary suite with walk-in closet and en-suite bath with tiled shower. The beautifully appointed kitchen showcases an oversized island with quartz countertops, while first-floor laundry adds everyday convenience. All three Bedrooms have walk-in closets for plenty of storage. Step outside to an extra-large deck, perfect for entertaining, summer gatherings, and relaxing while enjoying the Maine outdoors. Modern craftsmanship, refined finishes, and easy access to Highland Lake create the perfect setting for elevated four-season lake living. Taxes shown are land only, TBD, call town of Windham. *Directions are tricky with GPS- Be sure to come down Albion Rd to Swan Rd, Vista Dr, to Birdsong- other routes will take you on rough roads *Be sure to see

Beautifully maintained and full of character, this inviting log sided home offers the quintessential Maine lakefront lifestyle on the shores of Little Sebago Lake. The home features three bedrooms and one and a half baths with a warm and welcoming open-concept kitchen/dining area that flows into a living room anchored by an impressive double-sided fireplace. Hardwood flooring throughout many of the rooms add to the home's timeless appeal. Upstairs, you'll find three generous bedrooms, including a primary with its own private screened-in porcha€”a peaceful place to enjoy your morning coffee while taking in the sights and sounds of the lake. A spacious family room with cathedral ceilings provides additional room to gather, relax, or accommodate guests. Just off the family room, a cozy nook offers the perfect spot for a home office, study, or quiet reading retreat. Beautiful wood detailing in the soaring upstairs ceilings enhances the warmth and craftsmanship of this special home. An atta

Set near the end of a quiet cul-de-sac, 23 Tate Lane offers approximately 2,400 square feet of flexible living space on 1.16 acres in a remarkably convenient Windham location. The Cape-style home features four bedrooms, two full baths and an attached two-car garage with direct entry. Inside, the sunny eat-in kitchen connects naturally with comfortable living and dining spaces. One of the home's standout features is the expansive, light-filled bonus room above the garage-ideal as a family room, game room, home office, fitness space or guest area. First-floor laundry, a newer heating system and a full unfinished basement with abundant storage add everyday practicality. Outside, a spacious composite deck overlooks the large, open backyard, where a seasonal stream and small bridge add character to the setting. There is plenty of room to entertain, garden, play or simply relax and enjoy the view. Located nearly across the street from Windham High School and its athletic fields, the property

Welcome to this beautifully maintained Colonial nestled in a family-friendly neighborhood! From the moment you arrive, you'll appreciate the inviting curb appeal, well-landscaped grounds, freshly painted exterior, Trex front porch, and stamped concrete walkway. The open-concept main level offers an ideal layout for everyday living and entertaining. The living room features a cozy fireplace and flows seamlessly into the dining area and spacious kitchen, complete with plenty of workspace. A charming coffee bar adds an extra touch of convenience. The large mudroom provides excellent storage and space. Upstairs, the primary suite offers hardwood flooring and a private bath, while additional bedrooms provide plenty of space for family and guests. The finished room over the garage can be used to suit your needs. Step outside to enjoy the newer deck, overlooking a wonderfully private backyard-perfect for relaxing, entertaining, or enjoying your morning coffee. Thoughtfully cared for and move-

Charming 2-bedroom ranch situated on a quiet cul-de-sac in a desirable North Windham neighborhood. The spacious first-floor layout features two bedrooms, including an oversized primary bedroom, a bright living room, kitchen, and full bath. The finished basement provides additional flexible space for a family room, office, playroom, or guest area. The home features numerous updates, including the roof, furnace, oil tank, siding, windows, doors, insulation, plumbing, electrical, and garage door. Enjoy a large fenced-in yard, deck, porch, paved driveway, attached garage, and convenient access to nearby recreational water and area amenities. Public water and private sewer

Welcome to 513 Falmouth Rd in Windham, Maine! Move-in ready and freshly refreshed, this 3-bedroom home offers comfort, space, and plenty of storage for today's lifestyle. The interior features fresh new paint, giving the home a clean and inviting feel. Recent updates include new flooring in the primary bedroom, common bathroom, and basement. Outside, enjoy a large, fenced-in backyard with plenty of room for entertaining, gardening, recreation, or simply relaxing. A shed provides additional storage for outdoor equipment and tools. For those needing extra parking, storage, or workspace, this property offers an attached 2-car garage plus a detached 2-car garage, providing an impressive amount of space for vehicles, hobbies, equipment, or a workshop. Located in desirable Windham, this property combines recent updates, generous outdoor space, and exceptional garage capacity. Whether you're a first-time buyer, growing household, or simply looking for a home with room for vehicles and project

Spacious, private, and beautifully updated, this unique home offers the perfect blend of character, comfort, and convenience. Located just 15 minutes from Portland and approximately one mile from Windham schools, the property is tucked into a thoughtfully landscaped setting with plenty of space for gardening, entertaining on the patio, and enjoying the yard. The home's passive solar design, vaulted ceilings, exposed beams, and abundant natural light create a warm and inviting atmosphere. The recently updated kitchen, new flooring, and new heat pumps add modern comfort while complementing the home's distinctive architectural character. The remodeled primary suite is a true retreat, featuring a kitchenette, stacking washer/dryer, full bath, spacious walk-in closet, and private porch. A first-floor office offers flexibility and could easily serve as a bedroom, depending on your needs. Well cared for and with many updates, this special property offers privacy and space while keeping you cl

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!

Video Tour: Brand New Home with ROW access to Highland Lake! Experience Maine living in this move-in-ready custom home set on.47 acres. Offering 1,664 sq. ft 3 bedrooms, and 2.5 baths. The thoughtfully designed floor plan features a first-floor primary suite with walk-in closet and en-suite bath with tiled shower. The beautifully appointed kitchen showcases an oversized island with quartz countertops, while first-floor laundry adds everyday convenience. All three Bedrooms have walk-in closets for plenty of storage. Step outside to an extra-large deck, perfect for entertaining, summer gatherings, and relaxing while enjoying the Maine outdoors. Modern craftsmanship, refined finishes, and easy access to Highland Lake create the perfect setting for elevated four-season lake living. Taxes shown are land only, TBD, call town of Windham. *Directions are tricky with GPS- Be sure to come down Albion Rd to Swan Rd, Vista Dr, to Birdsong- other routes will take you on rough roads *Be sure to see

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, and 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 finishes and quality craftsmanship throughout. Step inside to discover hardwood flooring, abundant storage, and inviting spaces designed for both entertaining and everyday living. At the heart of the home is an entertainer's dream kitchen featuring beautiful stone countertops, a stylish tile backsplash, ample prep space, and seamless flow into a generously sized dining area perfect for hosting dinner parties or casual evenings with family and friends. The warm and inviting living room is anchored by a gas fireplace, creating the perfect atmosphere year-round. Upstairs, the home continues to imp

Perfectly positioned near both downtown Windham and Portland, this beautifully maintained 3+ bedroom Colonial offers the ideal blend of comfort, space, and privacy. Set on a picturesque wooded lot, the property provides plenty of room to gather, relax, entertain, and enjoy the outdoors, with thoughtful updates throughout adding convenience and comfort. A welcoming front porch sets the stage as you step inside to a warm and inviting living room featuring a cozy fireplace and one of the home's five heat pumps, providing efficient air conditioning and supplemental warmth when needed. Additional heat pumps are thoughtfully located throughout the home. The comfortable kitchen, complete with granite countertops, is ideal for both everyday cooking and entertaining, while the adjacent dining area provides the perfect setting to share a meal or celebrate with good company. Upstairs, the spacious primary suite is a peaceful retreat with an en-suite bathroom and walk-in closet. Two additional bed

Full of classic New England charm, this 3-bedroom home offers generous living space and a flexible floor plan on a.46 acre corner lot. The updated kitchen features a large center island, new appliances, ample cabinet space, and an inviting layout for everyday living. Original hardwood floors, fireplaces, built-ins, exposed beams, and other period details add warmth and character throughout. Recent improvements include all new windows, updated electrical, freshly paved driveway and new leach field, providing peace of mind while preserving the home's historic appeal. Multiple living and dining areas provide room to gather, work, or relax, and the attached two-car garage adds everyday convenience. Located close to shopping, restaurants, and outdoor recreation, this home offers the space, character, and flexibility to suit a variety of lifestyles

Access to Highland Lake sets the stage for the lifestyle you've been looking for at 27 Beach Road in Windham. Tucked away on a dead-end street, (with the sweetest path over a creek to the Lake) this move-in-ready home offers the perfect opportunity to enjoy lake life without the upkeep of direct waterfront ownership. Spend summer days swimming, paddling, fishing, or simply relaxing by the water, then come home to a wonderful backyard with plenty of room to gather, garden, play, or unwind. The setting offers a welcome sense of retreat while keeping you close to Windham's restaurants, shopping, recreation (Lowell Preserve is just at the end of the road near fire station), and everyday conveniences. Comfortable and ready to enjoy from day one, the property offers wonderful versatility as a year-round residence, Maine getaway, or potential rental investment. Whether you're looking for a place to call home or an opportunity to enjoy everything the Lakes Region has to offer, 27 Beach Road de