PROFESSIONAL PHOTOS COMING SOON A Little Cape with Big Possibilities! Fall in love with this storybook 2-bedroom, 1-bath Cape in the heart of Windham — where small-town charm meets everyday convenience! Just a short stroll to shopping and local eats (yes, coffee runs just got easier!) and only 20 minutes to all the fun and flavor of Portland. Inside, you'll find gleaming hardwood floors, fresh new tile, and a completely new kitchen and bath — no updates needed, just move right in and enjoy! The full basement offers plenty of storage and space to grow, while the unfinished second floor is bursting with potential — think extra bedrooms, another bath, or your dreamy primary suite. Out back, a big sunny yard invites gardens, games, or gatherings, and the detached two-car garage keeps cars and gear cozy year-round. And here's the bonus — this property is located in a commercial zone, opening the door to endless possibilities! Live, work, or create your ideal home-based business right where you are. Close to Windham's many lakes and ponds, this charming Cape offers comfort, flexibility, and opportunity all in one — your Maine dream, with a dash of imagination!
Welcome to 186 Falmouth Rd in Windham Maine, a warm and inviting log cabin that blends rustic charm with everyday convenience. This well maintained two bedroom two bath home offers approximately 1,800 square feet of living space and sits on just under four private acres, providing room to relax while still being close to everything you need. Inside, the natural character of the log construction creates a cozy and welcoming atmosphere throughout. Exposed wood, comfortable living spaces, and a functional layout make this home ideal for everyday living or entertaining. With two full bathrooms and flexible living areas, the home easily adapts to a variety of lifestyles whether you are looking for a primary residence, a getaway, or space to work from home. Outside, the nearly four acre lot offers privacy and opportunity while remaining minutes from hiking trails, lakes, shopping, dining, and major commuter routes. You get the feeling of peaceful country living without giving up convenience. Located in Windham, this property is a great fit for anyone who values outdoor recreation, space, and the timeless appeal of a true Maine log cabin. A rare opportunity in a highly accessible location that offers the best of both worlds.
Nestled in the sought after town of Windham, this charming 1,364 square foot ranch offers the perfect blend of location, comfort, and a peaceful setting. With two spacious bedrooms, 1 bathroom, sizeable kitchen, large windows providing abundant natural light, sunroom, and pellet stove. A new heating system was installed in 2024. This home features a well-designed floor plan ideal for daily living and entertaining. The kitchen overlooks the backyard, offering a sunny spot to enjoy your morning coffee. Inside, you'll find hardwood floors in the living room, a full basement for storage, washer/dryer and a potential 3rd bedroom and or a workshop. This home is secure with a full home alarm and camera security system and two home safes for your valubles. The detached two-car garage boasts plenty of space with a back office. Entertain family and friends with cookouts on your large back deck patio as well roasting marshmellows over the fire pit in your sizable secluded back yard surrounded by trees and an abundance of wildlife. You may even find yourself feeding deer and watching them graze from time to time. Another of many factors that makes this home truly special is its location. Enjoy the convenience of being close to in-town shops, dining, and community events, yet still tucked into a neighborhood that feels calm and welcoming. If you are looking to get-away, you're just: 10 minutes to Sebago Lake for boating, swimming, and summer fun. 15 minutes to Windham's shopping and dining district. 25 minutes to Portland for world-class restaurants, culture, and the Old Port. 45 minutes to skiing at Pleasant Mountain for winter adventure. Whether you're seeking a first home, a right-sized downsize, or a place with room to grow, this property offers the perfect balance of Maine lifestyle and everyday convenience.
Welcome to the Parson Smith Homestead, a historically preserved 1764 home located on 124 acres of hayfields, forest, and river frontage. Formerly a house museum, it is a textbook example of colonial architecture. Featuring an interior finished in stages that depicts 4 distinct architectural periods; Georgian, Federal, Greek Revival, and Victorian. The grand staircase is flanked by formal parlors and the original hearth kitchen. Walking the wide-planked flooring, you step through the generations to sit by the fireplaces that warmed the prominent family who worked the original farm. The attic and basement are equally impressive, displaying hand hewn timbers and arched brickwork. Modern comforts have been added over the years, including the modern kitchen, baths, electrical, and forced hot water boiler. In addition to the carriage house, there is a detached 1810-1820 barn, salvaged from another historic Windham site, it was thoughtfully labeled, disassembled, moved to the property, and lovingly re-erected. The property consists of three open fields, presently managed and hayed by a local dairy farm. At the field's edge, amongst Maple trees tapped for syrup, a local beekeeper is cultivating queens in colorful hive boxes. The forest is held in tree-growth protection. On the river-side of the property, the land stretches down to water frontage on the Presumpscot River and surrounds the historic Smith-Anderson cemetery which is owned by the town of Windham and accessed by deeded easement. Complimenting the existing private trails, the Mountain Division Trail system is slated to expand along the existing railbed. The house is set amongst other grand homes on what is known as Windham's Historic Corridor along River Road, the thoroughfare offering an easy commute to Lakes Region recreation and the nearby cities of Westbrook and Portland. Come visit, explore, and fall in love with your new home!
1840's home with lots of charm. Level lot with lots of fruit trees. Detached shed/barn.Property taxes should be lower because the bill reflects the larger land parcel. This home is a diamond in the rough. investing your elbow grease here should pay dividends.
Home is NOT habitable. Do NOT enter property. Property will NOT qualify for traditional loan types - cash, hard money, and construction loans welcomed. This would be a great place to start new, 3.5 acres in nice Windham neighborhood. Please see MLS #1647089.
Unique opportunity to own this 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage.Boasting a Single Family home with attached apartment and over 3,000 square feet of finished space the possibilities are endless. Property is currently occupied and being sold at auction site with no access. No Trespassing, do not disturb the occupants.
Charming one-level living ranch setback on 2.58 acres with beautiful sunsets from your porch. This spacious 3-4 bedroom home with 2.5-baths was built in 2009 and offers 1456 sq. ft. of main-level living space with hardwood and tile flooring throughout, custom built maple cabinetry with granite countertops and stainless steal appliances. Primary bedroom with full bath and 2 additional bedrooms. You'll enjoy grilling off the private back deck accessible from the glass sliders off the dining area. A washer & dryer room is just off the kitchen. It also includes an additional 1,017 sq. ft. of finished basement currently used as a family entertaining room, gym and guest bedroom with half bath plus just under 500 sq. ft. of storage area. This conveinent location combines private country living with easy access to downtown Windham (2.5 miles) and 11 miles to Portland, along with walking distance to the new Windham middle school. Please call today to schedule a private showing!
Beautiful Big Sebago Lake Sunsets from the comfort of your end unit condo in the sought after Whites Bridge Association. Enjoy access to private sandy beaches, tennis courts, and a boat slip. The condo itself offers wonderful views of the basin. The condo has 2 bedrooms and 2 bathrooms on the second floor. The first floor offers a half bathroom, living room, dining room and kitchen. The daylight basement offers another full bathroom and two more rooms. There is is private patio overlooking the lake also! All this is located minutes from Windham shops and restaurants and a short drive to Portland.
Move in ready at its finest! Set on a private lot, in a great location, this home is ready for new owners. With an efficient layout, this home will be low maintenance for years to come. Schedule your showing today!
This standout Colonial delivers space, light, and modern comfort in a location that keeps everything close. The main level opens into a bright, connected living area centered around a sleek kitchen with a large island, granite counters, and stainless appliances. A gas-fireplace in the living room for added ambiance and direct access to the elevated back deck makes this house perfect for entertaining or relaxing. Upstairs you'll find three well-sized bedrooms, including a primary suite with a tiled shower and generous closet space, plus a convenient second-floor laundry. The walkout basement steals the show with 10-foot ceilings making it a great candidate to finish for added space or even add a golf simulator. The sunny lot, fenced in back yard, and covered front porch round out a home built for everyday ease.
Welcome to 1 Matinicus Way — a charming, low-maintenance single level condo offering comfort, and convenience. This 2-bedroom, 1.5-bath unit features 767 square feet of thoughtfully designed living space, an attached one-car garage, and a bonus enclosed 3-season sunroom perfect for enjoying your morning coffee or unwinding in the evening. The open-concept layout connects the kitchen, dining, and living areas seamlessly, creating a cozy and functional flow for everyday ease. Tucked in a quiet 55+ Windham association just minutes from shopping, dining, trails, and lakes. This condo is a peaceful retreat with quick access to all that the Lakes Region and Greater Portland features. Schedule your showing today and discover the lifestyle this welcoming condo has to offer!
Welcome to 1 Friendly Way — South Windham's newly built, luxury modern-style bungalow located off Land of Nod Road, a quiet street just five minutes from Highland Lake and approximately two miles from the public boat launch on the Falmouth side. This 2,016 sq. ft. floor plan offers a first-floor open concept layout with a gas fireplace and real oak hardwood flooring, along with a beautiful designer kitchen featuring Corian countertops, stained cabinets, quality appliances, and a gas cookstove. The primary suite includes a walk-in closet and a spacious full bath with a custom-tiled shower and laundry area. Just off the living room, a graceful oak staircase with balusters leads to the second floor, where you'll find two spacious bedrooms with oak hardwood floors, walk-in closet, and a full bath with a tub and tiled floor. Additional highlights include abundant closet space, a full walk-out daylight unfinished basement, a gas on-demand water heater, a Viessmann boiler, underground electric, a large deck off the kitchen, and a landscaped entry with a covered front porch. All of this is set on a quiet two-acre lot just minutes from Riding to the Top Farm and under 20 minutes from Portland. GPS use 21 Land of Nod Road (see sign abuts property)
Welcome to Shepherd Lane, Windham's newest subdivision! Located off Falmouth Road, Shepherd Lane is convenient to Portland and all that the Lakes Region has to offer. This under-construction Cottonwood Colonial features 3 Bedrooms, 2.5 Bathrooms, and an open-concept first floor. Upstairs, there are three bedrooms, including a primary bedroom with an ensuite bathroom and a walk-in closet, two guest bedrooms, and a full bathroom. All 13 homes on Shepherd Lane will have city water and will be well-appointed with luxury vinyl flooring and tile on the 1st floor, granite countertops in the kitchen, and full basements. Four plans are available that will meet your budget and needs. HOA dues are an estimate. *All photos may be shown with available upgrades. 22 Acres includes house lots and common space for the subdivision.
Welcome to 22 Turkey Trail, a bright and inviting 2 bed, 1.5 bath townhouse offering comfort, convenience, and a low-maintenance lifestyle. With low association dues of just $300 per month and a well-cared-for community setting, this home is an appealing choice in Windham. Inside, the floor plan feels open and airy, with plenty of natural light and comfortable living areas. Upstairs, the spacious primary bedroom stands out with soaring vaulted ceilings that give the room a truly impressive feel. A tucked-away loft overlooks the space and offers a flexible spot for a home office, reading nook, or creative corner. The second bedroom is nicely sized and adds to the home's easy livability. There is also a large basement that adds valuable bonus space and stays nice and dry, making it an ideal spot for a home gym, hobby area, or additional storage. Recent upgrades add even more desirability, including a pellet stove in the living room, a new refrigerator, dishwasher, and cookstove, a new generator hookup, and new windows in the upstairs bedroom. The community amenities are a true highlight, including an in-ground pool, tennis court, and a basketball court for relaxed outdoor enjoyment just steps from home. There are also lots of walking trails nearby, and this association is dog friendly! The location ties everything together. You are close to Windham's shopping and dining, minutes to Route 302 for an easy commute, and only a short drive from Sebago Lake, the town beach, and countless recreational opportunities. It is a peaceful, convenient place to settle in and enjoy everything the area has to offer. To view a full video walk through tour, head over to YouTube and search for the property address. Thanks for your interest!
Newly completed Windham home is located only minutes to Portland in an established neighborhood with no fees! This beautifully crafted, turnkey Colonial-style home is ready for you to move in and make it your own! Step inside to discover an open and airy main level, featuring a bright, modern kitchen with brand-new stainless steel appliances, and gorgeous granite counters. Enjoy the warmth and efficiency of radiant heat throughout the entire main level with these stunning concrete floors you will fall in love with. The first floor also includes a versatile bonus room with closet, ideal for a home office, or a playroom, along with a full bathroom for added convenience. Upstairs, the spacious primary bedroom suite offers a peaceful retreat with dual vanities, two walk-in closets, and plenty of natural light. Two additional bedrooms share a well-appointed full bathroom, and the second level also features a conveniently located laundry area to make daily chores a breeze. Enjoy your private deck with stairs leading to a huge back yard Ideally located just minutes from the Maine Turnpike and Sebago Lake, this home offers the perfect blend of convenience and tranquility.
Move-in ready and recently remodeled, this low-maintenance Windham split-entry sits on just under a half-acre and offers modern efficiency throughout—all just 25 minutes from Portland and less than an hour to the lakes, beaches, and recreation Southern Maine is known for. Major improvements completed within the last 12 months include new decking, new fencing, exterior doors, new gutters, new garage door system, and a brand-new septic system. Multiple heat pumps provide efficient heating and cooling, complemented by a new heat-pump hot water heater and a heat-pump combo washer/dryer. Inside, enjoy fresh paint, an updated bath, new windows, and a completely redesigned kitchen with stainless steel smart appliances (Samsung Bespoke Line). 4th bedroom option in the lower level with recent addition of egress window (3BR septic). There's truly nothing left to do except move in and enjoy. This Certified Pre-Owned Home has been thoroughly inspected by a professional home inspector, and you'll receive the detailed building inspection at no cost - no surprises here! Plus, enjoy peace of mind with a 12-month Home Warranty and a 12-month Satisfaction Guarantee: Love this home, or we will sell it for you for free! Conditions Apply. A pre-listing title search was performed to confirm clear title. This property is ready to go!
Great Opportunity, Motivated Sellers, In An Amazing Windham Location!! Welcome to 26 Marshall Valley Road. This 2 bedroom, 2 bath split level cape has a ton of charm. The open concept living room with wood wrapped beams, and a wood stove, along with the formal dining room both have spacious cathedral ceilings. Next you go to the well lit kitchen with island and granite tops throughout, that leads you into the very sunny breakfast nook!! The dining room and breakfast nook are joined together by a huge covered wrap around farmers porch, perfect for entertaining and enjoying the country setting. Upstairs there are 2 good size bedrooms and 2 baths. This includes a large primary bedroom with private bath, and walk in closet. The 2nd floor hallway is set up beautifully for a sitting area (with overlook to below), and an office nook. The daylight basement comes complete with a partially finished section on one half, (perfect for a family room), and an oversized 2 car garage under on the other half. The land is the perfect country setting, with plenty of privacy and room to entertain. There's even a brook towards the back of the property. All Conveniently located off of Highland Cliff Rd. A very private lot, but close to everything including the Turnpike. This Property Is A Must See!!!
Welcome to 18 Victoria Lane — an immaculately maintained home offering generous living space, modern amenities, and exceptional convenience to Windham, Portland, the Lakes Region, and Maine's beautiful coastline. Step inside to a bright, inviting first floor featuring a spacious living room, a beautifully updated kitchen with granite countertops and newer appliances, a private laundry room, and direct entry to the heated two-bay garage. Cozy up by the pellet stove during the colder months, or, when warmer weather arrives, open the brand-new sliding door and extend your living space onto the newly renovated deck overlooking a private, tree-lined lot. Upstairs, you'll find four well-appointed bedrooms, two full baths, a dedicated office space (not included in the bedroom count), and a stunning private theater room complete with custom seating and full surround sound. The primary suite offers generous storage, an en-suite bath, and serene views of the expansive yard. Outside you'll find a large, private, and immaculately maintained lawn. Across the yard is the large custom shed, ready to be used for storage, a workshop, or a studio. From the large paved driveway to the 9-zone irrigation system and the well maintained landscaping, the exterior has been cultivated with just as much care as the welcoming interior. This home has been thoughtfully updated for comfort and peace of mind. Recent improvements include new heat pumps (2023), extensive exterior renovations, new siding and trim (2023), new gutters (2024), a rebuilt back deck, a new front porch, and more—no detail overlooked. Don't miss this one-of-a-kind property located in one of Windham's most desirable neighborhoods. Come experience all that 18 Victoria Lane has to offer!
Welcome to 180 Highland Cliff Road, an historic 1900 farmhouse with 52.5 acres of fields and forests in one of Windham's most sought-after rural neighborhoods, yet only minutes to Westbrook, Gorham, and beyond. Situated right next to Bumbleroot Organic Farm, this home's vintage character sets the stage for its next chapter. The kitchen, dining, and office spaces feature abundant custom cabinetry, while the home's unique features and floor plan hold endless possibility for your design vision to blossom. A separate stairway leads to a bedroom suite with its own soaking tub and walk-in closet. A private sunroom overlooks a fenced garden area and open field leading to acres of forest. Right next to the home is a 1200 sf. post and beam barn full of character, and perfect for a spacious workshop, studio, or a journey back to its roots as a home for farm animals. Don't miss this rare opportunity.
Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. The PORTLAND is the perfect blend of one-level-living meets plenty of room for guests and storage. At 1958 SF +/-, this 2 Bedroom 2.5 Bathroom attached condo with generous 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. Living on one level is easy to acheive with this model, but if 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, Age-in-Place safety features, LVP or hardwood flooring, gas or electric fireplace, and energy efficient LED lighting. Community Amenities Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the 50 acre parcel with over 6000 feet of nature trails, 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 choose your home's finishes!
Welcome Home to 8 Staples Lane, Windham! This isn't just a house; it's a beautifully renovated, move-in ready haven waiting for you! Practically every surface has been touched with quality updates, ensuring you can unpack and relax from day one. Enjoy the brand-new kitchen and bathrooms, gorgeous new flooring, and fresh paint throughout the entire home. Offering 3 bedrooms and 1.5 bathrooms, this property sits on a spacious 1.89-acre lot, providing plenty of privacy and room for outdoor activities. Key upgrades include a new, efficient monitor heater and two stunning new decks perfect for entertaining. The location offers the best of both worlds: just 12 minutes to Windham's shopping and only 25 minutes to vibrant downtown Portland. Don't miss your chance! Visit our Open House this weekend: Sunday 12/21 from 10-11:30.
Welcome to this charming 3-bedroom, 1.5-bath home offering comfort, style, and convenience in the heart of the Lakes Region. The first floor features a well-appointed kitchen with quartz countertops, a center island, and a spacious pantry. The inviting living room includes a hearth and chimney, ready for a cozy wood stove, while a dedicated office provides the perfect space for remote work or study. Step outside to enjoy the composite back deck, ideal for entertaining or relaxing. Upstairs, you'll find a full bath with laundry, a bedroom with a walk-in closet, and a spacious primary suite with French doors opening to a private deck—your own retreat for morning coffee or evening sunsets. An additional bedroom completes the second floor. Set on a private lot abutting a bird sanctuary, this home offers peace and tranquility while being just minutes from local amenities. A two-car attached garage provides convenience and extra storage. Whether you're seeking year-round living or a seasonal getaway, this property places you right in the center of everything the Lakes Region has to offer. PROPERTY IS BEING SOLD AS IS!
Cozy 3-Bedroom Ranch on 1.97 Acres with Incredible Views and Total Privacy Tucked at the very end of a private road, this secluded 3-bedroom, 1-bath ranch (built in 1994) and offers the kind of privacy that's hard to find — while still being close to everything. Inside, you'll find an open concept living room, kitchen, and dining area with a cathedral ceiling that makes the space feel bright and airy. Recent updates include the roof, furnace, and electrical, so you can move in with peace of mind. There's also a pellet stove in the large, finished walk out basement to keep the home warm and cozy all winter. The home is set up on a hill overlooking a wide-open field and wooded backdrop, with beautiful sunrises and sunsets and long views and beautiful wildlife — truly a ''relaxing view.'' Love the outdoors? You're close to Sunset Ridge Golf Course and walking/utility line trails off Anderson Road. If you've been looking for privacy, quiet, and land — without being out in the middle of nowhere — this is the one. Don't miss it. Septic design is a 2 bdrm system


Windham is located in Maine. Windham, Maine has a population of 18,343. Windham is more family-centric than the surrounding county with 31.21% of the households containing married families with children. The county average for households married with children is 30.7%.
The median household income in Windham, Maine is $86,794. The median household income for the surrounding county is $80,679 compared to the national median of $69,021. The median age of people living in Windham is 40.7 years.
The average high temperature in July is 79.4 degrees, with an average low temperature in January of 10.8 degrees. The average rainfall is approximately 49.3 inches per year, with 74.3 inches of snow per year.