Refine Search
Map
Sort by
$345,000
2 Beds ⋅ 2 Baths
Price improvement! Welcome to 1 Matinicus Way -- a charming, low-maintenance single level condo offering comfort, and convenience. This 2-bedroom, 1.5-bath is a 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!

1 Matinicus Way Unit 1, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: Getty Real Estate Services, LLC.

$340,000
2 Beds ⋅ 2 Baths
Enjoy the ease of single-level living in this beautifully maintained condominium located in a welcoming 55+ community in Windham. Offering comfort, convenience, and privacy, this home features a versatile entry area that can serve as a sitting room or home office, a spacious kitchen with pantry, monitor and electric heat, and an attached one-car garage. Step outside to your own private, fenced backyard highlighted by attractive landscaping--an ideal space to relax, garden, or enjoy Maine's changing seasons. Residents also enjoy access to a well-maintained community gazebo, creating a wonderful gathering place to connect with neighbors and friends. Conveniently located just minutes from shopping, restaurants, healthcare, golf courses, walking trails, and the recreational opportunities of Sebago Lake, with Portland less than 30 minutes away. If you're looking for low-maintenance living with a balance of privacy, community, and easy access to everyday amenities, this home is well worth a closer look. Buyer to verify square footage

5 Walnut Dr Unit C-2, Windham

Listing courtesy of EXP Realty.

Selling Office: Maine Home Connection.

$336,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained 3-bedroom, 2-bath home offering spacious single-level living in a quiet neighborhood just minutes from downtown Windham. The open, functional floor plan features a bright kitchen with a breakfast bar, dining area, and two comfortable living spaces, including a cozy sitting room with a natural gas fireplace. The private primary suite features a walk-in closet and en-suite bath, while two additional bedrooms and a full bath are located on the opposite end of the home for added privacy. Major updates include a new septic system (2021), furnace overhaul (2026), drilled well (2014), and front ramp and side stairs (2020). Additional highlights include natural gas heat, a paved circular driveway, a full ADT security system, and a 16 x 30 powered storage shed. Situated on a level, private lot surrounded by mature trees, this move-in ready home has the perfect combination of comfort, convenience, and peace of mind just minutes from shopping, dining and Sebago Lake. Open house Sunday, August 9th 10-11:30!

254 Varney Mill Rd, Windham

Listing courtesy of Signature Homes Real Estate Group.

Selling Office: Portside Real Estate Group.

$335,000

8 Bedrock Ter, Windham

Listing courtesy of A Team Realty.

Selling Office: Pine Tree Realty of Maine.

$335,000
2 Beds ⋅ 1 Baths
Looking for a petite place to plant your roots in well-loved Windham? This cute 2-bedroom, 1-bath ranch is your answer! The cheerful kitchen's granite countertops, gas stove & stainless steel appliances will have you smiling while sauteing. The living area's abundant natural light makes for boosted moods & happy houseplants alike. Single-level living makes life a breeze, with two bedrooms, laundry hookups, and a bathroom at the ready. Playing outside? Take your pick from the front or back yard. A shed awaits your toys & tools. Windham has it all: easy access to lakes & mountains, as well as every imaginable amenity. Gorham, Westbrook & Portland are a short drive away when adventure calls. A sweet opportunity to hang your hat in a special spot - come take a look!

23 Land Of Nod, Windham

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com

Selling Office: King + Miller Real Estate.

$330,000
2 Beds ⋅ 1 Baths
402 Roosevelt Trail offers the perfect blend of recent updates, convenience, and space to enjoy Maine living. Situated on a generous 1.42-acre lot, this property features a spacious, fully fenced backyard--ideal for entertaining, pets, or simply relaxing in your own private outdoor setting. Significant improvements completed by the previous owner in 2024 include a new roof, new leach field, replacement of side and rear steps, installation of a patio, bathroom ventilation fan, and updates to the heating system addressing prior deferred maintenance. The current owner has continued the care of the home with fresh exterior painting along the basement portion. Inside, the home features durable vinyl plank flooring and a comfortable layout that flows easily from the living area into the kitchen, creating a warm and functional space for everyday living. Location is a standout feature--just 3.4 miles (approximately 7 minutes) to Windham's commercial center, offering convenient access to Hannaford, Lowe's, Home Depot, Portland Pie, Chipotle, Starbucks, Smitty's Cinema, and more. Outdoor enthusiasts will appreciate being only 15 minutes from Sebago Lake's public boat launch, while Portland's Old Port is just a 30-minute drive away. A well-maintained home with key system updates already completed, set on a sizable lot in a highly convenient location--this is an opportunity not to be missed. Open House on Saturday, May 16th from 11:00 to 01:00

402 Roosevelt Trl, Windham

Listing courtesy of Benchmark Real Estate.

Selling Office: Keller Williams Realty.

$327,800
1 Beds ⋅ 1 Baths
This Charming ranch-style log cabin offers 5 rooms, 1 bedroom, 1 bath, 960 sq ft, and a 2-car garage. Enjoy 100 feet of shared waterfront—just a short walk to North Gorham Pond and the Presumpscot River. Minutes to Sebago Lake, North Windham shopping, and easy drives to Downtown Portland and Pleasant Mountain. Ideal for year-round living, a vacation getaway, or Airbnb investment. Schedule your private showing today!

17 Easter Ave, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: Keller Williams Realty.

$325,000
3 Beds ⋅ 1 Baths
ESTATE SALE! The property is being sold AS IS. 3-bedroom split-level home situated on a nicely treed lot in an established Windham neighborhood. Great location just steps from Windham's shopping district, restaurants and everyday amenities, while also being very close to Little Sebago Lake and area recreation. The main level features hardwood floors, an open kitchen and dining area, living room, primary bedroom and full bath. The lower level offers two additional bedrooms along with a family room. The property has had many updates over the years, including improvements to the kitchen and bathroom. The home does need additional cosmetic updating and finishing throughout, offering a great opportunity to make it their own. Outside you'll find a good-sized deck overlooking the backyard, an oversized detached two-car garage, additional storage shed and a mature, nicely treed lot. This is an estate sale, and the property is being sold strictly as-is. Seller will not be making repairs or improvements prior to closing. All parties encouraged to perform their own due diligence regarding the property and its condition. Home will not qualify for FHA/VA/RD financing but possibly conventional financing or private funding! Property Shown Aug 17-Aug 30. Offers can be accepted anytime.

11 Oak Ln, Windham

Listing courtesy of American Real Estate.

Selling Office: Keller Williams Realty.

$325,000
Don't miss this unique opportunity to live on a generous 11.23-acre wooded parcel situated in an area of quality high-end homes and serviced by underground power and public water. According to Town records, an existing septic system was approved and installed in the late 1970's. The property includes abandoned structures, including: 1) an old camp (circa 1980) built on piers and posts, featuring an interior fieldstone chimney—a potential salvage piece or inspiration for a new build 2) a one-of-a-kind above-ground pool elevated on a steel beam structure, creating a dramatic 'floating' visual effect; and 3) a screened-in pavilion with a striking fieldstone fireplace, located adjacent to the pool area. The future owners may choose to remove the existing structures and start fresh or explore salvaging parts of the structures and incorporate them into a new design. Enjoy the best of both worlds, living in Windham: it's less than a half-hour drive to Portland, yet provides quintessential rural Maine scenery, including the newly restored Babb's Covered Bridge. Recreational opportunities abound, including hiking or walking at the Donnabeth Lippman Park; Chaffin Pond; and the Lowell Nature Preserve; and mountain biking at the East Windham Conservation area, which is comprised of 700 acres of land and is also a part of a 2,000-acre conservation corridor. Seller requests no drive-by's. Notice is required to view the property. This property is also offered as a residential listing (see MLS #1640492).

17 Secluded Dr, Windham

Listing courtesy of Gallant Real Estate.

Selling Office: Gallant Real Estate.

$324,900
2 Beds ⋅ 1 Baths
Are you tired of renting? Have you wanted to own your own home but it seems out of reach? Have you been looking for a year round vacation get away home? Well, here is your opportunity to own an adorable 2 bedroom home in Windham with a right of way to Pettingill Pond! Imagine, you are only 2 miles away from North Windham with its outstanding array of shopping and restaurants. Pleasant Mountain ski area is about 45 minutes away, downtown Portland is about 40 minutes. Talk about location location location for this simply adorable year round home. The charming front porch with views of Pettingill Pond is perfect for summer evenings with friends watching the sunset. Out back, the over sized backyard has the perfect spot for nighttime fires and roasting marshmallows. The Seller has refreshed the interior with new flooring making this home feel light, bright and welcoming. Some of the Seller's favorite things about the home are the walkable and cheerful neighborhood, the close proximity to a network of trails, Little Sebago boat launch is one mile away, paddleboarding and kayaking on the pond, listening to the loon calls, fishing and ice fishing and the snowmobile trails are nearby. The home is cozy, utilities are affordable and the backyard is perfect for entertaining. So, if you are looking for a year round home, or a vacation get away, 73 Anglers Road will check all of the boxes you are looking for.

73 Anglers Rd, Windham

Listing courtesy of Century 21 First Choice Realty. gregory.fall@century21.com

Selling Office: Legacy Properties Sotheby's International Realty.

$321,100
3 Beds ⋅ 2 Baths
Welcome to 107 Harvest Hill Road, a 1,364 square ft colonial in Windham's Sebago Heights neighborhood. This home offers 3 bedrooms, 1.5 baths, and an attached 1-car garage, all sitting on a 1.04-acre lot. While the house maintains classic colonial charm, it does need repairs and updates, giving you a real chance to make it your own. Outside your door, you're in a community rich with recreational options. If you love lakeside recreation, you're just a short drive from Sebago Lake State Park, which features swimming, boating, camping, and trails. As for convenience, Windham is only about 12 miles from Portland, with major routes like U.S. 202 and 302 running through town.

107 Harvest Hill Rd, Windham

Listing courtesy of Excellence Realty.

Selling Office: The Maine Real Estate Experience.

$315,000
2 Beds ⋅ 1 Baths
Well built, perfectly located ranch with water access to Highland Lake just a 1 minute walk away! Sunny open concept turn key 12 year old house close to all Windham amenities with shared access to multiple beaches and boat ramps... Full dry basement with insulated and sheet rocked ceiling, and a 2025 Hot water heater! Town has house listed as one bedroom but there is a second smaller room that could work as a second bedroom, just no closet.

1 Orchard Rd, Windham

Listing courtesy of The Maine Real Estate Experience.

Selling Office: The Collective Real Estate Co.

$314,900
2 Beds ⋅ 1 Baths
Conveniently located near Windham's shopping, dining, and lakes, this move-in ready home is a great choice for those starting out, downsizing, or seeking low-maintenance living. This charming home features an updated kitchen and bath, new flooring, and a first-floor primary bedroom. Major updates were completed in 2023, including a new roof, furnace, and siding on the home, plus new siding and roof on the oversized garage. The garage offers excellent storage or hobby space, though buyers should note some unevenness in the back corner of the floor due to settling.

81 Main St, Windham

Listing courtesy of RE/MAX Oceanside.

Selling Office: Keller Williams Realty.

$308,000
2 Beds ⋅ 2 Baths
Easy Condo Living!! Great Amenities!! Perfect Location!! Welcome to 29 Baxter Woods Trail. This 2 bedroom, 1.5 bath condominium is well appointed, and has a ton of charm. The well lit living room, and kitchen dining combo, lead you out a slider onto a beautiful private deck. perfect for entertaining, chilling and grilling. Upstairs are two nice sized bedrooms, well lit and very comfortable. Also has a full unfinished basement for plenty of storage. Some of the great amenities include inground pool, tennis court, heat pumps, and Whole house generator. Don't miss this one!! This Property Is A Must See!!

29 Baxter Woods Trail, Unit 29, Windham

Listing courtesy of Getty Real Estate Services, LLC.

Selling Office: Keller Williams Realty.

$304,000
2 Beds ⋅ 1 Baths
Well-maintained 2-bedroom, 1-bath ranch offering single-level living on a wooded 0.78-acre lot with 100 feet of deeded Pleasant River frontage. Convenient Southern Maine location close to shopping, restaurants, and major commuter routes, with easy access to Gorham and the Greater Portland area. Interior features include an updated kitchen, comfortable living room, two bedrooms, and a full bath. A full basement provides additional storage space. Exterior features include a fenced-in backyard and a natural wooded setting. A path through the woods leads to the Pleasant River, where the deeded frontage offers recreational opportunities and a quiet connection to nature. Suitable for first-time buyers, downsizers, or those seeking manageable one-level living in Windham.

543 River Rd, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: Dream Home Realty LLC.

$300,000
2 Beds ⋅ 2 Baths
Easy, low-maintenance living in Trailwood Village Condo Association. This 2-bedroom, 2-bath condo offers the ease of single-level living with a functional layout, dedicated laundry area, and additional basement storage to keep things organized. The association covers exterior maintenance, landscaping, and snow removal--making it a practical, low-stress option for those looking to simplify or downsize. Located in Windham, you'll have convenient access to shopping, dining, and outdoor recreation, including Sebago Lake and local trail systems, with an easy commute to Portland and surrounding areas.

9 Settlers Ct Unit 9, Windham

Listing courtesy of Keller Williams Realty. scottandsunny@kw.com

Selling Office: Coldwell Banker Realty.

$299,900
2 Beds ⋅ 2 Baths
Have you been patiently waiting for an END UNIT CONDO TOWNHOUSE to come on the market in the sought after neighborhood of Baxter Woods Trail for under 300K?Your wait is over!This meticulously maintained 2 Bedroom,1 1/2 bath is conveniently located near Windham Center & all that the Sebago Lakes region has to offer!This home offers tons of natural light coming into the home & has an open concept kitchen & dining room area that had a recent facelift w/NEW kitchen cabinets, counters,& stainless steel appliances. The home offers REAL hardwood floors on the first floor (tile in both bathrooms) & newer carpet on the second floor where the 2 bedrooms and Full bath are located. The first floors open-concept living space flows effortlessly to a private deck off the kitchen slider that you need to see to truly appreciate as it isn't just in the back of the home but also wraps around the side of the property to allow for a great entertaining space or a quiet, private location looking out into the back yard & woods to get away! The full basement offers a very large laundry area with great storage potential and bring your ideas to finish off the space to what will work for you! There is also an attic space above the 2nd floor allowing for additional storage. The low 230 per month association fee includes resort-style amenities just steps from your door, including a refreshing inground pool & a tennis court (currently closed). The association fee also includes all exterior maintenance, snow removal to include shoveling your walkway, landscaping (you can still decorate the area around your front door), septic & a central mailbox area as you enter into the association. You are responsible for your water bill which currently runs about $15 per month, your electric bill, and your K-1 for the Monitor Style heater in the living room (electric baseboards elsewhere). Come take a peek at this meticulous property, you won't be disappointed!

57 Baxter Woods Trail, Unit 57, Windham

Listing courtesy of Moody Maxon Real Estate.

Selling Office: Real Broker.

$299,000
2 Beds ⋅ 2 Baths
This charming 2-bedroom, 1.5-bath condo on Whites Bridge Road in Windham offers a comfortable and practical layout with added flexibility thanks to a bonus room in the basement--perfect for a home office, gym, or guest space. Enjoy easy indoor-outdoor living with a walkout to the backyard and a private deck ideal for relaxing or entertaining. Conveniently located near shopping, dining, and everyday services, it also provides quick access to Portland and is just a short drive from the beauty and recreation of Sebago Lake. Affordable and full of potential, this home is an excellent opportunity for buyers looking to achieve homeownership or find a smart bridge to their next move. For a video walk-thru go to YouTube and enter the property address. Seller Concessions Available.

24 Whites Bridge Rd Unit 24, Windham

Listing courtesy of Keller Williams Realty. 207-232-6127

Selling Office: American Real Estate.

$285,000
2 Beds ⋅ 1 Baths
Welcome to this move-in ready, beautifully updated 2-bed, 1-bath condo nestled in a quiet, peaceful neighborhood just minutes from Windham! The main level boasts bright, sunlit living spaces with fresh paint, modern flooring, and updated finishes throughout, including a refreshed kitchen and bath. The true standout feature is the newly finished basement, offering substantial versatile living space ideal for a home office, family room, or gym. Enjoy peaceful surroundings on your private deck as well as the added convenience of Windham's shopping, dining, and outdoor recreation right around the corner. Turn-key comfort in a prime location!

336 Pope Rd Unit 2, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Fontaine Family-The Real Estate Leader.

$284,000
2 Beds ⋅ 2 Baths
Welcome home to this bright and cheerful 2-bedroom, 1.5-bath townhouse-style condo--an ideal opportunity for first-time buyers looking for comfort, value, and convenience. Move right in and enjoy an updated kitchen with granite countertops and stainless steel appliances, along with fresh finishes throughout that make the space feel modern and inviting. The recently added first-floor half bath is a rare bonus, adding everyday ease for you and your guests. Natural light fills the home, creating a warm and welcoming atmosphere, while on-site laundry and additional storage near parking add practical convenience. Step outside and take advantage of easy access to the Mountain Division Trail--perfect for walking, biking, or simply enjoying the outdoors. With Portland just a short drive away, you'll love having both nature and city amenities within reach. Low-maintenance living, thoughtful updates, and a move-in ready condition make this a smart and stress-free place to start your homeownership journey.

18 Cosmic Way Unit 16, Windham

Listing courtesy of RE/MAX Shoreline.

Selling Office: The Maine Real Estate Experience.

$283,550
2 Beds ⋅ 2 Baths

7 Baxter Woods Trl Unit 7, Windham

Listing courtesy of EXP Realty.

Selling Office: White Wave Real Estate.

$280,000

856 Roosevelt Trail Trl, Windham

Listing courtesy of Landing Real Estate.

Selling Office: Landing Real Estate.

$275,000
2 Beds ⋅ 1 Baths
This beautifully maintained condo offers true one-level living in one of Windham's most desirable neighborhoods. The home has been meticulously cared for and is move-in ready. Low maintenance living with easy access to shopping, restaurants, lakes and all that Windham has to offer. A wonderful opportunity for buyers seeking comfort, convenience and quality.

8 Settlers Ct Unit 8, Windham

Listing courtesy of Landing Real Estate.

Selling Office: Keller Williams Realty.

$275,000
4 Beds ⋅ 3 Baths
Nestled at the end of a quiet dead-end road, this unfinished home offers a rare opportunity to create your own private retreat in Windham. Set on a peaceful, wooded lot, the property provides a sense of seclusion while still being within easy reach of town amenities and nearby lakes. The structure is partially complete—ready for someone with vision to bring it to life and finish it to their own style and specifications. Whether you're a builder, investor, or buyer looking for a custom project in a desirable area, this property is full of potential. Enjoy the natural setting, privacy, and the satisfaction of making this house your own.

11 Dragonfly Dr, Windham

Listing courtesy of Dan The Man Real Estate.

Selling Office: Keller Williams Realty.

$274,500
2 Beds ⋅ 1 Baths
14 Sabbady Point Road recently remodeled home with updates and a 2 car garage. This affordable home is centrally located in Windham and is convenient to all shopping and services Windham has to offer. Minutes to Big Sebago Lake and Little Sebago Lake. This is a great affordable home. Property is Located in the C-1 district

14 Sabbady Point Rd, Windham

Listing courtesy of Kre Brokerage Group.

Selling Office: Coldwell Banker Team Real Estate.

$260,000
Versatile Quonset Hut Style Building - Live & Work Opportunity! Discover a unique chance to combine home and business under one roof! This 2,000 sq. ft. Quonset hut-style building offers the perfect setup for contractors, landscapers, machine shops, manufacturing, grow operations, or countless other uses. The building features radiant floor heat, excellent insulation, and bright lighting throughout, making it efficient and comfortable year-round. Inside, you'll find a small apartment for convenient on-site living, plus dedicated office space to keep your business organized. Almost 2 acres offers ample outside parking. Whether you're looking for a place to run your construction business or seeking a flexible property to adapt to your needs, this well-designed space is a rare opportunity.

66 James Way, Windham

Listing courtesy of Spectrum Real Estate.

Selling Office: Spectrum Real Estate.

$260,000
So many possibilities with this land! Build your dream home only 10 minutes from North Windham's shopping, restaurants and amenities. Large lot with potential to split.

Tavern Hl, Windham

Listing courtesy of Landing Real Estate.

Selling Office: Willis Real Estate.

$250,000
2 Beds ⋅ 1 Baths
Property is being sold as-is and will require updates and repairs, making it ideal for investors, contractors, or buyers looking for a project. With vision and effort, this home could truly shine.

28 Presumpscot Rd, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Portside Real Estate Group.

$249,000
1 Beds ⋅ 1 Baths
This is a chance to get a deal on a great waterfront property in North Windham, Maine! This year-round home features 55 Feet of owned water frontage on Pettengill Pond. With its quiet location on a private dead end road, coupled with the convenience of local shopping and restaurants close by, this unique property is ready for your personal touches!

138 Anglers Rd, Windham

Listing courtesy of The Real Estate Store.

Selling Office: Keller Williams Realty.

$221,000
4 Beds ⋅ 1 Baths
This ranch-style home could offer the perfect balance of serenity and recreation on its 1.99-acre setting. A wrap-around deck overlooks the in-ground pool and pool house, while a screened gazebo with a Jacuzzi could offer a relaxing retreat. The expansive patio is perfect for entertaining or simply enjoying the private setting. Inside, the main level includes three bedrooms, a full bath, an open concept living-dining-kitchen area with direct access to the deck. The spacious, partially finished full basement adds versatility with a laundry area, bonus living space, and double doors leading to the lower patio. A detached four-car garage with overhead storage provides plenty of room for vehicles, tools, and recreational gear. With its blend of indoor comfort and outdoor amenities, this property could be transformed back into a relaxing home for recreation enthusiasts in a picturesque setting. Condition of chimney, roof, heating and all other systems is unknown. Due diligence encouraged. Property to be sold ''AS-IS'' condition. All personal belongings on the property convey. Seller is a third party personal representative for the estate and is only available between 9 am-5 pm M-F, not to include holidays. ''Personal Representative'' deed being conveyed. Agents & Special Administrator have disclosed ALL known information about the property. Sale of property is subject to Cumberland County probate court. **** Agents please refer to internal remarks and advise your client(s) accordingly.

674 River Rd, Windham

Listing courtesy of On Point Realty.

Selling Office: Maine Real Estate Co.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Privacy Policy

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.