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5 Hidden Pines Dr, Windham
$525,000
3 Beds ⋅ 3 Baths
Enjoy comfortable one-floor living in this nicely maintained Ranch-style home, tucked away on a quiet dead-end road in Windham. Set on 1.94 private acres, this three bedroom, two-and-a-half-bath home offers a welcoming layout with plenty of space to relax and entertain. The open-concept kitchen, dining, and living area flow seamlessly onto a large, private back deck—perfect for outdoor dining and enjoying the peaceful surroundings. The main level includes a primary bedroom, a guest bedroom, and a large full bath. The laundry room and a half bath are conveniently located just inside the direct entry to the garage. The finished lower level provides even more living space, featuring a bonus room with a bar area and pool table, ideal for entertaining. A third bedroom, full bath, and office complete the lower level, offering flexibility for guests, working from home, or additional living needs. Enjoy the best of both privacy and convenience, with easy access to Dundee Park, Sebago Lake, Windham Center, Westbrook, Portland and beyond.

5 Hidden Pines Dr, Windham

Listing courtesy of Portside Real Estate Group.

579 River Rd, Windham
$335,000
3 Beds ⋅ 1 Baths
Build equity and bring your vision to 579 River Road! Set on 2.17 acres with 151 feet of frontage on the Pleasant River, this Windham property offers good bones and plenty of opportunity to make it your own. The interior needs cosmetic updating, making it an appealing equity-building project for buyers ready to put their ideas to work. A new roof installed last year with a 50 year warranty and an updated septic system give you a head start on improvements. The huge barn provides ample space for storage, hobbies, or workshop projects, plus an additional room upstairs. Enjoy the riverside setting approximately 20 minutes from Portland and 10 minutes from North Windham's shopping district and the Lakes Region. Offered as-is and ready for its next chapter, this property invites you to bring your tools, creativity, and plans to unlock its potential.

579 River Rd, Windham

Listing courtesy of Landing Real Estate.

2 Shepherd Ln Unit 1, Windham
$510,000
3 Beds ⋅ 3 Baths
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!

2 Shepherd Ln Unit 1, Windham

Listing courtesy of RE/MAX By The Bay.

2 Shepherd Ln Unit 1, Windham
$510,000
3 Beds ⋅ 3 Baths
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!

2 Shepherd Ln Unit 1, Windham

Listing courtesy of RE/MAX By The Bay.

6 Shepherd Ln Unit 3, Windham
$479,900
3 Beds ⋅ 2 Baths
Brand new - just completed! Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. 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!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

6 Shepherd Ln Unit 3, Windham
$479,900
3 Beds ⋅ 2 Baths
Brand new - just completed! Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. 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!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

120 Main St, Windham
$335,000
3 Beds ⋅ 1 Baths
Offering the ease of single-level living, this 3-bedroom, 1-bath Ranch in Windham makes smart use of its footprint with a straightforward, functional layout. A ramped entrance adds convenient access, while hardwood flooring and natural light bring warmth to the interior. The kitchen serves as the main gathering space, with ample cabinetry and room for everyday dining. Three bedrooms are complemented by a separate room, creating flexibility for a living room/den, home office, hobby room, workout space, or additional storage depending on your needs. Outside, the fenced-in backyard provides a defined area for gardening, recreation, or relaxing outdoors. A detached two-car garage adds valuable parking and storage, while the basement offers additional utility and storage space. Conveniently located in Windham, the home is close to local shopping, dining, recreation, and nearby lakes and outdoor destinations. With single-level living, flexible bonus space, a fenced yard, ramped entry, and a two-car garage, this Ranch offers practical living in a convenient location.

120 Main St, Windham

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

10 Reba Ln, Windham
$449,500
3 Beds ⋅ 1 Baths
Welcome to 10 Reba Lane! This is a centrally located, private home. It's located close to Dundee Park in a quiet, residential part of Windham. This ranch-style home allows for one-floor living while remaining spacious and welcoming. This home offers opportunity for both first-time home buyers, and people looking to "right size" without sacrificing creature comforts and functionality. Plenty of garage space, a convenient layout, and a fantastic location make this a great home for every lifestyle you could dream of. Upon entering the breezeway, you are greeted by the high ceilings, and a sliding glass door inviting you to the backyard. The kitchen has been completely updated, with stainless steel appliances, and newer cabinets and countertops. This home gets lots of natural light, especially through the big windows in the living room and primary bedroom. The partially finished basement means an abundance of room for storage, entertaining, and so much more. A perfect location: it's easy to commute to Portland, Oxford, and to Lewiston/Auburn. Schedule your showing today! The finished area in the basement has been approved by the town, and documentation is publicly available.

10 Reba Ln, Windham

Listing courtesy of Keller Williams Realty.

87 Pope Rd, Windham
$399,263
3 Beds ⋅ 1 Baths
OPEN HOUSE Sunday 10/25, 11:00am - 1:00pm! SELLER TO FUND DISCOUNT POINTS/TEMP INTEREST RATE BUYDOWN. Welcome HOME! Charming raised ranch with the potential of 3 bedrooms. The dining room, with built in closet, could easily be converted to a third bedroom or office space. With a wall of windows, the generous sized great room, flooded with natural light, could easily include both dining and living room. Refinished original hardwood flooring throughout the home. The kitchen showcases many of its original charm including the wooden countertops, pull-out cutting/pastry board, vintage copper hardware and farmer's sink. Can you picture having your morning coffee in the eat-in kitchen? An expansive front lawn positions the house away from the road. The large back yard and woods, along an old rock wall, offers space for young explorers to play. Lower level provides expansion opportunities and includes the original one car drive-in garage space now boarded up and used for additional storage. Location is close to retail, restaurants, recreational activities, area lakes and is easy commute to Portland. Property has been recently upgraded with newly installed septic system, electrical service, plumbing, heat pump and other building updates and renovations. It's now ready to be your new HOME.

87 Pope Rd, Windham

Listing courtesy of Gardner Real Estate Group.

3 Acorn Ln, Windham
$499,900
3 Beds ⋅ 3 Baths
Spacious Windham Colonial with endless possibilities! Welcome home to this beautifully maintained 3-4 bdrm, 2 1/2 bath colonial offering approx. +/-2500 sq.ft of living space, plus an impressive 974 sq.ft finished space above the garage- perfect for in-law suite, home office, game room, studio or entertainment space. Bring your own ideas and make it your own! The main house offers spacious layout, including a primary suite with two closets and a private bath featuring a corner soaking tub and skylights. A perfect sized mudroom provides a convenient transition from the outdoors, while the partially finished basement offers two large finished rooms that could serve as a family room, office, workout area or hobby space. Step outside and you'll love the beautifully manicured private yard, large patio and deck overlooking the enclosed pool. The fenced in backyard creates a wonderful setting for summer gatherings, entertaining, relaxing and enjoying your own private oasis. Conveniently located close to Windham village, shopping, bank, restaurants and everyday amenities while still offering the privacy you want at home. So much space, so many possibilities, and a location that makes everyday living easy- come see all this Windham Colonial has to offer!

3 Acorn Ln, Windham

Listing courtesy of Maine Real Estate Choice.

4 Frontier Dr, Windham
$689,000
3 Beds ⋅ 3 Baths
This new Colonial home offers thoughtfully designed living spaces set in a peaceful location just minutes from local amenities, and surrounded by private woods. Enjoy the sunny exposure and spacious open floor plan as you enter. A gas fireplace is the focal point of the large living room. The kitchen features quartz countertops, a center island, pantry, and new appliances. The first floor also offers a functional mudroom entry, and a great back deck. Three bedrooms are located upstairs, including a primary suite with two walk-in closest and full bath. Gaze out at wooded views from the back deck, while the full basement provides great potential for storage, hobbies, or future finishing. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Optional heat pump upgrade for energy efficient cooling.

4 Frontier Dr, Windham

Listing courtesy of RE/MAX By The Bay.

29 Riverside Rdg, Windham
$450,000
3 Beds ⋅ 2 Baths
Welcome to this well-maintained 3-bedroom, 1.5-bath home nestled on over 2 acres in a quiet Windham neighborhood, yet conveniently located close to all that the area has to provide. The home features a spacious two-car garage beneath the two-story residence. Step inside to a generous open-concept living, kitchen, and dining area, creating a comfortable space for everyday living and entertaining. Just off the main living area are a full bathroom, separate laundry area, and first-floor bedroom. From the kitchen, step out onto the large back deck and enjoy the peaceful natural setting and surrounding woods. Upstairs, you'll find two generously sized bedrooms and a convenient half bath. Outside, enjoy the privacy of over 2 acres, with quiet roads for leisurely walks and trails throughout the property. A wonderful location just minutes from in-town Windham and approximately 20 minutes to Westbrook. Don't miss the opportunity to make this peaceful property your new home! OPEN HOUSE, SATURDAY, OCTOBER 31ST FROM 11:00 AM - 12:30 PM!

29 Riverside Rdg, Windham

Listing courtesy of Signature Homes Real Estate Group.

5 Frontier Dr, Windham
$869,000
4 Beds ⋅ 3 Baths
This soon to be completed contemporary colonial home sits back from the road on a sunny southern facing lot, with peaceful views and a private wooded surrounding. The beautiful new kitchen features oak cabinetry, quartz countertops, a walk-in pantry, and an island that invites gathering. Entertain guests in style in the stunning open concept dining and living room, windows on three sides bathing the space in natural light, and a cozy gas fireplace to gather around on chilly evenings. The flexible floor plan of this home offers versatility to suit your lifestyle. Upstairs, the spacious primary suite awaits, offering a serene haven with dual walk-in closets and a luxurious bathroom featuring a tiled shower. Three additional bedrooms, a full bath, and a convenient laundry room complete the second level. A daylight, walk-out basement is finished as a large family room, with space to workout, work from home, or indulge in hobbies. Additional features include an attached garage and an enviable mudroom to keep things organized. Surrounded by nature but minutes to Windham shopping, amenities, and a short drive to lakes and mountains. Move in before the holidays and indulge in a magnificent new lifestyle!

5 Frontier Dr, Windham

Listing courtesy of RE/MAX By The Bay.

111 Harvest Hill Rd, Windham
$535,000
3 Beds ⋅ 2 Baths
Welcome to this immaculate 3-bedroom, 2-bath Colonial set on 1.03 acres in the desirable Sebago Heights neighborhood near the Windham-Raymond line. Built in 2012, this inviting home features an open-concept floor plan that creates a comfortable flow between the living, kitchen, and dining areas—ideal for everyday living and entertaining. Step outside to enjoy the beautifully landscaped property, established raised garden beds, and tucked-away backyard offering space to garden, relax, and gather with friends and family. The spacious deck just off the dining area is perfect for summer grilling and outdoor dining. Inside, enjoy the convenience of a practical layout, ample closet space, and included stainless steel kitchen appliances. A newer heat pump provides efficient cooling during warmer weather, and heats the entire home in the winter. The attached one-car garage offers convenient entry and additional storage potential. The full, unfinished daylight basement provides options for additional recreational space, hobbies, a home gym, or storage. Located on a town-maintained road with public water, this property offers a wonderful balance of neighborhood living and outdoor enjoyment. Shopping and everyday amenities are nearby, and a Sebago Lake public beach is approximately five minutes away. Well maintained and ready for its next owner, this home offers comfort, outdoor space, and a convenient Windham location. Come see all it has to offer!

111 Harvest Hill Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

1 Dolley Farm Rd Unit 15, Windham
$474,000
3 Beds ⋅ 3 Baths
"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!"

1 Dolley Farm Rd Unit 15, Windham

Listing courtesy of The Flaherty Group.

32 Pennywhistle Dr, Windham
$775,000
3 Beds ⋅ 3 Baths
This stunning home is bathed in natural light and beautifully appointed. As you enter the front door you will find a 2 story foyer and living room which flows into the dining room and to the large open kitchen with dining area overlooking the back yard and cabinets galore. The 1st floor also offers a sunken den/office with built ins, a powder room with laundry, and mudroom leading to the heated garage. Up the bright open stairway to a spacious loft that can be a study or exercise area and leads to the primary suite with a recently completed bath offering a soaking tub and a large custom shower. There are 2 additional bedrooms and guest bath. The lower level offers a walk out partially finished daylight basement with sliders leading to the back yard. An expansive, fully fenced, a 0.7-acre yard surrounded by 34 acres of preserve on 2 sides. Conveniently located 8 miles from Portland, 5 miles from Gorham or Windham centers. This home offers much of the best of Southern Maine, with high efficiency gas heat as well as a heat pump for year round comfort.

32 Pennywhistle Dr, Windham

Listing courtesy of Keller Williams Realty.

10 Stillwater Dr Unit 3134, Windham
$335,000
2 Beds ⋅ 2 Baths
*NOW $15,000 in BUILDER INCENTIVES AVAILABLE* Own for $2400 per month*! Ready in November! This third floor unit features 9' ceilings and offers 991 square feet of bright, open-concept living. This thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll find timeless shaker-style cabinetry, granite countertops, stainless steel appliances, and an in-unit washer and dryer -- all curated to make daily living feel seamless. Large windows fill the home with natural light, creating an airy atmosphere that feels both welcoming and refined. Inspired by the expansive beauty of Sebago Lake -- Windham's most iconic natural landmark -- The Sebago unit is the largest home available at Windham Village, designed for those who appreciate space, comfort, and effortless living. Shared amenities include, a gym, co-working space, community room, dog wash, storage lockers and more! *Estimated Principal, Interest, Est taxes & PMI; 5 year fixed, 30 year term, 3% down, 6.827% APR, subject to approval.

10 Stillwater Dr Unit 3134, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

22 Daybreak Ln Unit 11, Windham
$799,000
3 Beds ⋅ 3 Baths
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 & Appliances. 22 Daybreak features a floor to ceiling Gas Fireplace feature, Upgraded Cafe Appliance Package, Light & 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. Community Amenities to Include: Tennis & Pickle Ball court, two-level clubhouse with fitness center, full kitchen and function/meeting space, private access to the 53 acre parcel with over 6000 feet of nature trails, 585 feet of lake front to carry in kayaks, canoes and paddle boards, plus a community maintained dock. Located JUST 10 MILES from Downtown Portland, residents will enjoy UNBEATABLE proximity to top rated health care and hospitals, Maine's finest dining and endless entertainment options. Have you ever imagined a life immersed in nature full of boating, skiing, golf, shopping, dining, sports & activity clubs, and LOW MAINTENANCE? The way 55+ life should be can be found here in The Cove at Highland Lake!

22 Daybreak Ln Unit 11, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com

7 Mancini Rd, Windham
$538,000
3 Beds ⋅ 2 Baths
OPEN HOUSE, October 25th, 10am to 12PM. Interest rate buy down is negotiable. Set on 2.4 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. Mature raspberry and blackberry bushes offer seasonal berries right from the yard, while a beautiful magnolia tree, lilacs, and an Oriental apple tree add established character and seasonal color to the property. With 2.5 acres and only two neighboring homes along the road, the property offers a sense of privacy without feeling isolated. Located just off Falmouth Road, the home strikes a great balance between a quieter setting and convenient access to town. Windham's shopping, restaurants, and everyday amenities are just a short drive away, while Portland is also within easy reach. With acreage, privacy, a pool, hot tub, useful outbuildings, and a convenient location, this property offers plenty of opportunity to make it your own.

7 Mancini Rd, Windham

Listing courtesy of Landing Real Estate.

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