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$460,000
3 Beds 2 Baths
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 door opener with remote, Ring doorbell, furnace igniter, and approximately $15,000 in 2026 additions. The attached garage adds everyday convenience and storage. As part of a small condominium association, owners enjoy weekly trash removal, while the association handles exterior maintenance and septic. With Collins Pond access, a private-feeling setting, flexible living space, and numerous recent improvements, this property offers a unique opportunity to enjoy low-maintenance condo living without giving up the outdoor features and comfortable feel of a home. Conveniently located near the heart of North Windham, 8 Port Drive, Unit 8 is ready for its next owner to settle in and enjoy all that this property and location have to offer. Whether relaxing on the spacious deck, enjoying the fenced outdoor area, or heading to Collins Pond, there is plenty to appreciate inside and out. Natural gas heat and practical utility costs further complement the easy-living design. Come experience this home!!

8 Port Dr Unit 8, Windham

Listing courtesy of Real Broker.

$429,000
2 Beds 2 Baths
Welcome Home! This meticulously maintained townhouse offers an open floor plan with numerous amenities and upgrades including a freshly painted interior, custom design kitchen with granite counter tops and stainless appliances. Plus recently added modern comforts like the high efficiency heat pumps for climate control and a standby generator hook up. The high ceilings and large windows flood the space with natural light. There are 2 full baths and both have been upgraded. The 2nd floor bath was totally redone with a custom shower and glass door. The full basement offers plenty of storage while the large bonus room offers plenty of flexible uses including a home office, family room or 3rd bedroom. In addition to the large amount of living space there is a private deck and patio ideal for enjoying the outdoors relaxing or entertaining. while backing up to common green space for added privacy. This unit is part of a well-run association located in a peaceful neighborhood with easy access to local walking trails and outdoor recreation while being just minutes to local shopping centers, grocery stores, and popular local restaurants. Its also an Convenient commuting distance to downtown Portland. Don't miss this stunning, value priced and move in ready townhouse!

54 Provost Dr Unit 54, Windham

Listing courtesy of Keller Williams Realty.

$335,000
2 Beds 2 Baths
Take advantage of this limited time 'Fall Special' at $335,000 (regularly $349,900) for one unit only PLUS Builder Incentives Available. Stop paying rent! Own for $2400 per month*! Offering 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 style unit is the largest unit 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 2129, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

$339,900
2 Beds 2 Baths
Welcome to Windham Hill Woods, a well-established and desirable condominium community offering an exceptional combination of convenience, amenities and value. Ideally located on the south side of downtown Windham, this townhouse-style condo provides easy access to shopping, dining and area amenities while helping you avoid much of the traffic congestion found farther north. Inside, the thoughtfully designed floor plan offers comfortable living across three levels. The first floor features a granite kitchen, inviting living room with hardwood flooring, convenient half bath and a sliding glass door leading to your private deck overlooking the wooded edge. Upstairs, you'll find a spacious primary bedroom, second bedroom and full bathroom. Continue to the third-floor loft, an especially versatile space that works beautifully as a home office, reading area, hobby space or flex room. A full basement provides excellent storage and includes the convenience of an in-unit washer and dryer. The $300 monthly association fee includes water and sewer, adding to the overall value and ease of ownership. Windham Hill Woods offers an in-ground pool, pickleball court, sidewalks and generous open space. The association is also pet friendly, making this an inviting community for a variety of lifestyles. Whether you're looking to simplify your lifestyle, make your first home purchase or find a convenient Maine getaway, 23 Meagans Way offers the space, amenities and location to make condo living easy and enjoyable.

23 Meagans Way Unit 12, Windham

Listing courtesy of PO-GO REALTY.

$299,900
1 Beds 1 Baths
**Builder Incentives Available**.Stop paying rent! Own for $2100 per month*! The Highland offers a peaceful retreat designed for simple, modern living. With 766 square feet of thoughtfully designed space, this one-bedroom, one-bathroom residence blends comfort, style, and convenience in a layout that feels both open and inviting. Inside, contemporary finishes meet everyday functionality with granite countertops, stainless steel appliances, and an in-unit washer and dryer. Large windows allow natural light to pour throughout the home, creating a bright and welcoming atmosphere perfect for relaxing or entertaining. Shared amenities include, a gym, co-working space, community room, dog wash, storage lockers and more! Builder incentives available! *Estimated Principal, Interest, Est taxes & PMI; 5 year fixed, 30 year term, 3% down, 6.781% APR, subject to approval.

12 Stillwater Dr Unit 1137, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

$294,000
2 Beds 2 Baths
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 blend of comfort, functionality, and location. Don't miss your opportunity to make this wonderful property your new home!

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

$479,000
3 Beds 3 Baths
New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. 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--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. 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. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With completed units available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from. Common area pavilion and playground, and a short distance to Shaw Park and the Sebago to Sea trail. Pet friendly!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

$469,000
3 Beds 2 Baths
This brand new 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 full bathroom, a functional mudroom entry, and a great back deck. Upstairs includes three bedrooms, and 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. Move right in and make your dream of owning a brand new home come true!

8 Shepherd Ln Unit 4, Windham

Listing courtesy of RE/MAX By The Bay.

$699,000
2 Beds 3 Baths
Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 25 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes provide both first and second floor primary suite options. Multi-generational, Companion, and Guest-Friendly, owners of these units can opt for stacked or side-by-side laundry on one or both floors of living. This inner unit features two full baths, a functionality first open concept kitchen, a front porch and back deck for sipping in the scenic surrounds, 18ft cathedral ceilings, and not one but two bonus spaces, fit for an office, spare bed, hobbying, or entertaining! This unit also has the option to finish its full-daylight walkout basement for an additional 500 SF of living area. Community Amenities to Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the over 50 acre parcel with over 6000 feet of nature trails, more than 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 customize your home's finishes!

25 Daybreak Ln Unit 8, Windham

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

$494,900
3 Beds 2 Baths
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.

$484,000
3 Beds 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. 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--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite 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. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

26 Dolley Farm Rd Unit 12, Windham

Listing courtesy of The Flaherty Group.

$549,000
2 Beds 2 Baths
Some properties sell a house. This one sells a lifestyle. Set on the shores of Sebago Lake with your own boat mooring, sandy beach access, and sweeping views of the water and mountains beyond, this condominium offers four seasons of the good life -- boating and swimming in summer, ice fishing and snowshoeing in winter, and quiet lakefront mornings year-round. Inside, hardwood floors and lake views set the tone in the living room, while the kitchen impresses with bright white beadboard cabinets, granite countertops, and full-sized appliances. Two comfortable bedrooms offer flexible living with a primary suite and a spacious second bedroom with plenty of room for bunks, perfect for guests or a full crew of weekend visitors. Community amenities include tennis, basketball, and pickleball courts and a shared dock, all managed by a rock-solid association that covers nearly everything and hasn't assessed in over ten years. Portland, Windham, and Point Sebago Golf Resort are all minutes away, but once you're here, you won't want to leave.

1112 Roosevelt Trl Unit 16, Windham

Listing courtesy of RE/MAX By The Bay.

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