Windham Homes under $750,000

Welcome to Windham, a charming town nestled in the picturesque landscapes of southern Maine! Known for its stunning natural beauty and vibrant community spirit, Windham offers a perfect blend of suburban tranquility and easy access to urban conveniences. With its serene lakes, lush parks, and abundant outdoor activities, this town is a haven for nature lovers and adventure seekers alike. Whether you’re hiking the scenic trails of the nearby Sebago Lake State Park or enjoying a leisurely day of fishing on one of Windham's pristine lakes, the opportunities for recreation are endless.

For those looking to make Windham their home, you'll find a wonderful selection of properties available under $750,000. From cozy single-family homes to charming townhouses, there’s something to suit every taste and lifestyle. Many of these homes boast modern amenities, spacious yards, and beautiful views, all while being just a short drive from the bustling city of Portland. Families will appreciate the highly-rated schools and community-oriented atmosphere, making Windham an ideal place to raise children.

Real estate in Windham is not just about finding a house; it’s about discovering a lifestyle. Imagine sipping your morning coffee on a sun-drenched porch or hosting summer barbecues in your expansive backyard. With an active community calendar filled with events and activities, you’ll quickly find yourself becoming part of the fabric of this welcoming town. Explore the possibilities in Windham, where your dream home awaits!

Newest Windham Homes under $750,000

$575,000

3 Beds ⋅ 1 Baths ⋅ 5113081 MLS

Exceptional value and Location in Windham! Full of character, history, and potential, this distinctive 3-bedroom, 3/4-bath home dating to 1810 offers a unique opportunity to own a property that simply cannot be replicated. The updated kitchen and bathroom creates a blend of historic charm and a more modern living space. Set on .75 acres, the property is home to beautiful established perennial gardens and offers a wonderfully private backyard with a large patio. Its an inviting setting for outdoor entertaining, summer gatherings, gardening, or simply enjoying your own peaceful retreat. Location is a standout feature: Walk to the Windham Town Beach and Rogers Field, and only a short two mile trip to all 4 public schools and the Clyde Pond walking trails. The current owners-of over 30 years have made several thoughtful updates including: full kitchen remodel (2019), bathroom remodel (2022), new furnace (2025), and blown in basement insulation (2026), and too many more to list (see attached file in listing docs). These improvements provide a solid foundation while leaving plenty of opportunity for the next owner to bring their own vision and design ideas. Whether you are drawn to the charm of an early 19th-century home, the privacy of the landscaped grounds, or the opportunity to create something truly special, this property offers a rare combination of history, location, updates, and potential. Come see the possibilities and imagine what you can make of this one-of-a-kind property! One upstairs bedroom does not have a closet. Full list of updates/FAQs in the listing documents.

22 Cobbetts Pond Rd, Windham

$469,900

2 Beds ⋅ 2 Baths ⋅ 5112738 MLS

Welcome to 21 Braemar Road in Braemar Woods, a smaller, established condominium community in desirable Windham, NH. This extensively renovated 2-bedroom, 1.5-bath townhome offers approximately 1,517 square feet of bright, move-in-ready living space. The main level features new luxury vinyl plank flooring, updated trim, doors, lighting and fixtures throughout. The completely renovated kitchen showcases quartz countertops, stainless steel appliances, tile backsplash, two-tone cabinetry and generous workspace. The adjoining living room offers abundant natural light and a new electric fireplace. A renovated half bath with first-floor laundry adds everyday convenience. Upstairs are two spacious bedrooms, including a bedroom with a versatile loft area, along with a beautifully renovated full bathroom featuring a double vanity, lighted medicine cabinet and updated tub and shower. Major improvements include an efficient Mitsubishi heat-pump heating and cooling system, new hot-water system, updated electrical equipment and a new composite deck. Additional features include an unfinished basement, attached one-stall garage, extra parking and included washer, dryer and all new kitchen appliances. Braemar Woods has no age restriction, and pets are permitted subject to association bylaws. The monthly condominium fee is $490. Conveniently located near shopping, dining, commuter routes and area amenities. Quick closing available.

21 Braemar Rd, Windham

$465,000

2 Beds ⋅ 3 Baths ⋅ 5112487 MLS

Enjoy the ease of first-floor living in this beautifully maintained townhouse located in a sought-after 55+ community in Windham. Thoughtfully designed with comfort and convenience in mind, this home offers an open-concept floor plan, soaring vaulted ceilings, a private primary suite, and inviting sun-filled living spaces that make everyday living feel effortless. The open-concept kitchen flows seamlessly into the living room, creating the perfect space for entertaining. The private first-floor primary suite overlooks the backyard and features a spacious attached bath with a walk-in shower, creating a peaceful retreat. A versatile bonus room provides additional living space and leads to a sunroom, perfect for enjoying your morning coffee or unwinding with a good book. Step outside to the private deck and take in the tranquil surroundings. Convenient first-floor laundry and a half bath add to the home's practicality, while the attached one-car garage offers easy access and additional storage. Upstairs, you'll find a generous loft second bedroom, a full bath, and an oversized walk-in closet, making it an ideal space for guests or hobbies. The unfinished basement provides endless possibilities for storage, a workshop, home gym, or future expansion. Enjoy the benefits of a low HOA fee and access to the community clubhouse, all while being conveniently located near Windham's shopping, dining, and commuter routes. Comfort, convenience, and community await. Don't miss this exceptional opportunity!

33 Brookview Rd, Windham

$439,000

2 Beds ⋅ 3 Baths ⋅ 5112368 MLS

Welcome home to Whispering Winds, one of Windham’s premier 55+ active adult communities! Situated at 59 Pleasant St, this stunning mid-unit condo offers a thoughtful floor plan designed for effortless, one-level living paired with incredible bonus space. Step inside to an airy layout featuring soaring cathedral ceilings and rich hardwood flooring. The main living area flows seamlessly into a bright kitchen and comfortable dining area, leading out to your private backyard patio—perfect for morning coffee or outdoor relaxation. The main level offers convenience with a primary suite, full bathroom, and central air conditioning powered by efficient gas heat. Upstairs, you'll find a versatile loft area alongside additional living space ideal for a second bedroom, home office, or guest suite. Key Features & Highlights: * Spacious Living: 1,522 sq. ft. of above-grade living area across 1.5 stories with 4 rooms, 2 full bathrooms, and 1 half bath. * Bonus Space: Includes a partially finished basement for extra rec space or storage, plus an attached garage and a charming wood deck/patio. * Modern Comforts: Central A/C, forced air gas heating, and low-maintenance community utilities. * Prime Location: Peaceful setting within a highly desirable, well-maintained neighborhood. Don't miss the opportunity to enjoy relaxed, low-maintenance condo living at its finest!

59 Pleasant St, Windham

$599,000

5 Beds ⋅ 4 Baths ⋅ 5111512 MLS

Have it all on Timber Ridge! This spacious Windham colonial offers four bedrooms in the main house plus a recently renovated one bedroom accessory dwelling unit on the lower level, creating valuable flexibility and rental potential. Set in the mountains, the home welcomes you with a covered front porch and attached two car garage, making four season living that much easier. Inside, a dramatic multi story foyer with floor to ceiling window opens to warm wood floors and a comfortable layout with plenty of room to gather. The kitchen features a breakfast bar island and ample cabinetry, flowing into the dining area and out to the back deck, which was replaced last year. Upstairs, the primary suite includes a private bath and large walk in closet, with two additional bedrooms and a shared full bath nearby. The walk out lower level accessory dwelling unit has been recently renovated and includes its own kitchen, living and dining space, oversized bedroom, and full bath. Radiant in floor heat serves the main and lower levels, while newer heat pumps provide instant, efficient heating and cooling. Whether you are looking for a full time home or a Vermont getaway, this property offers the space, flexibility, and mountain setting to enjoy Southern Vermont in every season. Upstairs, the primary suite includes a private bath and large walk in closet, with additional bedrooms and a shared full bath nearby. The walk out lower level offers even more flexibility with a separate apartment featuring its own kitchen, living and dining space, oversized bedroom, and full bath. Radiant in floor heat on the main and lower levels adds comfort throughout, with mini splits offering efficient ancillary heating and air conditioning in the warmer months. Whether you are looking for a full time home or a Vermont escape, this is a place to spread out, settle in, and enjoy mountain living in every season.

71 Lower Birch Cir, Windham

$650,000

2 Beds ⋅ 3 Baths ⋅ 5111390 MLS

Welcome to The Willows! Enjoy the ease of low-maintenance living in this beautifully appointed 2-bedroom, 2½-bath detached condominium in a desirable 55+ community. This inviting home offers a comfortable, easy-flowing floor plan with thoughtfully designed spaces for everyday living and entertaining. The eat-in kitchen features granite countertops and opens directly to the screened-in porch, creating a wonderful extension of the living space and the perfect setting for morning coffee, casual dining, or relaxing with friends. The screened porch lets you enjoy the outdoors in comfort throughout the seasons. Two spacious bedrooms provide plenty of privacy, while a versatile additional room offers the flexibility to use as a home office, study, den, or hobby room. A one-car garage provides convenient parking and additional storage. At The Willows, enjoy the privacy of a detached home with the ease and convenience of condominium living. Whether you're looking to downsize, simplify, or simply enjoy more time doing the things you love, this home offers the perfect combination of comfort, flexibility, and low-maintenance living in a welcoming 55+ community. Showings start Sunday 9/27.

20 Addison Rd, Windham

$299,900

2 Beds ⋅ 1 Baths ⋅ 5111290 MLS

BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

17 First St, Windham

$585,000

3 Beds ⋅ 2 Baths ⋅ 5110086 MLS

Welcome home to this 3 bedroom expanded cape, offering a flexible layout with the convenience of primarily one-level living. The bedrooms, bathrooms, main living areas and laundry are all located on the same floor, including a spacious primary suite with a walk-in closet and private en suite bath. The primary and second bedrooms were part of a major addition completed just five years ago, adding both space and functionality to the home. Downstairs, you’ll find a 2-car garage underneath, a dedicated home office and tons of additional storage space. Out back, enjoy a deck overlooking the private backyard, complete with a greenhouse for gardening enthusiasts. This home also features OWNED solar panels, helping to offset electricity usage. With plenty of space, a practical layout and a great commuter location in desirable Windham, this home is ready for its next owners! Private showings begin immediately.

17 Bridle Bridge Rd, Windham

$749,900

4 Beds ⋅ 3 Baths ⋅ 5109291 MLS

Welcome to a truly unforgettable property where amazing grounds, winding stone pathways, a koi pond with cascading waterfall, and an in-ground pool create the setting for a spectacular private retreat. 34 Sharon Road is a one-of-a-kind Garrison offering remarkable craftsmanship, an enchanting garden setting, and incredible potential for its next chapter. Set among mature trees and extensive stonework, this 4 bedrooms, 2.5 baths home offers 2,780 sq. ft. of official living area, plus a four-season greenhouse and striking Hartford conservatory. Inside, hardwood floors and exceptional custom trim create warmth and character throughout. The showstopping family room features a soaring vaulted ceiling, dramatic exposed beams, rich wood detailing, and an impressive floor-to-ceiling brick fireplace. The custom kitchen includes maple cabinetry, granite countertops, a center island, and two ranges—including a professional-grade Viking range with matching hood. Generous living and entertaining spaces provide a flexible layout ready to be reimagined. All four bedrooms are located upstairs, including a primary suite with its own en-suite bathroom. The unfinished lower level offers lots of potential, including a spacious work area, loads of storage, and access to a two-car garage. Whether used for hobbies, projects, recreation, or additional storage, this lower level provides valuable flexibility. The Asian-inspired gardens and water features make the outdoor setting truly special. The distinctive conservatory and four-season greenhouse with built-in heat lines offer exciting possibilities for gardeners, artists, or anyone dreaming of a truly unique sanctuary. The home and grounds require work and have deferred maintenance. Property is being sold as-is. Bring your creativity and unlock the full potential of this hidden Windham gem! Come visit the Open House 9/12 (Sat) and 9/13 (Sun) from 1:30PM-3:00PM

34 Sharon Rd, Windham

$399,000

2 Beds ⋅ 3 Baths ⋅ 5109111 MLS

Welcome to this desirable townhouse in popular Windham, NH, offering an ideal blend of space, flexibility and value with no age restrictions and pets allowed. The main level features a comfortable family room with fireplace, dining area and kitchen, creating an easy layout for everyday living and entertaining. A convenient half bath with laundry completes the first floor. Upstairs, the spacious primary bedroom suite includes a bonus loft area that can easily serve as a home office, reading nook, craft space or whatever fits your lifestyle. The second bedroom offers the added convenience of its own private bath, making it perfect for guests. Need even more space? The basement offers two additional bonus rooms with endless possibilities for a home gym, office, hobby room, playroom or media space. An attached one car garage, central air and a condo fee that includes water, sewer, trash, snow removal and lawn care add to the convenience. The home could use some fresh paint and new carpet, giving you the opportunity to add your own personal touches and make it truly yours. Priced with this in mind, there is excellent potential to build instant equity, and the seller is offering a concession toward painting to help get you started. Bring your vision and take advantage of this opportunity to own a home in one of Windham’s sought after communities! Welcome Home!

61 Stacey Cir, Windham

$569,000

6 Beds ⋅ 5 Baths ⋅ 5108718 MLS

Set on a scenic country property in Windham, this expansive home offers exceptional space, flexibility and a setting with real character. Currently used as a large single-family residence, the home was originally built as a three-family property, with a common entrance serving two living areas and a separate entrance to the garden-level apartment. A central stairwell can connect the spaces, creating options for a large household, multi-generational living, guests, home offices or future reconfiguration. The three living areas include full kitchens, generous living rooms and a total of six bedrooms, with expansive rooms and large windows throughout. There is also ample storage and flexible space for a workshop, studio or dedicated home office. The grounds are where this property becomes especially memorable. Shaped over the years by an artist’s eye and a love of the land, the organic gardens feel established, abundant and wonderfully personal, with fruit trees, flowering shrubs, mature plantings and productive raised beds built at waist height. Several decks and screened porches invite you to slow down and take in the setting, while the property unfolds into a pond, large meadow, playing field, trout stream and walking trails, with views toward Turkey Mountain Ridge. There is a quiet, almost timeless quality here that is increasingly hard to find. Located off the beaten path in picturesque Windham, yet convenient to Southern Vermont skiing, hiking and year-round recreation, the property offers room to live, create, gather and breathe. The home does need TLC and updating, but its scale, versatile layout, organic gardens, land and natural setting make it a true diamond in the rough with tremendous potential.

1113 Old Cheney Rd, Windham

$499,000

3 Beds ⋅ 2 Baths ⋅ 5108371 MLS

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Open House on September 26, 10am -12:00 Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

756 Birch Hill Rd, Windham

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