Windham Homes under $500,000

Welcome to Windham, a hidden gem nestled in the scenic landscapes of New England! Known for its vibrant community spirit and picturesque surroundings, Windham boasts a perfect blend of suburban tranquility and easy access to city life. With its charming downtown area, abundant parks, and excellent schools, it’s no wonder that families and professionals alike are flocking to this enchanting town.

One of the most appealing aspects of Windham is its diverse housing market, particularly for those seeking homes under $500,000. Here, you’ll find a variety of options that cater to different lifestyles and preferences. From cozy single-family homes with lush backyards to modern townhouses featuring contemporary designs, there’s something for everyone. These homes often come equipped with spacious layouts, updated amenities, and proximity to local parks and recreational facilities, making them ideal for families and first-time homebuyers.

Windham’s affordability doesn’t compromise its charm. The community is rich in history, with beautiful colonial architecture and well-maintained neighborhoods that exude warmth and character. Residents enjoy a plethora of outdoor activities, including hiking trails, fishing spots, and community events that foster a strong sense of belonging.

If you’re looking for a home that combines comfort, affordability, and a welcoming community, Windham is the perfect place to start your journey. With its homes under $500,000, you can embark on the next chapter of your life in a town that truly feels like home. Discover the possibilities in Windham today!

Newest Windham Homes under $500,000

$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

$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

$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

$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

$499,000

2 Beds ⋅ 2 Baths ⋅ 5104617 MLS

Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting. Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The clapboard siding remains unfinished, and the lower level walk out basement is plumbed for a third full bathroom, offering additional flexibility for finished living space. A substantial 24' x 48' completed foundation is in place for the planned garage. It will accommodate a 24' x 24' two car garage plus an additional 24' x 24' area of approximately 552 square feet, ready to be finished and purposed according to your needs, ideal for a workshop, studio, storage, recreation space, or other use. The land is equally appealing, with expansive meadows featuring tillable soils formerly used to grow organic fruits and vegetables, established trails, mature woods, and high quality gravel on the property. Adding to the sense of privacy and protected open space, the property abuts a National Wildlife Refuge along its western and northern boundaries. Enjoy gardening, exploring the trails, working on projects, or simply taking in the peaceful Vermont landscape. Conveniently located within reach of Stratton, Magic, and Bromley Mountains and the villages of Londonderry, Chester, and Grafton. An exceptional opportunity to complete a substantial Vermont property and create something truly your own.

5855 Windham Hill Rd, Windham

$375,000

4 Beds ⋅ 2 Baths ⋅ 5099541 MLS

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

715 Chase Rd, Windham

$435,000

2 Beds ⋅ 3 Baths ⋅ 5099010 MLS

20% down will be needed. Welcome to this beautifully maintained townhouse offering the perfect combination of comfort, convenience, and value in the desirable Hardwood Heights community. Step inside to an inviting open-concept main level featuring a spacious living room, dining area, and updated kitchen, ideal for both everyday living and entertaining. Just off the kitchen, enjoy your private back deck, perfect for grilling or relaxing outdoors. The first floor also offers the convenience of a laundry area, a charming front porch, and an attached one-car garage. Upstairs, you'll find two generously sized bedrooms. The primary suite features its own private ensuite bath with double closets and private deck. There is also a versatile loft space that's perfect for a home office, fitness area, nursery, reading nook, or additional living space. The second bedroom features a 3/4 ensuite bath. The finished walk-out lower level expands your living area and opens to a private patio overlooking a peaceful wooded backyard, providing the perfect setting to unwind. Additional highlights include forced hot air, central air conditioning, a renovated kitchen, a new water heater, and numerous other updates throughout. Residents of Hardwood Heights enjoy low-maintenance living with community amenities including tennis courts, lawn care, snow removal, and trash service. Conveniently located near shopping, restaurants, major commuting routes, and highly regarded schools, this home truly has it all.

49 Stacey Cir, Windham

$429,900

2 Beds ⋅ 1 Baths ⋅ 5091573 MLS

Your Dream Lake Escape on Shadow Lake Awaits! Seize this incredible opportunity to create a custom retreat on the highly desirable Shadow Lake. Offering 46 feet of private water frontage on the serene north side, this end-of-the-road lot is an absolute gem. A beautiful babbling brook runs down the property, enhancing the tranquil setting. Whether you choose to renovate the existing structure or completely tear down and build new, the path is clear: all state plans are already approved and available! Town permit has expired and needs approvals, but all plans will be shared. Enjoy the privacy of a large lot that abuts state land and provides plenty of parking. This peaceful waterfront location is also a commuter's dream, only 45 minutes from Boston and conveniently close to Salem's vibrant shopping, restaurants, and the Tuscan Village area. Property sold AS IS. Buyers must be accompanied by their agent and enter the existing structure at their own risk.

5 Allen Rd, Windham

$225,000

2 Beds ⋅ 1 Baths ⋅ 5085393 MLS

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Home will need a new septic system. If you have been looking for a true Vermont getaway, this property delivers!

51 Golding Rd, Windham

$299,000

1 Beds ⋅ 1 Baths ⋅ 5083456 MLS

**ACCEPTING BACKUP OFFERS; SHOWINGS STILL AVAILABLE. Rare opportunity to own your own private retreat just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond in Windham, NH. Set on a generous half-acre lot, this charming one-room seasonal camp offers a unique chance to enjoy the outdoors and create your own getaway in a peaceful, natural setting. Surrounded by trees and open space, the property provides a sense of privacy while still being part of a lakeside community. Whether you’re looking for a weekend escape, a summer retreat, or a place to build future plans, the possibilities here are compelling. An outhouse is located on site, and the property is serviced by private water. Spend your days swimming, kayaking, fishing, or simply relaxing by the water at nearby Cobbetts Pond, known for its scenic beauty and recreational appeal. Located in desirable Windham, residents enjoy a balance of quiet living and convenience, with access to highly regarded schools, local shops, dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a unique chance to secure a slice of the Cobbetts Pond lifestyle with space, privacy, and potential. Photos may be digitally enhanced.

10 First St, Windham

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