Windham Real Estate

Welcome to Windham, New Hampshire – a hidden gem nestled in the heart of Rockingham County! This picturesque town combines the charm of small-town living with the convenience of proximity to major urban centers, making it an ideal place for families, professionals, and nature enthusiasts alike.

Windham boasts a rich history, reflected in its quaint New England architecture and the vibrant community spirit that resonates throughout its neighborhoods. With a population of just over 14,000 residents, this close-knit community prides itself on its excellent schools, ensuring that families have access to top-notch education. The town's commitment to maintaining a family-friendly atmosphere is evident in its many parks, recreational facilities, and community events that bring residents together.

Nature lovers will find Windham particularly appealing, as the town is surrounded by stunning landscapes and outdoor activities. The serene Canobie Lake Park offers a perfect spot for boating and picnicking, while the Windham Town Forest provides miles of scenic trails for hiking, biking, and wildlife observation. For those who enjoy winter sports, nearby ski resorts and snowshoeing trails make it easy to embrace the beauty of the changing seasons.

Conveniently located just 30 miles north of Boston, Windham offers easy access to urban amenities while maintaining its tranquil, suburban charm. With a variety of local shops, restaurants, and cultural attractions, residents can enjoy a vibrant lifestyle without sacrificing the peacefulness of rural living.

Whether you’re looking to buy your first home, downsize, or invest in a property, Windham, NH, presents an exceptional opportunity to experience the best of New England living. Discover your dream home in this enchanting town today!

Newest Listings in Windham

$599,000

3 Beds ⋅ 2 Baths ⋅ 5108856 MLS

Set on 1.84 acres in a desirable Windham location, this 3-bedroom, 2-bath split-level offers space, privacy, and plenty of potential to make it your own. Tucked away on a dead-end road and situated across from a former apple farm, the property enjoys a peaceful setting while still being convenient to everything Windham has to offer. An added bonus is direct access to the rail trail right from the property, perfect for walking, biking, and enjoying the outdoors. Inside, hardwood flooring runs throughout much of the main level, while a spacious sunroom and wood-burning stove add warmth and character. Step outside onto the deck overlooking the private backyard, offering a wonderful setting to relax, entertain, or simply enjoy the surrounding natural landscape. The finished lower level provides additional living space with flexibility for a family room, home office, gym, or more, and a two-car garage offers added convenience and storage. Ready for your personal touches and updates, this home presents an exciting opportunity to create something truly your own in one of Windham’s most desirable communities. With nearly two acres, a peaceful setting, and a versatile layout, there is so much potential to make this property shine.

36 Governor Dinsmore Rd, Windham

$2,800,000

4 Beds ⋅ 6 Baths ⋅ 73573663 MLS

UNFORGETTABLE LUXURY | Distinctive, sophisticated and designed to leave a lasting impression, this exceptional custom Colonial by renowned builderDiPietro Homes offers 6,000+ sq. ft. of beautifully appointed living space. Thoughtfully enhanced with on-trend updates and improvements, this remarkable home blendsexceptional craftsmanship with a fresh, elevated style for today's luxury lifestyle. From the moment you enter, custom millwork and impressive architectural details setthis home apart. At the heart of the home, the stunning family room features a coffered ceiling and wood-burning fireplace, opening seamlessly to a showstopping chef'skitchen designed for both everyday living and effortless entertaining. Full-size refrigerator and freezer, generous workspace and a Butler's Pantry complement thisthoughtfully designed space. An elegant dining room, private office and functional mudroom complete the main level. Upstairs, the luxurious primary suite is anunforgettable retreat with its own fireplace and spa-inspired bath featuring a soaking tub and steam shower. With 4 bedrooms, 5 bathrooms, a bonus room and afinished lower level offering a recreation room, full kitchen, built-ins and bath, there is exceptional space and versatility throughout. Outside, your private backyard awaits, complete with an in-ground saltwater pool with waterfall and a covered seating area perfect for relaxing, entertaining and enjoying summer days outdoors. Convenientlylocated near I-93, schools, shopping and community amenities, with Boston approximately 45 minutes away. A truly unforgettable home where luxury, comfort andexceptional design come together.

17 Bennington Rd, Windham

$884,900

2 Beds ⋅ 3 Baths ⋅ 5108741 MLS

Introducing an exceptional new luxury duplex community in one of Windham's most desirable locations. Thoughtfully designed for today's lifestyle, these stunning new homes combine modern elegance, quality craftsmanship, and energy-conscious construction to create the perfect balance of comfort, style, and convenience. Step inside and discover bright, open living spaces enhanced by soaring ceilings, oversized windows, and carefully curated finishes throughout. The heart of each home features a beautifully appointed kitchen with quartz countertops, stylish accents, and seamless flow into the spacious living area, where a cozy fireplace creates the perfect gathering place for family and friends. Designed with flexibility in mind, these homes offer versatile living areas and multipurpose flex spaces to accommodate work, hobbies, guests, or changing lifestyle needs. Enjoy effortless indoor-outdoor living with a welcoming covered front porch and a private patio or deck for relaxing and entertaining. Upstairs, retreat to a luxurious primary suite featuring dual vanities, a custom tiled shower with glass enclosure, and two generous walk-in closets. A second bedroom, full bath, expansive loft, and convenient second-floor laundry provide both comfort and functionality. Additional features include a two-car garage, full unfinished basement offering future expansion potential, and several green-building features designed to help reduce energy costs while supporting a low-maintenance, executive lifestyle. Ideally situated near major highways, shopping, dining, recreation, nature trails, and Windham's highly regarded schools, this exciting new community offers the perfect combination of luxury, convenience, and modern living. *** This is a construction site and for your safety it is shown by appointment ONLY (or at the scheduled open house) *** GPS 47 North Lowell Rd.

5 Campbell Way Unit 2, Windham

$1,100,000

2 Beds ⋅ 3 Baths ⋅ 5108732 MLS

Rarely does an opportunity come along to own a brand-new home in such a desirable lakefront setting. Set on a peaceful road overlooking beautiful Cobbetts Pond, this property combines privacy, natural beauty, and access to one of Windham’s most sought-after recreational communities. With zoning variances and approvals in place and construction well underway, this thoughtfully designed year-round residence is already framed and approaching the sheetrock stage, with anticipated completion by the end of October. The home features two bedrooms, two full bathrooms, and three levels of living space. Both bedrooms have balcony access, creating a peaceful retreat to relax and enjoy the tranquil water views. The main level also offers a walk-out deck, providing an inviting outdoor space to take in the beautiful lake surroundings. The walk-out lower level adds valuable living space and flexibility, while the elevated setting allows the home to capture the beauty of its surroundings. Deeded beach rights and water access provide the opportunity to enjoy all that Cobbetts Pond has to offer, from summer days on the water to quiet evenings overlooking the lake. Ideally situated for both relaxation and convenience, this private lakeside setting remains within easy reach of major highways, Boston, Tuscan Village, airports, and area schools. This is a rare opportunity to own a distinctive, brand-new residence in one of Windham’s premier lake communities, with the construction already underway and the vision becoming a reality.

14 Second St, 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. 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

$775,000

3 Beds ⋅ 3 Baths ⋅ 5108121 MLS

OFFER DEADLINE TUESDAY 9/8 4:00pm. Gorgeous custom cape set in a beautiful cul-de-sac neighborhood, with easy access to I-93 at exit 3. You’re sure to appreciate that the home is set back on a professionally landscaped lot. The entrance opens to the formal dining room, with hardwoods and vaulted ceiling with skylights, all opening to a balcony. Enjoy the gorgeous custom kitchen, with big center island, granite counters and stainless-steel appliances. A vaulted ceiling living room is located off the front foyer. The office/den opens to a dramatic two-story solarium, with handsome wood ceilings, taking in the views of surrounding woodlands. The family room is open to the kitchen and features hardwood floors and a stone fireplace. Tucked privately off the dining room is a beautiful sunroom, featuring the warmth of wood walls, with vaulted ceiling and skylights. Completing the first floor is a powder room with an elegant vanity and a laundry area. The second-floor features three bedrooms with lovely updated baths. The spacious primary suite features a brand-new private, 3/4 bath. The interior is all freshly painted and new carpeting in bedrooms. The walk-out lower level features a huge gathering room with daylight windows, and sliders to the patio. The mudroom offers direct access to two-car garage. The outdoor living space has a wonderful patio area and a huge deck. You will also find raised beds for your gardening needs. This home has a warm and inviting appeal with dramatic cotemporary features. Don’t hesitate… this is an excellent value in sought after Windham NH.

38 Sharon Rd, Windham

$695,000

3 Beds ⋅ 3 Baths ⋅ 5107952 MLS

Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus room provides valuable flexibility for a home office, guest space, playroom, or den. An attached two-car garage makes Vermont living especially convenient, providing sheltered parking along with plenty of room for skis, bikes, outdoor gear, and storage. Outside, the yard offers space to relax, play, garden, or entertain, while the firepit creates the perfect gathering spot for summer evenings, crisp fall nights, and après-ski get-togethers. Located in the quiet mountain community of Windham, this property puts four-season recreation within easy reach. Five major ski areas—Stratton, Bromley, Magic Mountain, Okemo, and Mount Snow—are all located within approximately 35 miles of town, providing an incredible variety of winter adventures. When the snow melts, explore nearby hiking and biking trails, enjoy fishing, paddling and swimming, or spend the day at destinations such as Lowell Lake and Jamaica State Parks. The greater Windham region is known for its extensive trail network and abundant opportunities for hiking, mountain biking, snowshoeing, cross-country skiing, and snowmobiling. Whether you're searching for a full-time Vermont residence or a low-maintenance mountain getaway, this newly built home offers a wonderful combination of modern comfort, outdoor space, and access to everything that makes Southern Vermont special.

717 Horsenail Hill Rd, Windham

$1,275,000

4 Beds ⋅ 3 Baths ⋅ 5107896 MLS

Welcome to this exceptional 4-bedroom, 3-bath home, built in 2006 and ideally situated on a 1.10-acre corner lot in Windham’s highly sought-after Spruce Pond neighborhood. Offering elegant finishes, soaring ceilings, hardwood floors, a fully fenced yard, and a standby generator, this impressive property blends style, comfort, and everyday functionality. A grand foyer sets the tone for the beautifully designed spaces beyond. At the heart of the first floor is a stunning kitchen featuring detailed cabinetry, a distinctive wood ceiling, and an expansive granite island. The kitchen flows seamlessly into the dining area and dramatic living room, where 20-foot ceilings and a wood-burning fireplace create an unforgettable setting for entertaining or relaxing at home. Pet owners will appreciate the thoughtfully designed dog room, complete with space for crates and a convenient dog door providing direct access to the fenced yard. Upstairs, the spacious primary suite offers two closets and a luxurious bath with a tiled shower and separate soaking tub. Three additional generously sized bedrooms, a full bath, and a dedicated laundry room complete the second level. The expansive unfinished lower level features high ceilings and presents an exceptional opportunity to create additional living and entertaining space tailored to your lifestyle. Envision a sophisticated home theater, game room, fitness studio, wine cellar, or private retreat- the possibilities are truly endless. Outside, the inviting backyard includes a separate fenced area for dogs and plenty of room for a future pool, playset, or other outdoor amenities. Located in a desirable community known for Windham’s exceptional school system, this beautifully maintained home is a must-see. Open House Sunday, Sept. 13th 12-2pm.

3 Duston Rd, Windham

$665,000

2 Beds ⋅ 3 Baths ⋅ 5107469 MLS

OPEN HOUSES CANCELLED Beautifully maintained and privately situated at the top of The Villages at Windham, this open-concept condominium offers comfortable one-level living in one of the community’s most desirable locations. Set on a quiet cul-de-sac and abutting conservation land, the home enjoys an exceptional sense of privacy, space, and connection to nature. The main level features a welcoming flow between the kitchen, dining, and living areas, highlighted by a gas fireplace and a composite deck conveniently located off the kitchen. Two bedrooms, an updated primary bathroom, first-floor laundry, and central air make everyday living exceptionally comfortable and convenient. A spacious finished daylight lower level offers outstanding flexibility for a family room, home office, guest accommodations, gym, or hobby space and includes daylight windows, a three-quarter bath, and a walkout slider to the outdoors. Additional highlights include a recently installed standby generator and a two-car garage with polyurea flooring offering a lifetime transferrable warranty to the new owner. The Villages at Windham offers an active neighborhood atmosphere, excellent walkability, and a picturesque community pond. Best of all, this is not an age-restricted community, making it a rare opportunity to enjoy low-maintenance living, privacy, flexibility, and space in a premier Windham location. Join us at the first Open House Wednesday 9/2/26 from 4:00- 6:00 PM

60 Gordon Mountain Rd, Windham

$799,900

3 Beds ⋅ 3 Baths ⋅ 5107088 MLS

Location, location… did I mention location? Set on 1.5 acres in a peaceful neighborhood, this comfortable and versatile three-bedroom, three-bathroom home is part of the sought-after Windham school district and offers an easy commute, with Boston less than an hour away. Step inside to a spacious, living room flooded with natural light and anchored by an oversized brick fireplace, perfect for cozy autumn evenings. Just off of the living room, you’ll find an office or bonus room ready to suit your needs. The updated eat-in kitchen features stainless steel appliances, generous cabinetry, and peninsula seating - ideal for casual meals, morning coffee, or gathering with friends. A dedicated dining area with a slider provides easy access to the wraparound back deck. Upstairs, the primary bedroom includes a private bathroom, along with two additional bedrooms and a full bathroom. Newer luxury vinyl plank flooring flows throughout the home. Downstairs, an expansive lower-level room with impressive ceiling height offers endless possibilities for a family room, home theater, gym, playroom or combination of uses. Outside, the generous lot offers privacy, and room to play. Newer roof! Come discover the space, versatility, and location that make this property such a special place to call home!

7 Twin St, Windham

$799,900

5107072 MLS

WATERFRONT OPPORTUNITY on Cobbetts Pond in desirable Windham! Discover the potential of 8 Cross Street, ideally positioned to enjoy the lifestyle and recreation that make this area so special. Whether you're looking for a private retreat, investment opportunity, or the chance to create something entirely your own, this property offers tremendous possibilities. Imagine waking up just steps from the water and spending summer days boating, jet skiing, swimming, fishing and kayaking on beautiful Cobbetts Pond. The nearby town beach is just around the corner, offering even more access to the water and outdoor recreation. For those looking to think bigger, ther is an opportunity to acquire the neighboring property at 6 Cross Street and explore combining the parcels for a larger homesite, custom dream home or potential family compound, subject to Town of Windham approvals, zoning, permitting and all applicable regulations. Windham offers an ideal Southern New Hampshire location with top-rated schools, a highly desirable residential community, and convenient access to I-93. Enjoy nearby parks, trails, restaurants and shopping, while Tuscan Village in neighboring Salem provides premier shopping, dining, entertainment and additional amenities. Waterfront living, recreational opportunities, future potential and an outstanding Southern New Hampshire location come together at 8 Cross Street. Bring your vision and explore the possibilities. Buyers to conduct their own due diligence regarding development potential, lot combination, permitted uses, building plans and all required Town approvals.

8 Cross St, Windham

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