Windham Real Estate

Welcome to Windham, a picturesque town nestled in the heart of New England. Known for its charming landscapes and tight-knit community, Windham offers the perfect blend of small-town charm and modern conveniences. With a rich history dating back to the 18th century, this vibrant city is a treasure trove of cultural heritage and natural beauty.

Windham boasts an impressive array of outdoor activities, making it a haven for nature enthusiasts. The town is surrounded by lush forests, serene lakes, and scenic trails, perfect for hiking, biking, and fishing. Whether you’re exploring the breathtaking views at Windham Mountain or enjoying a leisurely afternoon at one of the local parks, the great outdoors is always just a stone's throw away.

For families, Windham is an ideal place to call home. The town is served by reputable schools and offers a variety of community programs that foster a sense of belonging. The friendly atmosphere is palpable, with local events and farmers' markets that bring residents together throughout the year.

Culturally, Windham is vibrant and diverse. From art galleries to live music venues, there’s always something happening in town. The local dining scene is equally inviting, featuring everything from cozy cafes to gourmet restaurants that celebrate the flavors of New England.

With its perfect blend of history, community spirit, and natural beauty, Windham is not just a place to live; it’s a place to thrive. Discover the charm of Windham and find your dream home in this captivating town today!

Newest Listings in 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

$799,900

3 Beds ⋅ 1 Baths ⋅ 5107071 MLS

Rare opportunity to create your own vision in desirable Windham, NH! Enjoy the small 3-bedroom, 1-bath cottage as a summer getaway or use the property as the foundation for your future building plans. The value here is truly in the land and the incredible waterfront setting. This property offers the potential to acquire an adjoining parcel in one of the area's most sought-after waterfront settings on Cobbetts Pond. Pair this property with the neighboring parcel at 6 Cross St and explore the possibility of creating an exceptional combined property for a custom dream home or potentially a private family compound, subject to Town of Windham approvals and all applicable zoning, permitting and regulatory requirements. Cobbetts Pond offers approximately 302 acres water for swimming, boating, jet skiing, fishing and summer recreation. The town beach is conveniently located just around the corner, adding another wonderful option for enjoying the water and outdoors. Enjoy the tranquility of this special setting while remaining conveniently close to Griffin Park, walking trails, local shops, restaurants and I-93. Windham offers an attractive Southern New Hampshire lifestyle, a strong sense of community and a highly regarded school system. Nearby Tuscan Village in Salem provides additional shopping, dining, entertainment and conveniences. Whether you're looking to secure additional land, create a larger private retreat, or explore future development possibilities, this is an opportunity worth investigating. Buyers should conduct their own due diligence regarding permitted uses, lot combination, access, building potential and all Town approvals. Bring your vision and explore the possibilities of creating something truly special in Windham!

6 Cross St, Windham

$1,140,000

4 Beds ⋅ 3 Baths ⋅ 5106972 MLS

PRIVACY, SPACE & EXCEPTIONAL LIVING ON 2.57 ACRES IN WINDHAM. Set on beautifully landscaped grounds, this impressive residence offers a rare combination of substantial living space, and incredible versatility in one of Windham’s most desirable communities. Offering 4 Levels of living space, 11 rooms, 4 bedrooms, 2½ baths, and an oversized two-car garage. Designed for today’s lifestyle, the main level features an open, inviting floor plan with a spacious kitchen at the heart of the home and generous fireplace living and family rooms that flow beautifully for everyday living and entertaining, including a sunroom that leads to an oversized deck. Upstairs, the spacious primary suite offers two closets and a private en-suite bath complete with a jetted tub and walk-in shower. An expansive open bonus area creates unexpected additional living space and can easily accommodate a home office, fitness area, music or study space, or a comfortable second-floor retreat plus 2 more bedrooms & bath. The walk-up third floor offers yet another space currently used as an oversized bedroom and lounge/pool table area. The oversized finished basement, with heat and A/C in separate zones, provides even more flexibility for recreation, media, home offices, or additional living space, plus a separate laundry area and abundant storage. Extensive improvements include PEX plumbing for hot and cold water, updated electrical wiring, replacement windows, recessed lighting, zoned heating and central air conditioning, along with energy-efficiency upgrades. Relax in the outdoor sun-dance hot tub, enjoy the peaceful surroundings, and experience a property that feels like a private retreat with an oversized deck, fire pit area, large shed, and beautiful yard. Windham schools; close to Tuscan Village, a Windham community that loves involvement if you want. Minutes to shopping and highways.

1 Telo Rd, Windham

$759,900

4 Beds ⋅ 2 Baths ⋅ 5106941 MLS

Welcome to 13 Patricia Street! This well-cared-for home is ready for the next family to create their family memories. This home has great curb appeal, ready and welcoming. Beautiful hardwood floors on the second level in all bedrooms. Spacious living area on the main floor with an enclosed three-season area for morning coffee! An updated kitchen that looks out to the beautiful in-ground swimming pool and jacuzzi hot tub to relax. Grounds feature an irrigation system that has kept the lawn green. Lots of natural lighting in the kitchen with skylights and plenty of cabinet space. This family home will not last long.

13 Patricia St, Windham

$1,600,000

3 Beds ⋅ 3 Baths ⋅ 5106815 MLS

Welcome to 6 Rosewood Street, a beautifully maintained 3–4 bedroom home with a desirable in-law suite! An amazing 30x40’ detached 2 car garage, with 14’ doors, and attached 3 car, with 8’ doors. This home has quality, craftsmanship, and thoughtful details that are often hard to find. This exceptional home features high-end materials, quality finishes, and a level of care that is evident throughout. Designed for one-level living, the home offers an inviting and functional layout with the flexibility to meet a variety of needs. A stunning see-through gas fireplace creates a warm and elegant focal point, adding ambiance and character to the living spaces. From the moment you enter, you’ll appreciate the attention to detail, superior materials, and pride of ownership throughout. This is a home that offers the feeling of new construction without the wait, uncertainty, or compromises that can come with building new. Located on a quiet cul-de-sac while remaining convenient to Windham’s schools, shopping, restaurants, and major commuter routes, 6 Rosewood Street is a rare opportunity to own a truly special home in one of Southern New Hampshire’s most desirable communities.

6 Rosewood St, Windham

$599,000

3 Beds ⋅ 2 Baths ⋅ 5106558 MLS

NEW TO MARKET! Here is a charming Colonial is nestled on just under an acre in highly desirable Windham, New Hampshire. The inviting 3-bedroom, 1.5-bath home offers comfortable living space and an outstanding opportunity to enjoy one of southern New Hampshire's most sought-after communities. Main level features a welcoming living room with a cozy fireplace, a bright kitchen, dining room, convenient half bath, and easy access to the side deck, creating a natural flow for everyday living and entertaining. Upstairs, you'll find three comfortable bedrooms and a full bath, providing plenty of space for family, guests, or a home office. The basement expands the living space with a finished rec room. Two sheds in the yard provide additional space for tools, equipment, and outdoor gear. Step outside to your lovely side deck and enjoy morning coffee, summer meals, or gatherings with friends while taking advantage of the spacious lot. Oil-fired hot-water heat, private water, and private septic provide dependable comfort and functionality. Located in the highly desirable town of Windham, this home is close to excellent schools, scenic trails, parks, golf, shopping, restaurants, and abundant outdoor recreation. Families will appreciate Windham's highly regarded school system and strong community atmosphere, while commuters will love the convenient access to Route 93 and nearby Manchester and Boston. The nearby Tuscan Village destination adds premier shopping, dining, entertainment, fitness, and year-round events just a short drive away. With its desirable location, generous lot, comfortable layout, and endless potential, this is an exceptional opportunity to make Windham your home. Photos may be digitally enhanced.

2 Morrison Rd, Windham

$1,080,000

3 Beds ⋅ 3 Baths ⋅ 5105815 MLS

OFFERS DUE 8/31 by NOON. Better Than New | Luxury Living | Windham's Premier Townhome Community | Welcome to 33 Trails Edge, a stunning 2025 built luxury townhome now available as the community's first resale and offering all the sophistication of new construction, elevated. Thoughtfully upgraded throughout, this home was designed for both everyday living and effortless entertaining. This spacious floor plan offers 3 bedrooms, 2.5 baths, and a dedicated home office ideal for today's flexible lifestyle. The chef's kitchen anchors the main level with upgraded appliances, custom bar cabinetry, and designer countertops, flowing seamlessly into sun-filled living spaces. Custom tile work carries the same elevated craftsmanship throughout, while designer lighting fixtures from Pottery Barn add warmth and character in every room, a level of detail rarely found in a resale. Downstairs, an unfinished daylight walkout basement adds an impressive 1,572 additional square feet of potential, with abundant natural light and high ceilings creating a bright, expansive canvas for future living space, a home gym, or additional entertaining area. Impeccable landscape design enhances the outdoor experience and curb appeal. Move-in ready with none of the wait of new construction, this townhome delivers turnkey luxury in one of Windham's most sought-after locations. Every finish has been curated to feel custom, not cookie-cutter. The community building, still under construction, will feature a gym, meeting space and a large gathering area along with an outdoor pool and patio. Don't miss the opportunity to own a better-than-new home without the new-build timeline. Schedule your private showing today.

33 Trails Edge Rd, Windham

$839,900

3 Beds ⋅ 2 Baths ⋅ 5105241 MLS

Thoughtfully cared for by the same owners for more than 40 years, this home offers a rare combination of spacious single-level living, privacy and access to Cobbett’s Pond. Set on approximately 0.80 acres, this expanded ranch features 3 bedrooms, 2 baths and 2,283 sq. ft. of living space. The vaulted living room features exposed beams, hardwood floors, a stone hearth and pellet stove, flowing into the dining area and large kitchen. An expansive sunroom with walls of windows, a second pellet stove and direct backyard access provides an inviting space to gather, relax and enjoy the natural light. The oversized primary suite includes a walk-in closet, sitting area and private bath, with two additional bedrooms and a second full bath. Outside, relax or entertain on the newer composite deck overlooking the private backyard, complete with a Jacuzzi. Additional highlights include central A/C, a heated 2-car garage, two driveways, a newer roof and extensive updates over the years. The property includes a second parcel conveyed with the home, which may offer additional future possibilities, including potential accessory use or ADU options, subject to buyer due diligence and applicable approvals. Just down the road are two deeded Cobbett’s Pond beaches and shared, unassigned neighborhood dock access. Opportunities like this don't come along often. Schedule your private showing today!

24 Ministerial Rd, Windham

$799,900

3 Beds ⋅ 3 Baths ⋅ 5105067 MLS

Beautifully maintained traditional home in desirable Windham, NH, ready for its next chapter! Exceptional curb appeal welcomes you with a sprawling, irrigated lawn framed by mature trees and vibrant perennial plantings. The main level boasts gleaming hardwood floors throughout, a formal dining room, and a massive front-to-back living room anchored by a cozy wood-burning stove. The sunny, open-concept kitchen features premium granite countertops and flows seamlessly into the vaulted great room. Upstairs houses 3 spacious bedrooms, a dedicated home office, laundry with washer/dryer, and a massive walk-up attic for storage or expansion. The finished lower level works well as a game room/playroom and includes a large walk-in storage closet along with a work shop. You will have Ultimate peace of mind with major component upgrades: a brand-new high-efficiency 5-zone boiler, on-demand hot water system, a newer roof with a 30-year architectural shingles , and a newly updated rear deck perfect for barbecues and entertaining. Turn-key perfection! Do not miss the chance to call this house YOUR home!

33 Oriole Rd, Windham

$1,149,000

4 Beds ⋅ 3 Baths ⋅ 5104975 MLS

Welcome to Walker’s Wood Estates! An exceptional custom Colonial where refined craftsmanship and timeless elegance combine! Offering over 3,500 sq. ft. of impeccably appointed living space, this distinguished residence presents 4 bedrooms, 3 baths and designer finishes throughout. Enter through an inviting 2 story foyer to an expansive, light filled open concept layout anchored by gleaming hardwood floors throughout and meticulous millwork. The chef’s kitchen is the heart of the home with granite countertops, double wall ovens, breakfast bar, stainless appliances and a generous eat in area opening to the family room. The gracious family room, warmed by a gas fireplace, features oversized French doors leading to a large deck overlooking the private, fully fenced grounds ideal for entertaining. A luminous sunroom provides a peaceful retreat, while the formal dining room, enhanced by a tray ceiling and wainscoting, sets the stage for elegant gatherings. The refined study is an architectural highlight, boasting intricate millwork and coffered ceilings a perfect executive workspace or library! The luxurious primary suite is a true sanctuary with a gas fireplace, vaulted ceiling, custom walk in closets and a spa inspired bath with soaking tub, dual vanities & a walk in shower. Three additional well proportioned bedrooms and a full bath complete the upper level. Thoughtful recent updates include fresh interior paint, custom wood blinds and professionally serviced major mechanicals. Outside, the fully fenced yard offers a gas firepit with seating wall, grill hookup and irrigation. A private oasis for relaxation and entertaining! Practical luxuries include a three car garage, full basement & abundant storage. Prime location near Rtes. 93 & 111, premier shopping, top rated schools, parks, golf and recreation, this turnkey home blends elevated design with effortless living! Quick closing possible- an extraordinary opportunity! Don't miss out! OH Sat 11-12:30 & Sun 11-1

37 Sheffield St, Windham

$3,100,000

4 Beds ⋅ 6 Baths ⋅ 5104676 MLS

UNFORGETTABLE LUXURY | Distinctive, sophisticated and designed to leave a lasting impression, this exceptional custom Colonial by renowned builder DiPietro Homes offers 6,000+ sq. ft. of beautifully appointed living space. Thoughtfully enhanced with on-trend updates and improvements, this remarkable home blends exceptional craftsmanship with a fresh, elevated style for today's luxury lifestyle. From the moment you enter, custom millwork and impressive architectural details set this 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's kitchen designed for both everyday living and effortless entertaining. Full-size refrigerator and freezer, generous workspace and a Butler's Pantry complement this thoughtfully designed space. An elegant dining room, private office and functional mudroom complete the main level. Upstairs, the luxurious primary suite is an unforgettable 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 a finished 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. Conveniently located near I-93, schools, shopping and community amenities, with Boston approximately 45 minutes away. A truly unforgettable home where luxury, comfort and exceptional design come together.

17 Bennington 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

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