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$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
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 5103616 MLS
Welcome to this Waterfront Sanctuary of Unrivaled Craftsmanship on Canobie Lake! Offering 150 feet of shoreline, this exceptional residence is designed to capture lake views from nearly every room while blending timeless elegance with luxury. Framed by Manicured Boxwood Shrubs and a Circular Drive, this Custom Home showcases Architectural Charm and Refined Details. Nestled on a Private, Professionally Landscaped Lot along the Crystal-Clear Waters of Canobie Lake-- a highly coveted Class A Fishery known for peaceful coves, exceptional boating, and very limited public access. Step inside to an Expansive, Single-level Open Floor Plan filled with Natural Light from walls of windows, highlighting Gleaming Hardwood Floors and Soaring Tongue and Groove Cathedral Ceilings. Designed for everyday living and entertaining, the main living area features the first of 4 fireplaces and flows into a true Chef’s Kitchen, equipped with an Oversized island, dual Refrigeration, 6-burner Gas Range, Double Ovens and a Butler’s Pantry complete with a second sink and dishwasher. Unwind in the Sunroom beside another Fireplace or step onto the Expansive Trex Deck overlooking the Tranquil Waterfront. The Primary Suite serves as a retreat, offering double closets and an Updated, Spa-inspired Bath with a Large Tiled Shower featuring Dual Shower Heads. Every bathroom has been thoughtfully renovated with exquisite finishes. The Finished Walkout Lower Level offers exceptional versatility with a Private In-Law Apartment featuring its own Chef’s Kitchen with a 6-burner gas range, double ovens, spacious living area and direct access to the covered lower patio. Rare for lakefront living, this home also includes a Spacious 3-Car Garage, abundant storage, and extensive updates. Minutes from shopping, dining and I-93 for an easy commute to Manchester and Boston, this exceptional home delivers an extraordinary lifestyle where Waterfront living meets Turnkey Luxury.

22 Woodvue Rd, Windham
$1,800,000
4 Beds ⋅ 4 Baths ⋅ 5101534 MLS
Designed to Live Like a Ranch...With Space When You Want It. Experience the ease of luxury single level living in this exceptional custom ranch, thoughtfully designed for comfort, flexibility, and sophisticated style in one of Windham's most desirable neighborhoods. Nearly new and impeccably crafted, this 4 bedroom, 4 bath home is just minutes from Tuscan Village, major commuter routes, dining, shopping, and recreation. The gourmet kitchen is the heart of the home, featuring premium appliances, an oversized waterfall island with seating, abundant prep space, and a walk-in pantry. The open-concept design flows seamlessly into the dining and living areas, highlighted by a cozy fireplace, stylish wet bar and direct access to the covered deck and hot tub, perfect for relaxing or entertaining year round. Designed for today's lifestyle, the thoughtfully planned layout includes two private ensuite bedrooms, ideal for guests or multigenerational living. The luxurious primary suite offers a gas fireplace, radiant heated floors, spa-inspired bath, and an expansive custom walk-in closet. Two additional bedrooms share a beautifully appointed Jack-and-Jill bath. The finished walkout lower level provides exceptional flexibility with a professionally designed wellness studio featuring mirrored walls and premium fitness equipment, along with additional space for a media room, recreation area, hobbies, or entertaining. Unfinished space with plumbing already in place for a future bath offers room to expand as your needs evolve. Additional highlights include owned solar panels, whole-home ethernet wiring, energy-efficient construction, smart irrigation, security system, fenced yard, and deeded access to walking trail connecting to the Windham Rail Trail. Offering the convenience of one-level living with the flexibility to entertain, pursue your passions, and host family and friends, this exceptional home is designed to adapt beautifully to every stage of life. Quick Close Possible!!

7 Lilac Ridge Rd, Windham
$790,000
3 Beds ⋅ 3 Baths ⋅ 5100937 MLS
OFFER DEADLINE TUESDAY, JULY 28TH AT NOON. Welcome home to 4 Longmeadow Rd, ideally situated in one of Windham's most desirable neighborhoods! This colonial offers 2,904 square feet of finished living space, including a versatile finished basement, all set on a beautifully private 1.26-acre lot. The smart layout offers a functional flow, with all three bedrooms conveniently located on the second floor and a half bath on the main level for guests. Step outside to your own screened-in deck, the perfect spot for morning coffee or evening relaxation overlooking the private, tree-lined yard. Move right in and make it your own with cosmetic updates over time, instead of paying for someone else's design decisions. All in a fantastic location close to top-rated schools, shopping, and easy highway access. Homes in this neighborhood don't last, schedule your showing today!

4 Longmeadow Rd, Windham
$800,000
4 Beds ⋅ 4 Baths ⋅ 5100902 MLS
Under contract pending buyer's home sale. Back-up offers are welcome. Windham checks every box and 29 Harris Road makes it easy to move right in before fall! Situated on over an acre just five minutes from Route 93 and a short drive to Tuscan Village, the Rail Trail, and tax-free shopping, this 4-bedroom colonial offers the kind of location that you've been looking for. The updated kitchen anchors the main level with a vaulted ceiling, custom cabinetry, granite counters, stainless appliances, and a dining area warmed by a brick fireplace. The primary suite is conveniently on the first level with laundry and access to the back deck. There are hardwood floors throughout and central AC keeps things comfortable inside all summer long. The 3 additional bedrooms upstairs are oversized and feature tons of closet space. The finished walkout basement with heating, AC, and a half bath is where the flexibility really opens up - use it as a family room, a home office suite, an in-law setup, or a fifth bedroom. The configuration adapts to however you want to live. Outside you'll enjoy the three-car garage, a sprawling fenced yard, and a Tesla Energy Storage System that's already doing the work. You won't want to miss this opportunity!

29 Harris Rd, Windham
$649,000
3 Beds ⋅ 2 Baths ⋅ 5100164 MLS
Welcome to year round tranquility in desirable Windham! Built in 2018, this beautifully maintained 3 bedroom, 2 full bath home offers the perfect blend of modern style and relaxed living with deeded water access to Cobbetts Pond. The light and bright open-concept floor plan features stunning dark hardwood floors throughout, creating warmth and elegance in every room. The kitchen shines with quartz countertops, stainless steel appliances, and seamless flow into the living and dining areas, making entertaining effortless. A spacious dining area, first-floor bedroom or office, and a full bath complete the main level and provide flexibility for guests or remote work. Upstairs, the spacious primary bedroom offers a vaulted ceiling, oversized window seat, abundant natural light, and generous closet space. A second bedroom, convenient second floor laundry area, and an additional full bath complete the upper level. Enjoy peace of mind with the recently added Generac standby generator. Ideally located just minutes from Route 93, commuting is easy while shopping, restaurants, and everyday conveniences are all close by. Experience the best of Windham living with modern comfort and the recreational lifestyle that comes with deeded access to beautiful Cobbetts Pond.

12 Grove St, Windham
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 5099575 MLS
Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering 4 spacious bedrooms and a beautifully appointed walk-out lower-level in-law suite, this remarkable home blends sophistication, comfort, and versatility. A grand two-story foyer welcomes you into a home showcasing impeccable craftsmanship, classic architecture, and custom millwork throughout. The thoughtfully designed floor plan features a private home office, elegant formal dining room, and an inviting family room centered around a stunning fireplace. The expansive chef's kitchen flows seamlessly into the main living areas, creating the ideal space for everyday living and entertaining. It is equipped with a custom cabinet-front refrigerator, plus an additional stainless steel refrigerator offering expanded refrigerated storage. Just beyond, a sun-filled four-season room overlooks the private backyard and opens to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room features custom millwork, a built-in bar, and the perfect setting for entertaining. Designed with both luxury and practicality in mind, the home offers central air conditioning throughout, while strategically placed mini-split systems provide individualized comfort and energy-efficient climate control in frequently occupied spaces. The luxurious primary suite features a spa-inspired bath, while the additional bedrooms are generously sized. The walk-out lower level offers a complete in-law suite with its own living space, ideal for multigenerational living, guests, or an au pair. Outside, the expansive composite deck overlooks a spectacular gunite inground pool surrounded by professionally designed landscaping, creating exceptional privacy. A classic farmer's porch completes this extraordinary property, where timeless architecture, refined finishes, and effortless indoor-outdoor living come together.

5 Sherwood Rd, Windham
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 5098632 MLS
The one you’ve been waiting for. Perfectly positioned on a private, oversized 2.35 acre lot in one of Windham’s most coveted neighborhoods, this beautifully updated home offers the ideal blend of luxury, comfort, and convenience. At the heart of the home is a stunning, brand-new designer chef’s kitchen that truly steals the show. Thoughtfully appointed with custom cabinetry, quartz countertops with a full height quartz backsplash, premium built-in appliances including double wall ovens, a built in espresso machine, warming drawer, pot filler, and an oversized center island, this exceptional space was designed for effortless entertaining and everyday living. Continuing through the home, you’ll appreciate the dramatic two story foyer, custom built in mudroom with a dedicated desk area, and convenient first floor half bath. The kitchen flows seamlessly into the dining room, family room, living room, heated sunroom, and outdoor deck, creating an inviting layout perfect for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms and two full baths, including a luxurious primary suite featuring a private en suite bath, an oversized custom walk-in closet with built-ins, and an adjoining flex room ideal for a private office, nursery, fitness studio, dressing room with a center island, or creative space. Three additional spacious bedrooms and a well appointed full bath complete the second level. The oversized walk up unfinished attic offers abundant storage and endless potential to create additional living space tailored to your needs. The finished lower level provides incredible bonus space for movie nights, game days, a home gym, playroom, or whatever suits your needs. Step outside to your own backyard retreat featuring a composite deck overlooking a paver patio with a hot tub hook up. Two portable garages provide additional storage for vehicles, equipment, tools, or hobbies.

8 Bear Hill Rd, Windham
$1,599,000
4 Beds ⋅ 2 Baths ⋅ 5096240 MLS
Experience the best of lake life in this beautifully renovated waterfront retreat on sought-after Cobbetts Pond. Offering over 2,400 square feet of thoughtfully designed living space, this exceptional home features four bedrooms, including a custom-built bunk room perfect for hosting family and guests, two updated bathrooms, bamboo flooring throughout, and mini-split systems in every bedroom and the main living areas for year-round comfort. A durable metal roof provides peace of mind, making this truly a turn-key property. With 50 feet of private waterfront, a boat dock, and stunning lake views, every day feels like a vacation. The open and inviting layout was designed for gathering, while expansive composite decking extends your living space outdoors, providing ample room for entertaining, dining al fresco, or simply unwinding while watching spectacular sunsets over the water. Gather around the fire pit for s'mores under the stars and create memories that will last a lifetime. Outdoor living takes center stage with a remarkable custom outdoor kitchen featuring a premium Coyote oversized grill, Asado built-in smoker, granite bar, and plenty of space for hosting family and friends after a day on the lake. Whether boating, swimming, paddleboarding, kayaking, or fishing, the private waterfront offers endless opportunities to enjoy the lake lifestyle. Coveted Cobbetts Pond is one of Southern New Hampshire's premier recreational lakes, known for its crystal-clear waters, vibrant boating community, and year-round enjoyment. Conveniently located just minutes from shopping, dining, and major highways, it offers the perfect blend of everyday convenience and vacation-style living. A rare opportunity to own a beautifully renovated waterfront home in one of Southern New Hampshire's most desirable lake communities - all that's left to do is unpack and enjoy.

64 Turtle Rock Rd, Windham
$1,075,000
4 Beds ⋅ 3 Baths ⋅ 5095130 MLS
Tucked quietly away from the road on a private, beautifully maintained 3.46-acre lot, this impressive 3700plus -square-foot home offers the perfect blend of privacy and convenience. Ideally located just 5–10 minutes from schools, shopping, and recreational amenities, you'll enjoy a peaceful setting without sacrificing accessibility. (DELAYED SHOWINGS UNTIL 6/26) The level backyard provides ample space for outdoor activities, featuring a swing set, a storage shed, and plenty of room for a volleyball game, soccer, or even a seasonal ice rink. Beyond the stockade fence, you'll find raised garden beds ready for planting. Nature enthusiasts will appreciate direct access to the town forest, with more than 350 acres of trails and outdoor adventures right beyond the property. School busses drop off and pick up is at the driveway! Inside, the home is equally impressive, showcasing updated bathrooms, brand-new kitchen countertops, and a stylish new backsplash. The finished third floor offers flexible living space, while the basement is currently configured as a home gym. With its spacious layout, modern updates, and elevated setting that creates a true "top of the world" feeling, this exceptional property is a must-see.

12 Longmeadow Rd, Windham
$825,000
3 Beds ⋅ 3 Baths ⋅ 5094260 MLS
**OFFER DEADLINE SET FOR MONDAY AT 12 NOON** Offered for the very first time since custom built 30 years ago, this extraordinary Windham estate is a rare opportunity to own a property that has been well loved for and thoughtfully enhanced over decades. Perched on 3.13 private acres, this unique Colonial offers 3 bedrooms, 2.5 baths, and welcomes you with timeless New England charm, highlighted by a distinctive two-story turret and wraparound porch featuring intricate arch detailing. The professionally manicured grounds just create the truly storybook setting. Inside, you'll discover one of the home's most remarkable features; a stunning peninsula saltwater aquarium that serves as a living centerpiece at the heart of the home! Designed with an automated filtration system for minimal upkeep, you'll enjoy all of the beauty and tranquility of a thriving reef ecosystem including a variety of stunning bright specialty fish and coral, with little more than just feeding them each evening! Step outside and relax beneath the retractable awning on the spacious 20' x 14' deck. Then, stroll among mature specimen plantings throughout including rare Japanese Maple tree varieties. While you experience your own private retreat, a cascading waterfall into two picturesque koi ponds creates a peaceful soundtrack to everyday life. As if that wasn't an impressive list of features, the abutting hiking/walking trails of Deer Leap with unfiltered views of and private access to Rock Pond beyond the property line, are additional experiences you're privy to with this home! A partially finished lower level, 2 car garage, front & back yard irrigation system, and a standby generator add to the year round comfort and peace of mind. Properties like this are rarely available... a home where architecture, nature, and lifestyle come together to create something truly special; a living destination! Seller to find suitable housing.

76 Marblehead Rd, Windham
$1,795,000
2 Beds ⋅ 4 Baths ⋅ 5093921 MLS
Custom-built waterfront home on Cobbetts Pond with 50 feet of private frontage, private dock, sandy-bottom shoreline, and excellent swimming. Builtin 2016, this exceptional property combines classic New England lake-house charm with modern amenities, efficiency, and convenience. Thoughtfully designed and expertly crafted, the home features extensive custom woodwork, wood ceilings, shiplap detailing, rich walnut finishes, and exceptional craftsmanship throughout. The open-concept floor plan offers bright, coastal-inspired living spaces with abundant natural light and beautiful water views. A stunning stone fireplace anchors the main living area, and a walk-in pantry, while the custom walnut island and breakfast nook create a warm, inviting atmosphere. Designed for both everyday living andentertaining, the home includes a designated office area, guest bedroom, nursery, second-floor laundry, and a spacious upper-level hallway lined with custom built-in bookshelves. The primary suite serves as a private retreat with a waterfront deck, walk-in closet, and spa-inspired bath. The screened porch and adjoining deck provide the perfect setting for relaxing or entertaining, while the level backyard offers easy access to the shoreline, private dock, and sandy swimming area. The walk-out lower level offers a unique lodge-inspired retreat with custom log-style walls and ceilings, plus a full kitchen and 3/4 bath—ideal for guests, recreation, extended family, or potential in-law accommodations. A detached heated garage provides storage for vehicles, watercraft or lake gear, while the unfinished attic above offers additional storage space. Walkout to patio area. Additional storage under the porch. Enjoy boating, fishing, kayaking, paddleboarding, swimming, and year-round waterfront living from this exceptional Cobbetts Pond property. Rarely available, this newer custom-built home offers the perfect blend of lake-house character, luxury, craftsmanship, and modern comfort.

50 Gaumont Rd, Windham
$869,900
2 Beds ⋅ 3 Baths ⋅ 5093852 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.

4 Campbell Way, Windham
$859,900
2 Beds ⋅ 3 Baths ⋅ 5093777 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.

2 Campbell Way, Windham
$900,000
3 Beds ⋅ 2 Baths ⋅ 5088057 MLS
Set on over 2 acres in sought-after Windham, this beautifully updated 3-bedroom, 2-bath single-family home offers the perfect blend of comfort, convenience, and opportunity. Known for its highly regarded school district and ideal commuter location with easy access to major highways, Windham continues to be one of Southern New Hampshire’s most desirable communities. Inside, you’ll find a spacious and functional layout designed for everyday living and entertaining alike, with thoughtful updates throughout the home. The flexible floor plan also offers the ability for a fourth bedroom, in-law suite, office, or private guest space, creating added versatility to fit a variety of living needs. The attached 2-car garage adds convenience and additional storage, while the expansive lot provides privacy, room to enjoy the outdoors, and potential subdivision opportunities for future value or development potential (buyer to perform due diligence). Whether you’re looking for a move-in ready home, extra land, or long-term investment potential, this property checks all the boxes. Property to be sold as-is, as seen. Septic system requires certification for use. Seller is open to offering the dwelling with approximately 1 acre for $750,000, providing a unique opportunity and added flexibility for buyers.

6 Maple St, Windham
$799,000
4 Beds ⋅ 5 Baths ⋅ 5086432 MLS
Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont’s top winter and summer activities.

1035 Vt Route 121, Windham
$250,000
5 Beds ⋅ 2 Baths ⋅ 5024743 MLS
Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts!

1614 Burbee Pond Rd, Windham

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