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17 Bennington Rd, Windham
$2,700,000
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

24 Turtle Rock Rd, Windham
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 5112423 MLS
Year round dream home or vacation retreat on Cobbetts Pond. Welcome to 24 Turtle Rock Road in Windham, where four-season lakefront living meets comfort, privacy, and exceptional outdoor entertainment. Set along 77 ft of frontage on sought after sunny side of Cobbetts Pond, this beautifully remodeled and expanded 3 bedroom, 4 bathroom home offers the perfect opportunity for a year round residence, vacation retreat, or both. A substantial addition and extensive remodel completed in 2017 transformed the property, creating a spacious and inviting home designed to take full advantage of its spectacular setting. The primary suite features his and hers walk-in closets and gorgeous bathroom. Additional major updates including a newer roof, siding, septic system, and HVAC systems provide added peace of mind. Situated on a .29-acre lot, the property offers plenty of parking, an attached 2 car garage, storage shed, and ample outdoor space for entertaining. Step outside to your own outdoor kitchen, ideal for summer cookouts, lakeside gatherings, and making memories with family and friends. One of the home's most inviting spaces is the four-season sunroom, where you can enjoy your morning coffee while taking in beautiful views of Cobbetts Pond. Large windows bring the outdoors in and create a peaceful place to appreciate the changing seasons and embrace the lakefront lifestyle. Your private beach and 77 ft of water frontage provide a wonderful setting for swimming, relaxing, boating, fishing, ice skating, or simply enjoying the serenity of the water. From summer days on the lake to crisp fall mornings, snowy winter adventures, and peaceful spring afternoons, this property offers the opportunity to enjoy true four-season waterfront living. With its substantial 2017 addition and remodel, 3 bedrooms, 4 bathrooms, major system updates, four-season room, outdoor kitchen, private beach, and 77 ft of Cobbetts Pond frontage, 24 Turtle Rock Road is truly a rare opportunity.

24 Turtle Rock Rd, Windham

50 Gaumont Rd, Windham
$1,690,000
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. Built in 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, while a walk-in pantry, custom walnut island, and breakfast nook create a warm, inviting atmosphere. Designed for both everyday living and entertaining, 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

5 Sherwood Rd, Windham
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 5099575 MLS
One buyer's loss is another buyer's opportunity!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.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 gunite inground pool surrounded by professional 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

3 Duston Rd, Windham
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 5107896 MLS
*Accepting BackUp Offers* 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. (9/25)Open House - Canceled

3 Duston Rd, Windham

15 Northland Rd, Windham
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 5101244 MLS
Experience elevated living in one of Windham’s premier neighborhoods. Situated in the highly sought-after Spruce Pond community, this beautifully designed home offers luxury features, exceptional living spaces, and a thoughtfully designed floor plan. Step inside to a grand two-story foyer flanked by a private home office and formal living room. That effortlessly flows into a oversized dining room, and convenient first-floor powder room. At the heart of the home, the gourmet kitchen is beautifully appointed with premium JennAir appliances, a large center island, abundant cabinetry, and an inviting eat-in area that opens seamlessly to the impressive family room featuring soaring vaulted ceilings, a stunning fireplace, and newly installed hardwood flooring. Step outside to the oversized composite deck, creating the perfect setting for outdoor entertaining with a large level backyard. Upstairs, retreat to the luxurious primary suite featuring an oversized bedroom, an expansive walk-in closet, and a spa-inspired bath with heated floors. Three additional generously sized bedrooms and a full bath complete the second level. The finished lower level offers exceptional flexibility with space ideal for a home theater, game room, fitness studio, playroom, guest retreat, or an additional home office, plus unfinished space ready for future expansion, storage, or customization. Designed with comfort and convenience in mind, additional premium features include a whole-house central vacuum system, 8-zone irrigation system, efficient 3-zone HVAC, security system, and exceptional storage throughout. Ideally located in one of Windham’s most desirable neighborhoods with top-rated schools, shopping, dining, and major commuter routes, 15 Northland offers the perfect blend of luxury, comfort, and everyday convenience.

15 Northland Rd, Windham

8 Bear Hill 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

28 Settlers Ridge Rd, Windham
$1,175,000
4 Beds ⋅ 4 Baths ⋅ 5107701 MLS
OFFER DEADLINE TUESDAY, SEPTEMBER 15 AT 12:00 NOON. SELLER RESERVES THE RIGHT TO ACCEPT ANY OFFER PRIOR TO THE DEADLINE. Set on a quiet street in Windham's sought-after Wood Meadow Estates, this DiPietro Homes Colonial is genuinely turnkey, with nothing left to do but move in. Offering 4 bedrooms, 3.5 baths, approximately 3,188 square feet, and a first-floor office on a private 0.53-acre lot, it pairs the ease of newer construction with custom finishes and indoor-outdoor living ready to enjoy. The home lives beautifully, with an open layout where daily life and entertaining unfold with equal ease, showcasing stained hardwood floors, crown molding, wainscoting, and a cathedral-ceilinged entry with a turned staircase. At its heart, a stunning eat-in kitchen features custom Cabico cabinetry, quartz counters, a large center island, Jenn-Air appliances with a six-burner gas range, a walk-in pantry, and glass-front uppers with integrated lighting, opening to a family room anchored by a gas fireplace with stone surround. A French-doored office, wainscoted dining room, half bath, and mudroom-to-laundry layout complete the first floor. Upstairs, the primary suite offers a cathedral ceiling, walk-in closet, and spa-inspired bath with dual vanities, a soaking tub, and glass-enclosed shower. Three additional bedrooms, one with a private bath, flex easily as guest rooms, office, or fitness space, with another full bath nearby. Outdoors is built for entertaining with a deck, pation and hot tub within a fully fenced backyard. Full basement has expansion potential.

28 Settlers Ridge Rd, Windham

37 Sheffield St, 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

34 Glance Rd, Windham
$1,125,000
4 Beds ⋅ 4 Baths ⋅ 5111708 MLS
Welcome home to this inviting Colonial located on a desirable cul de sac road in highly sought after Windham, New Hampshire! Set back from the road on a private lot, this home offers a wonderful combination of comfortable living, incredible outdoor spaces, and a convenient location close to Windham’s excellent schools, shopping, restaurants, and major commuting roads. Step inside to the heart of the home, where the custom designer eat in white kitchen features beautiful finishes and plenty of space for everyday living and entertaining. A formal dining room and spacious living room with built ins add to the charm and functionality of the first floor. Upstairs, the spacious primary suite offers a private bath and extra-large walk-in closet, along with additional bedrooms for family and guests. One of the additional bedrooms has a private full bath. The home also offers an abundance of bonus closets throughout, making storage easy and convenient. The basement adds even more flexibility with a bonus office and additional bonus room, perfect for a home office, gym, playroom, or whatever suits your needs. Now step outside and prepare to fall in love with the backyard! The enormous deck features a commercial grade sun shade, outdoor kitchen, and plenty of room for entertaining. The extra large three season room is sure to become your favorite place to unwind, bringing the outside in and offering the perfect spot to relax and enjoy the peaceful, private setting. Bonus…this incredible bonus space is not included in the listed square footage. The inground pool completes this incredible outdoor oasis and provides the perfect setting for summer fun and entertaining. A wonderful Windham location offering space, privacy, and amenities both inside and out. Showings begin Saturday, October 3rd. We can’t wait for you to see this special home!

34 Glance Rd, Windham

64 Trails Edge Rd, Windham
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 5078493 MLS
This stunning NEW CONSTRUCTION modern farmhouse combines contemporary elegance with classic charm. Situated in a wooded cul-de-sac, this duplex boasts a spacious layout spanning nearly 2,800 square feet across two thoughtfully designed levels. Step inside the oversized foyer and be greeted by an abundance of natural light streaming through large black windows. The main floor features a beautifully designed kitchen complete with Fisher Paykel appliances, ample cabinet and counter space, quartz countertops, and an over-sized island with built-in sink & seating, perfect for culinary enthusiasts and entertaining guests. The living room invites relaxation with its cozy fireplace and stylish accents, creating a warm and inviting atmosphere. The bar features glass front cabinets, quartz countertop, &refrigeration. There is also a large dining area with sliding glass doors overlooking the private patio. The first-floor primary bedroom offers a walk-in closet & private bath featuring dual vanities and a large walk-in glass tile shower. Upstairs are two additional spacious bedrooms, a large loft, and a full bathroom, providing comfort and convenience for family and guests. Additional features include two car garage, central air conditioning, & first-floor laundry room. With easy access to major highways &nature trails, this location offers the perfect blend of convenience and serenity.

64 Trails Edge Rd, Windham

8 Leni Rd, Windham
$1,099,900
3 Beds ⋅ 3 Baths ⋅ 5101380 MLS
Set on a beautifully landscaped corner lot in one of Windham's most sought-after neighborhoods, this meticulously maintained Colonial reflects exceptional pride of ownership and offers the perfect balance of timeless design, thoughtful updates, and exceptional outdoor living. At the heart of the home is a spacious kitchen featuring a large center island, GE Café appliances, and an open layout that flows seamlessly into the inviting family room with a wood-burning fireplace. Elegant dining room details, including shadow boxes and chair rail, add warmth and character, while new carpeting throughout the second-floor bedrooms enhances the home's fresh, updated feel. Upstairs, a versatile bonus room with custom built-ins provides the perfect space for a playroom, media room, home office, or additional living area. The outdoor living spaces are equally impressive, offering a private retreat designed for both relaxation and effortless entertaining. A heated saltwater pool anchors the backyard, complemented by maintenance-free fencing, an expansive level lawn, and a 30' x 30' basketball court. Whether hosting friends, spending time with family, or enjoying a quiet evening outdoors, this exceptional setting was designed to be enjoyed. Additional highlights include a high-bay garage with new garage doors, a full walk-up attic offering outstanding storage or future expansion potential, forced hot air heat, whole-house humidifier, buried 500-gallon propane tank, and an updated 1,500-gallon stone and pipe septic system. Offering an exceptional combination of quality craftsmanship, thoughtful updates, and an unmatched level of care, this is a rare opportunity to own a truly move-in-ready home in one of Windham's premier neighborhoods.

8 Leni Rd, Windham

33 Trails Edge 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

55 Trails Edge Rd, Windham
$1,065,000
3 Beds ⋅ 3 Baths ⋅ 5077771 MLS
This stunning NEW CONSTRUCTION modern farmhouse combines contemporary elegance with classic charm. Situated in a wooded cul-de-sac, this duplex boasts a spacious layout spanning nearly 2,800 square feet across two thoughtfully designed levels. Step inside the oversized foyer and be greeted by an abundance of natural light streaming through large black windows. The main floor features a beautifully designed kitchen complete with Fisher Paykel appliances, ample cabinet and counter space, quartz countertops, and an over-sized island with built-in sink & seating, perfect for culinary enthusiasts and entertaining guests. The living room invites relaxation with its cozy fireplace and stylish accents, creating a warm and inviting atmosphere. The bar features glass front cabinets, quartz countertop, &refrigeration. There is also a large dining area with sliding glass doors overlooking the private patio. The first-floor primary bedroom offers a walk-in closet & private bath featuring dual vanities and a large walk-in glass tile shower. Upstairs are two additional spacious bedrooms, a large loft, and a full bathroom, providing comfort and convenience for family and guests. Additional features include two car garage, central air conditioning, & first-floor laundry room. With easy access to major highways &nature trails, this location offers the perfect blend of convenience and serenity.

55 Trails Edge Rd, Windham

57 Trails Edge Rd, Windham
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 5085952 MLS
This stunning NEW CONSTRUCTION modern farmhouse combines contemporary elegance with classic charm. Situated in a wooded cul-de-sac, this duplex boasts a spacious layout spanning nearly 2,800 square feet across two thoughtfully designed levels. Step inside the oversized foyer and be greeted by an abundance of natural light streaming through large black windows. The main floor features a beautifully designed kitchen complete with Fisher Paykel appliances, ample cabinet and counter space, quartz countertops, and an over-sized island with built-in sink & seating, perfect for culinary enthusiasts and entertaining guests. The living room invites relaxation with its cozy fireplace and stylish accents, creating a warm and inviting atmosphere. The bar features glass front cabinets, quartz countertop, & refrigeration. There is also a large dining area with sliding glass doors overlooking the private patio. The first-floor primary bedroom offers a walk-in closet & private bath featuring dual vanities and a large walk-in glass tile shower. Upstairs are two additional spacious bedrooms, a large loft, and a full bathroom, providing comfort and convenience for family and guests. Additional features include two car garage, central air conditioning, & first-floor laundry room. With easy access to major highways & nature trails, this location offers the perfect blend of convenience and serenity.

57 Trails Edge Rd, Windham

53 Trails Edge Rd, Windham
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 5076634 MLS
This stunning NEW CONSTRUCTION modern farmhouse combines contemporary elegance with classic charm. Situated in a wooded cul-de-sac, this duplex boasts a spacious layout spanning nearly 2,800 square feet across two thoughtfully designed levels. Step inside the oversized foyer and be greeted by an abundance of natural light streaming through large black windows. The main floor features a beautifully designed kitchen complete with Fisher Paykel appliances, ample cabinet and counter space, quartz countertops, and an over-sized island with built-in sink & seating, perfect for culinary enthusiasts and entertaining guests. The living room invites relaxation with its cozy fireplace and stylish accents, creating a warm and inviting atmosphere. The bar features glass front cabinets, quartz countertop, & refrigeration. There is also a large dining area with sliding glass doors overlooking the private patio. The first-floor primary bedroom offers a walk-in closet & private bath featuring dual vanities and a large walk-in glass tile shower. Upstairs are two additional spacious bedrooms, a large loft, and a full bathroom, providing comfort and convenience for family and guests. Additional features include two car garage, central air conditioning, & first-floor laundry room. With easy access to major highways & nature trails, this location offers the perfect blend of convenience and serenity.

53 Trails Edge Rd, Windham

7 Porcupine Rd, Windham
$1,000,000
4 Beds ⋅ 4 Baths ⋅ 5113090 MLS
Opportunities like this do not come around often. Set on a desirable cul-de-sac in one of Windham’s established neighborhoods, where homes are rarely offered for sale, this beautifully maintained Colonial delivers the location, space, and lifestyle buyers have been waiting for. Offering 2,838 square feet of living space on .69 acres, the home features four bedrooms, 3.5 baths, a dedicated home office, and a spacious, functional layout with plenty of storage throughout. The kitchen is finished with granite countertops and a center island, creating a welcoming space for everyday living and entertaining, while freshly painted interiors give the home a bright, move-in-ready feel. Need even more room? A finished walk-up attic provides valuable additional living space and flexibility for a guest room, media room, playroom, or bonus area. The walkout basement offers even more potential and could easily be finished to create additional living, recreation, or entertaining space while still providing excellent storage. Meticulously maintained inside and out, the pride of ownership is immediately apparent. The property abuts conservation land, adding to the peaceful setting and providing a beautiful natural backdrop. Step outside to a beautiful patio and firepit area designed for summer evenings, fall gatherings, and effortless outdoor entertaining. Tucked into a sought-after neighborhood yet just minutes from major highways, shopping, dining, schools, and everything Windham has to offer, this home provides the neighborhood setting buyers want with the convenience they need. A rare opportunity in a neighborhood where homeowners tend to stay. This is one you will not want to miss.

7 Porcupine Rd, Windham

3 Moeckel Rd, Windham
$950,000
3 Beds ⋅ 3 Baths ⋅ 5112808 MLS
Single Level Living, with a View! Welcome to a special waterfront retreat on Moeckel Pond, where picturesque water views, wildlife, and the peaceful sounds of nature create a truly inviting place to call home. Set on 2.62 acres in desirable Windham, this ranch-style property offers the ease of one floor living, along with a convenient location just 35 minutes from Boston. Step inside to a spacious open floor plan designed for easy living and entertaining. The living room, with its wood burning insert, is the perfect spot for cozy fall and winter evenings. The kitchen features granite countertops and overlooks the living space, keeping everyone connected to the conversation. A charming bump-out dining-area provides the perfect spot to dine while taking in the view. Sliding doors from both the living room and kitchen open directly to the expansive deck, creating an easy connection between the indoor and outdoor living spaces. Back inside, the primary bedroom offers a walk-in closet and custom bath with a direct-entry tiled shower. Two additional bedrooms and a full guest bathroom are located at the opposite end of the home, providing privacy for guests. A convenient mudroom off the two car attached garage provides a practical entry point, along with a half bath and laundry for added ease. The finished basement, complete with a pellet stove, offers flexible additional living space that can adapt to your needs, whether used as a recreation room, home office, hobby space, or gathering area. With central AC, a two-car attached garage, finished basement space, irrigation, and convenient access to all that Windham has to offer, this home brings together comfort, functionality, and a beautiful natural setting. Enjoy the tranquility of waterfront living, kayaking and canoeing  without giving up convenient access to the city. Come see how this special waterfront property can fit your vision and provide the lifestyle you've been looking for. Showings begin Tuesday, October 6.

3 Moeckel Rd, Windham

5 Campbell Way Unit 2, 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

25 Faith Rd, Windham
$875,000
3 Beds ⋅ 3 Baths ⋅ 5112059 MLS
Please note open house schedule for 10/3/2026 has been cancelled Tucked into a beautifully wooded setting, 25 Faith Road offers the kind of privacy and outdoor space that can be hard to find yet it’s only about 10 minutes from Exit 3 on I-93. A winding paved drive brings you through the trees and opens to a welcoming home surrounded by mature woods and an expansive, backyard. It’s a setting that feels wonderfully removed while keeping everyday travel remarkably convenient. Inside, this 3-bedroom, 2½-bath home has character that goes well beyond a typical floor plan. At its heart is a custom-built kitchen, exquisitely crafted by a true craftsman, with the kind of detail and workmanship that gives the space a personality all its own. Multiple living areas provide plenty of room for both lively gatherings and quiet relaxation, including a dramatic vaulted family room, while the 3 season porch creates a wonderful connection between the home and its wooded surroundings. Outside, the property really comes into its own. A broad, level lawn provides room to play, garden and gather, while the deck and fire pit create inviting places to enjoy long summer evenings and crisp New Hampshire fall nights. Mature woods frame the property and create a sense of privacy that is apparent from the moment you arrive. A detached two-bay garage/outbuilding adds another layer of versatility, complementing the home's additional garage and providing valuable space for vehicles, equipment, hobbies or storage. Private without being isolated, 25 Faith Road brings together character, craftsmanship, outdoor space and convenience all approximately 10 minutes from I-93.

25 Faith Rd, Windham

8 Rolling Ridge Rd, Windham
$824,900
3 Beds ⋅ 2 Baths ⋅ 5109201 MLS
Gorgeous custom built ranch in highly desirable Windham Estates. Stunning facade and recessed entryway add to the most inviting curb appeal. Foyer is open to kitchen and expansive living room. Gas fireplace flanked by built in shelving with crown moldings and warm toned hardwood flooring throughout. Tall maple cabinetry with stainless appliances, center island and 6 foot patio doors highlight the beautifully equipped kitchen. Pantry and laundry room are conveniently tucked away off the main living area. Flex space adjacent to kitchen, ideal den or home office overlooks wooded landscape and fenced inground pool area. Primary en Suite with double sinks and walk in shower with designer tile and stone tops. Additional bedrooms and full bath are well sized and neutral tones continue with the cohesive floorplan. Deck and screened porch make entertaining poolside comfortable for enjoyable seasonal living. Generator, central air, central vac, irrigation and direct entry attached two car garage. True one level living in almost 2100 sf with quality upgrades are a rare find in this sought after community. Top performing school system in Southern NH's most coveted town. Come see this gem! OPEN HOUSES Friday 9/11, 4pm-6pm, Saturday 9/12, 10am-12 and Sunday 9/13, 10am-12.

8 Rolling Ridge Rd, Windham

2148 Abbott Rd, Windham
$815,000
4 Beds ⋅ 3 Baths ⋅ 5103519 MLS
Set on 53 private acres with mountain views, this four-bedroom, three-bath home offers the space and setting to enjoy every season. Built in 2007 and located just a short drive from Stratton, Bromley, Magic, and Okemo, it's equally suited as a full-time residence or a mountain retreat. The heart of the home is a welcoming great room with a floor-to-ceiling stone fireplace and a wall of windows that frames the surrounding landscape. The open-concept kitchen, dining, and living areas make it easy to gather after a day outdoors. A spacious primary suite provides a comfortable retreat, while a loft, game room, walk-out lower level, and oversized mudroom offer room for everyone and all the gear that comes with Vermont living. An attached two-car garage adds everyday convenience. The home is offered furnished. Steps from the house, and into the meadow is a 22' x 30' barn that expands the possibilities. Three overhead doors make it ideal for storing snowmobiles, ATVs, tractors, or other equipment, and there's room for horses as well. The unfinished second floor is already equipped with lighting and six windows that fill the space with natural light, ready for a workshop, studio, or future expansion. The VAST trail is at the end of the road, ride your snowmoobile direct from the house to miles of connected trails. Stone steps built into a classic Vermont stone wall lead from the house to the meadow below, adding to the property's charm and connection to the landscape. Whether your weekends are spent skiing, snowmobiling, hiking, or simply enjoying the peace and quiet, this property offers the best of Vermont living. As the wall art inside the home suggests: "Snowmobile. Ski. Rest."

2148 Abbott Rd, Windham

19 Fordway Ext, Windham
$750,000
4 Beds ⋅ 2 Baths ⋅ 5113528 MLS
***OFFER DEADLINE MONDAY OCT 12th 12:00 ***Lovingly cared for by its original owner, this updated Contemporary offers 4 bedrooms, 2 full baths, and over 2,600 square feet of inviting living space on more than an acre of land. Step inside to a spacious living room showcasing soaring vaulted ceilings, exposed wood beams, and a wood burning fireplace that creates a warm and welcoming focal point. The updated kitchen features quartz countertops, new appliances, and an adjoining dining area ideal for everyday living and entertaining. A sunroom brings the outdoors in, offering a light filled retreat overlooking the peaceful backyard. The first floor primary bedroom features a walk in closet, while three additional bedrooms offer plenty of space for family, guests, or a home office. Recent improvements include brand new hardwood flooring throughout the first floor, new carpeting in all bedrooms, fresh interior paint, and numerous other updates. Outside, a large, recently updated deck overlooks the private, level backyard, creating an ideal setting for outdoor dining, entertaining, or simply relaxing. A new walkway, two car garage, and unfinished lower level with excellent storage and future possibilities add to the home's appeal. Ideally situated just minutes from I-93, this location offers convenient access to Boston and destinations throughout Southern New Hampshire, while the nearby Windham Rail Trail provides miles of scenic walking and biking. With its distinctive architecture, thoughtful improvements, private setting, and convenient Windham location, this home offers the space, comfort, and the lifestyle you've been searching for.

19 Fordway Ext, Windham

34 Sharon 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

33 Oriole Rd, Windham
$719,900
3 Beds ⋅ 3 Baths ⋅ 5105067 MLS
Be home for the holidays! Windham Home in a highly desirable neighborhood featuring 9 rooms, a home office, finished basement, and a walk-up attic, 33 Oriole Road is ready for a quick move-in. Positioned for a fast closing, this beautiful 3-bedroom, 3-bathroom Colonial sits on a 2.03-acre lot. Enjoy total peace of mind with excellent structural and mechanical updates, including a newer roof, an updated back deck, a brand-new 5-zone boiler, and a high-efficiency on-demand water heater. Outside features include beautiful front lawn, 10x16 Shed with power, irrigation, and perennial flowers that bloom all spring and summer. Step inside to find gleaming hardwood floors spanning the main level. Entertain in the front-to-back living room. Prepare holiday meals in the sunny kitchen equipped with premium granite countertops, which flows seamlessly into a vaulted great room full of natural light, creating an ideal setup for entertaining. Upstairs includes three bedrooms, office/nursery, second-floor laundry, and a massive walk-up attic offering storage or future expansion potential. The lower level features a finished climate-controlled bonus room boasting new carpeting alongside a separate workshop and storage area. Complete all this with a 2-car garage, central vacuum, and security system this turnkey home is ready for you to unpack and celebrate the season. Sellers say "make me an offer". Schedule a tour today!

33 Oriole Rd, Windham

3 Farrwood Rd, Windham
$719,000
3 Beds ⋅ 3 Baths ⋅ 5105355 MLS
OPEN HOUSE CANCELLED - Property is Under Contract An amazing opportunity to own a spacious and beautifully appointed home in a desirable area, offering exceptional value and a thoughtful blend of comfort, character, and versatile living spaces. From the moment you arrive, you'll appreciate the stone walls lining the driveway and the inviting farmer’s porch with granite flooring. Inside, the family room provides a warm and welcoming gathering space with a beautiful stone fireplace. The three-season porch, featuring windows and a skylight, offers a bright and relaxing space to enjoy throughout much of the year. Step outside onto the composite deck with Sunsetter awning, ideal for outdoor entertaining or unwinding at the end of the day. The spacious primary bedroom features a vaulted ceiling and ceiling fan, along with a separate sitting room with its own fireplace. The primary bathroom offers a shower, two vanities, and two skylights, creating a bright and comfortable retreat. The kitchen features granite countertops and stainless steel appliances, while the finished basement includes a versatile playroom for additional living space. A two-car garage provides convenient parking and storage. With its desirable location, spacious layout, and numerous special features, this home offers an excellent opportunity to enjoy comfortable living with plenty of room to entertain, relax, and make it your own.

3 Farrwood Rd, Windham

717 Horsenail Hill 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

60 Gordon Mountain 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

20 Addison Rd, 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

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