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33 Londonderry Rd, Windham
$925,000
4 Beds ⋅ 3 Baths ⋅ 5116205 MLS
Welcome to this spacious four-bedroom, three-bath Colonial offering a wonderful blend of comfort, functionality, and distinctive features. With a two-car attached garage and versatile living spaces throughout, this home offers plenty of room to spread out, gather, and enjoy everyday living. The bright and inviting sunroom provides the perfect place to relax, while the extended deck is ideal for outdoor entertaining or unwinding at the end of the day. A generous yard offers plenty of space for outdoor activities, gardening, games, and gatherings with family and friends. One of this home's standout features is the spiral staircase leading to a private balcony overlooking the golf course, creating a beautiful backdrop for your morning coffee or evening sunset. Additional first-floor features include an open-concept kitchen, a private office and a convenient laundry area. A walk-up attic offers excellent storage potential, while the basement adds even more versatility, featuring a recreation area, a dedicated wine cellar, and a workshop for hobbies, projects, or additional storage. With four bedrooms, three baths, and multiple spaces to entertain, relax, or pursue your favorite hobbies, this Colonial offers a unique combination of indoor versatility and outdoor enjoyment. Conveniently located near Windham Country Club, the Windham Rail Trail, town offices, and schools, this special property offers plenty of possibilities. Come see all it has to offer!

33 Londonderry Rd, Windham

9 Campbell Way Unit 4, Windham
$884,900
2 Beds ⋅ 3 Baths ⋅ 5115753 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.

9 Campbell Way Unit 4, Windham

11 Campbell Way Unit 5, Windham
$889,900
2 Beds ⋅ 3 Baths ⋅ 5115586 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.

11 Campbell Way Unit 5, Windham

1275 Old Cheney Rd, Windham
$375,000
2 Beds ⋅ 3 Baths ⋅ 5114767 MLS
Sitting on a high hillside, this home was built for those who love the Earth and want to live lightly on it. From this peaceful haven, you can watch and enjoy the changing seasons and a diversity of Vermont wildlife. Raised organic garden beds provide the opportunity for fresh fruits and vegetables. Its 2.06 acres are mostly forested, but it has clear views to the west of the Turkey Mountain Ridge that are sure to delight you. The property is off the beaten path, yet near Southern Vermont ski mountains and various nature trails. One trail is easily accessed from the house through friendly neighbors’ land to an ancient road and beautiful brook. The home is energy efficient and all electric except for a propane cooktop, and it comes with a net-metered solar array that generates much of the energy used by the house. It is a tall home of three stories, each with about 560 sq. ft. The top floor provides an elevated view of the natural surroundings. It includes a lookoff, the kitchen, dining area, bedroom, and bathroom. The middle floor has a front porch entrance, living room, main bedroom, and bathroom. The lower floor has private outdoor entrances and two rooms with a mini-kitchen, bathroom, and utility room. Attached is a large shed that has served as a workshop, a storage area, and a chicken coop. The folks who built the house live next door and rent part of their land for a community solar field. Children and adults will love exploring the area which is rich in geologic and human history. If you love the land and want a home that honors Nature, this is the place for you.

1275 Old Cheney Rd, Windham

7 Tokanel Rd, Windham
$689,000
3 Beds ⋅ 3 Baths ⋅ 5114760 MLS
Tucked away in a quiet Windham neighborhood, this beautifully updated ranch offers abundant natural light and more space than it looks! Freshly painted interiors, plus new carpet and wood flooring, create a welcoming feel throughout. At the heart of the home, a brand new kitchen features quartz countertops and a center island, perfect for entertaining. The kitchen connects to the dining room, with a sunken great room directly off the kitchen for easy everyday living. The main level features three bedrooms, including a primary bedroom with a private half bath, plus a full bathroom. The finished lower level adds 1,214 square feet, with a kitchenette, bedroom, living room, full bathroom, and laundry, offering flexible space for a variety of needs. Additional improvements include vinyl siding, a newer roof, upgraded electrical, and a new oil tank. An oversized corner lot offers plenty of outdoor space and a large storage shed. Enjoy a peaceful neighborhood setting just minutes from Golden Brook School, major highways, and Windham’s parks and recreation.

7 Tokanel Rd, Windham

7 Campbell Way Unit 3, Windham
$889,900
2 Beds ⋅ 3 Baths ⋅ 5114510 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.

7 Campbell Way Unit 3, Windham

24a Range Rd, Windham
$410,000
1 Beds ⋅ 1 Baths ⋅ 5114186 MLS
This pint-sized home packs a punch! Tucked away from the road on a private .46-acre lot, this charming, fully remodeled home offers the perfect blend of character, comfort, and modern updates. Step inside to discover beautiful hardwood floors, a stylish new kitchen, and an inviting living room featuring a cozy wood-burning fireplace. The covered front porch is the perfect spot to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Outside, the spacious lot offers plenty of room to relax, garden, or entertain, along with a convenient storage shed. Big on charm and low on maintenance, this little gem is a fantastic alternative to condo living, offering the freedom of homeownership without the condo fees! Whether you're a first-time buyer, looking to downsize and enjoy easy single-level living, or exploring the potential for a short-term rental (subject to local regulations), this adorable Windham home offers endless possibilities. Small in size, but big on appeal -don't miss this darling home in desirable Windham.

24a Range Rd, Windham

6 Chadwick Cir, Windham
$759,900
2 Beds ⋅ 3 Baths ⋅ 5113721 MLS
OPEN HOUSE SAT. 10/31 11:00 -1:00. Rare offering in one of the most desirable 55 + communities in southern New Hampshire. Chadwick Place in Windham affords the ease of condominium ownership and living in an attractively landscaped, private and natural setting in close proximity to major commuting routes, amenities and services in the sought-after town of Windham. This free-standing, contemporary cape style unit has an open concept, correctly proportioned floorplan offering two bedrooms with en-suite baths, large living room, upscale kitchen with granite countertops and island, high quality cabinetry and appliances and ample room for dining. The second floor includes a large family room and a "bonus" room in addition to the bedroom and bathroom which affords great flexibility for lifestyle uses and utility. Hardwood and tile flooring throughout, gas fireplace, private deck, 2 bay attached garage, central air conditioning, ceiling fans and a full basement are among the many features and amenities included. All major systems, mechanicals and building components have been diligently maintained in this "like new" home. Welcome to Chadwick Place !

6 Chadwick Cir, Windham

19 Fordway Ext, Windham
$750,000
4 Beds ⋅ 2 Baths ⋅ 5113528 MLS
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

3 Misty Meadow Rd, Windham
$775,000
2 Beds ⋅ 4 Baths ⋅ 5113397 MLS
Windham Meadows! This exceptional detached ranch-style condominium offers an impressive 4,200 sq ft of finished living space, 2-car garage, and an thoughtfully designed floorplan. From the grand foyer, you will appreciate the spaciousness, quality, and comfort this beautiful home has to offer. The formal dining room flows into the generously sized eat-in kitchen, featuring hardwood floors, a gas range, gleaming countertops, abundant cabinetry, & desk area, The spacious living room is perfect for entertaining w/ a gas fireplace and plenty of room for larger furniture. One of the home's true highlights is the stunning sunroom, filled with natural light and overlooks the backyard, with direct access to the deck. The 1st floor primary suite is a serene retreat, offering a separate sitting area with its own gas fireplace, perfect for relaxing before bedtime. The beautifully appointed primary bath features a Safe Step Tub installed this past summer, double vanity, and a separate shower, creating a comfortable and relaxing space. A laundry room and convenient 1/2 bath completes the 1st floor. Upstairs, a beautiful balcony overlooks the living room below, adding an open and elegant feel to the home. The spacious 2nd bedroom offers direct access to a 3/4 bath, while an additional area provides the perfect flex space for an office, reading nook, or guest area. A Murphy-style bed provides a convenient sleeping option for overnight guests.The lower level is an incredible extension of the living space, with 2 walk-out areas to the exterior. Whether you envision a music room, movie nights, or simply an area to relax, the possibilities are endless. A separate office w/ new flooring provides an ideal work-from-home space & storage areas Outside, enjoy the privacy of the backyard patio, a wonderful place to sit beneath the stars at night. A standby generator provides added peace of mind. This home is not to be missed.Quick Closing Preferred!

3 Misty Meadow Rd, Windham

22 Cobbetts Pond Rd, Windham
$575,000
3 Beds ⋅ 1 Baths ⋅ 5113081 MLS
Exceptional value and Location in Windham! Full of character, history, and potential, this distinctive 3-bedroom, 3/4-bath home dating to 1810 offers a unique opportunity to own a property that simply cannot be replicated. The updated kitchen and bathroom creates a blend of historic charm and a more modern living space. Set on .75 acres, the property is home to beautiful established perennial gardens and offers a wonderfully private backyard with a large patio. Its an inviting setting for outdoor entertaining, summer gatherings, gardening, or simply enjoying your own peaceful retreat. Location is a standout feature: Walk to the Windham Town Beach and Rogers Field, and only a short two mile trip to all 4 public schools and the Clyde Pond walking trails. The current owners-of over 30 years have made several thoughtful updates including: full kitchen remodel (2019), bathroom remodel (2022), new furnace (2025), and blown in basement insulation (2026), and too many more to list (see attached file in listing docs). These improvements provide a solid foundation while leaving plenty of opportunity for the next owner to bring their own vision and design ideas. Whether you are drawn to the charm of an early 19th-century home, the privacy of the landscaped grounds, or the opportunity to create something truly special, this property offers a rare combination of history, location, updates, and potential. Come see the possibilities and imagine what you can make of this one-of-a-kind property! One upstairs bedroom does not have a closet. Full list of updates/FAQs in the listing documents.

22 Cobbetts Pond Rd, Windham

33 Brookview Rd, Windham
$444,900
2 Beds ⋅ 3 Baths ⋅ 5112487 MLS
Ready to simplify without giving up the space and comfort you love? Welcome to life at Windham Meadows, one of Windham's sought-after 55+ communities, where low-maintenance living meets the convenience and flexibility today's downsizers are looking for. Thoughtfully designed for everyday ease, this beautifully maintained townhouse offers true first-floor living with a private primary suite, first-floor laundry, and a bright, open-concept layout ideal for both relaxing and entertaining. Vaulted ceilings and abundant natural light create an inviting atmosphere throughout the main living area, while the sunroom provides the perfect spot to enjoy your morning coffee, read a good book, or unwind at the end of the day. The spacious kitchen flows seamlessly into the living and dining areas, making gatherings with family and friends effortless. Step outside to your private deck and enjoy peaceful surroundings without the burden of exterior maintenance. Upstairs, guests and family will appreciate their own private space complete with a generous bedroom, full bath, loft area, and oversized walk-in closet. The unfinished basement offers exceptional storage or the opportunity to create a hobby room, workshop, fitness area, or future finished living space. If you've been searching for a home that allows you to spend less time maintaining and more time enjoying life, this is the opportunity you've been waiting for. Enjoy the benefits of community living, clubhouse amenities, and a desirable Windham, NH location close to shopping, dining, and commuter routes. Downsize your responsibilities, not your lifestyle. Welcome home.

33 Brookview 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

59 Pleasant St, Windham
$439,000
2 Beds ⋅ 3 Baths ⋅ 5112368 MLS
Welcome home to Whispering Winds, one of Windham’s premier 55+ active adult communities! Situated at 59 Pleasant St, this stunning mid-unit condo offers a thoughtful floor plan designed for effortless, one-level living paired with incredible bonus space. Step inside to an airy layout featuring soaring cathedral ceilings and rich hardwood flooring. The main living area flows seamlessly into a bright kitchen and comfortable dining area, leading out to your private backyard patio—perfect for morning coffee or outdoor relaxation. The main level offers convenience with a primary suite, full bathroom, and central air conditioning powered by efficient gas heat. Upstairs, you'll find a versatile loft area alongside additional living space ideal for a second bedroom, home office, or guest suite. Key Features & Highlights: * Spacious Living: 1,522 sq. ft. of above-grade living area across 1.5 stories with 4 rooms, 2 full bathrooms, and 1 half bath. * Bonus Space: Includes a partially finished basement for extra rec space or storage, plus an attached garage and a charming wood deck/patio. * Modern Comforts: Central A/C, forced air gas heating, and low-maintenance community utilities. * Prime Location: Peaceful setting within a highly desirable, well-maintained neighborhood. Don't miss the opportunity to enjoy relaxed, low-maintenance condo living at its finest! OPEN HOUSES THIS WEEKEND! Sat 10/17 & Sun 10/18 @ 10am-12pm

59 Pleasant 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

141 Londonderry Rd, Windham
$1,625,000
4 Beds ⋅ 3 Baths ⋅ 5111633 MLS
Imagine welcoming the holidays in a beautiful new home, with nothing left to do but unpack, settle in, and enjoy! A striking 100-foot custom stone wall welcomes you to 141 Londonderry Road, an exceptional property set back from the road, beautifully landscaped estate in desirable Windham. The home enjoys a sense of privacy and grandeur, with expansive, meticulously manicured Kentucky bluegrass leading the way to the residence. The property also abuts town-owned land with multiple trails, offering the unique opportunity to enjoy nature and explore directly from your own backyard. Built just a few years ago. lightly lived in as it was used as a second home. At the center of the home is a beautifully appointed culinary kitchen featuring custom, generous cabinetry with expansive quartz countertops.The kitchen flows seamlessly into the family room, where a shiplap fireplace creates a inviting focal point. Just beyond, a spacious deck extends the living space outdoors, providing an ideal setting for morning coffee, al fresco dining, or simply taking in the peaceful surroundings. The spacious primary suite provides a peaceful retreat, complete with two generous closets and an adjoining unfinished room that offers exceptional flexibility. The walk-out unfinished lower level with high ceilings and abundant potential, additional living space. Practicality has not been overlooked, either. The 3 car garage features customized cabinetry, an attractive solution for storing tools and equipment. Enjoy the best of both worlds with a private Windham setting just over an hour from Boston, while keeping the beaches and mountains within easy reach.

141 Londonderry Rd, Windham

71 Lower Birch Cir, Windham
$599,000
5 Beds ⋅ 4 Baths ⋅ 5111512 MLS
Have it all on Timber Ridge! This spacious Windham colonial offers four bedrooms in the main house plus a recently renovated one bedroom accessory dwelling unit on the lower level, creating valuable flexibility and rental potential. Set in the mountains, the home welcomes you with a covered front porch and attached two car garage, making four season living that much easier. Inside, a dramatic multi story foyer with floor to ceiling window opens to warm wood floors and a comfortable layout with plenty of room to gather. The kitchen features a breakfast bar island and ample cabinetry, flowing into the dining area and out to the back deck, which was replaced last year. Upstairs, the primary suite includes a private bath and large walk in closet, with two additional bedrooms and a shared full bath nearby. The walk out lower level accessory dwelling unit has been recently renovated and includes its own kitchen, living and dining space, oversized bedroom, and full bath. Radiant in floor heat serves the main and lower levels, while newer heat pumps provide instant, efficient heating and cooling. Whether you are looking for a full time home or a Vermont getaway, this property offers the space, flexibility, and mountain setting to enjoy Southern Vermont in every season. Upstairs, the primary suite includes a private bath and large walk in closet, with additional bedrooms and a shared full bath nearby. The walk out lower level offers even more flexibility with a separate apartment featuring its own kitchen, living and dining space, oversized bedroom, and full bath. Radiant in floor heat on the main and lower levels adds comfort throughout, with mini splits offering efficient ancillary heating and air conditioning in the warmer months. Whether you are looking for a full time home or a Vermont escape, this is a place to spread out, settle in, and enjoy mountain living in every season.

71 Lower Birch Cir, Windham

Cross Rd, Windham
$295,000
5111403 MLS
A special piece of Vermont awaits you. Less than 12 minutes to Magic, 25 minutes to Bromley, and 35 minutes to either Okemo or Stratton. This parcel is such a varied offering, it truly has something for everyone. Peace and quiet is the first thing you will notice. Cross Road is a quiet spot off Windham Hill. There is over 1000 feet of road frontage. Choose your homesite, and your driveway will take you to your private retreat where you will not have any other houses in sight. The acreage is varied and has the type of forest diversity you might expect to find on a much larger parcel. There is a wetland at the low point at the beginning of the property where you will see visiting wildlife. As you travel up the road further, the stonewall along the road appears. The land is all woodland in various age classes of regeneration. The property is in the Current Use program where benefit is a managed forestland that will continue to provide a reduction in your property taxes. There are several species of both hardwood and softwood trees. The property is flat and sloping. Depending on where you choose to site your home, you have some great view potential. You will share the property with a variety of creatures...turkeys, deer, grouse, woodcock, fox, bear, and maybe even moose. Come see if this is the spot for you.

Cross 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

17 First St, Windham
$249,900
2 Beds ⋅ 1 Baths ⋅ 5111290 MLS
BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

17 First St, Windham

17 First St, Windham
$249,900
5111289 MLS
BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

17 First St, Windham

Goodhue Road, Windham
$295,000
5110039 MLS
Rare opportunity to build in Windham! This fully approved 1.95 acre building lot offers a private, wooded setting with the homesite tucked well back from Goodhue Road. A long private drive leads into a wider rear portion of the property, creating an ideal setting for a new home surrounded by mature woods and separation from the road. Much of the upfront work has already been completed, making this an excellent opportunity for a builder or buyer looking to move directly toward construction. Approved survey, subdivision plans and engineered plans are included with the sale. The approved plans provide for private well and septic, with the proposed homesite positioned toward the rear of the property. Located along the Windham/Derry line, the property combines a secluded residential setting with convenient access to Windham's schools, shopping, dining and major commuting routes. A unique opportunity to secure an approved homesite in the Windham School District without starting the lengthy subdivision and engineering process from scratch. Plans and approvals available for review. Buyer and buyer's agent to perform their own due diligence and independently verify all approvals, dimensions, acreage, school assignment, municipal requirements and intended use. Listing party holds an equitable interest in the property pursuant to a purchase and sale agreement and is marketing its contractual interest. Transaction may be completed through an assignment of contract and/or simultaneous closing. Listing party does not currently hold legal title to the property.

Goodhue Road, Windham

21 Oak St, Windham
$850,000
3 Beds ⋅ 2 Baths ⋅ 5109928 MLS
Your chance to own waterfront in Windham, NH! Welcome to 21 Oak Street, a charming A-frame waterfront home set along 48 feet of shoreline on private Cobbetts Pond. Soaring windows fill the open-concept living space with natural light while showcasing beautiful pond views. The home offers two first-floor bedrooms, plus a loft-style third bedroom with a half bath upstairs. Outside, a rare flat waterfront lot, patio, private dock, and beautiful sunsets set the stage for lake life. Launch your boat at the town beach and keep it right at your dock, ready for boating, tubing, jet skiing, kayaking, and more. With plenty of parking and a shed for the water toys, this is your chance to enjoy the waterfront lifestyle right here in southern NH. Private showings available immediately.

21 Oak St, 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

14 Second St, Windham
$1,100,000
2 Beds ⋅ 3 Baths ⋅ 5108732 MLS
You don’t have to be directly on the water to live like you are. This one-of-a-kind custom home was thoughtfully designed from the ground up to take full advantage of its setting and incredible pond views. Modern board-and-batten siding, dramatic black-trimmed windows, warm natural wood accents, contemporary railings, architectural rooflines, and integrated soffit lighting create a home that truly stands apart. Inside, the pond is part of everyday living. From nearly every room and level, expansive windows draw your eye to the water. Upstairs, both bedrooms feature private decks - perfect for morning coffee, an evening glass of wine, or simply enjoying the view. And the best part? Deeded beach rights with a footpath leading directly to the beach and water. You get the beauty and enjoyment of waterfront living without owning the shoreline. The lower level also offers exciting potential; with a wet-bar that contains a mini fridge with sink, full bathroom and a closet. The basement could be used as an additional bedroom/flexible space or future Airbnb-oriented use. You get the views. You get the beach access. You get a spectacular custom-built home designed around the pond - and the short walk between them makes it all the more special.

14 Second St, Windham

1113 Old Cheney Rd, Windham
$519,000
6 Beds ⋅ 5 Baths ⋅ 5108718 MLS
Set on a scenic country property in Windham, this expansive home offers exceptional space, flexibility and a setting with real character. Currently used as a large single-family residence, the home was originally built as a three-family property, with a common entrance serving two living areas and a separate entrance to the garden-level apartment. A central stairwell can connect the spaces, creating options for a large household, multi-generational living, guests, home offices or future reconfiguration. The three living areas include full kitchens, generous living rooms and a total of six bedrooms, with expansive rooms and large windows throughout. There is also ample storage and flexible space for a workshop, studio or dedicated home office. The grounds are where this property becomes especially memorable. Shaped over the years by an artist’s eye and a love of the land, the organic gardens feel established, abundant and wonderfully personal, with fruit trees, flowering shrubs, mature plantings and productive raised beds built at waist height. Several decks and screened porches invite you to slow down and take in the setting, while the property unfolds into a pond, large meadow, playing field, trout stream and walking trails, with views toward Turkey Mountain Ridge. There is a quiet, almost timeless quality here that is increasingly hard to find. Located off the beaten path in picturesque Windham, yet convenient to Southern Vermont skiing, hiking and year-round recreation, the property offers room to live, create, gather and breathe. The home does need TLC and updating, but its scale, versatile layout, organic gardens, land and natural setting make it a true diamond in the rough with tremendous potential.

1113 Old Cheney Rd, Windham

756 Birch Hill Rd, Windham
$479,000
3 Beds ⋅ 2 Baths ⋅ 5108371 MLS
Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Open House on September 26, 10am -12:00 Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

756 Birch Hill Rd, Windham

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

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

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