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135 Overlook Dr, Londonderry
$425,000
5094565 MLS
Investment opportunity! This beautiful ski country compound offers 3 potential streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped with their own kitchen and come with paying tenants. Keep the property in its current configuration, or combine the main house into one living area, with the barn as an in-law suite. A septic design exists for a subdivision of the property which, if the subdivision is obtained and a septic permit approved, would enable further development. Property to be sold as-is. Owner financing available.

135 Overlook Dr, Londonderry

2 Tamarack Pl, Londonderry
$179,900
2 Beds ⋅ 1 Baths ⋅ 5094326 MLS
Back on market, Buyer denied by park. *Owner Financing Available!* Welcome to 2 Tamarack Place in Londonderry, located in the lovely Whispering Pines Community! Nestled on a spacious, tree-lined lot, this move-in ready home offers a rare opportunity to enjoy homeownership in Londonderry without sacrificing space or setting. Step onto the charming covered front porch and into a bright, open-concept living space filled with natural light. Attractive flooring and a functional layout create an inviting setting for both everyday living and entertaining. The spacious kitchen features rich cabinetry, ample counter space, a breakfast bar, and modern appliances, flowing seamlessly into the dining and living areas. Nicely sized bedrooms provide comfortable retreats, while the full bathroom is thoughtfully designed. Fresh, neutral colors throughout create a warm and inviting atmosphere ready for your personal touch. Outside, enjoy a large yard surrounded by mature trees that provide a peaceful sense of privacy while still being close to shopping, restaurants, major commuter routes, and all that Londonderry has to offer. Whether you're downsizing, purchasing your first time home, or looking for low-maintenance living in a desirable location, this property is a fantastic opportunity you won't want to miss. Schedule your showing today!

2 Tamarack Pl, Londonderry

157 Old Sawmill Rd, Londonderry
$795,000
4 Beds ⋅ 4 Baths ⋅ 5094205 MLS
Nestled in Lowell Lake community and is offer furnished! This home offers the perfect blend of Vermont charm, comfort, and outdoor recreation. Originally built in 1971 and extensively renovated and expanded in 1992, this inviting home features nearly 3,200 square feet of living space designed for year-round enjoyment. Take in front-row views of Magic Mountain's ski trails right from your front deck and dining room - watch skiers carve down the slopes by day, and in the evenings, enjoy the quiet spectacle of the snow cats grooming the trails. Set in the heart of Southern Vermont ski country, Magic, Bromley, and Stratton Mtns are all just 20 minutes away, with Okemo, Mount Snow, and Killington also within an hour's drive few properties offer this kind of access to Vermont's best skiing. Snowmobile enthusiasts will love the direct VAST trail access right off the road no trailering required. Simply load up and ride straight from home onto Vermont's extensive network, with connections to trails across the entire state. The backyard abuts Lowell Lake State Park, ensuring lasting privacy with no future development possible behind the property, while offering endless opportunities for hiking, kayaking, and snowshoeing right out your back door. A private pond adds to the picturesque setting, and multiple decks provide ideal spaces for relaxing, entertaining, or simply watching the mountain views change with the seasons. Inside, warm and welcoming living areas are highlighted by a wood-burning fireplace and pellet stove, creating cozy gathering spaces in every season. Numerous updates and improvements throughout reflect pride of ownership and add to the home's comfort and functionality. Equally suited as a primary residence, vacation retreat, or investment opportunity, this is a rare chance to own a well-maintained Vermont home with unbeatable ski access, state park-bordered privacy, and direct VAST snowmobile trail access minutes from Londonderry's village & Farmers Market

157 Old Sawmill Rd, Londonderry

494 W River Rd, Londonderry
$445,000
4 Beds ⋅ 2 Baths ⋅ 5093410 MLS
Lucky for the next Buyer that this home is back on market because last buyer could not secure financing! This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added Lochinvar high efficiency propane boiler with on demand hot water installed in November of 2025. The 4 bedroom, 2 bath home has been lovingly cared for by the owners of it for over 25 years. The house has had many updates including cedar shake siding and the first floor windows replaced in 2008. In addition, the two baths were updated and a heated mudroom/sunroom was added. One of the baths features a shower for two with dual shower heads. The living area features a Hearthstone propane stove that turns on with the flip of a switch and looks and heats like a wood-burning stove without the effort. The separate two-car garage also has a loft area. The walk-out basement is huge and offers a regulation slate pool table and ping pong table as well as the laundry area. The West River Trail that is so popular for walking/jogging/biking, and cross country skiing is just a short walk away. Stratton, Bromley and Magic are all within a 20 minute drive.

494 W River Rd, Londonderry

57 Vartland Ridge Rd, Londonderry
$299,000
3 Beds ⋅ 1 Baths ⋅ 5093067 MLS
Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated propane lines in 2020. The deck was also replaced in 2020, creating an inviting outdoor space to enjoy the surrounding setting. The roof was replaced in 2012. A standout feature is the oversized two-car garage, complete with a heated workshop and a slab already plumbed for future radiant heat. Above the garage, unfinished space provides additional flexibility and potential for future living space, office space, studio use, or expanded storage. The current layout includes living space on the main level with two bedrooms sharing a bath, plus an additional upper-level room. Convenient access to VAST trails adds year-round recreational appeal. This property offers a combination of practical improvements, workshop space, and future possibilities for the next owner.

57 Vartland Ridge Rd, Londonderry

3 Faye Ln, Londonderry
$879,900
4 Beds ⋅ 3 Baths ⋅ 5092428 MLS
Welcome to this stunning 4-bedroom Colonial, ideally situated on a peaceful cul-de-sac and set on a beautifully landscaped 1.59-acre lot. Thoughtfully updated throughout. The main level features a welcoming tiled foyer, a spacious living room, a formal dining room, and a beautifully renovated eat-in kitchen showcasing granite countertops, tile flooring, a breakfast bar, pantry, and a bright dining area with French doors leading to an expansive 20' x 36' composite deck. The impressive great room boasts a soaring cathedral ceiling, custom built-ins, and a masonry wood-burning fireplace, creating the perfect gathering space. A convenient first-floor laundry area and updated half bath complete the level. Upstairs, the luxurious primary suite offers a walk-in closet and a beautifully remodeled spa-inspired bath with granite finishes and a glass vessel sink. Three additional generously sized bedrooms, an updated full bath, and convenient attic storage provide ample space for family and guests. The walkout basement offers excellent storage and future expansion potential, while major updates—including the roof, boiler, hot water tank, and central air conditioning—provide peace of mind. Additional features include a portable generator, irrigation system, extra-deep two-car garage and a charming brick-and-granite walkway. Outdoor living truly shines with an exceptional entertaining area featuring a large composite deck, hot tub, pergola, and fully equipped outdoor kitchen—perfect for hosting gatherings or relaxing in your private backyard retreat. Framed by beautiful landscaping and a classic stone wall, this remarkable property offers privacy, comfort, and outstanding curb appeal in a highly desirable setting.

3 Faye Ln, Londonderry

5735 Vt Route 11, Londonderry
$450,000
4 Beds ⋅ 4 Baths ⋅ 5091606 MLS
What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate?  You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market!  Sellers are motivated due to having already relocated for work!  Historical authenticity has not been sacrificed in their successful pursuit of modern comfort:  the tasteful remodeling of the kitchen, bathrooms, floors, ceilings, and more won't distract from your delight in the rustic touches left intact or even improved upon.  Luxuriate in central AC, a true Vermont rarity, when you come in from your work in the expansive 2-floor garage/barn, chicken coop, or on the grounds graced by a lovingly cared for orchard beside a scenic private pond.  Did we mention the orchard?  Apples, peaches, pears and cherries dot the landscape, an arborist's dream, with gorgeous mountain views in the distance!  Nestled in the desirable town of Londonderry, you have access to year-round amenities at a level not found in every ski town: it's home to Magic Mountain, and a short drive away from Bromley, Stratton, and Okemo.  In the warmer months, enjoy gorgeous 102-acre Lowell Lake, its state park and its islands just minutes away!  While newly-planted arbor vitae promise to shoot up quickly and reduce the highway noise, the house sits comfortably above Vermont Route 11, a road offering pleasant drives between ski towns.  Once you're inside or in your backyard, you may be surprised how quickly you forget about the world going by and remember to be glad you bought this diamond-out-of-the-rough.  Sold largely furnished!  Inquire today while it's still available!

5735 Vt Route 11, Londonderry

2170 N Main St, Londonderry
$675,000
5091253 MLS
For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that provide steady residential income. Positioned directly on a main road with excellent traffic exposure, the property benefits from continuous visibility and easy access, supporting both the commercial tenants and future growth potential. Whether you’re an investor seeking diversified revenue streams or an owner-operator looking to step into a turnkey, multi-income asset, this property offers immediate cash flow with room to expand, modernize, or reposition for even greater returns.

2170 N Main St, Londonderry

7 Lily Ln, Londonderry
$990,000
3 Beds ⋅ 3 Baths ⋅ 5087313 MLS
Welcome to Winni Estates, South Londonderry's newest 21-lot development by DHB Homes featuring both first and second floor primary suite options. Open concept floor plans, large windows, tall ceilings, light or dark interiors, crisp and cool exterior color schemes, designer-inspired finishes, custom cabinetry options, sleek quartz countertops, stunning tile selections - the chance to make our brand new builds your new home at every turn. Winni Estates is where the essence of modern residential living meets the timeless charm of a small town. Common areas featuring a park and a recreation field, where all residents can gather with family and friends for a birthday party or a game of soccer. Walking trails throughout giving all homeowners the ability to connect with nature. Set amongst the trees but close to everything Londonderry has to offer - easy highway access to Exit 4, I-93, top-rated schools, shopping and restaurants. Tour our model home and other builds under construction and experience all of the beauty and uniqueness that Winni Estates has to offer! *Use 22 Young Road for GPS location.

7 Lily Ln, Londonderry

26 Wedgewood Dr, Londonderry
$689,900
3 Beds ⋅ 3 Baths ⋅ 5083727 MLS
*Quick Close Available* Among the gently curving neighborhood streets of North Londonderry, this well renovated extended cape is looking for its new owner! While the current residents are moving on, they have put in extensive efforts to modernize and improve the functionality. Of course the expected upgrades are here in the new kitchen with custom backsplash tile and leathered granite counters, hardwood floors, completely renovated bathrooms, and modern paint colors throughout. On the outside, there is brand new vinyl siding in 2026 and new windows in 2023. Above and beyond, it is a welcome surprise to find a complete smart home ready setup and standby generator to wait out dreaded winter power outages in style. All of these enhancements only complement the home's natural charm, unique architectural appeal, and features, such as multiple living rooms, home office, bonus room, eat-in kitchen, primary suite, 1 acre lot, fenced in backyard, and two car garage. All of this in a quiet, side street neighborhood that is only minutes from rt.102 amenities, rt.93, and Manchester. *Agent interest*

26 Wedgewood Dr, Londonderry

6795 Vt Route 100, Londonderry
$339,000
4 Beds ⋅ 3 Baths ⋅ 5077737 MLS
Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to return it to a spacious home with 4-bedrooms, or start your own thriving business venture. The building's furnace keeps the winters warm and the summers with central air conditioning ensure year-round comfort. This property features plenty of parking, making it ideal for commercial use or family gatherings. A true highlight is the large, historic waterwheel barn, providing a space with endless potential for creative projects or storage. If you’re a handy person, the barn is a perfect opportunity for a workshop. Whether you're looking to settle into a quiet country home or embark on your next business adventure, this property is a rare find in picturesque Southern Vermont. Don’t miss your chance to own a slice of Vermont. Schedule a showing today and explore the possibilities! There are 4 pictures that are virtual renovations of rooms in the house.

6795 Vt Route 100, Londonderry

4669 Vermont Rte 100, Londonderry
$1,498,500
7 Beds ⋅ 5 Baths ⋅ 5077331 MLS
Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town’s blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ventures. A separate barn includes a woodworking shop. In recent years, pastureland surrounding the home and pond was reclaimed for grazing goats, restoring the agrarian rhythm of the property. Wildflowers and apple trees scatter the fields. A three-quarter-mile hike through the wood reveals a cool swimming hole. Additional woodland trails invite walking, snowshoeing, and foraging for berries, mushrooms and fiddleheads. Timberland Farm is a legacy holding, and very private, yet within easy reach of Stratton, Bromley, Magic Mtn. and Okemo. 17 miles from Manchester and 26 miles from Rutland Airport. 3 h from Boston and 4 h from New York. No showings through May 16th, 2026. Showings are by APPOINTMENT ONLY. Do not drive up the driveway to view the property. Home is owner-occupied and surveillance is in effect.

4669 Vermont Rte 100, Londonderry

3148 Rte 11, Londonderry
$549,000
3 Beds ⋅ 2 Baths ⋅ 5074646 MLS
More than a Vermont home, this is a property built for the way you want to live here. Set on 14 acres in Londonderry, this versatile Southern Vermont property combines a 3-bedroom, 2-bath home with something increasingly difficult to find near the mountains: acreage, substantial storage, multiple outbuildings and room for all the gear that comes with the Vermont lifestyle. The property features a 3-bay pole barn, 1.5-bay garage and additional outbuildings surrounded by mostly wooded acreage with open areas to enjoy. Inside, the 1,944-square-foot home offers three bedrooms, two full baths, a spacious living room, separate dining room and a bonus room with its own exterior entrance, ideal for a home office, studio or flexible workspace. Multiple porches and decks extend the living space outdoors, while the hot tub provides the perfect place to unwind after a day on the mountain. And the location puts four-season recreation within easy reach. Bromley, Stratton, Magic and Okemo are all accessible from your Southern Vermont basecamp, along with hiking, biking, snowmobiling, fishing, golf and everything else the Green Mountains offer. Whether you're searching for a full-time Vermont residence, mountain getaway, recreational property or simply a home where there's finally enough room for the skis, bikes, sleds, tractor, workshop and outdoor gear, 3148 Route 11 deserves a closer look. 14 acres. Mountain access. Room for everything. Schedule a private showing and come experience the possibilities for yourself.

3148 Rte 11, Londonderry

135 Overlook Dr, Londonderry
$425,000
5 Beds ⋅ 3 Baths ⋅ 5070340 MLS
Investment opportunity! This beautiful ski country compound offers 3 potential streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped with their own kitchen and come with paying tenants. Keep the property in its current configuration, or combine the main house into one living area, with the barn as an in-law suite. A septic design exists for a subdivision of the property which, if the subdivision is obtained and a septic permit approved, would enable further development. Property to be sold as-is. Owner financing available.

135 Overlook Dr, Londonderry

2072 N Main St, Londonderry
$299,000
5069109 MLS
This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths on the second floor. Should you choose to live in all or part you would be close to skiing at Bromley, Magic, Okemo and Stratton as well as nearby shopping/dining in Weston and Manchester. If you like outdoor activities you would have most options near by including hiking, biking and horseback riding. There are separate utilities and some updates have been done including a new furnace and hot water heater on the residential side. There is currently on site septic but there is an approved application in place for town sewer.

2072 N Main St, Londonderry

341 Under The Mountain Rd, Londonderry
$600,000
5 Beds ⋅ 3 Baths ⋅ 5053705 MLS
Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly spacious rooms perfect for entertaining and family gatherings. Wide pine floors, antique fireplaces, and original glazed windows add warmth and charm throughout. The main level features a large primary bedroom suite, while four additional bedrooms and a full bath upstairs provide plenty of space for guests. A cozy recreation room with a grand fireplace or the sauna is perfect for apres-ski evenings, and a separate dining building offers a private space ideal for hosting dinners or working from home as a dedicated office or studio. Outdoors, enjoy peaceful walks through the forest along an old logging road, fish or relax by your own large private pond, and take in the serene beauty of the countryside. A detached 3-car garage adds extra convenience and storage for outdoor gear or snowmobiles. Just a short drive from top ski resorts and year-round activities including hiking, biking, and nearby lakes, this Vermont farmhouse is the perfect mountain retreat.

341 Under The Mountain Rd, Londonderry

3715 Rte 11, Londonderry
$755,000
5 Beds ⋅ 3 Baths ⋅ 5061900 MLS
Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale lighting and bath fixtures. Located in the heart of ski country with views of Magic Mountain and just minutes from Magic, Bromley, and Stratton, this is a home for the outdoor enthusiast. A large pond in the backyard invites swimming, canoeing, and paddleboarding, while the expansive back deck overlooks the water--perfect for outdoor dining and entertaining. Upstairs bedrooms feature custom built-ins, and the primary suite --set in its own wing--boasts cathedral ceilings, a beautiful bath, and serene pond views. The well-planned gear room includes ample closets, cubbies, and hooks to keep outdoor essentials organized. Pet-friendly with a fully fenced backyard, custom dog cubbies, and a pet shower. Tesla EV charger included. The vintage barn offers flexible space for storage and an opportunity for another area to entertain. Live your best Vermont life in comfort, style, and natural beauty.

3715 Rte 11, Londonderry

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