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$489,000
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, like the specially-selected Glenwood Modern F Cookstove. Luxuriate in central AC, a 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

$350,000
3 Beds 2 Baths 5090484 MLS
Nestled in the heart of Vermont's scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the cabin features comfortable living spaces, a charming country feel, and the tranquility only Vermont can offer. Whether relaxing by the fire, enjoying crisp mountain air from the porch, or taking in the picturesque surroundings, this enchanting retreat captures the essence of cozy Vermont living. Powder Mill is a unique community designed for the outdoor enthusiast.  Offering direct access to trails, snowmobile routes, scenic ponds, and a welcoming neighborhood feel.   Outdoor recreation can be enjoyed year-round. In the winter, residents and visitors are just a short drive from the renowned ski slopes of Stratton Mountain Resort, Bromley Mountain,  Magic Mountain Ski Area and snowshoeing on Lowell Lake.  During the warmer months, the area offers abundant hiking, walking, and mountain biking trails that showcase Vermont's natural beauty. Swim, fish, canoe or kayak at nearby Lowell Lake.  After a day of adventure, nearby Manchester provides a wide variety of dining options, from casual cafés to fine restaurants, ensuring there's something to satisfy every appetite.

287 Powder Mill Rd, Londonderry

$1,800,000
4 Beds 5 Baths 5087347 MLS
One-of-a-Kind Vermont Lifestyle Property Home, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated, and designed for everyday living. Originally an inn and lovingly reimagined by its current owners, the residence offers comfortable living spaces alongside multiple options for creative use, hosting, or generating income. A separate rental ADU, classic Vermont barn, greenhouse, and expansive grounds bordered by historic stone walls create a setting that feels both private and full of possibility. Adding to the property’s versatility is the space currently home to the nationally recognized SoLo Farm & Table—an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a state-of-the-art kitchen, wood-fired masonry grill, sound-insulated dining rooms, and curated wine display, this space is ideal for a turnkey culinary venture—or could be reimagined as a studio, event venue, workshop, or expanded residential use. Outdoor living is equally compelling, featuring a beautifully designed stone patio with a custom-built whole animal cooker, a hard-wired generator, established growing spaces, and room to gather, create, and unwind. Whether you envision continuing a celebrated culinary destination, cultivating a home-based business, or simply enjoying a distinctive Vermont property with room to grow, this offering presents a rare opportunity to live, work, and thrive in one remarkable setting.

95 Middletown Rd, Londonderry

$539,900
3 Beds 2 Baths 5085907 MLS
* OPEN HOUSE SUNDAY 8/23 11A - 1P* I love Second Chances! Do you love an Older Home? One that has history? One that has been restored & improved? Well, take a peek at this! Once a 1 room school house when built in 1846, has since become a home with so much space. The age on the tax card is 1990's! Set along a desirable stretch of Old Derry Road this antique home offers a versatile and thoughtfully designed layout. Featuring 2 bedrooms 1.5 baths, plus separate office, Large sprawling kitchen couldn't have more charm if it tried! From the color-palette, Wall ovens, island cooktop & Built-in's hidden throughout. Separate dining room, front to back living room & 2nd floor office. Primary bedroom with vaulted ceilings & walk in closet tastefully spaced apart from 2nd bedroom. Hallway lined with bookshelves galore! The home provides the ideal blend of comfort and functionality-perfect for today’s work-from-home lifestyle. A major bonus is the finished space above the garage, offering incredible potential for a 3rd bedroom, game room, hangout area, teen suite, or extra living space-giving you room to grow without outgrowing the home. Step outside to enjoy the fully fenced yard, ideal for pets, play, or relaxing weekends in your own private outdoor space. Conveniently located near shopping, dining, and commuter routes, it’s an excellent opportunity to step into homeownership in desirable Londonderry.

66 Old Derry Rd, Londonderry

$699,900
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

$1,175,000
5 Beds 4 Baths 5078457 MLS
Welcome to 8 Wiley Hill Road! This stunning new construction 5-bedroom, 4-bath Colonial offers exceptional flexibility with a thoughtfully designed first-floor ADU/in-law suite. There’s still time for buyers to personalize many of the finishes, including flooring, kitchen cabinetry, granite countertops, and tile selections, making this a unique opportunity to create your dream home. The main home features an open-concept layout with a spacious eat-in kitchen, formal dining room, and an expansive front-to-back living room centered around a cozy gas fireplace. The first-floor in-law suite offers privacy and independence with its own open kitchen and living area, laundry, primary bedroom, and ensuite bath. This home is ideal for multigenerational living, guests, or extended stays. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with ensuite bath. A large walkout basement provides endless possibilities for future finished space, home gym, media room, or recreation area. Outdoor living is equally impressive with two rear decks overlooking the expansive backyard. The home is set back from the road, with the lot offering privacy, granite walkways and steps, and garden beds. The backyard has ample flat space, ideal for a future in-ground pool, while the gently sloping rear section leads to a charming lowland area perfect for a firepit, gazebo, or peaceful outdoor retreat. This home combines space, versatility, privacy, and customization opportunities in a beautiful setting. Schedule your private showing today and experience all that 8 Wiley Hill Road has to offer.

8 Wiley Hill Rd, Londonderry

$999,900
4 Beds 4 Baths 5077834 MLS
Now, BOM, call Today Londonderry's Best Home Value! Discover an exceptional custom built contemporary home, beautifully updated, meticulously cared for by same owners 42 yrs. From the moment you enter it’s clear, this fine home is a unique blend of careful design, quality craftsmanship, modern comfort. Amazing $250,000 Custom Kitchen, Plus a new: roof, driveway, on-demand generator, new windows, and more! Quality home provides remarkable flexibility, including two primary suites, 1st + 2nd floors, both featuring a custom oversized full bathroom and generous closets. With 3/4+ potential bedrooms, and partially finished rms in L.L. ideal for office, gym, creative hobby spaces. Floor Plan adapts to a wide variety of lifestyle! The gourmet, updated kitchen is a standout feature, designed to impress with its custom finishes, expansive breakfast bar, and abundant workspace perfect for everyday living or hosting memorable gatherings. The adjoining two-story family room showcases a warm fireplace and large windows that fill the space with natural light, creating a warm and inviting atmosphere. Convenience continues with central air conditioning, a first-floor laundry room, and a beautiful blend of quality hardwood, and tile flooring throughout the home. Recent improvements include a newer roof and a newly installed on-demand propane generator, adding peace of mind and efficiency. Outdoor living is just as impressive, featuring a spacious 700 sq ft private deck and an inviting front patio—ideal for relaxing & entertaining! Numerous thoughtful updates throughout the home contribute to its move-in-ready feel, offering the character of a long-loved property with the freshness of one that feels newly built. Enjoy the charm and warmth of wood and soaring ceiling! The current owners have cherished this remarkable home for many years, and now it is ready to welcome its next chapter. Come see all the possibilities and discover the comfort, function, and style this property offers.

4 Windsor Blvd, 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

$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

$555,000
3 Beds 2 Baths 5074646 MLS
Located in picturesque Londonderry, Vermont on 14 spacious acres this home is looking for new owners to make it their own! Conveniently located near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done some updates to the home and property but have left spots for the new owners to still put their own finishing touches on the place! The house is very roomy with 3 bedrooms and 2 bathrooms, a very spacious living room, and separate dining room, and offers several great porches/decks and a hot tub. The house also has a bonus room that could be used as an office with a private outside entrance if you wanted to work from home. The property's 14 acres of mostly wooded acreage also houses a 3 bay pole barn, 1.5 bay garage, and a couple other outbuildings. So many great options and potential in this property-it could make a great primary residence, vacation home, possibly subdivide and make a family compound, or so many other options. Don't let this one get away, schedule your appointment today!

3148 Rte 11, 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

$690,000
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

$795,000
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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