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Londonderry VT Real Estate

In the southern Vermont region of Windham County, the town of Londonderry is a small, rural area with a peaceful, close-knit community. Londonderry is home to Magic Mountain, a ski resort that provides year-round activities for its residents and visitors as well as supports the local economy. Within close proximity to Stratton and Bromley Mountains, Londonderry is a perfect town for those who want to live in the countryside while still having access to all the recreational activities in the area. 

Search the latest real estate in Londonderry, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ​Register to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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207 Brooks Lane Londonderry VT 05148

Londonderry, VT207 Brooks Lane

Price$2,475,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4971327

  • Residential Single Family
  • Full Bath 6
  • Address 207 Brooks Lane
  • Construction Existing
  • Bedrooms 9

This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it offers ample space for everyone to convene while relishing their individual, private retreats. The main house, steeped in history dating back to 1820, is a delightful 3-bedroom brick farmhouse showcasing a generous 45-foot-long great room that seamlessly extends to a covered patio adorned with an awning, a idyllic setting for outdoor gatherings. The newly renovated kitchen, with granite countertops, serves as the heart of the home, combining modern elegance with timeless charm. The guest cottage features an additional three bedrooms, a cozy living room, and a well-appointed kitchen with an adjoining dining area. Adjacent to the guest cottage, a spa facility awaits, boasting a ground-level private gym, sauna, and an outdoor hot tub. Ascend to the second floor to discover two bedrooms, each with a private bathroom and a shared balcony. Nestled at the property's edge, overlooking the serene swimming pond with a beach, is a rustic cabin complete with a welcoming wood-burning stove and a lofted sleeping area. Ideally suited as a family compound, this retreat offers both separation and privacy

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

732 Under The Mountain Road Londonderry VT 05155

Londonderry, VT732 Under The Mountain Road

Price$1,400,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5009012

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

Londonderry's Under the Mountain Road is one of the area's most beautiful country roads, meandering along the lower western edge of Glebe Mountain, home to Magic Mountain Ski Area and thousands of acres of conserved lands. Here you'll find Fairmount, one of Londonderry's cherished historical properties, featuring one of - if not THE - best view in southern Vermont, with panoramic views looking over the West River Valley to the majestic Green Mountains between Stratton and Bromley. The c.1810 farmhouse was thoroughly and thoughtfully renovated in 1987 and offers historic architectural details that are now integrated into a more contemporary layout, all with an eye to maximizing the interior spaces while enjoying outdoor areas, perennial gardens, and spectacular four-season views. The spacious 5BR house offers a traditional floorplan with rooms to gather in and others to relax and enjoy quiet time - perhaps by the fire in winter months or in the charming “Summer Room” during the warmer months. An adorable but rustic one-bedroom guest cottage is nearby; and there are barns and sheds for vehicles, tools and gear (or animals). The 42+ acre parcel is enrolled in VT's Current Use program for managed forestry and enjoys reduced property taxes. Londonderry is a special community and you'll be just a few miles from the farmer's market, outdoor recreation ranging from hiking and biking, to kayaking at nearby Lowell Lake, to skiing at four major ski areas. Make this special spot yours!

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3928 Vt Route 11 Londonderry VT 05148

Londonderry, VT3928 Vt Route 11

Price$1,200,000The price has recently decreased

MLS Number 5020635

  • Commercial
  • Address 3928 Vt Route 11
  • Year Built 1949
  • Square Feet 2,136
  • Acreage 1.06

Great opportunity, great location. If it is time to "bust a move,” "ditch the grind" of the city, or expand your Vermont business enterprises... either way or whatever the reason, this "up and running" turn-key business is ready to be supercharged. Everything is new, updated, or upgraded. Business is good. Very strong "local" following and essentially at the base of Magic Mtn ski area, and on Rt 11 just outside Londonderry, you are in a PRIME location to capture and generate huge traffic. Terrific ambiance and atmosphere, locals and seasonal/weekend guests alike all enjoy the camaraderie, casual surroundings and delicious foods. Whether for a great family dinner or an apres ski beer and snack, this is a superb choice. 2 pizza overs have produced award-winning pizza here, some of the best pizza in Southern Vt! Also on the VAST snowmobile trails network, another opportunity to build collateral revenue streams. With a restaurant that seats 50 and a bar that seats 25 and a full kitchen that can also produce breakfast, lunch, dinners and take out.. there is NO ceiling to upside revenue potential. This is what YOU will make it. Wide open potential. Financials available after a first showing only! POS sale system and all inventory included in sale. All licenses and inspections are up to date. Potential living quarters upstairs, small apartment.This is a move-in ready; take it over and take on the opportunity!

Listed by Wilkie Bushby of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

359 Chaves Road Londonderry VT 05148

Londonderry, VT359 Chaves Road

Price$975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5001159

  • Residential Single Family
  • Full Bath 2
  • Address 359 Chaves Road
  • Construction Existing
  • Bedrooms 5

Experience the best of Vermont in this private mountain retreat, perfectly located near Magic, Bromley, Okemo, and Stratton Mountains for skiing, as well as cross-country trails and Lowell Lake. Situated on 36 picturesque acres, the driveway winds past a neighboring pond to reveal a home with a level grassy yard, perfect for lawn games and evenings around the fire pit. This 5-bedroom expanded cape boasts breathtaking views from multiple rooms and an expansive deck. The formal entry features a sweeping staircase leading to a front-to-back living room with hardwood floors and a tremendous stone fireplace. The spacious kitchen includes a sunny breakfast nook with a pellet stove and glass doors leading to the deck. This floor also hosts a gathering room, dining room, plus a main floor bdr for convenience. Upstairs, find 4 more bedrooms, including two suites with private baths and a sitting area that overlooks the pond and mountain vistas. Primary bedroom includes a bonus room with a gas fireplace & mini split with heat & a/c, ideal for an office or yoga space. A lower level offers ample entertainment room with a bar, pool table, and bath. Recently repainted, new hardwood floors, and a newer roof, this home is move in ready! With potential for rental income or tax benefits from the VT Current Use program, the possibilities are endless. A year round retreat!

Listed by Julie Citron and David Citron of RE/MAX Four Seasons

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2170 North Main Street Londonderry VT 05148

Londonderry, VT2170 North Main Street

Price$900,000The price has recently decreased

MLS Number 4997377

  • Commercial
  • Square Feet 6,144
  • Acreage 1.84
  • Area VT-Windham
  • PricePerSqFt 146.48

For the first time in 25 years, a cherished Londonderry, VT institution is up for sale, presenting an incredible opportunity for both investors and owner-operators. This property, steeped in local history, has been thoughtfully renovated and updated with modern systems by the current owner, ensuring a seamless transition for the next proprietor. The property boasts a long-term lease on a popular diner and a charming country store, both well-established and beloved by the community. Above these commercial spaces are two residential units, perfect for generating additional income or housing staff. The first unit is a three-bedroom, one-bathroom apartment, offering ample living space and comfort. The second unit is a cozy two-bedroom, one-bathroom apartment, ideal for a small family or as a rental property. This unique offering is a rare gem, combining commercial and residential potential in a picturesque Vermont setting. Don't miss this extraordinary chance to own a piece of Londonderry's heritage and secure a versatile investment with multiple revenue streams.

Listed by Britt Wohler and Kim Morgan-Wohler of Wohler Realty Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3806 B Vermont Route 11 Londonderry VT 05148

Londonderry, VT3806 B Vermont Route 11

Price$899,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5020518

  • Multifamily
  • Units 20
  • Acreage 3.6
  • Square Feet 7,902
  • Area VT-Windham

This property features a 18-unit motel, that includes two apartment suites, alongside a spacious 3-bedroom, 2-bathroom home, making it a unique investment opportunity. Situated in the charming town of Londonderry, this property is perfectly positioned to attract visitors year-round with its proximity to two of Vermont's most popular ski destinations-Okemo Mountain Resort and Stratton Mountain Resort, offering prime income potential. Okemo Mountain Resort, just a short drive away, is renowned for its friendly atmosphere, extensive trail system, and top-notch snow conditions. Whether guests are avid skiers or simply looking to enjoy the winter scenery, Okemo provides a wide range of activities including skiing, snowboarding, and snowshoeing. Stratton Mountain Resort, also within easy reach, offers a slightly different experience with its charming village, diverse terrain, and vibrant apres-ski scene. In addition to winter sports, Stratton is a four-season destination with golf, hiking, and mountain biking opportunities during the warmer months. The motel's proximity to these popular destinations and the combination of commercial and residential spaces presents a lucrative opportunity in a sought-after location.

Listed by Flex Realty Group and Grayson VanHendrick of Flex Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3806 Vt Route 11 Londonderry VT 05148

Londonderry, VT3806 Vt Route 11

Price$899,000The price has recently decreased

MLS Number 5009309

  • Commercial
  • Address 3806 Vt Route 11
  • Year Built 1962
  • Square Feet 7,002
  • Acreage 3.6

This property features a 18-unit motel, that includes two apartment suites, alongside a spacious 3-bedroom, 2-bathroom home, making it a unique investment opportunity. Situated in the charming town of Londonderry, this property is perfectly positioned to attract visitors year-round with its proximity to two of Vermont's most popular ski destinations-Okemo Mountain Resort and Stratton Mountain Resort, offering prime income potential. Okemo Mountain Resort, just a short drive away, is renowned for its friendly atmosphere, extensive trail system, and top-notch snow conditions. Whether guests are avid skiers or simply looking to enjoy the winter scenery, Okemo provides a wide range of activities including skiing, snowboarding, and snowshoeing. Stratton Mountain Resort, also within easy reach, offers a slightly different experience with its charming village, diverse terrain, and vibrant apres-ski scene. In addition to winter sports, Stratton is a four-season destination with golf, hiking, and mountain biking opportunities during the warmer months. The motel's proximity to these popular destinations and the combination of commercial and residential spaces presents a lucrative opportunity in a sought-after location.

Listed by Flex Realty Group and Grayson VanHendrick of Flex Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

393 & 441 Magic Mountain Access Road Londonderry VT 05155

Londonderry, VT393 & 441 Magic Mountain Access Road

Price$749,000The price has recently decreased

MLS Number 5010908

  • Commercial
  • Year Built 1963
  • Square Feet 27,404
  • Acreage 2.05
  • Area VT-Windham

Investment Opportunity in Londonderry, VT! Discover the potential of this Alpine-style lodge, perfectly situated on Magic Mountain, just 300 feet from the ski lifts and slopes. This property, while needing extensive renovation or demolition, offers incredible value with options for redevelopment. The house, likely salvageable, is connected to a community sewer and one of the two private well. The hotel and annex present an ideal gut job or tear-down project, making way for future building lots. Note: Asbestos is present in the bathroom tiles and ceilings. Magic Mountain holds the right of first refusal. Don't miss this chance to create something truly special on this prime, almost, ski-in/ski-out property!

Listed by Carrie Mathews of Winhall Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

000 Under The Mountain Road Londonderry VT 05155

Londonderry, VT000 Under The Mountain Road

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4996771

  • Land
  • Acreage 45
  • Area VT-Windham
  • Utilities Phone, Satellite
  • PricePerSqFt 15000

Travel down a quiet, tree-lined country road past historic homes, horse farms, and a large nature preserve to discover this magnificent property with views of Stratton and Bromley mountains in the distance. A large open field graced with wild flowers, apple trees and classic Vermont rock walls provides an ideal level home site, protected on three sides by extensive mature woods. The parcel has a state permit for a large single family residence with power available on site and fiber optic internet recently strung at the road. Just a few minutes' drive to Magic Mountain, Lowell Lake, the West River Farmers Market, and the shops and restaurants of Londonderry, this property will support country living at its best. View the photos and video, then come see it in person before it's gone!

Listed by Steve Stettler of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

659 Magic Circle Londonderry VT 05148

Londonderry, VT659 Magic Circle

Price$599,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5006399

  • Residential Single Family
  • Full Bath 1
  • Address 659 Magic Circle
  • Construction Existing
  • Bedrooms 5

A genuine marvel of expansive design, this Magic Mountain property is characterized by its soaring ceilings and an inviting, grand entryway that extends to the second floor. Discover the allure of this extensive estate, featuring 5 bedrooms, an oversized two-car garage, multiple living areas, and much more. Ascend to the second floor, where a generous living and dining area awaits, complete with sliding doors that lead to a secluded deck. Adjacent to these rooms is a sizeable kitchen, boasting ample cabinet space, a large center island, and a counter seating area. The upper floor houses three bedrooms and a full bath, including a master bedroom suite that offers a private bath, substantial closet space, and access to a balcony deck with views of the yard. Descend via one of two staircases to the first floor, where a spacious family and game room beckons with a pool table, seating area, and an array of games for post-skiing entertainment. This level also includes two additional bedrooms, one of which is a "bunk room" outfitted with bunk beds to accommodate all guests. Adjacent to the main entrance is a dedicated ski storage room, perfect for hanging and drying gear. The property also features a full-house generator, a pellet stove, and ample space for everyone to unwind. HOA fees ensure well-maintained roads and a community water system, billed separately. This home is sold furnished, ready for you to enjoy the upcoming ski season with everything you need! Video available.

Listed by Ernie Rossi of Rossi & Riina Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

132 Pingree Park Lane Londonderry VT 05148

Londonderry, VT132 Pingree Park Lane

Price$539,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5016405

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Follow a private country lane to this secret location. Adjacent to Pingree Park, this hidden gem is quietly situated on a lovely parcel of land. Find seclusion within a short distance to the Londonderry town center. Next to Pingree Park, its almost like having your own recreation area! First time on the market, the original home is a 3 bedroom, 2 bath . The recent addition adds another 1300 sq feet and needs only interior finishing to your specifications. Live in the main house while construction is going on. The large main floor of the addition has top quality construction, lots of natural light and an open floor plan. The space above will make a stunning primary suite. The 3 car garage has radiant heat and direct access to the house and is ready to use. Exceptional work shop area! The stone walls, pretty gardens and well designed deck and porch spaces create a fun home for all seasons. With a pretty brook and close river access this unique location has a lot of offer! The original 10 acres is being divided into 4 total lots, so additional land is available if desired. This home is convenient to Stratton, Magic, Okemo and Bromley, all within a 20 minute drive. Great proximity to Manchester and to Weston for summer theater and fine dining. Enjoy country living in a beautiful, natural setting. make an appointment to see this home today!

Listed by Alison Cummings of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2072 North Main Street Londonderry VT 05148

Londonderry, VT2072 North Main Street

Price$464,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 5009298

  • Residential Single Family
  • Full Bath 4
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5

Prime Downtown Londonderry VT Property: Versatile 6-Bedroom Home or 2 unit rental income property!! One residental and one commercial all ready to go! Discover the charm of downtown Londonderry with this exceptional property situated on Main Street, directly across from Jelley's Beer and Wine Liquor Store and conveniently close to local grocery stores, restaurants, and more. This versatile 6-bedroom, 4.5-bath home features elegant hardwood flooring throughout and two cozy wood-burning fireplaces, perfect for any season. Designed for flexibility, this property offers separate living quarters with a private entrance ideal for guests or rental opportunities. Zoned for both commercial and residential use, it provides the unique advantage of accommodating up to 12 people comfortably, making it a fantastic investment or family retreat. In winter, enjoy quick access to renowned ski resorts such as Stratton, Killington, and Bromley. Explore Manchester Center for premier shopping experiences or take advantage of the nearby snowshoeing and cross country ski trails. During the summer and fall, indulge in outdoor activities like kayaking, hiking, leaf-peeping, and apple or berry picking. This property stands out as a year-round destination with its blend of convenience, comfort, and recreational opportunities. Note: Bonded restrictions apply. Explore the possibilities of this remarkable downtown Londonderry Diamond in the Rough today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated December 6, 2024 8:09 AM EST

 

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