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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
  • Construction Existing
  • Bedrooms 9
  • Bathroom 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: 6.35% last updated on 2024-09-05

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

207 Boynton Road Londonderry VT 05148

Londonderry, VT207 Boynton Road

Price$1,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5002885

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

Looking for gracious family living in a spectacular private setting with mountain views, within a short drive of four ski resorts? Midway between the attractions of Weston and the amenities of Londonderry, this architect designed home has been upgraded, expanded and scrupulously maintained by its present owners. Spread out on the main floor with its cathedral ceilinged living room, open concept dining room and kitchen, cozy sunroom, handsome study, and spacious primary suite with fireplace, two walk-in closets, and spa-like bath. Your family and friends will be comfortably accommodated on the other two floors: two bed rooms with ensuite baths upstairs, and a rec room/game room, kitchenette, bedroom and full bath on the walk-out lower level. Full of light and designed to take advantage of the stunning view from most every room, the house has central air conditioning, high speed internet, a security system, and a heated 2-car garage. Savor morning coffee, relaxing cocktails or al fresco dinners on the decks overlooking the landscaped grounds and pond with the four season splendor of the Green Mountains in the distance. A post and beam barn provides two more bays, a workshop space, and a lofty second floor for added storage or expansion. The sellers have longtime caretakers who service the property all year long. Come tour this beautiful Vermont retreat in person and make it the home of your dreams. Furnishings negotiable; all measurements approximate. No drive-bys, please.

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: 6.35% last updated on 2024-09-05

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

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: 6.35% last updated on 2024-09-05

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

1778 Hells Peak Road Londonderry VT 05148

Londonderry, VT1778 Hells Peak Road

Price$1,249,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5012494

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4

Nestled on 10 picturesque Vermont acres, this pristine 1989 Colonial offers the perfect blend of classic elegance and modern comfort. The property boasts 6 spacious bedrooms, 4 well-appointed baths, and 5 stunning brick fireplaces that exude warmth and character throughout. The expansive island kitchen, complete with a walk-in pantry, is a chef's delight, ideal for entertaining or preparing family meals. Additional features include a dedicated home office, a game room for recreation, a two-car garage, an inviting outdoor hot tub for relaxing under the stars, and a private basketball court for sports enthusiasts. Outside, the tranquil pond and rolling landscape create a serene setting, making this home a true retreat from the hustle and bustle of everyday life. Showings begin on Friday 9/6/24 at the open house from 12-2:00 pm. Additional open house Sunday 9/8/24 from 11am-1pm. Watch the video for a glimpse inside this spectacular home.

Listed by Lavinia Lee Brown and Nancy Jensen 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: 6.35% last updated on 2024-09-05

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

450 Deerwood Hill Road Londonderry VT 05155

Londonderry, VT450 Deerwood Hill Road

Price$999,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5003114

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Nothing but Superlatives to describe this Gorgeous Home. Perfect Location. Stunning Grounds. Immaculate condition.This 4 bedroom home is immaculately maintained. Gorgeous Post 'n Beam Vermont Cape in perfect location to enjoy all that Southern Vt has to offer. Close to Stratton, Magic, Bromley, Okemo, Manchester shopping, golf, mountain biking, swimming and canoeing on Lowell Lake.. all within 5-20 mins. Amazing stone patio, in ground hot tub, 4 season screened-in heated cabana with rear projection TV with oversized tv/movie screen for amazing outdoor/indoor entertaining. Patio area large enough to have a grand gathering.. or just a few friends over for a BBQ in perfectly peaceful Vt setting. The house is in mint shape, gourmet kitchen, country sink, beautiful Danby Vt. marble counter tops, top of the line stainless appliances, gas stove..very large cozy living room with wood burning fireplace, deck just off LR, primary bedroom on main floor, cathedral ceiling and fan, large formal dining area, wine cellar. Huge family room for TV games area downstairs that opens up to outside patio entertaining cabana and pristine hot tub. Loft with office area for additional area to study or compute. High fidelity Sonos 10 speaker indoor/outdoor stereo system. Central vacuum system.The grounds are meticulously planted and maintained with annuals and seasonals all currently in full bloom and stunning. Come and see this beautiful home. Open House 7/6 11am-1pm All welcome!

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: 6.35% last updated on 2024-09-05

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
  • Construction Existing
  • Bedrooms 5
  • Bathroom 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

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: 6.35% last updated on 2024-09-05

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
  • 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

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: 6.35% last updated on 2024-09-05

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
  • Year Built 1962
  • Square Feet 7,002
  • Acreage 3.6
  • PricePerSqFt 128.39

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: 6.35% last updated on 2024-09-05

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

340 Melendy Hill Road Londonderry VT 05155

Londonderry, VT340 Melendy Hill Road

Price$885,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5006536

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

Nestled on a picturesque 40-acre estate in desirable South Londonderry, Vermont, this luxurious property offers an unparalleled blend of tranquility and convenience. Between a 10-15-minute drive to Stratton, Magic Mountain, and Bromley, this exquisite residence is an ideal choice for a primary home, vacation retreat, or investment as a short-term rental. The main residence features three spacious bedrooms, each bathed in natural light, along with two elegantly appointed bathrooms. The living area boasts a stunning stone fireplace, perfect for cozying up on winter nights. The expansive three-season porch, adorned with large windows, offers breathtaking views of Glebe Mountain Magic and the surrounding area making this an ideal space for relaxation or entertaining guests. Outside, the property includes a massive two-story barn, equipped with a 3-phase converter for machinery, this space has endless possibilities. The post and beam tranquility lodge on the property adds a touch of rustic elegance, while two storage sheds provide ample space for all your needs. With year-round hiking and cross-country skiing trails weaving through the property, outdoor enthusiasts will find this estate a dream come true. Discover the perfect blend of luxury and natural beauty in this exceptional Vermont property.

Listed by Leo Pond of Blue Ridge 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: 6.35% last updated on 2024-09-05

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

3590 Vt Route 100 Londonderry VT 05155

Londonderry, VT3590 Vt Route 100

Price$795,000The price has recently decreased

MLS Number 5002074

  • Commercial
  • Year Built 1900
  • Square Feet 2,641
  • Acreage 0.74
  • PricePerSqFt 301.02

Retail space renovation 2011 and apartment 2018. This building was once the Home of Hayes Snowboards! Come see this great building and bring your ideas! Store front with 1260 SF retail store space and 925 SF cold storage abutting main building. Just off the offices is a wonderful one bedroom apartment. Beautiful wood floors throughout. Live in or rent the apartment space. Building is mixed use. Rental income for apartment possible!

Listed by Bob Maisey 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.35% last updated on 2024-09-05

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

384 Adams Drive Londonderry VT 05148

Londonderry, VT384 Adams Drive

Price$750,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5001337

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

Centrally located, this well-maintained contemporary is tucked away at the end of the lane and offers a quiet respite and complete privacy, and yet is just minutes away from the best farmer's market in Vermont, multiple ski areas (large and small), Lowell Lake for hiking and kayaking, fine and casual dining, shopping, school, medical center and more. The house features a convenient and comfortable layout, central A/C, whole-house generator, and Maple flooring throughout the ground level. The main living areas are on the ground level - guest entry, custom kitchen with marble counters and stainless appliances, dining area with a gorgeous white marble fireplace, sunny and spacious living room with woodstove, den/office, bathroom with shower and laundry room. Upstairs, there are four bedrooms including a large primary suite with walk-in closet and private bathroom with double sinks, jetted tub, and a large walk-in shower; a shared full bath; and a small, cozy room that could be used for extra closet space or make it a secret reading nook. Outside, you'll find a wide patio running the length of the house with a built-in gas firepit, raised garden beds, colorful but no-fuss perennial gardens, and a wide level lawn for fun and games. There is an attached two-car garage with direct entry and two sheds for all of your tools, equipment, and gear. Londonderry is a dynamic community with a great mix of primary and vacation homes and this neighborhood is no exception . . . make it yours!

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

{$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: 6.35% last updated on 2024-09-05

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
  • PricePerSqFt 27.33

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 William Raveis Winhall

{$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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.35% last updated on 2024-09-05

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

Broker Reciprocity 

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 September 12, 2024 10:59 AM EDT

 

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