South Londonderry, VT Homes for Sale

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  /34

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  410 Tallwood Cir, Londonderry, VT 05148

  This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
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  /49

  $75,000

  • 3 Beds
  • 3 Baths
  • 2,326 Sq Ft

  92 Founders Hill Rd Unit 5A, Stratton, VT 05340

  Mountain Ridge 5A at Stratton offers a rare opportunity to own a quartershare at the very heart of the mountain. This beautifully designed 3-bedroom, 3-bath residence is one of just seven homes in this intimate community, all thoughtfully positioned steps from the base lodge, gondola, and Stratton Village dining, shopping, and nightlife. Inside, a vaulted great room filled with natural light

  

  Trent Stephens

  Wohler Realty Group

  (802) 521-2464

  92 Founders Hill Rd Unit 5A, Stratton, VT 05340
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  /8

  $275,000

  • Land
  • 34.53 Acres
  • $7,964 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /11

  $495,000

  • Land
  • 68.89 Acres
  • $7,185 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /7

  $195,000

  • Land
  • 15.27 Acres
  • $12,770 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /15

  $650,000

  • Land
  • 51.93 Acres
  • $12,517 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /31

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

  148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit

  Andrew King Stratton Real Estate

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
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  /20

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 1,800 Sq Ft

  56 Shattarack Rd Unit D6, Stratton, VT 05360

  Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

  Kim Morgan-Wohler Wohler Realty Group

  56 Shattarack Rd Unit D6, Stratton, VT 05360
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  /32

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  8 Silver Birch Rd Unit 8, Winhall, VT 05340

  Remarkable 3BR Birch Hill Value!Exceptional three-bedroom, two-bath end unit at Birch Hill! This well-thought-out floor plan is a true standout, providing two distinct living areas ideal for entertaining guests or relaxing after a day on the slopes. Features include an updated kitchen and dining space, two modernized baths, and a practical, renovated mudroom—essential for storing all your

  Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  8 Silver Birch Rd Unit 8, Winhall, VT 05340
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  /33

  $1,760,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

  Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

  Edwin Kevil Stratton Real Estate

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
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  /52

  $1,725,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  122 Sunbowl Ridge Rd, Stratton, VT 05360

  Solstice has long been considered the very finest townhome development at Stratton Mountain. With an unparalleled slope side location and private amenities such as heated pool and tub , private shuttle service. This four bedroom four bath townhome is the ultimate ski and summer getaway. Beautifully redone. One car heated garage, family room.

  John Sikes Stratton Real Estate

  122 Sunbowl Ridge Rd, Stratton, VT 05360
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  /51

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /59

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  23 Valley View Rd, Winhall, VT 05340

  Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

  Kim Morgan-Wohler Wohler Realty Group

  23 Valley View Rd, Winhall, VT 05340
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  /31

  $435,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  /59

  $1,300,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  51 Village Square, Stratton, VT 05360

  Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

  Kim Morgan-Wohler Wohler Realty Group

  51 Village Square, Stratton, VT 05360
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  /56

  $2,999,000

  • 6 Beds
  • 6.5 Baths
  • 6,650 Sq Ft

  25 Mountain Haunts Rd, Winhall, VT 05340

  Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

  Kim Morgan-Wohler Wohler Realty Group

  25 Mountain Haunts Rd, Winhall, VT 05340
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  /54

  $2,050,000

  • 4 Beds
  • 4.5 Baths
  • 2,486 Sq Ft

  97 N Brookwood Rd, Stratton, VT 05360

  Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  97 N Brookwood Rd, Stratton, VT 05360
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  /43

  $890,000

  • 5 Beds
  • 4 Baths
  • 2,238 Sq Ft

  8 E Birch Rd Unit 103, Stratton, VT 05360

  Rare 5BR/4BA Stratton Townhome | Ski-Back Access | Designer Furnished | Spacious, fully renovated 5-bedroom, 4-bath townhome at Stratton with ski-back access. Professionally designed and furnished by ACK Design, this move-in-ready home blends mountain charm with modern finishes. The main level features hardwood floors, a stunning floor-to-ceiling stone fireplace, and a granite kitchen with

  Cheyanne Pugliese

  8 E Birch Rd Unit 103, Stratton, VT 05360
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  /9

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vermont 30, Jamaica, VT 05343

  Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

  Helen Nault

  4441 Vermont 30, Jamaica, VT 05343
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  /15

  $485,000

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  49 High Point Dr Unit A-14, Stratton, VT 05360

  49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

  Andrew King Stratton Real Estate

  49 High Point Dr Unit A-14, Stratton, VT 05360
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  /37

  $730,000

  • 5 Beds
  • 3 Baths
  • 2,635 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  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

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
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  /25

  $385,000

  • Land
  • 41.1 Acres
  • $9,367 per Acre

  00 Ross Rd, Winhall, VT 05340

  Welcome to 41.1 acres of quintessential Vermont beauty, ideally located between downtown Manchester (11 minutes), Bromley Mountain (6 minutes), and Stratton Mountain (15 mins). This property offers the best of both worlds—easy access to town, ski mountains, and year-round recreation, yet a peaceful and private setting surrounded by nature. The land features a meandering stream, a mix of mature

  David Shehadi Josiah Allen Real Estate, Inc.

  00 Ross Rd, Winhall, VT 05340
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  /17

  $2,495,000

  • Land
  • 2.36 Acres
  • $1,057,203 per Acre

  4 Gold Medal Cir, Stratton, VT 05343

  This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont.

  Andrew King Stratton Real Estate

  4 Gold Medal Cir, Stratton, VT 05343
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  /47

  $235,000

  • Land
  • 1.3 Acres
  • $180,769 per Acre

  80 the Hollow Rd, Winhall, VT 05340

  We can build it for you. Nestled in the heart of the picturesque **High Meadow at Stratton**, this captivating lot awaits your vision. Embrace the opportunity to own one of the last available parcels in this highly sought-after neighborhood, where extraordinary living blends seamlessly with the tranquility of the Vermont mountains. Enjoy breathtaking views of the iconic **Stratton ski

  Jacek Mikolajczyk BHHS Verani Upper Valley

  80 the Hollow Rd, Winhall, VT 05340
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  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  Margretta Fischer Wohler Realty Group

  935 Old Manchester Rd, Peru, VT 05152
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  /33

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  3 Strattonwald Rd, Winhall, VT 05340

  Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you'll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Strattonwald Rd, Winhall, VT 05340
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  /13

  $165,000

  • Land
  • 1.2 Acres
  • $137,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /2

  $625,000

  • 4 Beds
  • 1.5 Baths
  • 2,764 Sq Ft

  768 Vt Route 30, Jamaica, VT 05343

  Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

  Julie Lowe Lowe's Real Estate, LLC

  768 Vt Route 30, Jamaica, VT 05343
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  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
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  /40

  $1,695,000

  • 7 Beds
  • 7.5 Baths
  • 8,364 Sq Ft

  251 Pratt Bridge Rd, Jamaica, VT 05343

  Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

  TG Glazer Winhall Real Estate

  251 Pratt Bridge Rd, Jamaica, VT 05343
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  /30

  $735,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

  This gorgeous Stratton area townhome is designed for comfort and style, featuring three spacious bedrooms, three baths plus an open loft. Being a Highgate model, it offers a second family room with ample space for relaxation and entertainment, making it perfect for holiday gatherings. The interior of this special home has been freshly painted in October '25 and stunning wide-board pine floors

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
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  /12

  $325,000

  • Land
  • 3.42 Acres
  • $95,029 per Acre

  2366 Middletown Rd, Landgrove, VT 05148

  This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  2366 Middletown Rd, Landgrove, VT 05148
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  /38

  $1,600,000

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /28

  $1,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,363 Sq Ft

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155

  Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

  Edwin Kevil Stratton Real Estate

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155
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  /45

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  9 Lower Taylor Hill Rd, Winhall, VT 05340

  Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

  Timothy Mich Doddridge Stratton Real Estate

  9 Lower Taylor Hill Rd, Winhall, VT 05340
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  /40

  $1,025,000

  • 4 Beds
  • 2.5 Baths
  • 3,086 Sq Ft

  19 Roundtree Rd, Bondville, VT 05340

  This rare offering, located in the North Brookwood neighborhood at the Stratton Mountain Resort, presents an opportunity to secure your legacy winter home and enjoy the revenue of a $38,000 seasonal tenant and also benefit from a tax adjustment at closing. Don't overlook the benefits this property offers. Located on Stratton Mountain Resort with shuttle and near the ski trails, this four-bedroom,

  Kim Morgan-Wohler Wohler Realty Group

  19 Roundtree Rd, Bondville, VT 05340
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  /12

  $995,000

  • 3 Beds
  • 3 Baths
  • 1,501 Sq Ft

  759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

  Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

  John Sikes Stratton Real Estate

  759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
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  /30

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  340 Melendy Hill Rd, Londonderry, VT 05155

  340 Melendy Hill Road, South Londonderry, VT40 Acres | 3 Beds | 2 Baths | Expansive Barn | Mountain ViewsTucked away in the hills of South Londonderry, this charming three-bedroom, two-bath cabin offers the perfect balance of privacy, natural beauty, and quintessential Vermont living. Sited on 40 peaceful acres with sweeping mountain views, the property feels like a private

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  340 Melendy Hill Rd, Londonderry, VT 05155
• 

  

  /59

  $1,000,000

  • 3 Beds
  • 2 Baths
  • 2,700 Sq Ft

  580 Cross Rd, South Londonderry, VT 05155

  Tucked away in a tranquil setting, this newly constructed 3-bedroom, 2-bath barn-style residence is a masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody

  Loana Sargent Wohler Realty Group

  580 Cross Rd, South Londonderry, VT 05155
• 

  

  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343

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