South Londonderry, VT Homes

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  /44

  $729,000

  • 4 Beds
  • 2 Baths
  • 2,040 Sq Ft

  86 Benson Fuller Dr, Bondville, VT 05340

  Great opportunity! Your Ultimate Getaway Escape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces.Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf matches below. In the cooler

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  86 Benson Fuller Dr, Bondville, VT 05340
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  /60

  $2,100,000 Sold May 02, 2025

  • 6,195 Sq Ft
  • $339/SF
  • 246 Days On Market

  • 7 Beds
  • 5.5 Baths
  • Built 2007

  18 Rocky Dell Rd, Winhall, VT 05340

  Welcome to this stunning Contemporary Mountain Estate on 26 acres where luxury, privacy and nature converge.Offering more than a home-It's a lifestyle with the perfect blend of sophistication, comfort & natural surroundings. Ideally located just minutes to the Stratton Mountain Resort or the Green Mountain National Forest, easily accessed from Kendall Farm Road. Enjoy the mountains & the outdoors

  Kim Morgan-Wohler Wohler Realty Group

  18 Rocky Dell Rd, Winhall, VT 05340
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  /30

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,785 Sq Ft

  13 Stratton Rd W Unit 13, Winhall, VT 05340

  13 Stratton Rd W Unit 13, Winhall, VT 05340
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  /37

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  115 Benson Fuller Dr, Jamaica, VT 05343

  Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

  Carrie Mathews Winhall Real Estate

  115 Benson Fuller Dr, Jamaica, VT 05343
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  /53

  $825,000 Sold Apr 29, 2025

  • Land
  • 36 Acres
  • $23,109 per Acre

  • 102 Days On Market

  324 Pikes Falls Rd, South Londonderry, VT 05155

  Extraordinary Stratton Mountain Acreage Opportunity:Discover a rare gem in Stratton Mountain, a 35.7-acre parcel offering breathtaking, commanding views of the resort. Just 5 minutes away from the the Main Base Lodge and less to Sun Bowl. This exceptional property features two building sites, each supported by wastewater systems for a 6-bedroom and a 4-bedroom home.The established driveway leads

  Britt Wohler Wohler Realty Group

  324 Pikes Falls Rd, South Londonderry, VT 05155
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  /40

  Est $615,417 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  10 Deer St, Bondville, VT 05340

  10 Deer St, Bondville, VT 05340
• 

  

  /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
• 

  

  /37

  $454,000 Sold Apr 28, 2025

  • 1,760 Sq Ft
  • $258/SF
  • 315 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  400 Edie Ln, Jamaica, VT 05343

  Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  400 Edie Ln, Jamaica, VT 05343
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,016 Sq Ft

  12 Quarter Mile Rd, Winhall, VT 05360

  12 Quarter Mile Rd, Winhall, VT 05360
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  /55

  $2,225,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  16 Hunter Ridge Rd, Bondville, VT 05340

  Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  16 Hunter Ridge Rd, Bondville, VT 05340
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  /44

  $640,000 Sold Apr 25, 2025

  • 3,988 Sq Ft
  • $160/SF
  • 52 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 1942

  13 Winhall Station Rd, Londonderry, VT 05155

  Solid six-bedroom home with detached one bedroom apartment being offered fully furnished on 3.4 acres of land! Surrounded by mature maples and beautiful local views of Stratton Mountain. This property sits on the corner of Winhall Station Road and Route 100 in Londonderry Vermont. Winhall Station Road will lead out a dead-end road to the Winhall Campground and the West River area with wonderful

  Julie Lowe Lowe's Real Estate, LLC

  13 Winhall Station Rd, Londonderry, VT 05155
• 

  

  /40

  Est $912,784 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,872 Sq Ft

  34 Raspberry Hill Rd, Winhall, VT 05340

  34 Raspberry Hill Rd, Winhall, VT 05340
• 

  

  /35

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  5 Linscott Rd Unit 56, Jamaica, VT 05343

  This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances,

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  5 Linscott Rd Unit 56, Jamaica, VT 05343
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  /6

  $122,500 Sold Apr 18, 2025

  • Land
  • 2.20 Acres
  • $55,682 per Acre

  • 53 Days On Market

  10 Little Brook Rd, Winhall, VT 05340

  Prime 2.2-acre building lot in the desirable Vermont Ventures community! Conveniently located less than 15 minutes from Stratton Resort and Bromley, just 20 minutes from Manchester. This property includes a wastewater permit for a 5-bedroom home, with power available at the road, Little Brook is a town-maintained road, there is a ROW for access to the lot. With some clearing, the property offers

  Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  10 Little Brook Rd, Winhall, VT 05340
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  /26

  Est $255,076 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 595 Sq Ft

  28 Stratton Rd W Unit 28, Winhall, VT 05340

  28 Stratton Rd W Unit 28, Winhall, VT 05340
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  /41

  $574,000

  • 3 Beds
  • 3 Baths
  • 2,704 Sq Ft

  4138 W Hill Rd S, Jamaica, VT 05343

  This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

  Patricia Fitzpatrick Skihome Realty

  4138 W Hill Rd S, Jamaica, VT 05343
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  /37

  $615,000 Sold Apr 15, 2025

  • 1,500 Sq Ft
  • $410/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  29 Burnt Hill Rd, Winhall, VT 05340

  Discover your dream chalet in the heart of Strattonwald—a stunningly renovated retreat designed for year-round mountain adventures and modern comfort! Beautifully renovated 3-bedroom, 2-bathroom home in Winhall offers the perfect blend of convenience and recreation. Just a quick drive to Stratton Mountain, this property provides easy access to winter slopes and summer fun. The community amenities

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  29 Burnt Hill Rd, Winhall, VT 05340
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  /35

  Est $498,006 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  383 Winhall Hollow Rd, Bondville, VT 05340

  383 Winhall Hollow Rd, Bondville, VT 05340
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  /33

  $820,000

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

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

  Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

  Carrie Mathews Winhall Real Estate

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
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  /40

  $850,000 Sold Apr 04, 2025

  • 3,119 Sq Ft
  • $273/SF
  • 168 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  36 Road To Millbrook, Winhall, VT 05340

  This impeccably maintained home sits on 5.28 acres of beautifully landscaped land adjacent to the National Forest. Featuring a spacious interior with a stone wood-burning fireplace and vaulted cathedral ceilings, this home is move-in ready. Recent upgrades include two newly renovated bathrooms. The first floor offers an open living layout, while the lower level boasts a cozy den/family room.

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  36 Road To Millbrook, Winhall, VT 05340
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  /40

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,212 Sq Ft

  74 N Brookwood, Stratton, VT 05155

  74 N Brookwood, Stratton, VT 05155
• 

  

  /31

  $799,000

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

  9 F Cobble Ridge Rd, Winhall, VT 05340

  Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

  Carrie Mathews Winhall Real Estate

  9 F Cobble Ridge Rd, Winhall, VT 05340
• 

  

  /41

  $2,100,000 Sold Apr 04, 2025

  • 5,300 Sq Ft
  • $396/SF
  • 248 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1974

  20 W Ridge Rd, Stratton, VT 05360

  OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome.The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and

  Christiane Carroccio TPW Real Estate

  20 W Ridge Rd, Stratton, VT 05360
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  /38

  Est $1,514,064 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,997 Sq Ft

  308 Hubble Rd, Peru, VT 05152

  308 Hubble Rd, Peru, VT 05152
• 

  

  /28

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,055 Sq Ft

  21 Burnt Hill Rd, Winhall, VT 05341

  Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont!This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  21 Burnt Hill Rd, Winhall, VT 05341
• 

  

  /39

  $1,250,000 Sold Apr 02, 2025

  • 2,625 Sq Ft
  • $476/SF
  • 32 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2003

  6 Cranberry Ct, Stratton, VT 05360

  Designed for mountain living, this expansive 4-bedroom, 4-bathroom townhome is the largest floor plan in Tree Top, offering unparalleledsquare footage and luxurious features. The property includes a total of 4 bedrooms, 3 are spacious primary suites with private baths, a cozy lower-level family room, and an open-concept great room adorned with a stone fireplace, soaring cathedral ceilings, and

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  6 Cranberry Ct, Stratton, VT 05360
• 

  

  /36

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,244 Sq Ft

  22 Upper Glades Unit 22, Stratton, VT 05360

  22 Upper Glades Unit 22, Stratton, VT 05360
• 

  

  /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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  /35

  $1,900,000 Sold Apr 01, 2025

  • 2,581 Sq Ft
  • $736/SF
  • 14 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  16 Mountain Reach Mews Rd, Stratton, VT 05155

  Located just steps from Stratton Village and the lifts, this luxurious slopeside townhouse offers a seamless blend of upscale contemporary design and unbeatable convenience. With gated access and no public roads to cross, this end-unit residence provides a true retreat in the heart of Stratton’s trailside community.Step into the bright, open floor plan where modern elegance meets extraordinary

  Trent Stephens Wohler Realty Group

  16 Mountain Reach Mews Rd, Stratton, VT 05155
• 

  

  /39

  Est $1,294,947 Not Listed For Sale

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

  19 Maple Hill Rd, Winhall, VT 05340

  19 Maple Hill Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /19

  $585,000 Sold Apr 01, 2025

  • 1,811 Sq Ft
  • $323/SF
  • 180 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  47 High Point Dr Unit B21, Stratton, VT 05360

  This top-floor, end-unit 3-bedroom, 3-bath Crown Point condominium offers the ideal balance of comfort and convenience. Located just a short walk from the Stratton Sports Center and Stratton Village, it's perfectly situated for both relaxation and adventure. The shuttle provides easy access to the slopes and all that Stratton has to offer. Inside, the open floor plan features cathedral ceilings

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  47 High Point Dr Unit B21, Stratton, VT 05360
• 

  

  /26

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,993 Sq Ft

  47 Styles Branch Rd Unit 907, Stratton, VT 05360

  47 Styles Branch Rd Unit 907, Stratton, VT 05360
• 

  

  /60

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

  Steve Goldfarb Deerfield Valley Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /14

  $1,050,000 Sold Mar 29, 2025

  • 1,780 Sq Ft
  • $590/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

  Incredible opportunity to own in one of Stratton Mountain Resort's most desirable communities! One of the largest three bedroom floor plans in all of Hearthstone Lodge. This home boasts three bedroom and two and half bathrooms, corner location directly off the elevator, open floor plan with mountain views, cozy gas fireplace, air conditioning for Summer use and two assigned underground parking

  Timothy Mich Doddridge Stratton Real Estate

  759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340
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  /26

  Est $515,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,763 Sq Ft

  121 Stratton Gate Rd, Jamaica, VT 05343

  121 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /13

  $165,000

  • Land
  • 1.20 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
• 

  

  /29

  $455,000 Sold Mar 28, 2025

  • 1,570 Sq Ft
  • $290/SF
  • 53 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  2 Byington Ln Unit 5, Winhall, VT 05340

  Welcome to this stunning, modern townhome overlooking the pool, just a short walk to Winhall shops and restaurants and only minutes from the renowned Stratton Resort. This three-bedroom, two-bathroom townhome offers the perfect Vermont retreat for all seasons, with a layout designed to maximize mountain views and convenience.Spread across three levels, the home’s second floor boasts an

  Robin Apps Four Seasons Sotheby's Int'l Realty

  2 Byington Ln Unit 5, Winhall, VT 05340
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  /40

  Est $922,245 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,196 Sq Ft

  40 Loop Rd, Winhall, VT 05340

  40 Loop Rd, Winhall, VT 05340
• 

  

  /6

  $239,000

  • Land
  • 1.57 Acres
  • $152,229 per Acre

  2 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

  2 Gold Medal Cir, Stratton, VT 05343

Showing Results 121 - 160, Page 4 of 18