Bennington, VT Homes

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  /38

  $1,499,999

  • 3 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  111 Hughes Ln, Jamaica, VT 05343

  Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning singlefamily home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and

  Derek Greene Derek Greene

  111 Hughes Ln, Jamaica, VT 05343
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  /46

  $5,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Nearing Rd, Winhall, VT 05340

  Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

  David Powers 42 North LP

  15 Nearing Rd, Winhall, VT 05340
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  /15

  $370,000 Sold Aug 04, 2025

  • 580 Sq Ft
  • $638/SF
  • 120 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1999

  761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

  This is your opportunity to own an iconic condominium located in the heart of the Stratton Mountain Village. Everything has been completely updated to today's style. Enjoy easy ownership through the Long Trail House association that includes a cozy gas fireplace, air conditioning for summer use, year round outdoor heated pool, three hot tubs, sauna, underground heated parking and owner storage.

  Timothy Mich Doddridge Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
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  /27

  Est $206,401 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft

  765 Thompsonburg Rd, South Londonderry, VT 05155

  765 Thompsonburg Rd, South Londonderry, VT 05155
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  /60

  $1,825,000

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

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
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  /19

  $3,000 per month

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Condo for Rent

  47 Crown Point Dr Unit B-13, Stratton, VT 05155

  Need a place to get away this Summer or Fall? Look no further. This well-equipped condo has three bedrooms and three full baths. The main living area is the much-desired open concept style which is wonderful for entertaining. There is a second living room on the lower level which is fantastic for company. This condo has several mini splits which will conquer those humid nights that we get

  Peggy O'neill Cummings & Co

  47 Crown Point Dr Unit B-13, Stratton, VT 05155
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  /27

  $1,300,000 Sold Jul 31, 2025

  • Land
  • 591 Acres
  • $2,200 per Acre

  • 136 Days On Market

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

  Welcome to an exceptional opportunity in Jamaica, VT! College Hill, a 591-acre parcel, owned by the same family for 70 years, is a rare find in today's market. Unencumbered by permits or land use restrictions, this property offers limitless possibilities. The current owners have maintained its natural beauty, never logging the land, preserving its pristine condition. At the top of College Hill,

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
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  /4

  Est $335,082 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  283 Main St, South Londonderry, VT 05155

  283 Main St, South Londonderry, VT 05155
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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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  /17

  $27,500 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Condo for Rent

  5 Byington Ln, Winhall, VT 05340

  A classic Austrian chalet, this outdoors enthusiasts' home is structured for year-round fun! The living and entertaining space encompasses the main floor: The functional open kitchen/dining room is perfect for the gang before and after weekend adventures, with a spacious great room and stone fireplace. A cozy, irresistible loft awaits upstairs for moments curled up with a book, coffee and a thick

  Jamie Luke TPW Real Estate

  5 Byington Ln, Winhall, VT 05340
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  /39

  $380,000 Sold Jul 29, 2025

  • 1,150 Sq Ft
  • $330/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  75 E Birch Rd Unit 39, Stratton, VT 05360

  Welcome to Vantage Point ! This updated and well appointed end unit is conveniently located on the second level of the middle building right behind the Stratton Fitness Center overlooking the outdoor tennis and pickleball courts. More recent upgrades are new flooring throughout, newer washer/dryer and lighting. Guest bedroom is set up for families. Winter shuttle service to the mtn base

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  75 E Birch Rd Unit 39, Stratton, VT 05360
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  /38

  Est $522,412 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  116 Deerwood Hill, South Londonderry, VT 05155

  116 Deerwood Hill, South Londonderry, VT 05155
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  /38

  $980,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  /29

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  90 Turkey Run Rd, Winhall, VT 05340

  Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

  Christiane Carroccio TPW Real Estate

  90 Turkey Run Rd, Winhall, VT 05340
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  /41

  $1,150,000 Sold Jul 25, 2025

  • 2,593 Sq Ft
  • $444/SF
  • 369 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1997

  35 Old Ridge Rd, Winhall, VT 05155

  Located in Stratton High Meadow, this four-bedroom six-bathroom home has everything you need and has a winter shuttle up to Stratton base area for skiing and snowboarding. Walking into the home, there is a large mudroom with bench and plenty of room to get gear organized and ready for the day on the mountain. The two-bay garage is off the right. Continuing, the living and dining areas have

  Mike England Michael England Real Estate

  35 Old Ridge Rd, Winhall, VT 05155
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  /21

  Est $514,500 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,754 Sq Ft

  3378 Under the Mountain Rd, South Londonderry, VT 05155

  3378 Under the Mountain Rd, South Londonderry, VT 05155
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  /57

  $629,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  11 Pond View Rd, Winhall, VT 05340

  The Intervale community has long been popular for affordability and value. This bright and sunny unit boasts an updated kitchen, primary suite on the main level with updated bath. Mini suite on upper level along with a third bedroom and shared bath with the loft area. Heating system replaced with an efficient Buderus boiler. Plenty of room for your weekend guests but a manageable floor plan for

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  11 Pond View Rd, Winhall, VT 05340
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  /28

  $770,000 Sold Jul 18, 2025

  • 3,556 Sq Ft
  • $217/SF
  • 113 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  5 Stratton Ridge Rd, Winhall, VT 05340

  Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

  Carrie Mathews Winhall Real Estate

  5 Stratton Ridge Rd, Winhall, VT 05340
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  /3

  Est $137,901 Not Listed For Sale

  • 3 Beds

  28 Melendy Hill Rd, South Londonderry, VT 05155

  28 Melendy Hill Rd, South Londonderry, VT 05155
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  /31

  $949,000

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  73 Cranberry Hill Rd, Winhall, VT 05340

  Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

  Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, Winhall, VT 05340
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  /22

  $265,500 Sold Jul 15, 2025

  • 1,332 Sq Ft
  • $199/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  18 Stratton Ridge Rd, Winhall, VT 05340

  Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

  Derek Greene Derek Greene

  18 Stratton Ridge Rd, Winhall, VT 05340
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  /18

  Est $631,212 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  155 Pratt Bridge Rd, Jamaica, VT 05343

  155 Pratt Bridge Rd, Jamaica, VT 05343
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  /16

  $635,000

  • 2 Beds
  • 2 Baths
  • 916 Sq Ft

  761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

  Beautifully renovated two bedroom two bathroom condominium in the ever popular Long Trail House community at Stratton Mountain Resort. Recently updates include new flooring throughout, paint, granite counter tops in kitchen and bathrooms, stainless steel appliances, window treatments, furniture and decor. Not many details have been left out. This particular floorplan boasts a large primary

  Timothy Mich Doddridge Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
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  /25

  $345,000 Sold Jun 30, 2025

  • 1,150 Sq Ft
  • $300/SF
  • 82 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  75 E Birch Rd Unit 21, Stratton, VT 05360

  Discover the perfect mountain getaway with this 2-bedroom, 2-bath condo located just moments from all the action at Stratton Mountain. Whether you're hitting the slopes or enjoying the year-round amenities, this condo offers convenience and comfort at every turn.Step inside to a bright and inviting space with a cozy wood-burning fireplace, ideal for relaxing after a day on the trails. The

  Carrie Mathews Winhall Real Estate

  75 E Birch Rd Unit 21, Stratton, VT 05360
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  /40

  Est $912,978 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,077 Sq Ft

  1223 Cole Pond Rd, Jamaica, VT 05343

  1223 Cole Pond Rd, Jamaica, VT 05343
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  /45

  $619,000

  • 3 Beds
  • 3 Baths
  • 2,341 Sq Ft

  49 High Point Dr Unit A122, Stratton, VT 05360

  Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living

  Mike England Michael England Real Estate

  49 High Point Dr Unit A122, Stratton, VT 05360
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  /22

  $360,000 Sold Jun 20, 2025

  • 1,430 Sq Ft
  • $252/SF
  • 112 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1960

  9 Mountain Acres Rd, Jamaica, VT 05343

  This charming ranch-style home, lovingly maintained for years, is ready for its next chapter. Ideally located at the entrance of the sought-after Mountain Acres neighborhood, it offers easy access to local activities while maintaining a peaceful retreat-like feel.Inside, five comfortable bedrooms and two baths provide ample space for family and guests. The open-concept living area, highlighted by

  Helen Nault

  9 Mountain Acres Rd, Jamaica, VT 05343
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  /30

  Est $423,054 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  1973 Pikes Falls Rd, Jamaica, VT 05343

  1973 Pikes Falls Rd, Jamaica, VT 05343
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  /21

  $609,000

  • 2 Beds
  • 2 Baths
  • 916 Sq Ft

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

  771 Stratton Mountain Access Rd, Stratton, VT 05155Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common.

  Andrew King Stratton Real Estate

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
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  /54

  $970,000 Sold Jun 17, 2025

  • 2,672 Sq Ft
  • $363/SF
  • 120 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  13 Windtree Rd, Bondville, VT 05340

  OPEN HOUSE SATURDAY , February 22nd-11:00-3:00.Showings begin 2/20Exceptional Stratton Mountain Resort location on Windtree Road in the desirable North Brookwood neighborhood with Shuttle from your driveway to the Base Lodge! Enjoy this wonderful deck house open floor plan with great winter views, vaulted ceilings, 2 wood burning fireplaces and multiple decks. Well designed for apres ski

  Kim Morgan-Wohler Wohler Realty Group

  13 Windtree Rd, Bondville, VT 05340
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  /40

  Est $571,575 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, Jamaica, VT 05343
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  /50

  $1,050,000

  • 5 Beds
  • 5.5 Baths
  • 4,729 Sq Ft

  83 Benson Fuller Dr, Bondville, VT 05340

  Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

  Christiane Carroccio TPW Real Estate

  83 Benson Fuller Dr, Bondville, VT 05340
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  /29

  $363,825 Sold Jun 06, 2025

  • 1,215 Sq Ft
  • $299/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340

  Discover the ease of Mountain living with the complimentary Birch Hill Shuttle, providing seamless access to winter adventures. This bright and welcoming end-unit townhouse offers plenty of space for family and friends to gather and unwind. With two inviting living areas, three comfortable bedrooms, and two well-appointed bathrooms, there's room for everyone to relax. The spacious entryway is

  Christine Chovan

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340
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  /40

  Est $505,484 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,364 Sq Ft

  482 Pratt Bridge Rd, Jamaica, VT 05343

  482 Pratt Bridge Rd, Jamaica, VT 05343
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  /59

  $1,200,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,054 Sq Ft

  4 Garden Loop Rd, Winhall, VT 05340

  Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

  Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
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  /30

  $510,000 Sold Jun 05, 2025

  • 1,459 Sq Ft
  • $350/SF
  • 170 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  5600 Pikes Falls Rd, Jamaica, VT 05343

  Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or

  Jamie Wylie Stratton Real Estate

  5600 Pikes Falls Rd, Jamaica, VT 05343
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  /31

  Est $605,517 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,593 Sq Ft

  81 Edie Ln, Jamaica, VT 05343

  81 Edie Ln, Jamaica, VT 05343
• 

  

  /41

  $865,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  2 Stratton Springs Rd Unit 2, Stratton, VT 05360

  Welcome to the exceptional Resort Townhome community of Stratton Springs with private shuttle, Stratton Sports Center access and convenient location near the Stratton Mountain Resort Village and lifts. These upscale floor plans offer a multi level great room with 2 story ceilings, walls of windows with natural light and commanding fireplace. The second level gourmet kitchen and dining area

  Kim Morgan-Wohler Wohler Realty Group

  2 Stratton Springs Rd Unit 2, Stratton, VT 05360
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  /34

  $690,000 Sold May 30, 2025

  • 1,502 Sq Ft
  • $459/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1977

  22 Shattarack Rd Unit A-5, Stratton, VT 05360

  Slopeside A-5 at Stratton Mountain is a 3-level townhouse with direct access to the Tamarack ski lift via a short walk down a maintained trail. This offering features a generous ski room entry with powder room, main level living and dining with wood-burning fireplace and private deck, upper level primary suite, and lower level bunk room, guest bedroom with Queen bed, shared full bathroom, and

  Beth Vickers Vermont Real Estate Company

  22 Shattarack Rd Unit A-5, Stratton, VT 05360
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  /25

  Est $770,949 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

Showing Results 41 - 80, Page 2 of 18