Windham, VT Homes

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  /44

  $400,000

  • 2 Beds
  • 3 Baths
  • 1,696 Sq Ft

  399 Laurel Lake Rd, Jacksonville, VT 05342

  Turnkey 2-Bedroom Home with Lake Access & Extra Garage – Laurel Lake Living! Welcome to this meticulously maintained 2-bedroom, 3-bathroom home, offering turnkey convenience and year-round comfort just steps from beautiful Laurel Lake. Boasting an open and inviting floor plan, this home features a spacious living area with a cozy pellet stove for energy-efficient warmth, perfect for chilly

  Claire Renaud Berkley & Veller Greenwood Country

  399 Laurel Lake Rd, Jacksonville, VT 05342
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  /40

  $280,000 Sold Jun 20, 2025

  • 1,680 Sq Ft
  • $167/SF
  • 268 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  427 Vermont 112, Whitingham, VT 05342

  Discover this turnkey 3-bedroom Cape-style home, charmingly nestled on the edge of the village of Jacksonville. A babbling brook borders the property, flowing gracefully under a quaint bridge. Recently transformed by the current owners, this lovely residence features a new drilled well, new efficient propane furnace, an electric hot water heater, ensuring all major systems are up to date. Enjoy

  Monica Sumner BHG Masiello Brattleboro

  427 Vermont 112, Whitingham, VT 05342
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  /29

  Est $509,922 Not Listed For Sale

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

  960 Holbrook Rd, Jacksonville, VT 05342

  960 Holbrook Rd, Jacksonville, VT 05342
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  /55

  $349,000

  • 3 Beds
  • 2 Baths
  • 2,910 Sq Ft

  597 Gates Pond Rd, Jacksonville, VT 05342

  Classic Greek Revival Expanded in True New England Farmhouse Fashion w/Studios, Timber-Frame Barn, Workshop, & Greenhouse on 3+ surveyed Acres. This 3-bed, 2-bath offers approximately 3,000 square feet of finished living space w/ flowing layout connecting a series of versatile spaces—all under one roof. From the original formal rooms of the farmhouse, step into a sequence of functional bonus

  Jacki Murano Southern Vermont Realty Group

  597 Gates Pond Rd, Jacksonville, VT 05342
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  /54

  $665,000 Sold May 29, 2025

  • 4,881 Sq Ft
  • $136/SF
  • 40 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1840

  201 Vermont 112, Whitingham, VT 05342

  Experience endless enjoyment in this charming 4-bedroom converted winery, where every room promises relaxation & excitement. Nestled amidst serene surroundings, discover hiking trails in the backyard, a picturesque pond inhabited by a beaver, a gazebo and a flowing river with a quaint wooden bridge leading to an expansive parking lot accommodating up to 10 cars.  Indoors, an inviting barn houses

  Steve Goldfarb Deerfield Valley Real Estate

  201 Vermont 112, Whitingham, VT 05342
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  /39

  Est $585,320 Not Listed For Sale

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

  3358 Vt Route 100, Whitingham, VT 05361

  3358 Vt Route 100, Whitingham, VT 05361
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  /50

  $339,000

  • 7 Beds
  • 4 Baths
  • 3,000 Sq Ft

  89 Gates Pond Rd, Whitingham, VT 05342

  This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

  Monique White Deerfield Valley Real Estate

  89 Gates Pond Rd, Whitingham, VT 05342
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  /15

  $150,000 Sold Jan 27, 2025

  • 1,152 Sq Ft
  • $130/SF
  • 140 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 2000

  199 Fowler Rd, Jacksonville, VT 05342

  Private home on a 3 acre parcel nestled in the hills of Halifax off a quiet dirt road. The parcel is slightly sloping with enormous potential for clearing and opening up the light. The home is in disrepair and needs an overhaul, but priced accordingly for the right buyer to get an amazing value. Currently set up as 2 stories with a finished main floor with kitchen, bedroom, and bath, and a

  Adam Palmiter Berkley & Veller Greenwood/Dover

  199 Fowler Rd, Jacksonville, VT 05342
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  /35

  Est $304,141 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,860 Sq Ft

  159 Reed Hill Rd, Jacksonville, VT 05342

  159 Reed Hill Rd, Jacksonville, VT 05342
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  /57

  $240,000 Sold Dec 05, 2024

  • 1,700 Sq Ft
  • $141/SF
  • 18 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1860

  292 Parsons Rd, Jacksonville, VT 05342

  Discover the charm of this 1860 farmhouse set on 17 stunning acres in Jacksonville, VT. Perfect for horses, farming, or creating your family compound, this property offers endless possibilities. Just minutes from Mount Snow, with boating, hiking, fly fishing, and more nearby, it’s an outdoor enthusiast’s dream. The south-facing land includes rolling pastures and a year-round brook, ideal for

  Donald Koelsch Deerfield Valley Real Estate

  292 Parsons Rd, Jacksonville, VT 05342
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  /40

  Est $490,326 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  371 Butler Brook Rd, Jacksonville, VT 05342

  371 Butler Brook Rd, Jacksonville, VT 05342
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  /29

  $590,000 Sold Oct 28, 2024

  • 2,732 Sq Ft
  • $216/SF
  • 35 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1840

  55 Reed Hill Rd, Jacksonville, VT 05342

  Originally a centerpiece of a thriving farm in 1840, this farmhouse now stands amidst lush forests on what was once grazing land. Nestled alongside a 20-acre pond, it boasts a dam that historically powered downstream mills. Extensively renovated, the home offers five bedrooms and three full baths. The barn, reconstructed on its original foundation, includes a two-car garage with a spacious studio

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  55 Reed Hill Rd, Jacksonville, VT 05342
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  /17

  Est $140,864 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  813 Gates Pond Rd, Jacksonville, VT 05342

  813 Gates Pond Rd, Jacksonville, VT 05342
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  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  427 Vt Rte 112, Whitingham, VT 05361

  427 Vt Rte 112, Whitingham, VT 05361
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  /38

  Est $913,583 Not Listed For Sale

  • 12 Beds
  • 5 Baths
  • 7,400 Sq Ft

  267 Academy Rd, Jacksonville, VT 05342

  267 Academy Rd, Jacksonville, VT 05342
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  /16

  Est $359,227 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  477 Bernard Rd, Jacksonville, VT 05342

  477 Bernard Rd, Jacksonville, VT 05342
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  /36

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  63 Vermont 112, Whitingham, VT 05342

  63 Vermont 112, Whitingham, VT 05342
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  /34

  Est $595,927 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  453 Vt Route 112, Jacksonville, VT 05342

  453 Vt Route 112, Jacksonville, VT 05342
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  /38

  Est $392,599 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,350 Sq Ft

  290 Vt Route 112, Jacksonville, VT 05342

  290 Vt Route 112, Jacksonville, VT 05342
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  /34

  Est $567,376 Not Listed For Sale

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

  2579 Collins Rd, Jacksonville, VT 05342

  2579 Collins Rd, Jacksonville, VT 05342
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  /29

  Est $327,998 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  1275 Parsons Rd, Jacksonville, VT 05342

  1275 Parsons Rd, Jacksonville, VT 05342
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  /26

  Est $227,247 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,800 Sq Ft

  64 Gates Pond Rd, Whitingham, VT 05342

  64 Gates Pond Rd, Whitingham, VT 05342
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  /37

  Est $712,410 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,488 Sq Ft

  678 Stonehouse Rd, Jacksonville, VT 05342

  678 Stonehouse Rd, Jacksonville, VT 05342
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  /31

  Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,147 Sq Ft

  3012 Vt Route 100, Whitingham, VT 05361

  3012 Vt Route 100, Whitingham, VT 05361
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  /26

  Est $310,895 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  101 Fowler Rd, Jacksonville, VT 05342

  101 Fowler Rd, Jacksonville, VT 05342
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  /19

  Est $199,504 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 437 Sq Ft

  639 Stonehouse Rd, Jacksonville, VT 05342

  639 Stonehouse Rd, Jacksonville, VT 05342
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  /29

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,990 Sq Ft

  171 Vermont 112, Whitingham, VT 05342

  171 Vermont 112, Whitingham, VT 05342
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  /23

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  236 Vermont 112, Whitingham, VT 05342

  236 Vermont 112, Whitingham, VT 05342
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  /6

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,634 Sq Ft

  568 Vermont 112, Whitingham, VT 05342

  568 Vermont 112, Whitingham, VT 05342
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  /37

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  2915 Vt Rte 100, Whitingham, VT 05361

  2915 Vt Rte 100, Whitingham, VT 05361
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  /26

  Est $531,413 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  101 Elwin Ln, Jacksonville, VT 05342

  101 Elwin Ln, Jacksonville, VT 05342
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  /13

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  29 Gates Pond, Whitingham, VT 05361

  29 Gates Pond, Whitingham, VT 05361
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  /27

  Est $463,737 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,646 Sq Ft

  1320 Vt Route 8a, Jacksonville, VT 05342

  1320 Vt Route 8a, Jacksonville, VT 05342
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  /17

  Est $281,024 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  84 Allen Rd, Jacksonville, VT 05342

  84 Allen Rd, Jacksonville, VT 05342
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  /31

  Est $260,981 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,284 Sq Ft

  54 Holbrook Rd, Jacksonville, VT 05342

  54 Holbrook Rd, Jacksonville, VT 05342
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  /24

  Est $357,637 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  89 Academy Rd, Jacksonville, VT 05342

  89 Academy Rd, Jacksonville, VT 05342
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  /21

  Est $311,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  30 Holland Ln, Jacksonville, VT 05342

  30 Holland Ln, Jacksonville, VT 05342
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  /23

  Est $476,836 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  2686 Collins Rd, Jacksonville, VT 05342

  2686 Collins Rd, Jacksonville, VT 05342
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  /19

  Est $377,068 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,644 Sq Ft

  22 Lake Hill Rd, Jacksonville, VT 05342

  22 Lake Hill Rd, Jacksonville, VT 05342
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  /24

  Est $356,196 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft

  922 Gates Pond Rd, Jacksonville, VT 05342

  922 Gates Pond Rd, Jacksonville, VT 05342

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