West Windsor, VT Homes

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  $500,000

  • 3 Beds
  • 3 Baths
  • 1,826 Sq Ft

  789 Hammond Hill Rd, West Windsor, VT 05089

  "The Hideaway House - A Private Sanctuary”: This light-filled contemporary retreat located high on a hill in fashionable West Windsor is the quintessential "Goldilocks" Vermont property. It offers a private woodland sanctuary where quiet tranquility and architectural highlights meet. Tucked into a secluded 5.52-acre wooded bowl and set back over 200 ft. from the road, this tasteful 3BR/3BA home

  

  Ross Doody

  Century 21 Highview Realty

  (802) 523-2984

  789 Hammond Hill Rd, West Windsor, VT 05089
• Explore West Windsor

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  /2

  $4,350,000 Sold Dec 12, 2025

  700 Barton Rd, West Windsor, VT 05089

  • 3 Beds
  • 3.5 Baths
  • 3,884 Sq Ft
  • Built 2006

  Last Sold Summary

  • $1,120/SF
  • 0 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  700 Barton Rd, West Windsor, VT 05089
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  /40

  Est $1,233,238 Not Listed For Sale

  384 Skyhawk Ln, Brownsville, VT 05037

  • 4 Beds
  • 4.5 Baths
  • 4,411 Sq Ft
  • Built 2004

  384 Skyhawk Ln, Brownsville, VT 05037

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 12 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent David Donegan Snyder Donegan Real Estate Group
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  /44

  $849,900

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037
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  /41

  $525,000 Sold Dec 15, 2025

  77 Winding Rd, Brownsville, VT 05037

  • 4 Beds
  • 2 Baths
  • 2,380 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $221/SF
  • 23 Days On Market

  Current Estimated Value $526,393

  Last Listing Agent Dana Waters Dark Horse Realty

  77 Winding Rd, Brownsville, VT 05037
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  /35

  Not Listed For Sale

  951 Ski Tow Rd, West Windsor, VT 05037

  • 4 Beds
  • 4.5 Baths
  • 2,504 Sq Ft
  • Built 2003

  951 Ski Tow Rd, West Windsor, VT 05037

  Last Sold Summary

  • $240/SF
  • 6 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Karen DeMas Four Seasons Sotheby's Int'l Realty
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  /11

  $150,000

  • Land
  • 1.79 Acres
  • $83,799 per Acre

  83 Coaching Ln, West Windsor, VT 05037

  Shovel ready project in Brownsville Vt.Fully permitted and ready to go for a timber-frame plan up to 5 bedrooms. 1.79 acre vacant lot only for asking price, or built to suit option. Proven aquifer for high production well. Gorgeous views of Mt. Ascutney, minutes to the ski mountain and outdoor recreation center. The area is known for kind welcoming people and local farms. The Ascutney outdoor

  Jason Saphire www.HomeZu.com

  83 Coaching Ln, West Windsor, VT 05037
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  /24

  $60,000 Sold Dec 18, 2025

  5 Clough Ave, West Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft
  • Built 1920

  Last Sold Summary

  • 25% Below List Price
  • $43/SF
  • 13 Days On Market

  Current Estimated Value $165,000

  Last Listing Agent Derek Greene Derek Greene

  5 Clough Ave, West Windsor, VT 05089
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  /39

  Not Listed For Sale

  122 Parrish View Rd, West Windsor, VT 05037

  • 2 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Built 2007

  122 Parrish View Rd, West Windsor, VT 05037

  Last Sold Summary

  • $439/SF
  • 47 Days On Market

  Last Sold Price $614,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
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  /20

  $279,900 New Construction

  • 1,308 Sq Ft

  320 W Rowe Hill Rd, West Windsor, VT 05037

  Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

  Dana Waters Dark Horse Realty

  320 W Rowe Hill Rd, West Windsor, VT 05037
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  /33

  $315,000 Sold Sep 19, 2025

  1159 Ski Tow Rd, Brownsville, VT 05037

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Below List Price
  • $190/SF
  • 24 Days On Market

  Last Listing Agent Dana Waters Dark Horse Realty

  1159 Ski Tow Rd, Brownsville, VT 05037
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  /25

  Est $669,200 Not Listed For Sale

  124 Village Ln, West Windsor, VT 05037

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2011

  124 Village Ln, West Windsor, VT 05037

  Last Sold Summary

  • 23% Above List Price
  • $378/SF
  • 246 Days On Market

  Last Sold Price $545,000

  Last Listing Agent Seth Warren Seth Warren Real Estate
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  /32

  $299,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,594 Sq Ft

  72 Mountains Edge Rd Unit 508, Brownsville, VT 05037

  Stunning Mountain Retreat with Cathedral Ceilings & Trail Access Discover this beautiful condo at Mountains Edge—offering the best views, ultimate privacy, and unparalleled access to outdoor recreation. This residence captures sweeping views over West Windsor and the surrounding mountains. The private balcony off the living room and intimate patio off the master bedroom provide perfect vantage

  Mike Hickey KW Vermont Woodstock

  72 Mountains Edge Rd Unit 508, Brownsville, VT 05037
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  /2

  $299,000 Sold Feb 02, 2026

  22 Hammond Hill Rd, West Windsor, VT 05089

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1963

  Last Sold Summary

  • $319/SF
  • 0 Days On Market

  Current Estimated Value $299,682

  Last Listing Agent Shawna Fox BHHS Verani Upper Valley

  22 Hammond Hill Rd, West Windsor, VT 05089
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  /40

  Est $1,473,385 Not Listed For Sale

  89 Silver Hill Rd, West Windsor, VT 05089

  • 3 Beds
  • 2.5 Baths
  • 4,200 Sq Ft
  • Built 2020

  89 Silver Hill Rd, West Windsor, VT 05089

  Last Sold Summary

  • 5% Above List Price
  • $333/SF
  • 46 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty
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  /16

  $390,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  181 Banister Rd, Windsor, VT 05089

  Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

  Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, Windsor, VT 05089
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  /15

  $191,000 Sold Apr 24, 2025

  295 Hotel Rd Unit 16/16A, Brownsville, VT 05037

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Above List Price
  • $209/SF
  • 93 Days On Market

  Last Listing Agent Laurie Kirkpatrick Four Seasons Sotheby's Int'l Realty

  295 Hotel Rd Unit 16/16A, Brownsville, VT 05037
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  /47

  Est $872,395 Not Listed For Sale

  3894 Rush Meadow Rd, West Windsor, VT 05089

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1850

  3894 Rush Meadow Rd, West Windsor, VT 05089

  Last Sold Summary

  • 6% Below List Price
  • $462/SF
  • 42 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty
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  /15

  $185,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 850 Sq Ft

  295 Hotel Rd Unit 15, Brownsville, VT 05037

  Welcome home to this charming 2 bedroom, 2 bathroom condo tucked in the peaceful mountains of Vermont. Ascutney Trails Association has so much to offer, year round community activities, education and recreation. This unit is turnkey and updated throughout! Enjoy winter skiing, snowshoeing, tubing and in the warmer months enjoy the vast trails for hiking, biking, fishing and more. Two assigned

  Marie Parry M Realty

  295 Hotel Rd Unit 15, Brownsville, VT 05037
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  /41

  $515,000 Sold Nov 14, 2025

  968 Ski Tow Rd, West Windsor, VT 05037

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft
  • Built 1995

  Last Sold Summary

  • $216/SF
  • 7 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  968 Ski Tow Rd, West Windsor, VT 05037
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  /33

  Est $911,867 Not Listed For Sale

  5434 Rush Meadow Rd, West Windsor, VT 05089

  • 3 Beds
  • 2.5 Baths
  • 2,988 Sq Ft
  • Built 2003

  5434 Rush Meadow Rd, West Windsor, VT 05089

  Last Sold Summary

  • 6% Below List Price
  • $326/SF
  • 6 Days On Market

  Last Sold Price $975,000

  Last Listing Agent David Donegan Snyder Donegan Real Estate Group
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  /33

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  7 Best Rd, West Windsor, VT 05089

  Nestled on a picturesque 2.9 acres along Hartland-Brownsville Rd, this property offers the perfect blend of privacy and convenience offering sweeping views and mature trees. This unique property features a 1994 Skyline doublewide home with a newer attached 2 car garage. Step into the heart of the main home and be greeted by an abundance of natural light streaming through large windows that

  Seth Barbiero EXP Realty

  7 Best Rd, West Windsor, VT 05089
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  /11

  $200,000 Sold Apr 25, 2025

  295 Hotel Rd Unit 14A/14B, Brownsville, VT 05037

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Above List Price
  • $120/SF
  • 56 Days On Market

  Last Listing Agent Dana Waters Dark Horse Realty

  295 Hotel Rd Unit 14A/14B, Brownsville, VT 05037
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  /40

  Est $549,106 Not Listed For Sale

  3052 Brownsville Hartland Rd, West Windsor, VT 05089

  • 2 Beds
  • 2 Baths
  • 2,012 Sq Ft
  • Built 1965

  3052 Brownsville Hartland Rd, West Windsor, VT 05089

  Last Sold Summary

  • 13% Above List Price
  • $241/SF
  • 64 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
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  /19

  $110,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089

  Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One

  Ann Jacques Century 21 Highview Realty

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089
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  /22

  $295,000 Sold Nov 07, 2025

  72 Mountains Edge Rd Unit 507, Brownsville, VT 05037

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $162/SF
  • 6 Days On Market

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  72 Mountains Edge Rd Unit 507, Brownsville, VT 05037
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  /25

  Est $383,955 Not Listed For Sale

  46 Yodel Valley Rd, West Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 624 Sq Ft
  • Built 1970

  46 Yodel Valley Rd, West Windsor, VT 05089

  Last Sold Summary

  • 1% Above List Price
  • $609/SF
  • 8 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Tyler Hall BHHS Verani Upper Valley
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  /16

  $390,000 Under Contract

  • Land
  • 10.2 Acres
  • $38,235 per Acre

  181 Banister Rd, West Windsor, VT 05037

  Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

  Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, West Windsor, VT 05037
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  /36

  $535,000 Sold Sep 01, 2025

  65 Bergland Ln, West Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Above List Price
  • $333/SF
  • 6 Days On Market

  Current Estimated Value $545,269

  Last Listing Agent Holly Hall Hall Collins Real Estate Group

  65 Bergland Ln, West Windsor, VT 05089
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  /29

  Est $458,589 Not Listed For Sale

  406 Rush Meadow Rd, Brownsville, VT 05037

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1975

  406 Rush Meadow Rd, Brownsville, VT 05037

  Last Sold Summary

  • 18% Above List Price
  • $250/SF
  • 9 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Dana Waters Dark Horse Realty
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  /36

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  70 Mountains Edge Rd Unit 603, West Windsor, VT 05037

  This inviting condo offers the perfect blend of comfort, convenience, and year-round outdoor access. Step right outside your back door to enjoy scenic hiking and biking trails, while world-class skiing and snowboarding are just moments away. This unique home features two separate floors, ideal for flexible living. The first floor offers its own private entrance, along with dedicated bedrooms and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  70 Mountains Edge Rd Unit 603, West Windsor, VT 05037
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  /30

  $460,000 Sold Oct 02, 2025

  586 Ski Tow Rd, Brownsville, VT 05037

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1971

  Last Sold Summary

  • 16% Below List Price
  • $311/SF
  • 84 Days On Market

  Current Estimated Value $450,720

  Last Listing Agent Dana Waters Dark Horse Realty

  586 Ski Tow Rd, Brownsville, VT 05037
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  /18

  Not Listed For Sale

  00 Brownsville Hartland Rd, West Windsor, VT 05037

  00 Brownsville Hartland Rd, West Windsor, VT 05037

  Last Sold Summary

  • 15 Days On Market

  Last Sold Price $120,000

  Last Listing Agent John Bassette Bassette Real Estate Group
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  /25

  $207,000

  • 3 Beds
  • 1,604 Sq Ft

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

  This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the property. This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountain biking, hiking, cross-country skiing, snowshoeing, and

  Allison Griep BHHS Verani Upper Valley

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
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  /5

  $575,000 Sold May 09, 2025

  237 John Meyers Rd, West Windsor, VT 05037

  • Land
  • 107.41 Acres
  • $5,353 per Acre

  Last Sold Summary

  • 28% Below List Price
  • 661 Days On Market

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  237 John Meyers Rd, West Windsor, VT 05037
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  /13

  Not Listed For Sale

  789 Ski Tow Rd, West Windsor, VT 05037

  • 1 Bed
  • 1 Bath
  • 506 Sq Ft
  • Built 1966

  789 Ski Tow Rd, West Windsor, VT 05037

  Last Sold Summary

  • $270/SF
  • 90 Days On Market

  Last Sold Price $136,500

  Last Listing Agent Amy Messina Town and Country Realty
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  $637,500 Sold Feb 27, 2026

  1051 Banister Rd, West Windsor, VT 05089

  • 3 Beds
  • 3 Baths
  • 3,490 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $183/SF
  • 37 Days On Market

  Current Estimated Value $681,404

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  1051 Banister Rd, West Windsor, VT 05089
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  /13

  Not Listed For Sale

  2547 Rush Meadow Rd, Reading, VT 05062

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1970

  2547 Rush Meadow Rd, Reading, VT 05062

  Last Sold Summary

  • $381/SF
  • 33 Days On Market

  Last Sold Price $537,000

  Last Listing Agent Seth Warren Seth Warren Real Estate
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  /48

  $1,000,000 Sold Nov 13, 2025

  204 High Ridge Rd, Brownsville, VT 05037

  • 4 Beds
  • 3 Baths
  • 3,796 Sq Ft
  • Built 1990

  Last Sold Summary

  • 22% Below List Price
  • $263/SF
  • 90 Days On Market

  Current Estimated Value $977,527

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  204 High Ridge Rd, Brownsville, VT 05037
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  /38

  Est $844,552 Not Listed For Sale

  58 Cemetery Rd, West Windsor, VT 05089

  • 5 Beds
  • 3.5 Baths
  • 4,010 Sq Ft
  • Built 1850

  58 Cemetery Rd, West Windsor, VT 05089

  Last Sold Summary

  • 6% Above List Price
  • $200/SF
  • 56 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Seth Barbiero EXP Realty

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