West Windsor Homes

• 

  

  

  /43

  $1,325,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  325 Cemetery Rd, West Windsor, VT 05089

  Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky.This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

  Story Jenks LandVest, Inc/Woodstock

  325 Cemetery Rd, West Windsor, VT 05089
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• 

  

  

  /21

  $2,800 per month

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  295 Hotel Rd Unit 17, Brownsville, VT 05037

  Spacious and bright condo on Ascutney Mountain loft area, cathedral ceilings and some much light!. Fireplace in living room, dining area with balcony, updated kitchen and even an entry enclave. 3 bedrooms with 3 full baths. 1 bed/bath on 1st floor. 2 bedrooms, 2 baths, multiple closets and a sitting area on the upper level. Can be furnished. Outside abounds with nature with walking trails,

  Crystal Moses Crystal Moses

  295 Hotel Rd Unit 17, Brownsville, VT 05037
• 

  

  

  /12

  $140,500 Sold May 06, 2025

  • 506 Sq Ft
  • $278/SF
  • 92 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1966

  789 Ski Tow Rd Unit 1, West Windsor, VT 05037

  Well maintained end unit Nordic Haus 1BR/BA condo ready for new owners. Corner unit with covered porch, newer windows, hot water heater and flooring. Perfect for first time buyers, investment or vacation property. Steps from Ascutney Outdoors for hiking, biking, skiing and winter tubing. Close proximity to I91.

  Scott Monahan Williamson Group Sothebys Intl. Realty

  789 Ski Tow Rd Unit 1, West Windsor, VT 05037
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  /35

  Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,772 Sq Ft

  951 Ski Tow Rd, West Windsor, VT 05037

  951 Ski Tow Rd, West Windsor, VT 05037
• 

  

  

  /15

  $140,000

  • 1 Bed
  • 1 Bath
  • 602 Sq Ft

  815 Ski Tow Rd Unit 3, Brownsville, VT 05037

  Tired of paying high rent? Here is a terrific opportunity to dive into home ownership! Featuring 1 BR, and 1 BA, with loft space it would also make a great second home.This condo is very well maintained with sunny spaces and a convenient updated kitchen. Lovely views from the private and covered porch, will help you unwind after a busy day. A perfect spot to enjoy your morning coffee.

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  815 Ski Tow Rd Unit 3, Brownsville, VT 05037
• 

  

  /22

  $100,000 Sold May 05, 2025

  • Land
  • 5 Acres
  • $19,194 per Acre

  • 29 Days On Market

  00 Weeden Hill Rd, West Windsor, VT 05089

  This gently rolling and sunny lot has frontage on both Weeden Hill and Bald Hill. Likely driveway access will be off of Weeden Hill. Owner will consider owner financing some portion of the purchase price for a window of time. This is a lovely 5.21 acre parcel that has both wooded and open acres. It is ready to build. The septic design plans are State permitted and in place for a four bedroom

  John Bassette Bassette Real Estate Group

  00 Weeden Hill Rd, West Windsor, VT 05089
• 

  

  /25

  Est $547,396 Not Listed For Sale

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

  124 Village Ln, West Windsor, VT 05037

  124 Village Ln, West Windsor, VT 05037
• 

  

  /48

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,764 Sq Ft

  204 High Ridge Rd, Brownsville, VT 05037

  Beautiful 4 BR 3 Ba custom built home in West Windsor. 33.5 acres with a view of Mt Ascutney, & functional stand alone work shop (idealfor office/shop/or B&B with permits & update),swimming pond, pond houseand privacy- 3rd(last) home on private road. The home has a deck & large front porch, an open floor plan and lots of natural light. Spacious kitchen, dining area with woodstove, sunken living

  Dana Waters Dark Horse Realty

  204 High Ridge Rd, Brownsville, VT 05037
• 

  

  /11

  $200,000 Sold Apr 25, 2025

  • 1,672 Sq Ft
  • $120/SF
  • 56 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1995

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

  Spacious 3 BR 3 B walk up condominium in the Windsor Building at Ascutney Mountain Resort, home of Ascutney Outdoors! Open, fireplaced LR/Dining w sliding glass door to Balcony. Near restaurant & Brownsville Butcher & Pantry.Skiing, Tubing and Mountain Bike & Hiking trails all within walking distance. Recent upgrades to building include roof, siding, windows and sliders. Less than 30 minutes to

  Dana Waters Dark Horse Realty

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

  

  /40

  Est $1,551,797 Not Listed For Sale

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

  89 Silver Hill Rd, West Windsor, VT 05089

  89 Silver Hill Rd, West Windsor, VT 05089
• 

  

  /16

  $435,000

  • Land
  • 10 Acres
  • $42,647 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
• 

  

  /15

  $191,000 Sold Apr 24, 2025

  • 914 Sq Ft
  • $209/SF
  • 93 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1995

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

  Don't miss out on this affordable slope side adventure. Nestled at the base of Ascutney Mountain, this fully updated 2-bedroom, 2-bathroom condo is the ultimate retreat for outdoor enthusiasts and active families. Ascutney Outdoors offers an accessible and affordable skiing and snowboarding experience, and the tubing hill right outside your door makes winter fun effortless for kids and adults

  Laurie Kirkpatrick Four Seasons Sotheby's Int'l Realty

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

  

  /40

  Est $557,319 Not Listed For Sale

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

  3052 Brownsville Hartland Rd, West Windsor, VT 05089

  3052 Brownsville Hartland Rd, West Windsor, VT 05089
• 

  

  /16

  $435,000

  • 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
• 

  

  /40

  $1,225,000 Sold Apr 02, 2025

  • 4,411 Sq Ft
  • $278/SF
  • 12 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  384 Skyhawk Ln, Brownsville, VT 05037

  384 SKYHAWK LANE- Beautiful custom-built 4 bedroom & 5 bath timberframe home sited on a generous 1 acre lot at the base of Mount Ascutney. The house is being offered Furnished so is turnkey and move-in ready. A vaulted ceiling living room with 20-foot stone fireplace flows seamlessly into the gourmet kitchen and dining area and is flanked by a sizable deck off the back side of the house, a prime

  David Donegan Snyder Donegan Real Estate Group

  384 Skyhawk Ln, Brownsville, VT 05037
• 

  

  /19

  Est $370,739 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,361 Sq Ft

  2253 Brownsville Hartland Rd, West Windsor, VT 05089

  2253 Brownsville Hartland Rd, West Windsor, VT 05089
• 

  

  /49

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,830 Sq Ft

  1777 Bible Hill Rd, Brownsville, VT 05037

  This tidy, well orchestrated Custom Timber Frame Cape is the perfect package! You will love the beautiful, bright spaces that connect seamlessly for every day living and entertaining. Tasteful updates and improvements throughout, this house was designed with convenience in mind. Gleaming hardwood floors run through the main and second level. The roomy country kitchen has soapstone counters, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1777 Bible Hill Rd, Brownsville, VT 05037
• 

  

  /18

  $278,416 Sold Mar 20, 2025

  • 1,500 Sq Ft
  • $186/SF
  • 23 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  108 Mountains Edge Rd Unit 302, Brownsville, VT 05037

  Perfectly sited in an ideal Upper Valley location, this Mount Ascutney Resort condo offers an abundance of hiking trails, mountain biking, and rope tow/t-bar skiing all just outside your door. The light-filled, open concept end unit features 3 bedrooms–each with its own full bath for convenience and privacy–and a cozy wood-burning fireplace in the living room, making it perfect for comfortably

  Bonnie Bergeron Snyder Donegan Real Estate Group

  108 Mountains Edge Rd Unit 302, Brownsville, VT 05037
• 

  

  /29

  Est $426,665 Not Listed For Sale

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

  406 Rush Meadow Rd, Brownsville, VT 05037

  406 Rush Meadow Rd, Brownsville, VT 05037
• 

  

  /35

  $621,000

  • 3 Beds
  • 3 Baths
  • 2,915 Sq Ft

  1643 Hammond Hill Rd, West Windsor, VT 05089

  Discover your homestead dream on 8 acres of beautiful land that’s been incredibly loved and improved upon in the last 18 years. The classic farmhouse has hardwood floors, big kitchen, dining room and spacious living with den, 2 bathrooms and 2 bedrooms. In addition, this unique property now has a 2 car garage and living space above it that includes large office and1-BR apt for guests, family or

  Daniel Preston KW Vermont Woodstock

  1643 Hammond Hill Rd, West Windsor, VT 05089
• 

  

  /40

  $340,000 Sold Feb 14, 2025

  • 1,608 Sq Ft
  • $211/SF
  • 124 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  690 Jewett Rd, West Windsor, VT 05037

  The perfect peaceful home in beautiful Brownsville, VT! This 3 bedroom 2 bath home on 1 acre overlooks the community pond from the spacious wrap around deck & living room with full size sliding glass doors. The main level includes a kitchen, dining area with built in table & benches, & living room with a wood burning fireplace. There is also a bedroom & full bathroom on this level. The walk out

  Amy Hill EXP Realty

  690 Jewett Rd, West Windsor, VT 05037
• 

  

  /18

  Not Listed For Sale

  00 Brownsville Hartland Rd, West Windsor, VT 05037

  00 Brownsville Hartland Rd, West Windsor, VT 05037
• 

  

  /46

  $1,665,000

  • 7 Beds
  • 6 Baths
  • 5,774 Sq Ft

  310 Pierce Hill Rd, West Windsor, VT 05089

  Unique Two-Home Property with Stunning Mountain Views.Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity.The newer side of the home showcases beautiful hardwood

  Gary Coger Four Seasons Sotheby's Int'l Realty

  310 Pierce Hill Rd, West Windsor, VT 05089
• 

  

  /15

  $199,000 Sold Feb 07, 2025

  • 1,604 Sq Ft
  • $124/SF
  • 20 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1995

  295 Hotel Rd Unit 19/19A, Brownsville, VT 05037

  Attractive 3 BR 3 BA walk up condominium in the Windsor Building at Ascutney Mountain home of Ascutney Outdoors! Open fireplaced LR/Dining opens to Deck overlooking the Tubing Hill. Enjoy all the action right out your door! *Covenants & Right of First Refusal. The Mountain offers inexpensive skiing on natural snow. Mountain biking, hiking, cross country skiing, snow shoeing. Approx. 1300 acre

  Dana Waters Dark Horse Realty

  295 Hotel Rd Unit 19/19A, Brownsville, VT 05037
• 

  

  /40

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 4,281 Sq Ft

  4281 Rush Meadow Rd, West Windsor, VT 05037

  4281 Rush Meadow Rd, West Windsor, VT 05037
• 

  

  /13

  $1,483,000

  • Land
  • 103 Acres
  • $14,384 per Acre

  1503 Rush Meadow Rd, West Windsor, VT 05089

  An extremely rare opportunity to become the steward of one of the areas last remaining intact farmsteads. The 103 acres has traditionally served as a highly productive self sustaining property. Its roughly 37 acres of well drained, rich soiled hayfields lend themselves with their southern exposure to a multitude of agricultural pursuits. While the remaining 66 acres is a well managed mixed

  Wade Treadway Wade I Treadway Real Estate

  1503 Rush Meadow Rd, West Windsor, VT 05089
• 

  

  /29

  $460,000 Sold Jan 15, 2025

  • 2,388 Sq Ft
  • $193/SF
  • 65 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1975

  720 Skyhawk Ln, Brownsville, VT 05037

  Welcome to 720 Skyhawk Lane, a stunning 4-bed, 3.5-bath retreat where VT charm meets modern living. This chalet has been completely renovated to include a new kitchen, appliances, bathrooms, and a state of the art, energy efficient heating system to name a few. Tucked away on picturesque Mount Ascutney, this home offers breathtaking mountain views. You will treasure gorgeous sunsets off the

  Daniel Preston KW Vermont Woodstock

  720 Skyhawk Ln, Brownsville, VT 05037
• 

  

  /13

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 506 Sq Ft

  789 Ski Tow Rd, West Windsor, VT 05037

  789 Ski Tow Rd, West Windsor, VT 05037
• 

  

  /24

  $1,483,000

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft

  1503 Rush Meadow Rd, West Windsor, VT 05089

  Rush Meadow Road is renowned for its equestrian properties and intact farmsteads. This 103 acre farmstead is one of the last multi generational farmsteads that have remained in continual ownership for over a century. Operated as a successful dairy farm for many years, the fields and woodlands have been continually maintained to a high standard. Great hay production, excellent sugarbush and

  Wade Treadway Wade I Treadway Real Estate

  1503 Rush Meadow Rd, West Windsor, VT 05089
• 

  

  /47

  $925,000 Sold Jan 08, 2025

  • 2,000 Sq Ft
  • $462/SF
  • 42 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  3894 Rush Meadow Rd, West Windsor, VT 05089

  Located in the premiere Rush Meadow region of West Windsor in the heart of horse country, this magical, pastoral property checks every box: spectacular established perennial beds, including extensive banks of show-stopping lilacs; spring-fed swimming pond with dock; expansive meadow and trails for hiking, snowshoeing and cross country skiing; seasonal and year-round brooks with heavy duty

  Danny Kogut Williamson Group Sothebys Intl. Realty

  3894 Rush Meadow Rd, West Windsor, VT 05089
• 

  

  /17

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  205 Mountains Edge Rd Unit 205, West Windsor, VT 05037

  205 Mountains Edge Rd Unit 205, West Windsor, VT 05037
• 

  

  /44

  $299,500 Under Contract

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

  108 Mountains Edge Rd Unit 307, Brownsville, VT 05037

  Beautiful Fully Furnished Home with a Solid Airbnb Rental History. This charming VT townhouse features 3 bedrooms, 2.5 baths and has a wonderful flow for gathering. Bright and cheerfully decorated, it is currently designed to sleep eight. The mudroom entryway has natural light and a coat closet and upon entering you will be greeted by a well-appointed living space with every familiar comfort. The

  John Bassette Bassette Real Estate Group

  108 Mountains Edge Rd Unit 307, Brownsville, VT 05037
• 

  

  /33

  $725,000 Sold Nov 15, 2024

  • 3,794 Sq Ft
  • $191/SF
  • 156 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  781 Silver Hill Rd, West Windsor, VT 05089

  Beautifully constructed Davis Timber frame home in the desirable Silver Hill region of West Windsor. Spacious, bright rooms connect beautifully to private outdoor deck and screened porch overlooking a large swimming pond. The generous living room runs front to back anchored by a beautiful stone fireplace with warm golden hardwood floors, and exposed beam structure. The open concept kitchen offers

  Danny Kogut Williamson Group Sothebys Intl. Realty

  781 Silver Hill Rd, West Windsor, VT 05089
• 

  

  /37

  Est $507,411 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  3328 Brownsville Hartland Rd, West Windsor, VT 05089

  3328 Brownsville Hartland Rd, West Windsor, VT 05089
• 

  

  /39

  $749,000 Under Contract

  • 5 Beds
  • 2.5 Baths
  • 3,443 Sq Ft

  938 Bible Hill Rd, Brownsville, VT 05037

  Outdoor lover’s heaven! Scenic 4 season's views, peaceful country setting you will enjoy in this well-built contemporary cape that stages Mt Ascutney from your own backyard! The home features 4-5 bedrooms, 2.5 baths, newly renovated gourmet kitchen with stone counters, hickory cabinets, stainless steel appliances, bamboo flooring, vaulted ceiling in the living room with a wood fireplace and

  Delia Wallace Coldwell Banker LIFESTYLES - Hanover

  938 Bible Hill Rd, Brownsville, VT 05037
• 

  

  /33

  $975,000 Sold Oct 29, 2024

  • 2,988 Sq Ft
  • $326/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  5434 Rush Meadow Rd, West Windsor, VT 05089

  5434 RUSH MEADOW- Lovely reproduction Cape in prime Rush Meadow neighborhood. This is a wonderful, peaceful setting- a perfect balance of bright sunshine, pasture, and wooded landscape. The house is immaculate and well designed with an open floor plan and historic touches throughout. The first floor master suite is spacious with a private deck. There are two large bedrooms on the second floor, a

  David Donegan Snyder Donegan Real Estate Group

  5434 Rush Meadow Rd, West Windsor, VT 05089
• 

  

  /40

  Est $818,168 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,078 Sq Ft

  456 Harrington Rd, Brownsville, VT 05037

  456 Harrington Rd, Brownsville, VT 05037
• 

  

  /44

  $299,500 Under Contract

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

  108 Mountains Edge Rd Unit 307, Brownsville, VT 05037

  Beautiful Fully Furnished Home with a Solid Airbnb Rental History. This charming VT townhouse features 3 bedrooms, 2.5 baths and has a wonderful flow for gathering. Bright and cheerfully decorated, it is currently designed to sleep eight. The mudroom entryway has natural light and a coat closet and upon entering you will be greeted by a well-appointed living space with every familiar comfort. The

  John Bassette Bassette Real Estate Group

  108 Mountains Edge Rd Unit 307, Brownsville, VT 05037
• 

  

  /25

  $380,000 Sold Oct 25, 2024

  • 1,140 Sq Ft
  • $333/SF
  • 8 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  46 Yodel Valley Rd, West Windsor, VT 05089

  Please join us for an OPEN HOUSE Saturday, September 14th 10 AM - 12 PM! Nestled at the end of a private road amidst the tranquil woods, this charming chalet-style home offers a serene escape on 3 acres and just moments from Ascutney Mountain. Whether you seek a private getaway, year round living, or an investment opportunity (the current owners proving a successful and conservative AirBnB income

  Tyler Hall BHHS Verani Upper Valley

  46 Yodel Valley Rd, West Windsor, VT 05089
• 

  

  /38

  Est $461,506 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,598 Sq Ft

  164 John Meyers Rd, West Windsor, VT 05089

  164 John Meyers Rd, West Windsor, VT 05089

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