Windsor, VT Homes

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  /59

  $3,300,000

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

  1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035

  Asa Greene traveled to Vermont in 1783 to establish a farm in the high hills in Bridgewater after serving in the American Revolution. 242 Years later the farmhouse still stands at the end of Old Bridgewater Hill Road after nearly 50 years of careful restoration and renovations made to accommodate an active, growing family. Creatively blending old & new the farmhouse takes advantage of an

  Laird Bradley Williamson Group Sothebys Intl. Realty

  1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035
• 

  Explore Bridgewater

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  /49

  $390,000 Sold Jun 05, 2025

  • 2,534 Sq Ft
  • $154/SF
  • 216 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1980

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Nestled in the scenic town of Bridgewater, Vermont, just 9 minutes from Killington Ski Resort and 25 minutes from Okemo, this charming 2-unit single-family home on 1 acre is a unique mountain retreat and a proven rental success. One of the standout features is the thoroughly renovated first-floor kitchen, which boasts elegant marble countertops and ample counter space, perfect for cooking family

  Jeremy Collins Ridgeline Real Estate

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /34

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  7429 Us Route 4, Bridgewater, VT 05034

  7429 Us Route 4, Bridgewater, VT 05034
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  /34

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
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  /27

  $275,000 Sold May 23, 2025

  • 2,171 Sq Ft
  • $127/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1965

  745 Vermont Route 100 Unit A3, Bridgewater, VT 05035

  Charming 2 Bedroom, 2 Bath Home with Loft in the Heart of Vermont. Nestled in the picturesques landscape of Vermont, this spacious 2-bed, 2-bath home with a cozy loft offers an abundance of natural light throughout, the perfect retreat for both relaxation and adventure. Enjoy the open concept living and dining area. The well-appointed kitchen features updated appliances, ideal for preparing

  Katie McFadden RE/MAX North Professionals

  745 Vermont Route 100 Unit A3, Bridgewater, VT 05035
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  /35

  Est $703,514 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  139 Jennes Rd, Bridgewater Corners, VT 05035

  139 Jennes Rd, Bridgewater Corners, VT 05035
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  /60

  $1,950,000

  • 4 Beds
  • 6.5 Baths
  • 4,562 Sq Ft

  73 Laber Rd, Bridgewater Corners, VT 05035

  Experience elevated Vermont living with this exceptional mountaintop estate, thoughtfully designed for both comfort and flexibility. Set on nearly 30 private acres, the residence combines timeless architectural style with expansive interiors and truly breathtaking panoramic views—including sightlines to 4,000-foot peaks and Killington’s ski trails.Inside, you’ll find a rare level of

  Keri Cole Williamson Group Sothebys Intl. Realty

  73 Laber Rd, Bridgewater Corners, VT 05035
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  /40

  $2,500,000 Sold May 02, 2025

  • 3,562 Sq Ft
  • $702/SF
  • 646 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1979

  2051 Goldcoast Rd, Bridgewater, VT 05091

  Peace. Tranquility. Big views. Located in the Chateauguay No Town Conservation Area near Woodstock, Wolfstar offers a haven with breathtaking views of the Green Mountains. Meticulously reenvisioned in 2008 by Vermont architect David Beilman, this 15-acre property, cherished as a second home for 35 years, provides complete privacy and understated luxury.The 3,562 sq ft shingle-style home

  Story Jenks LandVest, Inc/Woodstock

  2051 Goldcoast Rd, Bridgewater, VT 05091
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  /12

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,673 Sq Ft

  391 Phelps Rd, Woodstock, VT 05091

  391 Phelps Rd, Woodstock, VT 05091
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  /24

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  2179 U S 4, Bridgewater, VT 05035

  Looking for the tranquility of rural life? Charming, well built, vacation cabin, off the grid, on 30+ acres, with stunning views of Killington. Cabin has 2 bedrooms, 1 bath and a loft, 80% finished including roughed-in bath. Perfect get away from the bothers and troubles of the world, high above the valley with great views of the nearby mountains. Beautiful wood floors, full kitchen and lovely

  John MacGovern Dark Horse Realty

  2179 U S 4, Bridgewater, VT 05035
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  /14

  $245,000 Sold Jan 21, 2025

  • 550 Sq Ft
  • $445/SF
  • 24 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2017

  1340 Oxbow Rd, Woodstock, VT 05091

  If you are looking for a private, secluded getaway with a view that is off the grid but with all the comforts of home. You just found it. This little cozy home could be year round or a weekend retreat, with a deck that has a spectacular view. There is a fenced in small garden and a deeded short walk to a waterfall that comes deeded with the property. Recently installed solar panels and generator

  Ara Cardew BHG Masiello Keene

  1340 Oxbow Rd, Woodstock, VT 05091
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  /14

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  74 Upper Rd, Bridgewater Corners, VT 05035

  74 Upper Rd, Bridgewater Corners, VT 05035
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  /44

  $795,000

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  410 Upper Rd, Bridgewater Corners, VT 05035

  This 1892 Farmhouse offers two fully furnished and equipped 2-bedroom residences and is located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The property is privately sited above the Ottauquechee (an Abenaki name translated as 'Bright Water') River and directly across from Long Trial Brewing where a main

  Laird Bradley Williamson Group Sothebys Intl. Realty

  410 Upper Rd, Bridgewater Corners, VT 05035
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  /14

  $220,000 Sold Jan 08, 2025

  • 1,120 Sq Ft
  • $196/SF
  • 32 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1985

  2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Welcome to this delightful 3-bedroom, 1-bath ranch-style home nestled in the heart of scenic Bridgewater, Vermont. Perfectly situated on a quiet country road, this home offers the quintessential Vermont lifestyle with fresh air, and plenty of outdoor space. The single-level layout is ideal for easy living, featuring a spacious living room with large windows that let in plenty of natural light.

  Katie Ladue Gilbert KW Vermont Woodstock

  2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /40

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,472 Sq Ft

  19 Broad Brook Dr, Bridgewater, VT 05035

  19 Broad Brook Dr, Bridgewater, VT 05035
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  /60

  $859,000

  • 7 Beds
  • 7 Baths
  • 4,581 Sq Ft

  7137 Us Route 4, Bridgewater, VT 05034

  The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

  Laura Derderian Killington Valley Real Estate

  7137 Us Route 4, Bridgewater, VT 05034
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  /28

  $270,000 Sold Jan 07, 2025

  • 1,328 Sq Ft
  • $203/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  823 Goldcoast Rd, Bridgewtr Cor, VT 05035

  Highly desired Bridgewater location on Gold Coast Road minutes to the Killington Skyeship Gondola & Base Lodge, and the beautiful Village of Woodstock. Close to VAST snowmobile trails, and endless hiking/mountain biking trails. Five minutes to the legendary Long Trail Brewery. This 3 bedroom, 2 full bath home is set on 2.6 tranquil, well-maintained acres. The home has an eat in kitchen, spacious

  Marni Rieger KW Vermont-Killington

  823 Goldcoast Rd, Bridgewtr Cor, VT 05035
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  /39

  Est $744,935 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,943 Sq Ft

  629 N Bridgewater Rd, Bridgewater, VT 05034

  629 N Bridgewater Rd, Bridgewater, VT 05034
• 

  

  /17

  $835,000

  • Land
  • 150 Acres
  • $5,567 per Acre

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

  150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

  John Wetmore Wetmore Real Estate

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
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  /15

  $126,000 Sold Nov 18, 2024

  • 1,404 Sq Ft
  • $90/SF
  • 53 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  16 Geno Rd, Bridgewater Corners, VT 05035

  Here's a great opportunity to make this country location your own! There's some sweat equity needed but there's over an acre of quiet country for you to enjoy while being a short drive from Killington ski area and down the road from the Long Trail Brewing Company. The interior features an open feeling with the large living room open to the dining area with the kitchen just off to the side. The

  A.J. Bellville Bellville Realty

  16 Geno Rd, Bridgewater Corners, VT 05035
• 

  

  /11

  Not Listed For Sale

  • 11 Beds
  • 5 Baths
  • 6,095 Sq Ft

  7465 U S 4, Woodstock, VT 05091

  7465 U S 4, Woodstock, VT 05091
• 

  

  /34

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,373 Sq Ft

  58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035

  Main floor two-bedroom, 2-bathroom condo with lovely mountain views. An open floor plan which outfits the living room, dining and kitchen with plenty of natural light. In addition is the primary ensuite, 3/4-bathroom, second bedroom and office/den. Common space includes a coin operated laundry facility, shared deck, gazebo, and a storage room, along with 2 parking spaces per unit. The property is

  Terry Davis Williamson Group Sothebys Intl. Realty

  58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035
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  /26

  $1,115,000 Sold Nov 14, 2024

  • 2,250 Sq Ft
  • $496/SF
  • 107 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091

  If you are looking for a beautiful and quiet off-the-grid mountain retreat, look no further. This custom log home is situated on 106+ acres with incredible mountain views, brooks, pond, orchard, hiking trails, and abundant wildlife and it is just minutes from the Killington ski area and the charming town of Woodstock, VT. The interior of the home is best described as having the feeling of a

  Kris Lippi Get Listed Realty

  317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091
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  /33

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft

  58 Valley View Rd Unit 2, Bridgewater Corners, VT 05035

  58 Valley View Rd Unit 2, Bridgewater Corners, VT 05035
• 

  

  /10

  $129,000

  • Land
  • 3.00 Acres
  • $43,000 per Acre

  0 Goldcoast Rd, Bridgewater, VT 05034

  Come see this beautiful piece of Vermont!! Conveniently located in the town of Bridgewater that boasts no zoning. Enjoy all the outdoor adventures that Vermont has to offer nearby, minutes to world class skiing and riding, mountain biking, surrounded by snowmobiling trails, golf, Long Trail Brewery, Plymouth’s trio of lakes, and the quintessential Vermont town of Woodstock. Visualize your own

  Will Spanos KW Vermont-Killington

  0 Goldcoast Rd, Bridgewater, VT 05034
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  /6

  $120,000 Sold Oct 11, 2024

  • 1,792 Sq Ft
  • $67/SF
  • 8 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1973

  75 Pearson Rd, Bridgewater, VT 05035

  Check out this 3BR/ 1BA fixer upper home in the beautiful climate haven of Bridgewater, Vermont, just minutes from Woodstock and the world renowned ski resorts Killington and Okemo! Offering easy access off the main road, this property still maintains plenty of privacy, backing up to hundreds of acres of woods. With a mountain spring water source and a peaceful brook, this charming property is

  Tucker Adirondack Lange Vermont Real Estate Company

  75 Pearson Rd, Bridgewater, VT 05035
• 

  

  /23

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  6769B U S 4 Unit B, Bridgewater, VT 05034

  6769B U S 4 Unit B, Bridgewater, VT 05034
• 

  

  /28

  $239,000

  • 3 Beds
  • 1,984 Sq Ft

  18 Oak Chapel Rd, Bridgewater, VT 05035

  Discover the potential of this unique fixer-upper property nestled on 0.64 acres, featuring not one, but two distinct buildings awaiting your vision.Step into the main 3-bedroom white house, a fixer-upper's dream filled with endless possibilities. The front porch offers a seasonal retreat with stunning Vermont mountain views - envision it transformed into a year-round haven with a few

  Chelsea Bevis KW Vermont Woodstock

  18 Oak Chapel Rd, Bridgewater, VT 05035
• 

  

  /27

  $500,000 Sold Oct 11, 2024

  • 1,512 Sq Ft
  • $331/SF
  • 74 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  2294 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  BIG PRICE REDUCTION!! Newly built three-bedroom log home on 6+ acres with astonishing 80x30 garage/shop. Hobbyists, mechanics, tinkerers, car/ custom RV builders take notice- the garage is piped for radiant in floor heating and boasts a 12 x 12 overhead door; large campers and buses are accommodated easily. In the log home, the open-concept kitchen/living/dining features a cathedral ceiling and

  Geoff Eckler Real Broker LLC

  2294 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /12

  Not Listed For Sale

  0 Old Bridgewater Hill Rd, Bridgewater, VT 05035

  0 Old Bridgewater Hill Rd, Bridgewater, VT 05035
• 

  

  /40

  $799,000

  • 7 Beds
  • 6 Baths
  • 5,028 Sq Ft

  52 Upper, Bridgewater, VT 05035

  A "turn-key" commercial opportunity in a highly visible location! Being well situated between the world class skiing of Killington and the numerous amenities of historic Woodstock Village entrepreneurial dreams for this diverse property can easily take flight! Within this classic New England style structure are a professionally appointed and immaculate commercial kitchen, spacious dining rooms,

  John Wetmore Wetmore Real Estate

  52 Upper, Bridgewater, VT 05035
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  /39

  $290,000 Sold Sep 20, 2024

  • 1,239 Sq Ft
  • $234/SF
  • 16 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  5713 U S 4, Bridgewater, VT 05035

  Prime Location, Limitless Possibilities: Nestled between Woodstock and the thriving Killington Resort area, this property is perfect for year-round living or as a second home. Featuring two bedrooms, two baths, light filled rooms, super cool AC, and a fun open floor plan. A multi-functional bonus building with four rooms on the main level, one 1100 square foot great room on the second floor and

  Dorothy Griswold The Clerkin Agency, P.C.

  5713 U S 4, Bridgewater, VT 05035
• 

  

  /20

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft

  58 Valley View Rd Unit 3, Bridgewater Corners, VT 05035

  58 Valley View Rd Unit 3, Bridgewater Corners, VT 05035
• 

  

  /36

  $995,000 Pending

  • 4 Beds
  • 1 Bath
  • 2,330 Sq Ft

  61 Putnam Rd, Bridgewater Corners, VT 05035

  Enjoy a peaceful, park-like setting in the Broad Brook valley at one of Bridgewater’s most iconic farmhouses. Both floors of the home feature large rooms, high ceilings, and beautiful wide-board flooring. The main floor has a large eat-in kitchen with connected butler’s pantry/ mudroom, spacious formal dining room with views, living room, parlor, and a bedroom with a bath just outside the door.

  Geoff Eckler Real Broker LLC

  61 Putnam Rd, Bridgewater Corners, VT 05035
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  /40

  $155,000 Sold Aug 28, 2024

  • 3,350 Sq Ft
  • $46/SF
  • 24 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1850

  140 Hale Hollow Rd, Bridgewater Corners, VT 05035

  Charming 1850 Colonial in scenic Rural Vermont opportunity awaits! Embrace the potential of this expansive 1850 Colonial home, ready for your vision to bring it back to life. Revel in the beauty of its original wood beams, floors, and wide open rooms. This spacious home boasts 4 bedrooms in the main house, including a separate in-law apartment, offering versatile living arrangements and endless

  Jeremy Collins Ridgeline Real Estate

  140 Hale Hollow Rd, Bridgewater Corners, VT 05035
• 

  

  /16

  Est $342,883 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  5 Broad Brook Dr, Bridgewater, VT 05035

  5 Broad Brook Dr, Bridgewater, VT 05035
• 

  

  /21

  $340,000 Sold Aug 23, 2024

  • 864 Sq Ft
  • $394/SF
  • 1 Day On Market

  • 2 Beds
  • 1 Bath
  • Built 1979

  180 Valley Park Unit A-1, Killington, VT 05751

  Rare to market Valley Park unit. Are you looking for a place in Killington to call your own? Here it is, situated in the valley below Killington Resort, just minutes to Pico Mountain or Skyeship Gondola this location is easy access all year. Two bedrooms upstairs leaves the lower level just to the open concept Livingroom and Kitchen. On the back of the condo you will find a private large deck, a

  Patricia Balbirnie Four Seasons Sotheby's Int'l Realty

  180 Valley Park Unit A-1, Killington, VT 05751
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  /10

  Est $211,065 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft

  6769 Us Route 4 Unit A, Bridgewater, VT 05034

  6769 Us Route 4 Unit A, Bridgewater, VT 05034
• 

  /2

  $1,250,000 Sold Dec 10, 2024

  • 3,200 Sq Ft
  • $391/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2011

  745 Wemple Knoll Rd, Bridgewater, VT 05035

  A rare opportunity to own an outstanding off-grid 4000 s/f house on 246.22 private acres in the heart of Bridgewater. This property sits on top of a beautiful mountain at the end of the road with its own pond and is close to skiing. Wemple Knoll is a tight, off-grid property with solar panels, battery back-up, heating system of radiant heat (solar powered). This is a well insulated property with

  John Bassette Bassette Real Estate Group

  745 Wemple Knoll Rd, Bridgewater, VT 05035
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,965 Sq Ft

  3 Green Gate Rd, Woodstock, VT 05091

  3 Green Gate Rd, Woodstock, VT 05091

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