Windsor County, VT Homes

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  /38

  $1,999,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vt Route 12, Barnard, VT 05031

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All of the well known amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
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  /34

  $565,000 Sold Jul 18, 2025

  • 1,471 Sq Ft
  • $384/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  31 Highland View Rd, Weston, VT 05161

  Welcome to your Vermont log home retreat, nestled on 3 serene, flat acres, this beautifully crafted log home with post-and-beam interior offers timeless charm and spacious living just minutes from downtown Weston and Londonderry.inside you are welcomed into a warm, open-concept layout where the living room, dining area, and kitchen flow effortlessly under wood-beamed ceilings. The main floor

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  31 Highland View Rd, Weston, VT 05161
• 

  

  

  /23

  Est $175,792 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,165 Sq Ft

  149 Main St, Windsor, VT 05089

  149 Main St, Windsor, VT 05089
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  /31

  $68,500

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn, Unit 434 QIV. Quarter Ownership. This top floor residence has beautiful valley facing views. Unit B Features: one bedroom with king bed, queen sleep sofa and queen wall bed, full kitchen, jetted tub, fireplace, entertainment center. This unit sleeps six and includes 1 locker for year round use. Other features include a large master bath offering his and her sinks, gas fireplace

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149
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  /53

  $862,000 Sold Jul 18, 2025

  • 4,020 Sq Ft
  • $214/SF
  • 63 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1850

  75 Baltimore Rd, North Springfield, VT 05150

  Welcome to Juniper Acres – Your Vermont Dream Awaits!Nestled on nearly 32 acres of peaceful countryside, this stunning Colonial Farmhouse offers room to grow, gather, and to roam. This fabulous family home blends timeless charm with thoughtful, modern updates featuring 5 bedrooms & 3 baths. Step inside and discover a spacious, sunlit interior designed for comfort and entertaining. The

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  75 Baltimore Rd, North Springfield, VT 05150
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  /40

  Est $496,202 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,024 Sq Ft

  29 Main St, Windsor, VT 05089

  29 Main St, Windsor, VT 05089
• 

  

  /25

  $359,000

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  78 Division St, Hartford, VT 05001

  This cozy, well cared for New Englander is move in ready. Enjoy the passive income as a two unit, or use it as a single family home. The choice is yours. The house has a nice boot room to organize all of those winter layers leading into a kitchen that flows into the living room. The first floor bedroom is a nice option. Public transportation is nearby and so are biking trails. Kilowatt field is a

  Josh Hunt Snyder Donegan Real Estate Group

  78 Division St, Hartford, VT 05001
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  /2

  $275,000 Sold Jul 18, 2025

  • Land
  • 2.74 Acres
  • $100,365 per Acre

  • 15 Days On Market

  111 Wellington Dr, Hartford, VT 05001

  2.74 acre lot with a 20 x 60 building with a 36 x 24 attached shed. Heated building with large overhead door. Perfect for your equipment, storage space located in the R3 district. Old septic design and well on property. Level lot, located behind Merchant Brothers garage, road through Merchant brothers is part of this lot.

  Richard Ballou RE/MAX Upper Valley

  111 Wellington Dr, Hartford, VT 05001
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  /36

  Est $872,712 Not Listed For Sale

  • 9 Beds
  • 8.5 Baths
  • 6,232 Sq Ft

  26 Main St, Windsor, VT 05089

  26 Main St, Windsor, VT 05089
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  /60

  $749,000

  • 4 Beds
  • 3.5 Baths
  • 2,729 Sq Ft

  419 Baileys Mills Rd, Reading, VT 05062

  Welcome to this enchanting, historic Cape nestled on 75.56 pristine acres along the scenic Mill Brook. Ideally located just five miles from GMHA, the property spans both sides of Baileys Mill Road, offering abundant opportunities for equestrians, hobby farmers & nature lovers alike. The land is a rare mix of open pastures, mature woodlands, flowing streams, and panoramic valley views. A network

  Laird Bradley Williamson Group Sothebys Intl. Realty

  419 Baileys Mills Rd, Reading, VT 05062
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  /45

  $750,000 Sold Jul 18, 2025

  • 1,360 Sq Ft
  • $551/SF
  • 132 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  145 Ledgewood Rd Unit D4, Ludlow, VT 05149

  Ledgewood On Okemo! Unit D4. This nicely updated 3 bedroom/2 bath condominium is conveniently located directly on the ski trail and on ground level so you can ski to your door! From your car, walk into a warm foyer that leads to your front door, which opens up into the mudroom and kitchen area. The kitchen has been tastefully updated with stainless appliances, tile backsplash and flooring, along

  Joseph Karl William Raveis Real Estate Vermont Properties

  145 Ledgewood Rd Unit D4, Ludlow, VT 05149
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  /34

  Est $409,341 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  37 Morningside Dr, Windsor, VT 05089

  37 Morningside Dr, Windsor, VT 05089
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  /37

  $1,185,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /40

  $525,000 Sold Jul 18, 2025

  • 2,023 Sq Ft
  • $260/SF
  • 164 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  988 Jenne Rd, Reading, VT 05062

  Located on one of Vermont’s most photographed roads, this iconic Vermont home offers unmatched views from broad windows, which create a warm, sun-soaked interiors. Master craftsmanship is seen throughout the house, from the stunning floors to the designer built-ins. The living room, kitchen, and dining room share an open plan centered around a magnificent stone fireplace. Sliders lead to outdoor

  Jennifer Kirkman KW Vermont Woodstock

  988 Jenne Rd, Reading, VT 05062
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  /37

  Est $439,937 Not Listed For Sale

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

  148 Hewett Rd, Windsor, VT 05089

  148 Hewett Rd, Windsor, VT 05089
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  /56

  $750,000

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

  477 Dunham Rd, Bethel, VT 05032

  A work of modern art. Words cannot describe the feeling you get when your eyes settle on this amazing place. Future owners need only appreciate the unique, creative, and thought provoking touches in this very interesting home.The builder/owners have created a family atmosphere centered around the massive stone fireplace, maple floor, open kitchen with impressive island, dining area, and a

  Dean Goulet Dunrovin Real Estate

  477 Dunham Rd, Bethel, VT 05032
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  /38

  $595,000 Sold Jul 18, 2025

  • 4,004 Sq Ft
  • $149/SF
  • 183 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1908

  20 Plumley Ave, Ludlow, VT 05149

  A charming and versatile property located on a quiet road in Ludlow Village with easy access to all area amenities including restaurants, Okemo Mountain Resort for skiing and golf and nearby Weston Playhouse. The large Victorian home with Carriage house was formerly the Plum Rose Tea House B&B. Features include beautiful antique wood detail throughout the main home, and spacious entertaining

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  20 Plumley Ave, Ludlow, VT 05149
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  /27

  Est $462,399 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  267 Taylor Dr Unit DRL, Windsor, VT 05089

  267 Taylor Dr Unit DRL, Windsor, VT 05089
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  /49

  $785,000

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  228 Leonard Rd, Sharon, VT 05065

  Welcome to your private Vermont retreat on nearly 24 acres of open meadows, woods, and a pristine spring-fed pond. Tucked away in complete seclusion and surrounded by 500 acres of undeveloped maple forest, this peaceful property offers unrivaled privacy and natural beauty. The charming 3-bedroom home features hardwood floors, a cozy wood stove, and a beautifully renovated kitchen with granite

  Mandolyn McIntyre Crow Real Broker LLC

  228 Leonard Rd, Sharon, VT 05065
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  /2

  $251,500 Sold Jul 17, 2025

  • 1,754 Sq Ft
  • $143/SF
  • 48 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  72 Chester Rd, Springfield, VT 05156

  This very nice, charming older home has a history that makes me happy. In 1935 when my father was just 17, my grandparents moved from the tiny Vermont village of Baltimore to the "big city" of Springfield, calling this grand house their new home. I grew up right across the road from where it once stood. In 1960, the Chester Road, or Route 11, was being straightened and improved, and a few houses

  Glenn Olney Barrett and Valley Associates Inc.

  72 Chester Rd, Springfield, VT 05156
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  /34

  Est $508,492 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,468 Sq Ft

  223 Taylor Dr, Windsor, VT 05089

  223 Taylor Dr, Windsor, VT 05089
• 

  

  /32

  $74,900

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

  185 Riverbend Way, Woodstock, VT 05091

  Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, Woodstock, VT 05091
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  /2

  $250,000 Sold Jul 16, 2025

  • 966 Sq Ft
  • $259/SF
  • 40 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1942

  186 Mountain View, Chester, VT 05143

  This Charming, well appointed home has much to offer! This turn key home is tucked away in a great location and neighborhood in walking distance to shops, food options and schools. The home itself has been updated and features many positives like almost all double pane windows, a recently redone paved driveway, an updated mudroom area, a metal standing seam roof, and much more. With a good size

  Thaddeus Abare Barrett and Valley Associates Inc.

  186 Mountain View, Chester, VT 05143
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  /27

  Est $233,333 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,154 Sq Ft

  159 Estey Ln, Windsor, VT 05089

  159 Estey Ln, Windsor, VT 05089
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  /29

  $169,500

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  1438 Gravelin Rd, Perkinsville, VT 05151

  Country Setting on a shared drive surrounded by 3 acres w/ a small pond. First floor has 1 BR, full bath, kitchen/dining area and living room. Lower level has 1 BR and laundry room. Heat is a propane Rannai direct vent, plus a lower-level pellet stove. Property is in need of repair but livable. This is an ideal candidate for a 203K loan.

  Don Chabot Town and Country Realty

  1438 Gravelin Rd, Perkinsville, VT 05151
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  /42

  $429,000 Sold Jul 16, 2025

  • 1,496 Sq Ft
  • $287/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  3450 N Perry Rd, Barnard, VT 05031

  This charming log home features an open kitchen/dining/living room with three cozy bedrooms, two full bathrooms, and a family room, perfect for comfortable living. The rustic wooden interior and warm atmosphere create a welcoming space for family and friends. Each floor has a propane wood stove for ambiance and extra warmth on those chilly winter nights, while a large wrap-around deck is perfect

  Susan Hickey Snyder Donegan Real Estate Group

  3450 N Perry Rd, Barnard, VT 05031
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  /29

  Est $237,235 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  28 Enright Ave, Windsor, VT 05089

  28 Enright Ave, Windsor, VT 05089
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  /59

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 3,862 Sq Ft

  699 Spear Cemetery Rd, Reading, VT 05062

  Situated amongst the finest equine estates in the region, Tuacknback Farm is an iconic landmark, best known as the most popular hold along the famed Vermont 100 ride. Located on a scenic country road, accessing the most extensive trail systems in New England, the entire property was impeccably orchestrated for ease with direct walk-in access to the connected stable and hay loft, and a wide

  Danny Kogut Williamson Group Sothebys Intl. Realty

  699 Spear Cemetery Rd, Reading, VT 05062
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  /51

  $1,575,000 Sold Jul 16, 2025

  • 3,916 Sq Ft
  • $402/SF
  • 120 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1850

  56 Elm St, Norwich, VT 05055

  If you believe in the statement, “it takes a village” and have been searching for a home in a community that values education and youth development, and is minutes away from Dartmouth College, consider 56 Elm Street in Norwich, Vermont. Elm Street is one of the prettiest village lanes in the state, with very little traffic, & walking distance to Marion Cross Elementary School, Dan and Whit’s

  Chris Lang LandVest, Inc/Woodstock

  56 Elm St, Norwich, VT 05055
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  /28

  Est $208,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  9 Dewey Ave, Windsor, VT 05089

  9 Dewey Ave, Windsor, VT 05089
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  /37

  $449,000

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

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056

  PRICE IMPROVEMENT on this Mountain Retreat in Plymouth – Between Killington & OkemoWelcome to your Vermont getaway! This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between Killington and Okemo for easy access to world-class skiing, snowboarding and year-round mountain and lake adventures.Enjoy breathtaking winter views

  Katie McFadden RE/MAX North Professionals

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056
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  /17

  $120,000 Sold Jul 16, 2025

  • Land
  • 5 Acres
  • $24,000 per Acre

  • 176 Days On Market

  0 Blackmer Blvd, Stockbridge, VT 05772

  1500 feet of frontage on the beautiful White River! This private water frontage along a level shoreline affords easy access to the river, for casual wading in the mesmerizing water! The property has a history of providing anglers with excellent fishing! There is an elevated area on the property that could provide the opportunity of a building site, in an area of minimal flood hazard. Access is

  John Wetmore Wetmore Real Estate

  0 Blackmer Blvd, Stockbridge, VT 05772
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  /40

  Est $347,669 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 936 Sq Ft

  39 Dairy Ln, Windsor, VT 05089

  39 Dairy Ln, Windsor, VT 05089
• 

  

  /57

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,585 Sq Ft

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

  Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and

  Katherine Burns William Raveis Real Estate Vermont Properties

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149
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  /19

  $85,000 Sold Jul 16, 2025

  • Land
  • 46.77 Acres
  • $1,817 per Acre

  • 195 Days On Market

  0 Hall Rd, Chester, VT 05143

  Private and secluded 46.77 acre wooded lot in Chester, VT.Property is in the current use program.The east side of the property runs along the Chester/Springfield line.15 minutes to I-91 and within driving distance to Okemo, Stratton, Magic & Bromley Ski Mountains.There is a slight view on the north east side of the property. There is a deeded ROW that is not maintained. This lot

  Jessica Samples BHG Masiello Keene

  0 Hall Rd, Chester, VT 05143
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  /37

  Est $372,332 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 3,176 Sq Ft

  40 Village Green, Windsor, VT 05089

  40 Village Green, Windsor, VT 05089
• 

  

  /42

  $945,000

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

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149

  It Truly is About Location! Sitting directly on the Sachem Trail this 3 bedroom townhome is one of the best locations on Okemo Mountain. You can access the trail either through the enlarged custom designed mudroom or step out onto the snow from the lower level sliding door. Either way this is the location that you are looking for! The kitchen is spacious, updated and open to the light-filled

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149
• 

  /2

  $190,000 Sold Jul 15, 2025

  • 1,502 Sq Ft
  • $126/SF
  • 40 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1860

  66 Mount Vernon St, Springfield, VT 05156

  This well maintained property has many perks! Including a recently installed roof, vinyl siding, freshly painted interior and much more. Located just minutes from shopping, restaurants and all of Springfields town amenities. With a good sized back yard and paved parking for two cars this property could be a great family home with plenty of room for growth!

  Thaddeus Abare Barrett and Valley Associates Inc.

  66 Mount Vernon St, Springfield, VT 05156
• 

  

  /15

  Est $148,419 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  807 County Rd, Windsor, VT 05089

  807 County Rd, Windsor, VT 05089
• 

  

  /60

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  442 Vermont 103, Chester, VT 05143

  Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

  Rachael Rogala Rachael Rogala Inc.

  442 Vermont 103, Chester, VT 05143

Showing Results 641 - 680, Page 17 of 18