36,189

Windsor County, VT Homes

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  • /60

    $2,450,000

    • 5 Beds
    • 6 Baths
    • 5,625 Sq Ft

    16 Olcott Rd, Norwich, VT 05055

    16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and

    David Donegan Snyder Donegan Real Estate Group

    16 Olcott Rd, Norwich, VT 05055
  • /59

    $495,000 Sold Oct 02, 2025

    973 Route 106, Reading, VT 05062

    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft
    • Built 1835

    Last Sold Summary

    • $243/SF
    • 5 Days On Market

    Current Estimated Value $490,117

    Last Listing Agent John Bassette Bassette Real Estate Group

    973 Route 106, Reading, VT 05062
    • /29

      Est $393,014 Not Listed For Sale

      59 Birch Ln, Ludlow, VT 05149

      • 3 Beds
      • 2 Baths
      • 2,500 Sq Ft
      • Built 2016
      59 Birch Ln, Ludlow, VT 05149

      Last Sold Summary

      • 19% Above List Price
      • $132/SF
      • 29 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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
  • /40

    $1,625,000 Sold Sep 29, 2025

    441 Spruce Way, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 2,619 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $620/SF
    • 6 Days On Market

    Current Estimated Value $1,657,878

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    441 Spruce Way, Woodstock, VT 05091
    • /41

      Not Listed For Sale

      291 Hard Rd, Hartford, VT 05059

      • 3 Beds
      • 2.5 Baths
      • 2,097 Sq Ft
      • Built 1972
      291 Hard Rd, Hartford, VT 05059

      Last Sold Summary

      • $246/SF
      • 142 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Heather Ashline BHHS Verani Upper Valley

  • /60

    $3,275,000

    • 4 Beds
    • 4.5 Baths
    • 4,708 Sq Ft

    207 Willey Hill Rd, Norwich, VT 05055

    207 WILLEY HILL ROAD- Gorgeous, recently updated, sophisticated home a stone's throw away from Norwich, Hanover, Dartmouth College, and the best of the Upper Valley. Expertly renovated by renowned builders O’Hara & Gercke, the result is a seamless blend of luxury, charm, and comfort. The sunlit gourmet kitchen is both functional and elegant and commands breathtaking views of the pond, with an

    David Donegan Snyder Donegan Real Estate Group

    207 Willey Hill Rd, Norwich, VT 05055
  • /32

    $700,000 Sold May 30, 2025

    13 Golf Ave, Woodstock, VT 05091

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft
    • Built 1880

    Last Sold Summary

    • $461/SF
    • 0 Days On Market

    Current Estimated Value $717,393

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    13 Golf Ave, Woodstock, VT 05091
    • /30

      Not Listed For Sale

      14 Cherry Tree Ln, Hartland, VT 05001

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2014
      14 Cherry Tree Ln, Hartland, VT 05001

      Last Sold Summary

      • $166/SF
      • 40 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Susan Cole Susan Cole Realty Group, LLC

  • /46

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 6,096 Sq Ft

    115 Eastman Rd, South Woodstock, VT 05071

    Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

    Keri Cole Williamson Group Sotheby's International Realty

    115 Eastman Rd, South Woodstock, VT 05071
  • /26

    $193,000 Sold Oct 17, 2025

    37 Coolidge Rd, Springfield, VT 05156

    • 2 Beds
    • 1 Bath
    • 942 Sq Ft
    • Built 1929

    Last Sold Summary

    • 2% Above List Price
    • $205/SF
    • 66 Days On Market

    Current Estimated Value $190,094

    Last Listing Agent Betsy Adamovich Real Broker LLC

    37 Coolidge Rd, Springfield, VT 05156
    • /24

      Est $211,616 Not Listed For Sale

      253 Old Quechee Rd Unit 4C, Hartford, VT 05001

      • 2 Beds
      • 2 Baths
      • 1,063 Sq Ft
      • Built 1978
      253 Old Quechee Rd Unit 4C, Hartford, VT 05001

      Last Sold Summary

      • 8% Below List Price
      • $216/SF
      • 153 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Daniel Preston KW Vermont Woodstock

  • /32

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,592 Sq Ft

    26 Mount Peg Rd Unit A, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, Woodstock, VT 05091
  • /37

    $505,000 Sold Oct 24, 2025

    56 Main St, Ludlow, VT 05149

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $230/SF
    • 191 Days On Market

    Current Estimated Value $513,034

    Last Listing Agent Betty McEnaney Diamond Realty

    56 Main St, Ludlow, VT 05149
    • /54

      Est $320,710 Not Listed For Sale

      177 Church St, Bethel, VT 05032

      • 3 Beds
      • 1.5 Baths
      • 2,230 Sq Ft
      • Built 1894
      177 Church St, Bethel, VT 05032

      Last Sold Summary

      • 11% Above List Price
      • $130/SF
      • 13 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

  • /46

    $399,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 2,751 Sq Ft

    3466 Vt Route 103 N, Chester, VT 05143

    Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the

    Betsy Adamovich Real Broker LLC

    3466 Vt Route 103 N, Chester, VT 05143
  • /46

    $250,000 Sold Nov 18, 2025

    2665 Brook Rd, Cavendish, VT 05142

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $200/SF
    • 53 Days On Market

    Last Listing Agent Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    2665 Brook Rd, Cavendish, VT 05142
    • /14

      Est $68,528 Not Listed For Sale

      102 Railroad St, Royalton, VT 05068

      • 1 Bed
      • 1 Bath
      • 700 Sq Ft
      • Built 1975
      102 Railroad St, Royalton, VT 05068

      Last Sold Summary

      • 14% Above List Price
      • $86/SF
      • 84 Days On Market

      Last Sold Price $60,000

      Last Listing Agent Jackie Jameson Jameson Real Estate

  • /56

    $3,400,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,485 Sq Ft

    2769 Cloudland Rd, Pomfret, VT 05067

    Breathtaking long range views of Killington Peak and Saskadena 6 greet you as you wind your way up to your private slice of Heaven. Situated on nearly 91 acres, this spectacular property offers everything, from the views and open fields to the saltwater pool tucked nicely into the hillside to the trails running throughout the woods and a lovely stone patio aligned perfectly for evening sunsets.

    Dan Noble Snyder Donegan Real Estate Group

    2769 Cloudland Rd, Pomfret, VT 05067
  • /11

    $213,000 Sold Jun 06, 2025

    644 Vermont 12, Hartland, VT 05048

    • Land
    • 33.2 Acres
    • $6,416 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 508 Days On Market

    Current Estimated Value $208,497

    Last Listing Agent Chris Crowe Quechee Lakes Real Estate Center

    644 Vermont 12, Hartland, VT 05048
    • /39

      Not Listed For Sale

      557 Willard Rd Unit 5182, Hartford, VT 05059

      • 3 Beds
      • 2.5 Baths
      • 1,865 Sq Ft
      • Built 1976
      557 Willard Rd Unit 5182, Hartford, VT 05059

      Last Sold Summary

      • $282/SF
      • 4 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Derek Cosentino Four Seasons Sotheby's Int'l Realty

  • /31

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit B, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit B, Woodstock, VT 05091
  • /2

    $880,000 Sold Feb 12, 2026

    6 Ledgewood Rd Unit A1 w/ A2 Garage, Ludlow, VT 05149

    • 3 Beds
    • 3 Baths
    • 1,573 Sq Ft
    • Built 1991

    Last Sold Summary

    • 2% Above List Price
    • $559/SF
    • 0 Days On Market

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    6 Ledgewood Rd Unit A1 w/ A2 Garage, Ludlow, VT 05149
    • /39

      Est $395,629 Not Listed For Sale

      604 Mount View Loop, Rochester, VT 05767

      • 3 Beds
      • 2 Baths
      • 1,460 Sq Ft
      • Built 1990
      604 Mount View Loop, Rochester, VT 05767

      Last Sold Summary

      • 8% Above List Price
      • $250/SF
      • 7 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Nick Sicard EXP Realty

  • /38

    $795,000

    • 4 Beds
    • 3 Baths
    • 2,099 Sq Ft

    6077 Vt Route 12, Barnard, VT 05031

    BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

    David Donegan Snyder Donegan Real Estate Group

    6077 Vt Route 12, Barnard, VT 05031
  • /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 $532,452

    Last Listing Agent Dana Waters Dark Horse Realty

    77 Winding Rd, Brownsville, VT 05037
    • /16

      Not Listed For Sale

      1299 Quechee Main St, Hartford, VT 05001

      • 2 Beds
      • 1.5 Baths
      • 1,063 Sq Ft
      • Built 1978
      1299 Quechee Main St, Hartford, VT 05001

      Last Sold Summary

      • $268/SF
      • 13 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Linda Hicks Quechee Lakes Real Estate Center

  • /51

    $849,000

    • 3 Beds
    • 3.5 Baths
    • 2,992 Sq Ft

    235 Main St Unit 2, Norwich, VT 05055

    NORWICH GATEWAY - Welcome to townhome #2; spacious and modern within a coveted 5-unit community at the entrance to charming Norwich, VT. Lovingly maintained and move-in ready, this bright and cheery home offers an ideal blend of comfort, style, and convenience in one of the area’s most desirable locations. The thoughtfully designed three-level floor plan provides flexible living space, ideal for

    Tyler Hall BHHS Verani Upper Valley

    235 Main St Unit 2, Norwich, VT 05055
  • /20

    $145,000 Sold May 09, 2025

    14 Ridgeway St, Springfield, VT 05156

    • 3 Beds
    • 1 Bath
    • 1,277 Sq Ft
    • Built 1885

    Last Sold Summary

    • 19% Below List Price
    • $114/SF
    • 154 Days On Market

    Last Listing Agent Heather Gleim CENTURY 21 North East

    14 Ridgeway St, Springfield, VT 05156
    • /40

      Est $283,284 Not Listed For Sale

      4149 Vt Route 107, Stockbridge, VT 05772

      • 3 Beds
      • 1.5 Baths
      • 1,600 Sq Ft
      • Built 1900
      4149 Vt Route 107, Stockbridge, VT 05772

      Last Sold Summary

      • 3% Above List Price
      • $171/SF
      • 70 Days On Market

      Last Sold Price $274,000

      Last Listing Agent Flex Realty Group Flex Realty

  • /28

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit C, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit C, Woodstock, VT 05091
  • /10

    $176,560 Sold Jun 09, 2025

    39 Livery Stable Rd, Bethel, VT 05032

    • 2 Baths
    • 1,128 Sq Ft
    • Built 1900

    Last Sold Summary

    • 26% Below List Price
    • $157/SF
    • 225 Days On Market

    Current Estimated Value $189,086

    Last Listing Agent Jonathan Falby Green Light Real Estate

    39 Livery Stable Rd, Bethel, VT 05032
    • /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143

      Last Sold Summary

      • 1,909 Days On Market

      Last Sold Price $50,000

      Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

  • /15

    $237,000

    • Land
    • 226 Acres
    • $1,049 per Acre

    0 New Boston Rd, Thetford, VT 05074

    The land's primary feature is its nearly 1/2 mile of river frontage at its northern end. Two old woods trails head to the river providing good access to this scenic water resource. Given the land’s access, distance to electric power, Restricted Use Area, and opposing solar array, the highest and best use is likely a camp/seasonal home development, recreation, and/or forest management. A meadow at

    Thom Milke Fountains Land Inc.

    0 New Boston Rd, Thetford, VT 05074
  • /59

    $515,000 Sold Nov 06, 2025

    37 Breezy Hill Rd, Springfield, VT 05156

    • 5 Beds
    • 4.5 Baths
    • 4,244 Sq Ft
    • Built 1940

    Last Sold Summary

    • 26% Below List Price
    • $121/SF
    • 321 Days On Market

    Current Estimated Value $520,157

    Last Listing Agent Carol Cole BHG Masiello Brattleboro

    37 Breezy Hill Rd, Springfield, VT 05156
    • /29

      Not Listed For Sale

      140 Lodge Rd Unit 13-A, Ludlow, VT 05149

      • 2 Beds
      • 2.5 Baths
      • 1,248 Sq Ft
      • Built 2016
      140 Lodge Rd Unit 13-A, Ludlow, VT 05149

      Last Sold Summary

      • $541/SF
      • 30 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

  • /8

    $590,000

    • Land
    • 61.49 Acres
    • $9,595 per Acre

    0 Wild Apple Rd, Pomfret, VT 05067

    One of the most sought-after locations in the Woodstock area, this 61-acre property is accessed off of Wild Apple Road with a building site oriented to the south and east. At 1,600 feet in elevation, it enjoys sweeping views of Killington, Mount Ascutney, and the surrounding hills. The land offers complete privacy with a blend of woodlands, open fields, a stream, and a pond site. Bordering the

    Story Jenks LANDVEST

    0 Wild Apple Rd, Pomfret, VT 05067
  • /21

    $100,000 Sold Jul 24, 2025

    901 Giddings St, Springfield, VT 05150

    • 3 Beds
    • 1 Bath
    • 1,107 Sq Ft
    • Built 1940

    Last Sold Summary

    • 1% Above List Price
    • $90/SF
    • 61 Days On Market

    Last Listing Agent Amy Messina Town and Country Realty

    901 Giddings St, Springfield, VT 05150
    • /39

      Est $343,502 Not Listed For Sale

      32 Route 103 S Unit B-6, Ludlow, VT 05149

      • 3 Beds
      • 2 Baths
      • 1,116 Sq Ft
      • Built 1984
      32 Route 103 S Unit B-6, Ludlow, VT 05149

      Last Sold Summary

      • $309/SF
      • 148 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /10

    $799,000

    • Land
    • 52.3 Acres
    • $15,277 per Acre

    00 Granite Ledge, Pomfret, VT 05059

    Pristine land with views of Ascutney! Build your dream home on this unspoiled parcel in one of Pomfret's most beautifully preserved and scenic locales. Surrounded by large landholdings and conserved farmland, but only ten minutes from Woodstock and with excellent access to Route 4and Quechee, the land comprises historic rock walls, mature hardwoods, a stream, and offers the potential for pastoral

    Keri Cole Williamson Group Sotheby's International Realty

    00 Granite Ledge, Pomfret, VT 05059

Showing Results 121 - 160, Page 4 of 18

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