34,496

Windsor County, VT Homes

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  • /58

    $450,000

    $25K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, Chester, VT 05143
  • /18

    $2,850 Per Month

    • 2 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    1856 Quechee Main St, Quechee, VT 05059

    2-bedroom, 3-bathroom condo located in the picturesque Quechee, VT. This property boasts a bonus loft room, perfect for a home office or additional living space. The location is unbeatable, with easy access to I-89, making commuting a breeze. Plus, the condo is just a short walk away from a beautiful park, offering a perfect blend of convenience and outdoor enjoyment.

    1856 Quechee Main St, Quechee, VT 05059
  • /60

    $524,900

    Sold Oct 20, 2025

    41 Woodlawn Dr, White River Junction, VT 05001

    • 2 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • Built 1985

    Last Sold Summary

    • $175/SF
    • 5 Days On Market

    Current Estimated Value $537,182

    Last Listing Agent Alex DeFelice The Clerkin Agency, P.C.

    41 Woodlawn Dr, White River Junction, VT 05001
    • /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

      • 6 Days On Market

      Last Listing Agent Karen DeMas Four Seasons Sotheby's Int'l 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
  • /18

    $2,800 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    69 Belknap Ln, Windsor, VT 05089

    Welcome to this warm and inviting fully furnished 3-bedroom, 1-bath home that blends rustic charm with modern comfort. The spacious open-concept kitchen and dining area features beautiful wood accents, generous cabinet storage, and a functional layout ideal for both everyday living and entertaining. The living room offers a bright and comfortable space filled with natural light—perfect for

    69 Belknap Ln, Windsor, VT 05089
  • /38

    $299,000

    Sold Jun 03, 2026

    1658 Route 100 N, Ludlow, VT 05149

    • 3 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1964

    Last Sold Summary

    • $340/SF
    • 20 Days On Market

    Current Estimated Value $294,480

    Last Listing Agent Tucker Adirondack Lange Lange & Lange

    1658 Route 100 N, Ludlow, VT 05149
    • /35

      Not Listed For Sale

      41 Parkhurst Unit L1, Cavendish, VT 05153

      • 2 Beds
      • 2.5 Baths
      • 1,445 Sq Ft
      • Built 2005
      41 Parkhurst Unit L1, Cavendish, VT 05153

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  • /60

    $469,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,676 Sq Ft

    64 Maple St, Chester, VT 05143

    Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

    Betsy Adamovich Real Broker LLC

    64 Maple St, Chester, VT 05143
  • /25

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,142 Sq Ft
    • House for Rent

    1193 Prosper Rd, Woodstock, VT 05091

    3 bedroom, 2 bathroom home in Woodstock, Vermont, featuring an open-concept layout, hardwood floors throughout, and abundant natural light. Set on 4 acres that offer privacy and a connection to nature, the property includes a chicken coop and raised garden beds for easy homesteading. Trails are nearby and skiing is close by, while Central Street is a short distance away for dining and shopping.

    1193 Prosper Rd, Woodstock, VT 05091
  • /39

    $360,000

    Sold Oct 20, 2025

    123 Commonwealth Ave, Springfield, VT 05156

    • 3 Beds
    • 2 Baths
    • 2,113 Sq Ft
    • Built 1945

    Last Sold Summary

    • 12% Below List Price
    • $170/SF
    • 258 Days On Market

    Current Estimated Value $362,617

    Last Listing Agent Brian Whipple Coldwell Banker Homes Unlimited

    123 Commonwealth Ave, Springfield, VT 05156
    • /4

      Not Listed For Sale

      1599 Mattson Rd, Chester, VT 05143

      1599 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Amy Vashaw Twin State Realty LLC

  • /33

    $1,895,000

    • 2 Beds
    • 2.5 Baths
    • 2,944 Sq Ft

    2394 Fletcher Hill Rd, Woodstock, VT 05091

    Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

    John Snyder Snyder Donegan Real Estate Group

    2394 Fletcher Hill Rd, Woodstock, VT 05091
  • /2

    $1,425 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    114-114 State St Unit 114A, Windsor, VT 05089

    This charming 1-bedroom home is located on the first floor of a 4-unit building and includes convenient in-unit washer and dryer hookups. Enter the unit through the rear of the building, where you'll enjoy a beautiful water view right outside your back door and porch. The kitchen is equipped with a stove/oven, refrigerator, and ample space for meal preparation. Conveniently located across

    114-114 State St Unit 114A, Windsor, VT 05089
  • /52

    $355,000

    Sold Sep 30, 2025

    643 Main St, Cavendish, VT 05153

    • 5,984 Sq Ft
    • Built 1820

    Last Sold Summary

    • 15% Below List Price
    • $59/SF
    • 60 Days On Market

    Current Estimated Value $376,994

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    643 Main St, Cavendish, VT 05153
    • /48

      Est $1,102,759

      Not Listed For Sale

      5274 W Woodstock Rd, Woodstock, VT 05091

      • 2 Beds
      • 2 Baths
      • 2,058 Sq Ft
      • Built 1972
      5274 W Woodstock Rd, Woodstock, VT 05091

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /60

    $849,000

    $100K PRICE DROP Under Contract
    • 5,497 Sq Ft

    31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

    Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity! In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic New

    Kate Cassidy Four Seasons Sotheby's Int'l Realty

    31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
  • /33

    $3,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Condo for Rent

    873 Bragg Hill Rd Unit 2, Norwich, VT 05055

    This furnished 3-bedroom, 2-bathroom house situated on 12 private acres with panoramic 360° views is available immediately for lease up to 6 months, and possibility of extending into house-sharing arrangement when owner returns in spring/summer. This has an open concept living, new floors, fully equipped kitchen (with dishwasher/trash compactor), fireplace, indoor SAUNA, brand new washer/dryer,

    873 Bragg Hill Rd Unit 2, Norwich, VT 05055
  • /46

    $810,000

    Sold Aug 29, 2025

    122 Coachmans Way, Hartford, VT 05001

    • 3 Beds
    • 2.5 Baths
    • 2,852 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $284/SF
    • 8 Days On Market

    Current Estimated Value $814,219

    Last Listing Agent Evan Pierce Four Seasons Sotheby's Int'l Realty

    122 Coachmans Way, Hartford, VT 05001
    • /40

      Not Listed For Sale

      87 Robbins Hill, Hartford, VT 05059

      • 3 Beds
      • 2 Baths
      • 2,078 Sq Ft
      • Built 1978
      87 Robbins Hill, Hartford, VT 05059

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  • /31

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,385 Sq Ft

    26 Mount Peg Rd Unit D, 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 D, Woodstock, VT 05091
  • /11

    $2,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,210 Sq Ft
    • Condo for Rent

    123 Brookside Dr Unit 1, Hartford, VT 05001

    White River Junction - 2 Bed, 2 Bath Duple - $2250 plus utilities Available 10/09/20267/212-bedroom, 2 full bathroom duplex with modern laminate flooring in living areas and carpeted bedrooms. The ground floor has plenty of natural light coming from large living room windows and a sliding door leading to a private deck. In addition, the ground floor features a conveniently located

    123 Brookside Dr Unit 1, Hartford, VT 05001
  • /51

    $1,225,000

    Sold May 15, 2026

    593 Red Barn Rd, White River Junction, VT 05001

    • 5 Beds
    • 4.5 Baths
    • 3,060 Sq Ft
    • Built 1975

    Last Sold Summary

    • 28% Below List Price
    • $400/SF
    • 206 Days On Market

    Current Estimated Value $1,281,523

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    593 Red Barn Rd, White River Junction, VT 05001
    • /26

      Not Listed For Sale

      976 Hard Rd Unit C3, Hartford, VT 05001

      • 3 Beds
      • 3.5 Baths
      • 1,426 Sq Ft
      • Built 1972
      976 Hard Rd Unit C3, Hartford, VT 05001

      Last Sold Summary

      • 137 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /60

    $2,200,000

    $295K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 7,322 Sq Ft

    1497 Bowman Rd, Barnard, VT 05068

    Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

    Richard Higgerson Higgerson & Company

    1497 Bowman Rd, Barnard, VT 05068
  • /17

    $3,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,083 Sq Ft
    • Condo for Rent

    383 Old Quechee Rd, Quechee, VT 05059

    Summer Vacation Rental!! Fully furnished & fully stocked condo in Quechee Vermont. 2 bedroom, 2.5 bathroom with private balcony. Open concept living/dining/kitchen, laundry in unit, primary bedroom with ensuite bath. This condo is available June, July and August OR September through May 2027. Tenant will pay heat and electricity for longer term lease. Short drive to I89, Dartmouth College and

    383 Old Quechee Rd, Quechee, VT 05059
  • /34

    $570,000

    Sold Jan 09, 2026

    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • Built 1983

    Last Sold Summary

    • 2% Below List Price
    • $274/SF
    • 5 Days On Market

    Last Listing Agent Linda Hicks Quechee Lakes Real Estate Center

    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001
    • /15

      Est $60,160

      Not Listed For Sale

      3438 Royalton Turnpike, Barnard, VT 05068

      3438 Royalton Turnpike, Barnard, VT 05068

      Last Sold Summary

      • 168 Days On Market

      Last Listing Agent Kate Cassidy Four Seasons Sotheby's Int'l Realty

  • /57

    $1,450,000

    • 3 Beds
    • 3 Baths
    • 1,836 Sq Ft

    144 Lodge Rd Unit 1, Ludlow, VT 05149

    Welcome to South Face Village! True slopeside living at its best. This front-row, ski-in/ski-out 3-bedroom, 3-bath condo is literally on the slope. Walk out your front door, plop your skis or board down and head to the Sunshine lift. This gives you direct access to the South Face Express Quad. Inside this immaculate, turnkey unit is everything you'll want in your mountain château. Step in take

    Frank Provance Diamond Realty

    144 Lodge Rd Unit 1, Ludlow, VT 05149
  • /7

    $1,125 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    438 S Main St Unit 2, Bethel, VT 05032

    Welcome to this comfortable 1-bedroom, 1-bath apartment located in the charming town of Bethel, VT. This practical home offers a spacious eat-in kitchen with ample cabinet and counter space, along with an electric stove, refrigerator, and on-site laundry for added convenience.Heating Fuel, Hot Water, Water/Sewer, Trash, Snow Plowing, Lawncare are all included in the rent, making monthly

    438 S Main St Unit 2, Bethel, VT 05032
  • /13

    $115,000

    Sold Jun 24, 2026

    398 Valley View Rd, White River Junction, VT 05001

    • Land
    • 4.1 Acres
    • $28,049 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 49 Days On Market

    Current Estimated Value $368,667

    Last Listing Agent Grayson VanHendrick Flex Realty

    398 Valley View Rd, White River Junction, VT 05001
    • /41

      Not Listed For Sale

      54 E Fisher Rd, Hartford, VT 05001

      • 4 Beds
      • 2.5 Baths
      • 3,227 Sq Ft
      • Built 2003
      54 E Fisher Rd, Hartford, VT 05001

      Last Sold Summary

      • 131 Days On Market

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

  • /58

    $2,650,000

    $450K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,843 Sq Ft

    66 Hollow Farm Rd, Woodstock, VT 05071

    CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

    David Donegan Snyder Donegan Real Estate Group

    66 Hollow Farm Rd, Woodstock, VT 05071
  • /8

    $1,500 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    43 Connecticut River Rd Unit 1, Hartford, VT 05001

    White River Junction, VT 1 Bed, 1 Bath basement unit with an office $1500 includes heatAvailable 08/14/20261 Bedroom basement unit with an electric stove and refrigeratorTenant responsible for electric, supplemental electric heat for the bathroom and one of the bedrooms, cable and internet.Landlord responsible for oil heat, trash removal, lawn care and plowing of the

    43 Connecticut River Rd Unit 1, Hartford, VT 05001
  • /17

    $40,000

    Sold Oct 06, 2025

    138 Ascutney St, Windsor, VT 05089

    • 2 Beds
    • 1 Bath
    • 434 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Above List Price
    • $92/SF
    • 6 Days On Market

    Last Listing Agent DJ Chabot Town and Country Realty

    138 Ascutney St, Windsor, VT 05089
    • /30

      Est $284,333

      Not Listed For Sale

      169 Woodhaven Dr Unit 2B, White River Junction, VT 05001

      • 2 Beds
      • 1.5 Baths
      • 1,048 Sq Ft
      • Built 1985
      169 Woodhaven Dr Unit 2B, White River Junction, VT 05001

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /60

    $2,195,000

    $255K PRICE DROP Pending
    • 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
  • /28

    $2,125 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,048 Sq Ft
    • House for Rent

    189 Woodhaven Dr, Hartford, VT 05001

    Norwich, VT 2 Bedroom Condo $2150 plus utilities / Pets allowedAvailable 08/25/2026This 2 bedrooms 1 1/2-bathroom condominium is located just 5 minutes from Dartmouth College and 15 minutes from Dartmouth Hitchcock Memorial Hospital in the well-established and quiet Woodhaven Condominium Community. Cozy and comfortable floor plan, and includes electric range, fridge, and

    189 Woodhaven Dr, Hartford, VT 05001
  • /30

    $325,000

    Sold May 20, 2026

    30 Meadow Dr, Springfield, VT 05156

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Above List Price
    • $203/SF
    • 7 Days On Market

    Current Estimated Value $320,283

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    30 Meadow Dr, Springfield, VT 05156
    • /22

      Not Listed For Sale

      574 Willard Rd Unit 2C, Hartford, VT 05001

      • 2 Beds
      • 1 Bath
      • 832 Sq Ft
      • Built 1978
      574 Willard Rd Unit 2C, Hartford, VT 05001

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Sandy Reavill

Showing Results 201 - 240, Page 6 of 18

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