35,996

Windsor County, VT Homes

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  • /60

    $899,000

    • 6 Beds
    • 6 Baths
    • 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

    Kate Cassidy Four Seasons Sotheby's Int'l Realty

    31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
  • /40

    $40,000 per month

    • 3 Beds
    • 2.5 Baths
    • 4,007 Sq Ft
    • House for Rent

    975 S Hill Rd, Ludlow, VT 05149

    Come enjoy your ski season at this exceptional home located on prestigious South Hill. Pull right into the heated attached garage (no need for cleaning off the car on powder days!) then step into the big mudroom where you can store all of your gear, with washer/dryer and powder room. Now into the eat in kitchen with beautiful wood cabinetry and floors. The formal dining room is perfect for a nice

    Frank Provance Diamond Realty

    975 S Hill Rd, Ludlow, VT 05149
  • /41

    $330,000 Sold Oct 30, 2025

    • 1,798 Sq Ft
    • $184/SF
    • 94 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1880

    109 High St, Cavendish, VT 05142

    Upgraded, updated, and ready for you! Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated

    Dana Haley Diamond Realty

    109 High St, Cavendish, VT 05142
    • /17

      Est $85,708 Not Listed For Sale

      • 4 Beds

      35 Depot St, Chester, VT 05143

      35 Depot St, Chester, VT 05143
  • /46

    $825,000

    • 3 Beds
    • 3 Baths
    • 1,432 Sq Ft

    58 Greenbush Rd, Cavendish, VT 05142

    Charming Cape Cod Home in a Serene Country Setting – 10.10 AcresWelcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and

    Katie Ladue Gilbert KW Vermont Woodstock

    58 Greenbush Rd, Cavendish, VT 05142
  • /19

    $1,825 per month

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    2591 Johnson Hill Rd, South Royalton, VT 05068

    Settled on a peaceful stretch of Johnson Hill Road, this well-appointed 3-bedroom, 2-bath apartment at 2591 Johnson Hill Road, Royalton, VT offers comfortable, convenient living in a scenic Vermont setting. The home features an open, bright layout, ample parking (one spot in the garage, one in the driveway, with additional spaces likely available), and a pet-friendly policy (limit 1).Key

    2591 Johnson Hill Rd, South Royalton, VT 05068
  • /60

    $715,000 Sold Oct 30, 2025

    • 2,630 Sq Ft
    • $272/SF
    • 122 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1986

    2 Macdonald Ln, Ludlow, VT 05149

    Tucked away on a quiet dead-end dirt road off West Hill and only minutes to Okemo’s base lodge. This beautiful log cabin home on Okemo Mountain offers the perfect blend of rustic character and modern living. With 3 bedrooms, 3 bathrooms, and an open-concept layout, this is the Vermont retreat you've been waiting for. Step inside to a warm and inviting living room with vaulted ceilings, exposed

    Joseph Karl William Raveis Real Estate Vermont Properties

    2 Macdonald Ln, Ludlow, VT 05149
    • /6

      Est $73,572 Not Listed For Sale

      600 Kendricks Corner Rd, Perkinsville, VT 05151

      600 Kendricks Corner Rd, Perkinsville, VT 05151
  • /16

    $425,000

    • 6 Beds
    • 4 Baths
    • 2,243 Sq Ft

    3 MacE Hill Rd, Hartland, VT 05048

    Strong Cash Flow! Profitable Investment Opportunity! This fully leased three unit multifamily property is an excellent chance for investors to add a consistent cash flowing property to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. A low maintenance property with nice updates over the years which include separate electrical

    Alex DeFelice The Clerkin Agency, P.C.

    3 MacE Hill Rd, Hartland, VT 05048
  • /13

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    214 Main St, Cavendish, VT 05153

    NOT AVAILABLE UNTIL AUGUST 18, 2025. Fully furnished & outfitted, including kitchen pots/pans/plates/etc. Convection oven, microwave/hood fan over. Full sized fridge. Front loading W/D. Walkable to shopping, restaurant. 10 minutes to Okemo, 25 minutes to the Killington Skyeship. School right up the street, so no amount of snow will keep you from the Mountains! VAST trail right up the street too!

    Robert Balewicz Evergreen Realty of Vermont

    214 Main St, Cavendish, VT 05153
  • /41

    $90,000 Sold Oct 30, 2025

    • Land
    • 1.23 Acres
    • $73,171 per Acre
    • 149 Days On Market

    00 Snow Ln, Windsor, VT 05089

    Lovely residential neighborhood with easy access to I91. These two separate and contiguous building lots sit on a small private road and have town water and sewer access on the edge of the property. Power is also on-site. This listing is for 1.23 acres that are divided into two separate buildable lots of Parcel #2 which is .56 acres (MLS #5036196), and Parcel #3 which is .67 acres (MLS #5036198).

    John Bassette Bassette Real Estate Group

    00 Snow Ln, Windsor, VT 05089
    • /17

      Not Listed For Sale

      00 Hemlock Hill Dr, Ludlow, VT 05149

      00 Hemlock Hill Dr, Ludlow, VT 05149
  • /40

    $2,299,000

    • 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 the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

    John Wetmore Wetmore Real Estate

    5518 Vt Route 12, Barnard, VT 05031
  • /41

    $216,000 Sold Oct 29, 2025

    • 968 Sq Ft
    • $223/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1988

    133 Colonial Dr Unit 407, White River Junction, VT 05001

    Superb Location! Very nice 2 bedroom Wilder Townhouse / Condo unit located in the Oak Knoll Community. Being only minutes from the Dartmouth College campus, Dartmouth Hitchcock Medical Center and VA. Hospital make this property a prime investment opportunity! Featuring stylish black and stainless steel kitchen appliances with over the range microwave oven, dishwasher, glass cleantop oven range,

    Alex DeFelice The Clerkin Agency, P.C.

    133 Colonial Dr Unit 407, White River Junction, VT 05001
    • /4

      Est $203,000 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 579 Sq Ft

      16 Hemlock Ridge Dr Unit 308, White River Junction, VT 05001

      16 Hemlock Ridge Dr Unit 308, White River Junction, VT 05001
  • /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
  • /52

    $390,000 Sold Oct 29, 2025

    • 1,682 Sq Ft
    • $232/SF
    • 3 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2004

    2680 Hartford Ave Unit 15, White River Junction, VT 05001

    Welcome to Stony Creek, where style meets convenience. This freshly painted 2-bedroom, 2.5-bath condo offers an open, modern layout with thoughtful updates throughout. The kitchen features stainless steel appliances and granite countertops, flowing seamlessly into the dining and living areas. From the living room, step out onto your private deck overlooking wooded trails, perfect for morning

    Jaime Durell BHHS Verani Upper Valley

    2680 Hartford Ave Unit 15, White River Junction, VT 05001
    • /33

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,346 Sq Ft

      111 Lakeland Dr Unit B, Hartford, VT 05001

      111 Lakeland Dr Unit B, Hartford, VT 05001
  • /31

    $925,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,882 Sq Ft

    348 Laughlin Rd, Woodstock, VT 05091

    Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock location for those wanting a peaceful Vermont countryside vibe to unwind but the vibrant Woodstock Village life at the foot of your hill! The interior design presents a more refined open concept design that offers both openness but a

    Mary Mayhew Snyder Donegan Real Estate Group

    348 Laughlin Rd, Woodstock, VT 05091
  • /39

    $148,000 Sold Oct 29, 2025

    • 873 Sq Ft
    • $170/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    24 Fairground Heights, Springfield, VT 05156

    Cozy and Full of Potential! Tucked away in a quiet neighborhood yet close to all local amenities, this inviting home offers the ease of one-level living. With just a little finishing work, it can become the perfect retreat after a long day. Enjoy a spacious yard, a sunny setting, and the convenience of a one-car under garage. The home has already seen several updates, including a new kitchen,

    Carol Slocum Keller Williams Realty Metro-Keene

    24 Fairground Heights, Springfield, VT 05156
    • /34

      Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,790 Sq Ft

      13 Daybreak Dr Unit 301, Ludlow, VT 05149

      13 Daybreak Dr Unit 301, Ludlow, VT 05149
  • /54

    $1,150,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,424 Sq Ft

    2077 Sheddsville Rd, West Windsor, VT 05089

    GAMBOL HILL FARM - Located in the heart of West Windsor’s horse country, Gambol Hill Farm greets you with stone walls, mature trees, open fields and paddocks throughout the property. The beautiful post and beam home, set back off the road, stands tall among the mountain views in the background. The stone patio, complete with a vine covered arbor and edible grapes, looks out over beautiful gardens

    Dan Noble Snyder Donegan Real Estate Group

    2077 Sheddsville Rd, West Windsor, VT 05089
  • /36

    $103,000 Sold Oct 29, 2025

    • 1,376 Sq Ft
    • $75/SF
    • 40 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1965

    127 Fort Morrow Knoll, Stockbridge, VT 05772

    LOST VILLAGE LODGE – Exceptional property, location and privacy in central VT – with easy access from I 89 and Rte.100. Adirondack style log cabin with spectacular view that can be recovered. Situated in private development with private drive. Open, light and airy layout.; 2-bedroom cabin w/10 ft. tall Heatilator stone fireplace. Central heating, 2 woodstoves, skylights. 2 porches, deck, gardens.

    Patricia Harvey Xsell Realty LLC

    127 Fort Morrow Knoll, Stockbridge, VT 05772
    • /39

      Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,400 Sq Ft

      122 Parrish View Rd, West Windsor, VT 05037

      122 Parrish View Rd, West Windsor, VT 05037
  • /55

    $599,000 Under Contract

    • 1 Bed
    • 2 Baths
    • 1,384 Sq Ft

    578 E Barnard Rd, South Royalton, VT 05068

    This property is currently functioning as a very successful Airbnb and has bookings into November. The only date available for showings in the near future is September September 21st. Looking for something truly special? This unique modern home sits on over 10 acres in a peaceful, private setting with beautiful country views and unforgettable sunsets. Step inside the open-concept layout and enjoy

    Heather Morse Coldwell Banker Hickok and Boardman

    578 E Barnard Rd, South Royalton, VT 05068
  • /56

    $960,000 Sold Oct 29, 2025

    • 2,668 Sq Ft
    • $360/SF
    • 113 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1990

    32 Old Farm Rd, Norwich, VT 05055

    Spring is in full bloom around this beautiful home in the desirable Old Farm neighborhood! With many spaces thoughtfully renovated in recent years by Riverlight Builders, this property features a stunning new kitchen with a center island with bar seating, Quartzite natural stone countertops, and high-end cabinetry, seamlessly open to the main floor living areas, making it ideal for entertaining

    Evan Pierce Four Seasons Sotheby's Int'l Realty

    32 Old Farm Rd, Norwich, VT 05055
    • /39

      Est $669,190 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft

      28 Fowler Rd Unit N103, Ludlow, VT 05149

      28 Fowler Rd Unit N103, Ludlow, VT 05149
  • /43

    $2,600,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,998 Sq Ft

    2 Pleasant St, Woodstock, VT 05091

    2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern

    David Donegan Snyder Donegan Real Estate Group

    2 Pleasant St, Woodstock, VT 05091
  • /42

    $627,500 Sold Oct 28, 2025

    • 1,554 Sq Ft
    • $404/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    11 1/2 Church St Unit 4, Woodstock, VT 05091

    Downtown Woodstock Village – Perfectly situated in the heart of one of Vermont’s most picturesque towns, this stand-alone 2-bedroom, 2-bathroom cottage-style home offers both privacy and convenience. Part of a small, historic 4-unit condominium association, the property combines the character of the Village with the ease of shared ownership. An expansive lawn leads to frontage on the Ottauquechee

    Susan Hickey Snyder Donegan Real Estate Group

    11 1/2 Church St Unit 4, Woodstock, VT 05091
    • /28

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,170 Sq Ft

      238 South St, Hartford, VT 05088

      238 South St, Hartford, VT 05088
  • /60

    $729,000

    • 3 Beds
    • 2.5 Baths
    • 2,384 Sq Ft

    13 Stackpole Rd, Bethel, VT 05032

    Beautiful Contemporary Home on 5.25 acres Nestled just off the paved North Road, this stunning Contemporary residence offers a perfect blend of comfort, craftsmanship, and country charm. Set on 5.25 acres of open lawn and framed by stone walls and mature trees, the property provides a private, park-like setting ideal for relaxation and outdoor enjoyment. A welcoming covered front porch leads into

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    13 Stackpole Rd, Bethel, VT 05032
  • /22

    $299,000 Sold Oct 28, 2025

    • 2 Days On Market

    389 Smedley Rd, Royalton, VT 05068

    This beautiful 50-acre property is located at 389 Smedley Rd in Royalton, VT offers a blank canvas for your dream home or investment opportunity or turn key cabin get away ready for occupancy. The property was Perked and developed in 2025 with septic for a 4 bedroom home, Artesian well and electricity run to property and is classified as Land/Lot, providing endless possibilities for development.

    Derek Greene Derek Greene

    389 Smedley Rd, Royalton, VT 05068
    • /19

      Not Listed For Sale

      • 2 Beds
      • 3.5 Baths
      • 1,426 Sq Ft

      976 Hard Rd Unit 2, Hartford, VT 05001

      976 Hard Rd Unit 2, Hartford, VT 05001
  • /32

    $1,295,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    33 Mountain Ave, Woodstock, VT 05091

    Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one

    Mary Mayhew Snyder Donegan Real Estate Group

    33 Mountain Ave, Woodstock, VT 05091
  • /2

    $360,000 Sold Oct 28, 2025

    • 1,304 Sq Ft
    • $276/SF
    • 41 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1979

    231 Richardson Rd, Chester, VT 05143

    This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also

    Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson Rd, Chester, VT 05143
    • /40

      Est $677,479 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,434 Sq Ft

      621 Main St, Proctorsville, VT 05153

      621 Main St, Proctorsville, VT 05153
  • /34

    $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
  • /39

    $378,000 Sold Oct 28, 2025

    • 1,899 Sq Ft
    • $199/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    1577 Mount Hunger Rd, Bethel, VT 05032

    Enjoy the serenity of country living in this 1991 log home located in Barnard VT. that has the highly regarded Barnard Academy for elementary school and the Woodstock Union Schools for middle school and high school. The home features lots of country charm and is sited on 2.6 acres that includes a pond and lots of sunny areas for gardens . The lower walk out basement could be finished into more

    Carol Wood Williamson Group Sothebys Intl. Realty

    1577 Mount Hunger Rd, Bethel, VT 05032
    • /4

      Est $831,066 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft

      160 Solitude Rd Unit L104, Ludlow, VT 05149

      160 Solitude Rd Unit L104, Ludlow, VT 05149
  • /31

    $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

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