35,113

Windsor, VT Homes

Section Image
  • /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 Ski Country Real Estate

    745 Vermont Route 100 Unit A3, Bridgewater, VT 05035
    • /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
  • /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 located

    Laura Derderian Killington Valley Real Estate

    7137 Us Route 4, Bridgewater, VT 05034
  • /29

    $205,000 Sold May 23, 2025

    • 1,664 Sq Ft
    • $123/SF
    • 142 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1954

    38 Bailey St, Springfield, VT 05156

    Lovingly maintained 3-bed, 1-bath cape-style home situated on a quiet street in downtown Springfield. Features a dry stone retaining wall around perimeter with terraced area, eat-in kitchen, large living area with views of Mt Ephraim, 31' x 11' rec room, and workshop in basement. Within walking distance to Springfield Cinemas, Edgar May Recreation Center, Vermont Beer Makers, Springfield

    Luke Sykes Jim Campbell Real Estate

    38 Bailey St, Springfield, VT 05156
    • /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143
  • /42

    $1,175,000

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

    1847 Trebo Rd, Chester, VT 05143

    With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful and uniquely situated on 20 acres of gorgeous green lawn, fields, forest, extensive stone walls; a mere 2 miles to Chester. Since 2020 the house has been transformed and restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel Solar Array,

    David White OwnerEntry.com

    1847 Trebo Rd, Chester, VT 05143
  • /41

    $460,000 Sold May 23, 2025

    • 2,178 Sq Ft
    • $211/SF
    • 281 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1890

    39 High St, Ludlow, VT 05149

    Ludlow Village home with views of Okemo Mountain. This five-bedroom farmhouse, perfectly situated on High Street, is in the heart of Ludlow Village. Step inside from the covered porch to the large mudroom, which is ideal for storing your seasonal gear. Off the mudroom, you’ll find two bedrooms and a full bathroom. Next, the living room with a wood-burning fireplace, ideal for winter gatherings.

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    39 High St, Ludlow, VT 05149
    • /22

      Not Listed For Sale

      00 Advent Hill Rd, Hartland, VT 05048

      00 Advent Hill Rd, Hartland, VT 05048
  • /21

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,391 Sq Ft

    205 Channing Dr, Windsor, VT 05089

    Welcome to this inviting 2-bedroom, 1.5-bath ranch-style home located just a short distance from Main Street in Windsor, VT. Set on a manageable and sunny .29-acre lot, this home offers convenient single-level living with a bright, open-concept kitchen and living area—perfect for relaxing or entertaining. A spacious back enclosed porch extends your living space, ideal for enjoying Vermont’s

    Katie Ladue Gilbert KW Vermont Woodstock

    205 Channing Dr, Windsor, VT 05089
  • /38

    $495,000 Sold May 23, 2025

    • Land
    • 74 Acres
    • $6,671 per Acre
    • 481 Days On Market

    0 MacGinnis Unit 4982154, Ludlow, VT 05149

    The Soapstone Babbling Brook flows through this wonderful property with stone walls, soft and hard wood trees, all within 1.5 miles to downtown Ludlow and Okemo Mountain. Developers take notice of the beautiful long distant VIEWS to OKEMO and beyond from several different locations on the property, with the potential to connect to village sewer. The perfect playground for any outdoor

    Frank Provance Diamond Realty

    0 MacGinnis Unit 4982154, Ludlow, VT 05149
    • /32

      Est $86,265 Not Listed For Sale

      42 Advent Hill Rd, Hartland, VT 05048

      42 Advent Hill Rd, Hartland, VT 05048
  • /24

    $800,000

    • 2 Beds
    • 1 Bath
    • 679 Sq Ft

    38 Northshore Dr, Ludlow, VT 05149

    Same family owned for several decades and now it's time for another family to see the benefits of lakeside living. This cottage is located on private Northshore Drive on beautiful Lake Rescue. Use as-is for summer fun, then plan your future new build or winterize this home. Expand the existing footprint to suit your family's needs. The waterfront gazebo and storage building is your access to

    Katherine Burns William Raveis Real Estate Vermont Properties

    38 Northshore Dr, Ludlow, VT 05149
  • /28

    $195,000 Sold May 22, 2025

    • 1,568 Sq Ft
    • $124/SF
    • 34 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    119 Old Tavern Rd, Weston, VT 05161

    Tucked back on a peaceful 3.5 acres surrounded by trees, just .5 miles from the Weston Fields.This unit offers great space with a high ceilings, a laundry room, separate dining area, two bedrooms with large closets and a primary bedroom with a large closet and private bath. A gas stove warms the living area on the cooler days. A slider walk out to the back deck where you can enjoy the quiet

    Jessica Citera Cummings & Co

    119 Old Tavern Rd, Weston, VT 05161
    • /15

      Est $218,878 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,090 Sq Ft

      1295 Hartford Ave Unit 2, White River Junction, VT 05001

      1295 Hartford Ave Unit 2, White River Junction, VT 05001
  • /34

    $374,000

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft

    724 S Windsor St, South Royalton, VT 05068

    This lovely updated three-bedroom two bath Central VT home offers great opportunity for residential use, or for investors as a rental property. At one time a two-unit, the home is less than a mile to Vermont Law School (VLS), and just a half mile to the WRV elementary and High Schools. The lovely Village green, where Community activities and farmers markets are held throughout the year is also

    Kate Jarvis Williamson Group Sothebys Intl. Realty

    724 S Windsor St, South Royalton, VT 05068
  • /32

    $780,000 Sold May 22, 2025

    • 2,280 Sq Ft
    • $342/SF
    • 98 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1973

    149 Upper Crossroad, Ludlow, VT 05149

    Location, Location, Location! Walk to the Okemo Base Lodge from this clean and tidy side-by-side duplex. Each townhouse has 3 bedrooms, 2 baths, an open kitchen/dining/living room and laundry included in each residence.. The lower levels each have a comfortable den, bath and bedroom, while the upper levels both have 2 additional bedrooms, a 2nd bath, laundry, and living area along with propane

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

    149 Upper Crossroad, Ludlow, VT 05149
    • /40

      Est $576,797 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,604 Sq Ft

      263 Sparrow Hawk Rd, Rochester, VT 05767

      263 Sparrow Hawk Rd, Rochester, VT 05767
  • /34

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 1,799 Sq Ft

    1221 Baker Turn Rd Unit 1F, Hartford, VT 05059

    Located at the summit of Quechee’s ski hill, this stunning 3 bedroom / 3 bath Kingswood I condo is practically brand new after a just completed dramatic renovation. Updates include new doors, windows, electrical, heating and air conditioning, new modern kitchen with stainless steel appliances, three completely renovated bathrooms, new flooring throughout the 3 levels of living space, new lighting

    Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

    1221 Baker Turn Rd Unit 1F, Hartford, VT 05059
  • /8

    $455,000 Sold May 22, 2025

    • 1,952 Sq Ft
    • $233/SF
    • 59 Days On Market
    • 5 Beds
    • 1.5 Baths
    • Built 1840

    400 Dutton District Rd, Springfield, VT 05156

    For generations, this farm has been a productive part of the Springfield agricultural scene for many years. Seller has continued the tradition of supplying poultry, eggs and meat to the local markets around central Vermont. Large barn currently used for vehicle storage but can hold animals as well. Work shops, storage sheds and a pasture pole barn make the possibilities abound!

    Judy Thompson Walnut Hill Realty

    400 Dutton District Rd, Springfield, VT 05156
    • /37

      Est $2,069,920 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 5,985 Sq Ft

      529 Kerwin Hill Rd, Norwich, VT 05055

      529 Kerwin Hill Rd, Norwich, VT 05055
  • /34

    $299,000

    • 5 Beds
    • 2 Baths
    • 2,560 Sq Ft

    630 Vermont 14, Bethel, VT 05032

    630/642 on VT Route 14 in East Bethel Village are two homes on one deeded parcel consisting of 1.2 +/- acres. The main home is a large New Englander style house with 3 bedrooms and updated bathroom. Above, and with a separate entrance, you will find an apartment with 2 bedrooms and a full bath. The main home and the apartment have been rentals in the past and could be again with a little TLC.

    Eric Kenyon Rural Vermont Real Estate

    630 Vermont 14, Bethel, VT 05032
  • /43

    $420,419 Sold May 21, 2025

    • 1,728 Sq Ft
    • $243/SF
    • 62 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1930

    1883 Plains Rd, Perkinsville, VT 05151

    Spring is a time for change and this could be your time to live in Vermont with your own farm. Put the chicken coop to use and supply your neighbors with eggs. Start your garden plants in the greenhouse and can your veggies to enjoy all Winter. Keep it simple or go big and build a barn.The 25.3 acres is comprised of two lots. Carve out some walking and snowshoeing trails and breathe the fresh

    Tyleen Murray Kelley Real Estate, Inc.

    1883 Plains Rd, Perkinsville, VT 05151
    • /35

      Est $436,912 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,832 Sq Ft

      473 Taylor Dr, Windsor, VT 05089

      473 Taylor Dr, Windsor, VT 05089
  • /55

    $2,950,000

    • 4 Beds
    • 4.5 Baths
    • 6,548 Sq Ft

    657 Town Farm Rd, Ludlow, VT 05149

    61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen with wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

    Andre Menard Mary W. Davis Realtor & Assoc., Inc.

    657 Town Farm Rd, Ludlow, VT 05149
  • /10

    $13,500 Sold May 20, 2025

    • Land
    • 2.10 Acres
    • $6,429 per Acre
    • 41 Days On Market

    0 Route 107 Unit 5032274, Stockbridge, VT 05772

    An affordable 2 acre parcel of land with 248 foot frontage on a paved State of Vermont maintained year round road. The topography of the parcel makes it best suited for recreational use or for camping. The Town of Stockbridge is home to numerous vacation homes oriented towards skiing at well known Killington. Shopping, casual dining, recreation opportunities and scenic Vermont Route 100 are all

    John Wetmore Wetmore Real Estate

    0 Route 107 Unit 5032274, Stockbridge, VT 05772
    • /8

      Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 2,562 Sq Ft

      397 N Windsor St, South Royalton, VT 05068

      397 N Windsor St, South Royalton, VT 05068
  • /40

    $385,000

    • 4 Beds
    • 1.5 Baths
    • 1,792 Sq Ft

    94 Perley Farm Rd, South Royalton, VT 05068

    Step into a unique piece of Vermont history with this beautifully converted brick schoolhouse, now a warm and inviting 4-bedroom, 1.5-bath home. Perfectly blending classic charm with modern comforts, this one-of-a-kind property offers character, space, and serenity in a picturesque setting.From the moment you arrive, the handsome brick exterior and original architectural details set the tone.

    Holly Hall Hall Collins Real Estate Group

    94 Perley Farm Rd, South Royalton, VT 05068
  • /25

    $395,900 Sold May 20, 2025

    • 1,574 Sq Ft
    • $252/SF
    • 33 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1992

    133 White Oak Ln, Bethel, VT 05032

    Set back on 5.4 private acres in prime Central Vermont, this perfectly maintained 3-bedroom cape cod style home, constructed in 1992, is the one you have been looking for! The property is located 6.4 miles to downtown South Royalton and the Vermont Law School. It is 30 miles from Killington Ski area, and 2 miles from downtown Bethel VT. The lot backs up to the VAST trail system. The house

    Jonathan Falby Vermont Heritage Real Estate

    133 White Oak Ln, Bethel, VT 05032
    • /40

      Not Listed For Sale

      • 6 Beds
      • 9 Baths
      • 9,621 Sq Ft

      249 Bragg Hill Rd, Norwich, VT 05055

      249 Bragg Hill Rd, Norwich, VT 05055
  • /55

    $1,189,000

    • 5 Beds
    • 4 Baths
    • 3,282 Sq Ft

    1873 North Rd, Bethel, VT 05032

    On the west-facing ridge of Barnard, Vermont’s fabled North Road, this ca. 1982 Cape enjoys panoramic long-range views of the Green Mountain Range to the west and North. With ten acres of fenced open pasture and a wood lot, a large, detached barn, and plenty of land to use, the property offers a range of possibilities. Expanded and improved by the current owners over the last 20 years, the house

    Richard Higgerson Higgerson & Company

    1873 North Rd, Bethel, VT 05032
  • /31

    $469,000 Sold May 19, 2025

    • 880 Sq Ft
    • $533/SF
    • 6 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1936

    446 New Boston Rd, Norwich, VT 05055

    Charming & energy efficient 2-Bedroom bungalow nestled in a peaceful country setting located just minutes from downtown. This unique, cozy home includes built-in shelves, drawers and cabinets in every room. It has been updated with a newer septic & drilled well, recent bathroom renovation, a mini-split heat pump, heat pump hot water heater and many more too numerous to note, along with an

    Carol Robert Housing Solutions Real Estate LLC

    446 New Boston Rd, Norwich, VT 05055
    • /8

      Est $573,952 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,662 Sq Ft

      314 Newton Ln, White River Junction, VT 05001

      314 Newton Ln, White River Junction, VT 05001
  • /25

    $289,900

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft

    1471 County Rd, Windsor, VT 05089

    Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as

    Jenn Boyer Coldwell Banker Homes Unlimited

    1471 County Rd, Windsor, VT 05089
  • /35

    $302,000 Sold May 19, 2025

    • 1,824 Sq Ft
    • $166/SF
    • 20 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    74 Mountains Edge Rd Unit 403, Brownsville, VT 05037

    Beautiful ski in/ski out condo with breathtaking views in the highly desirable 400 building.Discover the perfect blend of comfort, style, and adventure in this beautifully updated condo—offering the best views in the entire complex. Overlooking thousands of acres of pristine Town and State forest, this home provides direct access to the renowned Ascutney Trails, ideal for biking, skiing, and

    Shawna Fox KW Vermont Woodstock

    74 Mountains Edge Rd Unit 403, Brownsville, VT 05037
    • /29

      Est $355,484 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,517 Sq Ft

      3 Old Mill Pond Rd, Windsor, VT 05089

      3 Old Mill Pond Rd, Windsor, VT 05089
  • /16

    $399,000

    • Land
    • 13 Acres
    • $29,776 per Acre

    00 N Hill Pent Rd, Ludlow, VT 05149

    Opportunity awaits with these two connected wooded building lots totaling 13.44 acres, offering easy access to the VAST snowmobile trail network. Located on a quiet, dead-end country road, this peaceful setting is ideal for those seeking a private getaway with four-season recreational opportunities right at your doorstep. Lot A is 4.67 acres and lot B is 8.77 acres. Both parcels include

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 N Hill Pent Rd, Ludlow, VT 05149
  • /22

    $680,000 Sold May 19, 2025

    • 2,800 Sq Ft
    • $243/SF
    • 66 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1979

    138 Tilden Hill Rd, Norwich, VT 05055

    Great opportunity for a spacious home in Norwich, VT! Just minutes from Dartmouth, yet offering privacy and the potential for stunning mountain views, this home features four bedrooms in the main living area, plus a one-bedroom in-law suite with an office in the finished walkout basement. With abundant living space and natural light throughout, this home is ready for buyers to personalize and

    Jenna Luce RE/MAX Upper Valley

    138 Tilden Hill Rd, Norwich, VT 05055
    • /29

      Est $614,195 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,105 Sq Ft

      104 Stage Rd, South Pomfret, VT 05067

      104 Stage Rd, South Pomfret, VT 05067
  • /36

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,452 Sq Ft

    358 Us Route 5 S, Windsor, VT 05089

    Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

    Daniel Preston KW Vermont Woodstock

    358 Us Route 5 S, Windsor, VT 05089
  • /60

    $400,000 Sold May 19, 2025

    • 2,960 Sq Ft
    • $135/SF
    • 166 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1844

    196 North St, Chester, VT 05143

    The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a

    Geralyn Donohue Engel & Völkers Okemo

    196 North St, Chester, VT 05143

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