34,496

Windsor County, VT Homes

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  • /30

    $385,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    3051 Vt Rt 107, Stockbridge, VT 05772

    A rare chance to own a substantial slice of Vermont's countryside, with commercial upside built in. This 62-acre property spans both sides of VT Route 107, offering a diverse landscape along with the flexibility of a commercial zoning designation, opening the door to a range of business and development possibilities. On the south side, mature forested acreage includes a former sugarbush offering

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    3051 Vt Rt 107, Stockbridge, VT 05772
  • /20

    $2,300 Per Month

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

    50 Pleasant St Unit 2, Ludlow, VT 05149

    Property Id: 126632 3 Bedroom 2 Bath 2nd floor Apartment. Very bright and open. New dishwasher, washer and dryer. Fully furnished. Close to shopping and restaurants. On the shuttle route. Okemo base 2 miles away.

    50 Pleasant St Unit 2, Ludlow, VT 05149
  • /41

    $315,000

    Sold Nov 21, 2025

    1 Dorrance St, Windsor, VT 05089

    • 2 Beds
    • 1.5 Baths
    • 1,649 Sq Ft
    • Built 1945

    Last Sold Summary

    • 4% Below List Price
    • $191/SF
    • 7 Days On Market

    Current Estimated Value $307,266

    Last Listing Agent Evan Russell Real Broker LLC

    1 Dorrance St, Windsor, VT 05089
    • /29

      Not Listed For Sale

      383 Old Quechee Rd Unit 8C, Hartford, VT 05001

      • 2 Beds
      • 2.5 Baths
      • 1,063 Sq Ft
      • Built 1978
      383 Old Quechee Rd Unit 8C, Hartford, VT 05001

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  • /39

    $850,000

    • 4 Beds
    • 2 Baths
    • 2,352 Sq Ft

    208 Jarvis Rd, Perkinsville, VT 05151

    Delayed showings until 8/16. Motivated Seller! This exceptional four-bedroom home encompasses 11.5 pristine acres. The residence features light-filled, elegantly scaled principal rooms optimized for entertaining and daily living. There is a study/bedroom on the first floor with a three-quarter hall bath next to it. Upstairs, there are three bedrooms (one is being used as a study) and a generously

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    208 Jarvis Rd, Perkinsville, VT 05151
  • /17

    $2,550 - $2,650

    Total Monthly Price

    • 2 - 3 Beds
    • 1 Bath
    • 1,275 Sq Ft
    • Condo for Rent

    2460 US Route 5 N, Windsor, VT 05089

    Duplex set back from road on Route 5, Windsor, VT. Town of Windsor, stores, restaurants, post office, rec center, bank within walking distance/short drive. Easy commute to Interstate 91.

    2460 US Route 5 N, Windsor, VT 05089
  • /3

    $245,000

    Sold Nov 14, 2025

    574 Willard Rd Unit 1A, Quechee, VT 05059

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $278/SF
    • 97 Days On Market

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

    574 Willard Rd Unit 1A, Quechee, VT 05059
    • /26

      Not Listed For Sale

      11A Prospect St, Woodstock, VT 05091

      • 2 Beds
      • 1.5 Baths
      • 930 Sq Ft
      • Built 1860
      11A Prospect St, Woodstock, VT 05091

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /50

    $499,900

    • 4 Beds
    • 2 Baths
    • 2,259 Sq Ft

    50 Linhale Rd, Springfield, VT 05156

    On a quiet dead-end road in Springfield, Vermont, this classic 1935 Cape Cod sits on 5.5 private, rolling acres that have been lovingly shaped over many years into a true country haven. Mature landscaping, established garden beds, a functional greenhouse for year-round growing, a barn, stables, and open fields ready for pasture or cultivation all speak to a deep appreciation for the land and

    Agent Photo

    Vin Morris

    BHHS Verani Upper Valley

    50 Linhale Rd, Springfield, VT 05156
  • /17

    $3,100

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,330 Sq Ft
    • House for Rent

    930 New Boston Rd, Norwich, VT 05055

    3-bedroom raised ranch with dinning room, living area with wood stove and newly renovated open kitchen with new appliances, mud room, basement and a little cabin in the back with screened in porch overlooking the pond. Largest bedroom can accommodate a king bed. Second room will accommodate a queen size bed. One bedroom is small, but will accommodates plenty of room with a twin or full

    930 New Boston Rd, Norwich, VT 05055
  • /11

    $33,000

    Sold Dec 18, 2025

    25 Maxfield Ln, Hartland, VT 05001

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1987

    Last Sold Summary

    • 33% Below List Price
    • $29/SF
    • 5 Days On Market

    Last Listing Agent Charlene Gaudette Coldwell Banker LIFESTYLES - Hanover

    25 Maxfield Ln, Hartland, VT 05001
    • /47

      Not Listed For Sale

      647 Bugbee St Unit 7, White River Junction, VT 05001

      • 2 Beds
      • 1 Bath
      • 928 Sq Ft
      • Built 1987
      647 Bugbee St Unit 7, White River Junction, VT 05001

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Dorothy Griswold The Clerkin Agency, P.C.

  • /60

    $475,000

    $20K PRICE DROP
    • 3,036 Sq Ft

    7868 Pomfret Rd, North Pomfret, VT 05053

    CASH FLOW POSITIVE - GREAT VALUE! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space,

    Agent Photo

    John Bassette

    Bassette Real Estate Group

    7868 Pomfret Rd, North Pomfret, VT 05053
  • /17

    $3,000

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    96 S Main St, Chester, VT 05143

    Spacious 4-Bedroom Home with Large Backyard in the Heart of Chester, VT.Welcome to 96 S Main St — a charming and well-appointed 4-bedroom, 2.5-bath home offering 2,215 square feet of comfortable living space in the very heart of Chester village.Inside, you’ll find a bright and generous living room and dining room perfect for relaxing or entertaining, a functional kitchen with all

    96 S Main St, Chester, VT 05143
  • /41

    $240,000

    Sold Oct 07, 2025

    15 Gill Terrace, Ludlow, VT 05149

    • 4 Beds
    • 1.5 Baths
    • 2,640 Sq Ft
    • Built 1955

    Last Sold Summary

    • 40% Below List Price
    • $91/SF
    • 388 Days On Market

    Current Estimated Value $356,289

    Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

    15 Gill Terrace, Ludlow, VT 05149
    • /32

      Est $547,915

      Not Listed For Sale

      19 White Loop Unit A103, Ludlow, VT 05149

      • 2 Beds
      • 2 Baths
      • 1,044 Sq Ft
      • Built 1986
      19 White Loop Unit A103, Ludlow, VT 05149

      Last Sold Summary

      • 145 Days On Market

      Last Listing Agent Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  • /2

    $129,000

    $10K PRICE DROP
    • 2,144 Sq Ft

    73 Union St, Springfield, VT 05156

    Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

    Agent Photo

    Julie Buffum

    Buffum Realty

    73 Union St, Springfield, VT 05156
  • /30

    $2,150

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,064 Sq Ft
    • Condo for Rent

    4 Pine Brook Ln Unit Pine Brook B4, North Springfield, VT 05150

    Clean, safe, quiet unit. Two-story condo (2 bed, 1.5 bath, 1,050 sqft) in N Springfield’s peaceful Pine Brook Village. Front door is ground level, steps from 2 parking spots. Downstairs has a full kitchen (brand new fridge and DW), dining area, half bathroom, large living room, covered back porch and stone patio. Upstairs has a washer/dryer, full bathroom, large

    4 Pine Brook Ln Unit Pine Brook B4, North Springfield, VT 05150
  • /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 $489,856

    Last Listing Agent John Bassette Bassette Real Estate Group

    973 Route 106, Reading, VT 05062
    • /40

      Est $2,614,393

      Not Listed For Sale

      739 Westerdale Rd, Woodstock, VT 05091

      • 4 Beds
      • 4.5 Baths
      • 5,017 Sq Ft
      • Built 2003
      739 Westerdale Rd, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /47

    $1,595,000

    $300K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,708 Sq Ft

    196 Cowdrey Outlook, Bethel, VT 05032

    For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    196 Cowdrey Outlook, Bethel, VT 05032
  • /17

    $2,550 - $2,650

    Total Monthly Price

    • 2 - 3 Beds
    • 1 Bath
    • 1,275 Sq Ft
    • Condo for Rent

    2460 US Route 5 N, Windsor, VT 05089

    Duplex set back from road on Route 5, Windsor, VT. Town of Windsor, stores, restaurants, post office, rec center, bank within walking distance/short drive. Easy commute to Interstate 91.

    2460 US Route 5 N, Windsor, VT 05089
  • /43

    $76,000

    Sold Jun 18, 2026

    211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $98/SF
    • 70 Days On Market

    Last Listing Agent Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149
    • /57

      Est $2,290,079

      Not Listed For Sale

      126 Route 66, Ludlow, VT 05149

      • 6 Beds
      • 4 Baths
      • 4,301 Sq Ft
      • Built 1971
      126 Route 66, Ludlow, VT 05149

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  • /52

    $579,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 3,428 Sq Ft

    583 Hawk Spur Rd, Plymouth, VT 05056

    Looking for a property with HUGE equity possibilities?? Your dream mountain retreat perfectly nestled between Okemo/Vail and Killington awaits! This contemporary diamond in the rough boasts mountain views and sits on a double lot in the desirable Hawk resort area. You will fall in love with the floods of natural light that bring the outdoors in. This home is ready for your ideas and finishes

    Agent Photo

    Lisa Kelley

    Cummings & Co

    583 Hawk Spur Rd, Plymouth, VT 05056
  • /42

    $1,950

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft
    • Condo for Rent

    2046 Hartford Ave Unit 4, Hartford, VT 05001

    This two-story, pet friendly two bedroom/one bath apartment puts you right near everything the Upper Valley has to offer. Enjoy easy access to local pubs and restaurants, nearby fitness centers, shopping centers, and more everything you need within minutes.Commuting is a breeze:5 minutes (0.2 mi) to Downtown White River Junction10 minutes (3.6 mi) to the West Lebanon

    2046 Hartford Ave Unit 4, Hartford, VT 05001
  • /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 $1,649,473

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    441 Spruce Way, Woodstock, VT 05091
    • /27

      Est $189,426

      Not Listed For Sale

      1838 Brown Schoolhouse Rd, Reading, VT 05062

      • 2 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1979
      1838 Brown Schoolhouse Rd, Reading, VT 05062

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Chelsea Bevis KW Vermont Woodstock

  • /43

    $699,000

    • 2 Beds
    • 3 Baths
    • 1,364 Sq Ft

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149

    Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

    Agent Photo

    John Napier

    TPW Real Estate

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149
  • /22

    $2,397

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 930 Sq Ft
    • Condo for Rent

    1856 Quechee Main St Unit 9, Hartford, VT 05001

    Prime Location in the village of Quechee3 bedrooms (2 Bedrooms plus a loft bedroom on second level), 2 full baths2 building next to Simon Pierce. Red Barn.Parking lot is the Quechee Green, you can just walk. Also there's private parking too. Plenty of parking no limit on cars. Two deck with beautiful view of Quechee Ski Resort and river. The third level loft is

    1856 Quechee Main St Unit 9, Hartford, VT 05001
  • /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 $200,508

    Last Listing Agent Betsy Adamovich Real Broker LLC

    37 Coolidge Rd, Springfield, VT 05156
    • /56

      Est $3,684,191

      Not Listed For Sale

      284 Amsden Rd, Barnard, VT 05031

      • 4 Beds
      • 2.5 Baths
      • 3,782 Sq Ft
      • Built 1991
      284 Amsden Rd, Barnard, VT 05031

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /34

    $385,000

    Under Contract
    • Land
    • 62 Acres
    • $6,210 per Acre

    3051 Vt Rte 107, Stockbridge, VT 05772

    A rare chance to own a substantial slice of Vermont's countryside, with commercial upside built in. This 62-acre property spans both sides of VT Route 107, offering a diverse landscape along with the flexibility of a commercial zoning designation, opening the door to a range of business and development possibilities. On the south side, mature forested acreage includes a former sugarbush offering

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    3051 Vt Rte 107, Stockbridge, VT 05772
  • /25

    $2,050

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    244 Vermont Route 132 Unit 1, Sharon, VT 05065

    244 Vermont Route 132 Unit 1, Sharon, VT 05065
  • /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 $500,133

    Last Listing Agent Betty McEnaney Diamond Realty

    56 Main St, Ludlow, VT 05149
    • /60

      Not Listed For Sale

      82 Button Hook Ln, Barnard, VT 05031

      • 4 Beds
      • 2 Baths
      • 2,915 Sq Ft
      • Built 1989
      82 Button Hook Ln, Barnard, VT 05031

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Eric Johnston Four Seasons Sotheby's Int'l Realty

  • /39

    $949,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,183 Sq Ft

    63 Royall Tyler Rd, Hartford, VT 05001

    Settle into the farmers porch with a morning coffee and watch the seasons change across the Vermont hills. Inside, every detail speaks to quality craftsmanship — thoughtful appointments, warm finishes, and a layout designed for real family life. The yard has plenty of room for kids to run, explore, and make the kind of memories that bring families back to Vermont generation after

    Agent Photo

    Herb Hart

    Quechee Lakes Real Estate Center

    63 Royall Tyler Rd, Hartford, VT 05001
  • /26

    $2,000 Per Month

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    44 Butternut Ln Unit 1, Wood Stock, VT 05091

    Enjoy the charm of village living in this beautifully furnished second-floor apartment located in a historic home in the heart of Taftsville, Vermont a hamlet of Woodstock. This bright and inviting apartment offers four spacious rooms, large windows, hard wood floors, a cozy pellet stove (pellets included), and a dedicated full-size office, making it ideal for remote professionals or anyone

    Matt DePrizio Covered Bridge RE

    44 Butternut Ln Unit 1, Wood Stock, VT 05091
  • /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
    • /44

      Est $1,776,093

      Not Listed For Sale

      2090 Randall Rd, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 2,423 Sq Ft
      • Built 2007
      2090 Randall Rd, Woodstock, VT 05091

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

Showing Results 81 - 120, Page 3 of 18

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