Windsor County, VT Homes

• 

  

  

  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
• 

  

  

  /21

  $1,400 - $1,650 per month

  120 Main St.

  2 - 3 Beds

  120 Main St, Springfield, VT 05156

  120 Main St, Springfield, VT 05156
• 

  

  

  /53

  $66,000 Sold Aug 05, 2025

  517-519 Jackson Gore Rd Unit 517-519 QTR I, Ludlow, VT 05149

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

  Last Sold Summary

  • 1% Below List Price
  • $69/SF
  • 53 Days On Market

  Last Listing Agent Frank Provance Diamond Realty

  517-519 Jackson Gore Rd Unit 517-519 QTR I, Ludlow, VT 05149
• 

  

  

  /38

  Est $531,126 Not Listed For Sale

  3033 Vt Route 14, South Royalton, VT 05068

  • 4 Beds
  • 2 Baths
  • 2,412 Sq Ft
  • Built 1999

  3033 Vt Route 14, South Royalton, VT 05068

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 6 Days On Market

  Last Sold Price $489,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
• 

  

  

  /33

  $499,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,085 Sq Ft

  192 Cross St, White River Junction, VT 05001

  Ideally located in the village of Quechee and just minutes from Woodstock and the heart of the Upper Valley, this well-maintained Colonial at 192 Cross Street offers comfortable living in one of the region’s most desirable settings. Set on a pleasant 0.35 acre lot in a welcoming neighborhood, the home provides a thoughtful floor plan with bright, inviting spaces throughout. The main level offers

  

  Lori Shipulski

  BHHS Verani Upper Valley

  (802) 214-7312

  192 Cross St, White River Junction, VT 05001
• 

  

  /29

  $13,000 per month

  • 4 Beds
  • 4 Baths
  • 4,400 Sq Ft
  • House for Rent

  36 Moses Pond Rd, Weston, VT 05161

  No need to ski out west this ski season because WE have all of the snow here on the east with an impressive snow base and seemingly endless supply heading our way this season!It's time to indulge yourself with this truly unique custom log, masterfully crafted timber peg construction mecca of mountain luxury at its finest. The views are incredible; the amenities are top shelf. The screened in

  Peggy O'neill Cummings & Co

  36 Moses Pond Rd, Weston, VT 05161
• 

  

  /53

  $798,000 Sold Oct 31, 2025

  392 Gully Rd, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • $610/SF
  • 28 Days On Market

  Current Estimated Value $793,685

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  392 Gully Rd, Woodstock, VT 05091
• 

  

  /30

  Est $456,344 Not Listed For Sale

  6293 Route 106, Reading, VT 05062

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1989

  6293 Route 106, Reading, VT 05062

  Last Sold Summary

  • 13% Above List Price
  • $325/SF
  • 5 Days On Market

  Last Sold Price $405,000

  Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties
• 

  

  /60

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft

  29 Summer Hill St, Springfield, VT 05156

  Delightful home located in a desirable residential area of town. This home is located right across from one of the town parks/playgrounds. Enjoy this light filled 2 story home featuring hardwood and tile floors on the first floor and warm and comfortable carpet on second floor bedrooms. A gas fireplace in the living room for the cool winter days will help to keep you cozy. Kitchen is nicely set

  

  Julie Buffum

  Buffum Realty

  (802) 520-2696

  29 Summer Hill St, Springfield, VT 05156
• 

  

  /6

  $1,125 per month

  30 Main St

  1 Bed

  30 Main St, Springfield, VT 05156

  30 Main St, Springfield, VT 05156
• 

  /2

  $30,000 Sold Jun 04, 2025

  206 Cummings Rd, Chester, VT 05143

  • Land
  • 0.5 Acre
  • $60,000 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 208 Days On Market

  Current Estimated Value $32,990

  Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  206 Cummings Rd, Chester, VT 05143
• 

  

  /54

  Est $380,890 Not Listed For Sale

  1 Okemo Heights, Ludlow, VT 05149

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 1966

  1 Okemo Heights, Ludlow, VT 05149

  Last Sold Summary

  • 2% Above List Price
  • $361/SF
  • 10 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Frank Provance Diamond Realty
• 

  

  /30

  $449,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 2,365 Sq Ft

  16 Sterling Springs Dr, White River Junction, VT 05001

  Perched at the very top of the prestigious Sterling Springs development, this stately residence offers the rare combination of privacy, presence, and panoramic views. This home offers an elevated setting, with lovely views and a serene backdrop that make every sunrise and sunset feel extraordinary. With generous living spaces filled with natural light, this home offers the perfect atmosphere for

  

  Jeff Fogg

  Black House Real Estate

  (802) 500-7779

  16 Sterling Springs Dr, White River Junction, VT 05001
• 

  

  /15

  $20,000 per month

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

  145 Main St Unit 216, Ludlow, VT 05149

  Welcome to Okemo! This very nicely updated and conveniently located condo sits in the center of town in the iconic Mill Building. This open concept condo has two bedrooms with full sized beds and several options for extra sleeping arrangements for guests to include a trundle bed, a chair with a twin sized convertible bed and a sofa that sleeps an additional two people comfortably. You can't beat

  Peggy O'neill Cummings & Co

  145 Main St Unit 216, Ludlow, VT 05149
• 

  

  /60

  $625,000 Sold Sep 11, 2025

  200 Peregrine Rd, Plymouth, VT 05056

  • 4 Beds
  • 4 Baths
  • 2,818 Sq Ft
  • Built 1995

  Last Sold Summary

  • 11% Below List Price
  • $222/SF
  • 108 Days On Market

  Current Estimated Value $713,133

  Last Listing Agent Marni Rieger KW Vermont-Killington

  200 Peregrine Rd, Plymouth, VT 05056
• 

  

  /48

  Est $292,015 Not Listed For Sale

  36 Evarts Rd, North Hartland, VT 05052

  • 3 Beds
  • 1 Bath
  • 1,369 Sq Ft
  • Built 1946

  36 Evarts Rd, North Hartland, VT 05052

  Last Sold Summary

  • 8% Above List Price
  • $197/SF
  • 147 Days On Market

  Last Sold Price $269,444

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

  

  /38

  $329,000

  • 2 Beds
  • 3.5 Baths
  • 1,984 Sq Ft

  974 Hard Rd Unit D6, Hartford, VT 05001

  This 2BR, 3.5BA end unit condo offers fantastic meadow views from the back deck, living room and dining room. Located in a private, quiet and serene country setting yet within close proximity to all Quechee Club and Upper Valley amenities. The condo has been lovingly cared for and updated throughout. It offers ample size with three separate levels of living space. Upstairs are two good size

  

  Herb Hart

  Quechee Lakes Real Estate Center

  (802) 392-0255

  974 Hard Rd Unit D6, Hartford, VT 05001
• 

  

  /17

  $1,290 - $2,185 per month

  Apartment for Rent

  Studio

  241 S Main St, White River Junction, VT 05001

  Studio's available in downtown White River Junction, walking distance to most amenities!

  241 S Main St, White River Junction, VT 05001
• 

  

  /60

  $997,500 Sold Nov 14, 2025

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142

  • 4 Beds
  • 4.5 Baths
  • 4,420 Sq Ft
  • Built 1834

  Last Sold Summary

  • 19% Below List Price
  • $226/SF
  • 109 Days On Market

  Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142
• 

  

  /41

  Est $359,174 Not Listed For Sale

  948 High St, Cavendish, VT 05142

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1973

  948 High St, Cavendish, VT 05142

  Last Sold Summary

  • 4% Below List Price
  • $235/SF
  • 142 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Ann Jacques Century 21 Highview Realty
• 

  

  /30

  $519,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,669 Sq Ft

  10 Vermont Dr, White River Junction, VT 05001

  Designed for easy one-level living, this wonderful home combines functionality with a tranquil setting, all within a desirable neighborhood. If you’re seeking privacy, convenience, and low-maintenance comfort, this gem is ready to welcome you home. Inside, you’ll find a bright, open-concept layout enhanced by vaulted ceilings and abundant natural light. The spacious living and dining areas flow

  

  Jeff Fogg

  Black House Real Estate

  (802) 880-8374

  10 Vermont Dr, White River Junction, VT 05001
• 

  /2

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  32 S Main St Unit 7, Chester, VT 05143

  Traditional two bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site.$1,400.00 per month with heat included. No pets.References and credit check required.

  Team BVA Rentals Barrett and Valley Associates Inc.

  32 S Main St Unit 7, Chester, VT 05143
• 

  

  /60

  $475,000 Sold Aug 27, 2025

  472 Main St, Chester, VT 05143

  • 5 Beds
  • 7 Baths
  • 5,546 Sq Ft
  • Built 1850

  Last Sold Summary

  • 5% Below List Price
  • $86/SF
  • 36 Days On Market

  Current Estimated Value $475,414

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  472 Main St, Chester, VT 05143
• 

  

  /43

  Est $1,416,560 Not Listed For Sale

  2373 Lime Pond Rd, South Royalton, VT 05068

  • 5 Beds
  • 3.5 Baths
  • 3,679 Sq Ft
  • Built 1832

  2373 Lime Pond Rd, South Royalton, VT 05068

  Last Sold Summary

  • 9% Above List Price
  • $353/SF
  • 121 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Dan Noble Snyder Donegan Real Estate Group
• 

  

  /58

  $1,400,000

  • 6 Beds
  • 5 Baths
  • 4,571 Sq Ft

  505 Deweys Mills Rd, Hartford, VT 05047

  The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

  

  Jennifer Falvey

  KW Vermont Woodstock

  (877) 419-4767

  505 Deweys Mills Rd, Hartford, VT 05047
• 

  /2

  $1,525 per month

  27 Maple Street

  2 Beds

  27 Maple St, Windsor, VT 05089

  27 Maple St, Windsor, VT 05089
• 

  

  /36

  $655,000 Sold Nov 24, 2025

  4 Stanton St, Woodstock, VT 05091

  • 4 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 1901

  Last Sold Summary

  • 18% Above List Price
  • $308/SF
  • 7 Days On Market

  Current Estimated Value $623,018

  Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  4 Stanton St, Woodstock, VT 05091
• 

  

  /39

  Est $410,728 Not Listed For Sale

  2240 Baltimore Rd, Chester, VT 05143

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft
  • Built 1986

  2240 Baltimore Rd, Chester, VT 05143

  Last Sold Summary

  • 7% Above List Price
  • $254/SF
  • 14 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Morriah Adams BHG Masiello Brattleboro
• 

  

  /33

  $729,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,609 Sq Ft

  215 Granite Way Unit 8B, Quechee, VT 05059

  Immaculate 4BR, 3.5BA end unit condo with a detached one car garage. Located at the very end of a private, quiet neighborhood yet within walking distance to the Quechee Village, post office and covered bridge. This condo is being sold fully furnished and in move in ready condition. Some of the many wonderful interior features include: hardwood floors, granite countertops, central A/C, new stove

  

  Herb Hart

  Quechee Lakes Real Estate Center

  (802) 204-5986

  215 Granite Way Unit 8B, Quechee, VT 05059
• 

  

  /15

  $2,800 per month

  • 5 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • House for Rent

  686 S Windsor St, Royalton, VT 05068

  Property Id: 2002289This freshly painted single-family home is move-in ready and ideally located just 0.5 miles from Vermont Law School. Featuring a split-level layout, it offers a main floor with three handicap-accessible bedrooms, an open kitchen, dining area, and living room—plus direct access to a private deck, perfect for outdoor dining or relaxation.The finished basement

  686 S Windsor St, Royalton, VT 05068
• 

  

  /23

  $255,000 Sold Jul 01, 2025

  59 Weston Heights, Windsor, VT 05089

  • 4 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1942

  Last Sold Summary

  • $253/SF
  • 90 Days On Market

  Current Estimated Value $269,556

  Last Listing Agent Don Chabot Town and Country Realty

  59 Weston Heights, Windsor, VT 05089
• 

  

  /25

  Not Listed For Sale

  130 E Fisher Rd, Hartford, VT 05001

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1975

  130 E Fisher Rd, Hartford, VT 05001

  Last Sold Summary

  • $210/SF
  • 150 Days On Market

  Last Sold Price $512,000

  Last Listing Agent Heather Ashline BHHS Verani Upper Valley
• 

  

  /4

  $160,000

  • Land
  • 6 Acres
  • $26,667 per Acre

  1901 Royalton Hill Rd, South Royalton, VT 05068

  Great opportunity to turn this private lot into your dream Vermont retreat. Just 10 minutes from the highway. Current owner has started some clearing and land prep.

  

  Steve Swanson

  EXP Realty

  (802) 215-3062

  1901 Royalton Hill Rd, South Royalton, VT 05068
• 

  

  /20

  $2,750 per month

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Condo for Rent

  50 Pleasant St Unit Apartment 1, Ludlow, VT 05149

  Property Id: 1266254 Bedroom 3Bath fully furnished 1st floor apartment. .This is a unique property unlike any other.Walk to Ludlow shops and restaurants.Furnished with antique furniture.SORRY NO PETS OR SMOKING ALLOWEDThis is a spring and summer vacation rental.

  50 Pleasant St Unit Apartment 1, Ludlow, VT 05149
• 

  

  /31

  $450,000 Sold Oct 06, 2025

  151 Burton Rd, Weston, VT 05161

  • 4 Beds
  • 2 Baths
  • 1,715 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $262/SF
  • 71 Days On Market

  Current Estimated Value $464,153

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

  151 Burton Rd, Weston, VT 05161
• 

  

  /27

  Not Listed For Sale

  350 Mountain Rd Unit 207, Ludlow, VT 05149

  • 1 Bed
  • 1 Bath
  • 698 Sq Ft
  • Built 1984

  350 Mountain Rd Unit 207, Ludlow, VT 05149

  Last Sold Summary

  • $482/SF
  • 21 Days On Market

  Last Sold Price $336,500

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

  

  /40

  $369,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  1846 Dartt Hill Rd, Bethel, VT 05032

  1978 Saltbox on 10 acres of both open and wooded land. The home boasts wide plank floors throughout with 3 bedrooms, 2 baths, open floor plan on the main floor with spacious kitchen. A lovely home, a must see.

  

  Sherri McPhetres

  Vermont Heritage Real Estate

  (802) 424-9553

  1846 Dartt Hill Rd, Bethel, VT 05032
• 

  

  /20

  $1,875 per month

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

  50 Pleasant St Unit 2, Ludlow, VT 05149

  Property Id: 1266323 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
• 

  

  /35

  $400,000 Sold Jun 12, 2025

  562 Quechee West Hartford Rd, Hartford, VT 05001

  • 2 Beds
  • 1 Bath
  • 1,632 Sq Ft
  • Built 1967

  Last Sold Summary

  • 11% Above List Price
  • $245/SF
  • 4 Days On Market

  Last Listing Agent Jeff Fogg Black House Real Estate

  562 Quechee West Hartford Rd, Hartford, VT 05001
• 

  

  /60

  Est $813,991 Not Listed For Sale

  451 Colby Pond Rd, Plymouth, VT 05149

  • 3 Beds
  • 4 Baths
  • 3,691 Sq Ft
  • Built 1994

  451 Colby Pond Rd, Plymouth, VT 05149

  Last Sold Summary

  • 2% Above List Price
  • $215/SF
  • 135 Days On Market

  Last Sold Price $795,000

  Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

Showing Results 41 - 80, Page 2 of 18