Windsor County, VT Homes

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  /2

  $54,900

  Pending

  • Land
  • 3 Acres
  • $18,300 per Acre

  00 Comstock Ave, Weathersfield, VT 05030

  3.00 +/- lot located just minutes from I91, Claremont, Windsor, Springfield and the upper valley. If you have been looking for an untouched piece of land this is your opportunity.

  

  Julie Buffum

  Buffum Realty

  00 Comstock Ave, Weathersfield, VT 05030
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  /20

  $3,000 Per Month

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

  50 Pleasant St Unit Apartment 1, Ludlow, VT 05149

  Property Id: 126625 4 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 ALLOWED This is a Family sized ski vacation rental.

  50 Pleasant St Unit Apartment 1, 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
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  /29

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,203 Sq Ft

  42 Mark St, Springfield, VT 05156

  Delightful cape style home in a family friendly neighborhood. Large lot with detached single car garage, additional building for storage, lots of level space for a garden or to fence in. Home features a covered entry. This home has seen lots of updates thru its life including a newer roof, new wooden siding that has been freshly painted, interior of the home has also been freshly painted. Lots of

  

  Julie Buffum

  Buffum Realty

  42 Mark St, Springfield, VT 05156
• 

  

  /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
• 

  

  /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
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  /43

  $419,900

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,982 Sq Ft

  176 Meadow Rd, Chester, VT 05143

  Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless

  

  Lauren Behm

  Berkshire Hathaway HomeServices Stratton Home

  176 Meadow Rd, Chester, VT 05143
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  /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
• 

  

  /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
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  /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.
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  /43

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,489 Sq Ft

  32 Mark St, Springfield, VT 05156

  More photos are coming! This home has been loved and cared for 50 plus years by the same family and now it is ready for a new chapter. Located in a nice family friendly neighborhood that is perfect for evening strolls around the block. Home features newer windows, hardwood floors, a heated sunroom, and a large dining room. The living room flows nicely into the heated sunroom for lots of

  

  Julie Buffum

  Buffum Realty

  32 Mark St, 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
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  /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
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  /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.
• 

  

  /17

  $75,000

  • 2 Beds
  • 1 Bath
  • 620 Sq Ft

  1144 Potash Brook Rd, Chester, VT 05143

  Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

  

  Julie Buffum

  Buffum Realty

  1144 Potash Brook Rd, Chester, VT 05143
• 

  

  /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
• 

  

  /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
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  /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
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  /12

  $149,000

  • Land
  • 17.7 Acres
  • $8,418 per Acre

  0 Trebo Rd, Chester, VT 05143

  Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

  

  Gail Beardmore

  Engel & Völkers Okemo

  0 Trebo Rd, Chester, VT 05143
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  /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
• 

  

  /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
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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

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  3051 Vt Rt 107, Stockbridge, VT 05772
• 

  

  /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
• 

  

  /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
• 

  

  /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

  

  Jennifer Falvey

  KW Vermont Woodstock

  208 Jarvis Rd, Perkinsville, VT 05151
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  /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
• 

  

  /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
• 

  

  /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

  

  Vin Morris

  BHHS Verani Upper Valley

  50 Linhale Rd, Springfield, VT 05156
• 

  

  /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
• 

  

  /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
• 

  

  /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,

  

  John Bassette

  Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
• 

  

  /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