3,392

Homes in ZIP Code 05143

Section Image
  • 508 Mattson Rd, Chester, VT 05143
    508 Mattson Rd, Chester, VT 05143
    508 Mattson Rd, Chester, VT 05143
    /12

    $120,000

    • Land
    • 3.24 Acres
    • $37,037 per Acre

    508 Mattson Rd, Chester, VT 05143

    This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

    Jessica Citera Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • 870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, Chester, VT 05143
    /21

    $320,000

    Sold Dec 18, 2025

    870 Cummings Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 30 Days On Market

    Current Estimated Value $322,358

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
    • 42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      /40

      Est $361,347

      Not Listed For Sale

      42 Cobb Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,087 Sq Ft
      • Built 1965
      42 Cobb Rd, Chester, VT 05143

      Last Sold Summary

      • 39 Days On Market

  • 3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    /38

    $249,500

    • 4 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

    Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

    3668 Vt Route 103 N, Chester, VT 05143
  • 769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    /41

    $327,500

    Sold Aug 21, 2025

    769 Davidson Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $343,072

    Last Listing Agent Frank Provance Diamond Realty

    769 Davidson Hill Rd, Chester, VT 05143
    • 135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      /14

      Est $378,974

      Not Listed For Sale

      135 Lower Bartonsville Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 1977
      135 Lower Bartonsville Rd, Chester, VT 05143

      Last Sold Summary

      • 107 Days On Market

  • 3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    /47

    $549,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    3341 Trebo Rd, Chester, VT 05143

    Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a

    Daire Gibney Barrett and Valley Associates Inc.

    3341 Trebo Rd, Chester, VT 05143
  • 00 Hill Top Rd, Andover, VT 05143
    00 Hill Top Rd, Andover, VT 05143
    00 Hill Top Rd, Andover, VT 05143
    /21

    $105,000

    Sold Dec 19, 2025

    00 Hill Top Rd, Andover, VT 05143

    • Land
    • 13.34 Acres
    • $7,871 per Acre

    Last Sold Summary

    • 22% Below List Price
    • 275 Days On Market

    Last Listing Agent Flex Realty Group Flex Realty

    00 Hill Top Rd, Andover, VT 05143
    • 48 Valley Cemetery Rd, Athens, VT 05143
      48 Valley Cemetery Rd, Athens, VT 05143
      48 Valley Cemetery Rd, Athens, VT 05143
      /29

      Est $402,380

      Not Listed For Sale

      48 Valley Cemetery Rd, Athens, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,890 Sq Ft
      • Built 1999
      48 Valley Cemetery Rd, Athens, VT 05143

      Last Sold Summary

      • 163 Days On Market

  • 847 Simonsville Rd, Andover, VT 05143
    847 Simonsville Rd, Andover, VT 05143
    847 Simonsville Rd, Andover, VT 05143
    /38

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    847 Simonsville Rd, Andover, VT 05143

    Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

    Erin Kendall EXP Realty

    847 Simonsville Rd, Andover, VT 05143
  • 62 Circle Dr, Chester, VT 05143
    62 Circle Dr, Chester, VT 05143
    62 Circle Dr, Chester, VT 05143
    /37

    $389,000

    Sold Sep 22, 2025

    62 Circle Dr, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1945

    Last Sold Summary

    • $325/SF
    • 6 Days On Market

    Current Estimated Value $389,270

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • 126 Brookline Rd, Athens, VT 05143
      126 Brookline Rd, Athens, VT 05143
      126 Brookline Rd, Athens, VT 05143
      /28

      Est $397,480

      Not Listed For Sale

      126 Brookline Rd, Athens, VT 05143

      • 5 Beds
      • 3 Baths
      • 2,637 Sq Ft
      • Built 1900
      126 Brookline Rd, Athens, VT 05143

      Last Sold Summary

      • 26 Days On Market

  • 133 Baltimore Rd, North Springfield, VT 05150
    133 Baltimore Rd, North Springfield, VT 05150
    133 Baltimore Rd, North Springfield, VT 05150
    /53

    $525,000

    • 4 Beds
    • 2 Baths
    • 2,232 Sq Ft

    133 Baltimore Rd, North Springfield, VT 05150

    A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most

    Franchesca Collins Hall Collins Real Estate Group

    133 Baltimore Rd, North Springfield, VT 05150
  • 100 Stagecoach Rd, Town of Rockingham, VT 05156
    100 Stagecoach Rd, Town of Rockingham, VT 05156
    100 Stagecoach Rd, Town of Rockingham, VT 05156
    /18

    $180,000

    Sold Nov 07, 2025

    100 Stagecoach Rd, Town of Rockingham, VT 05156

    • Land
    • 32 Acres
    • $5,625 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 198 Days On Market

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    100 Stagecoach Rd, Town of Rockingham, VT 05156
    • 1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      /26

      Est $260,761

      Not Listed For Sale

      1096 Mattson Rd, Chester, VT 05143

      1096 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 23 Days On Market

  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /20

    $290,000

    $10K PRICE DROP
    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography.It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • 1295 Middletown Rd, Chester, VT 05143
    1295 Middletown Rd, Chester, VT 05143
    /2

    $792,000

    Sold Jul 15, 2025

    1295 Middletown Rd, Chester, VT 05143

    • 3 Beds
    • 3.5 Baths
    • 3,614 Sq Ft
    • Built 2012

    Last Sold Summary

    • 7% Below List Price
    • $219/SF
    • 0 Days On Market

    Current Estimated Value $773,345

    Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    1295 Middletown Rd, Chester, VT 05143
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $261,224

      Not Listed For Sale

      656 Depot St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,280 Sq Ft
      • Built 1987
      656 Depot St, Chester, VT 05143

      Last Sold Summary

      • 13 Days On Market

  • 3800 Weston-Andover Rd, Andover, VT 05143
    3800 Weston-Andover Rd, Andover, VT 05143
    3800 Weston-Andover Rd, Andover, VT 05143
    /41

    $5,150,000

    • 8 Beds
    • 7.5 Baths
    • 10,062 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • 725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    /2

    $800,000

    Sold Dec 12, 2025

    725 Flamstead Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,775 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $288/SF
    • 17 Days On Market

    Current Estimated Value $810,218

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

    725 Flamstead Rd, Chester, VT 05143
    • 566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      /53

      Est $554,934

      Not Listed For Sale

      566 Simonsville Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 1820
      566 Simonsville Rd, Chester, VT 05143

      Last Sold Summary

      • 229 Days On Market

  • 1359 Brockways Mills Rd, Rockingham, VT 05143
    1359 Brockways Mills Rd, Rockingham, VT 05143
    1359 Brockways Mills Rd, Rockingham, VT 05143
    /20

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft

    1359 Brockways Mills Rd, Rockingham, VT 05143

    Here is your chance to be a homeowner on 4.6 acres of your very own land. This sweet double wide built in 2000 will be easy to heat and maintain for the best of country living on a paved road. This home consists of 3 bedrooms, two baths. The living area is open and spacious with a large living room, dining room and a wonderful functional kitchen. The primary bedroom has its own bath for privacy.

    Monica Sumner BHG Masiello Brattleboro

    1359 Brockways Mills Rd, Rockingham, VT 05143
  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $210,000

    Sold May 13, 2026

    419 Coach Rd, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1968

    Last Sold Summary

    • 19% Below List Price
    • $146/SF
    • 252 Days On Market

    Last Listing Agent Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
    • 56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      /41

      Est $457,113

      Not Listed For Sale

      56 Hidden Newton Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,410 Sq Ft
      • Built 1999
      56 Hidden Newton Rd, Chester, VT 05143

      Last Sold Summary

      • 44 Days On Market

  • 1992 Andover Ridge Rd, Andover, VT 05143
    1992 Andover Ridge Rd, Andover, VT 05143
    1992 Andover Ridge Rd, Andover, VT 05143
    /35

    $380,000

    • Land
    • 24.5 Acres
    • $15,510 per Acre

    1992 Andover Ridge Rd, Andover, VT 05143

    Perched at the top of Andover Ridge Road, this exceptional Vermont building lot offers breathtaking 180-degree panoramic long-range views stretching across rolling mountain ranges and endless Green Mountain scenery. With a newly constructed driveway already in place and a state wastewater permit secured and the system installed, this property is well positioned for your future dream home or

    Claudia Harris Mary Mitchell Miller Real Estate

    1992 Andover Ridge Rd, Andover, VT 05143
  • 106 Hall Rd, Chester, VT 05143
    106 Hall Rd, Chester, VT 05143
    106 Hall Rd, Chester, VT 05143
    /27

    $210,000

    Sold Nov 20, 2025

    106 Hall Rd, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 528 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Below List Price
    • $398/SF
    • 33 Days On Market

    Current Estimated Value $209,775

    Last Listing Agent Sandy Reavill

    106 Hall Rd, Chester, VT 05143
    • 2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      /39

      Est $491,916

      Not Listed For Sale

      2358 N Hill Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,070 Sq Ft
      • Built 1975
      2358 N Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

  • 639 Main St, Weston, VT 05161
    639 Main St, Weston, VT 05161
    639 Main St, Weston, VT 05161
    /48

    $579,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,077 Sq Ft

    639 Main St, Weston, VT 05161

    639 Main Street, Weston, VermontOffered at $579,000A rare opportunity to own a turnkey home in the heart of picturesque Weston Village. Thisbeautifully renovated four-bedroom, two-bath residence offers the perfect blend of walkable villageliving, natural surroundings, and timeless Vermont charm.Built in 1952, this thoughtfully updated 2,077-square-foot home sits on 0.66 acres

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    639 Main St, Weston, VT 05161
  • 302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    /2

    $330,000

    Sold Nov 20, 2025

    302 Davidson Hill Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $367/SF
    • 114 Days On Market

    Current Estimated Value $331,817

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
    • 1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      /24

      Est $317,124

      Not Listed For Sale

      1767 Rockingham Rd, Chester, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 1,293 Sq Ft
      • Built 1988
      1767 Rockingham Rd, Chester, VT 05143

      Last Sold Summary

      • 116 Days On Market

  • 91 Vermont 35, Athens, VT 05143
    91 Vermont 35, Athens, VT 05143
    91 Vermont 35, Athens, VT 05143
    /53

    $200,000

    Pending
    • 384 Sq Ft

    91 Vermont 35, Athens, VT 05143

    A little piece of heaven awaits you at this charming camp set on 44 acres. The cabin sits high on a knoll overlooking a beautiful view of the expansive lower field and the distant hills. The wrap-around porch afford a birds-eye view of the changing seasons and the perfect perch to observe wildlife. The land – a great mix of fields, hills and woods – is an oasis for year-round outdoor recreation.

    Laura D'Angelo Berkley & Veller Greenwood Country

    91 Vermont 35, Athens, VT 05143
  • 1809 Marsh Hill Rd, Andover, VT 05143
    1809 Marsh Hill Rd, Andover, VT 05143
    1809 Marsh Hill Rd, Andover, VT 05143
    /28

    $450,000

    Sold Nov 14, 2025

    1809 Marsh Hill Rd, Andover, VT 05143

    • Land
    • 57.2 Acres
    • $7,867 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 73 Days On Market

    Current Estimated Value $449,035

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    1809 Marsh Hill Rd, Andover, VT 05143
    • 1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      /52

      Est $1,113,144

      Not Listed For Sale

      1328 Chandler Rd, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 3,779 Sq Ft
      • Built 1972
      1328 Chandler Rd, Chester, VT 05143

      Last Sold Summary

      • 220 Days On Market

  • 0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    /20

    $80,000

    Sold Dec 05, 2025

    0 Remington Rd Unit 5049898, Chester, VT 05143

    • Land
    • 1.82 Acres
    • $43,956 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 122 Days On Market

    Last Listing Agent Frank Provance Diamond Realty

    0 Remington Rd Unit 5049898, Chester, VT 05143
    • 218 Gunderson Rd, Chester, VT 05143
      218 Gunderson Rd, Chester, VT 05143
      218 Gunderson Rd, Chester, VT 05143
      /50

      Est $862,216

      Not Listed For Sale

      218 Gunderson Rd, Chester, VT 05143

      • 5 Beds
      • 2.5 Baths
      • 3,175 Sq Ft
      • Built 1907
      218 Gunderson Rd, Chester, VT 05143

      Last Sold Summary

      • 263 Days On Market

  • 1950 Anderson Rd, Chester, VT 05143
    1950 Anderson Rd, Chester, VT 05143
    1950 Anderson Rd, Chester, VT 05143
    /24

    $269,000

    Sold Dec 15, 2025

    1950 Anderson Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 876 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Above List Price
    • $307/SF
    • 5 Days On Market

    Last Listing Agent Wilma Skovinski Berkley & Veller Greenwood Country

    1950 Anderson Rd, Chester, VT 05143
    • 2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      /38

      Est $723,000

      Not Listed For Sale

      2401 N Hill Rd, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 1990
      2401 N Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 67 Days On Market

  • 534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    /58

    $550,000

    Sold Apr 02, 2026

    534 Elm St, Chester, VT 05143

    • 3,850 Sq Ft
    • Built 1868

    Last Sold Summary

    • 8% Below List Price
    • $143/SF
    • 154 Days On Market

    Current Estimated Value $562,761

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
    • 126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      /25

      Est $386,498

      Not Listed For Sale

      126 Gould Rd, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,714 Sq Ft
      • Built 1827
      126 Gould Rd, Chester, VT 05143

      Last Sold Summary

      • 12 Days On Market

  • 611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    /32

    $1,510,000

    Sold Dec 22, 2025

    611 Simmons Rd, Chester, VT 05143

    • 2 Beds
    • 4 Baths
    • 3,514 Sq Ft
    • Built 1965

    Last Sold Summary

    • 33% Below List Price
    • $430/SF
    • 151 Days On Market

    Current Estimated Value $1,536,480

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143

Showing Results 161 - 200, Page 5 of 18

Vermont Windsor County Chester 05143

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