3,152

Middlebury, VT Homes

Section Image
    • 26 Gorham Ln, Middlebury, VT 05753
      26 Gorham Ln, Middlebury, VT 05753
      26 Gorham Ln, Middlebury, VT 05753
      /20

      Est $442,975

      Not Listed For Sale

      26 Gorham Ln, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,167 Sq Ft
      • Built 1971
      26 Gorham Ln, Middlebury, VT 05753

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Elizabeth Marino Champlain Valley Properties

  • 21 Seminary St, Middlebury, VT 05753
    21 Seminary St, Middlebury, VT 05753
    21 Seminary St, Middlebury, VT 05753
    /49

    $549,000

    • 5 Beds
    • 4.5 Baths
    • 3,630 Sq Ft

    21 Seminary St, Middlebury, VT 05753

    Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple

    Katrina Roberts Vermont Real Estate Company

    21 Seminary St, Middlebury, VT 05753
  • 76 Lindale Cir, Middlebury, VT 05753
    76 Lindale Cir, Middlebury, VT 05753
    76 Lindale Cir, Middlebury, VT 05753
    /24

    $75,000

    Sold Sep 10, 2025

    76 Lindale Cir, Middlebury, VT 05753

    • 2 Beds
    • 1.5 Baths
    • 720 Sq Ft
    • Built 1970

    Last Sold Summary

    • $104/SF
    • 2 Days On Market

    Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

    76 Lindale Cir, Middlebury, VT 05753
    • 503 Weybridge St, Middlebury, VT 05753
      503 Weybridge St, Middlebury, VT 05753
      503 Weybridge St, Middlebury, VT 05753
      /40

      Est $475,561

      Not Listed For Sale

      503 Weybridge St, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,380 Sq Ft
      • Built 1963
      503 Weybridge St, Middlebury, VT 05753

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Amey Ryan IPJ Real Estate

  • 103 Court St, Middlebury, VT 05753
    103 Court St, Middlebury, VT 05753
    103 Court St, Middlebury, VT 05753
    /42

    $570,000

    $105K PRICE DROP Pending
    • 5 Beds
    • 3.5 Baths
    • 3,160 Sq Ft

    103 Court St, Middlebury, VT 05753

    Opportunity Knocks in the conveniently located 5 bedroom home in Middlebury! The property is set back off the road on 2.4 acres with a partially fenced in yard and a deck that faces west. Have you ever wanted to have your own business at home and raise your family too, all in the same space? This home presents a multitude of opportunity; Multi-generational living, Home business or rent out the

    Bonnie Gridley RE/MAX North Professionals, Middlebury

    103 Court St, Middlebury, VT 05753
  • 101 Lindale Cir, Middlebury, VT 05753
    101 Lindale Cir, Middlebury, VT 05753
    101 Lindale Cir, Middlebury, VT 05753
    /15

    $70,000

    Sold Dec 01, 2025

    101 Lindale Cir, Middlebury, VT 05753

    • 2 Beds
    • 1 Bath
    • 940 Sq Ft
    • Built 1974

    Last Sold Summary

    • 7% Below List Price
    • $74/SF
    • 19 Days On Market

    Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

    101 Lindale Cir, Middlebury, VT 05753
    • 3 Gorham Ln, Middlebury, VT 05753
      3 Gorham Ln, Middlebury, VT 05753
      3 Gorham Ln, Middlebury, VT 05753
      /32

      Est $541,625

      Not Listed For Sale

      3 Gorham Ln, Middlebury, VT 05753

      • 3 Beds
      • 1.5 Baths
      • 1,784 Sq Ft
      • Built 1960
      3 Gorham Ln, Middlebury, VT 05753

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Amey Ryan IPJ Real Estate

  • 35 N Leno Ln, Middlebury, VT 05753
    35 N Leno Ln, Middlebury, VT 05753
    35 N Leno Ln, Middlebury, VT 05753
    /48

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,472 Sq Ft

    35 N Leno Ln, Middlebury, VT 05753

    Set on 10 private acres, this charming log home offers the perfect balance of privacy, open lawn, and wooded surroundings, creating a peaceful Vermont retreat just 10 minutes from downtown Middlebury. Inside, the warm wood interior, high ceilings, and skylights fill the home with an abundance of natural light, creating a bright and inviting atmosphere throughout. The open-concept living room,

    Heather Morse Coldwell Banker Hickok and Boardman

    35 N Leno Ln, Middlebury, VT 05753
  • 385 E Main St, Middlebury, VT 05753
    385 E Main St, Middlebury, VT 05753
    385 E Main St, Middlebury, VT 05753
    /26

    $399,000

    Sold Oct 02, 2025

    385 E Main St, Middlebury, VT 05753

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $331/SF
    • 42 Days On Market

    Current Estimated Value $376,607

    Last Listing Agent Sarah Peluso IPJ Real Estate

    385 E Main St, Middlebury, VT 05753
    • 567 Weybridge St, Middlebury, VT 05753
      567 Weybridge St, Middlebury, VT 05753
      567 Weybridge St, Middlebury, VT 05753
      /12

      Est $424,639

      Not Listed For Sale

      567 Weybridge St, Middlebury, VT 05753

      • 3 Beds
      • 1.5 Baths
      • 1,770 Sq Ft
      • Built 1957
      567 Weybridge St, Middlebury, VT 05753

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Amey Ryan IPJ Real Estate

  • 95 Seminary Street Extension, Middlebury, VT 05753
    95 Seminary Street Extension, Middlebury, VT 05753
    95 Seminary Street Extension, Middlebury, VT 05753
    /28

    $470,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,916 Sq Ft

    95 Seminary Street Extension, Middlebury, VT 05753

    This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck, the perfect place to entertain, relax, and take in views of your own private slice of Vermont.Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings. The spacious home is conveniently located just minutes from

    Sean Dye BHHS Vermont Realty Group/Vergennes

    95 Seminary Street Extension, Middlebury, VT 05753
  • 31 Evergreen Ln, Middlebury, VT 05753
    31 Evergreen Ln, Middlebury, VT 05753
    31 Evergreen Ln, Middlebury, VT 05753
    /47

    $340,000

    Sold Aug 18, 2026

    31 Evergreen Ln, Middlebury, VT 05753

    • 2 Beds
    • 2 Baths
    • 1,397 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $243/SF
    • 52 Days On Market

    Current Estimated Value $357,297

    Last Listing Agent David Parsons RE/MAX North Professionals - Burlington

    31 Evergreen Ln, Middlebury, VT 05753
    • 10 Gorham Ln, Middlebury, VT 05753
      10 Gorham Ln, Middlebury, VT 05753
      10 Gorham Ln, Middlebury, VT 05753
      /24

      Est $550,188

      Not Listed For Sale

      10 Gorham Ln, Middlebury, VT 05753

      • 3 Beds
      • 1.5 Baths
      • 1,598 Sq Ft
      • Built 1970
      10 Gorham Ln, Middlebury, VT 05753

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Foster

  • 10 Case St, Middlebury, VT 05753
    10 Case St, Middlebury, VT 05753
    10 Case St, Middlebury, VT 05753
    /32

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft

    10 Case St, Middlebury, VT 05753

    Welcome to your next home,10 Case Street, a charming 3-bedroom, 2-bath home dating back to 1840. Filled with character and warmth, this home features beautiful wood floors and the timeless appeal of an older Vermont property. Outside, there is plenty of garden space to create your own outdoor retreat, whether you envision flower gardens, vegetables, entertaining areas, or simply a peaceful place

    Nikhil Plouffe BHHS Vermont Realty Group/Middlebury

    10 Case St, Middlebury, VT 05753
  • 47 Barnes Brook Rd, Middlebury, VT 05753
    47 Barnes Brook Rd, Middlebury, VT 05753
    47 Barnes Brook Rd, Middlebury, VT 05753
    /9

    $520,000

    Sold Jun 22, 2026

    47 Barnes Brook Rd, Middlebury, VT 05753

    • 3 Beds
    • 2.5 Baths
    • 2,019 Sq Ft
    • Built 2026

    Last Sold Summary

    • 8% Above List Price
    • $258/SF

    Last Listing Agent Sarah Peluso IPJ Real Estate

    47 Barnes Brook Rd, Middlebury, VT 05753
    • 12 Gorham Ln, Middlebury, VT 05753
      12 Gorham Ln, Middlebury, VT 05753
      12 Gorham Ln, Middlebury, VT 05753
      /31

      Est $523,804

      Not Listed For Sale

      12 Gorham Ln, Middlebury, VT 05753

      • 3 Beds
      • 2 Baths
      • 1,338 Sq Ft
      • Built 1958
      12 Gorham Ln, Middlebury, VT 05753

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Amey Ryan IPJ Real Estate

  • 89 Court St, Middlebury, VT 05753
    89 Court St, Middlebury, VT 05753
    89 Court St, Middlebury, VT 05753
    /56

    $280,000

    $19K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    89 Court St, Middlebury, VT 05753

    This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with ¾ bathroom. Upstairs, you'll find three additional

    Bianca Perta Coldwell Banker Hickok and Boardman

    89 Court St, Middlebury, VT 05753
  • 68 Court St, Middlebury, VT 05753
    68 Court St, Middlebury, VT 05753
    68 Court St, Middlebury, VT 05753
    /34

    $390,000

    Sold Apr 09, 2026

    68 Court St, Middlebury, VT 05753

    • 4 Beds
    • 2 Baths
    • 1,652 Sq Ft
    • Built 1910

    Last Sold Summary

    • 5% Below List Price
    • $236/SF
    • 140 Days On Market

    Current Estimated Value $398,990

    Last Listing Agent Amey Ryan IPJ Real Estate

    68 Court St, Middlebury, VT 05753
    • 98 Peterson Terrace, Middlebury, VT 05753
      98 Peterson Terrace, Middlebury, VT 05753
      98 Peterson Terrace, Middlebury, VT 05753
      /22

      Est $350,746

      Not Listed For Sale

      98 Peterson Terrace, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,772 Sq Ft
      • Built 1975
      98 Peterson Terrace, Middlebury, VT 05753

      Last Sold Summary

      • 70 Days On Market

      Last Listing Agent Nancy Foster

  • 427 E Main St, Middlebury, VT 05753
    427 E Main St, Middlebury, VT 05753
    427 E Main St, Middlebury, VT 05753
    /42

    $432,000

    Sold Dec 23, 2025

    427 E Main St, Middlebury, VT 05753

    • 5 Beds
    • 2 Baths
    • 2,963 Sq Ft
    • Built 1800

    Last Sold Summary

    • 23% Below List Price
    • $146/SF
    • 167 Days On Market

    Current Estimated Value $492,185

    Last Listing Agent Levi Doria IPJ Real Estate

    427 E Main St, Middlebury, VT 05753
    • 57 Colonial Dr, Middlebury, VT 05753
      57 Colonial Dr, Middlebury, VT 05753
      57 Colonial Dr, Middlebury, VT 05753
      /31

      Est $532,055

      Not Listed For Sale

      57 Colonial Dr, Middlebury, VT 05753

      • 3 Beds
      • 3 Baths
      • 2,262 Sq Ft
      • Built 1972
      57 Colonial Dr, Middlebury, VT 05753

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • 681 Weybridge St, Middlebury, VT 05753
    681 Weybridge St, Middlebury, VT 05753
    681 Weybridge St, Middlebury, VT 05753
    /32

    $549,000

    Sold Jun 01, 2026

    681 Weybridge St, Middlebury, VT 05753

    • 3 Beds
    • 3.5 Baths
    • 1,696 Sq Ft
    • Built 1930

    Last Sold Summary

    • $324/SF
    • 5 Days On Market

    Current Estimated Value $538,601

    Last Listing Agent Sarah Peluso IPJ Real Estate

    681 Weybridge St, Middlebury, VT 05753
    • 19 Chipman Heights, Middlebury, VT 05753
      19 Chipman Heights, Middlebury, VT 05753
      19 Chipman Heights, Middlebury, VT 05753
      /27

      Est $749,389

      Not Listed For Sale

      19 Chipman Heights, Middlebury, VT 05753

      • 4 Beds
      • 3 Baths
      • 2,600 Sq Ft
      • Built 1953
      19 Chipman Heights, Middlebury, VT 05753

      Last Sold Summary

      • 224 Days On Market

      Last Listing Agent Nancy Foster

  • 442 E Main St, Middlebury, VT 05753
    442 E Main St, Middlebury, VT 05753
    442 E Main St, Middlebury, VT 05753
    /33

    $400,000

    Sold Aug 24, 2026

    442 E Main St, Middlebury, VT 05753

    • 4 Beds
    • 2 Baths
    • 1,815 Sq Ft
    • Built 1870

    Last Sold Summary

    • 11% Below List Price
    • $220/SF
    • 85 Days On Market

    Current Estimated Value $409,178

    Last Listing Agent Heather Foster-Provencher Champlain Valley Properties

    442 E Main St, Middlebury, VT 05753
    • 9 Chipman Heights, Middlebury, VT 05753
      9 Chipman Heights, Middlebury, VT 05753
      9 Chipman Heights, Middlebury, VT 05753
      /29

      Est $711,825

      Not Listed For Sale

      9 Chipman Heights, Middlebury, VT 05753

      • 4 Beds
      • 2.5 Baths
      • 2,196 Sq Ft
      • Built 1985
      9 Chipman Heights, Middlebury, VT 05753

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Beth Stanway IPJ Real Estate

  • 560 Route 30, Middlebury, VT 05753
    560 Route 30, Middlebury, VT 05753
    560 Route 30, Middlebury, VT 05753
    /37

    $782,000

    Sold Jun 25, 2026

    560 Route 30, Middlebury, VT 05753

    • 4 Beds
    • 3.5 Baths
    • 3,617 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $216/SF
    • 3 Days On Market

    Current Estimated Value $760,264

    Last Listing Agent Amey Ryan IPJ Real Estate

    560 Route 30, Middlebury, VT 05753
    • 73 N Pleasant St, Middlebury, VT 05753
      73 N Pleasant St, Middlebury, VT 05753
      73 N Pleasant St, Middlebury, VT 05753
      /42

      Est $374,703

      Not Listed For Sale

      73 N Pleasant St, Middlebury, VT 05753

      • 4 Beds
      • 2.5 Baths
      • 2,030 Sq Ft
      • Built 1900
      73 N Pleasant St, Middlebury, VT 05753

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • 29 N Pleasant St, Middlebury, VT 05753
    29 N Pleasant St, Middlebury, VT 05753
    29 N Pleasant St, Middlebury, VT 05753
    /18

    $595,000

    Sold Mar 18, 2026

    29 N Pleasant St, Middlebury, VT 05753

    • 4 Beds
    • 2,870 Sq Ft
    • Built 1900

    Last Sold Summary

    • $207/SF
    • 0 Days On Market

    Current Estimated Value $586,850

    Last Listing Agent Nancy Foster

    29 N Pleasant St, Middlebury, VT 05753
    • 104 Seymour St, Middlebury, VT 05753
      104 Seymour St, Middlebury, VT 05753
      104 Seymour St, Middlebury, VT 05753
      /29

      Est $492,847

      Not Listed For Sale

      104 Seymour St, Middlebury, VT 05753

      • 3 Beds
      • 2 Baths
      • 1,398 Sq Ft
      • Built 1900
      104 Seymour St, Middlebury, VT 05753

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • 1726 Munger St, Middlebury, VT 05753
    1726 Munger St, Middlebury, VT 05753
    1726 Munger St, Middlebury, VT 05753
    /40

    $215,000

    Sold Dec 19, 2025

    1726 Munger St, Middlebury, VT 05753

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $101/SF
    • 126 Days On Market

    Current Estimated Value $318,241

    Last Listing Agent Amey Ryan IPJ Real Estate

    1726 Munger St, Middlebury, VT 05753
    • 3 Ledgewood Ct, Middlebury, VT 05753
      3 Ledgewood Ct, Middlebury, VT 05753
      3 Ledgewood Ct, Middlebury, VT 05753
      /20

      Est $228,769

      Not Listed For Sale

      3 Ledgewood Ct, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,122 Sq Ft
      • Built 1989
      3 Ledgewood Ct, Middlebury, VT 05753

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent The Signature Realty Group Signature Properties of Vermont

  • 286 S Bingham St, Middlebury, VT 05753
    286 S Bingham St, Middlebury, VT 05753
    286 S Bingham St, Middlebury, VT 05753
    /38

    $315,000

    Sold Jul 24, 2026

    286 S Bingham St, Middlebury, VT 05753

    • 3 Beds
    • 1 Bath
    • 1,456 Sq Ft
    • Built 1820

    Last Sold Summary

    • 27% Above List Price
    • $216/SF
    • 10 Days On Market

    Last Listing Agent Amey Ryan IPJ Real Estate

    286 S Bingham St, Middlebury, VT 05753
    • 10 Woodbridge Ln, Middlebury, VT 05753
      10 Woodbridge Ln, Middlebury, VT 05753
      10 Woodbridge Ln, Middlebury, VT 05753
      /32

      Est $246,821

      Not Listed For Sale

      10 Woodbridge Ln, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,122 Sq Ft
      • Built 1981
      10 Woodbridge Ln, Middlebury, VT 05753

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Ali Sater Element Real Estate

  • 70 Maple St Unit 205, Middlebury, VT 05753
    70 Maple St Unit 205, Middlebury, VT 05753
    70 Maple St Unit 205, Middlebury, VT 05753
    /26

    $825,000

    Sold Mar 03, 2026

    70 Maple St Unit 205, Middlebury, VT 05753

    • 3 Beds
    • 3 Baths
    • 1,653 Sq Ft
    • Built 2007

    Last Sold Summary

    • 3% Below List Price
    • $499/SF
    • 85 Days On Market

    Last Listing Agent Sarah Peluso IPJ Real Estate

    70 Maple St Unit 205, Middlebury, VT 05753
    • 1 Woodbridge Ln, Middlebury, VT 05753
      1 Woodbridge Ln, Middlebury, VT 05753
      1 Woodbridge Ln, Middlebury, VT 05753
      /19

      Est $230,194

      Not Listed For Sale

      1 Woodbridge Ln, Middlebury, VT 05753

      • 2 Beds
      • 1.5 Baths
      • 1,080 Sq Ft
      • Built 1981
      1 Woodbridge Ln, Middlebury, VT 05753

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Nancy Foster

  • 4 Woodbridge Ln, Middlebury, VT 05753
    4 Woodbridge Ln, Middlebury, VT 05753
    4 Woodbridge Ln, Middlebury, VT 05753
    /29

    $270,000

    Sold Dec 16, 2025

    4 Woodbridge Ln, Middlebury, VT 05753

    • 3 Beds
    • 1 Bath
    • 1,122 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $241/SF
    • 2 Days On Market

    Last Listing Agent Sarah Peluso IPJ Real Estate

    4 Woodbridge Ln, Middlebury, VT 05753
    • 25 Lower Plains Rd, Middlebury, VT 05753
      25 Lower Plains Rd, Middlebury, VT 05753
      25 Lower Plains Rd, Middlebury, VT 05753
      /18

      Est $348,051

      Not Listed For Sale

      25 Lower Plains Rd, Middlebury, VT 05753

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1979
      25 Lower Plains Rd, Middlebury, VT 05753

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent k. Cory Foote BHHS Vermont Realty Group/Vergennes

  • 573 S Munger St, Middlebury, VT 05753
    573 S Munger St, Middlebury, VT 05753
    573 S Munger St, Middlebury, VT 05753
    /39

    $685,000

    Sold Oct 15, 2025

    573 S Munger St, Middlebury, VT 05753

    • 4 Beds
    • 3.5 Baths
    • 3,357 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $204/SF
    • 34 Days On Market

    Current Estimated Value $654,459

    Last Listing Agent Sarah Peluso IPJ Real Estate

    573 S Munger St, Middlebury, VT 05753
    • 24 Oak Dr, Middlebury, VT 05753
      24 Oak Dr, Middlebury, VT 05753
      24 Oak Dr, Middlebury, VT 05753
      /51

      Est $647,678

      Not Listed For Sale

      24 Oak Dr, Middlebury, VT 05753

      • 3 Beds
      • 2 Baths
      • 2,796 Sq Ft
      • Built 1987
      24 Oak Dr, Middlebury, VT 05753

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Beth Stanway IPJ Real Estate

  • 417 Painter Rd, Middlebury, VT 05753
    417 Painter Rd, Middlebury, VT 05753
    417 Painter Rd, Middlebury, VT 05753
    /60

    $632,000

    Sold Dec 08, 2025

    417 Painter Rd, Middlebury, VT 05753

    • 4 Beds
    • 3 Baths
    • 2,906 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $217/SF
    • 20 Days On Market

    Current Estimated Value $629,167

    Last Listing Agent Amey Ryan IPJ Real Estate

    417 Painter Rd, Middlebury, VT 05753

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