Middlebury, VT Homes

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  /31

  $595,000

  • 4 Beds
  • 2 Baths
  • 2,037 Sq Ft

  30 South St, Middlebury, VT 05753

  This classic village home is in a great location! Situated on South St., with sidewalks on both sides of the historical street as you head into town. You have no doubt driven by this home and admired its handsome Colonial facade many times. A brand new natural gas boiler has been installed! From the front door you enter into the living room space, with wood floors that continue throughout the

  

  Sarah Peluso

  IPJ Real Estate

  (802) 559-5212

  30 South St, Middlebury, VT 05753
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  /16

  $1,450 - $2,000 per month

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

  54 Main St, Middlebury, VT 05753

  Two bedroom apartment in the historic Rogers building overlooking Middlebury falls. Located at the site of the woolen mill in the heart of Middlebury. Provides an easy walk to Middlebury College. Available as summer rental. Available until September 1, 2026.Freshly renovated with hardwood floors throughout and new appliances.Hot water included.

  54 Main St, Middlebury, VT 05753
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  /7

  $425,000 Sold Aug 25, 2025

  45 Stonecrop Rd, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,516 Sq Ft

  Last Sold Summary

  • $280/SF
  • 0 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  45 Stonecrop Rd, Middlebury, VT 05753
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  /13

  Not Listed For Sale

  436 Middle Rd N, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft
  • Built 1940

  436 Middle Rd N, Middlebury, VT 05753

  Last Sold Summary

  • $139/SF
  • 183 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Nancy Foster Champlain Valley Properties
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  /34

  $410,000

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

  68 Court St, Middlebury, VT 05753

  Close to town and move-in ready! If you're in the market for a house with charm, character and convenience - you've landed in the right spot! Within walking and biking distance to local schools, healthcare, grocery stores, shopping and recreational opportunities, this home is certainly convenient. It also has some architectural flair, check out the ornate windows and interior trim! Plenty of

  

  Amey Ryan

  IPJ Real Estate

  (802) 210-3757

  68 Court St, Middlebury, VT 05753
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  /25

  $3,300 per month

  • 3 Beds
  • 1.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  45 Bakery Ln, Middlebury, VT 05753

  Welcome to The Annex, a charming three-bedroom, one and one half-bathroom guest house in the heart of Middlebury, Vermont. This exceptional property offers a central location, within walking distance to downtown, Middlebury College, Porter hospital, and restaurants. Situated on a private 1.3-acre estate next to the owner's historic brick colonial, The Annex provides a tranquil living experience

  Ray Fortier KW Vermont

  45 Bakery Ln, Middlebury, VT 05753
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  /46

  $410,000 Sold Feb 11, 2026

  86 Ossie Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1933

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 70 Days On Market

  Current Estimated Value $412,434

  Last Listing Agent Amey Ryan IPJ Real Estate

  86 Ossie Rd, Middlebury, VT 05753
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  /29

  Est $618,532 Not Listed For Sale

  6 Nedde Ln, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft
  • Built 1989

  6 Nedde Ln, Middlebury, VT 05753

  Last Sold Summary

  • 3% Above List Price
  • $331/SF
  • 5 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Amey Ryan IPJ Real Estate
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  /32

  $549,000 Under Contract

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

  681 Weybridge St, Middlebury, VT 05753

  A fantastic, in town location- across from Otter View Park, and down the street from Middlebury College and everything town has to offer! A 2017 addition included a first floor primary suite, making one level living easy. The well laid out floor plan includes a living room with hardwood floors that is open to the updated kitchen and dining areas. A powder room and laundry area round out this

  

  Sarah Peluso

  IPJ Real Estate

  (802) 210-3520

  681 Weybridge St, Middlebury, VT 05753
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  /16

  $1,450 - $2,000 per month

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

  54 Main St, Middlebury, VT 05753

  Two bedroom apartment in the historic Rogers building overlooking Middlebury falls. Located at the site of the woolen mill in the heart of Middlebury. Provides an easy walk to Middlebury College. Available as summer rental. Available until September 1, 2026.Freshly renovated with hardwood floors throughout and new appliances.Hot water included.

  54 Main St, Middlebury, VT 05753
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  /29

  $430,000 Sold Feb 12, 2026

  200 Butternut Ridge Dr, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 2,174 Sq Ft
  • Built 1966

  Last Sold Summary

  • 13% Below List Price
  • $198/SF
  • 143 Days On Market

  Current Estimated Value $453,706

  Last Listing Agent Nancy Foster Champlain Valley Properties

  200 Butternut Ridge Dr, Middlebury, VT 05753
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  /28

  Not Listed For Sale

  51 Seminary Street Extension, Middlebury, VT 05753

  • 9 Beds
  • 2.5 Baths
  • 5,428 Sq Ft
  • Built 1820

  51 Seminary Street Extension, Middlebury, VT 05753

  Last Sold Summary

  • $92/SF
  • 51 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Sarah Peluso IPJ Real Estate
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  /38

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  1456 Halladay Rd, Middlebury, VT 05753

  Located on over 10 acres with beautiful views of the Adirondacks, this well cared for, post and beam cape enjoys privacy and peaceful surroundings. Enjoy the views from the large deck, screened in porch, hot tub, or the in ground pool during warmer months! This home has many features you are looking for- including a large mudroom that connects the two car garage with a large storage area above.

  

  Sarah Peluso

  IPJ Real Estate

  (802) 242-8237

  1456 Halladay Rd, Middlebury, VT 05753
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  /53

  $1,470,000 Sold Nov 21, 2025

  1691 N Bingham St, Middlebury, VT 05753

  • 5 Beds
  • 4.5 Baths
  • 3,571 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Below List Price
  • $412/SF
  • 18 Days On Market

  Current Estimated Value $1,332,398

  Last Listing Agent Amey Ryan IPJ Real Estate

  1691 N Bingham St, Middlebury, VT 05753
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  /15

  Est $224,528 Not Listed For Sale

  9 Woodbridge Ln, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Built 1981

  9 Woodbridge Ln, Middlebury, VT 05753

  Last Sold Summary

  • 5% Above List Price
  • $198/SF
  • 14 Days On Market

  Last Sold Price $214,000

  Last Listing Agent Beth Stanway IPJ Real Estate
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  /60

  $899,000 Under Contract

  • 6 Beds
  • 5 Baths
  • 4,503 Sq Ft

  91 Old Pasture Ln, Middlebury, VT 05753

  Take some time and really reflect on how you want to live in Middlebury, Vermont! This property and the house that sits here can offer you an answer. The main house has a layout conducive to all kinds of options including a first floor primary suite, several rooms that could be used for home offices and creative spaces, gathering spaces in the eat-in kitchen, generous dining room and comfortable

  

  Amey Ryan

  IPJ Real Estate

  (802) 471-3395

  91 Old Pasture Ln, Middlebury, VT 05753
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  /28

  $315,000 Sold Feb 19, 2026

  52 School House Hill Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,830 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $172/SF
  • 40 Days On Market

  Last Listing Agent Breanna Dupuis RE/MAX North Professionals

  52 School House Hill Rd, Middlebury, VT 05753
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  /16

  Not Listed For Sale

  131 Lindale Cir, Middlebury, VT 05753

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2014

  131 Lindale Cir, Middlebury, VT 05753

  Last Sold Summary

  • $70/SF
  • 0 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC
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  /39

  $575,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  394 Cider Mill Rd, Middlebury, VT 05753

  This is the location you have been waiting for! Located on one of the most desirable streets in the area, this home sits on almost three acres with beautiful green mountain views! Well maintained, there are hardwood floors throughout, and plenty of natural light. Currently there is a mudroom, kitchen, dining room, living room and office/bedroom on the first floor, with a 3/4 bath. Upstairs there

  

  Sarah Peluso

  IPJ Real Estate

  (802) 441-2262

  394 Cider Mill Rd, Middlebury, VT 05753
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  /49

  $85,000 Sold May 21, 2025

  118 Lindale Cir, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1983

  Last Sold Summary

  • 10% Below List Price
  • $92/SF
  • 21 Days On Market

  Last Listing Agent Flex Realty Group Flex Realty

  118 Lindale Cir, Middlebury, VT 05753
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  /30

  Est $726,875 Not Listed For Sale

  19 N Bingham St, Middlebury, VT 05753

  • 4 Beds
  • 1 Bath
  • 2,172 Sq Ft
  • Built 1860

  19 N Bingham St, Middlebury, VT 05753

  Last Sold Summary

  • 77% Above List Price
  • $189/SF
  • 42 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Amey Ryan IPJ Real Estate
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  /11

  $199,000

  • Land
  • 0.6 Acre
  • $331,667 per Acre

  376 S Ridge Dr, Middlebury, VT 05753

  This lot in the popular South Ridge neighborhood is served by town water, town sewer and is build ready! The driveway has been roughed in and the utilities/services are at the edge of the building envelope. This is the only available lot in the neighborhood! The view from this house is easterly and southeasterly so you can watch the sun rise over the Green Mountains. South Ridge is a neighborhood

  

  Sarah Peluso

  IPJ Real Estate

  (802) 520-0544

  376 S Ridge Dr, Middlebury, VT 05753
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  /6

  $190,000 Sold Feb 04, 2026

  TBD Washington St, Middlebury, VT 05753

  • Land
  • 3 Acres
  • $63,333 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 3 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  TBD Washington St, Middlebury, VT 05753
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  /25

  Est $223,216 Not Listed For Sale

  23 Woodbridge Ln, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 1,122 Sq Ft
  • Built 1987

  23 Woodbridge Ln, Middlebury, VT 05753

  Last Sold Summary

  • 6% Above List Price
  • $187/SF
  • 11 Days On Market

  Last Sold Price $210,000

  Last Listing Agent The Signature Realty Group Signature Properties of Vermont
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  /14

  $220,000

  • Land
  • 9.8 Acres
  • $22,449 per Acre

  TBD Route 7 S, Middlebury, VT 05753

  Great piece of land in a great location! Secluded when you go up the old road/driveway. Easy access to Rutland or Burlington. Close to everything Middlebury has to offer including stores, restaurants and Middlebury College.

  

  Beth Stanway

  IPJ Real Estate

  (802) 427-7381

  TBD Route 7 S, Middlebury, VT 05753
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  /43

  $320,000 Sold Feb 12, 2026

  5 Duane Ct, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1945

  Last Sold Summary

  • $370/SF
  • 3 Days On Market

  Current Estimated Value $320,837

  Last Listing Agent Heather Morse Coldwell Banker Hickok and Boardman

  5 Duane Ct, Middlebury, VT 05753
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  /40

  Est $406,352 Not Listed For Sale

  1903 Quaker Village Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1840

  1903 Quaker Village Rd, Middlebury, VT 05753

  Last Sold Summary

  • 1% Below List Price
  • $247/SF
  • 8 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Jeff Olson BHHS Vermont Realty Group/Middlebury
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  /19

  $625,000

  • 5 Beds
  • 1.5 Baths
  • 2,236 Sq Ft

  1332 Cider Mill Rd, Middlebury, VT 05753

  This location does not come along often! Sited on the east side of Cider Mill road looking towards Middlebury College and the Green Mountains, and just 2.5 miles to downtown. Over 7 acres of land has been opened up to share the incredible eastern views. There is an old farmhouse on this land that is not currently livable. It would require a complete transformation or a new owner could start

  

  Sarah Peluso

  IPJ Real Estate

  (802) 523-4058

  1332 Cider Mill Rd, Middlebury, VT 05753
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  /9

  $655,000 Sold Dec 02, 2025

  53 Stonecrop Rd Unit 5.1, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 2,019 Sq Ft
  • Built 2025

  Last Sold Summary

  • 52% Above List Price
  • $324/SF
  • 113 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  53 Stonecrop Rd Unit 5.1, Middlebury, VT 05753
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  /40

  Est $621,967 Not Listed For Sale

  640 Sheep Farm Rd, Middlebury, VT 05753

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1847

  640 Sheep Farm Rd, Middlebury, VT 05753

  Last Sold Summary

  • 10% Above List Price
  • $252/SF
  • 6 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Sarah Peluso IPJ Real Estate
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  /11

  $139,000 Under Contract

  • Land
  • 0.46 Acre
  • $302,174 per Acre

  Lot 1C Daisy Ln, Middlebury, VT 05753

  Not finding what you're looking for in a house? Ever thought of just building exactly what you want? Find a right-sized house and build it here in East Middlebury! The flat lot is part of a small neighborhood and right next to Brown Field (a ball field). You'd be within close proximity to the Waybury Inn Restaurant & Pub, library, tennis courts, playground and miles of biking and hiking nearby.

  

  Amey Ryan

  IPJ Real Estate

  (802) 553-3632

  Lot 1C Daisy Ln, Middlebury, VT 05753
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  /51

  $650,000 Sold Sep 24, 2025

  719 Washington Street Extension, Middlebury, VT 05753

  • 4 Beds
  • 3 Baths
  • 2,930 Sq Ft
  • Built 1880

  Last Sold Summary

  • 6% Below List Price
  • $222/SF
  • 68 Days On Market

  Current Estimated Value $640,782

  Last Listing Agent Sarah Peluso IPJ Real Estate

  719 Washington Street Extension, Middlebury, VT 05753
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  /29

  Est $426,656 Not Listed For Sale

  706 Perkins Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1972

  706 Perkins Rd, Middlebury, VT 05753

  Last Sold Summary

  • 3% Above List Price
  • $360/SF
  • 17 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Jeff Olson BHHS Vermont Realty Group/Middlebury
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  /3

  $149,000

  • Land
  • 0.49 Acre
  • $304,082 per Acre

  TBD Middle Rd N, Middlebury, VT 05753

  In-town lots in Middlebury do not come available very often! So close to everything from this location. This great building lot has electric, public water and sewer at the street. Located across the street from the Middlebury Union Middle School. Sellers obtained a building permit from the Town of Middlebury which would need to be renewed by purchaser.

  

  Beth Stanway

  IPJ Real Estate

  (802) 588-8807

  TBD Middle Rd N, Middlebury, VT 05753
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  /42

  $420,000 Sold Sep 12, 2025

  62 Court St, Middlebury, VT 05753

  • 3 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $179/SF
  • 15 Days On Market

  Current Estimated Value $426,403

  Last Listing Agent Amey Ryan IPJ Real Estate

  62 Court St, Middlebury, VT 05753
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  /6

  Est $261,587 Not Listed For Sale

  609 Cave Rd, Middlebury, VT 05753

  609 Cave Rd, Middlebury, VT 05753

  Last Sold Summary

  • 116% Above List Price
  • 2 Days On Market

  Last Sold Price $121,000

  Last Listing Agent Diana Lynn Harvey Alison McCullough Real Estate
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  /8

  $699,500 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  24 Brush Ln Unit 8.2B, Middlebury, VT 05753

  Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom, single-level unit is on the second floor and will be ready for occupancy in January of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini

  

  Sarah Peluso

  IPJ Real Estate

  (802) 644-3918

  24 Brush Ln Unit 8.2B, Middlebury, VT 05753
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  /36

  $549,000 Sold Aug 29, 2025

  249 Fields Rd, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 1,695 Sq Ft
  • Built 2017

  Last Sold Summary

  • $324/SF
  • 2 Days On Market

  Current Estimated Value $535,784

  Last Listing Agent Michael Johnston Coldwell Banker Hickok and Boardman

  249 Fields Rd, Middlebury, VT 05753
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  /26

  Est $492,556 Not Listed For Sale

  3345 Quaker Village Rd, Middlebury, VT 05753

  • 2 Beds
  • 1 Bath
  • 1,039 Sq Ft
  • Built 2002

  3345 Quaker Village Rd, Middlebury, VT 05753

  Last Sold Summary

  • 4% Above List Price
  • $457/SF
  • 8 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Amey Ryan IPJ Real Estate
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  /5

  $388,900 New Construction

  • 2 Beds
  • 1.5 Baths
  • 1,516 Sq Ft

  35 Barnes Brook Rd Unit 9.4, Middlebury, VT 05753

  Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May of 2026. With energy efficiency at the forefront, each unit will

  

  Sarah Peluso

  IPJ Real Estate

  (802) 644-3557

  35 Barnes Brook Rd Unit 9.4, Middlebury, VT 05753

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