Middlebury, VT Homes

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  /60

  $699,000

  $26K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,684 Sq Ft

  466 E Main St, Middlebury, VT 05753

  Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills the air as you relax on your porch or savor a warm summer evening by the firepit. This classic Vermont farmhouse has been beautifully updated inside with a gorgeous custom kitchen complete with high end appliances that are a work of art. A 48" Italian gas range, Big Chill fridge and a handmade Moroccan brass

  

  Sarah Peluso

  IPJ Real Estate

  466 E Main St, Middlebury, VT 05753
• Explore Middlebury

• 

  

  

  /19

  $2,150

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 2,100 Sq Ft
  • Condo for Rent

  85 Court St Unit A, Middlebury, VT 05753

  85 Court Street – Middlebury, VTAvailable Now | 12-Month Lease | $2,150 Security DepositBeautifully Renovated 3-Bedroom Apartment Full of CharmIf you’re looking for a home with character and modern updates, this beautifully renovated 3-bedroom, 1-bath ground-level apartment offers the best of both. Located in the heart of Middlebury, you’ll be just minutes from downtown,

  85 Court St Unit A, Middlebury, VT 05753
• 

  

  

  /7

  $425,000

  Sold Aug 25, 2025

  45 Stonecrop Rd, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,516 Sq Ft
  • Built 2025

  Last Sold Summary

  • $280/SF
  • 0 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  45 Stonecrop Rd, Middlebury, VT 05753
• 

  

  

  /32

  Est $229,491

  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
• 

  

  

  /45

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft

  464 E Main St, Middlebury, VT 05753

  Nestled along the scenic banks of the Middlebury River, this beautifully updated vintage home offers a rare combination of historic character, modern comfort, and versatile living space. The main residence features three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or hobbies. Enjoy peaceful mornings and relaxing evenings in the screened porch overlooking the

  

  Beth Stanway

  IPJ Real Estate

  464 E Main St, Middlebury, VT 05753
• 

  

  /37

  $408,000

  Sold Mar 26, 2026

  46 Ossie Rd, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft
  • Built 1957

  Last Sold Summary

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

  Current Estimated Value $443,744

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

  46 Ossie Rd, Middlebury, VT 05753
• 

  

  /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

  • 51 Days On Market
• 

  

  /29

  $649,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,398 Sq Ft

  6 Nedde Ln, Middlebury, VT 05753

  Designed for effortless first-floor living, the home features a spacious primary suite on the main level, ideal for comfort and accessibility. A welcoming mudroom and convenient guest bath set the tone as you enter into the warm and inviting living space, complete with custom bookcases and a cozy gas fireplace, perfect for snowy Vermont evenings. Large windows and a deck overlooking the

  

  Amey Ryan

  IPJ Real Estate

  6 Nedde Ln, Middlebury, VT 05753
• 

  

  /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 $424,243

  Last Listing Agent Amey Ryan IPJ Real Estate

  86 Ossie Rd, Middlebury, VT 05753
• 

  

  /15

  Est $218,993

  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

  • 14 Days On Market
• 

  

  /47

  $1,150,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 2,661 Sq Ft

  182 Morningside Dr, Middlebury, VT 05753

  This in town location is incredible! At the end of a cul de sac, backing up to open lands for a beautiful pastoral view. The entire home was remodeled in 2015 by Cambium Construction, to create a beautiful, high end home- with the option to live all on one floor. From the outside you will appreciate the handsome shingle style structure, with lovely landscaping including stone pathways and stone

  

  Sarah Peluso

  IPJ Real Estate

  182 Morningside Dr, Middlebury, VT 05753
• 

  

  /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 $447,117

  Last Listing Agent Nancy Foster

  200 Butternut Ridge Dr, Middlebury, VT 05753
• 

  

  /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

  • 0 Days On Market
• 

  

  /51

  $679,000

  $16K PRICE DROP Under Contract

  • 5 Beds
  • 4.5 Baths
  • 4,840 Sq Ft

  29 Kings Row, Middlebury, VT 05753

  Perfect for anyone looking for an in-law suite, this home has a first-floor primary suite that is very spacious- giving its occupants a private space separate from the main house, including its own laundry room and office space! The generously sized mudroom entry and walk-in pantry separate this from the open concept kitchen/dining/living rooms. Flooded with natural light, the custom kitchen

  

  Sarah Peluso

  IPJ Real Estate

  29 Kings Row, Middlebury, VT 05753
• 

  

  /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 $1,516,159

  Last Listing Agent Amey Ryan IPJ Real Estate

  1691 N Bingham St, Middlebury, VT 05753
• 

  

  /30

  Est $823,841

  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

  • 42 Days On Market
• 

  

  /27

  $379,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  4 Overbrook Dr, Middlebury, VT 05753

  One level living is easy in this renovated condo! You will appreciate the updated wood floors throughout the entire unit. Natural light abounds in the open concept kitchen/living/dining area, and a new mini split is handy for both heat and air conditioning! The roomy kitchen has beautiful new quartz countertops, and newer appliances. A large pantry closet could house a stackable washer/dryer unit

  

  Sarah Peluso

  IPJ Real Estate

  4 Overbrook Dr, Middlebury, VT 05753
• 

  

  /6

  $520,000

  Sold May 14, 2026

  30 Meadowlark Ln Unit 7.6, 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

  30 Meadowlark Ln Unit 7.6, Middlebury, VT 05753
• 

  

  /25

  Est $214,526

  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

  • 11 Days On Market
• 

  

  /46

  $574,900

  $24K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  399 Pulp Mill Bridge Rd, Middlebury, VT 05753

  Charming and full of rich, Vermont character - a place you'll be proud to call home! According to local legend, in it's early years, this was the office for the Pulp Mill. Fast forward a few years and a local family decided to make it their home. Then for the next 50+ years this home has been continually expanded, improved and updated by the people who have loved living here! Today's home offers

  

  Amey Ryan

  IPJ Real Estate

  399 Pulp Mill Bridge Rd, Middlebury, VT 05753
• 

  

  /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
• 

  

  /60

  Est $742,995

  Not Listed For Sale

  200 Painter Hills Rd, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 2,683 Sq Ft
  • Built 2003

  200 Painter Hills Rd, Middlebury, VT 05753

  Last Sold Summary

  • 4 Days On Market
• 

  

  /41

  $450,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft

  6 Harrow Way, Middlebury, VT 05753

  Conveniently located in the sought after Buttolph Acres neighborhood, this neat and tidy home has been thoughtfully updated for you to move right in! Exterior siding was replaced with fiber cement clapboards, and insulation was added at that time for a energy efficient envelope. Walk into the open concept living/kitchen dining area, and you will appreciated the custom woodwork at every turn.

  

  Sarah Peluso

  IPJ Real Estate

  6 Harrow Way, Middlebury, VT 05753
• 

  

  /31

  $280,000

  Sold Mar 18, 2026

  82 Ossie Rd, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 1,330 Sq Ft
  • Built 1935

  Last Sold Summary

  • 11% Below List Price
  • $211/SF
  • 77 Days On Market

  Current Estimated Value $328,957

  Last Listing Agent Jill Fraga The Real Estate Company of Vermont, LLC

  82 Ossie Rd, Middlebury, VT 05753
• 

  

  /40

  Est $441,109

  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

  • 8 Days On Market
• 

  

  /60

  $1,100,000

  • 4 Beds
  • 5 Baths
  • 2,804 Sq Ft

  1844 Halladay Rd, Middlebury, VT 05753

  The classic Vermont farmhouse is on the market! This iconic property also enjoys classic Vermont mountain views- both of the Adirondacks and the Green mountains- that will complete the package. Nestled onto the landscape, the residence is perched up off the road looking west over conserved land to the Adirondacks. This property calls to you with its wrap around porch and handsome details, to come

  

  Sarah Peluso

  IPJ Real Estate

  1844 Halladay Rd, Middlebury, VT 05753
• 

  

  /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
• 

  

  /29

  Est $449,487

  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

  • 17 Days On Market
• 

  

  /31

  $549,000

  $146K PRICE DROP

  • 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

  30 South St, Middlebury, VT 05753
• 

  

  /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 $316,640

  Last Listing Agent Heather Morse Coldwell Banker Hickok and Boardman

  5 Duane Ct, Middlebury, VT 05753
• 

  

  /26

  Est $530,178

  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

  • 8 Days On Market
• 

  

  /50

  $529,000

  $20K PRICE DROP

  • 1,960 Sq Ft

  2337 Vt Route 7, Middlebury, VT 05753

  Here is a delightful opportunity to own a simply versatile property that has been carefully updated over the years. What started as a single family home has been beautifully transformed to this multi-use property. The larger section of the property includes 5 privately rented office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total

  

  Amey Ryan

  IPJ Real Estate

  2337 Vt Route 7, Middlebury, VT 05753
• 

  

  /9

  $430,000

  Sold Jul 23, 2026

  33 Barnes Brook Rd, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,516 Sq Ft
  • Built 2026

  Last Sold Summary

  • $284/SF

  Last Listing Agent Sarah Peluso IPJ Real Estate

  33 Barnes Brook Rd, Middlebury, VT 05753
• 

  

  /40

  Est $784,829

  Not Listed For Sale

  4310 Snake Mountain Rd, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 2,428 Sq Ft
  • Built 1999

  4310 Snake Mountain Rd, Middlebury, VT 05753

  Last Sold Summary

  • 187 Days On Market
• 

  

  /3

  $149,000

  Pending

  • Land
  • 21,344 Sq Ft
  • $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

  TBD Middle Rd N, Middlebury, VT 05753
• 

  

  /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
• 

  

  /39

  Est $386,031

  Not Listed For Sale

  436 E Main St, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft
  • Built 1850

  436 E Main St, Middlebury, VT 05753

  Last Sold Summary

  • 24 Days On Market
• 

  

  /6

  $199,000

  Under Contract

  • Land
  • 26,136 Sq Ft
  • $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

  376 S Ridge Dr, Middlebury, VT 05753
• 

  

  /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 $667,165

  Last Listing Agent Sarah Peluso IPJ Real Estate

  719 Washington Street Extension, Middlebury, VT 05753
• 

  /2

  Not Listed For Sale

  426 E Main St, Middlebury, VT 05753

  • 5 Beds
  • 2 Baths
  • 2,304 Sq Ft
  • Built 1920

  426 E Main St, Middlebury, VT 05753

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