Middlebury, VT Homes

• 

  

  

  /50

  $489,000

  $60K 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 private office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for

  

  Amey Ryan

  IPJ Real Estate

  2337 Vt Route 7, Middlebury, VT 05753
• Explore Middlebury

• 

  

  

  /23

  $2,500

  Total Monthly Price

  • 3 Beds
  • 1.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  800 Us-7, Middlebury, VT 05753

  Three bedroom, single family home, split level. Upper level has 3 bed rooms, 3/4 bath, kitchen, Living Room with Heat Pump, Dining Room. Master Bedroom has Heat Pump. All refinished hardwood floors. Kitchen has new electric range.Lower level has 2 bonus spaces 13x21`, 11x 14ft. Half bath. Laundry Room with washer and dryer. Extra deep and wide single car garage.Front screened in

  800 Us-7, 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 $419,545

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

  46 Ossie Rd, Middlebury, VT 05753
• 

  

  

  /46

  Est $399,727

  Not Listed For Sale

  800 Route 7 S, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 2,300 Sq Ft
  • Built 1965

  800 Route 7 S, Middlebury, VT 05753

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Connor Johnson KW Vermont
• 

  

  

  /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
• 

  

  /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 $398,177

  Last Listing Agent Amey Ryan IPJ Real Estate

  86 Ossie Rd, Middlebury, VT 05753
• 

  

  /19

  Est $487,501

  Not Listed For Sale

  915 Lower Foote St, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft
  • Built 1998

  915 Lower Foote St, Middlebury, VT 05753

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Nancy Larrow BHHS Vermont Realty Group/Vergennes
• 

  

  /28

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  12 Little Pond Rd, Middlebury, VT 05753

  Welcome to this delightful end-unit condo, where abundant natural light and a thoughtful layout create an inviting, comfortable home. Designed for easy living, the main level offers everything you need for day-to-day life, including a spacious primary suite with a walk-in shower (modified with grab bar and seat), generous vanity, deep linen closet, and ample wardrobe storage. A second bedroom on

  

  Amey Ryan

  IPJ Real Estate

  12 Little Pond Rd, 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 $446,619

  Last Listing Agent Nancy Foster

  200 Butternut Ridge Dr, Middlebury, VT 05753
• 

  

  /36

  Est $615,036

  Not Listed For Sale

  249 Fields Rd, Middlebury, VT 05753

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

  249 Fields Rd, Middlebury, VT 05753

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Michael Johnston Coldwell Banker Hickok and Boardman
• 

  

  /49

  $650,000

  $49K PRICE DROP

  • 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
• 

  

  /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 $1,471,905

  Last Listing Agent Amey Ryan IPJ Real Estate

  1691 N Bingham St, Middlebury, VT 05753
• 

  

  /15

  Est $221,792

  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

  Last Listing Agent Beth Stanway IPJ Real Estate
• 

  

  /37

  $785,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,288 Sq Ft

  200 Morningside Dr, Middlebury, VT 05753

  On a quaint cul-de-sac in a sought-after in-town Middlebury location, this home has been thoughtfully cared for and prepared for your arrival! The spacious layout features a first floor with a mudroom entry, and handsome kitchen with custom red birch cabinets built by Stark Mountain Woodworking. Stainless steel appliances and quartz countertops were also added during that renovation. The kitchen

  

  Sarah Peluso

  IPJ Real Estate

  200 Morningside 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
• 

  

  /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

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC
• 

  

  /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
• 

  

  /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
• 

  

  /25

  Est $222,371

  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

  Last Listing Agent The Signature Realty Group Signature Properties of Vermont
• 

  

  /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 $309,963

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

  82 Ossie Rd, Middlebury, VT 05753
• 

  

  /60

  Est $738,634

  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

  Last Listing Agent Alicia Fleming Rise Realty
• 

  

  /60

  $1,100,000

  Under Contract

  • 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
• 

  

  /40

  Est $461,439

  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

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

  

  /52

  $1,250,000

  • 5 Beds
  • 4.5 Baths
  • 3,997 Sq Ft

  40 South St, Middlebury, VT 05753

  A remarkable Middlebury home where thoughtful craftsmanship, refined finishes, and effortless livability come together beautifully. Meticulously renovated in 2016/17, this distinctive home has been transformed into an elegant retreat designed equally well for gracious entertaining and comfortable everyday living. The main level offers beautifully proportioned spaces, including a spectacular

  

  Amey Ryan

  IPJ Real Estate

  40 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 $315,391

  Last Listing Agent Heather Morse Coldwell Banker Hickok and Boardman

  5 Duane Ct, Middlebury, VT 05753
• 

  

  /29

  Est $468,303

  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

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

  

  /34

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  922 Happy Valley Rd, Middlebury, VT 05753

  A private garden setting just minutes from the heart of Middlebury, this thoughtfully cared-for home offers an appealing combination of beauty, ease and understated elegance. Surrounded by mature hedgerows and spectacular gardens, the property feels wonderfully secluded while keeping the shops, restaurants and cultural life of Middlebury close at hand. Clean lines and a fresh, uncluttered

  

  Amey Ryan

  IPJ Real Estate

  922 Happy Valley Rd, 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
• 

  

  /26

  Est $537,758

  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

  Last Listing Agent Amey Ryan IPJ Real Estate
• 

  

  /6

  $499,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

  32 Barnes Brook Rd Unit 10.3, Middlebury, VT 05753

  Qualified pricing - check 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 three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be

  

  Sarah Peluso

  IPJ Real Estate

  32 Barnes Brook Rd Unit 10.3, Middlebury, VT 05753
• 

  

  /32

  $340,000

  Sold Aug 31, 2026

  17 Bunny Ln, Middlebury, VT 05753

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Above List Price
  • $154/SF
  • 3 Days On Market

  Current Estimated Value $368,142

  Last Listing Agent Sarah Peluso IPJ Real Estate

  17 Bunny Ln, 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

  Last Listing Agent Sarah Peluso IPJ Real Estate
• 

  

  /14

  $220,000

  Pending

  • 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

  TBD Route 7 S, 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 $393,717

  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

  Last Listing Agent Sue Walsh BHHS Vermont Realty Group/Middlebury
• 

  

  /20

  $237,500

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,122 Sq Ft

  11 Ledgewood Ct, Middlebury, VT 05753

  Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. This location is ideal for easy access to local shops, restaurants and parks and offers low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating a fresh and inviting space to call home. The three

  

  Beth Stanway

  IPJ Real Estate

  11 Ledgewood Ct, 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 $627,024

  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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