Middlebury, VT Homes

• 

  

  

  /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

  TBD Route 7 S, 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 $406,493

  Last Listing Agent Amey Ryan IPJ Real Estate

  62 Court St, Middlebury, VT 05753
• 

  

  

  /26

  Est $306,306

  Not Listed For Sale

  5 Case St, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1967

  5 Case St, Middlebury, VT 05753

  Last Sold Summary

  • 7 Days On Market
• 

  

  

  /29

  $399,000

  $74K PRICE INCREASE

  • 3 Beds
  • 1 Bath
  • 1,724 Sq Ft

  26 and 28 Kings Row, Middlebury, VT 05753

  ***NEW PRICING*** Now includes +/- .48 building lot located at 28 Kings Row. Property has tremendous potential with the ability to purchase two lots. 26 Kings has a thoughtfully designed one-level home tucked away off the town maintained cul-de-sac, offering tranquility and privacy while keeping you close to the convenience and amenities of downtown living. Located at the end of Kings Row, the

  

  Levi Doria

  IPJ Real Estate

  26 and 28 Kings Row, Middlebury, VT 05753
• 

  

  

  /40

  $630,000

  Sold May 27, 2026

  1635 Route 74, Cornwall, VT 05753

  • 4 Beds
  • 3.5 Baths
  • 2,090 Sq Ft
  • Built 1832

  Last Sold Summary

  • 5% Above List Price
  • $301/SF
  • 3 Days On Market

  Current Estimated Value $609,696

  Last Listing Agent Beth Stanway IPJ Real Estate

  1635 Route 74, Cornwall, VT 05753
• 

  

  /31

  Est $374,726

  Not Listed For Sale

  58 Ossie Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1951

  58 Ossie Rd, Middlebury, VT 05753

  Last Sold Summary

  • 9 Days On Market
• 

  

  /37

  $595,000

  Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,116 Sq Ft

  458 E Main St, Middlebury, VT 05753

  1840 Village Home. This great multi-generational or multi-family home has four bedrooms in the main house, an eat-in kitchen with pantry/laundry room, formal dining room, large family room with gas burning soapstone stove, office/craft room, music room/den and 3.5 baths. One bedroom apartment has large living room, walk-in closet, and full kitchen and bath. Ideal as a mother-in-law residence or

  

  Beth Stanway

  IPJ Real Estate

  458 E Main St, Middlebury, VT 05753
• 

  

  /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 $629,755

  Last Listing Agent Michael Johnston Coldwell Banker Hickok and Boardman

  249 Fields Rd, Middlebury, VT 05753
• 

  

  /15

  Est $382,693

  Not Listed For Sale

  54 Ossie Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1949

  54 Ossie Rd, Middlebury, VT 05753

  Last Sold Summary

  • 24 Days On Market
• 

  

  /20

  $237,500

  • 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. Combining comfort, convenience, and thoughtful updates, this move-in-ready home is ideal for first-time buyers, downsizers, or anyone looking for low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating

  

  Beth Stanway

  IPJ Real Estate

  11 Ledgewood Ct, Middlebury, VT 05753
• 

  

  /7

  $425,000

  Sold Aug 28, 2025

  37 Stonecrop Rd, Middlebury, VT 05753

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

  Last Sold Summary

  • 19% Above List Price
  • $280/SF
  • 6 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  37 Stonecrop Rd, Middlebury, VT 05753
• 

  

  /20

  Est $388,607

  Not Listed For Sale

  13 Overbrook Dr, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1988

  13 Overbrook Dr, Middlebury, VT 05753

  Last Sold Summary

  • 28 Days On Market
• 

  

  /36

  $249,000

  Pending

  • Land
  • 10.14 Acres
  • $24,556 per Acre

  286 S Bingham St, Middlebury, VT 05753

  Over 10 acres with pretty great views to the west. There's a house in need of rehab or demolition and rebuild. There is plenty of road frontage topotentially subdivide the parcel. Due diligence will have to be done by the buyer. House and outbuildings are sold "as is" and there is no information about the existing water source or septic or household systems. Preliminary test pits to see about

  

  Amey Ryan

  IPJ Real Estate

  286 S Bingham St, Middlebury, VT 05753
• 

  

  /6

  $430,000

  Sold Jul 21, 2026

  14 Meadowlark Ln Unit 7.2, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,538 Sq Ft
  • Built 2026

  Last Sold Summary

  • 11% Above List Price
  • $280/SF
  • 98 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  14 Meadowlark Ln Unit 7.2, Middlebury, VT 05753
• 

  

  /30

  Est $404,557

  Not Listed For Sale

  12 Overbrook Dr, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1988

  12 Overbrook Dr, Middlebury, VT 05753

  Last Sold Summary

  • 12 Days On Market
• 

  

  /32

  $325,000

  Under Contract

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

  17 Bunny Ln, Middlebury, VT 05753

  Located at the end of the road, an affordable home with a welcoming front porch and garage awaits. Wood floors in the living areas and a propane stove in the living room for chilly nights. A first-floor office could serve as a bedroom, and a bath with laundry is convenient. Upstairs are four bedrooms and two bathrooms. The one-car garage is extra deep, with a back space for great storage. Located

  

  Sarah Peluso

  IPJ Real Estate

  17 Bunny Ln, Middlebury, VT 05753
• 

  

  /38

  $491,000

  Sold Jan 22, 2026

  30 Mountain View Ln, Middlebury, VT 05753

  • 4 Beds
  • 3 Baths
  • 1,760 Sq Ft
  • Built 1991

  Last Sold Summary

  • 17% Below List Price
  • $279/SF
  • 130 Days On Market

  Current Estimated Value $520,869

  Last Listing Agent Beth Stanway IPJ Real Estate

  30 Mountain View Ln, Middlebury, VT 05753
• 

  

  /21

  Est $369,570

  Not Listed For Sale

  21 Danyow Dr, Middlebury, VT 05753

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1957

  21 Danyow Dr, Middlebury, VT 05753

  Last Sold Summary

  • 3 Days On Market
• 

  

  /30

  $275,000

  $24K PRICE DROP Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  7 Evergreen Ln, Middlebury, VT 05753

  Easy condo living can be just the right fit for someone that doesn't want to shovel, mow the lawn or navigate home repairs like a roof replacements! All you need to do is turn the inside into the space you want to be in! Whether you are looking to downsize, purchase your first home or your forever home this two bedroom condo could be the perfect fit. On the main floor, just inside the mudroom,

  

  Amey Ryan

  IPJ Real Estate

  7 Evergreen Ln, Middlebury, VT 05753
• 

  

  /30

  $372,500

  Sold Mar 20, 2026

  44 Lower Plains Rd, Middlebury, VT 05753

  • 6 Beds
  • 3 Baths
  • 2,415 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Above List Price
  • $154/SF
  • 5 Days On Market

  Current Estimated Value $434,039

  Last Listing Agent Elizabeth Hogan Coldwell Banker Hickok and Boardman

  44 Lower Plains Rd, Middlebury, VT 05753
• 

  

  /17

  Est $415,633

  Not Listed For Sale

  276 Monroe St, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1980

  276 Monroe St, Middlebury, VT 05753

  Last Sold Summary

  • 13 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
• 

  

  /24

  $352,226

  Sold Oct 08, 2025

  446 Mead Ln, Middlebury, VT 05753

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1981

  Last Sold Summary

  • $314/SF
  • 9 Days On Market

  Current Estimated Value $328,120

  Last Listing Agent Nancy Foster

  446 Mead Ln, Middlebury, VT 05753
• 

  

  /22

  Est $377,577

  Not Listed For Sale

  235 Rogers Rd, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1979

  235 Rogers Rd, Middlebury, VT 05753

  Last Sold Summary

  • 127 Days On Market
• 

  

  /33

  $699,500

  New Construction

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

  40 Brush Ln Unit 8.3B, 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 March 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

  40 Brush Ln Unit 8.3B, Middlebury, VT 05753
• 

  

  /11

  $430,000

  Sold Apr 30, 2026

  22 Meadowlark Ln Unit 7.4, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,538 Sq Ft
  • Built 2026

  Last Sold Summary

  • 26% Below List Price
  • $280/SF
  • 42 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  22 Meadowlark Ln Unit 7.4, Middlebury, VT 05753
• 

  

  /39

  Est $452,668

  Not Listed For Sale

  209 Danyow Dr, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft
  • Built 1959

  209 Danyow Dr, Middlebury, VT 05753

  Last Sold Summary

  • 19 Days On Market
• 

  

  /8

  $455,000

  New Construction $28K PRICE DROP Under Contract

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

  54 Brush Ln Unit 8.4B, 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 three-bedroom, single-level unit is on the second floor and will be ready for occupancy in April of 2026. To be built with

  

  Sarah Peluso

  IPJ Real Estate

  54 Brush Ln Unit 8.4B, Middlebury, VT 05753
• 

  

  /32

  $625,000

  Sold Sep 30, 2025

  487 Burnham Dr, Middlebury, VT 05753

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $259/SF
  • 28 Days On Market

  Current Estimated Value $657,194

  Last Listing Agent Amey Ryan IPJ Real Estate

  487 Burnham Dr, Middlebury, VT 05753
• 

  

  /45

  Est $484,388

  Not Listed For Sale

  23 Fairview Cir, Middlebury, VT 05753

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1984

  23 Fairview Cir, Middlebury, VT 05753

  Last Sold Summary

  • 5 Days On Market
• 

  

  /9

  $765,000

  New Construction

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

  78 Brush Ln Unit 10.6, 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 duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house

  

  Sarah Peluso

  IPJ Real Estate

  78 Brush Ln Unit 10.6, Middlebury, VT 05753
• 

  

  /16

  $625,000

  Sold Nov 14, 2025

  70 Maple St Unit 307, Middlebury, VT 05753

  • 2 Beds
  • 2 Baths
  • 1,345 Sq Ft
  • Built 2007

  Last Sold Summary

  • $465/SF
  • 15 Days On Market

  Last Listing Agent Amey Ryan IPJ Real Estate

  70 Maple St Unit 307, Middlebury, VT 05753
• 

  

  /24

  Est $442,312

  Not Listed For Sale

  5 Swanage Ct, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1976

  5 Swanage Ct, Middlebury, VT 05753

  Last Sold Summary

  • 6 Days On Market
• 

  

  /6

  $765,000

  New Construction Under Contract

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

  30 Barnes Brook Rd Unit 10.4, 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 duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house

  

  Sarah Peluso

  IPJ Real Estate

  30 Barnes Brook Rd Unit 10.4, Middlebury, VT 05753
• 

  

  /8

  $717,700

  Sold Mar 19, 2026

  24 Brush Ln Unit 8.2B, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Above List Price
  • $432/SF

  Last Listing Agent Sarah Peluso IPJ Real Estate

  24 Brush Ln Unit 8.2B, Middlebury, VT 05753
• 

  

  /17

  Not Listed For Sale

  74 Court St, Middlebury, VT 05753

  • 6 Beds
  • 4 Baths
  • 2,540 Sq Ft
  • Built 1920

  74 Court St, Middlebury, VT 05753

  Last Sold Summary

  • 258 Days On Market
• 

  

  /8

  $585,000

  New Construction

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

  39 Barnes Brook Rd Unit 9.3, 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 two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house

  

  Sarah Peluso

  IPJ Real Estate

  39 Barnes Brook Rd Unit 9.3, Middlebury, VT 05753
• 

  

  /40

  $875,000

  Sold Nov 07, 2025

  218 S Ridge Dr Unit 8, Middlebury, VT 05753

  • 3 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 2007

  Last Sold Summary

  • 26% Above List Price
  • $379/SF
  • 3 Days On Market

  Current Estimated Value $895,174

  Last Listing Agent Amey Ryan IPJ Real Estate

  218 S Ridge Dr Unit 8, Middlebury, VT 05753
• 

  

  /33

  Est $722,914

  Not Listed For Sale

  292 Chipman Park, Middlebury, VT 05753

  • 4 Beds
  • 2.5 Baths
  • 2,154 Sq Ft
  • Built 1933

  292 Chipman Park, Middlebury, VT 05753

  Last Sold Summary

  • 5 Days On Market
• 

  

  /9

  $499,000

  New Construction $41K PRICE DROP Under Contract

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

  74 Brush Ln Unit 10.5, 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 three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront,

  

  Sarah Peluso

  IPJ Real Estate

  74 Brush Ln Unit 10.5, Middlebury, VT 05753

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