Middlebury, VT Homes

• 

  

  

  /31

  $540,000

  Sold Jul 31, 2025

  72 Juniper Ln, Middlebury, VT 05753

  • 4 Beds
  • 3 Baths
  • 3,788 Sq Ft
  • Built 1967

  Last Sold Summary

  • 22% Below List Price
  • $143/SF
  • 44 Days On Market

  Current Estimated Value $594,837

  Last Listing Agent Sarah Peluso IPJ Real Estate

  72 Juniper Ln, Middlebury, VT 05753
• 

  

  

  /27

  Est $345,173

  Not Listed For Sale

  3 Twin Cir, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1986

  3 Twin Cir, Middlebury, VT 05753

  Last Sold Summary

  • 3 Days On Market
• 

  

  

  /8

  $388,900

  New Construction

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

  41 Barnes Brook Rd Unit 9.2, 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

  41 Barnes Brook Rd Unit 9.2, Middlebury, VT 05753
• 

  

  

  /36

  $379,000

  Sold Sep 30, 2025

  1 Overbrook Dr, Middlebury, VT 05753

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1988

  Last Sold Summary

  • $376/SF
  • 7 Days On Market

  Current Estimated Value $391,380

  Last Listing Agent Sue Mackey BHHS Vermont Realty Group/Middlebury

  1 Overbrook Dr, Middlebury, VT 05753
• 

  

  

  /37

  Est $725,751

  Not Listed For Sale

  34 Seminary St, Middlebury, VT 05753

  • 4 Beds
  • 3 Baths
  • 3,219 Sq Ft
  • Built 1830

  34 Seminary St, Middlebury, VT 05753

  Last Sold Summary

  • 33 Days On Market
• 

  

  /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

  35 Barnes Brook Rd Unit 9.4, Middlebury, VT 05753
• 

  

  /25

  $385,000

  Sold May 13, 2026

  17 Twin Cir, Middlebury, VT 05753

  • 2 Beds
  • 2.5 Baths
  • 1,894 Sq Ft
  • Built 1988

  Last Sold Summary

  • $203/SF
  • 6 Days On Market

  Current Estimated Value $385,386

  Last Listing Agent Heather Foster-Provencher Champlain Valley Properties

  17 Twin Cir, Middlebury, VT 05753
• 

  

  /49

  Est $809,207

  Not Listed For Sale

  49 South St, Middlebury, VT 05753

  • 5 Beds
  • 2.5 Baths
  • 2,640 Sq Ft
  • Built 1920

  49 South St, Middlebury, VT 05753

  Last Sold Summary

  • 84 Days On Market
• 

  

  /6

  $499,000

  New Construction

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

  86 Birch Dr Unit 10.7, 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

  86 Birch Dr Unit 10.7, Middlebury, VT 05753
• 

  

  /8

  $480,000

  Sold Feb 19, 2026

  14 Brush Ln Unit 8.1A, Middlebury, VT 05753

  • 2 Beds
  • 2 Baths
  • 1,434 Sq Ft
  • Built 2026

  Last Sold Summary

  • 13% Above List Price
  • $335/SF

  Last Listing Agent Sarah Peluso IPJ Real Estate

  14 Brush Ln Unit 8.1A, Middlebury, VT 05753
• 

  

  /24

  Est $304,417

  Not Listed For Sale

  9 Washington Street Extension, Middlebury, VT 05753

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1969

  9 Washington Street Extension, Middlebury, VT 05753

  Last Sold Summary

  • 9 Days On Market
• 

  

  /7

  $150,000

  • Land
  • 23,522 Sq Ft
  • $277,778 per Acre

  2 Wilmar St, Middlebury, VT 05753

  BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial

  Jason Saphire www.HomeZu.com

  2 Wilmar St, Middlebury, VT 05753
• 

  

  /29

  $300,000

  Sold Oct 31, 2025

  68 Otterside Ct, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,420 Sq Ft
  • Built 1974

  Last Sold Summary

  • 5% Above List Price
  • $211/SF
  • 7 Days On Market

  Current Estimated Value $288,125

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

  68 Otterside Ct, Middlebury, VT 05753
• 

  /2

  Not Listed For Sale

  193 Washington Street Extension, Middlebury, VT 05753

  • 3 Beds
  • 3 Baths
  • 1,737 Sq Ft
  • Built 1961

  193 Washington Street Extension, Middlebury, VT 05753
• 

  

  /43

  $479,000

  $70K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,213 Sq Ft

  35 Ossie Rd, Middlebury, VT 05753

  Spacious East Middlebury Ranch on 1.20 Acres with Mountain ViewsSet on a generous 1.20-acre lot with a beautiful Green Mountain backdrop, this inviting ranch-style home offers comfort, flexibility, and room to grow. The property includes an attached two-car garage plus a separate detached building—perfect for hobbies, a workshop, or a small business—complete with its own power supply. Home

  Roxanna Emilo Emilo Real Estate, LLC

  35 Ossie Rd, Middlebury, VT 05753
• 

  

  /39

  $562,500

  Sold Apr 02, 2026

  394 Cider Mill Rd, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1924

  Last Sold Summary

  • 30% Below List Price
  • $289/SF
  • 293 Days On Market

  Current Estimated Value $578,073

  Last Listing Agent Sarah Peluso IPJ Real Estate

  394 Cider Mill Rd, Middlebury, VT 05753
• 

  

  /28

  Est $356,504

  Not Listed For Sale

  41 Court St, Middlebury, VT 05753

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1880

  41 Court St, Middlebury, VT 05753

  Last Sold Summary

  • 52 Days On Market
• 

  

  /48

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft

  2801 Route 7 S, Middlebury, VT 05753

  Looking for somewhere truly special to call home? This exceptional property offers 2,140 square feet of beautifully finished living space with 3 bedrooms, 2 baths, and breathtaking Green Mountain views from its private backyard and expansive deck. Meticulously rebuilt from top to bottom by the builder-owner, this home delivers the quality, efficiency, and peace of mind of new construction.

  Rob Foley Flat Fee Real Estate

  2801 Route 7 S, Middlebury, VT 05753
• 

  

  /22

  $240,000

  Sold Sep 19, 2025

  55 Ossie Rd, Middlebury, VT 05753

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 2000

  Last Sold Summary

  • $225/SF
  • 1 Day On Market

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

  55 Ossie Rd, Middlebury, VT 05753
• 

  

  /40

  Est $572,000

  Not Listed For Sale

  2672 Weybridge Rd, Middlebury, VT 05753

  • 4 Beds
  • 3.5 Baths
  • 2,848 Sq Ft
  • Built 1825

  2672 Weybridge Rd, Middlebury, VT 05753

  Last Sold Summary

  • 221 Days On Market
• 

  

  /13

  $399,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  54 Court St, Middlebury, VT 05753

  Centrally located two-unit residential property within walking distance of downtown Middlebury, local shops, restaurants, and both the elementary and high schools. This property offers flexibility for a variety of uses, with one unit currently vacant—providing an opportunity for owner-occupancy while generating rental income from the second unit to help offset expenses. It presents a practical

  k. Cory Foote BHHS Vermont Realty Group/Vergennes

  54 Court St, Middlebury, VT 05753
• 

  

  /8

  $699,500

  Sold May 01, 2026

  10 Brush Ln Unit 8.1B, Middlebury, VT 05753

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

  Last Sold Summary

  • 45% Above List Price
  • $421/SF
  • 182 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  10 Brush Ln Unit 8.1B, Middlebury, VT 05753
• 

  

  /8

  Est $305,815

  Not Listed For Sale

  11 Willard St, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 1,526 Sq Ft
  • Built 1850

  11 Willard St, Middlebury, VT 05753

  Last Sold Summary

  • 25 Days On Market
• 

  

  /7

  $150,000

  • Land
  • 22,651 Sq Ft
  • $288,462 per Acre

  4 Wilmar St, Middlebury, VT 05753

  BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial

  Jason Saphire www.HomeZu.com

  4 Wilmar St, Middlebury, VT 05753
• 

  

  /10

  $700,000

  Sold May 19, 2026

  371 Weybridge St, Middlebury, VT 05753

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft
  • Built 1920

  Last Sold Summary

  • 1% Above List Price
  • $349/SF
  • 5 Days On Market

  Current Estimated Value $701,294

  Last Listing Agent Sarah Peluso IPJ Real Estate

  371 Weybridge St, Middlebury, VT 05753
• 

  

  /39

  Est $834,836

  Not Listed For Sale

  364 Weybridge St, Middlebury, VT 05753

  • 4 Beds
  • 2 Baths
  • 2,053 Sq Ft
  • Built 1900

  364 Weybridge St, Middlebury, VT 05753

  Last Sold Summary

  • 132 Days On Market
• 

  

  /47

  $359,900

  $20K PRICE DROP Under Contract

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

  31 Evergreen Ln, Middlebury, VT 05753

  Discover this stunning end-unit condominium nestled in one of Middlebury's most charming neighborhoods — where thoughtful updates, effortless living, and a peaceful natural setting come together beautifully.The main level is designed for ease and comfort, featuring an open-concept living and dining area bathed in natural light from expansive windows and sliding doors. Step outside onto your

  David Parsons RE/MAX North Professionals - Burlington

  31 Evergreen Ln, Middlebury, VT 05753
• 

  

  /9

  $525,000

  Sold Sep 04, 2025

  33 Stonecrop Rd, Middlebury, VT 05753

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

  Last Sold Summary

  • 22% Above List Price
  • $260/SF
  • 15 Days On Market

  Last Listing Agent Sarah Peluso IPJ Real Estate

  33 Stonecrop Rd, Middlebury, VT 05753
• 

  

  /39

  Est $1,068,701

  Not Listed For Sale

  202 Weybridge St, Middlebury, VT 05753

  • 5 Beds
  • 3.5 Baths
  • 2,804 Sq Ft
  • Built 1818

  202 Weybridge St, Middlebury, VT 05753

  Last Sold Summary

  • 48 Days On Market
• 

  

  /33

  $400,000

  $49K PRICE DROP

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

  442 E Main St, Middlebury, VT 05753

  This inviting home offers a bright, comfortable layout designed for easy everyday living. The main level flows naturally between the kitchen, dining and living spaces, creating a welcoming environment for gatherings or quiet evenings at home. The updated kitchen blends the convenience of modern living with the charm and character of an older home. Upstairs, a large full bath serves the bedroom

  Heather Foster-Provencher Champlain Valley Properties

  442 E Main St, Middlebury, VT 05753
• 

  

  /27

  $225,000

  Sold Oct 24, 2025

  3680 Case St, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1980

  Last Sold Summary

  • $206/SF
  • 13 Days On Market

  Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

  3680 Case St, Middlebury, VT 05753
• 

  

  /27

  Est $420,604

  Not Listed For Sale

  341 Weybridge St, Middlebury, VT 05753

  • 2 Beds
  • 1.5 Baths
  • 1,156 Sq Ft
  • Built 1900

  341 Weybridge St, Middlebury, VT 05753

  Last Sold Summary

  • 18 Days On Market
• 

  

  /17

  $695,000

  • 5 Beds
  • 2.5 Baths
  • 3,827 Sq Ft

  5971 Snake Mountain Rd, Middlebury, VT 05753

  Set on 5.25 picturesque acres offering access to 1,200 acres of Snake Mountain Wildlife Management Area, this beautifully restored farmhouse offers exceptional privacy, timeless character, and breathtaking Green Mountain views. Extensively renovated while preserving its historic charm, the home seamlessly blends classic Vermont architecture with modern comfort. The welcoming foyer opens to

  Rob Foley Flat Fee Real Estate

  5971 Snake Mountain Rd, Middlebury, VT 05753
• 

  

  /51

  $620,000

  Sold Jul 31, 2025

  24 Oak Dr, Middlebury, VT 05753

  • 3 Beds
  • 2 Baths
  • 2,796 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $222/SF
  • 15 Days On Market

  Current Estimated Value $619,198

  Last Listing Agent Beth Stanway IPJ Real Estate

  24 Oak Dr, Middlebury, VT 05753
• 

  

  /29

  Est $610,233

  Not Listed For Sale

  21 Short Shannon St, Middlebury, VT 05753

  • 3 Beds
  • 1.5 Baths
  • 2,152 Sq Ft
  • Built 1940

  21 Short Shannon St, Middlebury, VT 05753

  Last Sold Summary

  • 29 Days On Market
• 

  

  /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
• 

  

  /60

  $1,510,000

  Sold Oct 29, 2025

  380 Foote Farm Rd, Middlebury, VT 05753

  • 4 Beds
  • 3.5 Baths
  • 3,599 Sq Ft
  • Built 2008

  Last Sold Summary

  • 12% Above List Price
  • $420/SF
  • 3 Days On Market

  Current Estimated Value $1,268,290

  Last Listing Agent Erin McCormick KW Vermont

  380 Foote Farm Rd, Middlebury, VT 05753
• 

  

  /20

  Est $441,163

  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
• 

  

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18