3,152

Middlebury, VT Homes

Section Image
  • /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
    • /33

      Est $713,309

      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

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • /7

    $130,000

    $20K PRICE DROP
    • Land
    • 23,522 Sq Ft
    • $240,741 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
  • /30

    $262,500

    Sold Aug 18, 2026

    7 Evergreen Ln, Middlebury, VT 05753

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1981

    Last Sold Summary

    • 12% Below List Price
    • $182/SF
    • 39 Days On Market

    Last Listing Agent Amey Ryan IPJ Real Estate

    7 Evergreen Ln, Middlebury, VT 05753
    • /27

      Est $348,606

      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

      Last Listing Agent Lisa Marie Sargent Champlain Valley Properties

  • /26

    $489,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,933 Sq Ft

    149 Rogers Rd, Middlebury, VT 05753

    Charming 3-bedroom home with a NEW roof located in Middlebury. This well-maintained property is both bright and functional with a layout that has comfortable living spaces, good-sized bedrooms, storage and even a bonus room. The sunny level backyard is perfect for gardening, outdoor play and entertaining. There is also a handy shed for your lawn equipment or extra storage. Located close to

    Heather Foster-Provencher Champlain Valley Properties

    149 Rogers Rd, Middlebury, VT 05753
  • /3

    $140,000

    Sold Aug 04, 2026

    TBD Middle Rd N, Middlebury, VT 05753

    • Land
    • 21,344 Sq Ft
    • $285,714 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 212 Days On Market

    Last Listing Agent Beth Stanway IPJ Real Estate

    TBD Middle Rd N, Middlebury, VT 05753
    • /37

      Est $712,300

      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

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • /32

    $279,000

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    36 Seymour St Unit 1, Middlebury, VT 05753

    Welcome to 36 Seymour Street, Unit 1, a charming first floor 2-bedroom, 1-bath condo offering 1,024 square feet of comfortable living space in a convenient Middlebury location. Inside, you'll find a functional layout with a spacious kitchen and dining area, hardwood and tile flooring, and the added convenience of first-floor laundry. Two well-sized bedrooms provide flexibility for everyday

    Christopher Williams Flex Realty

    36 Seymour St Unit 1, 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 $290,952

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

    68 Otterside Ct, Middlebury, VT 05753
    • /49

      Est $769,290

      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

      Last Listing Agent Amey Ryan IPJ Real Estate

  • /7

    $225,000

    • 2,088 Sq Ft

    51 Ossie Rd, Middlebury, VT 05753

    Exceptional redevelopment opportunity in East Middlebury for either commercial or residential uses.Bring your vision to life at 51 Ossie Road, a unique property with a long-standing history as the home of Otter East Bakery. For decades, this well-known location served as a successful food production facility, making it an excellent opportunity for entrepreneurs, investors, or business

    Duncan Harris The Kingsland Company

    51 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 $558,450

    Last Listing Agent Sarah Peluso IPJ Real Estate

    394 Cider Mill Rd, Middlebury, VT 05753
    • /49

      Est $1,183,523

      Not Listed For Sale

      3 Chipman Heights, Middlebury, VT 05753

      • 4 Beds
      • 3.5 Baths
      • 2,615 Sq Ft
      • Built 1976
      3 Chipman Heights, Middlebury, VT 05753

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Beth Stanway IPJ Real Estate

  • /46

    $549,000

    • 4 Beds
    • 2 Baths
    • 1,992 Sq Ft

    160 Mead Ln, Middlebury, VT 05753

    This 4 bedroom, 2 bath cape is tucked into a nice, quiet Middlebury neighborhood. It's been lovingly cared for by the same family since the beginning, with many upgrades over the years including a huge primary suite over the garage. The upstairs bedrooms are all spacious and inviting, with an additional bedroom on the 1st floor. The briight living room is open to the dining room, with a glass

    Ivy Naef McEntee The Next Chapter Real Estate LLC

    160 Mead Ln, Middlebury, VT 05753
  • /27

    $470,000

    Sold Aug 25, 2026

    30 South St, Middlebury, VT 05753

    • 4 Beds
    • 2 Baths
    • 2,037 Sq Ft
    • Built 1822

    Last Sold Summary

    • 32% Below List Price
    • $231/SF
    • 300 Days On Market

    Current Estimated Value $562,057

    Last Listing Agent Sarah Peluso IPJ Real Estate

    30 South St, Middlebury, VT 05753
    • /24

      Est $315,838

      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

      Last Listing Agent Beth Stanway IPJ Real Estate

  • /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
  • /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
    • /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

  • /31

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    4799 Route 30, Middlebury, VT 05753

    Welcome to this charming Cape style home, situated on just over 4 acres offering plenty of space, privacy, and room to enjoy the outdoors. The first floor features a comfortable bedroom, full bathroom, spacious kitchen and dining area, and a large living room perfect for relaxing or entertaining. Just off the dining area, step outside onto the back porch, complete with an awning for added shade

    Hughes Group Team Casella Real Estate

    4799 Route 30, 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
    • /28

      Est $362,077

      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

      Last Listing Agent Amey Ryan IPJ Real Estate

  • /48

    $499,000

    $50K PRICE DROP
    • 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
  • /13

    $390,000

    Sold Aug 11, 2026

    54 Court St, Middlebury, VT 05753

    • 1,872 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $386,652

    Last Listing Agent k. Cory Foote BHHS Vermont Realty Group/Vergennes

    54 Court St, Middlebury, VT 05753
    • /40

      Est $927,330

      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

      Last Listing Agent Amey Ryan IPJ Real Estate

  • /21

    $187,000

    $12K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    3 Woodbridge Ln Unit 3, Middlebury, VT 05753

    OPPORTUNITY IS KNOCKING! With a little sweat equity, you can unlock the potential of this 2 bedroom, 2 bath condo being sold in an estate sale "As Is." The home features two generously sized bedrooms, a comfortable living room, and a kitchen with an island that overlooks the dining area and opens to the deck. A walk-in pantry, half bath down, and full bath up add convenience. The laundry room is

    Sue Mackey BHHS Vermont Realty Group/Middlebury

    3 Woodbridge Ln Unit 3, Middlebury, VT 05753
  • /6

    $199,000

    Sold Aug 17, 2026

    376 S Ridge Dr, Middlebury, VT 05753

    • Land
    • 26,136 Sq Ft
    • $331,667 per Acre

    Last Sold Summary

    • 240 Days On Market

    Last Listing Agent Sarah Peluso IPJ Real Estate

    376 S Ridge Dr, Middlebury, VT 05753
    • /8

      Est $253,396

      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

      Last Listing Agent k. Cory Foote BHHS Vermont Realty Group/Vergennes

  • /30

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    76 N Forty Ln, Middlebury, VT 05753

    Welcome to this well-maintained home offering comfortable one-level living on 1.4 wooded acres in a peaceful country setting. With over 1,800 square feet of living space, this 3-bedroom, 2-bath home features a spacious layout with generously sized rooms and plenty of opportunity to make it your own. The primary suite offers a private bath and ample closet space, while the additional bedrooms

    Brittanie Caggige Vermont Real Estate Company

    76 N Forty Ln, 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 $683,639

    Last Listing Agent Sarah Peluso IPJ Real Estate

    371 Weybridge St, 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

      Last Listing Agent Irene Poole Coldwell Banker Hickok and Boardman

  • /11

    $295,000

    • Land
    • 4.5 Acres
    • $65,556 per Acre

    TBD Route 7 N, Middlebury, VT 05753

    A rare opportunity to own 4.5± acres of developable land within the Town of Middlebury. This parcel offers an excellent blend of convenience, flexibility, and future potential. Not only are the utilities either at the road or already on the property but there are views to the West. This property has a strong foundation for a variety of residential development visions.

    Heather Foster-Provencher Champlain Valley Properties

    TBD Route 7 N, Middlebury, VT 05753
  • /8

    $510,000

    Sold Aug 07, 2026

    54 Brush Ln Unit 8.4B, Middlebury, VT 05753

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

    Last Sold Summary

    • 6% Above List Price
    • $307/SF
    • 253 Days On Market

    Last Listing Agent Sarah Peluso IPJ Real Estate

    54 Brush Ln Unit 8.4B, Middlebury, VT 05753
    • /27

      Est $436,622

      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

      Last Listing Agent Sarah Peluso IPJ Real Estate

  • /7

    $130,000

    $20K PRICE DROP
    • Land
    • 22,651 Sq Ft
    • $250,000 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
  • /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
    • /29

      Est $584,476

      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

      Last Listing Agent Amey Ryan IPJ Real Estate

  • /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
  • /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

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home