3,201

Middlebury, VT Homes

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  • 220 Painter Hills Rd, Middlebury, VT 05753
    220 Painter Hills Rd, Middlebury, VT 05753
    220 Painter Hills Rd, Middlebury, VT 05753
    /49

    $549,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,480 Sq Ft

    220 Painter Hills Rd, Middlebury, VT 05753

    This is such a great location! Located close to town, this home is in a private setting with over one and a half acres of open yard and trees. Huge windows in the living room face the view of the mountains. A large deck with that same view is the perfect spot for morning coffee. The open concept living/dining/kitchen has a wood stove to keep things cozy in the colder months. The kitchen has

    Beth Stanway IPJ Real Estate

    220 Painter Hills Rd, Middlebury, VT 05753
  • 39 Otterside Ct N, Middlebury, VT 05753
    39 Otterside Ct N, Middlebury, VT 05753
    39 Otterside Ct N, Middlebury, VT 05753
    /25

    $1,500 per month

    Otterside Apartments

    2 Beds

    39 Otterside Ct N, Middlebury, VT 05753

    Otterside Apartments is located in beautiful Middlebury, Vermont. Seeped in history, Middlebury was chartered in 1761 and was settled just after the Revolutionary War. Today, the village is listed on the National Register of Historic Places and is home to approximately 8,200 residents in addition to Middlebury College.

    39 Otterside Ct N, Middlebury, VT 05753
  • 7 High St, Middlebury, VT 05753
    7 High St, Middlebury, VT 05753
    7 High St, Middlebury, VT 05753
    /34

    $578,000 Sold Oct 02, 2025

    • 1,516 Sq Ft
    • $381/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1850

    7 High St, Middlebury, VT 05753

    A lovingly renovated Middlebury village cottage just steps from shops, the library, and Middlebury College—where timeless charm meets your next chapter. Updated from basement to roof by Addison County craftsmen, the home blends historic character with thoughtful modern improvements. Hickory floors flow through the living spaces, anchored by a gas fireplace for warmth and charm. The farmhouse

    Deborah Hillman BHHS Vermont Realty Group/Middlebury

    7 High St, Middlebury, VT 05753
    • 6 Nedde Ln, Middlebury, VT 05753
      6 Nedde Ln, Middlebury, VT 05753
      6 Nedde Ln, Middlebury, VT 05753
      /29

      Est $641,976 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,810 Sq Ft

      6 Nedde Ln, Middlebury, VT 05753

      6 Nedde Ln, Middlebury, VT 05753
  • 380 Foote Farm Rd, Middlebury, VT 05753
    380 Foote Farm Rd, Middlebury, VT 05753
    380 Foote Farm Rd, Middlebury, VT 05753
    /60

    $1,350,000 Pending

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

    380 Foote Farm Rd, Middlebury, VT 05753

    First time on the market, this architect-designed and custom-built home in the Foote Farm community exudes timeless Vermont charm. Sitting on 1.21 private acres with the option to expand with an adjacent 1.3 acre lot, the Greek Revival-styled modern farmhouse is nestled into a wooded hillside and overlooks 112 acres of permanent greenspace, just 3.5 miles to Middlebury. The open concept kitchen,

    Erin McCormick KW Vermont

    380 Foote Farm Rd, Middlebury, VT 05753
  • 45 Court St Unit A, Middlebury, VT 05753
    45 Court St Unit A, Middlebury, VT 05753
    45 Court St Unit A, Middlebury, VT 05753
    /21

    $2,500 per month

    • 2 Beds
    • 1 Bath
    • 1,595 Sq Ft
    • Apartment for Rent

    45 Court St Unit A, Middlebury, VT 05753

    Spacious downtown 2-Bedroom Apartment w/bonus room.Are you looking for a cozy and convenient place to call home in historic Middlebury? Look no further! This second-floor, 2-bedroom, 1-bath apartment is waiting for you at 45 Court.(across from Kinney Drugs).Located in the heart of Middlebury, you're just a short walk away from the vibrant downtown scene. Enjoy local shops, restaurants,

    Ray Fortier KW Vermont

    45 Court St Unit A, Middlebury, VT 05753
  • 385 E Main St, Middlebury, VT 05753
    385 E Main St, Middlebury, VT 05753
    385 E Main St, Middlebury, VT 05753
    /26

    $399,000 Sold Oct 02, 2025

    • 1,206 Sq Ft
    • $331/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    385 E Main St, Middlebury, VT 05753

    This circa-1900 farmhouse was lovingly restored by a previous owner. Quality materials & craftsmanship like the restored staircase, fir side-entry door, maple cabinetry & wood floors enhance charming historic details throughout, including low windows, wrap-around porch, and original floors. Quality vinyl siding, energy-efficient windows, newer chimneys and roofs, and well-maintained systems make

    Sarah Peluso IPJ Real Estate

    385 E Main St, Middlebury, VT 05753
    • 51 Seminary Street Extension, Middlebury, VT 05753
      51 Seminary Street Extension, Middlebury, VT 05753
      51 Seminary Street Extension, Middlebury, VT 05753
      /28

      Not Listed For Sale

      • 9 Beds
      • 2.5 Baths
      • 5,428 Sq Ft

      51 Seminary Street Extension, Middlebury, VT 05753

      51 Seminary Street Extension, Middlebury, VT 05753
  • 530 Halpin Rd, Middlebury, VT 05753
    530 Halpin Rd, Middlebury, VT 05753
    530 Halpin Rd, Middlebury, VT 05753
    /38

    $779,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,928 Sq Ft

    530 Halpin Rd, Middlebury, VT 05753

    This house has a flexible floor plan, with bedroom options on all three levels. On the main level, the kitchen/dining area opens to a large living room with built in bookcases and maple floors. The new kitchen has beautiful wood cabinets, granite counter tops and stainless appliances. A gas fireplace creates a warm hearth in the main living area and glass doors lead out to the upper deck. Tons of

    Beth Stanway IPJ Real Estate

    530 Halpin Rd, Middlebury, VT 05753
  • 45 Bakery Ln, Middlebury, VT 05753
    45 Bakery Ln, Middlebury, VT 05753
    45 Bakery Ln, Middlebury, VT 05753
    /19

    $3,300 per month

    • 3 Beds
    • 1.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    45 Bakery Ln, Middlebury, VT 05753

    Welcome to The Annex, a charming three-bedroom, two-bathroom guest house in the heart of Middlebury, Vermont. This exceptional property offers a central location, within walking distance to downtown, Middlebury College, Porter hospital, and restaurants. Situated on a private 1.3-acre estate next to the owner's historic brick colonial, The Annex provides a tranquil living experience with a

    Ray Fortier KW Vermont

    45 Bakery Ln, Middlebury, VT 05753
  • 1 Overbrook Dr, Middlebury, VT 05753
    1 Overbrook Dr, Middlebury, VT 05753
    1 Overbrook Dr, Middlebury, VT 05753
    /36

    $379,000 Sold Sep 30, 2025

    • 1,008 Sq Ft
    • $376/SF
    • 7 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1988

    1 Overbrook Dr, Middlebury, VT 05753

    LIGHT & BRIGHT SINGLE LEVEL END UNIT IN A DESIRABLE MIDDLEBURY CONDOMINIUM NEIGHBORHOOD! Inviting spacious first floor end unit combines a generous kitchen, with lots of counter and cupboards, with the open sunlit living/dining room. Sliders, with interior pocket doors, open to a pleasant deck. Perfect for that morning cup of coffee or grilling dinner. Two first floor bedrooms, large bath, first

    Sue Mackey BHHS Vermont Realty Group/Middlebury

    1 Overbrook Dr, Middlebury, VT 05753
    • 9 Woodbridge Ln, Middlebury, VT 05753
      9 Woodbridge Ln, Middlebury, VT 05753
      9 Woodbridge Ln, Middlebury, VT 05753
      /15

      Est $221,779 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,080 Sq Ft

      9 Woodbridge Ln, Middlebury, VT 05753

      9 Woodbridge Ln, Middlebury, VT 05753
  • 68 Otterside Ct, Middlebury, VT 05753
    68 Otterside Ct, Middlebury, VT 05753
    68 Otterside Ct, Middlebury, VT 05753
    /29

    $285,000 Under Contract

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

    68 Otterside Ct, Middlebury, VT 05753

    This 2-bedroom, 1.5 bath townhouse-style condo offers the convenience of condo living with a desirable, and private end-unit location. Community amenities include an outdoor pool and an assigned carport with storage. Entering through a small foyer (with a coat closet and access to the unit’s utilities) the space flows directly into the tasteful, eat-in kitchen. One will begin to appreciate the

    Jill Fraga The Real Estate Company of Vermont, LLC

    68 Otterside Ct, Middlebury, VT 05753
  • 487 Burnham Dr, Middlebury, VT 05753
    487 Burnham Dr, Middlebury, VT 05753
    487 Burnham Dr, Middlebury, VT 05753
    /32

    $625,000 Sold Sep 30, 2025

    • 2,411 Sq Ft
    • $259/SF
    • 28 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    487 Burnham Dr, Middlebury, VT 05753

    Delightful and cheery, this cape style home in "The Woodlands" has an ideal layout with wonderful flow. With all the spaces you need on the main living level including a home office, mudroom entryway, family room, living room, dining room, renovated kitchen, laundry and the primary bedroom suite (with a private full bath and a walk in closet) PLUS the screened porch allowing you to enjoy the

    Amey Ryan IPJ Real Estate

    487 Burnham Dr, Middlebury, VT 05753
    • 85 Court St, Middlebury, VT 05753
      85 Court St, Middlebury, VT 05753
      85 Court St, Middlebury, VT 05753
      /30

      Est $357,757 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,830 Sq Ft

      85 Court St, Middlebury, VT 05753

      85 Court St, Middlebury, VT 05753
  • 573 S Munger St, Middlebury, VT 05753
    573 S Munger St, Middlebury, VT 05753
    573 S Munger St, Middlebury, VT 05753
    /39

    $699,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,357 Sq Ft

    573 S Munger St, Middlebury, VT 05753

    What a spot! Located on a dead end road just three miles from town, with beautiful Green Mountain views out your back door! Drive up and you will appreciate the extensive stone landscaping in the front of the home- creating a welcoming entrance. Perennials are in bloom all around. From the mudroom entry, a living and dining, open concept space features newly refinished wood floors. The kitchen

    Sarah Peluso IPJ Real Estate

    573 S Munger St, Middlebury, VT 05753
  • 11 Woodbridge Ln, Middlebury, VT 05753
    11 Woodbridge Ln, Middlebury, VT 05753
    11 Woodbridge Ln, Middlebury, VT 05753
    /37

    $232,000 Sold Sep 26, 2025

    • 1,122 Sq Ft
    • $207/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    11 Woodbridge Ln, Middlebury, VT 05753

    The Summer of 2025 in Vermont... Welcome to Middlebury and this totally renovated 2 bedroom, 1 bath townhome. Fresh, modern and contemporary finishes come to mind upon entering this unit. You would never know the townhome was tenant occupied with pride of ownership still beaming throughout. Features include: LVP flooring throughout, fresh colors, an open kitchen with loads of cabinetry and an

    The Signature Realty Group Signature Properties of Vermont

    11 Woodbridge Ln, Middlebury, VT 05753
    • 78 Ossie Rd, Middlebury, VT 05753
      78 Ossie Rd, Middlebury, VT 05753
      78 Ossie Rd, Middlebury, VT 05753
      /40

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,195 Sq Ft

      78 Ossie Rd, Middlebury, VT 05753

      78 Ossie Rd, Middlebury, VT 05753
  • 30 South St, Middlebury, VT 05753
    30 South St, Middlebury, VT 05753
    30 South St, Middlebury, VT 05753
    /27

    $695,000

    • 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. From the front door you enter into the living room space, with wood floors that continue throughout the home. A pellet stove heats the home, and built in

    Sarah Peluso IPJ Real Estate

    30 South St, Middlebury, VT 05753
  • 719 Washington Street Extension, Middlebury, VT 05753
    719 Washington Street Extension, Middlebury, VT 05753
    719 Washington Street Extension, Middlebury, VT 05753
    /51

    $650,000 Sold Sep 24, 2025

    • 2,930 Sq Ft
    • $222/SF
    • 68 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1880

    719 Washington Street Extension, Middlebury, VT 05753

    THIS HOME WILL BE FRESHLY PAINTED ON THE EXTERIOR PRIOR TO CLOSING! This historical home is located on three lovely acres of land, just over a mile from downtown Middlebury! A circular drive greets you as you drive to the home, and the three bay detached garage offers room for vehicles and equipment! Enter in and find a renovated kitchen, with quartz countertops and stainless steel appliances. A

    Sarah Peluso IPJ Real Estate

    719 Washington Street Extension, Middlebury, VT 05753
    • 131 Lindale Cir, Middlebury, VT 05753
      131 Lindale Cir, Middlebury, VT 05753
      131 Lindale Cir, Middlebury, VT 05753
      /16

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,064 Sq Ft

      131 Lindale Cir, Middlebury, VT 05753

      131 Lindale Cir, Middlebury, VT 05753
  • 205 Cedar Ridge Dr, Middlebury, VT 05753
    205 Cedar Ridge Dr, Middlebury, VT 05753
    205 Cedar Ridge Dr, Middlebury, VT 05753
    /45

    $494,700

    • 2 Beds
    • 2 Baths
    • 2,114 Sq Ft

    205 Cedar Ridge Dr, Middlebury, VT 05753

    Tucked in at the end of a shared/private roadway is this chalet-style, post and beam house with lovely exposed beams, large and open spaces and a fabulous deck! Pine boards grace the floors of this home giving it a warm and inviting feeling along with a little bit of rustic charm. Constructed with stress skin panels, well-placed windows and a centrally located wood stove this 1977 house is

    Amey Ryan IPJ Real Estate

    205 Cedar Ridge Dr, Middlebury, VT 05753
  • 55 Ossie Rd, Middlebury, VT 05753
    55 Ossie Rd, Middlebury, VT 05753
    55 Ossie Rd, Middlebury, VT 05753
    /22

    $240,000 Sold Sep 19, 2025

    • 1,068 Sq Ft
    • $225/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    55 Ossie Rd, Middlebury, VT 05753

    Affordable Living in a Prime Middlebury Location! A well-maintained 2001 Redman single-wide home featuring a cozy 12x12 four-season sunroom—perfect for relaxing year-round. Enjoy the convenience of a detached one-car garage with automatic door opener, plus an additional outbuilding ideal for hobbies, gardening, or extra storage. Nestled on a spacious .39-acre lot, this property offers privacy and

    Roxanna Emilo Emilo Real Estate, LLC

    55 Ossie Rd, Middlebury, VT 05753
    • 19 N Bingham St, Middlebury, VT 05753
      19 N Bingham St, Middlebury, VT 05753
      19 N Bingham St, Middlebury, VT 05753
      /30

      Est $697,402 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 2,172 Sq Ft

      19 N Bingham St, Middlebury, VT 05753

      19 N Bingham St, Middlebury, VT 05753
  • 1691 N Bingham St, Middlebury, VT 05753
    1691 N Bingham St, Middlebury, VT 05753
    1691 N Bingham St, Middlebury, VT 05753
    /53

    $1,495,000

    • 5 Beds
    • 4.5 Baths
    • 3,571 Sq Ft

    1691 N Bingham St, Middlebury, VT 05753

    A rare opportunity to enter the next phase of life on this estate-like property in Cornwall. With incredible westerly views across fields, the Lemon Fair and out to the Adirondack High Peaks, the location will simply take your breath away. The original house has been transformed over the years with an eye towards entertaining and allowing for spacious rooms and great lines of sight as two houses

    Amey Ryan IPJ Real Estate

    1691 N Bingham St, Middlebury, VT 05753
  • 62 Court St, Middlebury, VT 05753
    62 Court St, Middlebury, VT 05753
    62 Court St, Middlebury, VT 05753
    /42

    $420,000 Sold Sep 12, 2025

    • 2,352 Sq Ft
    • $179/SF
    • 15 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1900

    62 Court St, Middlebury, VT 05753

    Close to town - check! Income generating - check! Plenty of parking - check! Versatile building - check! Relatively easy maintenance - check! This three unit investment property cash flows with the current rents and there is potential to expand on this property and create more housing units. The 1/2 acre, in town, lot is in the Residential 12 zoning district and could likely accommodate another

    Amey Ryan IPJ Real Estate

    62 Court St, Middlebury, VT 05753
    • 23 Woodbridge Ln, Middlebury, VT 05753
      23 Woodbridge Ln, Middlebury, VT 05753
      23 Woodbridge Ln, Middlebury, VT 05753
      /25

      Est $219,492 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,122 Sq Ft

      23 Woodbridge Ln, Middlebury, VT 05753

      23 Woodbridge Ln, Middlebury, VT 05753
  • 417 Painter Rd, Middlebury, VT 05753
    417 Painter Rd, Middlebury, VT 05753
    417 Painter Rd, Middlebury, VT 05753
    /60

    $637,000

    • 4 Beds
    • 3 Baths
    • 2,906 Sq Ft

    417 Painter Rd, Middlebury, VT 05753

    Tucked behind a large hedgerow with 12+ acres of land to play and explore on, this sprawling house has a place and space for everyone! On the main level, enter into the large tiled mudroom (with hooks and cubbies and a closet). Come a bit further and you'll find a comfortable den area just before you reach the kitchen/dining room with a center island, woodstove and tons of bookshelves. A few

    Amey Ryan IPJ Real Estate

    417 Painter Rd, Middlebury, VT 05753
  • 76 Lindale Cir, Middlebury, VT 05753
    76 Lindale Cir, Middlebury, VT 05753
    76 Lindale Cir, Middlebury, VT 05753
    /24

    $75,000 Sold Sep 10, 2025

    • 720 Sq Ft
    • $104/SF
    • 2 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1970

    76 Lindale Cir, Middlebury, VT 05753

    Affordable living! 2 bedroom, 1 1/2 bath mobile home on a sweet lot in Lindale Park. 10 x 26 three season porch, 10 x 10 shed and a nice 30 x 30 fenced in garden space. Handicapped accessible ramp. This home had been completely redone from the studs up, added insulation, replacement windows, and doors, new wiring, new 100 amp. Breaker box, all new interior 2 x 4 stud walls, 1/2 " sheetrock

    Roxanna Emilo Emilo Real Estate, LLC

    76 Lindale Cir, Middlebury, VT 05753
    • 1903 Quaker Village Rd, Middlebury, VT 05753
      1903 Quaker Village Rd, Middlebury, VT 05753
      1903 Quaker Village Rd, Middlebury, VT 05753
      /40

      Est $422,504 Not Listed For Sale

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

      1903 Quaker Village Rd, Middlebury, VT 05753

      1903 Quaker Village Rd, Middlebury, VT 05753
  • 30 Mountain View Ln, Middlebury, VT 05753
    30 Mountain View Ln, Middlebury, VT 05753
    30 Mountain View Ln, Middlebury, VT 05753
    /38

    $525,000

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

    30 Mountain View Ln, Middlebury, VT 05753

    Great house on a corner lot in a Middlebury neighborhood that's close to town! The first floor has well equipped kitchen with a large copper topped island and a spacious dining area that's perfect for entertaining. The living room opens to a bonus area that could be a den, office, playroom, etc... There is a first floor bedroom and a full bath with laundry. Upstairs you will find a primary suite

    Beth Stanway IPJ Real Estate

    30 Mountain View Ln, Middlebury, VT 05753
  • 33 Stonecrop Rd, Middlebury, VT 05753
    33 Stonecrop Rd, Middlebury, VT 05753
    33 Stonecrop Rd, Middlebury, VT 05753
    /9

    $525,000 Sold Sep 04, 2025

    • 2,019 Sq Ft
    • $260/SF
    • 15 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    33 Stonecrop Rd, 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, end unit townhome will be ready for occupancy in the summer of 2025. To be built with energy efficiency at

    Sarah Peluso IPJ Real Estate

    33 Stonecrop Rd, Middlebury, VT 05753
    • 156 Terrace Heights, Middlebury, VT 05753
      156 Terrace Heights, Middlebury, VT 05753
      156 Terrace Heights, Middlebury, VT 05753
      /32

      Est $444,439 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,060 Sq Ft

      156 Terrace Heights, Middlebury, VT 05753

      156 Terrace Heights, Middlebury, VT 05753
  • 118 Three Mile Bridge Rd, Middlebury, VT 05753
    118 Three Mile Bridge Rd, Middlebury, VT 05753
    118 Three Mile Bridge Rd, Middlebury, VT 05753
    /32

    $389,000

    • 3 Beds
    • 2 Baths
    • 2,232 Sq Ft

    118 Three Mile Bridge Rd, Middlebury, VT 05753

    This classic 1820 colonial blends historical charm with everyday practicality on a level one acre lot, featuring a welcoming circular driveway, an expansive garage, and a spacious barn. The home’s remodeled kitchen is a cook's delight, outfitted with modern appliances, ample cabinetry, and generous counter space; ideal for family gatherings or daily meal prep. The first floor offers two generous

    Levi Doria IPJ Real Estate

    118 Three Mile Bridge Rd, Middlebury, VT 05753
  • 249 Fields Rd, Middlebury, VT 05753
    249 Fields Rd, Middlebury, VT 05753
    249 Fields Rd, Middlebury, VT 05753
    /36

    $549,000 Sold Aug 29, 2025

    • 1,695 Sq Ft
    • $324/SF
    • 2 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    249 Fields Rd, Middlebury, VT 05753

    Welcome to this beautifully crafted, 3-bedroom, 3-bath single-family home nestled in one of Middlebury's most sought-after neighborhoods. Built in 2016, this move-in ready gem offers a perfect blend of comfort, style, and energy efficiency. Step inside to an open floor plan featuring hardwood floors, 9' ceilings, and sun-filled spaces throughout. The gourmet kitchen is a chef's dream with granite

    Michael Johnston Coldwell Banker Hickok and Boardman

    249 Fields Rd, Middlebury, VT 05753
    • 640 Sheep Farm Rd, Middlebury, VT 05753
      640 Sheep Farm Rd, Middlebury, VT 05753
      640 Sheep Farm Rd, Middlebury, VT 05753
      /40

      Est $655,654 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,240 Sq Ft

      640 Sheep Farm Rd, Middlebury, VT 05753

      640 Sheep Farm Rd, Middlebury, VT 05753
  • 427 E Main St, Middlebury, VT 05753
    427 E Main St, Middlebury, VT 05753
    427 E Main St, Middlebury, VT 05753
    /42

    $469,000

    • 5 Beds
    • 2 Baths
    • 2,963 Sq Ft

    427 E Main St, Middlebury, VT 05753

    Situated in the heart of East Middlebury, this farmhouse built in 1800 offers nearly 3,000 square feet of living space and features five bedrooms on a spacious 0.53-acre corner lot. The sizeable kitchen, with woodstove and attached breakfast nook, provides ample space for entertaining or simply whipping up meals. Adjacent to the kitchen, a newly remodeled utility room and bath with a tiled

    Levi Doria IPJ Real Estate

    427 E Main St, Middlebury, VT 05753
  • 800 Route 7 S, Middlebury, VT 05753
    800 Route 7 S, Middlebury, VT 05753
    800 Route 7 S, Middlebury, VT 05753
    /46

    $345,500 Sold Aug 29, 2025

    • 2,300 Sq Ft
    • $150/SF
    • 30 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    800 Route 7 S, Middlebury, VT 05753

    FLEXIBLE ZONING, MIXED USE ALLOWING FOR BOTH RESIDENTIAL OR COMMERCIAL OPPORTUNITY. Welcome to this charming 3-bedroom, 1.5-bathroom split-level home in the heart of Middlebury, VT. Set in a peaceful neighborhood surrounded by trees and well-spaced homes, this property offers both privacy and convenience. Step onto the inviting covered front porch and make your way inside to a cozy living room

    Connor Johnson KW Vermont

    800 Route 7 S, Middlebury, VT 05753
    • 706 Perkins Rd, Middlebury, VT 05753
      706 Perkins Rd, Middlebury, VT 05753
      706 Perkins Rd, Middlebury, VT 05753
      /29

      Est $437,576 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft

      706 Perkins Rd, Middlebury, VT 05753

      706 Perkins Rd, Middlebury, VT 05753
  • 44 Merchants Row, Middlebury, VT 05753
    44 Merchants Row, Middlebury, VT 05753
    44 Merchants Row, Middlebury, VT 05753
    /42

    $1,350,000

    • 4 Beds
    • 6 Baths
    • 4,716 Sq Ft

    44 Merchants Row, Middlebury, VT 05753

    A versatile residential and commercial property right in downtown Middlebury with great views of both the town green and river for someone who wants convenient downtown living and working, while earning income from additional apartments and small businesses! The owners did major renovations on the entire building including all new wiring, plumbing, new natural gas heating system, new roof, and

    Sarah Peluso IPJ Real Estate

    44 Merchants Row, Middlebury, VT 05753

Showing Results 1 - 40, Page 1 of 18

Vermont Addison County Middlebury

Real Estate & Homes

Home Trends in Middlebury, VT

On average, homes in Middlebury, VT sell after 36 days on the market compared to the national average of 52 days. The median sale price for homes in Middlebury, VT over the last 12 months is $435,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$435,000
Median Single Family Sale Price
$485,000
Median Townhouse Sale Price
$425,000
Median 2 Bedroom Sale Price
$349,500
Average Price Per Sq Ft
$293
Number of Homes for Sale
20
Last 12 months Home Sales
61
Months of Supply
3.90
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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