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Middlebury VT Real Estate

In the center of Addison County is the stunning college town of Middlebury, VT. Home of the historical Middlebury College and the Henry Sheldon Museum of Vermont History, Middlebury is the perfect dynamic of an old town that has been kept alive with modern technology. The town’s center hosts a variety of local restaurants, shops, and more. Bordered by the foothills of the Green Mountains and the Champlain Valley, Middlebury is a town filled with wonder and comfort. 

Search the latest real estate in Middlebury, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. Register to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

For more information, any questions you may have & to schedule a show, please feel free to give us a call or contact us online.

202 Weybridge Street Middlebury VT 05753

Middlebury, VT202 Weybridge Street

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4913422

  • Residential Single Family
  • Bathroom 4
  • Bedrooms 5
  • Construction Existing
  • Square Feet 5,000

Tastefully restored historic property located in Middlebury, Vermont. Surrounded by woods and Otter Creek, the one-acre property is quiet, private, and scenic, yet within walking distance of all that Middlebury's town and Middlebury College have to offer. Compound includes main house, attached barn and apartment, and a three-story “grainery” with office, guest space, and studio possibilities. The 1818 post and beam structure has been stripped bare to allow for new and proper insulation, wiring, plumbing, and heating. All finished surfaces are tasteful and high-quality. The main house has 2400 square feet, the attached apartment 1200, and the grainery 1500. In total, the property has 5000 square feet of interesting and elegant living space three blocks from downtown Middlebury and the heart of the Middlebury College campus. Several spaces, including the grainery, barn, and balcony, will be built to the needs and desires of the buyer. The property will be complete in August/ September 2022. More photos and information upon request.

Listed by Dave White of OwnerEntry.com

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

397 Weybridge Street Middlebury VT 05753

Middlebury, VT397 Weybridge Street

Price$675,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4896914

  • Residential Single Family
  • Bathroom 2
  • Square Feet 2,944
  • Construction Existing
  • Bedrooms 5

Let your imagination run wild! The opportunities here are endless, looking for a home to add your personal touches, or for land to build your own home, maybe even have a guest houses or two or just some additional elbow room. This 5 bedroom home offers spacious rooms, tall ceilings and over and acre and half of land. Views of the Green Mountains from the second story windows and also from the backyard. Attached two car garage, three season porch and tons of storage. Situated nicely off the street with sidewalks leading to downtown or the TAM for hiking. All this located in the heart of a small New England town! A home like this only comes on the market once in a lifetime!

Listed by Courtney Houston DeBisschop of IPJ Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2337 Rte 7 S Middlebury VT 05753

Middlebury, VT2337 Rte 7 S

Price$595,000The price has recently decreased

MLS Number 4916092

  • Commercial
  • Year Built 1920
  • Acreage 0.48

A rare opportunity to own a multi functional Middlebury residential and office building in exceptional condition. Two apartments and 5 offices fully rented plus a common reception area and a conference room for all tenants use. Many improvements including new architectural shingle roof in Oct of 2021 ( 30 year warranty), new gas furnace and two new Rinnai heaters in apartments, and change over to natural gas. The building has had new insulation and vinyl siding and all new insulated windows installed plus the chimney rebuilt, all new wiring and 200amp service, new roof on the garage and loft areas built for storage plus a small storage building for tenants was added. The driveway and yard were paved and other areas were landscaped. New porches and entry ways were built for all tenants (4 entrances ). Due to tenant privacy and confidentiality of tenants several of the photos attached were taken before current tenants moved in. Apartments are fully furnished as are most offices with the exception of several desks and electronic office equipment. Some owner financing may be possible. Rents may be augmented by rental of garage units. Tenants have indicated a desire to continue tenancy. This listing is broker owned.

Listed by George Brewer of BHHS Vermont Realty Group/Middlebury

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

426 East Main Street Middlebury VT 05753

Middlebury, VT426 East Main Street

Price$587,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4898955

  • Multifamily
  • Square Feet 2,304
  • Units 2
  • Bathroom 2
  • Acreage 0.24

Come see this very well-kept duplex that is partially being used as an Airbnb in a beautiful location along the Middlebury River. This duplex features an attached two car garage, off street parking with 2 driveways and solar panels installed on roof. The first-floor, recently updated unit, is light and bright and offers a lovely kitchen/dining room, laundry area and hardwood floors through most of the unit. The second-floor unit has hardwood floors through most of the unit, contains two bedrooms, a large open living room dining room area, an enclosed porch plus a deck with amazing views of the river. Soak in the views and sounds of the river as well as the beautiful gardens that have been professionally maintained. This property's location is not only beautiful but also convenient to Middlebury College, Middlebury Gorge, Snow Bowl Ski Area, Rikert Nordic Skiing and the iconic Waybury Inn from the Newhart show. Enjoy the natural wonders of Middlebury, skiing, snowshoeing, hiking, fishing and so much more.

Listed by Don Marcelino of The Marcelino Team

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

426 East Main Street Middlebury VT 05753

Middlebury, VT426 East Main Street

Price$587,000The price has recently decreased

MLS Number 4905354

  • Commercial
  • Year Built 1920
  • Acreage 0.24
  • NOI 43992

Come see this very well-kept duplex that is partially being used as an Airbnb in a beautiful location along the Middlebury River. This duplex features an attached two car garage, off street parking with 2 driveways and solar panels installed on roof. The first-floor, recently updated unit, is light and bright and offers a lovely kitchen/dining room, laundry area and hardwood floors through most of the unit. The second-floor unit has hardwood floors through most of the unit, contains two bedrooms, a large open living room dining room area, an enclosed porch plus a deck with amazing views of the river. Soak in the views and sounds of the river as well as the beautiful gardens that have been professionally maintained. This property's location is not only beautiful but also convenient to Middlebury College, Middlebury Gorge, Snow Bowl Ski Area, Rikert Nordic Skiing and the iconic Waybury Inn from the Newhart show. Enjoy the natural wonders of Middlebury, skiing, snowshoeing, hiking, fishing and so much more.

Listed by Don Marcelino of The Marcelino Team

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

317 Rolling Acres Circle Middlebury VT 05753

Middlebury, VT317 Rolling Acres Circle

Price$545,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4908978

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 2,237
  • Bathroom 2
  • Construction Existing

This charming cape has a lovely lot with ample open space, as well as a nice wooded area behind the house. There are large sun-filled living and dining spaces that flow very nicely into each other, as well as a beautifully updated efficient kitchen. There are 2 bedrooms on the first floor and another 2 on the second floor, and a full bath on both floors. There is hardwood and tile flooring throughout the house. The large mudroom that links the garage to the house also has the laundry area with a large laundry sink. The Owner is putting a new roof on the south side of the house in the next few weeks. This location is just minutes from town and is a nice blend of feeling you are in the country as well as a nice neighborhood.

Listed by Nancy Foster of Champlain Valley Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

72 Daisy Lane Middlebury VT 05753

Middlebury, VT72 Daisy Lane

Price$499,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4912369

  • Residential Single Family
  • Square Feet 2,318
  • Bathroom 3
  • Bedrooms 4
  • Construction Existing

The best of Both Worlds, this house offers country location but with the convenience of neighbors and one of the Town's Baseball diamonds! Nicely landscaped with a fire pit and new deck, enjoy the beautiful outdoors! Inside, this home is a treasure, with many recent updates, including most of the appliances with the kitchen as the gathering spot for everyone! The primary en suite bedroom is on the first floor and there is also a generous mudroom and laundry with 1/2 bath. Upstairs is a spacious family room, 3 more bedrooms and another full bath. An attached 2-car garage and full basement complete the package.

Listed by Bonnie Gridley and Cory Cheever of RE/MAX North Professionals,Middlebury

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Meadow Way Middlebury VT 05753

Middlebury, VT12 Meadow Way

Price$470,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4917165

  • Residential Single Family
  • Square Feet 1,672
  • Bathroom 2
  • Bedrooms 3
  • Construction Existing

Here's the home you've been waiting for and the opportunity to live in one of the most desirable neighborhoods in the heart of Middlebury. This home has been well maintained and is ready for you to move right in! The current owners have increased the functionality and living space with upgrades and improvements that you'll love. Adding a mudroom, essential for Vermont winters and active families, a family room that opens up the space for gathering with doors that open to a beautiful deck overlooking an expansive, yet private back yard! The home's kitchen is warm and inviting with beautiful tile details, cherry cabinets and granite countertops and island. A dining room and a large living room give you room for those times when you might seek separate spaces. Walk, roll, or ride to schools, restaurants, shopping, library, theaters and the Trail Around Middlebury. This home is a must-see!

Listed by Elizabeth Marino of BHHS Vermont Realty Group/Middlebury

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

305 Mead Lane Middlebury VT 05753

Middlebury, VT305 Mead Lane

Price$425,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4911841

  • Residential Single Family
  • Square Feet 2,160
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

On a quiet street surrounded by mature oaks and maples, this beautiful modern colonial salt box is in move-in condition. The craftsman kitchen leads right into an inviting formal dining room with cathedral ceilings and into a charming library with build-in bookshelves. The spacious, bright living room with rustic hardwood floors offers a cozy fireplace and sliding glass doors out to a large, wrap-around deck. Upstairs there are four rooms for your family and guests: three spacious bedrooms, a full bath, and a large master suite with two built-in closets and an en-suite bathroom of its own. A full-sized attic and semi-finished basement with an efficient Buderus furnace and a carpeted bonus room for your hobbies complete this lovely home. Only five minutes to town, this home is located on a bus route in the desirable Middlebury school district. Spectacular hiking opportunities right out the door (Abbey Pond Trail). Come and see this warm, functional, light-filled home with the character of a colonial estate in the countryside at the foot of the Green Mountains right outside of New England's most charming college town.(SHOWINGS BEGIN FRIDAY MAY 27th)

Listed by John Snyder-White of Champlain Valley Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

29 Court Street Middlebury VT 05753

Middlebury, VT29 Court Street

Price$425,000The price has recently decreased

MLS Number 4906282

  • Commercial
  • Year Built 1900
  • Acreage 0.39

Prominently located along a main road in the center of the college town of Middlebury, Vermont, this multi-unit building can provide many options. The building is currently set up with three units. A modest two-room (plus a 1/2 bath) unit at the back of the building, a main floor unit with 4 rooms and two 1/2 baths and a second floor unit with 4 rooms plus a kitchen and full bathroom in the original part of the main house/building. The two story section sits on a foundation with a basement that houses the utilities for that part of the building. The back unit has a propane heater and is currently separate from the rest. It could be all opened up quite easily if that is the need of the next owner. Plenty of parking behind the building and two Route 7 curb cuts on either side of the building. Exterior is in great shape, roof is slate, interior has been renovated over the years and is all ready to go. Be sure to check out the Virtual Tours (there are two, one for the main house, one for the ell in the back).

Listed by Amey Ryan of IPJ Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

34 School House Hill Road Middlebury VT 05740

Middlebury, VT34 School House Hill Road

Price$375,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4869892

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,480

Tucked away off the road is this beautifully remodeled 1950's 2 bedroom Ranch on 5.6 park-like acres. The property is private and secluded, but also convenient to shopping and schools. This cottage-like Ranch and attached 2 car garage features open living with cathedral ceilings, a Cooks Kitchen with restaurant style stainless steel kitchen sink/table, Living room, family room with wood stove for those chilly spring nights and a loft in the 2nd bedroom. Not much else to do but Move In and Enjoy! Security system is leased.

Listed by Bonnie Gridley of RE/MAX North Professionals,Middlebury

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1249 Cady Road Middlebury VT 05753

Middlebury, VT1249 Cady Road

Price$364,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4912014

  • Residential Single Family
  • Square Feet 2,525
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

This is an opportunity that you do not want to miss! This charming farmhouse is sited on a corner lot with 2 acres of land. Mature trees including fruit trees, provide a shaded area to have your summer gatherings outside. There is plenty of level lawn for gardens and recreation. The 3 bedroom home has been updated with a beautiful new kitchen and dining area complete with a live edge island and new stainless appliances. The entrance into a multi function "sun room" has been restored and is the perfect spot for toys or a quiet cup of coffee. This home exudes charm and character. There are 2 rooms that you can still put your creativity to work on. Only minutes to the center of Middlebury but you have the feel of living in the country. Delayed showing until 5/28/22.

Listed by Nancy Larrow of BHHS Vermont Realty Group/Vergennes

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.7% last updated on 2022-06-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 3, 2022.

 

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