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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.

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5 Court Street Middlebury VT 05753

Middlebury, VT5 Court Street

Price$1,150,000The price has recently decreased

MLS Number 4922137

  • Commercial
  • Year Built 1880
  • Square Feet 11,074
  • Acreage 0.1

A prominent feature in downtown Middlebury since 1814, this structure was the replacement of the original courthouse in this location, and built in 1883.To quote Glen Andres in the Walking Tour of Middlebury, "This replacement, by Clinton Smith of Middlebury, was described in the Middlebury Register in 1883 as of "mixed architecture with Queen Anne features,"and declared the handsomest courthouse in the state. The facade is both picturesque and ordered. Its asymmetric massing and variety of detail in stone, brick, wood, slate, and glazing are held in line by articulating brick panels and "structure."This was very up-to-date design for Vermont. The panel-brick style (as it since has been dubbed) was just being popularized by leading architects in Boston, New York, and Philadelphia. Yet the courthouse is hardly a pure import. Its architect was local, and he has put the stamp of his personality and craftsmanship on its design. He also has maintained a sensitivity to its setting. Vigorous in its detail, the 1883 courthouse remains a good neighbor to the earlier structures on Court Square, prominent, but not too assertive for the good of its surroundings." Currently used for office space, many of the original architectural details are intact! The property includes an elevator, and is fully up to date with fire safety including a sprinkler system.Three floors of office space, and a full basement that has plenty of storage, and all the mechanicals. Own a piece of Middlebury history!

Listed by Sarah Peluso 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: 6.49% last updated on 2022-12-01

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

19 Chipman Heights Middlebury VT 05753

Middlebury, VT19 Chipman Heights

Price$588,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4921955

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,600
  • Construction Existing

The charming home is in one of the best locations in the town of Middlebury! It is both in a neighborhood, and is very private with a partially wooded .9 acre lot with access to walking trails on town owned land. There are beautiful long-range views in the winter when the leaves are off the trees. The house has been very nicely updated with replacement windows and exterior doors, new and/or refinished floors, new decks, nicely updated bathrooms, new appliances, insulated basement and other improvements that you need to see for yourself. This 4 bedroom, 3 bath home is both spacious and cozy. Easy access to stores, schools, and to all that Middlebury has to offer!

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: 6.49% last updated on 2022-12-01

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$567,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4898955

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

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: 6.49% last updated on 2022-12-01

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$567,000The price has recently decreased

MLS Number 4905354

  • Commercial
  • Square Feet 2,904
  • 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: 6.49% last updated on 2022-12-01

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$525,000The price has recently decreased

MLS Number 4916092

  • Commercial
  • Year Built 1920
  • Square Feet 2,556
  • 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

{$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: 6.49% last updated on 2022-12-01

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$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4921934

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,556
  • Bedrooms 2
  • Bathroom 2

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

{$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: 6.49% last updated on 2022-12-01

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

51 Seminary Street Middlebury VT 05753

Middlebury, VT51 Seminary Street

Price$495,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4933111

  • Residential Single Family
  • Square Feet 5,428
  • Bedrooms 9
  • Bathroom 3
  • Construction Existing

"Among the architectural landmarks of Middlebury, VT stands the imposing Federal style house, Stonecrop Ledge." In need of significant renovation, this property has amazing potential. The house has stood prominently in its location since its construction in the 19th century. Designed by Lavius Fillmore, an esteemed architect and timber framer- the detailing throughout was once a thing of beauty. Now available for the next owner to bring their imagination to the property. Currently set up as a main residence with a two bedroom apartment, and located just outside of downtown Middlebury. Offered with +/- 2 acres, with more acreage negotiable. This once magnificent structure is ready for your vision!

Listed by Sarah Peluso 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: 6.49% last updated on 2022-12-01

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$399,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4937083

  • Multifamily
  • Units 3
  • Bathroom 1
  • Square Feet 2,640
  • 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 two 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 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). Currently has a 2 Bedroom APT on the second floor. In order to become a 3 Unit will need town approval and some additional fixtures (kitchen/bath). Currently unoccupied so no rental figures are available but Middlebury's rental market is slim and these units, if reconfigured slightly, would be rented in a heart beat.

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: 6.49% last updated on 2022-12-01

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$399,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4937082

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 2
  • Square Feet 2,640

Prominently located along a main road in the center of the college town of Middlebury, Vermont, versatile building can provide many options. The building is currently set up with two units. A modest two-room (plus a 1/2 bath) unit at the back of the building, a main floor with 4 rooms and two 1/2 baths and a second floor 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). Located in the new "Mixed Use" zoning district, bring your ideas and let's make it happen!

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: 6.49% last updated on 2022-12-01

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

3 Wilmar Street Middlebury VT 05453

Middlebury, VT3 Wilmar Street

Price$335,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4938122

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 1,344
  • Construction Existing
  • Bathroom 2

Beautifully updated home less than 10 minutes from Middlebury's Historic Downtown. A fantastic Raised Ranch lovingly brought back to life. Boasting 3 spacious bedrooms, 2 full baths, including a primary bedroom and bath. A large kitchen features brand new stainless steel appliances and a spacious island over look the light filled dining area with sliding door access to the back deck and the back yard of your dreams! Complete with .82 acres and a fully fenced in level yard provides an abundant amount of space for all your outdoor activities, games, garden, pets and play areas! The open concept dining and kitchen provide ample space to relax or entertain friends and family. With improvements throughout including a brand new furnace, flooring and more! To top it all off, the full basement offers an additional 1,300 sq ft, allowing a future owner to potentially have over 2,600sq ft of living space! There are endless possibilities in this move in ready home.

Listed by Tamithy Howrigan of RE/MAX North Professionals

{$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: 6.49% last updated on 2022-12-01

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

436 East Main Street Middlebury VT 05740

Middlebury, VT436 East Main Street

Price$265,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4938095

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,558

This vintage farmhouse with wraparound porch has a lot of curb appeal! Lived in by the same family for 55 years, it is time for the next owner. Located in the heart of East Middlebury Village, you can walk down the street to the Waybury Inn, or take a dip in the Middlebury river nearby. The house has a roomy floor plan with a sunny, eat in kitchen, and living room with wood floors and wood stove. A first floor office has built in bookshelves, and could also be an additional bedroom. The large laundry room/mudroom are located on your way in from the attached garage. A first floor 3/4 bath rounds out this level! Upstairs are three bedrooms and a 3/4 bath- so room for everyone. An additional unfinished attic space provides storage or expansion possibilities! The lot is large enough to have your gardens or pets. Sidewalks down the street make it safe for walking as you stroll up and down and enjoy the village surroundings- come take a look! A virtual tour is attached to the listing as well! Offer deadline is December 4, 2022.

Listed by Sarah Peluso 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: 6.49% last updated on 2022-12-01

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

160 Foote Street Middlebury VT 05753

Middlebury, VT160 Foote Street

Price$264,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4929671

  • Residential Single Family
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,898
  • Construction Existing

A house with good bones and a great remodeling opportunity. This house has been occupied by the same family since 1966. It's a lovely spot, close to town but far enough away to afford the owners some privacy on a 1.7+/- acre lot. Perfect for a large vegetable/flower garden, orchard and play areas. There are hardwood floors in much of the house, a large sunroom in the back of the house and check out the retro bathrooms! Off the primary bedroom is a sunroom/office/exercise room/sauna room and potential for a spacious modern primary bathroom with a new sauna already included! The laundry room includes a utility sink as well as doubles as the entry from a room that was once a garage. This room offers options as a superb mud/storage room or once again a garage. The house is empty, sheetrock walls were recently primed and sellers are in the process of permitting a replacement septic system. There is a large detached steel building for optimal storage, perfect for storing lawn and sporting equipment as well as covered parking. This property is close to two large lakes, multiple ski resorts and a charming historic college town. Sellers have priced the home with the understanding this is a great opportunity for a new owner with great ideas!

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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.49% last updated on 2022-12-01

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 display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 December 6, 2022 3:53 AM EST.

 

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