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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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457 E. Main Street Middlebury VT 05753-8656

Middlebury, VT457 E. Main Street

Price$1,200,000The price has recently decreased

Active With Contract

MLS Number 4976301

  • Commercial
  • Year Built 1810
  • Square Feet 9,270
  • Acreage 2.9
  • PricePerSqFt 129.45

If this sounds familiar, you're right. The Waybury Inn had the good fortune to be chosen as the image for the Bob Newhart show which aired in the 1980's. Filming for the show was in Hollywood but the Waybury was in every episode and gained some fame for the exterior image of the Vermont sitcom. This is an outstanding opportunity to step into an Historic, successful operating Country Inn that offers great charm and character, warm and inviting atmosphere with comfortable updated amenities. The owners have been in residence for 24 years and have been outstanding custodians of the property. Their staff is loyal and professional. Most of them have been with the Inn for many years and one staff member for 30 years! The Chef is a real asset and has generated, a loyal local following. The 12 individually decorated guest rooms are immaculate with en-suite baths. Kings, Queens, Doubles and Twin bedding are available to accommodate all requirements. The common areas within the inn are warm and inviting; plus in warmer weather, the front, rear porches and patio are perfect spots to relax or have a meal. A stroll through the quiet meticulously maintained gardens, abundant with flowers, statues and sitting areas brings calm. The guests of this inn love it here as noted by the positive reviews on Trip Advisor. Before releasing the financial information, interested prospects will be asked to fill out a Prospect Information Package and provide proof of funds.

Listed by Dick Palmer of Hospitality Consultants,LLC

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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: 6.9% last updated on 2024-02-22

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

1108 Quarry Road Middlebury VT 05753

Middlebury, VT1108 Quarry Road

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

Est. Mortgage: $/month

Active With Contract

MLS Number 4972540

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,502

Tucked away with views of the Green Mountains is this 14-acre haven of unspoiled woodland beauty surrounding a large pond. The property offers an unrivaled sense of privacy just minutes from all that Middlebury has to offer. A welcoming mudroom flows into a generous open living space with a large kitchen, breakfast nook, dining area, and living room with wood-burning fireplace. Down the hall is a cozy bedroom with private bathroom and fireplace, as well as a cherry-lined family room with built-in bookcases and wood stove. Sliding doors lead to a sunroom overlooking the pool and attached greenhouse. Upstairs includes the primary suite with an elevated deck and a hot tub overlooking the Green Mountains. Down the hall are two more bedrooms with a shared full bath. Above the 2-car garage is a separate two room suite with a full bath. There is no shortage of space to enjoy, including a basement ideal for movie nights, patio overlooking an in-ground pool, raised vegetable beds, chicken coop & garden shed, several outbuildings, including a modest refurbished 1800s barn with loft, and winding trails through the woods. Gather around the fire pit at sunset overlooking a private pond that transforms into an ice rink during the winter. A field has also been maintained for soccer and wiffle ball. It's an idyllic setting for memorable gatherings and special events. Make this home your own and begin a chapter filled with adventure, relaxation, and cherished moments.

Listed by Michael Johnston of Coldwell Banker Hickok and Boardman

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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: 6.9% last updated on 2024-02-22

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

5 Court Street Middlebury VT 05753

Middlebury, VT5 Court Street

Price$995,000The price has recently decreased

MLS Number 4922137

  • Commercial
  • Year Built 1880
  • Square Feet 8,553
  • Acreage 0.1
  • PricePerSqFt 116.33

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

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: 6.9% last updated on 2024-02-22

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

103 Court Street Middlebury VT 05753

Middlebury, VT103 Court Street

Price$990,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4980065

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,810

Discover the perfect blend of comfort and opportunity in this spacious five-bedroom, three-bathroom home situated on a sprawling 2.4-acre lot. The main living space welcomes you with an open concept design, providing ample room for a growing family. Two bedrooms grace the main floor, offering convenience and flexibility, while the second floor hosts an impressive trio of bedrooms, including a luxurious primary bedroom suite. Step into the primary suite and indulge in the expansive bathroom, featuring a jacuzzi tub and a separate shower. The suite is complete with a generously sized walk-in closet, offering both style and functionality. The fully walk-out basement presents a myriad of possibilities within its mixed-use zoning. Whether you envision a chiropractic office, daycare, apartments, attorney's office, architect's studio, or even a chic hair salon, this versatile space is ready to transform according to your vision. Previously utilized as a chiropractic office, the potential for this space is boundless. Convenience meets visibility, as the property is strategically located right off Court Street, the main road, ensuring easy access for clients and customers. Ample parking further enhances the property's appeal, making it a versatile canvas for various ventures. This property is not just a home; it's an opportunity waiting to be seized. Explore the potential of this unique residence and its versatile spaces that cater to a myriad of possibilities. Schedule your viewing!

Listed by Kelly Laliberte of Wallace Realty

{$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: 6.9% last updated on 2024-02-22

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

103 Court Street Middlebury VT 05753

Middlebury, VT103 Court Street

Price$990,000The price has recently decreased

MLS Number 4980086

  • Commercial
  • Year Built 1995
  • Square Feet 5,280
  • Acreage 2.4
  • PricePerSqFt 187.5

Discover the perfect blend of comfort and opportunity in this spacious five-bedroom, three-bathroom home situated on a sprawling 2.4-acre lot. The main living space welcomes you with an open concept design, providing ample room for a growing family. Two bedrooms grace the main floor, offering convenience and flexibility, while the second floor hosts an impressive trio of bedrooms, including a luxurious primary bedroom suite. Step into the primary suite and indulge in the expansive bathroom, featuring a jacuzzi tub and a separate shower. The suite is complete with a generously sized walk-in closet, offering both style and functionality. The fully walk-out basement presents a myriad of possibilities within its mixed-use zoning. Whether you envision a chiropractic office, daycare, apartments, attorney's office, architect's studio, or even a chic hair salon, this versatile space is ready to transform according to your vision. Previously utilized as a chiropractic office, the potential for this space is boundless. Convenience meets visibility, as the property is strategically located right off Court Street, the main road, ensuring easy access for clients and customers. Ample parking further enhances the property's appeal, making it a versatile canvas for various ventures. This property is not just a home; it's an opportunity waiting to be seized. Explore the potential of this unique residence and its versatile spaces that cater to a myriad of possibilities. Schedule your viewing!

Listed by Kelly Laliberte of Wallace Realty

{$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: 6.9% last updated on 2024-02-22

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

7 Washington Street Middlebury VT 05753

Middlebury, VT7 Washington Street

Price$780,000The price has recently decreased

Active With Contract

MLS Number 4949541

  • Commercial
  • Year Built 1794
  • Square Feet 3,000
  • Acreage 0.08
  • PricePerSqFt 260

Seriously motivated sellers. Professional office building with space versatility, a highly visible downtown location and updated systems within walking distance to downtown restaurants, convenience of shopping and lovely green/park spaces. This building has long been a law office and is nicely compartmentalized for any number of future uses. On the main entry level (front steps and ramp access) you'll find a large and welcoming waiting room overseen by two admin spaces. The front of the building holds two large private offices with 2 entrance options to each. Two more private office spaces, a conference room, a copier room and a 1/2 bath round out the first floor. Upstairs are two more generously sized offices, a large storage closet, a smaller office and a 2nd conference room, a break room and a 3/4 bathroom. The building has had some winterization work, includes several heat pump units and an air exchange system located in the attic space. Parking is available directly in front of the building (public parking on paved road) as well as 6 designated spaces (during business hours) along the western edge of the Middlebury Natural Foods Coop building. Site is set up with cable internet, phone systems and many office furnishings. NOTE: Building is currently one unit but could be separated spaces, shared spaces, shared amenities. Owners have provided a list of items that can be negotiated in a sale.

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: 6.9% last updated on 2024-02-22

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

79 Court Street Middlebury VT 05753

Middlebury, VT79 Court Street

Price$499,000The price has recently decreased

MLS Number 4979906

  • Commercial
  • Year Built 1890
  • Square Feet 2,197
  • Acreage 0.31
  • PricePerSqFt 227.13

GOLDEN OPPORTUNITY! Prime office space with easy access and excellent exposure in the heart of vibrant Middlebury! Ideal for business incubation, private offices, or owner occupied home business. R12 zoning allows for numerous possibilities! Interior features 9 beautiful naturally lit office spaces along with common areas, locked storage and garage. Exterior features plentiful parking, attractive stonescaping, access ramps, and generous frontage with exceptional visibility. Numerous recent improvements include new roof and gutters, new heating and hot water systems, new basement flooring, insulation and drywall as well as property conversion from oil to propane. Seller is a licensed agent. Also listed as Single Family Residential. See MLS 4979907

Listed by David Davidson of Lake Point Properties,LLC

{$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: 6.9% last updated on 2024-02-22

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

79 Court Street Middlebury VT 05753

Middlebury, VT79 Court Street

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4979907

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,485

GOLDEN OPPORTUNITY! Prime office space with easy access and excellent exposure in the heart of vibrant Middlebury! Ideal for business incubation, private offices, or owner occupied home business. R12 zoning allows for numerous possibilities! Interior features 9 beautiful naturally lit office spaces along with common areas, locked storage and garage. Exterior features plentiful parking, attractive stonescaping, access ramps, and generous frontage with exceptional visibility. Numerous recent improvements include new roof and gutters, new heating and hot water systems, new basement flooring, insulation and drywall as well as property conversion from oil to propane. Seller is a licensed agent. Also listed as Commercial Sale. See MLS 4979906

Listed by David Davidson of Lake Point Properties,LLC

{$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: 6.9% last updated on 2024-02-22

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

118 Three Mile Bridge Road Middlebury VT 05753

Middlebury, VT118 Three Mile Bridge Road

Price$449,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4985673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,232

This unique property is located just south of Middlebury right off of Route 7, making it a very convenient commute to Middlebury, Rutland, and or Burlington. The house has had a lot of work done on it over the last 5 1/2 years including an updated kitchen with all new high-end appliances. However, there is still room to add your personal touch. The house has lots of storage space in the attic and also multiple out buildings. There is an attached garage, with 1 door but has room for a shop area and at least 4 cars. There is another building that has even more space. A wonderful place to call home with extra space for toys and equipment!

Listed by Heather Foster-Provencher of Champlain Valley Properties

{$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: 6.9% last updated on 2024-02-22

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

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 February 27, 2024 8:53 PM EST

 

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