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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.

225 Wilson Road Middlebury VT 05753

Middlebury, VT225 Wilson Road

Price$3,750,000The price has recently decreased

MLS Number 4993340

  • Commercial
  • Year Built 2019
  • Square Feet 40,000
  • Acreage 6.46
  • PricePerSqFt 93.75

40,000 SF warehouse available for Sale or Lease. Constructed in 2019, maintained in excellent condition. Multiple loading docks and drive-in doors. 12-foot clear height at center beam. Heavy-load concrete rebar flooring for durability. Situated on 6.46 Acres of prime industrial real estate Ample yard space. Convenient access from VT Route 7 only a quarter-mile away.

Listed by Brad Worthen of Pomerleau Real Estate

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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: 6.89% last updated on 2024-07-11

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

111 South Main Street Middlebury VT 05753

Middlebury, VT111 South Main Street

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

Est. Mortgage: $/month

Active With Contract

MLS Number 4997190

  • Multifamily
  • Units 6
  • Bathroom 7
  • Acreage 0.39
  • Square Feet 5,497

What a location! Just down the street from Middlebury College and historic downtown Middlebury, this incredible investment property is ready for new owners. With a total of 9 bedrooms among six units, the structure retains a lot of its original charm. Several exterior porches allow for outdoor living space and hardwood floors and handsome woodwork appear in the main entry and within some units. Many updates have been done to make it easy to just purchase and go! A brand new sprinkler system was just installed, along with a new natural gas boiler. Most of the units have been freshly painted, and all are currently rented. A list of many recent improvements is attached to the listing. If you are looking for an investment property that is turn key- this might just be the one!

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: 6.89% last updated on 2024-07-11

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

484 Halladay Road Middlebury VT 05753

Middlebury, VT484 Halladay Road

Price$1,099,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5004588

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Dreams do come true in life! The current owners hate to leave their dream home but it's the next owner's turn to enjoy this fabulous and classic Vermont farmhouse which has been updated for modern living without stripping any of the charm and character out of the house. Enjoy the warmth of the sun rising, on the wrap-around porch, from behind the Green Mountains in the morning and the spectacular sunsets over the Adirondack Mountain range from the pool deck/patio. The yard is abundant with established gardens, mature trees and raised beds. Use the detached barn to store your lawn mower, snow blower or convert it to use for animals. With 11 acres of property (both sides of Halladay Road), you have plenty of room to wander! The house is filled with period woodwork, stenciled and wide pine floors, fireplaces, pellet stoves and generously sized rooms for you and your guests or family. If you're inclined to entertain the chef's kitchen, with an island and new gas stove, will make it fun and allow you to share time and space with your guests. For the work from home crowd there are plenty of spaces to choose from to make an office. Enjoy hobbies like sewing, puzzles, needlepoint, or other arts and crafts? There are spaces for you too! Need a quiet space to facetime or do homework - still enough space for those activities! This house is a very short drive into the town of Middlebury where you find shops, restaurants and green spaces and you'll be in a recreational paradise!

Listed by Amey Ryan 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: 6.89% last updated on 2024-07-11

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: 6.89% last updated on 2024-07-11

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
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

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

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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: 6.89% last updated on 2024-07-11

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

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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: 6.89% last updated on 2024-07-11

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

45 Court St.(route 7) Street Middlebury VT 05753

Middlebury, VT45 Court St.(route 7) Street

Price$725,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4999647

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3

Historic Victorian Multifamily Home with Owner-Occupied Potential in Downtown Middlebury, VT Step into history with this charming Victorian multifamily home, built in 1840, located in the heart of downtown Middlebury. This well-maintained property features three distinct units, offering a unique opportunity for owner-occupancy with rental income. Live in Comfort, Earn with Ease o Owner's Apartment: Spacious and inviting, the 1620 square foot upstairs apartment offers the perfect blend of historic charm and modern convenience. o Rental Income: Collect a monthly rental income of $3440 from the fully leased 1-bedroom and 2-bedroom apartments on the main level, providing financial ease while you enjoy your new home. Property Highlights o Investment Opportunity: With a continuous occupancy history, this property ensures a solid return on investment. o Recent Upgrades: Enjoy modern living with recent renovations and open concept designs, seamlessly blending contemporary comfort with historic charm. o Prime Location: Located within walking distance to local shops, restaurants, and cultural attractions, making it highly desirable for tenants. o Well-Maintained: The property has been carefully maintained to preserve its historic character while incorporating modern amenities. This is a rare opportunity to live in a historic gem while benefiting from a steady rental income in a high-demand market. Experience the vibrant community of Middlebury and secure a sound investment.

Listed by Deborah Fortier of KW Vermont

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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: 6.89% last updated on 2024-07-11

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

45 Court Street Middlebury VT 05753

Middlebury, VT45 Court Street

Price$725,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4999633

  • Multifamily
  • Units 3
  • Bathroom 3
  • Acreage 0.2
  • Square Feet 3,120

Historic Victorian Multifamily Home in Downtown Middlebury, VT Discover a piece of history with this charming Victorian multifamily home, built in 1840, located in the heart of downtown Middlebury. This well-maintained property features three distinct units: a 1-bedroom and a 2-bedroom on the ground level, and a spacious 2-bedroom with large bonus room on upper floors. The lower-level apartments are fully leased with high quality tenants generating $3440 income per month. The upper-level apartment is being left empty to accommodate a potential buyer who may want to reside on premises. Estimated rent if leased would be $2400 per month. Property Highlights Investment Opportunity: This property offers a solid return on investment in a high-demand rental market. Recent Upgrades: Enjoy modern living with renovated lower-level apartments with open concept designs, blending contemporary comfort with historic charm. Prime Location: Situated within walking distance to local shops, restaurants, and cultural attractions, making it highly desirable for tenants. Well-Maintained: The property has been carefully maintained to preserve its historic character while incorporating modern amenities. This is a rare opportunity to own a historic gem in Middlebury, offering both stability and growth potential. Don't miss out on this exceptional investment in a vibrant community. For more information or to schedule a viewing, contact us today!

Listed by Deborah Fortier of KW Vermont

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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: 6.89% last updated on 2024-07-11

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

105 Court Street Middlebury VT 05753

Middlebury, VT105 Court Street

Price$699,000The price has recently decreased

Active With Contract

MLS Number 4989307

  • Commercial
  • Year Built 1983
  • Square Feet 3,810
  • Acreage 1.23
  • PricePerSqFt 183.46

Three full stories of usable space, tons of parking and incredible Route 7 exposure. The lowest level of this building has been most recently used as a shipping/receiving/retail establishment with parking level entry, large/flat access from the parking with an extra wide entry door, a break room, utility room, storage space and two 1/2 bathrooms. The middle level is a print/scan shop with open retail and office space. It's a wide open floor plan so use your imagination. On the upper level (3rd floor) are two large offices, a smaller nook and another bathroom. The property is on a large lot directly across the street from M&T bank, Pediatric Dentistry, close to the Hannaford Shopping plaza. Perfect location for so many uses! This is the sale of the real estate only. Showings to be accompanied by a licensed real estate agent. Ask your agent about virtual tour available. Showings during business hours preferred. Monday-Friday 8 - 6, Saturday 8 - 4. Sunday 10-3 or by appointment with advance notice.

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: 6.89% last updated on 2024-07-11

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

74 Court Street Middlebury VT 05753

Middlebury, VT74 Court Street

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4989606

  • Multifamily
  • Units 4
  • Acreage 0.3
  • Square Feet 1,440
  • Utilities Phone

Welcome to this charming 4-unit apartment building located in the heart of Middlebury. This property offers a fantastic investment opportunity in a desirable location. Property Highlights: - Well-maintained exterior with curb appeal. - Off-street parking for residents' convenience. - Close proximity to local shops, restaurants, and entertainment Investment Opportunity: - Potential for rental income and long-term growth. - Perfect for both seasoned investors and first-time buyers. - Strong rental demand in the Middlebury area. - Great opportunity to expand your real estate portfolio. Don't miss out on this fantastic investment opportunity in Middlebury. Contact us today to schedule a viewing and make this 4-unit apartment complex your next real estate venture!

Listed by Courtney Houston DeBisschop 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: 6.89% last updated on 2024-07-11

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

2225 Route 7 South Middlebury VT 05753

Middlebury, VT2225 Route 7 South

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5001576

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Looking for great exposure for your business and a great home on the same property? This is the location for you! This property is located on Route 7 South in Middlebury offering public water and sewer, a well lit space attached to a workshop with overhead door as well as a 2 car attached garage to the 4BR, 3BA home. AG rural district which has housed a successful retail business for many years. There is potential for an apartment to help pay your mortgage. It is now your turn to make your dream and profits come true. Just a wonderful opportunity.

Listed by Nancy Larrow 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: 6.89% last updated on 2024-07-11

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

3210 Case Street Middlebury VT 05753

Middlebury, VT3210 Case Street

Price$520,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4987283

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

You will love this beautifully updated split level Middlebury home with three bay garage which offers plenty of space for vehicles and storage. The lower level of this home is spacious and open. this was previously a registered day care, also perfect for a home business, or as additional living space. There is a small kitchenette and a bathroom. On the other end of the basement is the utility room, as well as another bathroom, laundry room and bedroom. plenty of storage space. The upstairs entry has a new slate floor with a nice entrance, Kitchen with island and dining area opening into the nice size living room area, two bedrooms, and a full bathroom. The home has had many updates from 2021 to 2023: new windows, new doors, new roof, new furnace system, with a new chimney liner as well as updated electrical work. This is a lovely well-maintained property ready for you to make it home!

Listed by Roxanna Emilo of Emilo Real Estate,LLC

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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: 6.89% last updated on 2024-07-11

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 July 15, 2024 4:10 PM EDT

 

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