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21 Seminary Street Middlebury VT 05753

Middlebury, VT21 Seminary Street

Price$549,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091320

  • Residential Single Family
  • Full Bath 2
  • Address 21 Seminary Street
  • Bedrooms 5
  • Bathroom 5

Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple possiblities such as a home based occupation or bed and breakfast. With a total of 5 bedrooms, 5 bathrooms and over 3600 finished square feet, there is so much opportunity to personalize a layout that best suits your wants and needs. The rear of the home is part of a newer addition that includes a 1 bedroom apartment with 3/4 bathroom, living room and office. Adjacent to the apartment is a 2 car garage that was also part of this addition. Above both is a large timber frame family or primary bedroom with vaulted ceilings, custom built ins, and a 3/4 bathroom. The property is priced well below recent appraisal at just over $150/square foot to enable the new owner to create their own vision of this historic home with exterior updates. Conveniently walkable to all of Middlebury's downtown offerings. Imagine village living at its best!

Listed by Katrina Roberts of Vermont Real Estate Company

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

74 Brush Lane Middlebury VT 05753

Middlebury, VT74 Brush Lane, Unit 10.5

Price$540,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5080959

  • Residential Single Family
  • Full Bath 1
  • Address 74 Brush Lane
  • Bedrooms 3
  • Bathroom 3

Special pricing for qualified buyers! Down payment and closing cost assistance of up to $42k may be available for qualified households. 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 duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

Listed by Sarah Peluso of IPJ Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

38 Martha's Way Salisbury VT 05769

Salisbury, VT38 Martha's Way

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5075792

  • Residential Single Family
  • Full Bath 2
  • Address 38 Martha's Way
  • Bedrooms 4
  • Bathroom 3

NEW 2026 CONTEMPORARY RANCH - SALISBURY, VT ( To Be Built) Be the first to own this thoughtfully designed new-construction home located in the picturesque town of Salisbury, Vermont. This contemporary ranch will offer modern comfort, quality craftsmanship, and close proximity to some of the area's most desirable outdoor destinations. The property features 3 bedrooms, 1 full bath on main level and an additional full master suite above garage with private bathroom suite. Open-concept kitchen and dining area and appliance package included: electric stove, refrigerator, dishwasher, microwave Basement apartment or in-law suite (appliances not included) Photos likeness only. Building plans negotiable with opportunities for customization. Buyer may select finishes including cabinetry, countertops, flooring, paint colors, and more. Minutes to Lake Dunmore and Branbury State Park (swimming, boating, kayaking) Close to Middlebury Snow Bowl for skiing and snowboarding, Access to nearby hiking trails including Silver Lake and Falls of Lana. Peaceful setting with convenient access to Middlebury and local amenities. Ideal for year-round living or a seasonal Vermont retreat. Enjoy modern design, outdoor recreation, and the charm of a welcoming community.

Listed by Roxanna Emilo of Emilo Real Estate, LLC

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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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: 6.48% last updated on 2026-06-04

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

95 Seminary Street Extension Middlebury VT 05753

Middlebury, VT95 Seminary Street Extension

Price$489,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090864

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,916

This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck - the perfect place to entertain, relax, and take in views of your own private slice of Vermont. Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings. The spacious home is conveniently located just minutes from Middlebury College, Porter Medical Center, and the Middlebury Natural Foods Co-op, while Burlington International Airport is only 52 minutes away. The oversized two-car garage provides ample room for vehicles, hobbies, and storage, with an additional separate workshop or storage area located at the rear. Outdoor enthusiasts will also appreciate the home's close proximity to several walking trails and recreation opportunities.

Listed by Sean Dye of BHHS Vermont Realty Group/Vergennes

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

12 Mountain Street Bristol VT 05443

Bristol, VT12 Mountain Street

Price$488,500The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5092559

  • Residential Single Family
  • Full Bath 1
  • Address 12 Mountain Street
  • Bedrooms 4
  • Bathroom 2

This charming cottage styled cape is a once in a generation opportunity to enjoy life in Bristol Village! Watch the July 4th parade from your front steps or yard. Enjoy the convenience of being close to downtown shops, schools and parks with street lights and sidewalks. Beautifully landscaped with lots of perennials, a paved driveway lined with Bridal Wreath, a grape arbor and terraced back yard with stone steps - more perennials, a deck off the family room, as well as an attached 2-car garage which flows into the yard or onto the screened in porch, which serves as a mudroom. The kitchen has updated Silestone countertops, SS appliances, and an eat-in counter, wheelchair accessible. This is truly a beautiful blend of original and new features with built-in pass through cupboard from the kitchen into the dining room, as well as other lovely built-ins throughout the house. 4 bedrooms with the primary on the first floor along with the other bedroom and a walk in shower in the main level bath! 2 upstairs bedrooms, some featuring walk-in closets. The family room hosts the first floor laundry and enjoys the deck and view of the back yard. The living room has a brick fireplace and attached sunroom! Beautiful hardwood floors, doors and crystal doorknobs reflecting some of the originality of the home! This is truly a marriage of craftsman styling and traditional cape design. Truly a gem with ease and comfort of a more modern home!

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

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

47 Barnes Brook Road Middlebury VT 05753

Middlebury, VT47 Barnes Brook Road

Price$482,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5060138

  • Residential Single Family
  • Full Bath 1
  • Address 47 Barnes Brook Road
  • Bedrooms 3
  • Bathroom 3

This price is for qualified buyers! Inquire with your agent to see if you qualify and are able to purchase at this price. This unit is also available at the market price of $699,500. 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 spring of 2026. Energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area which enjoys plenty of natural light from the many windows. The generous kitchen features an oversized island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxing. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find a primary suite with a spacious walk-in closet and en-suite bath featuring a double vanity, complemented by 2 other bedrooms and a bath. The lower level provides private garage parking, gear-friendly mudroom and laundry room. A partially finished bonus room and utility space round out that level. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

Listed by Sarah Peluso of IPJ Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

29 Barnes Brook Road Middlebury VT 05753

Middlebury, VT29 Barnes Brook Road, Unit 9.6

Price$482,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5072389

  • Residential Single Family
  • Full Bath 1
  • Address 29 Barnes Brook Road
  • Bedrooms 3
  • Bathroom 3

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 the forefront, each unit will be heated and cooled with mini split technology, with a whole house ventilation system. Step inside the open concept first floor living area which enjoys plenty of natural light from the many windows. The generous kitchen features an oversized island with seating, energy star appliances, and direct access to a private deck, perfect for morning coffee or evening relalxing. The kitchen transitions seamlessly into spacious dining and living areas making entertaining a breeze. A powder room on this level is great for guests. Upstairs you will find a primary suite with spacious walk-in closet and en-suite bath featuring a double vanity, complemented by 2 other bedrooms and bath. The lower level provides private garage parking, gear- friendly mudroom and laundry room. A partially finished bonus room and utility space round out that level. Future community amenities will include green space, community garden, access to trails and more. Inquire for more details! Photos are "Likeness Only"

Listed by Sarah Peluso of IPJ Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

35 Ossie Road Middlebury VT 05753

Middlebury, VT35 Ossie Road

Price$479,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5075441

  • Residential Single Family
  • Full Bath 1
  • Address 35 Ossie Road
  • Bedrooms 3
  • Bathroom 2

Spacious East Middlebury Ranch on 1.20 Acres with Mountain Views Set on a generous 1.20-acre lot with a beautiful Green Mountain backdrop, this inviting ranch-style home offers comfort, flexibility, and room to grow. The property includes an attached two-car garage plus a separate detached building-perfect for hobbies, a workshop, or a small business-complete with its own power supply. Home has many new upgrades, new windows, new roof, new siding (concrete James hardy), new heating system VT GAS, new electrical and new deck! Inside, the bright and open living space features a sunny three-season sunroom that flows into the dining area and kitchen. The main level includes a full bathroom, while a convenient half bath is located on the finished lower level. The lower level provides excellent versatility for additional living space, whether you need room for guests, extended family, or recreation. Enjoy the ease of being close to East Middlebury amenities, including a bakery, convenience stores, the post office, and more. Outdoor enthusiasts will appreciate quick access to skiing, hiking, and snowmobiling trails. The expansive yard offers ample space for gardening, play areas, and pets. This spacious lot also offers the potential for subdivision to create an additional building lot, giving buyers even more opportunity. A wonderful chance to enjoy space, comfort, and flexibility in a desirable location.

Listed by Roxanna Emilo of Emilo Real Estate, LLC

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

265 Stonewall Drive Bristol VT 05443

Bristol, VT265 Stonewall Drive

Price$459,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5090302

  • Residential Single Family
  • Full Bath 2
  • Address 265 Stonewall Drive
  • Bedrooms 3
  • Bathroom 3

The gracious covered porch welcomes you to this classic home, and is where you will want to sit and enjoy a relaxing moment! This property boasts a sizable yard with enough open space for a fire pit, gardens and play, but framed with woods that maintain a private, peaceful setting. Once inside, the open concept floor plan features a living room with hardwood floors that flow into the kitchen and dining areas beyond. The walk in pantry is a great feature in the sizable kitchen, and laundry is nearby. An amazing three season porch is off of the dining area, and is the perfect spot for relaxing or dining on warm weather days- rain or shine! This leads to a deck and overlooks the lovely yard for a smooth indoor/outdoor transition. A den on the main floor allows for a space that is separate for TV watching, reading or office space and a pellet stove keeps it cozy on colder days. The powder room is across the hall. Upstairs is the primary suite with its own full bath, along with two additional bedrooms and full bath. The attached, two car garage offers convenience and storage! A full, dry basement is also great for storage, and currently houses an exercise pool that can stay with the home if desired. Don't forget the standby generator! That gives peace of mind in all kinds of weather. Located only 10 minutes to downtown Bristol, 20 minutes to Hinesburg, and convenient to Burlington. This attractive home has the space that you need, and the setting you have been looking for!

Listed by Sarah Peluso of IPJ Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

129 Daigneault Hill Road Orwell VT 05760

Orwell, VT129 Daigneault Hill Road

Price$455,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5092277

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,446

Combine the beauty of a peaceful Vermont country road lined with maples, an antique home that is beautifully situated on 28 acres, and 2 outstanding outbuildings that offer you a hundred different uses. Add a chicken castle that will house 36 nesting boxes and you have your version of " Green Acres"! The house has many original features including hardwood floors, multiple wood stoves and one great stone fireplace, lovely large windows, light filled rooms, beautiful woodwork and lots and lots of character. The outbuildings will knock your socks off with all its possibilities. The main 2 story barn houses the garage, 2 lean-to's for equipment and stacked wood, a wood shop, basement storage, and a second story for whatever is left. Designed to mimic a "monitor style" barn, that adds appeal to the country feel. But we are still not through--- a 5 stall horse barn, tack room, wood stove heat, and a lean-to equipment shed. All this just minutes from charming and historic Orwell Village, Brandon, Middlebury and the Rutland area. A true treasure in the heart of Orwell.

Listed by Tony Shaw and Stephanie Douglas of KW Vermont

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

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Copyright 2026 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 June 9, 2026 3:25 PM EDT

 

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