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MLS Number 5093625

• Residential Single Family
• Full Bath 2
• Address 458 East Main Street
• Construction Existing
• Bedrooms 5

1840 Village Home. This great multi-generational or multi-family home has four bedrooms in the main house, an eat-in kitchen with pantry/laundry room, formal dining room, large family room with gas burning soapstone stove, office/craft room, music room/den and 3.5 baths. One bedroom apartment has large living room, walk-in closet, and full kitchen and bath. Ideal as a mother-in-law residence or income-producing apartment. Many recent upgrades including new furnace and appliances. Lots of built-ins, hardwood floors, and Vermont charm throughout. Welcoming front porches overlooking the Waybury Inn. Large, exceptional screened porch on rear of house looking out onto gardens, woods, and the Middlebury River. Large 1800s post-and-beam barn with heated workshop, concrete floor, and loft.

Listed by Beth Stanway of IPJ Real Estate

MLS Number 5090864

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

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

MLS Number 5088782

• Residential Single Family
• Full Bath 4
• Address 29 Kings Row
• Construction Existing
• Bedrooms 5

Perfect for anyone looking for an in-law suite, this home has a first-floor primary suite that is very spacious- giving its occupants a private space separate from the main house, including its own laundry room and office space! The generously sized mudroom entry and walk-in pantry separate this from the open concept kitchen/dining/living rooms. Flooded with natural light, the custom kitchen features granite countertops and cherry cabinetry! Sliding glass doors open up from the dining area to the expansive back deck! The soapstone wood stove in the living room sits on a custom-built stone hearth and can heat up this main level. The family room has pocket doors that can close it off from the rest of the main floor for added privacy. Upstairs are four more bedrooms and two baths! Loads of windows to enjoy the view out the back- a lovely, flat 1.73-acre parcel with stone walls, trees, lots of open space and established gardens, huge deck, pool, and plenty of sun! The partially finished basement has a large recreation room, workout room, workshop, play space, full bath AND plenty of storage. Located in East Middlebury village, down the street from the Waybury Inn, library and playground. Head up the mountain for great skiing, hiking and biking- or walk down the street to the Middlebury River to take a dip or go fishing! Less than 10 minutes into the village of Middlebury, where you'll find great restaurants, shopping, and events at Middlebury College. This house offers all of the space that you have been looking for, at the end of the road for a private setting- what more do you need?!

Listed by Sarah Peluso of IPJ Real Estate

MLS Number 5090473

• Residential Single Family
• Full Bath 1
• Address 2801 Route 7 South
• Construction Existing
• Bedrooms 3

Looking for somewhere truly special to call home? This exceptional property offers 2,140 square feet of beautifully finished living space with 3 bedrooms, 2 baths, and breathtaking Green Mountain views from its private backyard and expansive deck. Meticulously rebuilt from top to bottom by the builder-owner, this home delivers the quality, efficiency, and peace of mind of new construction. Features include durable 2x6 wall construction, a standing seam metal roof, maintenance-free siding, new windows and doors, updated 200-amp electrical service, and FHA heating with an A-coil already installed for future air conditioning. Inside, the bright, open-concept design is filled with natural light and showcases vaulted ceilings, dramatic architectural lines, modern finishes, and a striking stone chimney centerpiece. The thoughtfully designed kitchen is perfect for entertaining, featuring extensive cabinetry, stainless steel appliances, granite and maple butcherblock countertops, a tiled backsplash, and a large center island with seating. The adjoining living and dining spaces flow seamlessly together, creating a warm and inviting atmosphere. The primary suite offers a peaceful retreat with scenic views and an updated bath, while additional bedrooms provide flexibility for guests, a home office, or family living. The fully finished lower level adds valuable living space and includes a new egress window, making it ideal for a recreation room, media room, gym, guest accommodations, or workspace. Outside, attractive stonework, cedar shake accents, vibrant siding, and an oversized detached garage enhance the home's curb appeal and functionality. The generous lot provides privacy and room to enjoy Vermont's beauty in every season. Located just minutes from Middlebury's amenities, this move-in-ready home offers an unmatched combination of craftsmanship, comfort, efficiency, and Vermont charm. The list of improvements goes on and on, but this is one property that must be seen.

Listed by Robert Foley of Flat Fee Real Estate

MLS Number 5084987

• Condo
• Square Feet 1,440
• Bedrooms 2
• New Contruction Existing
• Complex Middlebury East

Easy condo living can be just the right fit for someone that doesn't want to shovel, mow the lawn or navigate home repairs like a roof replacements! All you need to do is turn the inside into the space you want to be in! Whether you are looking to downsize, purchase your first home or your forever home this two bedroom condo could be the perfect fit. On the main floor, just inside the mudroom, you'll find a den/dining room, kitchen, living room (with a propane stove), a 1/2 bath and sliding doors to the deck. Both bedrooms, the 3/4 bath (walk-in shower) and the laundry are on the 2nd floor. Middlebury East is a community of mostly full-time residents adjacent to the Battell Woods and an incredible trail system. You can walk into town quite easily and if you prefer to drive the grocery stores, restaurants, theaters, and shopping are just a few minutes away!

Listed by Amey Ryan of IPJ Real Estate

MLS Number 5091765

• Residential Single Family
• Full Bath 2
• Address 1844 Halladay Road
• Construction Existing
• Bedrooms 4

The classic Vermont farmhouse is on the market! This iconic property also enjoys classic Vermont mountain views that will complete the package. Nestled onto the landscape, the residence is perched up off the road looking west over conserved land to the Adirondacks. This property calls to you with its wrap around porch and handsome details, to come take a look inside! The adjacent barn is part garage, part barn, with a large finished room at the end that is a fully insulated, heated studio space- complete with bathroom! Used for years by the current owners who are artists, but could also be a wonderful music space, home office or even potential guest quarters. The main house has a true Vermont mudroom- big enough for all of your gear- and the way most will enter your home. Once inside you will enjoy the large, eat in kitchen with wood fireplace and built in cabinetry, that enjoys those western views. Butternut from the property was used for most of the trim in the home! The living room is adjacent, and features wood floors and a wood stove that can heat the downstairs. A front parlour serves as another living room, and currently hosts the piano for musical gatherings. An office, powder room and laundry are also on this floor. The living spaces open up to the fabulous wrap around porch where you can lounge day or night to your heart's content. The gracious stairs bring you up to four bedrooms and 2 1/2 baths- enough room for you and your guests! Located just minutes to downtown Middlebury, but your own private oasis and land for gardening or animals. Come check out this beautiful home and make it yours!

Listed by Sarah Peluso of IPJ Real Estate

MLS Number 5080963

• Residential Single Family
• Full Bath 1
• Address 78 Brush Lane
• Construction Pre-Construction
• Bedrooms 3

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 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

MLS Number 5080959

• Residential Single Family
• Full Bath 1
• Address 74 Brush Lane
• Construction Pre-Construction
• Bedrooms 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

MLS Number 5055964

• Residential Single Family
• Full Bath 1
• Address 39 Barnes Brook Road
• Construction New Construction
• Bedrooms 2

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 two-bedroom townhome will be ready for occupancy in May 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. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. 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 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details! Photos are "Likeness Only"

Listed by Sarah Peluso of IPJ Real Estate

MLS Number 5055963

• Residential Single Family
• Full Bath 1
• Address 35 Barnes Brook Road
• Construction New Construction
• Bedrooms 2

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 two-bedroom townhome will be ready for occupancy in May of 2026. 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, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. 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 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

Listed by Sarah Peluso of IPJ Real Estate

MLS Number 5091320

• Residential Single Family
• Full Bath 2
• Address 21 Seminary Street
• Construction Existing
• Bedrooms 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

MLS Number 5086871

• Residential Single Family
• Full Bath 1
• Address 442 East Main Street
• Construction Existing
• Bedrooms 4

This inviting home offers a bright, comfortable layout designed for easy everyday living. The main level flows naturally between the kitchen, dining and living spaces, creating a welcoming environment for gatherings or quiet evenings at home. The updated kitchen blends the convenience of modern living with the charm and character of an older home. Upstairs, a large full bath serves the bedroom level, providing both space and functionality. Outside, the fenced-in backyard is ideal for pets, play or gardening. The garage adds valuable storage and parking. Set on a small, manageable lot the property offers quick access to town amenities and is just a short drive to the Middlebury Snow Bowl. The location is ideal for commuting to Rutland or Burlington as well. The sidewalks in front of the house make it easy to enjoy a morning walk or an evening stroll. This home delivers comfort, practicality, and a great location.

Listed by Heather Foster-Provencher of Champlain Valley Properties

MLS Number 5075441

• Residential Single Family
• Full Bath 1
• Address 35 Ossie Road
• Construction Existing
• Bedrooms 3

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

MLS Number 5089982

• Multifamily
• Address 2337 Vt Route 7
• Units 3
• Bathroom 3
• Acreage 0.48

Here is a delightful opportunity to own a simply versatile property that has been carefully updated over the years. What started as a single family home has been beautifully transformed to this multi-use property. The larger section of the property includes 5 privately rented office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for these office spaces brings in over $2000 and could be even more if rents were adjusted for market rates. There are two furnished studio apartments, one on each level. The 1st floor apartment is currently rented for $1150/month and is heated with both a Rinnai heater and a heated and cooled with a heat pump. It includes a dishwasher, electric stove, stacked laundry and a 3/4 bath. This unit shares a door with one of the aforementioned office spaces so it's possible you could "capture" that room for this apartment space. The second floor unit is a true studio space with a Rinnai heater, heat pump, electric stove, fridge and 3/4 bath and rents for $1400/month. There is additional income potential - rent the 2 bay garage or add that space to one of the apartment rentals and increase the rent. The property is landscaped and has an existing sign for business name display. The parking surface is paved and this property is very tidy!

Listed by Amey Ryan of IPJ Real Estate

MLS Number 5087754

• Condo
• Square Feet 1,397
• Bedrooms 2
• New Contruction Existing
• Complex Middlebury East

Discover this stunning end-unit condominium nestled in one of Middlebury's most charming neighborhoods - where thoughtful updates, effortless living, and a peaceful natural setting come together beautifully. The main level is designed for ease and comfort, featuring an open-concept living and dining area bathed in natural light from expansive windows and sliding doors. Step outside onto your private deck to enjoy the fresh Vermont air, whether basking in the sun or relaxing in the shade beneath a retractable awning. A cozy gas stove anchors the living space, creating a warm and inviting atmosphere year-round. The bright, well-appointed kitchen offers stainless steel appliances, a gas range, and generous counter space - perfect for both everyday meals and entertaining guests. Two spacious bedrooms and a full bathroom complete the main floor, all with no stairs, making for truly convenient single-level living. Downstairs, a finished bonus room provides endless possibilities complemented by an additional ¾ bathroom, in-unit laundry, and abundant storage and workspace. Recent updates include beautiful hardwood floors, fresh paint, and more. Outside, enjoy serene views overlooking a lush lawn framed by mature trees, a detached garage for added convenience, and wonderful outdoor space to call your own. Ideally situated close to downtown Middlebury, top-rated schools, shopping, and world-class outdoor recreation - this one truly has it all. Schedule your showing today!

Listed by David Parsons of RE/MAX North Professionals - Burlington

MLS Number 5058429

• Condo
• Square Feet 1,660
• Bedrooms 3
• New Contruction New Construction
• Address 40 Brush Lane

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, single-level unit is on the second floor and will be ready for occupancy in March 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. Pull into your private garage, and then into your entry hall with a wrap-around porch that provides a covered entry as well as outdoor space to enjoy morning coffee! Up the stairs, you will find an open concept living area with a generous kitchen featuring an island with seating, a pantry, and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. Down the hall, you will find the primary suite with a walk-in closet and 3/4 bath. Two additional bedrooms and a full bath provide room for guests or office space. A laundry room is conveniently located in the hall to complete the living space. Don't forget the basement below that will provide ample storage as needed! 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

MLS Number 5070675

• Land
• Address Tbd Route 7 S
• Acreage 9.8
• Area VT-Addison
• PricePerSqFt 22448.98

Great piece of land in a great location! Secluded when you go up the old road/driveway. Easy access to Rutland or Burlington. Close to everything Middlebury has to offer including stores, restaurants and Middlebury College.

Listed by Beth Stanway of IPJ Real Estate