34 properties for sale in Woodbridge, Middlebury Middlebury town Addison County Vermont

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!

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

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, single-level unit is on the second floor and will be ready for occupancy in April 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 prima

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

The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher and Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved lan

Located at the end of the road, an affordable home with a welcoming front porch and garage awaits. Wood floors in the living areas and a propane stove in the living room for chilly nights. A first-floor office could serve as a bedroom, and a bath with laundry is convenient. Upstairs are four bedrooms and two bathrooms. The one-car garage is extra deep, with a back space for great storage. Located just 4.5 miles from downtown Middlebury for all of the conveniences of town. Close to the trail around Middlebury for great walking and biking trails. Being sold as is. Offer deadline is Friday, July 17th at 3pm

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 private office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for three of these office spaces currently brings in $1200 and could be even more if rents were adjusted for market rates and the two, currently empty, other offices were rented. 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

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 spac

This location does not come along often! Sited on the east side of Cider Mill road looking towards Middlebury College and the Green Mountains, and just 2.5 miles to downtown. Over 7 acres of land has been opened up to share the incredible eastern views. There is an old farmhouse on this land that is not currently livable. It would require a complete transformation or a new owner could start fresh! The house will not be financeable as a residence. To complete the classic Vermont setting, a barn sits further back on the property adding to the possibilities. Plenty of open land for gardens, animals or additional structures. Whether you renovate the existing home or use this site to create something new, this location holds a lot of potential!

Set gracefully along a quiet ridgeline in the picturesque village of Weybridge, Vermont-just minutes from Middlebury College and the vibrant charm of downtown Middlebury-this exceptional custom residence offers a rare balance of seclusion, intention, and refined simplicity. Designed and built by its current owners with extraordinary care, this one-bedroom home with a separate studio is a true sanctuary for those seeking privacy, creativity, and connection to the natural landscape. Every detail reflects a thoughtful commitment to quality and timeless design. Black-framed Marvin Integrity windows create a striking contrast against the crisp white interior and exterior, while wide-plank French oak floors bring warmth and continuity throughout the living spaces. Tumbled quartzite tile underfoot in the kitchen and bath adds subtle texture and enduring elegance. Drawing inspiration from classic English design, the home is enriched with carefully curated elements sourced abroad-from elegant f

Charming and full of rich, Vermont character - a place you'll be proud to call home! According to local legend, in it's early years, this was the office for the Pulp Mill. Fast forward a few years and a local family decided to make it their home. Then for the next 50+ years this home has been continually expanded, improved and updated by the people who have loved living here! Today's home offers gleaming hardwood floors, antique and functional fixtures alongside modern amenities like heat pumps and power for an electric car charging hookup. The first floor spaces include a welcoming mudroom - adjacent to the laundry room which is key when you come in from the garden or the pool - an updated kitchen with newer appliances including an induction stovetop and tons of cabinet/counter space, a spacious living room with a woodstove insert (the Winter Warmer from VT castings), a dedicated dining room, cozy den and storage room with custom shelving to keep things neat and tidy. On the second fl

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 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,

Conveniently located in the sought after Buttolph Acres neighborhood, this neat and tidy home has been thoughtfully updated for you to move right in! Exterior siding was replaced with fiber cement clapboards, and insulation was added at that time for a energy efficient envelope. Walk into the open concept living/kitchen dining area, and you will appreciated the custom woodwork at every turn. Maple floors were installed throughout the main level, and the kitchen features cherry countertops with beautiful curved edges. The large island is the centerpiece of this space, and has room for casual seating. Built in benches in the dining area are perfect to tuck your table up against for entertaining. Another built in bench was added in the living room to provide ample seating, and to take advantage of the window seat potential! A pellet stove adds extra warmth to this whole area. Down the hall you will find the primary bedroom and full attached bath along with a guest bedroom and full bath. T

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 s

Set on 5.25 picturesque acres offering access to 1,200 acres of Snake Mountain Wildlife Management Area, this beautifully restored farmhouse offers exceptional privacy, timeless character, and breathtaking Green Mountain views. Extensively renovated while preserving its historic charm, the home seamlessly blends classic Vermont architecture with modern comfort. The welcoming foyer opens to sun-filled living spaces featuring hardwood floors, exposed beams, original woodwork, and oversized windows framing spectacular vistas. The updated kitchen is designed for everyday living and entertaining with granite countertops, stainless steel appliances, abundant cabinetry, and an adjoining breakfast area. Multiple gathering spaces provide flexibility for formal entertaining, relaxed evenings, or working from home. The spacious primary suite is a peaceful retreat, while four additional bedrooms offer room for family and guests. Updated baths combine fresh finishes with farmhouse style. A finished

Nestled on 5 peaceful acres with a tree lined drive. This charming property offers the perfect blend of privacy and country living with views. The home features 3 bedrooms with two separate living areas, providing plenty of room for relaxing or entertaining. This layout would be perfect to share with a family member that wanted their own space, including a kitchenette and private entrance. Outside, you'll find a deck to relax on listening to the birds, plenty of garden spaces to work in and a detached garage, storage shed, and an additional outbuilding. Combined you have ample space for vehicles, hobbies, animals or maybe a play house. You have the convenience of traveling to Vergennes, Middlebury and Bristol within 10-15 minutes for all of your needs. Enjoy the tranquil setting, scenic surroundings, and the opportunity to make this peaceful home yours

Designed for effortless first-floor living, the home features a spacious primary suite on the main level, ideal for comfort and accessibility. A welcoming mudroom and convenient guest bath set the tone as you enter into the warm and inviting living space, complete with custom bookcases and a cozy gas fireplace, perfect for snowy Vermont evenings. Large windows and a deck overlooking the neighborhood pond create a peaceful backdrop year-round. The layout flows beautifully into a formal dining area and a generous eat-in kitchen with plenty of room to gather, cook, and entertain. Downstairs, the finished walkout basement expands the living space even further with flexible space for hobbies, recreation, or a home office. On the second level are two additional bedrooms, another full bath and a small landing/reading nook. Additional highlights include direct-entry garage access, abundant storage, and immediate proximity to the extensive trail network (Trail Around Middlebury) bordering the n

Opportunity Knocks in the conveniently located 5 bedroom home in Middlebury! The property is set back off the road on 2.4 acres with a partially fenced in yard and a deck that faces west. Have you ever wanted to have your own business at home and raise your family too, all in the same space' This home presents a multitude of opportunity; Multi-generational living, Home business or rent out the walk-out basement to one or multiple vendors. The home is very spacious and bright. Upstairs you will find 3 very roomy bedrooms including the primary suite with walk-in closet. There is also a walk-thru closet from the main bathroom so if you don't want to disturb your partner in the morning, you can get ready for the day here! If stairs aren't for you there are two bedrooms on the first floor! Above the two car garage is a large storage area that is unfinished. One of the best things about this home is its convenience to everything - Schools, Shopping, Local Airport, Skiing, Middlebury College,

Charming 3-bedroom home located in Middlebury. This well-maintained property is both bright and functional with a layout that has comfortable living spaces, good-sized bedrooms, storage and even a bonus room. The sunny level backyard is perfect for gardening, outdoor play and entertaining. There is also a handy shed for your lawn equipment or extra storage. Located close to schools and offering an easy commute to Middlebury College, Porter Medical Center or longer commutes to Burlington and Rutland. A great opportunity for those seeking a convenient in town location, low maintenance, with a lovely outdoor space in a neighborhood setting

This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with 3/4 bathroom. Upstairs, you'll find three additional bedrooms, along with a bonus room that was previously used as a laundry room and still retains its hookups. The electrical system has been updated, and a new hot water tank was installed in 2024. Perched above the road on the edge of Buttolph Acres, this corner-lot property features a welcoming front porch and a spacious fenced side yard. Sidewalks right outside the front door lead all the way to Middlebury's public schools and provide convenient access to downtown shops, restaurants, and amenities. This is a rare chance to own a classic Middlebury home at a price point that leaves room to make it yo

Well-maintained three-unit property just minutes from downtown Middlebury. Two units were renovated in 2019 with modern updates while retaining Vermont character. All units are currently rented and feature private entrances, laundry, separate utilities, and additional storage. Quiet, scenic setting with quick access to shops, restaurants, and an easy commute to Burlington, Middlebury, Bristol and Vergennes. Ample on-site parking and outdoor space add to tenant appeal. Strong rental history and desirable location make this an excellent investment opportunity in Addison County. Recent reappraisal from the town came in at $609,300

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 private office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for three of these office spaces currently brings in $1200 and could be even more if rents were adjusted for market rates and the two, currently empty, other offices were rented. 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

Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. Combining comfort, convenience, and thoughtful updates, this move-in-ready home is ideal for first-time buyers, downsizers, or anyone looking for low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer and dryer creating a fresh and inviting space to call home. The three spacious bedrooms provide flexibility for guests or a home office, while the full bath is designed for everyday ease. Step outside to enjoy the newly built back deck, perfect for relaxing with your morning coffee, entertaining friends, or enjoying Vermont's changing seasons. A full basement offers abundant storage space, giving you plenty of room for seasonal gear, hobbies, or extra belongings. Conveniently located just minutes from downtown Middlebury, you'll have easy access to local shops, restaurants, parks, schools, and all the charm thi

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

Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills the air as you relax on your porch or savor a warm summer evening by the firepit. This classic Vermont farmhouse has been beautifully updated inside with a gorgeous custom kitchen complete with high end appliances that are a work of art. A 48 Italian gas range, Big Chill fridge and a handmade Moroccan brass faucet are just a few of the details! Custom cabinetry includes a bespoke island that is the center of the chef's domain. Throughout the home thoughtful design choices are around every corner. With an acceptable offer, the house can be sold mostly furnished! Wood floors throughout, and natural light is in abundance. A first floor bedroom and fully remodeled bath make one level living possible. The living and dining rooms feature built in cabinetry, and a wood burning fireplace is a focal point in the living room for cozy nights. Three additional bedrooms and another fully remodeled bath are upst