Properties Near 5285 Main Street Waitsfield, VT

Experience the ultimate mountain retreat in this stunning ski-in/ski-out 4-bedroom, 2-bathroom luxury condo at Sugarbush Resort. Perfectly positioned for both adventure and relaxation, this exquisite property offers breathtaking mountain views and direct access to some of the best skiing in the Northeast. Oversized windows overlook Village Run, bringing in natural light and framing the beauty of the slopes. After a day on the mountain, step into a recently updated high-end kitchen, complete with top-tier appliances, quartz countertops, and custom cabinetry, ideal for preparing gourmet meals Unwind in the inviting living area, where a Jøtul wood stove adds warmth and ambiance, creating the perfect après-ski atmosphere. From the comfort of your sofa, watch the snowcats groom the trails for another day of pristine skiing. Large windows and an open floor plan enhance the sense of space, bringing the beauty of the mountains indoors. Beyond winter sports, this prime location offers four-season recreation, including hiking, biking, and golf. Conveniently located on the shuttle route, you’ll enjoy easy access to Sugarbush Health & Recreation Centre, Sugarbush’s vibrant village, restaurants, and amenities. With a fantastic rental history and proven Airbnb income of $1,500 per night, this property is not just a retreat but an investment. Whether you're seeking a luxurious getaway or a high-performing rental, this condo delivers the best of ski resort living.

Rare to find an in-town location in the Waitsfield Historic district. Close to the covered bridge, library and town hall, this 3 bedroom single family residence has a spacious 2 bedroom apartment over the barn and another 2 bedroom unit attached to the house. The current owner occupies the 3 bedroom house with sitting room, living room and fireplace and rents the apartment over the barn and has commercial offices rented in the 2 bedroom attached unit. Beautiful wood flooring, built-ins throughout and lot's of natural light. Have a seat on the covered front porch and overlooking Historic Waitsfield and the ridgeline beyond. Front yard overlooks Farr Lane and the large backyard provides privacy and a great open area. There's an older outbuilding that could be storage or repurposed as an artist studio or?? Lot's of options for additional income or the flexibility to have home and office in a truly convenient location.

GREAT NEW PRICE ! This exceptional property offers a rare blend of Million Dollar Views !! Sweeping mountain views, recreational opportunities, and comfort. The perfect year-round retreat for outdoor enthusiasts and those seeking comfort in a serene setting, this property features a private clay tennis court, close proximity to premier ski resorts like Sugarbush and Mad River Glen, and nearby access to world-class biking and hiking trails. The Mad River Valley is also a destination for water sports, with endless options for swimming holes, paddling, and fishing. Inside, the home features elegant living spaces with updated appliances, expansive windows, and high-quality wood finishes that reflect the surrounding landscape. Thoughtful additions will make your life easier - use the dumb waiter to bring your groceries from garage to kitchen! Plus, a main floor bedroom and ensuite bath with walk-in shower give the option of accessibility. A second primary with ensuite bath on the 2nd floor allow for plenty of options. Step outside to expansive decks and patios that invite you to dine al fresco, host gatherings, or simply relax and take in the stunning views. The area offers endless community events, including the popular Waitsfield Farmers Market, local theaters, and copious shopping and dining options. Sold TURNKEY fully furnished !

Here is your opportunity to be only the second steward of this charming home and property nestled along the Slide Brook in Fayston. Walking distance to the Fayston Elementary School, and less than a one-minute drive to Sugarbush Resort's Mt. Ellen. Tastefully updated over the years by the original owners, there is a lot of love in this home. The warm and open floor plan allows for wonderful gatherings with friends and family. In the summertime, relax out back on the deck and take in the view and soothing sounds of the Slide Brook that bisects this private homestead. Incredibly convenient to all three peaks, and just minutes from town. A truly wonderful place to call home or as a base camp to your year-round adventures.

Easy access to the slopes of Sugarbush Resort from this nicely updated and spacious mountain retreat. Open concept plan with floor to ceiling windows creating rooms filled with natural light. Modern appliances, stone counters and an oversized pantry. Convenient dining area with plenty of room adjoins the cozy living room highlighted by lots of windows and an easy to use gas fireplace. The generously sized primary bedroom is upstairs with walk in closet, an additional storage area, full bath and outdoor deck/balcony. On the main level you'll find 2 additional bedrooms, one ensuite with outdoor access and the other with easy access to a full bathroom just across the hallway. Laundry is conveniently located on the main level. On the lower level of the building is a secure storage locker room for all your seasonal items. Make this your special getaway home for all the fun and recreational activities available in the Mad River Valley

Charming and well-maintained, this 3-bedroom, 2-bathroom home is perfectly situated in the heart of Waitsfield, nestled in Vermont’s beautiful Mad River Valley. With desirable mixed-use zoning, this property offers flexible living and business opportunities. Inside, you’ll find a bright and open kitchen/dining area ideal for gatherings, a spacious first-floor bedroom, first-floor laundry, and a second kitchen that provides added functionality—perfect for extended family, guests, or potential rental options. A loft/office space above the primary bedroom offers a cozy retreat, perfect for a home office or additional family room. Step outside to enjoy a peaceful, private covered porch with local views. A detached garage offers additional storage or workspace. A new roof was installed in 2024, offering added value and peace of mind. A hybrid heat pump water heater was added in 2019, enhancing energy efficiency and comfort. Located within Irasville Village, you’re just moments from all the Mad River Valley has to offer: world-class skiing at Sugarbush and Mad River Glen, cross country skiing, scenic hiking and mountain biking trails, golf, and a wide selection of restaurants and shops. Whether you're looking for a cozy full-time residence, a weekend getaway, or a home-based business opportunity, this property delivers. Also listed as a commercial property under MLS# 5057886. A true must-see in one of Vermont’s most sought-after communities!

Turn key end unit! Just minutes from the ski trails of Sugarbush Resort with easy access to the shuttle. Enjoy 3 en-suite bedrooms. Updated kitchen with stainless appliances, custom cabinets & granite counters. Living room has a natural stone surround gas fireplace and floor to ceiling windows. Convenient location on the Sugarbush Access Road just across from Alpine Options Ski Shop. An outdoor, in-ground pool and tennis court for summer fun.

Come and see this inviting 3-bedroom, 2-bath home which offers a perfect blend of comfort and privacy! Full of warmth and character, it’s the kind of place that just feels like home the moment you arrive. A paved driveway leads to the 2-car garage, connected by a breezeway for easy, all-weather access. Step into a well-planned tiled mudroom, where a transom window and elegant French door provide a graceful transition to the main living area. Inside, the thoughtful layout includes a main-floor primary suite and a welcoming living room anchored by a beautiful brick fireplace; a perfect spot for making memories on cozy winter nights! Or perhaps you'll unwind on the screened porch, spotting hummingbirds as you admire the perennial gardens. The updated kitchen features granite countertops and flows effortlessly into the dining room and sunny back deck; ideal for entertaining or simply soaking up the outdoors! In winter, enjoy serene mountain views and radiant sunsets from the deck, or gather around the firepit for evenings under the stars. Whether you’re hosting summer barbecues, enjoying colorful fall foliage, or sipping morning coffee in the fresh spring air, this home offers seamless indoor-outdoor living year round! Nestled in a peaceful neighborhood with quiet gravel roads perfect for strolls, yet less than 10 minutes to town and under 20 minutes to Sugarbush and Mad River Glen, this home strikes the perfect balance of tranquility and convenience! Showings Start 8/2 at 3:30.

Tucked in the heart of the Mad River Valley, this exceptional 3.25-acre property blends natural beauty, modern comfort, & pure VT magic - perfect as a primary home or a continued successful Airbnb. With 500' of river frontage & a private swimming hole, this four-bedroom, two 3/4 -bathroom home is beloved by all who stay here. Guests adore its "treehouse" charm & the child-like wonder it inspires. The current owners have invested over $246,000 in thoughtful upgrades, transforming the property while honoring its character. Major upgrades include three Mitsubishi mini-splits for year-round comfort, fully remodeled bathrooms, numerous windows & doors replaced, & the addition of a custom sliding door in the living room. The moment you arrive you're tempted to explore. Winding trails, forested nooks, & river access invite curiosity & connection to the land. A partially covered front porch wraps around to a back deck overlooking the beautiful Mad River - an ideal spot to relax, listen to the birds, watch wildlife, & soak in the sounds of the flowing river. An outdoor yoga deck adds yet another way to enjoy the peaceful setting. Whether you're swimming in the river by day or enjoying s'mores by the firepit at night, this property offers the best of VT! Located just 10 minutes to Sugarbush & Mad River Glen, & 5 minutes to the amenities of downtown Waitsfield. This fully furnished home offers the perfect location for year-round recreation in the Mad River Valley! Showings begin 9/2.

This immaculately maintained 4-bedroom, 2-bath home offers the perfect balance of rustic charm with modern updates throughout. Set on 2.38 wooded acres, you have privacy from neighbors and can enjoy the surrounding natural beauty of Vermont. The home features a warm and inviting stone fireplace and a spacious deck that feels like you are perched in a treehouse. Kitchen has new granite counters and all stainless appliances. The open living space embraces its chalet roots with natural wood and bright natural light. Four bedrooms with large closets allow you and your guests to stay comfortably. A detached, oversized one-car garage with a large loft provides ample room for your workshop and all your outdoor gear and storage needs. Located minutes from Sugarbush Mountain Resort, Mad River Glen, and everything the Mad River Valley has to offer, this property is a must-have mountain escape. Whether you are looking for a year-round home or seasonal retreat don’t let this one pass you by. STRONG vacation rental options for when you are not using it. Sold TURNKEY fully furnished !

Welcome to Estes Landing! This brand new flat style home with a 5+ Star energy rating is ready for you to move in. You will find great attention to detail and high quality finishes throughout. The open floor plan is ideal for family gatherings or entertaining guests. This 1-story home features a primary bedroom suite with a walk-in closet. There are two more bedrooms, another full bath, mudroom, laundry, and an attached 2-car garage. The entire home is equipped with a multi-zone heat pump and a pair of Lunos E2 ventilation fans to keep you warm in the winter and cool in the summer, all while being ultra-efficient. The living room also has a pellet stove for additional warmth and ambiance. Estes Landing combines desirable single family home living with the convenience of condominium-style exterior grounds maintenance and services. The best of both worlds!

Welcome to Estes Landing! This brand new flat style home with a 5+ Star energy rating is ready for you to move in. You will find great attention to detail and high quality finishes throughout. The open floor plan is ideal for family gatherings or entertaining guests. This 1-story home features a primary bedroom suite with a walk-in closet. There are two more bedrooms, another full bath, mudroom, laundry, and an attached 2-car garage. The entire home is equipped with a multi-zone heat pump and a pair of Lunos E2 ventilation fans to keep you warm in the winter and cool in the summer, all while being ultra-efficient. The living room also has a pellet stove for additional warmth and ambiance. Estes Landing combines desirable single family home living with the convenience of condominium-style exterior grounds maintenance and services. The best of both worlds!

NEW CONSTRUCTION... Just ten minutes to the base of Sugarbush Resorts and Mad River Glen! Experience awe-inspiring year-round views of the Mad River Valley and direct access to the VAST Trail System. Crafted by Vermont Signature Homes of Waitsfield, this home is under construction and will be move-in ready by Fall 2025. The subject home is a 3 bedroom, 2 bath townhouse featuring turn-key living! Enjoy a single-level floor plan with meadow views from every window. Offering an array of standard features including radiant hydronic heating system, oversized Harvey triple pane double hung windows, open floor plan, and garage parking! The unfinished lower level is ripe for expansion. The primary bedroom suite has a private bathroom, walk-in closet, and courtyard views. Two additional bedrooms are ample-sized and have plenty of storage. A spacious living/dining/kitchen area offers a welcoming space to unwind or host your guests. Make this home yours today!