Properties Near 5 N Main Street Wilmington, VT

Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows that frame the mountain landscape, a cozy stone woodburning fireplace in the great room, open kitchen with gas range and breakfast bar, beautiful sunlit dining area surrounded by glass and a private rear covered deck perfect for relaxing and grilling year round. The main floor includes two comfortable bedrooms and a bath. Upstairs, a spacious open loft with vaulted beamed ceiling leads to a serene primary suite with walk-in closet, private balcony, and spa-style bath with jetted tub and oversized shower. Downstairs, the finished lower level offers even more, welcoming mudroom entry, large family room with brick fireplace, game room complete with pool table and wet bar, bath, laundry room, utility room, and an on-demand generator for peace of mind. As part of the Chimney Hill community, enjoy access to a Clubhouse with indoor & outdoor pools, fitness center, game & media room. hiking trails, ice rink, and direct VAST snowmobile trail access. Located minutes from Mount Snow and Wilmington’s village shops & dining, this is the ultimate Vermont getaway or full-time residence.

Multi-Family & Commercial Opportunity in Wilmington, Vermont Set on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing. The main building features updated interiors with modern kitchens, stylish baths, and new flooring throughout, combining contemporary finishes with a convenient, low-maintenance layout. The property has also been upgraded with a brand-new five-bedroom septic system, providing peace of mind and long-term value. Behind the main residence sits a spacious three-bay garage with a full upper level, ideal for a workshop, contractor space, or additional storage. A smaller outbuilding nearby offers even more flexibility for tools, recreational gear, or seasonal items. Whether you’re seeking an investment property, a home with income potential, or a commercial space with ample storage, this Wilmington location offers endless possibilities just minutes from Mount Snow Resort, Lake Whitingham, and the shops and dining of downtown Wilmington. On the MooVer Route

Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 3 bedroom home plus bonus room offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings, rich natural woodwork, gorgeous wood flooring, and a stunning timber frame beam. A dramatic south-facing wall of windows floods the home with natural light, while the stone-faced woodburning fireplace creates the perfect après-ski atmosphere. The kitchen is built for entertaining with granite countertops, a large seating island, stainless appliances, and abundant cabinetry. You’ll also find a custom bar area, full bath, ensuite bedroom, and easy access to both the covered front porch and new back deck with hot tub. Upstairs offers two spacious, light-filled bedrooms and a full tiled bath. The lower entry level is built for real mountain living with radiant heat throughout, a showpiece tiled mudroom with cubbies, benches, shelving, and storage baskets, plus a laundry room with counters, cabinets, and sink. A full tiled bath with double sinks, bonus room with proper egress window, and a massive den/game room featuring pool table, darts, basketball setup, ping pong, living area, custom art, and sliding barn door complete the space. Outside, enjoy the new huge back deck with hot tub, ski lift chair feature, and additional rear deck space, plus covered front porch and outdoor lockable ski storage. The home is tastefully furnished throughout and features central vacuum & smart features for interior/exterior lights, thermostats, hot tub, keyless entry. Chimney Hill offers true four-season amenities including a clubhouse w/ indoor/outdoor pools, hot tub, sauna, fitness room, game room, lounge, tennis, pickleball, ice skating, hiking trails, and snowmobile access.

Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen with custom cabinets, stainless appliances, and soapstone counters, large living room with wood burning fireplace and stone hearth from Parmelee and Howe soda counter, large pantry, mudroom, main floor full bath with laundry, one car garage with bonus storage, updated flooring and specialty lighting fixtures, and the list goes on. There are 4 bedrooms en suite, including a newly added primary suite with tiled bath with steam shower, family room with custom walnut built-ins and wet bar, as well as minisplit A/C. Take in your morning sun from the covered front porch, or enjoy soaking in the hot tub off the large rear deck surrounded by stone walls, perennial gardens, and mature trees. A backyard oasis with a surprisingly private yet convenient location. Less obvious features include standing seam metal roof, updated utilities, full basement, second laundry location, paved driveway, freshly painted exterior, fiber internet, and town water & sewer for total peace of mind. A welcome respite from metropolitan life or potentially a great rental opportunity.

Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool table, and additional sleeping space—perfect for hosting, relaxing, or entertaining guests. All contents of the residence are included with the sale. At the front of the building, approximately 800 sq ft of high-visibility commercial space is occupied by an established business, making this property ideal for investors, entrepreneurs, or those looking to combine lifestyle and income. Great location for a re-locating professional. With a prime location within walking distance to restaurants, shops, and trails; convenience is unmatched. The property underwent an extensive transformation by the owner who is also an award winning architect, blending rustic Vermont charm with modern comfort. Exposed beams, wide plank floors, deck and multiple bedrooms create a warm and inviting atmosphere across multiple spacious living zones.

Beautiful 2010 post and beam home just a short drive from the Mount Snow Ski Resort and village of Wilmington. This meticulous turn key home was built with quality in mind, is very energy efficient and sits on a on a private 5+ acre parcel abutting a stream just up from Spruce Lake. Inside is a gorgeous great room space with vaulted ceilings and exposed natural woodwork, great natural light thanks to large windows, and a Vermonty rustic feel, wood floors and radiant heat throughout, a wood burning fireplace with stone hearth, exposed beams, upscale kitchen with custom cabinets, stainless appliances, and granite counters, large dining area, half bath for convenience, a main floor primary suite with full bath, additional primary second floor suite suite with vaulted ceiling and luxurious bath, 3 more upstairs bedrooms as well as a full bath, the 3rd floor bedroom could double as a family room, a walkout lower level with oversized garage for toys and cars, as well as a main floor large mudroom for all your gear. There is also a spacious patio for entertaining with BBQ area and hot tub, ample level lawn space for play or fire pit, and large driveway for easy parking. This home has strong rental history so could serve as your home away from home as well as an investment to offset costs, affording you downtime, not upkeep.

Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and exposed natural woodwork, great natural light thanks to large windows but with a Vermonty rustic feel, wood floors throughout, a gas fireplace with stone hearth, updated kitchen with custom cabinets, stainless appliances, and quartz counters, dining area, a main floor primary suite with full bath, a main floor office, an upstairs guest room, a bunk room, as well as a full bath, a fully finished walkout lower level family room with gas stove, billiard area, custom ski room with cubbies and coat racks, full updated bath, entry foyer, as well as a main floor large mudroom. There is also a spacious double deck for entertaining, great lawn space, and large drive for ample parking. This includes the amazing Chimney Hill amenities of indoor and outdoor pools, clubhouse, theater, gym, hot tub, basketball court, tennis courts, winter ice skating, and a la carte services like plowing and trash, to afford yourself plenty of downtime, not upkeep.

Beautiful upscale chalet in the Chimney Hill community just a short drive from the Mount Snow ski resort and the village of Wilmington. This meticulously maintained turnkey home has been extensively renovated and upgraded, and sits on a private lot along a quiet side road with direct access to nearby snowmobile trails. Inside, a gorgeous great room features vaulted ceilings, exposed natural woodwork and beams, wood floors throughout, and abundant natural light from large windows — creating a warm and inviting Vermont mountain feel. A wood-burning fireplace with floor-to-ceiling stone hearth anchors the living space. The updated kitchen includes custom cabinetry, stainless appliances, and quartz countertops. The main level also offers a primary suite with full bath and jetted tub, two additional bedrooms, a full bath with tiled shower, and a functional mudroom entry designed for four-season gear. A cozy loft above provides ideal office or reading space. The fully finished lower level features a spacious family room with game area and wet bar, an additional sleeping area, and a third full bath with tiled shower. Outside, enjoy a large deck for entertaining, an outdoor hot tub for relaxing after a day on the trails, fire pit area, and a generous driveway with ample parking. A nearby overflow parking area accommodates snowmobile trailers or boats in the summer months. Chimney Hill amenities include indoor and outdoor pools, clubhouse, theater, fitness center, hot tub, basketball court, tennis courts, and winter ice skating, with optional services such as plowing and trash removal — allowing for downtime, not upkeep. Septic system is sized for three bedrooms. Lower-level sleeping area does not have legal egress.

Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous westerly views over Haystack Mountain for sunsets year round. Inside you are treated to a warm living area with natural wood post and beam joinery, beautiful light through the many updated windows, a gas burning stove for easy ambiance, a gorgeous updated kitchen with stainless appliances and granite counters, spacious dining area which leads out to the side dining deck for entertaining, family room addition with vaulted ceiling, exposed beams, and half bath, main floor primary suite also with vaulted ceiling and spa-like full bath with soaking tub, double vanity, and tiled stand up shower, a walk-in closet with custom shelving, main floor laundry and pantry space, dual upstairs bedrooms with shared full bath, a full lower level with workshop and updated boiler, double mudroom entry with ample gear storage, and perennial landscaping. The original plans called for a garage addition which would be easy to add on, and the lovely landscaped open lot gives you plenty of options. A truly Vermont style home that works perfect as a weekend getaway, or retirement downsizing option.

Discover the Best of Southern Vermont Living! Nestled in a bucolic country setting, this versatile property offers breathtaking views of a neighboring classic Sugar House and a large beaver pond that is the headwaters of the Green River. Whether you're seeking a serene country retreat, a dedicated ski house, or a comfortable year-round home, this classic cape checks all the boxes. The bright, two-story home provides flexible living arrangements with five spacious bedrooms—three upstairs and two downstairs. This layout is perfect for accommodating guests, a home office, or planning for comfortable multi-generational use. The garage includes a large, insulated room above that has tremendous potential for a studio space. Ideally located for both recreation and relaxation, the home is a quick 20-minute drive to Mount Snow. Direct access to VAST trails and local hiking and mountain bike trails abound. Enjoy easy access to the charming towns of Wilmington, Dover & Brattleboro, as well as to natural attractions such as Lake Raponda and Harriman Reservoir. You are also just minutes from the renowned Marlboro Music Festival, now in its 76th year. With effortless access from Connecticut, Massachusetts, and New York, this home offers the perfect blend of natural beauty, flexibility, and convenience. Experience the tranquil beauty and vibrant lifestyle of Southern Vermont! The current owners have used it as a very successful rental property for many years.