Wilmington, VT Houses for Sale

25 private acres with lake frontage, stunning lake & mountain scenery, and a beautifully maintained 3,300+ sq ft home w/ direct-entry 2-car garage. Located in private Spruce Lake Estates—close proximity to Mount Snow & Hermitage Club, State Parks, restaurants, shops and public transportation—this rare property offers 4-season living w/ space, privacy & frontage on a non-motorized lake w/ beach,

Jacki Murano Southern Vermont Realty Group

Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Snow, snowmobile trails, 2 golf courses, historic village, and lake. Double lot w/sounds of Two Brook off back of home, patio, & hot tub, there is a newly updated chef's kitchen and accompaniments, plenty of room for diners, lovely gas fireplaces in both the large living room, and even larger family/game room.

Michael Purcell Berkley & Veller Greenwood/Dover

Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living,

Sigrid Pickering Chimney Hill Realty

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled on a serene wooded lot in the Chimney Hill community. Set back from the road for added privacy, this home offers a perfect blend of comfort and style. As you step inside, a spacious two-room addition, currently used by the seasonal owners for additional sleeping, expands the living space to over 2,100 square feet. The

Patricia Fitzpatrick Skihome Realty

Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

Leslie Fraser Four Seasons Sotheby's Int'l Realty

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

Monique White Deerfield Valley Real Estate

Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

John Redd Skihome Realty

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

Adam Palmiter Berkley & Veller Greenwood/Dover

Nestled up against the tree line, this 3 bedroom 2 bath home offers a slice of privacy at the end of a dead-end road near the top of Chimney Hill. The current owner has opened the yard to let in more light and make it much more user friendly and functional. The driveway was expanded into a circular drive-through. Reduce your electricity costs with the new PV solar array on the roof that will

Jim Bellville Bellville Realty

This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

Adam Palmiter Berkley & Veller Greenwood/Dover

Somerset Wilderness,Close to the reservoir and Deerfield River. Boating. snowmobiling, hunting, and hiking. Open land with trails and apple trees. Abuts the National Forest.

Mark Yule BHG Masiello Brattleboro

Just a half mile from The Hermitage Club, 3.5 miles to Mount Snow, and only a mile from Haystack Golf Club, this 4 bedroom, 3 bathroom home on 10.1 acres offers the perfect blend of rustic charm and modern comfort. Direct access to the VAST snowmobile trails and mountain views makes this an outdoor enthusiast’s dream.Step inside to find warm wood finishes, exposed beams, and rich natural textures

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight

Sigrid Pickering Chimney Hill Realty

This well-maintained 3 bedroom, 2 bath chalet in the sought after Chimney Hill community offers three levels of thoughtfully designed living space, providing plenty of room for the entire family. Recent improvements include a new roof in 2024, freshly painted exterior, and a recently stained deck, ensuring the home is move-in ready. The open concept main floor features an updated kitchen with

Prema Fitzpatrick Skihome Realty

Charming Saltbox Chalet located in the desirable Chimney Hill community. This classic chalet is just a short drive from Wilmington Village, Lake Whitingham, the Haystack Golf Course, and Mount Snow Ski Resort. The light-filled interior offers a welcoming open concept great room with vaulted ceilings, a wood-burning fireplace with brick hearth, and hardwood flooring. The kitchen features granite

Monique White Deerfield Valley Real Estate

Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

Janet Boyd Boyd Real Estate

Welcome to Chateau Chelsea! This charming three-level, 4-bedroom, 3-bathroom single-family home is situated in the heart of Vermont’s picturesqueGreen Mountains. Named after the owners' beloved pup, this property has been a cherished gathering place for family and friends year-round. Conveniently located just over 2 hours from Boston, 90 minutes from Hartford, CT, and less than 4 hours from NYC,

Patrice Schneider Southern Vermont Realty Group

This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

Jennifer Hovey-Densmore Deerfield Valley Real Estate

Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

Monique White Deerfield Valley Real Estate

Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

Adam Palmiter Berkley & Veller Greenwood/Dover

Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

Adam Palmiter Berkley & Veller Greenwood/Dover

This house sits on a lot that is surrounded by common land so it feels very secluded and private. Newer septic, roof, and main level flooring, and the prior owner did a lot of custom wood paneling with built-ins, and creative decorating which add to its charm. The main level has a mudroom entry with laundry and storage space, full bath, kitchen with open shelving above and cabinets below, newer

Sigrid Pickering Chimney Hill Realty

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

Adam Palmiter Berkley & Veller Greenwood/Dover

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

Morriah Adams BHG Masiello Brattleboro

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

Jennifer Hovey-Densmore Deerfield Valley Real Estate

This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

Jennifer Hovey-Densmore Deerfield Valley Real Estate

“The Camp” Are you looking for that special seasonal getaway? Look no further! This charming 1-bedroom on the main level and second bedroom upstairs sleeping loft is located in the beautiful town of Wilmington. Nestled in the woods, this cozy cabin offers a unique and special Vermont experience. Enjoy the covered front porch and large deck, perfect for entertaining friends and family. Just steps

Richard Caplan Deerfield Valley Real Estate

Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s

Jason Saphire www.HomeZu.com

Here is a chance to own a home directly across the street from the private Hermitage Ski Club with easy access to the resort, snowmobile trails, the Mount Snow ski resort, nearby country villages for shopping and dining, and gorgeous area lakes. This lovely renovated chalet sits on a level with ample parking thanks to a circular driveway, winter exposure to Haystack Mountain Peak, a shed for

Adam Palmiter Berkley & Veller Greenwood/Dover

Seeking an upscale but also rustic, Vermont retreat? Looking for privacy but convenience to amenities? Love a water feature and a mountain view? Need a place to host large gatherings but also cozy enough for a romantic weekend getaway? This is just the place. Tucked away on a private road sits this spacious 4 bedroom, 3.5 bath, true log home with an excellent layout over 3 finished floors. All

Jacki Murano Southern Vermont Realty Group

Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

Adam Palmiter Berkley & Veller Greenwood/Dover

Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds.Boasting a coveted southeast exposure, the home and land are cheerful

Melissa Ellis Southern Vermont Realty Group

Just completed in July 2025, this striking 4-bedroom, 4-bathroom mountain modern home offers over 4,000 square feet of thoughtfully designed living space perched in the desirable Chimney Hill community in Wilmington, Vermont. Set on a 1 acre lot surrounded by mature trees, the home captures a glimpse of the Green Mountains and offers direct access to year-round recreation.Step inside to soaring

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept

Chad Lackey Deerfield Valley Real Estate