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32 Steep Hill Rd, Wilmington
$1,998,000
5 Beds ⋅ 5 Baths ⋅ 5097683 MLS
Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont’s Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern Green Mountains. With over 4,200 square feet of thoughtfully designed living space, the interior boasts clean lines, a Primary suite with walk-in closet and spa-like bath. Floating staircase, a large foyer, and a screened-in porch for enjoying warm evenings. Vaulted ceilings, radiant heat throughout, and walls of windows frame the stunning mountain and valley vistas. Open-concept kitchen and dining area with granite countertops, custom cherry cabinets and flooring, large center island, and a massive stone fireplace. Direct access to multi-level decks. Spacious living room with exposed beams and a cozy sitting area with a Projection System and a Custom high-end audiophile Sound system. Oversized heated 3-car garage. Enjoy outdoor living at its best with beautifully maintained flower gardens, open fields, a mature mixed forest, a patio, a hot tub, an outdoor shower, and creek frontage.

32 Steep Hill Rd, Wilmington

286 Coldbrook Rd, Wilmington
$1,400,000
4 Beds ⋅ 5 Baths ⋅ 5073006 MLS
This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder’s allowances or choose upgrades at their expense.

286 Coldbrook Rd, Wilmington

26 Highlands Ave Unit J2, Wilmington
$949,000
4 Beds ⋅ 4 Baths ⋅ 5107242 MLS
Elevated Mountain Living at Haystack Highlands. Discover the ultimate four-season retreat in this exceptional townhome, ideally positioned along the 11th fairway of Haystack Golf Course and framed by distant mountain views. Designed for effortless entertaining and memorable gatherings, this beautifully appointed home offers an exceptional blend of finishes, generous living spaces, and the relaxed elegance of Vermont mountain living. At its heart, dramatic great room makes a striking impression with a soaring 20-foot ceiling, locally sawn timber beams, hardwood flooring, and a wood-burning fireplace the perfect setting to gather after a day on the slopes, the golf course, or exploring the surrounding mountains. Open concept dining and kitchen areas flow seamlessly together, featuring granite countertops, stainless steel appliances, and a welcoming breakfast bar. Step outside to the deck and unwind with a glass of wine. The main level offers the convenience of a laundry room, a bedroom and a full bath. Upstairs, the primary suite provides a serene escape, complete with its own private deck an idyllic spot to savor a quiet morning coffee and a luxurious bath featuring a double vanity, separate shower, and jetted soaking tub. A guest en suite, privately situated at the opposite end of the hallway, features vaulted ceilings and a bath. The walkout lower level is designed with entertaining in mind. A custom bar, granite countertops, wine and beverage coolers, and a dishwasher opens to a spacious family room, creating the ideal setting for gatherings with family and friends. An additional bedroom, full bath, and bonus room provide plenty of flexibility for guests. Mudroom for all your gear, exterior ski closets. Perfectly situated just minutes from the Village of Wilmington, the Hermitage Club, five miles from Mount Snow, this exceptional residence places the very best of southern Vermont at your doorstep.

26 Highlands Ave Unit J2, Wilmington

67 Castle Hill Rd, Wilmington
$747,500
5 Beds ⋅ 4 Baths ⋅ 5089227 MLS
Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham’s boat launch and beach areas - truly four-season enjoyment at your doorstep. Inside, the home offers 4+ bedrooms and 3.5 renovated baths across three distinct living areas. The flexible layout includes a main-floor primary suite option, a second upstairs suite with large closets and an upscale bath, plus a separate guest wing with two additional bedrooms and a full bath - perfect for hosting family and friends. You’ll also find up- and down-country mudrooms with excellent storage, the original foyer and front door, a country kitchen with stainless appliances and Corian counters, gas stove with brick hearth, vintage bar area, wood floors, gorgeous sunroom, and main-floor laundry - blending historic character with everyday convenience. Spacious and bright, the home strikes the perfect balance between timeless charm and modern comfort. Enjoy mountain views over the village from the front porch, or relax among the beautifully crafted stone walls, perennial gardens, and mature trees. Additional features include a newly built two-car garage barn with second-floor expansion potential, fiber internet, town water and sewer, ample driveway parking, and true peace of mind. A welcome respite from metropolitan life - and a level of preserved character rarely found in such pristine condition.

67 Castle Hill Rd, Wilmington

57 Castle Hill Rd, Wilmington
$690,000
5 Beds ⋅ 4 Baths ⋅ 5101430 MLS
Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while the covered front porch invites you to enjoy your morning coffee, curl up for a lazy afternoon, or take in the Fourth of July fireworks. Additionally, two decks provide ample space for lounging, dining, and more. Inside, the home offers a variety of spaces designed to foster togetherness and relaxation. Gather around the fire in the cozy family room for game nights, or retreat to the den for some quiet time with a good book. The great room is perfect for accommodating the entire gang, while the downstairs recreation space, complete with a pool table/ping pong and foosball, promises endless entertainment. With five bedrooms and several bonus rooms, everyone can enjoy their own private retreat. A Vermont room upon entry to the lower level provides storage for coats, boots, gear, and more. The original structure is complemented by an 840 square-foot permitted addition, which includes a two-car garage, deck, great room, and one of the bedrooms and bathrooms. This home is ideally situated close to town, allowing for easy access to shops, restaurants, village events, and public transportation. It's also just a stone's throw from Harriman’s Reservoir, where you can indulge in boating and swimming. Whether you envision this as your primary residence or vacation getaway, "Pipe Dream" has everything you need. Its prime location offers easy access to Mount Snow Resort and the Hermitage Club for skiing and snowboarding, as well as Mount Snow and Haystack public golf courses. Consider making this extraordinary house your next dream home.

57 Castle Hill Rd, Wilmington

44 High Top Rd, Wilmington
$489,000
3 Beds ⋅ 2 Baths ⋅ 5109032 MLS
A true opportunity! Completely renovated chalet in the Chimney Hill community just a short drive from Mount Snow ski resort and the village of Wilmington. Conveniently located with easy access in the B section of Chimney Hill, so no need to worry about driving up the mountain. This 3 bedroom, 2 bath home features extensive upgrades including new kitchen with soapstone counters and stainless appliances, vaulted open concept living room with wood burning fireplace and great natural light and woodwork, wood floors, newly tiled bathrooms, gorgeous mudroom with slate tile and custom cubbies for gear, new rustic furnishings throughout, main floor primary bedroom with en suite bath, large loft great for overflow sleeping, energy efficient propane heating system, and spacious deck for entertaining. Less obvious upgrades include updated washer and dryer, a standing seam metal roof, updated septic tank, shed for gear, and home generator. This comes with the tremendous Chimney Hill amenities including renovated clubhouse with indoor and outdoor pools, hot tub, gym, arcade, game room, theater, tennis courts, winter ice skating, and a la carte services such as plowing, mowing, trash, and more!

44 High Top Rd, Wilmington

216 Ghastly Job Way, Wilmington
$460,000
3 Beds ⋅ 2 Baths ⋅ 5096572 MLS
Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind surrounded by nature. Inside, the inviting open-concept living space features a cozy pellet stove with a convenient lift system for easy refilling from the lower level. The main floor offers a primary bedroom, full bath with laundry, and a spacious mudroom designed for four-season living. Upstairs, you'll find two additional bedrooms and a second bath, providing comfortable accommodations for family and guests. The walkout lower level includes utility space and a two-car garage, with excellent potential for a future family room, recreation space, or home gym. Outdoor amenities include a firepit gathering area, perfect for relaxing evenings under the stars while enjoying the peaceful mountain setting. Conveniently located just minutes from Wilmington's shops and restaurants, Lake Raponda, and Molly Stark State Park, this move-in-ready property offers the perfect balance of privacy, recreation, and Vermont charm. Whether you're seeking a year-round residence, vacation home, or mountain escape, this exceptional property is ready to be enjoyed.

216 Ghastly Job Way, Wilmington

555 Vt Route 9, Wilmington
$424,990
3 Beds ⋅ 2 Baths ⋅ 5069461 MLS
Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating a private retreat. Whether you’re a winter sports enthusiast, a lover of water activities like kayaking, paddleboarding, and fishing, or simply seeking a peaceful escape, this location is a gateway to year-round adventure. Explore skiing and snowboarding, hike and bike scenic trails, or enjoy the vibrant local food and arts scene in nearby downtown Wilmington. Imagine the possibilities: your dream home, an income-producing property, or a combination of both, all in a setting that perfectly captures the beauty and charm of Vermont.

555 Vt Route 9, Wilmington

3 Woodchuck Ln, Wilmington
$399,000
4 Beds ⋅ 2 Baths ⋅ 5106862 MLS
Woodsy and charming ski chalet just a short drive from the village of Wilmington and Harriman Reservoir, and 10 minutes to the Mount Snow ski resort. This home sits on a private wooded lot, nestled in the Chimney Hill community with easy access thanks to a circular driveway, and just down the hill from the amenities building. The home has been partially updated and cared for and features a large living room with exposed woodwork, great natural light from the large windows, a wood burning stove and brick hearth, spacious dining area which leads into the large kitchen, media room which could serve as a main floor bedroom, large mudroom entry with ample gear storage and full bath, and spacious deck for entertaining. The upper level has 4 vaulted bedrooms as well as a second full bathroom. There is a full walkout lower level for tremendous expansion potential. The siding was redone in 2024 and new insulation was installed in the upstairs walls. Includes the tremendous Chimney Hill amenities consisting of indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep.

3 Woodchuck Ln, Wilmington

250 Fairview Ave, Wilmington
$349,000
2 Beds ⋅ 2 Baths ⋅ 5108158 MLS
OPEN HOUSE: Sunday, 9/6 - 11-1pm. Tucked privately down a treelined driveway, this well built 2 bedroom, 2 bath home offers a cozy Vermont lake and mountain retreat, within a minute drive and just a short walk from Lake Whitingham. Built just 11 years ago, the home is a manageable size, and makes great use of its space with warm wood finishes, vaulted ceilings, abundant natural light, and a comfortable, inviting layout. Heating and cooling provide year round comfort, while the deck offers a great spot to relax and enjoy the peaceful wooded setting. The home offers a mudroom entrance and a main level bedroom and bath. Upstairs, an open concept living room and kitchen opens up to the deck. An additional bedroom and bath round out the home. The storage shed adds extra space for lake gear, bikes, tools, and outdoor equipment. Private from the road yet close to recreation, this cute home is an easy to maintain option for a primary residence, Vermont getaway, or weekend escape. The lake life you've been dreaming about awaits you with beach access, picnic area and boat launch right there. The center of Wilmington and Mount Snow ski area are just down the road, offering you the best of Vermont's four seasons lifestyle.

250 Fairview Ave, Wilmington

1 Frog Holw, Wilmington
$329,000
3 Beds ⋅ 2 Baths ⋅ 5073620 MLS
Nestled in a convenient Lower Chimney Hill location, this charming country saltbox offers classic Vermont character, cozy comfort, and access to the many benefits of the Chimney Hill community. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace, the home provides a warm and inviting atmosphere for year-round enjoyment. Recent updates, including the roof and windows, add peace of mind while maintaining the home’s rustic Vermont character. One of the highlights of owning in Chimney Hill is the extensive array of amenities designed for all ages and generations. The exclusive Clubhouse features indoor and outdoor heated pools, a hot tub, fitness center, arcade, toddler playroom, après-ski lounge, community room, and fully equipped kitchen. Additional recreational amenities throughout the community include Duck Pond, playgrounds, tennis and pickleball courts, basketball, and a lighted seasonal outdoor ice-skating rink with a warming hut. An extensive trail system provides opportunities for hiking, biking, snowshoeing, and cross-country skiing. Chimney Hill also offers valuable community services, including road maintenance, plowing, driveway sanding, and firewood delivery, adding convenience to Vermont homeownership. A weekly community news update keeps owners informed about activities, events, and happenings both on the Hill and throughout the surrounding area. Community amenities, and the convenience of a well-established and professionally managed association all in an ideal Southern Vermont location.

1 Frog Holw, Wilmington

5 Camelot Dr, Wilmington
$269,000
3 Beds ⋅ 2 Baths ⋅ 5098068 MLS
Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy trips to Mount Snow. The property features public water and sewer, a garage, paved driveway, two storage sheds, and plenty of lawn and garden space for outdoor enjoyment. Located just off a paved town road, you'll appreciate the quiet surroundings without sacrificing accessibility. Inside, you'll find generous living space with room to spread out, making it an ideal year-round residence or weekend retreat. Whether you're buying your first home, downsizing, or simply looking for an affordable way to enjoy all that Southern Vermont has to offer, this property is worth a look. With a motivated seller and a location that's hard to beat, this is an opportunity you won't want to miss.

5 Camelot Dr, Wilmington

Happy Haven Rd, Wilmington
$115,000
5097175 MLS
Beautiful 5-Acre Vermont Lot with Mountain Views & Potential for Two Home Sites. Discover a rare opportunity to own a stunning 5-acre parcel in southern Vermont, ideally located on Route 100 just north of downtown Wilmington. This exceptional property offers the perfect setting for your dream home or the potential to build two. Preliminary soil testing supports the potential for two separate single-family home sites, each accommodating up to a 3-bedroom residence, making this an attractive opportunity for homeowners, family compounds, or investment. The property features a beautiful open meadow bathed in sunshine, gently rolling terrain, and breathtaking views of the surrounding mountains and the Deerfield River. As a corner lot with road frontage on two sides, it offers convenient access and excellent flexibility for future development. Utilities are readily available at the road, including: Electric, Fiber-optic internet and telephone service. The property is also served by the MOOver public bus route, providing added convenience. Just minutes from downtown Wilmington, you'll enjoy easy access to charming local shops, restaurants, schools, and year-round recreation. Nearby you'll find lakes, golf courses, hiking trails, and some of southern Vermont's premier ski resorts, making this an ideal location for both full-time living and seasonal getaways. Whether you're envisioning a private mountain retreat, a family compound, or two thoughtfully positioned homes, this remarkable property combines natural beauty, development potential, and an unbeatable location. Don't miss this rare opportunity to build in one of southern Vermont's most desirable destinations.

Happy Haven Rd, Wilmington

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