Properties Near 6 Longest Drive Wilmington, VT

Set at the end of the road and lower on the hill, this chalet-style home offers many of the features buyers consistently look for in Chimney Hill. The thoughtfully designed mudroom entry includes a custom live-edge wood bench by Vermont Live Edge, along with ski, coat, and storage racks—ideal for Vermont’s four-season lifestyle. The home features three levels of living space. The ground level includes an extra living space room, laundry area, bunk room, full bath, and access to the outdoor fire pit. The main level offers two bedrooms, a full bath, and an open-concept living, dining, and kitchen area with cathedral ceilings, an island, and sliders leading to the view rail deck. A loft provides additional flexible space for guests or entertaining totaling 3 different hangout spots! Ownership includes access to Chimney Hill’s 1,200-acre, all-season resort campus and clubhouse. Amenities include indoor and outdoor heated pools, a hot tub, arcade room, children’s playroom, members’ lounge, community room, reading nook, fully equipped kitchen for HOA member use, outdoor grill area, playground, basketball and tennis courts, and an extensive multi-use trail system supporting hiking, biking, snowmobiling, cross-country skiing, seasonal pickleball, and ice skating. Additional shared amenities include a fishing pond, lookout areas, and trail access toward Haystack Mountain.The surrounding Deerfield Valley and Southern Vermont region offer year-round recreational opportunities including skiing, golf, boating, hiking, paddleboarding, access to the Green Mountain National Forest, along with local music, festivals, breweries, distilleries, shopping, and a wide range of dining options.

Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning fireplace, and updated main-level flooring. The kitchen offers a breakfast bar and gas range, while the dining area flows seamlessly into the living space. Upstairs, the open loft bedroom includes a private updated bath with oversized shower. The lower level provides a generous primary suite with jetted tub, two additional bedrooms, full hall bath, and laundry area. A covered porch entry with mudroom keeps golf and ski gear organized. The association handles exterior maintenance, landscaping, snow removal, and even delivers firewood to your door for true ease of ownership. Located just steps from golf, a short drive to Wilmington’s shops and restaurants, minutes from Lake Whitingham, and within easy reach of both Haystack and Mount Snow ski resorts, this townhouse is the ideal four-season getaway.

Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use trail system for biking, hiking, snowmobiling, 3 areas with tennis courts, seasonal pickleball and ice skating, year-round swimming at the Exclusive Members-Only Club House , indoor and outdoor in-ground pools, hot tub, fitness room, arcade room, small child playroom, community room, table tennis, basketball, fully-equipped kitchen for HOA members use, outdoor grill by the outdoor pool, along with a playground for young children, and members lounge. Plus, world class skiing and shredding just minutes away, golf, boating, fishing, paddleboarding, unique shops, fine dining, flea markets, festivals, music, and all the Deerfield Valley and Southern Vermont have to offer! Own this winter don't rent!!!

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 Raponda in Wilmington. Just a short stroll along the community trail through the woods leads you to a private association beach with a dock and kayak racks—ideal for swimming, paddling, boating and enjoying peaceful lakeside moments. Outdoor enthusiasts will also love the easy access to the nearby VAST snowmobile trails. Conveniently located only minutes from Mount Snow for skiing and year-round recreation, and just a short drive to the shops and restaurants of downtown Wilmington. Whether you're looking for a full-time residence or a weekend escape, this property offers a perfect blend of lake and mountain living.

Beautifully positioned along the 11th fairway of the Haystack Golf Course, this contemporary 3-bedroom, 4-bath townhouse offers four-season comfort with gorgeous mountain and sunrise views. The bright main level features an open layout with vaulted ceilings, a wood-burning fireplace, contemporary kitchen with breakfast bar, and a spacious dining area overlooking the outdoors. The primary suite is a true retreat with a gas fireplace, walk-in closet, and spa-like bath with jetted tub and separate shower. A guest bedroom, full bath, laundry, and a shared sunroom opening to a private patio provide inviting all-season living. Upstairs, a generous open loft with vaulted ceilings and its own bath offers ideal space for guests, work, or relaxation. Additional conveniences include a large mudroom entry, outdoor ski locker, and easy access to the deck and patio for year-round enjoyment. Just minutes to the Hermitage Club, Haystack Golf Course, Mount Snow Resort, local lakes, trails, and the village of Wilmington, this turnkey condo delivers low-maintenance living in a quiet, welcoming atmosphere. Being sold furnished excluding a few personal items.

Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with exposed natural woodwork and great lighting. There is a cozy living room with gas stove, wood floors, kitchen with island, dining area which has a slider leading out to the entertaining deck, a full bath, and two nice bedrooms. The finished walkout lower level has a family room and game room entertainment area, wood stove for supplemental heat, third bedroom, and second bath, as well as a functional mudroom entry off the driveway. Additionally there is a shed great for seasonal gear storage or snowmobiles, a large upper lawn space for outdoor enjoyment, and a nicely graded driveway. Recent upgrades include a minisplit heating and cooling system, Rinnai direct vent propane heater, and more. The property is in the desirable C section making it easy to access no matter the weather. It comes with all the great amenities including clubhouse, indoor and outdoor pools, hot tub, locker room, gym, game room, theater, basketball court, tennis court, ice skating, and a la carte services such as plowing, sanding, and trash.

Welcome to 60 Higley Hill — a well-equipped country home on just over 5 acres, offering comfort, convenience, and value in one of Dover’s desirable areas. The property features a standing seam metal roof, a brand-new septic system, and a 600-ft well drilled within the last 10 years, providing peace of mind for water and waste systems. Inside, enjoy the convenience of a first-floor bedroom, a main-level living area with a beautiful two-sided fireplace, stainless steel appliances and a full unfinished basement — also with a fireplace — offering flexibility for future added living space or storage. Additional features include a French drain around the home, a new electric panel, and a generator switch for power back-up. Outside, the land offers established fruit trees, blueberry bushes and ample garden space ideal for planting, harvesting or simply enjoying. A spacious garage adds practical storage or workspace. With strong infrastructure, thoughtful upgrades, and move-in ready conveniences, this home offers rare value and versatility at a great price in Dover.

Charming Rustic Country Saltbox on Lower Chimney Hill Nestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round. Outdoor enthusiasts will love the easy access to snowmobile and hiking trails, including a nearby trailhead to Haystack Peak. Enjoy close proximity to Lake Whitingham and the Village of Wilmington, offering dining, shopping, and four-season recreation just minutes away. Recent updates add peace of mind, with the roof, windows, and furnace all replaced within the past five years. Whether you’re looking for a full-time residence or a Vermont getaway, this property blends rustic character with modern improvements in an ideal location.

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!

Turn key renovated 3+ bedroom, 2.5 bath townhouse just off the Haystack Golf Club 10th hole, with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club and Mount Snow ski resorts. This unit has been completely renovated throughout and is being sold for immediate enjoyment. Features include a vaulted living room area with stone fireplace, great natural light through many large windows, a spacious dining area with slider out to the entertaining deck, safe from errant balls, a new custom kitchen with quartz counters, stainless appliances, and custom cabinets, guest half bath on the main floor, and a large mudroom for all your gear no matter the season. Upstairs is a sleeping loft currently being used as a family room complete with sleeper sofa, games, television, and owners closet. The lower level has a primary bedroom suite with tiled bath and barn door feature, there is a second bunk room with futon, as well as a bonus room currently set up for more sleeping, and a 3rd full bath with stand up shower. Amenities include snow removal, landscaping, building maintenance, and trash. There is an ongoing project to replace windows and siding that will ultimately improve the overall exterior aesthetic, and has been factored into the price. Easy access to and from the adjacent golf course, which is great for trail access for hiking and cross country skiing year round, as well as the nearby Hermitage Club and Mount Snow ski resorts, and nearby village of Wilmington. A great price for great space!

Charming country cape just outside the village of Wilmington on a spacious corner parcel with easy access off Rte 9. This lovely home could be a great full time residence or vacation retreat, thanks to a great price, great bones, recent upgrades, and nearby lakes, skiing, villages, and Molly Stark State Park right across the street. The house has a bright south facing living room, country kitchen with breakfast table and functional space, two main floor bedrooms and a full tiled bath, 2 upstairs bedrooms and a half bath, wood floors throughout, a full basement entry level with tiled bonus space, laundry room, and mudroom entry, and large deck to take in the scenery. There is a detached studio shed for whatever creative outlet you may want, multiple storage sheds, a second driveway to the outbuildings, a lower grassy area leading down to the beaver brook, and nice winter exposure over nearby fields. Recent upgrades include an updated roof, charming Vermont stone walls, updated drainage around the home, and fresh paint. Truly a unique opportunity at a rare price.

Arrive, exhale, and settle into a condo that lives like a true getaway. This light-filled, spacious residence pairs a large open kitchen and dining area with a comfortable living room featuring a wood stove for cozy winter nights after a long day on the slopes! Inside, you will find 3 bedrooms, 3 bathrooms, and 1,440 sq ft designed for relaxed hosting and easy retreat. The open-concept main level floor plan keeps everyone connected, whether you are fueling up before first tracks or lingering over a late dinner after a day outside. Newer kitchen appliances are in place for everyday convenience, while the mini-splits and smart thermostat help dial in comfort before you arrive and maintain it while you are here. Offered with furnishings, this is a rare chance to enjoy a more turn-key start, so you can spend less time planning and more time enjoying your time away. A year-round retreat; step out to the back deck and let the pace slow down. It is the perfect spot for morning coffee in crisp mountain air, a mid-day reset between adventures, or an evening wind-down under the sky. With three bathrooms, guests can spread out comfortably, and you can host without sacrificing privacy, a huge advantage when your favorite people want to join you for ski weekends, golf outings, or long trail days. When it is time to explore, you are close to a golf course and surrounded by activities that make a second home feel worthwhile: hiking trails, snowmobiling, and quick access to skiing in under 10 minutes. Whether you are chasing powder, fairways, or fresh air, the location supports an all-seasons lifestyle that keeps calling you back. With low condo fees, enjoy the Green Mountains with minimal expense and plenty of fun! Come see how easy it feels to own a place where the gear, the gatherings, and the quiet moments all fit.

Owner open to offers. Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are treated to an open concept living space large living and dining areas, wood burning fireplace with stone hearth, new vinyl plank flooring, large kitchen with breakfast bar, primary suite with walk in closet, full bath, stand up shower and soaking tub, guest bedroom with jack and jill bath, nice light throughout, and a covered rear porch to take in the views. There is also a ski locker for gear and ample parking. The Haystack restaurant is currently open year round for dinner, affording a convenient dining option. There is also easy upkeep thanks to community living with landscaping, snow removal, wood, trash service, and more. This one won't last long!

A solid home in a great location in Wilmington Vermont! Currently set up as a duplex. Live in one and rent the other or have family close by! Add internal stairs and use as one! This is a classic Chalet with the ease of a metal roof, large deck, 2 bedrooms and a full bathroom upstairs along with a cathedral ceiling, cute sleeping loft and built ins! The lower level is 2 bedrooms and a full bathroom with large combined kitchen/living and dining room. There is a large wood shed and an even larger garage/shed/barn. Enjoy your days on the oversized front deck and your evenings by the fire pit! The wooded area behind the home is great for exploring! So close to the local towns, ski areas, lakes and ALL!

Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car garage. Wonderful neighborhood on a private road. Nice floorplan!!!

Ready to move in Mountain Ponds end unit Townhouse with 2 bedroom plus loft and 1 1/2 bathsMain level boasts an open concept living/dining and renovated kitchen area. Relax on the back deck off dining area. Gas stove in the living room. Attached ski locker/wood bin with 2 entrances. Spacious mudroom. Direct access to VAST snowmobile trail and adjacent to Haystack Golf Course. Lake Whitingham is nearby for canoeing, boating, kayaking and fishing. Association dues conveniently cover walkwayshoveling, plowing, firewood, landscaping, annual chimney cleaning, and trash removal. Perfectly located near Haystack Mountain and a wealth of outdoor recreationopportunities, including hiking, biking, golfing, snowmobiling, and snowshoeing. Downtown Wilmington’s shops and restaurants are just minutes away, and Mount Snowis only 3 miles from your door. Make this inviting townhouse your Vermont retreat.