Properties Near 22 Hillside Drive Wilmington, VT

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.

Situated in the highly sought-after Chimney Hill Resort community of Wilmington, Vermont, this versatile property offers a unique opportunity for vacation living and rental income. The chalet-inspired main home features an open floor plan with soaring ceilings, an upgraded kitchen with smart home features, and seamless access to a wraparound deck surrounded by mature woods. A detached garage adds functional value for storage, equipment, or recreational gear, ideal for four-season living. The home is equipped with a whole-house backup generator and modern appliances for turn-key ownership. Outdoor adventure begins onsite with direct snowmobile trail access and continues nearby with Mount Snow skiing, hiking, and lake activities. Residents also enjoy access to Chimney Hill's indoor pool, fitness center, trails, and year-round recreational amenities. Offered mostly furnished and fully equipped for immediate enjoyment or income generation, this rare Vermont property offers an exceptional blend of private retreat and high-demand rental potential in a thriving four-season destination.

Located across the road from The Hermitage Club at Haystack Mountain, only 5 minutes to Mount Snow and just 30 to Stratton, this single-family home offers the perfect blend of rustic charm and modern comfort. Set on 1.55 acres with a large, level yard and ample road frontage, the house sits well back from the road for privacy and a peaceful setting. Inside, the fully renovated first floor offers updated bedrooms and baths, while the second floor features an open-concept kitchen, living, and dining area—highlighted by original log-style details and an oversized stone fireplace. A second fireplace on the main level adds extra coziness to the bonus living room area. With 6 spacious bedrooms, this home is ideal for hosting family and friends. Whether you're into skiing, snowmobiling, golf, hiking, or lake life, this property is a true year-round retreat. With its unbeatable location, inviting layout, and a mix of modern updates and rustic character, this home is a fantastic opportunity—perfect as a full-time family residence, a vacation getaway, or an investment property.

This reimagined 1970s ski chalet blends timeless architecture with cutting-edge design, offering 4 bedrooms and 3 bathrooms across nearly 4 private acres. Thoughtfully curated for both personal enjoyment and short-term rental potential, the home is turnkey-ready—just bring your suitcase. The entry level features two ensuite bedrooms, each with fully renovated ¾ baths, and a spacious lounge anchored by a dedicated remote-work office nook. Upstairs, an open-concept chef’s kitchen showcases terrazzo tile countertops, premium appliances, and elegant custom finishes. It flows seamlessly into the sun-soaked dining and living areas, with a modern gas fireplace A wall of windows frame breathtaking mountain views. Two additional upstairs bedrooms offer generous closets and share an updated bath with laundry. Throughout the home, sustainable cork flooring provides warmth and comfort underfoot. Designed for year-round enjoyment, the outdoor spaces are equally refined: a lower-level covered lounge, a second-story deck with custom railings, and a secluded backyard fire pit—ideal for stargazing or après-ski gatherings. Smart-home features include app-controlled locks and climate settings for seamless guest access. A two-car garage provides ample storage for skis, paddleboards, kayaks, and more. Whether you're seeking a high-style mountain escape or a revenue-generating rental, this designer chalet delivers effortless elevated living. Delayed showings begin 6.14.25 at open house.

Welcome to 12 Conifer Lane, your private 3 bedroom 3 bath escape in beautiful Southern Vermont. Built with quality construction and a 5 star energy rating, this home is move-in ready and should provide years of stress free ownership. The feeling inside is comfortable and cozy. Cathedral ceilings in the open concept living and dining room are anchored by the wood burning fireplace, making it a great place to unwind and relax after a day on the slopes or at the lake. The large open kitchen is a great space to prepare your meals and includes a breakfast bar, energy star stainless steel appliances, and granite countertops. An ensuite primary bedroom along with another half bath and laundry room round out the first floor for those who need fewer stairs in their lives. Sip your coffee as the morning sun floods the home with natural light, or step out to the back deck to decompress and soak in the new hot tub. It wouldn’t be a quintessential Vermont house without the large mudroom to provide ample space to shed your gear, or the family game room downstairs. There is also an attached heated garage which will make the winters that much easier. Close to Mount Snow, snowmobile trails, hiking, several lakes, and the lovely town of Wilmington, this property provides easy access for you to get out and enjoy the surrounding areas in all four seasons while ensuring a quiet and private sanctuary for you to return home to.

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 shed. Inside is a vaulted great room with natural wood throughout, large windows for natural light, a wood burning stove with brick hearth, kitchen with breakfast bar and stainless appliances, main floor primary bedroom with en suite full bath, two guest rooms and another full bath, a first story family room recently renovated with gas fireplace, large bunk room with attached bath, fifth bedroom with half bath, and large entry mudroom for all your snowy equipment. The home offers ample space for groups, but is intimate and cozy enough for less. A true Vermont style getaway.

Opportunity knocks to put your own touches to this Log home that is studded out and ready to move forward! Amazing location minutes to The Hermitage Club, Mount Snow and Haystack golf which offers golf, snowshoeing and weekend dining! Soaring great room with gas fireplace, three bedrooms, two and one half baths and a large unfinished basement offering many future options. Sale is subject to completion and seller installing water, sewer and all utilities to property. Seller is looking forward to helping you make this your home away from home.

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 kitchen outfitted with high-end appliances and plenty of space for preparing memorable meals. After a day on the mountain or by the water, cozy up around the wood-burning fireplace in the inviting living room, designed for après-ski lounging. With six generously sized bedrooms and four full bathrooms, there’s room for everyone to spread out in comfort. The layout is ideal for multi-generational gatherings, ski weekends, or summer getaways. Located in between Mt Snow and Lake Whitingham this home is a true four-season haven—whether you’re carving powder in winter, hiking or boating in summer, or enjoying foliage and fresh air in between. The property has a septic design for 4 bedrooms, but the house has 6 bedrooms as evidenced by the property cards from both 2019 and 2024. The septic has not failed.

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 space for separation for groups of all ages, young or old. The leach field was replaced when the current owners purchased the home, and an EV charger that was installed is there to charge the electric car drivers in your group. The B section location is so handy to town & the lake at one end, and the clubhouse, golf, or skiing to the north. And then there's all the "other stuff" to do and see nearby!

Gorgeous 2003 post and beam with mountain views and great privacy. This home is located at the end of a quiet road conveniently in the lower section of the Chimney Hill community with a double lot, easy access to Wilmington and Lake Whitingham, and just a short drive to the Mount Snow ski resort and Haystack Golf Club. Inside you are treated to exposed natural woodwork and joinery throughout the true post and beam frame. The main level features a large open concept living room with vaulted ceilings, stone fireplace, large dining and kitchen areas, a main floor master bedroom suite, and half bath, with beautiful mountain views out the rear over the protected community land behind the property. The upstairs has two large vaulted rooms that share a jack and jill bathroom, as well as a sleeping loft. The walkout lower level has a 4th bedroom and full bath, large family room, game room area, laundry, and a walkout entry to the back yard. There is nice stone work outside, a large deck for entertaining, and covered front porch to enter the spacious mudroom out of the snow. This comes with the amazing Chimney Hill amenities including club house with indoor and outdoor pools, hot tub, gym, game room, theater, tot lot, basketball court, tennis courts, fishing ponds, winter ice skating, direct snowmobile trail access, winter snowmobile trailer parking, summer boat parking, and a la carte services such as trash pickup, plowing, etc. A must see!

If you have been looking for a multi-level home that is well-appointed, nicely furnished, move-in ready, on the Hill, with plenty of closets, this is IT! Smart thermostats and remote-controlled lighting. Ample mudroom foyer with vaulted ceiling and plenty of room for your gear, with slate flooring and custom paneling, laundry room and powder room or half bath. Bedroom with ridgeline views in stick season, a circular floor pattern from foyer with owner's closets/pantry, to fully equipped kitchen, dining with a wall of glass for views, living room with skylights, Mini split, a stone fireplace with pellet stove insert, and covered porch with a dry bar with more views. Second floor has a loft with futon sofa bed, primary bedroom with a bank of windows with views, full shared bath, and third bedroom. Each bedroom has 1-2 closets. The lower-level features two additional guest quarters, a family room with mini-split, pellet stove insert into stone fireplace, and a direct walkout mudroom entry. Enjoy the health and wellness lifestyle that Chimney Hill offers on its 1,200-acre campus adjoining the Gren Mountain National Forest! Close to skiing, shredding, golf, boating, hiking, biking, shopping, fine dining, and more with 300 acres owned in common by the HOA. ENJOY THE MEMBERS-ONLY EXCLUSIVE CLUBHOUSE LOCATED AT 2,000' IN ELEVATION.

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 the bright, open-concept great room featuring vaulted ceilings, skylights, oak floors, and a breathtaking fieldstone wood-burning fireplace crowned with a rustic wood mantel. It's an inviting centerpiece that creates the perfect cozy ambiance for relaxing on cold winter nights. The kitchen offers stainless appliances and a breakfast bar, flowing seamlessly into the dining and living areas. A large deck awaits for sunrise coffee or summer nights under the stars. The main level includes a serene primary suite, a bonus rm, and half bath. Upstairs features 2 large bedrooms, a full tiled bath with skylight, and a large loft. The finished lower level includes a separate entrance, garage access, family room w/ ping pong & darts, TV/Gaming room, laundry, and more. Extras include A/C in the great room, solid wood doors, garage space for snowmobiles, and an additional lot for parking or future garage. Walk to the clubhouse with pools, hot tub, fitness room, courts, skating rink, snowmobile/hiking trail access. Minutes from Harriman Reservoir, Mount Snow, and downtown Wilmington.