Properties Near 14 High Top Road Wilmington, VT

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Beautifully updated Country Club Village townhome overlooking the golf course! This move-in-ready property features a remodeled kitchen with granite countertops, stainless steel appliances, and an open-concept kitchen and dining area that's perfect for entertaining. All bathrooms have been tastefully renovated, and new flooring throughout gives the home a fresh, modern feel. Additional upgrades include a new furnace and hot water heater for added comfort and efficiency. The spacious loft provides flexible living space for guests, a home office, or a family room. Step outside to the back deck and enjoy peaceful golf course surroundings and seasonal winter views. Conveniently located near Mount Snow, The Hermitage Club, restaurants, shopping, and year-round recreational activities, this is an exceptional opportunity to enjoy Vermont living at its best.
Located in the desirable Chimney Hill community, this beautifully maintained 4 bedroom, 4 bath home offers the perfect combination of comfort, convenience, and year-round recreation. Designed for gathering and relaxing, the open-concept floor plan features vaulted ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas. A cozy gas fireplace creates a warm and inviting atmosphere after a day spent exploring Southern Vermont. The spacious kitchen opens to the main living area, making entertaining effortless, while expansive windows bring the outdoors in. Step outside to the large deck, ideal for summer barbecues, morning coffee, or simply enjoying the wooded surroundings. A direct-entry garage provides convenience in every season, and the finished lower level offers additional space for recreation, fitness, guests, or a media room. With four bedrooms and four baths, there is plenty of room for family and friends to gather comfortably. As a homeowner in Chimney Hill, you'll enjoy access to exceptional community amenities, including indoor and outdoor swimming pools, pickleball and tennis courts, a fitness center, clubhouse, skating rink, playground, and access to hiking and snowmobile trails. Ideally located just minutes from Mount Snow, The Hermitage Club, Lake Whitingham, and downtown Wilmington, this property places the very best of Southern Vermont recreation right at your doorstep. Whether you're seeking a full-time residence, weekend getaway, or investment property, 8 Deer Run Lane offers an outstanding opportunity to enjoy Vermont's four-season lifestyle in one of the area's most sought-after communities.
Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that feels inviting year-round. Step outside to the front porch and enjoy the seasonal mountain views while taking in the peaceful surroundings. Set on a wooded lot, the property offers a balance of privacy and convenience, with easy access to the extensive amenities of Chimney Hill and the recreation opportunities that make Southern Vermont such a sought-after destination. As a homeowner in Chimney Hill, you'll enjoy access to a wide range of community amenities, including an indoor pool, outdoor pool, fitness and community center, pickleball courts, ice skating, tennis courts, and an extensive network of hiking and recreational trails. Whether you're looking for outdoor adventure or a place to relax with family and friends, Chimney Hill offers activities for every season. Just minutes from Lake Whitingham, Mount Snow, The Hermitage Club, and downtown Wilmington, this home is ideally located for year-round enjoyment. Spend your summers boating, paddling, and swimming on the lake, and your winters skiing and snowboarding at nearby resorts. Whether you're looking for a primary residence, vacation home, or investment property, this four-bedroom getaway provides the space, location, and lifestyle that Vermont buyers are seeking.
Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, après ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more!
Beautiful three story Powderhorn townhome on the slopes of Haystack Mountain at the exclusive Hermitage Club Ski Resort — a true four-season retreat with thoughtful upgrades that set it apart from anything else in the development. Wake up to sunrise winter views over the mountains through expansive windows thanks to the end unit location. Enjoy woodsy scenery over your private deck and great natural light. The main living level features a vaulted great room area with wood-burning fireplace on stone hearth, a well-appointed kitchen with breakfast bar, dining area and guest half bath. Step out to the private deck and sip your coffee, or slip into the standout feature of this unit: a dedicated sunroom extension housing a private hot tub and shower, creating a spa-like retreat unlike anything typically found in a ski condo. Upstairs, the primary suite is a genuine sanctuary, positioned to capture the best light and views the home has to offer, with a large private bath and a sense of calm separation from the living spaces below. There is also a loft space ideal for office or reading nook. The lower level rounds out the unit with two bedrooms, a full bath, and a flexible bonus room ideal for a media area, home gym, bunk overflow, or additional storage — versatile space that gives this unit a footprint well beyond what most ski properties can offer. There is also a nice size mudroom with storage for all your gear, a great carport to keep your vehicle out of the elements, and great yard space for anyone looking for outdoor fun. At just three miles from Mount Snow and moments from the village of Wilmington and the surrounding lakes, this is a property that earns its keep in every season — with easy spaces to upgrade and make your own, and without the cost and complexity of newer on-mountain ownership. The siding and windows were just updated for tremendous new curb appeal.
Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and options for a garage. Nice, landscaped level lot with a shed and woodbin, firepit and plenty of parking. Enjoy all the amenities Chimney Hill offers including the exclusive members only clubhouse, located at 2,000' in elevation, it's the perfect spot to enjoy year-round featuring indoor and outdoor heated pools, a brand new hot tub, fitness room, arcade, playroom, lounge, fully-equipped kitchen, playground, community room, table tennis, pickleball, ice skating, hiking, biking and snowmobiling on the 1,200 acre resort campus nestled between the Green Mt National Forest and the town of Wilmington VT. Minutes from world class skiing and shredding at either Vail's Mt Snow or the private Hermitage Club. Discover Southern VT and enjoy outdoor and indoor music, festivals, unique shopping and dining, antiques, flea markets, golf, boating, paddleboarding, and so much more! Owner's list of features and improvements: Two Mini-Split Units for AC/Heat, Replaced all Electric Baseboard Heating Units, Gasoline powered generator hardwired into the electric panel, New Electric Panel, Hardwired Ring Outdoor Cameras, Vapor Barrier Throughout Crawl Space, Flooring throughout the whole house, Window treatments, Furniture, Bedding, Kitchen Appliances, HWH on GMP Rental Program $10 mo., Washer & Dryer, Four Flatscreen TV’s, Safe in MBR, Kitchen Countertops, Both Bathroom Fixtures, Countertops & Toilets, Ceiling Fans & Ceiling Lights, Safety Railings & Wiring on Stairs & Loft, Storage/Woodshed Outside, Firepit.
Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private lot in the Chimney Hill community on a quiet side road with easterly mountain views. Inside you will find a lovely open concept living space with vaulted ceilings and exposed woodwork, great natural light thanks to large windows, a spacious great room with wood burning fireplace, brick hearth, and exposed beams, kitchen with island and spacious dining area, wood flooring, a main floor bedroom and full bath, upstairs bedroom with sleeping loft, a full walkout lower level family room partially finished with bunk room and third almost finished bath and laundry, lower level foyer, and hot tub area, ample storage, and more. 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. Septic sized for 3 bedrooms full time use.
Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large windows, natural woodwork throughout, a kitchen with stainless appliances and breakfast bar, a spacious dining area open to the living room with gas fireplace and brick hearth, a main floor bedroom and full bath as well as a large mudroom for all your gear, 2 upstairs bedrooms including a large bunk room with great closet space, as well as a second full bath recently renovated, a finished walkout lower level with games, additional sleeping space, and ample room to spread out. There is also a large storage and utility room for seasonal storage or owner lock out space. There is a garage shed outside for snowmobile, a fire pit, and large entertaining deck. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management.
Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas stove, spacious dining area, and guest bath. There is large primary bedroom and bath on the main floor with it's own private deck. The lower level is another primary suite with a walkout access, as well as a large finishable rear room that could be ideal for media area, exercise room, or more, easily finishable. The space is a welcome surprise compared to typical ski condos and would be efficient and cost effective for a Hermitage member compared to other on site pricing. At just a 3 mile drive to the Mount Snow ski resort and even nearer the village of Wilmington and Lakes, this is a true four season getaway. Coldbrook water and sewer is $1500/year.
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 enjoyment. Inside features include a large open living space with vaulted ceiling, wood burning stove, large open kitchen and dining area, main floor primary suite, main floor guest bedroom and full tiled bath, den/tv loft, and second floor bunk room with half bath. There are large windows open to the winter mountain view. There is a 1000 sqft lower level with full size windows, ideal for adding additional usable space. A very functional layout with all the charm befitting a Vermont getaway. This comes with all the unique Chimney Hill amenities including club house, indoor and outdoor pools, hot tub, gym, game room, theater, tennis courts, basketball court, tot lot, fishing pond, winter ice skating, and a la carte management services such as snow removal and trash pickup.
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.
Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or residential space. The exterior features parking for three cars, as well as public parking across the street, a lovely front porch, and side patio with perennial gardens. The main floor has a large open concept space presently with table seating, but which could easily be converted for other needs. There is a half bath off the enclosed mudroom entry, new lighting throughout, a vestibule, main floor counter area with bar seating, espresso machine, wine cooler and ice maker, walk in pantry and ample additional storage, full kitchen with commercial Wolf stove, dish washing and prep areas, office, and insulated cold pantry with separate side entry. There is access to a full updated bath which has a second door into the apartment stair hall and mudroom, also with its own mudroom entry with cubbies and storage. The stairs lead up to a large open concept loft apartment, spacious kitchen with wolf stove and Subzero fridge, a bench dining area, wood burning fireplace, dual built in bedroom nooks, sleeping loft, full laundry, full bath, wood floors, and great natural light. Less obvious upgrades include a standing seam metal roof, Buderus heating system, paid water for 18 dining seats, updated windows, electrical, insulation, and more. The possibilities are endless as it could easily be a gallery, boutique, coffee shop, bakery, or simply residential space for your home away from home. Also listed under commercial MLS# 5075131.
Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More thoughtful touches include a dedicated propane grill, so you don't have to fuss with tank replacements, custom woodwork and built-in closets, vaulted bedroom ceilings with dramatic woodwork, double lot for added privacy, shed, and an outdoor shower! A metal roof, new furnace, new flooring, wood stove and flue, new appliances, shed, wood storage, and includes most furnishings are included. Enjoy all the amenities Chimney Hill offers on its 1,200-Acre Campus, with 550-Acres owned in common by the members. Amenities feature the exclusive Clubhouse with indoor and outdoor heated pools, a hot tub, fitness center, arcade, small toddler playroom, après ski lounge, community room, fully equipped kitchen, outdoor BBQ area, playground, pickleball, tennis, basketball, seasonal ice skating, multi-trail system, snow shoeing, cross country skiing, hiking and biking. Plus, Southern Vermont offers nearby opportunities for canoe, kayak, sailing, pontoon, and other boating, paddle boarding, golf, fishing, shopping, world-class skiing and shredding, fine dining, flea markets, unique shopping experiences, music, festivals, and so much more!
On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities Chimney Hill Resort offers including the Clubhouse located at 2,000' in elevation featuring year-round swimming in the indoor/outdoor heated pools, hot tub, fitness, arcade, playroom, playground, patio, community room, tennis, pickleball, ice skating, 550 acres of land owned in common by the HOA, all on our beautiful 1,200-acre campus adjoining the Gren Mt National Forest. Plus there is so much more to the Deerfield Valley of Southern VT including fine dining, unique shopping, festivals, music, arts and crafts, breweries, distilleries, artisan and craft tours, hiking, biking, boating, golfing, flea markets, antiques, paddleboarding, kayaking, jet and water skiing, world class alpine skiing and shredding, and so much more!
An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above the garage provides extra versatility—whether for guests, family, or potential rental income. Located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Sellers is highly motivated and welcomes all reasonable offers. Property being sold AS IS.
Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in the stone hearth, gorgeous adirondack furnishings and fixtures, updated appliances throughout, a large dining area, mudroom, master suite with bright upgraded bath, additional guest suite, 2 guest rooms with a shared bath, and plenty of space to stretch your legs all 4 seasons. There is a large back deck for outdoor entertainment, covered front porch to escape the weather, and amenities including 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. 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!
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.
This wonderful home boast 10.5 +/- acres, plenty of room for gardening, a pond and is only moments to the village center! Beautiful hard wood floors throughout, Livingroom with gas fireplace a a beautiful view, dining area and kitchen, 3 bedrooms, 2 bathrooms, 2 decks and a simple 1 car garage. The lower level boasts a walk- out, that is waiting to be finished!
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!!!

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