$349,000 $204 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1712  |  Acres: 0.59
Wednesday Aug 26, 2026
Description: 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. Featuring the tremendous Chimney Hill amenities including 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. See MLS Property & Listing Details & 19 images.

$354,900 $283 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1586  |  Acres: 0.75
Sunday Aug 2, 2026
Description: Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas. Step inside through the spacious mudroom, the perfect place to kick off your boots after a day on the slopes or hiking the trails. The warm and inviting interior features comfortable living spaces, a finished basement that provides extra room for guests, a game room, home office, or cozy movie nights, and a layout designed for making memories. Outside, the deck is freshly remodeled, creating an even better space to relax and take in the beautiful wooded views. Enjoy your morning coffee surrounded by nature, unwind after a day of adventure, or entertain friends in your own private mountain retreat. One of this property's unique advantages is the additional lot located directly across the street, offering exciting possibilities for future owners. Whether you envision building a garage, creating additional parking, or simply holding the land for future use, it's a valuable bonus that adds flexibility and long-term potential. Located just minutes from Mount Snow and a short distance to other nearby ski areas, this home puts four-season recreation right at your fingertips. Spend your winters skiing and snowboarding, then enjoy mountain biking, hiking, golf, lakes, breweries, restaurants, and charming downtown Wilmington throughout the warmer months. No matter the season, adventure is always close by. Speaking of close by, the Clubhouse with indoor and outdoor pools, hot tub, game room, tennis courts, gym, etc is only a short walk away! If you've been dreaming of a Vermont getaway with room to grow, beautiful surroundings, and an unbeatable location, 21 Big Bend Loop is ready to welcome you home. See MLS Property & Listing Details & 59 images.

$399,000 $290 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $19,000 down 5% on July 8th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1378  |  Acres: 0.5
Thursday May 21, 2026
Description: Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home boasts updated flooring throughout the main living areas and two bedrooms, with additional flooring material included to complete the job. The flat yard offers a perfect hangout space with a firepit and seating area, ideal for outdoor gatherings. Residents enjoy access to the community's recreation center, featuring a summer outdoor pool, indoor pool, and more. This fantastic location is just minutes from the Hermitage Ski Club, Mount Snow Resort, two golf courses, and the scenic Harriman Reservoir and Lake Raponda for boating and swimming. Wilmington's vibrant Main Street and other attractions are also nearby, making this home a perfect blend of comfort and convenience. This home is not only an ideal personal retreat but also a proven rental investment. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$399,000 $363 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $60,000 down 15% on August 5th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1100  |  Acres: 0.44
Friday Jun 19, 2026
Description: Tucked among mature trees in the desirable lower section of Chimney Hill, this charming home offers comfort, character, and easy living. A gently sloping gravel driveway and attached converted garage provide year-round convenience, while beautifully established perennial gardens and a gently sloping yard create an inviting outdoor setting rarely found in the area. Inside, the home exudes warmth and rustic Vermont charm with a rustic, relaxed atmosphere that immediately feels like home. The thoughtfully designed floor plan provides comfortable ground-floor living, with the primary living spaces and bedrooms conveniently located on the main level. A spacious deck and covered side porch provide the perfect places to enjoy morning coffee, unwind after a day outdoors, or entertain friends and family. Ideally situated less than 2 miles from downtown Wilmington, approximately 7 miles from Mount Snow, less than 1 mile from Harriman Reservoir, and about 5 miles from Lake Raponda, the property offers easy access to some of Southern Vermont's most sought-after recreation. Enjoy nearby swimming, boating, paddling, hiking, mountain biking, skiing, and golf. Chimney Hill residents enjoy access to extensive community amenities, and nearby VAST trail access offers additional winter recreation opportunities. Whether you're looking for a primary residence, weekend retreat, or mountain getaway, this charming home offers a peaceful setting, practical features, and timeless appeal in one of Southern Vermont's premier four-season destinations. See MLS Property & Listing Details & 45 images. Includes a Virtual Tour

$399,000 $385 per sq.ft. Wilmington VT Home »

Waterfront on Pond _Unnamed
2 Beds | 1 Baths |   Total Sq. Ft. 1036  |  Acres: 3.4
Friday Jul 3, 2026
Description: Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or expanded living space. The walkout basement features high ceilings and excellent potential for future finishing, while also offering convenient storage for tools, outdoor gear, and recreational toys. Outside, mature gardens add color and character throughout the seasons, while a quaint sugarhouse adds a touch of classic Vermont charm and offers endless possibilities as a hobby space, garden shed, or rustic retreat. Although close to Wilmington's shops, restaurants, and year-round activities, the property offers a wonderful sense of privacy. Just a short drive to Mount Snow, The Hermitage Club, hiking trails, lakes, golf, and the many attractions that make southern Vermont such a sought-after destination, this home is ideal as a full-time residence, a perfect starter home, or a charming country retreat with room to grow and make it your own. Private road no drive-bys. See MLS Property & Listing Details & 24 images.

$420,000 $155 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $169,000 down 40% on August 14th 2026
7 Beds | 5 Baths |   Total Sq. Ft. 3518  |  Acres: 3.08
Saturday Mar 22, 2025
Description: 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. See MLS Property & Listing Details & 29 images.

$425,000 $281 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1510  |  Acres: 0.57
Wednesday May 13, 2026
Description: Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and large windows, natural woodwork throughout, a brand new kitchen with stainless appliances and quartz counters, a spacious dining area open to the living room with gas fireplace and stone hearth, a main floor bedroom and updated full bath, 2 upstairs bedrooms including a spacious primary and a second full bath, and a main floor mudroom and laundry area great for all your seasonal gear. There is also a large owners closet or bonus room off the main bath that could serve as an office with patio door out to the deck. Less obvious upgrades include direct vent heating, all new flooring, and convenient wood shed and bear proof trash bin. 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. See MLS Property & Listing Details & 28 images.

$425,000 $351 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2345  |  Acres: 2
Thursday May 21, 2026
Description: Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for gatherings or quiet evenings, while the functional kitchen and dining room combination provides a practical space for meals and entertaining. From the dining room sliding door, access the deck, perfect for al fresco dining or soaking up the sun while overlooking the expansive backyard. Behind Door Number 1, off the living room, discover two comfortable bedrooms and a full bath. Behind Door Number 2, a stairway leads to a full, finished basement, where a versatile recreation room can be customized to suit your needs, whether it be a home theater, game room, or additional living space. The basement also includes the fourth bedroom, a ¾ bath, a practical utility room, and a storage area, with the ease of a walk-out to the backyard from this level. Behind Door Number 3, adjacent to the kitchen/dining area, lies the primary bedroom with a full ensuite bathroom, offering a peaceful retreat for rest and relaxation. This home is not only perfect as a primary residence with easy access to schools, a thriving Main Street, and area activities, but also holds potential as a second home or investment property, just minutes to ski resorts, golf courses, and Harriman Reservoir for swimming and boating. Located within the Beaver Brook Association, residents benefit from comprehensive road maintenance, snow plowing, and sanding services. Don't miss the opportunity to make this beloved home your own, enjoying the serene setting and convenient amenities it has to offer. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$439,000 $311 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $90,000 down 21% on July 3rd 2026
Waterfront on Pond _Unnamed
3 Beds | 2 Baths |   Total Sq. Ft. 1410  |  Acres: 10.5
Monday Dec 8, 2025
Description: 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! See MLS Property & Listing Details & 15 images.

$439,990 $263 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $134,910 down 31% on August 18th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1850  |  Acres: 1.18
Thursday Nov 13, 2025
Description: 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. See MLS Property & Listing Details & 42 images.

$449,000 $374 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 2 Baths |   Total Sq. Ft. 1200  |  Acres: 1.15
Tuesday Aug 25, 2026
Description: Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready! Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse located at 2,000' on the Hill, featuring year-round swimming, new hot tub, fitness room, arcade room, playroom, community room, fully equipped members kitchen, reading nook, après ski lounge, 3 tennis court areas plus basketball court, extensive multi-use trail system, snowmobiling, ice skating, pickleball and tennis, stocked fishing pond, hiking, biking, and more! Plus, the Deerfield Valley offers world class skiing and shredding literally minutes away, fine and casual dining, unique shopping, escape room, mini, disk, and traditional golf, kayaking, canoeing, pontoon and sail boating, paddleboarding, the Green Mt National forest, antiques, flea markets, breweries, wineries, distilleries, music, theater, equestrian events, and so much more! See MLS Property & Listing Details & 47 images.

$455,000 $294 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 2 Baths |   Total Sq. Ft. 1550  |  Acres: 0.95
Monday Jun 1, 2026
Description: 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! See MLS Property & Listing Details & 60 images.

$459,000 $297 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $40,000 down 9% on August 24th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 1548  |  Acres: 1
Tuesday Jan 6, 2026
Description: 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. See MLS Property & Listing Details & 23 images.

$459,000 $221 per sq.ft. Wilmington VT Home »

1 Beds | 3 Baths |   Total Sq. Ft. 2076  |  Acres: 0.06
Wednesday Jan 28, 2026
Description: 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. See MLS Property & Listing Details & 33 images.

$460,000 $240 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 7.1
Wednesday Jun 24, 2026
Description: 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. See MLS Property & Listing Details & 34 images.