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36 Ives Rd, Wilmington
$399,000
3 Beds ⋅ 2 Baths ⋅ 5113520 MLS
Welcome to 36 Ives Road, a classic Vermont A-frame set in a quiet wooded setting just minutes from Mount Snow and a short drive from downtown Wilmington. Inside, warm natural woodwork, soaring cathedral ceilings, skylights, and abundant natural light give the home the inviting character you want in a Vermont retreat. The open kitchen, dining, and living areas create an easy gathering space, while the wood stove adds warmth and atmosphere after a day on the mountain. A loft overlooks the main living area and provides flexible space for additional sleeping, a home office, reading nook, or second lounge. Step outside to enjoy the balcony, fire pit, and peaceful surroundings, with plenty of space to slow down and enjoy the seasons. The home is being offered fully furnished, making it easy to settle in and start enjoying it right away. The location is what really ties it all together. Mount Snow is just minutes away, while downtown Wilmington offers restaurants, shops, galleries, and the charm of a historic Vermont village. In the warmer months, enjoy swimming, boating, and kayaking at Harriman Reservoir, along with miles of hiking and biking throughout the Deerfield Valley. Whether you're looking for a ski getaway, a four-season escape, or a Vermont home base to enjoy year-round, 36 Ives Road offers a relaxed setting in the heart of one of Southern Vermont’s most popular recreation areas.

36 Ives Rd, Wilmington
3 Lightning Ledge Way, Wilmington
$289,900
5 Beds ⋅ 3 Baths ⋅ 5113467 MLS
CASH OR REHAB LOAN ONLY – PROPERTY NEEDS WORK! Ski lodge within walking distance to the Chimney Hill Clubhouse, offering 5 bedrooms, 2½ baths, and plenty of space to create your ideal Vermont getaway. Three levels include a family room with wood stove, laundry, mudroom, kitchen with island, dining area with cathedral ceiling, sunken living room with fireplace, and sliders to a multi-level deck. Natural light and woodwork add to the mountain-lodge character. Enjoy Chimney Hill’s extensive four-season amenities, including indoor/outdoor swimming, tennis, pickleball, hot tub, fitness room, skating, hiking, biking, snowmobiling, playground, clubhouse, and more. Conveniently located minutes from skiing, dining, shopping, breweries, festivals, and the Green Mountain National Forest. Property is being sold AS-IS and requires renovation. Cash sale or rehab financing required. Bring your vision and make this mountain retreat your own! This property is eligible under the First Look Initiative which expires after 30 full days on market. No investor offers until first look period expires. No offers regardless of buyer type will be negotiated within the first 7 days of listing.

3 Lightning Ledge Way, Wilmington
180 Parsons Rd, Wilmington
$375,000
3 Beds ⋅ 1 Baths ⋅ 5113271 MLS
Come see this sweet, well-kept 3-bedroom ranch. The heart of the home is its inviting open concept living area, featuring a handsome stone fireplace with a pellet stove insert for easy fires in the winter. The fully updated kitchen has abundant Kraftmaid cabinets, an island with seating, quartz counters, and Energy Star appliances. Enjoy meals and company in the warm weather on the wrap-around deck, easily accessible from both the kitchen and living area. A hallway, a few steps up from the kitchen, leads to the three bedrooms; the primary bedroom is large enough for a king-size bed. The spacious, updated ¾ bath has a contemporary vanity and tasteful tile flooring and shower finishes. Added bonuses include a two-car garage, a shed for storage or a workspace and extra space to finish in both the attic and basement. Accented with attractive ledge outcroppings, the land - ideal for recreation and gardening- has a blend of both level and sloping areas as well as a mix of sun and shade. Caring for the home will be easier thanks to the home’s vinyl siding, newer windows, standing seam metal roof and vinyl plank flooring throughout the interior. The ideal location offers the best of both worlds: a tranquil rural retreat set on a quiet road, but only minutes to downtown Wilmington, 20-minutes to the Mt. Snow resort and close to year-round recreation on Lakes Harriman, Raponda, Sadawga, snowmobile and hiking trails and much more. All furnishings available for an additional fee. Showings start on October 11. Open House Sunday, October 11 11am-1pm, Monday October 12 10am-12pm

180 Parsons Rd, Wilmington
90 Big Bend Loop, Wilmington
$599,000
4 Beds ⋅ 3 Baths ⋅ 5113132 MLS
Stunning updated and expanded chalet just a short drive out of the village of Wilmington. This home sits privately on a wooded double lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home was extensively renovated and expanded and now has tremendous unique one of a kind space featuring a gorgeous vaulted living room with exposed natural woodwork, great natural light from the large windows, a wood burning fireplace and brick hearth, upscale wood flooring throughout, a beautiful kitchen with quartz counters, stainless appliances, breakfast bar, farm sink, and tile backsplash, large dining area, wet bar and entertaining area, main floor bedroom and full bath, and large mudroom for all your gear. The bedroom level features three spacious bedrooms with two more upscale baths, including tiled showers and a gorgeous pedestal tub, as well as access to the outside. Additionally there is an overflow sleeping loft, huge upper and lower decks for outdoor enjoyment and BBQs, and ample lawn space for enjoyment no matter the season. 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.

90 Big Bend Loop, Wilmington
529 Coldbrook Rd, Wilmington
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 5112992 MLS
Perfectly positioned just across from the entrance to The Hermitage Club, this beautifully appointed mountain home offers the ideal balance of comfort, convenience, and Vermont charm. Whether you're heading to the slopes, enjoying a round at Haystack Golf, exploring nearby snowmobile trails, or spending the day at Lake Whitingham, this location places you in the heart of everything the Deerfield Valley has to offer. Inside, warm natural wood finishes, reclaimed barn board accents, soaring cathedral ceilings, and a dramatic wall of windows create a welcoming mountain retreat filled with natural light. The open-concept living area is anchored by a beautiful stone fireplace, offering the perfect gathering space after a day outdoors. The spacious kitchen features granite countertops, stainless steel appliances, custom cabinetry, and a generous center island that flows seamlessly into the dining and living areas, making entertaining effortless. The home offers three comfortable bedrooms plus a bonus room for additional guests or flexible living space, along with three beautifully updated bathrooms. The primary suite provides a peaceful retreat with a spa-inspired bath featuring a tiled walk-in shower, soaking tub, and quality finishes throughout. The finished lower level expands the living space with a large recreation room, perfect for movie nights, game days, or relaxing with family and friends. A two car garage offers ample room for vehicles and all of your Vermont gear. Outside, the expansive deck invites you to unwind in the private hot tub, dine outdoors, or simply enjoy the peaceful woodland setting. Whether you're looking for a full-time residence, a weekend getaway, or a four-season vacation home, 529 Coldbrook Road delivers exceptional craftsmanship, inviting living spaces, and one of the area's most desirable locations just moments from The Hermitage Club and a short drive to Mount Snow, downtown Wilmington.

529 Coldbrook Rd, Wilmington
14 High Top Rd Unit B124, Wilmington
$499,900
3 Beds ⋅ 3 Baths ⋅ 5112846 MLS
Enjoy Vermont living in every season! This spacious 3-bedroom, 3-bath home sits on an oversized lot close to the Hermitage Club and Mount Snow, offering plenty of room to gather, relax, and unwind. Outstanding community amenities include indoor and outdoor pools, a hot tub, tennis, pickleball, and basketball courts, plus a clubhouse with an arcade and lounge. With hiking, biking, boating, golf, and skiing at your fingertips, adventure is always within easy reach. Whether you’re seeking a mountain getaway or a year-round home, this property offers space, recreation, and a convenient location to enjoy it all. The seller is open to selling the neighboring lot to the purchaser of the home. The offer is at a very fair price, and the seller is open to negotiations.

14 High Top Rd Unit B124, Wilmington
60 E Brook Xing Unit C-201, Wilmington
$359,000
3 Beds ⋅ 2 Baths ⋅ 5112782 MLS
This gem is tucked away in the quiet Section C part of the super popular Chimney Hill, HOA this modified ranch style home, featuring 3 bedrooms, half and full baths, a gas fired stove in the open concept living/dining area, and a pellet stove in the Bonus Room. Careful attention to detail, landscaped gardens, Firepit, fenced in area in the back, garage/Bonus Room addition, covered porch, custom woodwork inside and out. For those who like a more rustic 'Vermonty" vibe, this is it! Stop dreaming and start living the dream! Enjoy all the amenities offered by Chimney Hill ON THE 1,200 Acre Campus with an exclusive member only Clubhouse located 2,000' up on the Hill with indoor and outdoor heated pools for year-round swimming, arcade room, après ski lounge, fully-equipped kitchen for members use, fitness room, community style hot tub, community room, playgrounds, 3 areas with tennis courts, extensive trail system, lookout, fishing pond stocked with annual kids fishing derby, seasonal pickleball and ice skating, basketball court, birchwood recreation area, and so much more! See why Southern Vermont and the Deerfield Valley are so popular, offering World Class Skiing and Shredding at Vail's Mt. Snow, and the privately owned Hermitage Club at Haystack Mt., festivals, flea markets, antiques, uniques shopping and fine dining experiences, music, mountains, boating, golf, S VT Pickleball Club, mountain biking, and so much more!

60 E Brook Xing Unit C-201, Wilmington
481 Vt Rte 9 W, Wilmington
$299,000
4 Beds ⋅ 1 Baths ⋅ 5112278 MLS
OPEN HOUSE Saturday- October 10th 11AM-1PM. LOCATION! This 4-bedroom, 1-bath home is located directly across from beautiful Harriman Reservoir and just outside the Village of Wilmington. A great opportunity to bring your vision in an unbeatable location. This home offers plenty of space and character, along with important updates including a new foundation installed in 1993 and new French drains recently installed for added peace of mind. Enjoy the convenience of being just outside downtown Wilmington, with its charming shops, restaurants, and local amenities, while having Harriman Reservoir right across the road for boating, swimming, fishing, and summer fun.Mount Snow is just a short drive away, offering skiing and year-round mountain recreation. Whether you’re looking for a full-time home, vacation getaway, or a place to enjoy all that the Deerfield Valley has to offer, this property is worth a look. Property is being SOLD AS IS

481 Vt Rte 9 W, Wilmington
511 Shearer Hill Rd, Wilmington
$900,000
5 Beds ⋅ 3 Baths ⋅ 5112234 MLS
A rare opportunity to own 95+ acres in the heart of Southern Vermont with a beautiful post and beam homestead and easy access to the country village of Wilmington and Mount Snow ski resort. This property sits easily accessible off a town road just outside the town of Wilmington. The acreage is mainly in Wilmington but crosses the Whitingham border, and affords a pastoral setting with long range mountain views, gorgeous exposure, and the ultimate in privacy thanks to a long drive. The home has been lovingly maintained and expanded by the current owners and features a large living room area with expansive windows, gorgeous natural woodwork throughout thanks to the post and beam construction, kitchen with breakfast bar and stainless appliances, wood burning stove, a large deck for entertaining, main floor den and full bath, three upstairs guest bedrooms and a second full bath. There is a large mudroom entry area that connects this space to the addition, which includes a second large family room area, second kitchen, two more guest bedrooms and a full bath, as well as a full attached garage. This is a true gem nestled in the hills and affords tremendous usability, rentability, privacy, and Vermont serenity, in a neatly wrapped package.

511 Shearer Hill Rd, Wilmington
52 North Rd, Wilmington
$325,000
4 Beds ⋅ 2 Baths ⋅ 5111868 MLS
Located on a corner lot in the lower section of Chimney Hill, this 4-bedroom, 2-bath home offers 1,856 square feet of living space and a great opportunity for buyers looking to refresh, personalize, and add value. Set on 0.69 acres, the property provides a comfortable amount of outdoor space without the burden of extensive maintenance. The two-story layout is well-suited for full-time living or use as a second home. The first floor features wood floors throughout the main living areas, a spacious living room with a wood-burning fireplace, an additional lounge, first-floor bedroom and bath. The large eat in kitchen is a stand out with high ceilings, granite countertops, a farmhouse sink, double oven, and a Wolf range hood. The second floor includes a generous primary bedroom with French doors opening to a private balcony, a full bathroom, and two additional bedrooms, including a spacious bunk room with built-ins. Conveniently located less than 2 miles from historic downtown Wilmington, Vermont shops, dining, and entertainment, 5 miles from the exclusive Hermitage Club at Haystack Mountain and 7 miles from Mount Snow. The clubhouse features indoor and outdoor pools, a hot tub, fitness area, game room, arcade, movie theater, and recreational space for owners. Outdoor amenities include lighted tennis and basketball courts, an outdoor skating rink with warming hut, a stocked fishing pond, hiking trails, playgrounds, picnic areas, and direct access to the VAST snowmobile trail system. The property is offered as is. Water is turned off. Appointment required.

52 North Rd, Wilmington
272 Shearer Hill Rd, Wilmington
$419,000
3 Beds ⋅ 3 Baths ⋅ 5111420 MLS
Set on 5.5 picturesque acres in a terrific location just minutes from downtown Wilmington, this three-bedroom plus den, three-bath chalet offers plenty of space and potential to create your ideal vacation retreat or primary residence in the Deerfield Valley. The main level features an open kitchen and dining area, a comfortable living room with a beautiful fieldstone fireplace, and sliders leading to a deck where you can enjoy the surrounding setting. A primary bedroom with a full bath completes this level. Upstairs, you’ll find two additional bedrooms and a ¾ bath. Newly refinished lower level offers even more possibilities: a family room with another fieldstone fireplace, sheetrocked walls, new flooring, an office or den, and a full bath. The home also includes an attached one-car garage (13x19) with washer and dryer hookups. With some TLC and your personal vision, this spacious chalet could become the perfect getaway, offering privacy, acreage, and convenient access to all that the Deerfield Valley has to offer.

272 Shearer Hill Rd, Wilmington
152 Lake Raponda Rd, Wilmington
$1,997,000
5 Beds ⋅ 4 Baths ⋅ 5110842 MLS
Enjoy four season living from this spacious lake home just off Lake Raponda in Wilmington Vermont. The 4+ bedroom home has 12+ acres with direct lake frontage, privacy thanks to the 12+ acres, and a tremendous updated size ideal for entertaining. The property consists of 3 buildable parcels, just a short drive from the Mount Snow Ski Resort, each with tremendous privacy and natural beauty. A stream which feeds the lake runs down along the lower boundary and the owners have established paths to walk and cross country ski. Generous clearing has allowed for the majority of the home to have direct views of the lake, and provides for easy access to the water for kayaking, paddleboarding, or a private shallow dock perfect for protection from lake traffic and wildlife. The interior of the home has been completely renovated and features high ceilings, open concept living areas, a spacious kitchen with stainless appliances, new counters and cabinets, a large breakfast bar, a living room with wood burning fireplace, a main floor bedroom and bath for guests, dual primary second flood suites, dual spacious guest rooms with large closets and windows, a full length finished attic for overflow sleeping or play room, a full finished lower level with media room, wet bar with live edge wood features, and sauna, and oversized 2 car garage. Less obvious upgrades include new windows and doors throughout, approved septic plans for the additional two parcels, and extensive cosmetics. For anyone hoping to entertain in all seasons and bring up all the guests, this spacious upscale home has it all. Finish work currently being done. Photos show finished rendering and digital staging in addition to current photos.

152 Lake Raponda Rd, Wilmington
48 High Top Rd Unit B130, Wilmington
$695,000
3 Beds ⋅ 2 Baths ⋅ 5109817 MLS
This is IT! Section B double Lot at the end of the Road! Renovated inside and out. expanded chalet style home features 3 bedrooms and two baths, a primary suite with a private covered porch with dedicated gas firepit and a bonus room awaiting your vision, landscaped grounds, woodstove-heated attached double garage with automatic doors, front deck with pergola, 2 year-old maintenance-free exterior with solar lighting and a dedicated gas line for the grill on the rear deck, custom stonework, skylights with sensors for rain that close automatically, kitchen redone 7 years ago with custom woodwork and granite countertops, roof is 4 years old, Renai tankless hot water heater, hardwood flooring installed 6 years ago, propane fireplace in the living room addition and a wood stove by the kitchen sitting area, electric baseboard, makes 3 heat sources, and includes some furnishings. Enjoy all the amenities the Chimney Hill Resort offers including year-round swimming, indoor and seasonal outdoor heated pools, new community sized hot tub, arcade, fitness room, playroom, lounge, kitchen, community room, grills, and playground at the members-only clubhouse, plus tennis, seasonal ice skating and pickleball, basketball, extensive trails, fishing pond and more!

48 High Top Rd Unit B130, Wilmington
9 Greer Ct, Wilmington
$575,000
3 Beds ⋅ 3 Baths ⋅ 5109551 MLS
Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great natural light as well as complimentary up lighting, a highly efficient pellet burning stove, an open concept living area with spacious dining area and upscale kitchen with granite counters, stainless appliances, and kitchen island, a large main floor primary bedroom suite with soaking tub, an additional guest bedroom and full guest bath on the main floor, large loft den with sofa and tv, overlooking the great room, as well as second primary suite with full bath. Additionally, there is a huge unfinished walkout basement that would afford tremendous expansion potential where you could add additional living and overflow sleeping space. This is complimented by the amazing Chimney Hill amenities including club house with indoor and outdoor pools, hot tub, gym, locker rooms, game room, theater, playground, basketball and tennis courts, winter ice skating, and on site management company offering additional a la carte services for downtime, not upkeep.

9 Greer Ct, 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
99 Mirror Lake Xing, Wilmington
$3,999,000
5 Beds ⋅ 8 Baths ⋅ 5108480 MLS
Old Mill on Haystack Mountain is a mountain residence designed for the next chapter of family life, set on 3.58 acres within the gates of The Hermitage Club with views of the Haystack trails. With over 6,000 square feet of finished living space, the home offers the scale and flexibility to comfortably accommodate children, grandchildren, friends, and extended family while still providing a sense of privacy. The five-bedroom layout includes both a first-floor primary suite and a second-floor primary suite, along with generous gathering spaces and a finished lower level designed for recreation, entertaining, and guests. At the heart of the home is a dramatic two-story great room with soaring ceilings, wood tongue-and-groove detailing, and a wood-burning fireplace. Ten-inch wide-plank white oak flooring carries through the main living areas, complementing the custom chef’s kitchen with high-end cabinetry, a 48-inch Wolf range, and a 48-inch Sub-Zero refrigerator. Substantial windows bring in natural light and frame the mountain setting, while the lower level continues the home’s impressive scale with 10-foot ceilings, a gas fireplace, and additional space to gather and unwind. Radiant heat, a heat-pump system, and air conditioning provide year-round comfort, and upscale finishes throughout reinforce the home’s refined modern mountain aesthetic. For families who already understand the appeal of Haystack and The Hermitage Club lifestyle, Old Mill offers something increasingly difficult to find: substantial new construction without the years typically required to secure land, design, permit, and build from the ground up. The home is scheduled to be ready for Winter 2027, with an early purchaser having the opportunity to personalize selected finishes. Thoughtfully designed for the way families gather in Vermont today, Old Mill on Haystack Mountain offers the space, comfort, and setting to enjoy the mountain for years to come.

99 Mirror Lake Xing, Wilmington
113 Happy Haven Rd, Wilmington
$419,000
5 Beds ⋅ 3 Baths ⋅ 5108469 MLS
Classic 5-bedroom, 3-bath Wilmington, Vermont chalet offering three levels of living space, outdoor hot tub, stone firepit, multiple wood-burning fireplaces, and bonus space! Tucked away on a nice lot near the end of the road but still convenient to Mount Snow, Route 100, and downtown Wilmington. The main level is the heart of the home, with soaring cathedral ceilings, an open kitchen, dining and living area, a floor-to-ceiling brick wood-burning fireplace and a wall of windows that brings the outdoors in. In winter, picture watching the snow fall through the glass with the warmth and crackle of the fire behind you. Two bedrooms and an updated full bath are also located on this level. The lower level offers plenty of additional space with a second kitchen/wet bar, two bedrooms, a full bath and another living area with its own wood-burning fireplace, creating a great setup for guests or simply giving everyone room to spread out. This is excellent rec space, a game room and wet bar, or a private 2-bedroom suite for your guests or another group to enjoy. The third floor is lofted above the main living area with exposed brick from the fireplace below and features a spacious primary bedroom suite with a nicely renovated private bath. Outside, enjoy a generous deck, hot tub and stone fire pit and seating area in a peaceful setting near the end of a town-maintained road with limited through traffic. From here, you are well positioned to enjoy everything that makes Southern Vermont such a special place to spend time: skiing and snowmobiling in winter, lakes and golf in the warmer months, miles of hiking and National Forest trails, plus the shops, restaurants and vibrant small-town communities of Wilmington and the surrounding Deerfield Valley. With multiple ski areas and an incredible range of outdoor recreation close by, this is a true home base for the Vermont vacation lifestyle in every season.

113 Happy Haven Rd, 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
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
47 Upper Howes Rd Unit A-23, Wilmington
$449,000
3 Beds ⋅ 2 Baths ⋅ 5106545 MLS
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!

47 Upper Howes Rd Unit A-23, Wilmington
47 West Rd, Wilmington
$997,000
3 Beds ⋅ 4 Baths ⋅ 5105900 MLS
Be among the first to enjoy this brand-new mountain modern home in the sought-after Chimney Hill community. Thoughtfully designed for both year-round living and weekend getaways, this 3-bedroom, 4-bath home offers a bright, open floor plan filled with natural light and clean, contemporary finishes. The main living area creates an inviting space for gathering, with an open kitchen, dining, and living room designed for today's lifestyle. Upstairs, you'll find a spacious primary suite along with two comfortable guest bedrooms, offering privacy and comfort for family and friends. The fully finished lower level significantly expands the home's living space with multiple bonus rooms and a generous recreation area, providing endless possibilities for a home office, fitness room, media room, bunk room, hobby space, or additional guest accommodations. Located in Chimney Hill, owners enjoy access to outstanding community amenities including indoor and outdoor swimming pools, hot tub, fitness center, tennis and pickleball courts, skating rink, community center, hiking and snowmobile trails, and year-round recreational activities. Just minutes from Mount Snow, The Hermitage Club, Lake Whitingham, and downtown Wilmington, this exceptional new construction home offers the perfect combination of modern design, low-maintenance living, and Vermont mountain lifestyle. Photos have been virtually staged.

47 West Rd, Wilmington
21 Lawrence Davis Dr, Wilmington
$299,000
3 Beds ⋅ 2 Baths ⋅ 5105074 MLS
NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy, convenience, and value in this immaculate 3-bedroom, 2-bath double-wide manufactured home offering approximately 1,300 square feet of comfortable one-level living. Set on 1.4+/- acres on a quiet dead-end road, this property offers a peaceful setting while remaining just a short drive to downtown Wilmington and all that Southern Vermont has to offer. Inside, you'll find a bright, spacious open-concept layout with a comfortable living room, well-appointed kitchen with plenty of cabinet and counter space, dining area, and a generous primary bedroom with a private ensuite bath. Two additional bedrooms provide plenty of room for family, guests, a home office, or hobbies. With its modern construction, easy one-level floor plan, and move-in-ready condition, this home is an excellent choice for a year-round residence, vacation getaway, or affordable mountain retreat. Outside, the 1.4-acre property provides plenty of room for gardening, outdoor dining, recreation, or simply enjoying the surrounding woods and privacy. The location is hard to beat, close to Wilmington's shops and restaurants, Harriman Reservoir for boating and swimming, Lake Raponda, Haystack Golf Club, hiking and biking trails, and just a short drive to Mount Snow for winter skiing and year-round activities. If you're looking for a new, spacious, low-maintenance home in Southern Vermont without the price tag of a traditional site-built home, this one deserves a look. Spacious, immaculate, private, and move-in ready, come see all this 2025 home has to offer!

21 Lawrence Davis Dr, Wilmington
420 Ray Hill Rd, Wilmington
$1,725,000
6 Beds ⋅ 7 Baths ⋅ 5104414 MLS
This impressive 6-bedroom, 7-bath farm-style timber frame home, built by Davis Frame and featured on their website as “The Great White Barn,” sits on 3.51 acres just minutes from the Hermitage Club, Mount Snow, downtown Wilmington, lakes, hiking, golf, and VAST trails. Formerly known by its previous owners as “La Maison de Pommes” (House of Apples) for its old apple orchard setting, the home was designed for entertaining and guest stays. Fully furnished. The main level offers a magnificent great room, custom kitchen with large center island, stainless appliances, and walk-in pantry, plus a primary bedroom and additional bedroom. Upstairs, a large open loft serves as a relaxing retreat with flexible game-room or office space and another bedroom, featuring a one-of-a-kind slide to the main floor. Lower-level guest quarters can be separated by a barn door and include a kitchen/dining area, two family rooms, and three bedrooms with polished concrete floors. Every bedroom has a private bath. Outdoor living includes a spacious screened porch, private area with a Hot Spring Pulse 7-person hot tub, two decks with gas grill hookups, and a natural stone patio with an integrated fire pit. The backyard highlight is the beautiful apple orchard and blueberry bushes, along with peach trees and lilacs. This highly energy-efficient home features full geothermal heating and cooling, dual air exchangers, radiant flooring, and a masonry heater with pizza oven. Move right in and enjoy!

420 Ray Hill Rd, Wilmington
6 Church St, Wilmington
$239,900
2 Beds ⋅ 2 Baths ⋅ 5103642 MLS
Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home office, studio, or additional living area. Fidium high-speed fiber internet is already available on site, making it ideal for remote work or streaming. Connected to town water and sewer, the property offers added convenience and potential for future improvements, subject to local permitting and applicable town approvals. A new furnace was installed in May 2026, providing peace of mind for the next owner. Lovingly owned by the same family for the past 30 years, this home is ready for its next chapter. Being sold as is, it presents a wonderful opportunity for buyers with vision to update, personalize, and build equity in a highly desirable village location. All measurements are approximate, please conduct your own due diligence if important.

6 Church St, Wilmington
34 Rock Split Way, Wilmington
$520,342
3 Beds ⋅ 3 Baths ⋅ 5103126 MLS
Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, flows seamlessly into the open-concept dining area and kitchen, where a deck extends your living space for seasonal enjoyment. A main-floor bedroom with a private balcony and a full bathroom rounds out this level. Upstairs, you’ll find a bright, spacious bedroom with another private balcony and an en-suite bathroom. Additionally, a lofted bonus room that easily doubles as an office, media nook, or extra sleeping space. The walkout basement adds further versatility, featuring a third bedroom with an en-suite, a large den, with wet-bar, perfect for lounging, games, or fitness equipment, and a laundry room equipped with a workbench for DIY projects or gear maintenance. Outside, the property is as impressive as the interior, featuring thoughtfully landscaped grounds. Recent updates include a Generac whole-house generator, Mitsubishi mini-split, fiber optic internet service, and septic system improvements including a new riser and D-box. Chimney Hill is a recreationist’s dream, offering access to indoor and outdoor pools, tennis/pickleball courts, ice skating, and direct trail access to Haystack Summit, all with low HOA fees.

34 Rock Split Way, Wilmington
21 Big Bend Loop, Wilmington
$345,000
3 Beds ⋅ 2 Baths ⋅ 5102964 MLS
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.

21 Big Bend Loop, Wilmington
37 Stowe Hill Rd, Wilmington
$624,900
4 Beds ⋅ 3 Baths ⋅ 5102759 MLS
OPEN HOUSE Saturday, October 10th 2pm-4pm. Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm. Historic details abound, including authentic wood doors, wide-plank hardwood floors, and original wood trim. The spacious main level features a welcoming mudroom designed for year-round gear storage, a convenient half bath with laundry, and a beautifully updated kitchen complete with stainless steel appliances, a gas range, Silestone countertops, a center island, and a pantry. The formal dining room, private den with glass doors, and inviting living room with a cozy wood stove provide warm, comfortable spaces for gathering and entertaining. Upstairs, you'll find four generously sized bedrooms including the primary with ensuite full bath, soaking tub and separate shower. The versatile second-floor layout also offers excellent potential for a private guest or in-law suite. Outside, relax on the welcoming front porch or entertain on the expansive rear deck overlooking a peaceful backyard surrounded by rolling meadows, mature woodlands, private hiking trails, and more than 100 apple trees. Additional highlights include an attached two-car garage, a Tesla charging station and solar panels. Whether you're seeking a full-time residence, a Vermont getaway, or a hobby farm, Spruce Hill Farm offers an exceptional opportunity to enjoy the beauty, privacy, and lifestyle of southern Vermont.

37 Stowe 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
246 Mann Rd, Wilmington
$249,000
1 Beds ⋅ 5100124 MLS
Location, location, location! This rare opportunity is surrounded by the beautiful Haystack Golf Course, offering an unbeatable setting in one of southern Vermont's premier resort destinations. The property currently features a camp and a one-car garage, allowing you to enjoy the land immediately while planning your dream home or future getaway. Just minutes from Mount Snow, The Hermitage Club, golf, skiing, mountain biking, hiking, and year-round recreation, this parcel offers incredible potential for a vacation retreat, investment property, or primary residence. Opportunities in this location are few and far between. Don't miss your chance to own a piece of this sought-after area!

246 Mann Rd, Wilmington
88 Mann Rd, Wilmington
$5,998,000
5 Beds ⋅ 8 Baths ⋅ 5098574 MLS
A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At the heart of the home is a chef's kitchen complete with marble countertops, an oversized center island, walk-in pantry, dual Sub-Zero wine refrigerators, a built-in pizza oven, and a impressive suite of Wolf and Sub-Zero appliances. Designed for year-round enjoyment, the grounds are simply unmatched. Bluestone patios surround the home and lead to a sunken hot tub, cold plunge, a massive BBQ, pergola, children's playscape, and a spectacular post-and-beam open-air pavilion. Gather around the oversized fire pit while enjoying panoramic western sunsets over Haystack Mountain. Private tennis and pickleball courts, complete with a beautifully appointed cabana featuring a half bath, wet bar, and folding glass walls that open directly to the courts. A custom-built carriage house offers four oversized garage bays below for vehicles and seasonal recreational equipment. Above, guests will appreciate a beautifully finished two-bedroom apartment featuring an open-concept kitchen and living area, a gas fireplace, and a full bath ideal as guest accommodations, an in-law suite, or caretaker's quarters. The professionally landscaped grounds include a paved driveway, beautiful perennial plantings, rolling open field, and stunning views of Haystack Peak. Located just minutes from The Hermitage Club, Mount Snow, golf, skiing, dining, shopping, and all of Southern Vermont's year-round recreational amenities. This is more than a home—it's a legacy estate offering an unparalleled lifestyle where luxury, recreation, and Vermont's natural beauty come together in perfect harmony.

88 Mann Rd, Wilmington

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