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$249,900
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.

6 Church St, Wilmington
$599,000
5 Beds ⋅ 3 Baths ⋅ 5103360 MLS
Experience the best Vermont has to offer from this one of a kind spot just outside the country village of Wilmington, and a short drive to the Mount Snow Ski Resort, Hermitage Club, and nearby Lakes Whitingham and Raponda. This beautiful 16.2 acre property features rolling field, woodlands, vintage stone walls, mountain trailside views of Mount Snow, and complete privacy. The home has a large open concept floor plan with vaulted great room and floor to ceiling brick chimney, wood burning fireplace and wood stove, sunroom dining area with tremendous natural light, exposed post and beam woodwork throughout as well as wood floors, a unique custom kitchen with built in breakfast table, natural wood counters, farm sink, and stainless appliances, a main floor half bath for guests, a main floor bedroom currently used as a den, as well as a full bath with tiled shower and soaking tub, and mudroom entry for your gear, as well as large owner closet if you choose to rent, with laundry. The second floor has a loft open to below, and has 4 spacious bedrooms, including a lofted bunk room, tremendous views, and another full bath with soaking tub and stand up shower. The home has been lovingly updated by the current owners to feel turn key for immediate enjoyment. Less obvious features include a new stove in 2023, new ductless HW heater in 2021, upgraded electric 2021, new stove top 2024, new w/d 2021, recently added large front stone patio for enjoying the scenery and sunsets, rear dining patio overlooking perennial gardens, fenced in area ideal for pets, detached two car garage, direct snowmobile trail access, ample parking for guests and toys, and more. This is a perfect home away from home for anyone who wants Vermont at its best.

146 Minor Rd, 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
$354,900
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
$624,900
4 Beds ⋅ 3 Baths ⋅ 5102759 MLS
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, original wood trim, and a built-in corner cupboard. 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, quartz 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 a new drilled well scheduled for completion in September 2026. 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
$149,900
3 Beds ⋅ 1 Baths ⋅ 5102543 MLS
**AS-IS** Classic Chalet Near Mount Snow! Opportunity awaits with this classic chalet, ideally located just minutes from Mount Snow, The Hermitage Club, and the shops and restaurants of downtown Wilmington. Tucked among the trees, this charming retreat offers a peaceful setting with a spacious deck perfect for relaxing or entertaining. Inside, you’ll find three bedrooms, one full bath, and nostalgic retro details that add to the home’s vintage character. The property has remained in the same family for many years but has been unoccupied for over five years. The home is being sold **as is**. A pre-listing inspection has been completed and is available to help buyers better understand the property's condition and systems. Because the home has not been in use, the sellers have limited knowledge regarding the current functionality of the home’s systems. Whether you’re looking for a renovation project, a vacation getaway, or an investment opportunity in a desirable four-season location, close to some of the best ski mountains, golf courses, lakes, restaurants, and shopping in Southern Vermont, this chalet offers excellent potential! OFFER DEADLINE IS THURSDAY, AUGUST 6 AT 5 PM.

22 Ives Rd, Wilmington
$35,000
5101723 MLS
Nice building lot located in the Two Brook community, conveniently situated near Haystack Golf Course and just minutes from skiing, golf, lakes, and snowmobiling. This attractive parcel offers a peaceful setting with common land bordering the rear of the property and a stream flowing through the lot, adding to its natural appeal. Power, public water, and public sewer infrastructure are available nearby making this an excellent opportunity to build your Vermont getaway or year-round home. The property is ideally located for enjoying all that the Deerfield Valley has to offer, with easy access to outdoor recreation in every season. The Davis Brook Association fee is $75 per year for a vacant lot and $595 per year once a house is built. The Cold Brook Fire District fee is $75 per year for a vacant lot. A sewer hookup fee of $7,500 applies, followed by an annual fee of $1,443 once a house is connected.

8 Two Brook 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
$30,000
5101005 MLS
Section B building lot! 1/2 Acre of level, flat land at the end of the cul-de-sac. Site is untested. Build your dream home and start planning your vacation getaway design! As a Lot owner, you may enjoy all of the recreational amenities Chimney Hill Resort offers on its 1,200 Acre Campus. Once you start building, Chimney Hill Owners Association also supplies a water line at the street for you to connect to your home. The Deerfield Valley and Southern Vermont offer so many things to do, so if you decide to venture out from the CHOA Resort, you will find world class skiing and shredding, music, festivals, events, kayaking, paddleboarding, sailing, pontoon boating, golf, hiking, mountain biking, an extensive trail network, fine and casual dining, breweries, distilleries, and pickleball, flea markets, unique shops, an escape room, and so much more!

118 High Top Rd, Wilmington
$489,999
3 Beds ⋅ 2 Baths ⋅ 5100963 MLS
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.

7 High Top Rd Unit B-117, Wilmington
$319,000
3 Beds ⋅ 4 Baths ⋅ 5100908 MLS
Enjoy year-round Vermont living in this classic Spyglass townhome that is located right on the 10th fairway of the Haystack Golf course.  Offering 3 bedrooms plus a sleeping loft and 3.5 baths. Designed for comfort and convenience, the main level features a mudroom, an open-concept living and dining area with vaulted ceilings, a fully equipped kitchen, and a cozy wood-burning fieldstone fireplace. Step outside onto the deck to relax and enjoy the peaceful mountain setting. The upper level offers a versatile loft with its own private bath, ideal for additional sleeping space, a home office, or a guest suite. The lower level includes 3 comfortable bedrooms and two full baths. The Spyglass Association provides exceptional maintenance-free living, with dues covering landscaping, snow plowing, walkway shoveling, firewood delivered right to your door, and trash removal. Conveniently located just minutes from The Hermitage Club, Mount Snow Resort, Lake Whitingham, and the charming village of Wilmington, this property is an ideal four-season getaway, full-time residence, or investment opportunity. Walk to Hastack Golf Course clubhouse and the Stack restaurant.

12 Par Dr Unit 12, Wilmington
$499,000
3 Beds ⋅ 3 Baths ⋅ 5100662 MLS
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.

11 Dutchman Ln Unit 4A, 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
$599,000
4 Beds ⋅ 4 Baths ⋅ 5098734 MLS
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.

24 First Ln Unit 24, Wilmington
$6,898,000
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
$399,000
2 Beds ⋅ 1 Baths ⋅ 5098092 MLS
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. OPEN HOUSE AUGUST 9, 2026 11AM -1PM

456 Rte 100, Wilmington
$289,000
3 Beds ⋅ 2 Baths ⋅ 5098068 MLS
Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy trips to Mount Snow. The property features public water and sewer, a garage, paved driveway, two storage sheds, and plenty of lawn and garden space for outdoor enjoyment. Located just off a paved town road, you'll appreciate the quiet surroundings without sacrificing accessibility. Inside, you'll find generous living space with room to spread out, making it an ideal year-round residence or weekend retreat. Whether you're buying your first home, downsizing, or simply looking for an affordable way to enjoy all that Southern Vermont has to offer, this property is worth a look. With a motivated seller and a location that's hard to beat, this is an opportunity you won't want to miss.

5 Camelot Dr, Wilmington
$1,998,000
5 Beds ⋅ 5 Baths ⋅ 5097683 MLS
Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont’s Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern Green Mountains. With over 4,200 square feet of thoughtfully designed living space, the interior boasts clean lines, a Primary suite with walk-in closet and spa-like bath. Floating staircase, a large foyer, and a screened-in porch for enjoying warm evenings. Vaulted ceilings, radiant heat throughout, and walls of windows frame the stunning mountain and valley vistas. Open-concept kitchen and dining area with granite countertops, custom cherry cabinets and flooring, large center island, and a massive stone fireplace. Direct access to multi-level decks. Spacious living room with exposed beams and a cozy sitting area with a Projection System and a Custom high-end audiophile Sound system. Oversized heated 3-car garage. Enjoy outdoor living at its best with beautifully maintained flower gardens, open fields, a mature mixed forest, a patio, a hot tub, an outdoor shower, and creek frontage.

32 Steep Hill Rd, Wilmington
$115,000
5097175 MLS
Beautiful 5-Acre Vermont Lot with Mountain Views & Potential for Two Home Sites. Discover a rare opportunity to own a stunning 5-acre parcel in southern Vermont, ideally located on Route 100 just north of downtown Wilmington. This exceptional property offers the perfect setting for your dream home—or the potential to build two. Preliminary soil testing supports the potential for two separate single-family home sites, each accommodating up to a 3-bedroom residence, making this an attractive opportunity for homeowners, family compounds, or investment. The property features a beautiful open meadow bathed in sunshine, gently rolling terrain, and breathtaking views of the surrounding mountains and the Deerfield River. As a corner lot with road frontage on two sides, it offers convenient access and excellent flexibility for future development. Utilities are readily available at the road, including: Electric, Fiber-optic internet and telephone service. The property is also served by the MOOver public bus route, providing added convenience. Just minutes from downtown Wilmington, you'll enjoy easy access to charming local shops, restaurants, schools, and year-round recreation. Nearby you'll find lakes, golf courses, hiking trails, and some of southern Vermont's premier ski resorts, making this an ideal location for both full-time living and seasonal getaways. Whether you're envisioning a private mountain retreat, a family compound, or two thoughtfully positioned homes, this remarkable property combines natural beauty, development potential, and an unbeatable location. Don't miss this rare opportunity to build in one of southern Vermont's most desirable destinations.

Happy Haven Rd, Wilmington
$389,900
5097015 MLS
Sweet Country Retreat Near Mount Snow & The Hermitage Club Tucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity. Featuring five generous bedrooms, 2 bathrooms, Vaulted open concept living and incredible sun filled interior! This home provides plenty of space for family and friends to gather after a day on the slopes, trails, or nearby lakes. A walk-out lower level includes a separate second unit, offering flexibility for guest accommodations, multigenerational living, rental income, or a private home office. Outside, the property truly shines. Stunning perennial gardens burst with color throughout the seasons, creating a picturesque setting that complements the natural beauty of Southern Vermont. Relax on the deck, enjoy the peaceful surroundings, and take in the serenity of this special location. Whether you're seeking a ski home, vacation retreat, or year-round residence, this inviting Wilmington property offers space, versatility, and classic Vermont charm in an unbeatable location near some of the region's most sought-after mountain amenities. All STR permits in hand. See also MLS #5095088

88 Happy Haven Rd, Wilmington
$460,000
3 Beds ⋅ 2 Baths ⋅ 5096572 MLS
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.

216 Ghastly Job Way, Wilmington
$549,000
4 Beds ⋅ 2 Baths ⋅ 5095908 MLS
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.

7 Lightning Ledge Way, Wilmington
$399,000
3 Beds ⋅ 2 Baths ⋅ 5095784 MLS
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.

60 E Brook Xing, Wilmington
$699,000
5 Beds ⋅ 2 Baths ⋅ 5095170 MLS
Mountain views, meadow, a traditional barn, pure Vermont comfort — all wrapped into this beautifully renovated farmhouse. Just up from serene Lake Whitingham sits this stunning Vermont timber frame post-and-beam home, designed by Northern Energy Homes and set on a private 10-plus-acre parcel that feels worlds away while remaining effortlessly accessible. The grounds are exceptional. A handsome post-and-beam barn, an in-ground heated saltwater pool, hot tub, fire pit, and generous level lawn make the outdoor spaces as livable as the interior. The site looks west over the Vermont Forever Wild mountains and Harriman Reservoir, with easy access down the road to the Wards Cove beach area and boat launch. Completely renovated by the current owners, the home opens into a vaulted great room with natural exposed woodwork, a wood-burning stove, and rich wood floors — with views out every window. A well-appointed kitchen and dining area anchor the main living space, alongside two main-floor bedrooms, one currently used as a den, a full bath, and a versatile loft upstairs with an additional bedroom. The finished walkout lower level adds meaningful space, with a family room, two bedrooms, a full bath, and a well-organized mudroom with generous closets and laundry. From here, step out to the wraparound covered porch and hot tub, or climb the stairs to the deck overlooking the pool and sweeping lawn below. Wander through the mature blueberry plantings, head down to the lake for a swim, or take the short drive to the village of Wilmington and Mount Snow ski resort. The parcel is two approved building parcels so there is expansion potential as well. Whatever the season, this property delivers the full Vermont experience — beautifully. Septic sized for 3 bedrooms full time use.

389 Boyd Hill Rd, Wilmington
$2,100,000
7 Beds ⋅ 4 Baths ⋅ 5095153 MLS
Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and meticulous maintenance, this home is turn key for immediate enjoyment, with features including an open concept design, large great room with vaulting ceilings and exposed beams, a stone hearth with wood burning fireplace, upscale country kitchen with stainless appliances and granite counters, a secondary wet bar area, sizeable dining table for all your guests, wood floors throughout, a main floor primary suite with walk-in closets and large tiled bath, dual rustic bunk rooms, a lower level guest suite, 7 spacious bedrooms in total, a large family room for great separate entertaining space, movies, and games, as well as an adjacent tv area, and a tremendous mudroom with built in cubbies for all your gear after a day on the trails. There is also a large covered front porch to keep the snow at bay with wood storage, massive hot tub, fenced in dog area, generator, tremendous parking, and nice lawn space without being much to maintain. With proximity like this and creature comforts from home, this makes for a great ski home, as well as a welcome respite from the metropolitan bustle year round.

121 Fannie Hill Rd, Wilmington
$774,000
5095120 MLS
Multi-Family & Commercial Opportunity in Wilmington, Vermont Set on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing. The main building features updated interiors with modern kitchens, stylish baths, and new flooring throughout, combining contemporary finishes with a convenient, low-maintenance layout. The property has also been upgraded with a brand-new five-bedroom septic system, providing peace of mind and long-term value. Behind the main residence sits a spacious three-bay garage with a full upper level, ideal for a workshop, contractor space, or additional storage. A smaller outbuilding nearby offers even more flexibility for tools, recreational gear, or seasonal items. Whether you’re seeking an investment property, a home with income potential, or a commercial space with ample storage, this Wilmington location offers endless possibilities just minutes from Mount Snow Resort, Lake Whitingham, and the shops and dining of downtown Wilmington. On the MooVer Route

798 Vermont Route 100, Wilmington
$774,000
5 Beds ⋅ 3 Baths ⋅ 5095118 MLS
Multi-Family & Commercial Opportunity in Wilmington, Vermont Set on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing. The main building features updated interiors with modern kitchens, stylish baths, and new flooring throughout, combining contemporary finishes with a convenient, low-maintenance layout. The property has also been upgraded with a brand-new five-bedroom septic system, providing peace of mind and long-term value. Behind the main residence sits a spacious three-bay garage with a full upper level, ideal for a workshop, contractor space, or additional storage. A smaller outbuilding nearby offers even more flexibility for tools, recreational gear, or seasonal items. Whether you’re seeking an investment property, a home with income potential, or a commercial space with ample storage, this Wilmington location offers endless possibilities just minutes from Mount Snow Resort, Lake Whitingham, and the shops and dining of downtown Wilmington. On the MooVer Route

798 Vermont Route 100, Wilmington
$3,495,000
9 Beds ⋅ 11 Baths ⋅ 5095093 MLS
Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for generations. At the heart of the property is a beautifully maintained six-bedroom farmhouse that blends classic New England charm with thoughtful, energy-efficient upgrades. Warm wood floors, inviting gathering spaces, updated kitchens and baths, and period details throughout create a home that is both elegant and welcoming. A post and beam three-season room with a hot tub provides the perfect place to unwind while taking in the surrounding landscape. The property also includes a separate three-bedroom guest cottage, ideal for extended family, guests, caretakers, or rental opportunities. For entertaining on a grand scale, the impressive party barn features an expansive gathering space with kitchen facilities, an indoor basketball court, and room for everything from family celebrations to recreation and hobbies. The lower level, once the dairy barn, offers abundant storage for vehicles, recreational equipment, tools, and toys. Equestrian enthusiasts will appreciate the horse stables, fenced pasture areas, and open grounds, while outdoor lovers will enjoy the property's proximity to Lake Raponda, skiing, hiking, snowmobiling, and year-round recreation. Multiple outbuildings and flexible spaces create endless possibilities for agricultural use, workshops, or a private family compound. Whether envisioned as an equestrian estate, multigenerational retreat or four-season Vermont getaway, Green Meadows Farm presents an extraordinary opportunity to own one of the Deerfield Valley's most distinctive properties.

238 Stowe Hill Rd, Wilmington
$389,900
5 Beds ⋅ 2 Baths ⋅ 5095088 MLS
Sweet Country Retreat Near Mount Snow & The Hermitage Club Tucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity. Featuring five generous bedrooms, 2 bathrooms, Vaulted open concept living and incredible sun filled interior! This home provides plenty of space for family and friends to gather after a day on the slopes, trails, or nearby lakes. A walk-out lower level includes a separate second unit, offering flexibility for guest accommodations, multigenerational living, rental income, or a private home office. Outside, the property truly shines. Stunning perennial gardens burst with color throughout the seasons, creating a picturesque setting that complements the natural beauty of Southern Vermont. Relax on the deck, enjoy the peaceful surroundings, and take in the serenity of this special location. Whether you're seeking a ski home, vacation retreat, or year-round residence, this inviting Wilmington property offers space, versatility, and classic Vermont charm in an unbeatable location near some of the region's most sought-after mountain amenities.

88 Happy Haven Rd, Wilmington
$140,000
5094122 MLS
Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful natural setting for years to come. The property is ready for your vision with an approved Vermont wastewater permit for a 3-bedroom home, a gravity-fed septic design, and community water available at the road. Its topography provides an ideal homesite to maximize both seclusion and scenic surroundings. As part of the Chimney Hill Owners Association, enjoy year-round amenities including indoor and outdoor heated pools, a clubhouse with fitness center and hot tub, tennis and pickleball courts, hiking and snowmobile trails, an ice skating rink, fishing pond, playgrounds, and more. Conveniently located just minutes from Mount Snow, Lake Whitingham, and the shops and restaurants of Wilmington, this property offers the perfect balance of recreation, tranquility, and four-season Vermont living.

Scattered Timber Road, Wilmington

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