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6 Longest Dr Unit 1, Wilmington
$319,000
3 Beds ⋅ 3 Baths ⋅ 5073493 MLS
Turn key renovated 3+ bedroom, 2.5 bath townhouse just off the Haystack Golf Club 10th hole, with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club and Mount Snow ski resorts. This unit has been completely renovated throughout and is being sold for immediate enjoyment. Features include a vaulted living room area with stone fireplace, great natural light through many large windows, a spacious dining area with slider out to the entertaining deck, safe from errant balls, a new custom kitchen with quartz counters, stainless appliances, and custom cabinets, guest half bath on the main floor, and a large mudroom for all your gear no matter the season. Upstairs is a sleeping loft currently being used as a family room complete with sleeper sofa, games, television, and owners closet. The lower level has a primary bedroom suite with tiled bath and barn door feature, there is a second bunk room with futon, as well as a bonus room currently set up for more sleeping, and a 3rd full bath with stand up shower. Amenities include snow removal, landscaping, building maintenance, and trash. There is an ongoing project to replace windows and siding that will ultimately improve the overall exterior aesthetic, and has been factored into the price. Easy access to and from the adjacent golf course, which is great for trail access for hiking and cross country skiing year round, as well as the nearby Hermitage Club and Mount Snow ski resorts, and nearby village of Wilmington. A great price for great space!

6 Longest Dr Unit 1, Wilmington
43 First Ln Unit 25, Wilmington
$307,000
2 Beds ⋅ 2 Baths ⋅ 5052237 MLS
Get ready to fall in love with this charming, updated condo, with an unbeatable location right next to the 1st green of Haystack Golf Course. Imagine waking up every morning to a stunning mountain view, the serene golf course scenery, & ending your day with breathtaking sunsets & peaceful evenings. This turnkey unit is ready to impress & welcome you home. Upon entering, you'll discover a contemporary kitchen with stainless steel appliances & granite countertops. The well-appointed dining area flows seamlessly into a spacious living room, complete with a cozy wood-burning fireplace. A door leads out to the deck, offering a dream view. The condo features two tastefully decorated bedrooms, each with an updated en-suite bath featuring granite countertops. The primary boasts private access to the deck, a generously sized window for natural light, a jacuzzi bath tub & a walk-in closet. For added convenience, the condo includes a stackable washer/dryer, generous closet space & a ski/golf locker just outside the front door. The Haystack Golf Course, home to 18 holes & The Stack Restaurant, is just a stone's throw away. Country Club Village condos are close to 2 world-class resorts, Mount Snow & the Hermitage, plus the village of Wilmington for a variety of shopping & dining options. When you're not on the golf course, enjoy nearby lakes, mountain biking/hiking, & more. Don't miss out on this opportunity to enjoy year-round beauty & convenience for both golfers and skiers alike.

43 First Ln Unit 25, Wilmington
91 Happy Haven Rd, Wilmington
$301,000
4 Beds ⋅ 2 Baths ⋅ 5055996 MLS
A solid home in a great location in Wilmington Vermont! Currently set up as a duplex. Live in one and rent the other or have family close by! Add internal stairs and use as one! This is a classic Chalet with the ease of a metal roof, large deck, 2 bedrooms and a full bathroom upstairs along with a cathedral ceiling, cute sleeping loft and built ins! The lower level is 2 bedrooms and a full bathroom with large combined kitchen/living and dining room. There is a large wood shed and an even larger garage/shed/barn. Enjoy your days on the oversized front deck and your evenings by the fire pit! The wooded area behind the home is great for exploring! So close to the local towns, ski areas, lakes and ALL!

91 Happy Haven Rd, Wilmington
5 First Ln Unit 1, Wilmington
$280,000
2 Beds ⋅ 2 Baths ⋅ 5051833 MLS
Owner open to offers. Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are treated to an open concept living space large living and dining areas, wood burning fireplace with stone hearth, new vinyl plank flooring, large kitchen with breakfast bar, primary suite with walk in closet, full bath, stand up shower and soaking tub, guest bedroom with jack and jill bath, nice light throughout, and a covered rear porch to take in the views. There is also a ski locker for gear and ample parking. The Haystack restaurant is currently open year round for dinner, affording a convenient dining option. There is also easy upkeep thanks to community living with landscaping, snow removal, wood, trash service, and more. This one won't last long!

5 First Ln Unit 1, Wilmington
40 Arctic Cir Unit M073, Wilmington
$276,000
4 Beds ⋅ 2 Baths ⋅ 5094433 MLS
Split Level on the Hill! This modest home retains its vintage character and has a lot of features in a compact space. 3+ bedrooms, 2 baths, open concept living, dining and kitchen, stacked laundry in the mudroom foyer, a deck off the living room, a wood stove, and two propane wall unit heaters. A babbling brook outside makes for a tranquil getaway setting. Priced to sell. There may be an opportunity to expand the lot by purchasing additional land from the CHOA. Enjoy all the amenities Chimney Hill offers including seasonal ice skating, tennis and pickleball, year-round swimming, multiple use trail system situated on CHOA's 1,200 Acre Resort Campus with 550 Acres owned in common by members, stocked fishing pond, playground, clubhouse, hiking, biking, snowmobiling in designated areas, and so much more! Plus, the Resort is minutes from world class skiing and shredding at the private Hermitage Club or Vail's Mt Snow, artists, crafts, breweries, distilleries, boating, golf, links, lakes, paddleboarding, mountain biking, music, theater, antiques, fine dining, flea markets and so much more!

40 Arctic Cir Unit M073, Wilmington
876 Rte 100, Wilmington
$250,000
3 Beds ⋅ 2 Baths ⋅ 5061227 MLS
Great location for full-time local residents or seasonal visitors. Easy access from Route 100. Nice yard and solid house. This is a comfortable 3-bedroom house with a living room, kitchen, and dining room! Centrally located and easily accessible. Please come see it!

876 Rte 100, Wilmington
8 Happy Haven Rd, Wilmington
$245,000
3 Beds ⋅ 2 Baths ⋅ 5066543 MLS
Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car garage. Wonderful neighborhood on a private road. Nice floorplan!!!

8 Happy Haven Rd, Wilmington
11 Hassey Bnd Unit 9, Wilmington
$239,000
2 Beds ⋅ 2 Baths ⋅ 5076844 MLS
Ready to move in Mountain Ponds end unit Townhouse with 2 bedroom plus loft and 1 1/2 bathsMain level boasts an open concept living/dining and renovated kitchen area. Relax on the back deck off dining area. Gas stove in the living room. Attached ski locker/wood bin with 2 entrances. Spacious mudroom. Direct access to VAST snowmobile trail and adjacent to Haystack Golf Course. Lake Whitingham is nearby for canoeing, boating, kayaking and fishing. Association dues conveniently cover walkwayshoveling, plowing, firewood, landscaping, annual chimney cleaning, and trash removal. Perfectly located near Haystack Mountain and a wealth of outdoor recreationopportunities, including hiking, biking, golfing, snowmobiling, and snowshoeing. Downtown Wilmington’s shops and restaurants are just minutes away, and Mount Snowis only 3 miles from your door. Make this inviting townhouse your Vermont retreat.

11 Hassey Bnd Unit 9, Wilmington
121 Happy Haven Rd, Wilmington
$237,000
3 Beds ⋅ 2 Baths ⋅ 5041166 MLS
This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace & mini split, a dining area, sitting area, a galley kitchen, and a half bath. Upstairs, you’ll find three bedrooms and a full bath. One of the bedrooms is generously sized and includes its own fireplace for added comfort. The home has been enlarged and partially completed creating an extra living space with mini split on the first floor (20x20) and additional space upstairs (10x20). The former garage has been converted into a functional workshop with concrete floor. Spacious front lawn with a BBQ pit and side yard seating—perfect for relaxing and enjoying the peace and quiet. The wooded backyard features a hunter’s tree stand and trails for added outdoor appeal. The property also includes a woodshed, chicken coop, and lean-to for ample outdoor storage. Home is being sold as is, offering a great opportunity to add your own touch.

121 Happy Haven Rd, Wilmington
178 Parsons Rd, Wilmington
$225,000
4 Beds ⋅ 1 Baths ⋅ 5042206 MLS
Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The home welcomes you with a classic covered front porch and a practical mudroom entry. Inside, the spacious kitchen flows into a flexible dining/den area, with a bright three-season sunroom just off the dining space—perfect for relaxing or entertaining. The main level also offers a cozy living room, a bedroom, and a full bath, ideal for single-level living. Upstairs, you’ll find three additional bedrooms, providing plenty of space for family or guests. This property blends comfort, convenience, and outdoor living in a peaceful country setting.

178 Parsons Rd, Wilmington
394 Haystack Rd Unit 2, Wilmington
$220,000
2 Beds ⋅ 2 Baths ⋅ 5047574 MLS
Enjoy four-season living in this inviting 2-bedroom, 1.5-bath townhome just a short walk to Haystack Golf Course. Set in a peaceful location with direct Valley Trail and snowmobile access, this well-cared-for home is part of a small HOA with low fees. The main level offers a spacious open layout featuring a cozy wood stove on a slate hearth—perfect for watching the fire roar after a day on the slopes—along with a large kitchen with breakfast bar and new dishwasher, dining area with a new slider to the private back deck, half bath, and a generous mudroom ideal for firewood and ski storage. Upstairs you’ll find two generously sized bedrooms with vaulted ceilings, including one set up as a bunk room, plus a full bath and laundry area with new washer and dryer. Recent crawl space and foundation improvements include wall repair, a vapor barrier, drainage, and dehumidifier. Minutes to Mount Snow, Wilmington village, Route 9, and Harriman Reservoir, this low-maintenance getaway is your base for year-round adventure.

394 Haystack Rd Unit 2, Wilmington
22 Ives Rd, Wilmington
$210,000
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
Hillside Dr, Wilmington
$200,000
4998188 MLS
Discover Your Private Vermont Retreat – 34 Acres of Possibility and Peace A rare opportunity awaits to own an expansive 34.0-acre parcel offering tremendous privacy, breathtaking views, and endless potential. Nestled amidst rolling topography with picturesque stone walls and a network of historic trails, this unique property invites exploration and inspiration at every turn. Two potential homesites have been identified near the point of entry, while a more adventurous path leads you to a mountaintop plateau—the ideal setting to capture panoramic views of Haystack Mountain and Mount Snow with selective clearing. Partial driveway provides easy access into the property. Currently enrolled in the Vermont Current Use Program, the land includes a Forestry Management Plan and features stands of Northern hardwoods and Hemlock, with some marketable timber on site. Though perfectly private, the location remains convenient to all that Wilmington has to offer—from shopping and dining in the village, to water recreation on Lake Whitingham, and year-round adventure at Haystack and Mount Snow for skiing, golf, and more. Whether you're dreaming of a secluded mountain getaway, an off-grid homestead, or a legacy property for generations, this is your chance to create your own piece of Vermont paradise.

Hillside Dr, Wilmington
406 Fox Mt Rd, Wilmington
$120,000
5035688 MLS
Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, the CHOA exclusive members-only Clubhouse located near the top of Chimney Hill at 2.000' in elevation, with year-round swimming in our heated pools, hot tub, lounge, arcade, fitness room, community room, fully equipped kitchen, reading nook, and toddler playroom. The CHOA Resort covers 1,200-Acres, with 300-Acres owned in common by the HOA. The common land has 3 tennis courts, seasonal pickleball and ice skating, an extensive trail system for hiking, snowmobiling, and playing, a fishing pond, and the trailhead to Haystack Mountain. Music festivals, theater, arts and crafts tours, flea market, fine dining, unique shopping, antiques, breweries, distilleries, wineries, boating, golf, bicycling and more - heck, you can hike from Chimney Hill to Mt Snow on the Valey Trail too!

406 Fox Mt Rd, Wilmington
408 Fox Mt Rd, Wilmington
$120,000
5035898 MLS
Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, the CHOA exclusive members-only Clubhouse located near the top of Chimney Hill at 2.000' in elevation, with year-round swimming in our heated pools, hot tub, lounge, arcade, fitness room, community room, fully equipped kitchen, reading nook, and toddler playroom. The CHOA Resort covers 1,200-Acres, with 300-Acres owned in common by the HOA. The common land has 3 tennis courts, seasonal pickleball and ice skating, an extensive trail system for hiking, snowmobiling, and playing, a fishing pond, and the trailhead to Haystack Mountain. Music festivals, theater, arts and crafts tours, flea market, fine dining, unique shopping, antiques, breweries, distilleries, wineries, boating, golf, bicycling and more - heck, you can hike from Chimney Hill to Mt Snow on the Valey Trail too!

408 Fox Mt Rd, Wilmington
410 Fox Mt Rd, Wilmington
$80,000
5036114 MLS
Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all the amenities Chimney Hill, the DeerfieldValley and Southern Vermont offer including world class skiing and shredding, the CHOA exclusive members-only Clubhouse located near the top of Chimney Hill at 2.000' in elevation, with year-round swimming in our heated pools, hot tub, lounge, arcade, fitness room, community room, fully equipped kitchen, reading nook, and toddler playroom. The CHOA Resort covers 1,200-Acres, with 300-Acres owned in common by the HOA. The common land has 3tennis courts, seasonal pickleball and ice skating, an extensive trail system for hiking, snowmobiling, and playing, a fishing pond, and the trailhead to Haystack Mountain. Music festivals, theater, arts and crafts tours, flea market, fine dining, unique shopping, antiques, breweries, distilleries, wineries, boating, golf, bicycling and more - heck, you can hike from Chimney Hill to Mt Snow on the Valley Trail too!

410 Fox Mt Rd, Wilmington
169 Sun And Ski Rd, Wilmington
$65,000
5077813 MLS
Located just 7 minutes from downtown Wilmington, 8 minutes from the village of Marlboro, 24 minutes from Brattleboro, and less than 20 minutes from Mount Snow and The Hermitage Club, this one-acre parcel blends rural Vermont living with convenient access to year-round recreation, dining, and shopping. In the charming Vermont village of downtown Wilmington, enjoy fresh pastries from the local bakery, small-batch roasted coffee, boutiques, an independent bookstore, and cozy spots to gather for great food and drink. Outdoor recreation surrounds you. Within 15 minutes, you'll have access to Lake Raponda, Harriman Reservoir, and Lake Sadawga for swimming, boating, kayaking, paddleboarding, and fishing. Harriman Reservoir is also home to High Country Marine, where you can launch your own boat or rent a motorized boat for the day. Less than a mile away, Hogback Mountain offers breathtaking 100-mile panoramic views, a classic Vermont country store, seasonal maple creemees, a local brewery, and a distillery. While you're there, hike to the Mt. Olga Fire Tower through the former Hogback Ski Area for another spectacular overlook. Spend weekends exploring the flea market, teeing off at nearby golf courses, or riding the area's extensive network of mountain biking trails. With several significant steps in the preparation process already done, this one-acre lot is truly ready for your vision. A three-bedroom septic design by a Vermont engineer has been completed, with permits filed and approved by the state of Vermont. Plus, the land has already been partially cleared for a driveway and building site and an address has been established. In addition to the lot prep and approved septic design permitting, a town zoning permit has already been approved for a one-bedroom tiny home if that's of interest.

169 Sun And Ski Rd, Wilmington
Lot 4 Ghastly Job, Wilmington
$52,000
5034624 MLS
3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham for boating, Mount Snow Ski Resort and area golf. High speed internet availability. This property is the perfect location for either the primary homeowner or a get-away vacation retreat.

Lot 4 Ghastly Job, Wilmington
22 W Main St Unit B, Wilmington
$50,000
5051138 MLS
Here’s your opportunity to live and work in Vermont! Pickwell’s Barn is a profitable women’s wear boutique nestled in the picturesque village of Wilmington, Vermont, where customers from all over come to walk, shop, and dine. You’ll be captivated by the stylish selection of comfortable yet chic women’s clothing, accessories, and home furnishings, each selected to appeal to the diverse mix of local and out-of-town buyers. Pickwell’s has been a key retail shop in town for nearly 35 years, establishing a loyal base of repeat customers who visit frequently. The owner is now ready to turn her business over to talented new blood to build on its success by leveraging the mailing list using social media and the internet. A turn-key operation with a consistent track record of profitability, she’ll provide all the training you need to feel comfortable operating your own business. With Mt. Snow nearby, Wilmington is the premier year-round resort town in southern Vermont, located within a few hours' drive of NYC, Boston, CT, NJ, and Western MA. With 70% of area homes being second homes, condos and hotels supplement the population of recreational vacationers with disposable income and leisure time to shop. If you dream of being your own boss and living a relaxed lifestyle, this is a rare opportunity to make it real. Available now for $60,000 plus inventory at cost.

22 W Main St Unit B, Wilmington
00 Two Brook Dr, Wilmington
$45,000
5050731 MLS
Prime building opportunity in the heart of Vermont's four season playground! Flat lot w/enviable location near Haystack Golf Course & scenic Valley Trail. This parcel boasts not only a great location but also added convenience w/power, public water & sewer infrastructure nearby. Past waste water permits and design on file for building will need to be updated but are available for review. Vibrant downtown Wilmington beckons with its eclectic array of shops, dining and entertainment just minutes away. Conveniences like grocery stores, pharmacy, medical center are also near the village. Lake Whitingham's ( Harriman Reservoir) Marina is just a few miles and offers a gateway to aquatic adventures, motorboating or enjoying tranquil kayaking excursions. Nature enthusiasts will appreciate the proximity to national forest, hiking trails, and snowmobile trails right are at the entrance of the private drive loop. For winter sports enthusiasts, Mount Snow Resort, Prospect Mountain and exclusive Hermitage Club are mere minutes away. This property presents an exceptional blend of convenience, and recreational amenities, making it an enticing investment opportunity or an idyllic location to investigate building your dream home. Don't miss out on the chance to experience the best of Wilmington's ( and Vermont's!) lifestyle offerings.

00 Two Brook Dr, Wilmington
9 Sun And Ski Rd, Wilmington
$35,000
5065936 MLS
Prime Land Lot – Minutes from Wilmington, Close to Mount Snow! Discover the perfect blend of seclusion and convenience with this exceptional land opportunity, ideally located just 8 minutes from Main Street Wilmington and only 20 minutes from the slopes of Mount Snow. Whether you're dreaming of a private mountain getaway, a cozy Airbnb investment, or building your forever home, this lot offers the versatility to make it happen. Nestled near the Massachusetts border and under 30 minutes from Brattleboro, this location provides easy access to four-season recreation, charming Vermont towns, and major travel routes—making it a hidden gem for both personal use and income potential. Enjoy nearby skiing, hiking, lakes, shopping, and dining—all within a short drive—while still having the peace and privacy of your own slice of Vermont wilderness.

9 Sun And Ski Rd, Wilmington

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