Houses for Sale in 05363

/37
$925,000
- 7 Beds
- 7.5 Baths
- 6,046 Sq Ft
214 Whites Rd, Wilmington, VT 05363

Experience a rare combination of proximity, privacy, and exposure, from this spectacular 1900s farmhouse nestled on 10+ private pastoral acres off the beautiful Whites Road, just outside the country village of Wilmington, and a short drive to the Mount Snow and Hermitage ski resorts. This home sits at the end of a private drive, with sunny exposure, horse pasture, rolling lawn space, and tennis

Adam Palmiter Berkley & Veller Greenwood/Dover

214 Whites Rd, Wilmington, VT 05363
/33
$979,000
- 4 Beds
- 5 Baths
- 2,320 Sq Ft
41 Two Brook Dr, Wilmington, VT 05363

Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Snow, snowmobile trails, 2 golf courses, historic village, and lake. Double lot w/sounds of Two Brook off back of home, patio, & hot tub, there is a newly updated chef's kitchen and accompaniments, plenty of room for diners, lovely gas fireplaces in both the large living room, and even larger family/game room.

Michael Purcell Berkley & Veller Greenwood/Dover

41 Two Brook Dr, Wilmington, VT 05363
/31
$947,000
- 5 Beds
- 3 Baths
- 3,015 Sq Ft
100 Mowing Way, Wilmington, VT 05363

Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

Leslie Fraser Four Seasons Sotheby's Int'l Realty

100 Mowing Way, Wilmington, VT 05363
/40
$809,000
- 3 Beds
- 3 Baths
- 3,606 Sq Ft
46 Scattered Timber Rd, Wilmington, VT 05363

Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows

Monique White Deerfield Valley Real Estate

46 Scattered Timber Rd, Wilmington, VT 05363
/35
$765,000
- 3 Beds
- 2 Baths
- 2,170 Sq Ft
27 Stearns Ave, Wilmington, VT 05363

Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

John Redd Skihome Realty

27 Stearns Ave, Wilmington, VT 05363
/59
$675,000
- 4 Beds
- 2 Baths
- 2,540 Sq Ft
42 View Rd, Wilmington, VT 05363

Welcome to your turnkey Vermont chalet in the heart of Chimney Hill. Situated on a rare double lot, this spacious 6-bedroom, 3-bath mountain home offers approximately 2700 square feet* of finished living space including a heated oversized garage with a fully finished bonus level ideal for guests, hobbies, or remote work. Vaulted pine ceilings, a central skylight, and a wood-burning brick

Nick Sicard EXP Realty

42 View Rd, Wilmington, VT 05363
/28
$589,000
- 5 Beds
- 3.5 Baths
- 2,240 Sq Ft
47 Ives Rd, Wilmington, VT 05363

Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

Adam Palmiter Berkley & Veller Greenwood/Dover

47 Ives Rd, Wilmington, VT 05363
/49
$435,000
- 4 Beds
- 2 Baths
- 1,344 Sq Ft
27 Country Ct, Wilmington, VT 05363

Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

Janet Boyd Boyd Real Estate

27 Country Ct, Wilmington, VT 05363
/32
$559,000
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
9 Greer Ct, Wilmington, VT 05363

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

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Greer Ct, Wilmington, VT 05363
/31
$2,100,000
- 7 Beds
- 4 Baths
- 4,256 Sq Ft
121 Fannie Hill Dr, Wilmington, VT 05363

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

Adam Palmiter Berkley & Veller Greenwood/Dover

121 Fannie Hill Dr, Wilmington, VT 05363
/60
$499,999
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
47 Upper Howes Way Unit A-23, Wilmington, VT 05363

On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities

Sigrid Pickering Chimney Hill Realty

47 Upper Howes Way Unit A-23, Wilmington, VT 05363
/30
$499,900
- 2 Beds
- 1.5 Baths
- 1,416 Sq Ft
6 Gates Ln, Wilmington, VT 05363

Welcome to your idyllic escape with private dock on the shores of beautiful Lake Raponda. This cozy 2 bedroom 1.5 bath house offers the perfect blend of rustic charm and modern comfort, nestled in a peaceful wooded setting minutes from downtown Wilmington and a short walk to your waterfront dock!Step inside to discover warm wood accents, open concept living and dining area on the main level

Heidi Zizza Four Seasons Sotheby's Int'l Realty

6 Gates Ln, Wilmington, VT 05363
/60
$2,195,000
- 5 Beds
- 4.5 Baths
- 4,200 Sq Ft
32 Steep Hill Rd, Wilmington, VT 05363

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

Richard Caplan Deerfield Valley Real Estate

32 Steep Hill Rd, Wilmington, VT 05363
/19
$499,000
- 4 Beds
- 2 Baths
- 1,056 Sq Ft
48 Landing Ln, Wilmington, VT 05363

Private boat slip and beach access from this charming contemporary home just off Lake Raponda and a short drive to the Mount Snow ski resort. Enjoy the best of both worlds with easy access to summer boating, swimming, tennis, and outdoor activities for the summer, just a short drive from skiing and with direct snowmobile trail access. This 2003 home sits privately on a 4.35 acre lot with

Adam Palmiter Berkley & Veller Greenwood/Dover

48 Landing Ln, Wilmington, VT 05363
/57
$2,595,000
- 4 Beds
- 4 Baths
- 3,585 Sq Ft
127 Fannie Hill Dr, Wilmington, VT 05363

Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

127 Fannie Hill Dr, Wilmington, VT 05363
/35
$399,000
- 4 Beds
- 2 Baths
- 1,768 Sq Ft
1469 Higley Hill Rd, West Marlboro, VT 05363

Cozy Log Cabin with Sunny Addition, Small Pond & Sugar House on 5 Acres in Marlboro, VermontThis inviting log cabin blends classic Vermont charm with a thoughtfully designed, light-filled addition—offering comfort, space, and versatility on 5 peaceful acres. Tucked away on a quiet dirt road in a desirable Marlboro neighborhood, the property features a small pond and a traditional sugar house,

Melissa Nebelski Skihome Realty

1469 Higley Hill Rd, West Marlboro, VT 05363
/60
$555,000
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
22 Lower Howe's Rd Unit A89, Wilmington, VT 05363

Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living,

Sigrid Pickering Chimney Hill Realty

22 Lower Howe's Rd Unit A89, Wilmington, VT 05363
/32
$1,697,000
- 4 Beds
- 3 Baths
- 2,420 Sq Ft
197 Lake Raponda Rd, Wilmington, VT 05363

This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

Adam Palmiter Berkley & Veller Greenwood/Dover

197 Lake Raponda Rd, Wilmington, VT 05363
/35
$549,000
- 3 Beds
- 2 Baths
- 2,136 Sq Ft
8 Lilla Ln, Wilmington, VT 05363

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled on a serene wooded lot in the Chimney Hill community. Set back from the road for added privacy, this home offers a perfect blend of comfort and style. As you step inside, a spacious two-room addition, currently used by the seasonal owners for additional sleeping, expands the living space to over 2,100 square feet. The

Patricia Fitzpatrick Skihome Realty

8 Lilla Ln, Wilmington, VT 05363
/5
$210,000
- 2 Beds
- 1 Bath
- 560 Sq Ft
1570 Somerset Rd, Wilmington, VT 05363

Somerset Wilderness,Close to the reservoir and Deerfield River. Boating. snowmobiling, hunting, and hiking. Open land with trails and apple trees. Abuts the National Forest.

Mark Yule BHG Masiello Brattleboro

1570 Somerset Rd, Wilmington, VT 05363
/53
$1,200,000
- 4 Beds
- 3 Baths
- 3,506 Sq Ft
339 Coldbrook Rd, Wilmington, VT 05363

Just a half mile from The Hermitage Club, 3.5 miles to Mount Snow, and only a mile from Haystack Golf Club, this 4 bedroom, 3 bathroom home on 10.1 acres offers the perfect blend of rustic charm and modern comfort. Direct access to the VAST snowmobile trails and mountain views makes this an outdoor enthusiast’s dream.Step inside to find warm wood finishes, exposed beams, and rich natural textures

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

339 Coldbrook Rd, Wilmington, VT 05363
/60
$425,000
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363

New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight

Sigrid Pickering Chimney Hill Realty

96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
/43
$398,000
- 6 Beds
- 2 Baths
- 960 Sq Ft
247 Vt Route 100 N, Wilmington, VT 05363

Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

Janet Boyd Boyd Real Estate

247 Vt Route 100 N, Wilmington, VT 05363
/31
$445,000
- 4 Beds
- 3 Baths
- 1,854 Sq Ft
132 Sun and Ski Rd, Wilmington, VT 05363

Welcome to Chateau Chelsea! This charming three-level, 4-bedroom, 3-bathroom single-family home is situated in the heart of Vermont’s picturesqueGreen Mountains. Named after the owners' beloved pup, this property has been a cherished gathering place for family and friends year-round. Conveniently located just over 2 hours from Boston, 90 minutes from Hartford, CT, and less than 4 hours from NYC,

Patrice Schneider Southern Vermont Realty Group

132 Sun and Ski Rd, Wilmington, VT 05363
/39
$499,000 Open Sat 1:30PM - 3:30PM
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
156 Mountain View Rd, Wilmington, VT 05363

This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

Jennifer Hovey-Densmore Deerfield Valley Real Estate

156 Mountain View Rd, Wilmington, VT 05363
/31
$499,000
- 3 Beds
- 2 Baths
- 2,372 Sq Ft
285 Chimney Hill Rd, Wilmington, VT 05363

Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

Monique White Deerfield Valley Real Estate

285 Chimney Hill Rd, Wilmington, VT 05363
/23
$499,000
- 3 Beds
- 2.5 Baths
- 1,548 Sq Ft
28 Lightning Ledge Way, Wilmington, VT 05363

Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Lightning Ledge Way, Wilmington, VT 05363
/27
$3,125,000
- 4 Beds
- 4 Baths
- 2,740 Sq Ft
56 Coldbrook Crossing, Wilmington, VT 05363

Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

Adam Palmiter Berkley & Veller Greenwood/Dover

56 Coldbrook Crossing, Wilmington, VT 05363
/60
$335,000
- 3 Beds
- 1 Bath
- 1,150 Sq Ft
108 Spruce Grove Rd Unit M286, Wilmington, VT 05363

This house sits on a lot that is surrounded by common land so it feels very secluded and private. Newer septic, roof, and main level flooring, and the prior owner did a lot of custom wood paneling with built-ins, and creative decorating which add to its charm. The main level has a mudroom entry with laundry and storage space, full bath, kitchen with open shelving above and cabinets below, newer

Sigrid Pickering Chimney Hill Realty

108 Spruce Grove Rd Unit M286, Wilmington, VT 05363
/27
$559,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
16 View Rd, Wilmington, VT 05363

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

16 View Rd, Wilmington, VT 05363
/35
$795,000
- 4 Beds
- 5 Baths
- 3,129 Sq Ft
20 Ray Hill Rd, Wilmington, VT 05363

Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Ray Hill Rd, Wilmington, VT 05363
/41
$725,000
- 3 Beds
- 3.5 Baths
- 4,219 Sq Ft
5 N Main St, Wilmington, VT 05363

Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

Morriah Adams BHG Masiello Brattleboro

5 N Main St, Wilmington, VT 05363
/59
$529,000
- 3 Beds
- 2.5 Baths
- 1,736 Sq Ft
30 Big Bend Loop, Wilmington, VT 05363

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

30 Big Bend Loop, Wilmington, VT 05363
/41
$265,000
- 4 Beds
- 1 Bath
- 1,612 Sq Ft
178 Parsons Rd, Wilmington, VT 05363

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

Jennifer Hovey-Densmore Deerfield Valley Real Estate

178 Parsons Rd, Wilmington, VT 05363
/45
$275,000
- 3 Beds
- 1.5 Baths
- 1,728 Sq Ft
121 Happy Haven Rd, Wilmington, VT 05363

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, a

Jennifer Hovey-Densmore Deerfield Valley Real Estate

121 Happy Haven Rd, Wilmington, VT 05363
/28
$520,000
- 6 Beds
- 3.5 Baths
- 2,766 Sq Ft
624 Boyd Hill Rd, Wilmington, VT 05363

Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s

Jason Saphire www.HomeZu.com

624 Boyd Hill Rd, Wilmington, VT 05363
/32
$499,000
- 7 Beds
- 5 Baths
- 2,718 Sq Ft
343 Haystack Rd, Wilmington, VT 05363

This spacious home is located near Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers Four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone

Jessica Citera Cummings & Co

343 Haystack Rd, Wilmington, VT 05363
/28
$895,000
- 4 Beds
- 3 Baths
- 1,482 Sq Ft
19 Village Rd E, Wilmington, VT 05363

Here is a chance to own a home directly across the street from the private Hermitage Ski Club with easy access to the resort, snowmobile trails, the Mount Snow ski resort, nearby country villages for shopping and dining, and gorgeous area lakes. This lovely renovated chalet sits on a level with ample parking thanks to a circular driveway, winter exposure to Haystack Mountain Peak, a shed for

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Village Rd E, Wilmington, VT 05363
/42
$849,000
- 4 Beds
- 3.5 Baths
- 2,953 Sq Ft
37 Pleasant View Ln, Wilmington, VT 05363

4 bed, 3.5 bath, true log home w/excellent layout over 3 finished floors, 2 car garage, 5 acres, private pond, Mount Snow views, snowmobile trail access and all nicely tucked away on a dead end road. Just 2.2 miles to Rt 100 for easy access to downtown Wilmington shops and dining, Mount Snow Resort, the exclusive Hermitage Club, Harriman Reservoir and marina and multiple area golf courses. Even

Jacki Murano Southern Vermont Realty Group

37 Pleasant View Ln, Wilmington, VT 05363
/40
$849,000
- 5 Beds
- 3.5 Baths
- 3,436 Sq Ft
67 Castle Hill Rd, Wilmington, VT 05363

Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

Adam Palmiter Berkley & Veller Greenwood/Dover

67 Castle Hill Rd, Wilmington, VT 05363

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