Wilmington, VT Homes for Sale

/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
/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
/28
$625,000
- 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
/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
/33
$550,000
- 3 Beds
- 2 Baths
- 1,688 Sq Ft
19 Titus Farm Rd, Wilmington, VT 05363

The epitome of a Vermont country home, yet just outside the village of Wilmington, down the road from Lake Raponda, and a short drive the Mount Snow ski resort. This lovely 5+ acre property has a beautiful gurgling brook running through it, gorgeous stone work including old walls and an old stone bridge, trails through the pastoral setting, fire pit area, perennial gardens, and utter privacy.

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Titus Farm Rd, Wilmington, VT 05363
/47
$249,000
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
5 Camelot Dr, Wilmington, VT 05363

This 3-bedroom, 2-bath manufactured home on .43 acres offers flexibility and potential, currently set up as two separate 1-bedroom units—ideal for rental income, guests, or an easy conversion back to a single residence. The property features a nice lawn area, two storage sheds, a one-car garage with plenty of space inside, and a paved driveway for convenience. Located in a quiet section of town

Chad Lackey Deerfield Valley Real Estate

5 Camelot Dr, Wilmington, VT 05363
/20
$375,000
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
43 Bear Lair Ln, Wilmington, VT 05363

Nestled up against the tree line, this 3 bedroom 2 bath home offers a slice of privacy at the end of a dead-end road near the top of Chimney Hill. The current owner has opened the yard to let in more light and make it much more user friendly and functional. The driveway was expanded into a circular drive-through. Reduce your electricity costs with the new PV solar array on the roof that will

Jim Bellville Bellville Realty

43 Bear Lair Ln, Wilmington, VT 05363
/12
$29,000
- Land
- 0.47 Acre
- $61,702 per Acre
0 Elwell Heights Dr, Wilmington, VT 05363

.47 acre wooded parcel located just across the road from the Castle Hill picnic and boat launch area on Harriman Reservoir in Wilmington. Enjoy water skiing, boating, canoeing, kayaking, fishing and swimming just steps away. This is the perfect spot for a garage or shed to store the boats or an off grid cabin. There is no soil testing so new owners would need to perform tests in order to

Chad Lackey Deerfield Valley Real Estate

0 Elwell Heights Dr, Wilmington, VT 05363
/39
$25,000
- Land
- 0.50 Acre
- $50,000 per Acre
30 Upper Howes Way, Wilmington, VT 05363

Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

Sigrid Pickering Chimney Hill Realty

30 Upper Howes Way, Wilmington, VT 05363
/58
$339,500
- 2 Beds
- 2 Baths
- 1,240 Sq Ft
43 1st Ln Unit 25, Wilmington, VT 05363

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

Donna Brown Skihome Realty

43 1st Ln Unit 25, Wilmington, VT 05363
/14
$305,000
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5 First Ln Unit 1, Wilmington, VT 05363

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

Adam Palmiter Berkley & Veller Greenwood/Dover

5 First Ln Unit 1, Wilmington, 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
/19
$469,000
- 2 Beds
- 2.5 Baths
- 1,399 Sq Ft
15 Haymaker Ln Unit 6D, Wilmington, VT 05363

Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Haymaker Ln Unit 6D, 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
/33
$430,000
- 3 Beds
- 3 Baths
- 2,446 Sq Ft
211 Upper Dam Rd, Wilmington, VT 05363

Charming Saltbox Chalet located in the desirable Chimney Hill community. This classic chalet is just a short drive from Wilmington Village, Lake Whitingham, the Haystack Golf Course, and Mount Snow Ski Resort. The light-filled interior offers a welcoming open concept great room with vaulted ceilings, a wood-burning fireplace with brick hearth, and hardwood flooring. The kitchen features granite

Monique White Deerfield Valley Real Estate

211 Upper Dam Rd, Wilmington, VT 05363
/55
$640,000
- 3 Beds
- 2.5 Baths
- 1,708 Sq Ft
15 Haymaker Ln Unit 6B, Wilmington, VT 05363

A Wonderfully well built and maintained spacious Townhome in Desired Powderhorn Condo Association! Nestled in the heart of Vermont’s breathtaking Green Mountains, this beautifully maintained 3-bedroom, 2.5-bathroom condo is your dream getaway. Located just moments from mountain biking, skiing, snowmobiling including VAST trails. Two minutes from 2 world class golf courses and the stunning

Steve Goldfarb Deerfield Valley Real Estate

15 Haymaker Ln Unit 6B, 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
$459,000
- 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
- 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
/34
$125,000
- Land
- 1.31 Acres
- $95,420 per Acre
118 Chimney Hill Rd, Wilmington, VT 05363

Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

Sigrid Pickering Chimney Hill Realty

118 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
/21
$450,000
- 4 Beds
- 3.5 Baths
- 1,200 Sq Ft
16 Tenth Unit 40, Wilmington, VT 05363

Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in

Adam Palmiter Berkley & Veller Greenwood/Dover

16 Tenth Unit 40, Wilmington, VT 05363
/34
$289,000
- 2 Beds
- 1.5 Baths
- 1,059 Sq Ft
394 Haystack Rd Unit 2, Wilmington, VT 05363

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

Chad Lackey Deerfield Valley Real Estate

394 Haystack Rd Unit 2, 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
/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
/32
$25,000
- Land
- 0.30 Acre
- $83,333 per Acre
139 Big Bend Loop, Wilmington, VT 05363

One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities

Sigrid Pickering Chimney Hill Realty

139 Big Bend Loop, Wilmington, VT 05363
/36
$499,000
- 7 Beds
- 6 Baths
- 2,178 Sq Ft
343 Haystack Rd, Wilmington, VT 05363

This spacious home is located near outdoor recreation spots like 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

Jessica Citera Cummings & Co

343 Haystack Rd, Wilmington, VT 05363

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