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Wilmington, VT Homes for Sale

Section Image
  • Higley Hill Rd, Wilmington, VT 05363
    Higley Hill Rd, Wilmington, VT 05363
    Higley Hill Rd, Wilmington, VT 05363
    /12

    $999,000

    • Land
    • 12.2 Acres
    • $81,885 per Acre

    Higley Hill Rd, Wilmington, VT 05363

    Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

    Community Lands Community Lands

    Higley Hill Rd, Wilmington, VT 05363
  • 12 Lilla Ln, Wilmington, VT 05363
    12 Lilla Ln, Wilmington, VT 05363
    12 Lilla Ln, Wilmington, VT 05363
    /21

    $489,000

    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    12 Lilla Ln, Wilmington, VT 05363

    Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Lilla Ln, Wilmington, VT 05363
  • Lot 3 Old Mill Ln, Wilmington, VT 05363
    Lot 3 Old Mill Ln, Wilmington, VT 05363
    Lot 3 Old Mill Ln, Wilmington, VT 05363
    /24

    $749,000

    • Land
    • 2.57 Acres
    • $291,440 per Acre

    Lot 3 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 Old Mill Ln, Wilmington, VT 05363
  • 406 Fox Mountain Rd, Wilmington, VT 05363
    406 Fox Mountain Rd, Wilmington, VT 05363
    406 Fox Mountain Rd, Wilmington, VT 05363
    /35

    $125,000

    • Land
    • 1.52 Acres
    • $82,237 per Acre

    406 Fox Mountain Rd, Wilmington, VT 05363

    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!

    Sigrid Pickering Chimney Hill Realty

    406 Fox Mountain Rd, Wilmington, VT 05363
  • 6 Gates Lake Raponda Ln, Wilmington, VT 05363
    6 Gates Lake Raponda Ln, Wilmington, VT 05363
    6 Gates Lake Raponda Ln, Wilmington, VT 05363
    /30

    $449,000

    • 2 Beds
    • 1.5 Baths
    • 1,416 Sq Ft

    6 Gates Lake Raponda 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 Lake Raponda Ln, Wilmington, VT 05363
  • 564 Upper Dam Rd, Wilmington, VT 05363
    564 Upper Dam Rd, Wilmington, VT 05363
    564 Upper Dam Rd, Wilmington, VT 05363
    /37

    $50,000

    • Land
    • 0.93 Acre
    • $53,763 per Acre

    564 Upper Dam Rd, Wilmington, VT 05363

    Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing,

    Sigrid Pickering Chimney Hill Realty

    564 Upper Dam Rd, Wilmington, VT 05363
  • 339 Coldbrook Rd, Wilmington, VT 05363
    339 Coldbrook Rd, Wilmington, VT 05363
    339 Coldbrook Rd, Wilmington, VT 05363
    /54

    $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
  • 96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
    96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
    96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
    /60

    $415,000

    • 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
  • 36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    /40

    $3,050,000

    • 6 Beds
    • 3 Baths
    • 3,309 Sq Ft

    36 Woffenden Rd, Wilmington, VT 05363

    Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • 145 Shearer Hill Rd, Wilmington, VT 05363
    145 Shearer Hill Rd, Wilmington, VT 05363
    145 Shearer Hill Rd, Wilmington, VT 05363
    /21

    $725,000

    • 5 Beds
    • 3.5 Baths
    • 2,696 Sq Ft

    145 Shearer Hill Rd, Wilmington, VT 05363

    Beautiful 2010 post and beam home just a short drive from the Mount Snow Ski Resort and village of Wilmington. This meticulous turn key home was built with quality in mind, is very energy efficient and sits on a on a private 5+ acre parcel abutting a stream just up from Spruce Lake. Inside is a gorgeous great room space with vaulted ceilings and exposed natural woodwork, great natural light

    Adam Palmiter Berkley & Veller Greenwood/Dover

    145 Shearer Hill Rd, Wilmington, VT 05363
  • 29 Stable Rd, Wilmington, VT 05363
    29 Stable Rd, Wilmington, VT 05363
    /2

    $199,000

    • 2 Beds
    • 2,710 Sq Ft

    29 Stable Rd, Wilmington, VT 05363

    The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

    Mark Yule BHG Masiello Brattleboro

    29 Stable Rd, Wilmington, VT 05363
  • 46 Town Farm Rd, Wilmington, VT 05363
    46 Town Farm Rd, Wilmington, VT 05363
    46 Town Farm Rd, Wilmington, VT 05363
    /17

    $459,000

    • 5 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    46 Town Farm Rd, Wilmington, VT 05363

    3 Story home with 1 car attached garage....new vinyl siding, windows and roofing installed in 2021 along with exterior foamboard insulation.FIRST FLOOR- Open concept entirely remodeled in 2022; mudroom, kitchen, 1/2 bath, and family/dining room. Vinyl plank flooring throughout, white shiplap walls and natural tongue & groove ceilings. Vermont castings wood burning stove.SECOND

    David White OwnerEntry.com

    46 Town Farm Rd, Wilmington, VT 05363
  • 121 Fannie Hill Dr, Wilmington, VT 05363
    121 Fannie Hill Dr, Wilmington, VT 05363
    121 Fannie Hill Dr, 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
  • 11 Dutchman Ln Unit 4A, Wilmington, VT 05363
    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
    /36

    $529,000

    • 3 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • Lot 4 Ghastly Job Way, Wilmington, VT 05363
    Lot 4 Ghastly Job Way, Wilmington, VT 05363
    Lot 4 Ghastly Job Way, Wilmington, VT 05363
    /15

    $69,000

    • Land
    • 3.58 Acres
    • $19,274 per Acre

    Lot 4 Ghastly Job Way, Wilmington, VT 05363

    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

    Monique White Deerfield Valley Real Estate

    Lot 4 Ghastly Job Way, Wilmington, VT 05363
  • Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
    /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • 555 Vermont 9, Wilmington, VT 05363
    555 Vermont 9, Wilmington, VT 05363
    555 Vermont 9, Wilmington, VT 05363
    /42

    $559,990

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    555 Vermont 9, Wilmington, VT 05363

    MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

    Flex Realty Group Flex Realty

    555 Vermont 9, Wilmington, VT 05363
  • 8 Little Bend Unit M-175, Wilmington, VT 05363
    8 Little Bend Unit M-175, Wilmington, VT 05363
    8 Little Bend Unit M-175, Wilmington, VT 05363
    /60

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    8 Little Bend Unit M-175, Wilmington, VT 05363

    Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

    Sigrid Pickering Chimney Hill Realty

    8 Little Bend Unit M-175, Wilmington, VT 05363
  • 47 Ives Rd, Wilmington, VT 05363
    47 Ives Rd, Wilmington, VT 05363
    47 Ives Rd, Wilmington, VT 05363
    /28

    $499,000

    • 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
  • 101 North Rd, Wilmington, VT 05363
    101 North Rd, Wilmington, VT 05363
    101 North Rd, Wilmington, VT 05363
    /39

    $849,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,020 Sq Ft

    101 North Rd, Wilmington, VT 05363

    Stunning new construction in the Chimney Hill community just outside the village of Wilmington, and a short drive to both the Mount Snow ski resort, Hermitage Club, and Lake Whitingham. Located on an easily accessible corner lot in the desirable B section at the bottom of the hill with unique double lot size allowing for tremendous expansion potential . This home was built sparing no expense and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    101 North Rd, Wilmington, VT 05363
  • 100 Mowing Way, Wilmington, VT 05363
    100 Mowing Way, Wilmington, VT 05363
    100 Mowing Way, 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
  • 14 Tarheel Trail, Wilmington, VT 05363
    14 Tarheel Trail, Wilmington, VT 05363
    14 Tarheel Trail, Wilmington, VT 05363
    /35

    $2,197,000

    • 5 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    14 Tarheel Trail, Wilmington, VT 05363

    This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14 Tarheel Trail, Wilmington, VT 05363
  • Lot 4 Old Mill Ln, Wilmington, VT 05363
    Lot 4 Old Mill Ln, Wilmington, VT 05363
    Lot 4 Old Mill Ln, Wilmington, VT 05363
    /25

    $774,000

    • Land
    • 1.32 Acres
    • $586,364 per Acre

    Lot 4 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 1.3 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium cleared lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 4 Old Mill Ln, Wilmington, VT 05363
  • 195 Mann Rd Unit 12, Wilmington, VT 05363
    195 Mann Rd Unit 12, Wilmington, VT 05363
    195 Mann Rd Unit 12, Wilmington, VT 05363
    /52

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,814 Sq Ft

    195 Mann Rd Unit 12, Wilmington, VT 05363

    Beautifully positioned along the 11th fairway of the Haystack Golf Course, this contemporary 3-bedroom, 4-bath townhouse offers four-season comfort with gorgeous mountain and sunrise views. The bright main level features an open layout with vaulted ceilings, a wood-burning fireplace, contemporary kitchen with breakfast bar, and a spacious dining area overlooking the outdoors. The primary suite is

    Donald Koelsch Deerfield Valley Real Estate

    195 Mann Rd Unit 12, Wilmington, VT 05363
  • 49 West Rd, Wilmington, VT 05363
    49 West Rd, Wilmington, VT 05363
    49 West Rd, Wilmington, VT 05363
    /28

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    49 West Rd, Wilmington, VT 05363

    Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 West Rd, Wilmington, VT 05363
  • LOT 3 158/160 High Peak Way, Wilmington, VT 05363
    LOT 3 158/160 High Peak Way, Wilmington, VT 05363
    LOT 3 158/160 High Peak Way, Wilmington, VT 05363
    /20

    $90,100

    • Land
    • 0.5 Acre
    • $180,200 per Acre

    LOT 3 158/160 High Peak Way, Wilmington, VT 05363

    A opportunity to own this .50-acre double lot in the High Peak Development, offering a double lot for your Vermont getaway. Ideally situated adjacent to the Haystack Golf Course, this parcel provides the perfect mountain convenience. Just a short drive to Mount Snow**, The Hermitage Club, and all the year-round recreation the Deerfield Valley is known for, this property also offers direct access

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    LOT 3 158/160 High Peak Way, Wilmington, VT 05363
  • 12 Three Streams Way, Wilmington, VT 05363
    12 Three Streams Way, Wilmington, VT 05363
    12 Three Streams Way, Wilmington, VT 05363
    /32

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,216 Sq Ft

    12 Three Streams Way, Wilmington, VT 05363

    Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Three Streams Way, Wilmington, VT 05363
  • 28 Upper Howes Way, Wilmington, VT 05363
    28 Upper Howes Way, Wilmington, VT 05363
    28 Upper Howes Way, Wilmington, VT 05363
    /28

    $25,000

    • Land
    • 0.6 Acre
    • $41,667 per Acre

    28 Upper Howes Way, Wilmington, VT 05363

    BUILD your dream home in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at

    Sigrid Pickering Chimney Hill Realty

    28 Upper Howes Way, Wilmington, VT 05363
  • 566 Upper Dam Rd, Wilmington, VT 05363
    566 Upper Dam Rd, Wilmington, VT 05363
    566 Upper Dam Rd, Wilmington, VT 05363
    /30

    $50,000

    • Land
    • 0.93 Acre
    • $53,763 per Acre

    566 Upper Dam Rd, Wilmington, VT 05363

    Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your getaway home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking,

    Sigrid Pickering Chimney Hill Realty

    566 Upper Dam Rd, Wilmington, VT 05363
  • 15 Haymaker Ln Unit 6D, Wilmington, VT 05363
    15 Haymaker Ln Unit 6D, Wilmington, VT 05363
    15 Haymaker Ln Unit 6D, Wilmington, VT 05363
    /19

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,912 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
  • 27 Country Ct, Wilmington, VT 05363
    27 Country Ct, Wilmington, VT 05363
    27 Country Ct, Wilmington, VT 05363
    /50

    $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
  • 8 Happy Haven Rd, Wilmington, VT 05363
    8 Happy Haven Rd, Wilmington, VT 05363
    8 Happy Haven Rd, Wilmington, VT 05363
    /14

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    8 Happy Haven Rd, Wilmington, VT 05363

    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

    Janet Boyd Boyd Real Estate

    8 Happy Haven Rd, Wilmington, VT 05363
  • 127 Fannie Hill Dr, Wilmington, VT 05363
    127 Fannie Hill Dr, Wilmington, VT 05363
    127 Fannie Hill Dr, 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
  • 5 First Ln Unit 1, Wilmington, VT 05363
    5 First Ln Unit 1, Wilmington, VT 05363
    5 First Ln Unit 1, 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
  • 117 Ray Hill Rd, Wilmington, VT 05363
    117 Ray Hill Rd, Wilmington, VT 05363
    117 Ray Hill Rd, Wilmington, VT 05363
    /15

    $529,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    117 Ray Hill Rd, Wilmington, VT 05363

    This wonderful home boast 10.5 +/- acres, plenty of room for gardening, a pond and is only moments to the village center! Beautiful hard wood floors throughout, Livingroom with gas fireplace a a beautiful view, dining area and kitchen, 3 bedrooms, 2 bathrooms, 2 decks and a simple 1 car garage. The lower level boasts a walk- out, is completely dry and waiting to be finished!

    Janet Boyd Boyd Real Estate

    117 Ray Hill Rd, Wilmington, VT 05363
  • 156 Mountain View Rd, Wilmington, VT 05363
    156 Mountain View Rd, Wilmington, VT 05363
    156 Mountain View Rd, Wilmington, VT 05363
    /39

    $489,000

    • 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
  • Lot 2 Old Mill Ln, Wilmington, VT 05363
    Lot 2 Old Mill Ln, Wilmington, VT 05363
    Lot 2 Old Mill Ln, Wilmington, VT 05363
    /26

    $749,000

    • Land
    • 1.22 Acres
    • $613,934 per Acre

    Lot 2 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 1.22-acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 2 Old Mill Ln, Wilmington, VT 05363
  • 29 First Unit 17, Wilmington, VT 05363
    29 First Unit 17, Wilmington, VT 05363
    29 First Unit 17, Wilmington, VT 05363
    /45

    $449,000

    • 4 Beds
    • 3.5 Baths
    • 2,015 Sq Ft

    29 First Unit 17, Wilmington, VT 05363

    Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning

    Monique White Deerfield Valley Real Estate

    29 First Unit 17, Wilmington, VT 05363
  • 18 New England Power Rd, Wilmington, VT 05363
    18 New England Power Rd, Wilmington, VT 05363
    18 New England Power Rd, Wilmington, VT 05363
    /60

    $2,150,000

    • 5 Beds
    • 5 Baths
    • 5,500 Sq Ft

    18 New England Power Rd, Wilmington, VT 05363

    This extraordinary luxury farmhouse has been masterfully remodeled by the current owners, offering a refined retreat abutting Vermont’s Green Mountain Forest. Every inch has been reimagined with high-end finishes, from the new roof to custom details throughout, creating a turnkey sanctuary that blends timeless charm with modern sophistication. A beautiful sunroom invites relaxation with abundant

    Samantha Decker Deerfield Valley Real Estate

    18 New England Power Rd, Wilmington, VT 05363
  • 41 Two Brook Dr, Wilmington, VT 05363
    41 Two Brook Dr, Wilmington, VT 05363
    41 Two Brook Dr, Wilmington, VT 05363
    /35

    $939,000

    • 4 Beds
    • 5 Baths
    • 3,420 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

Showing Results 1 - 40, Page 1 of 2

Vermont Windham County Wilmington

Real Estate & Homes for Sale in Wilmington, VT

Why Live in Wilmington

Wilmington, Vermont, a small resort town in Southern Vermont, offers a blend of scenic mountain trails, recreational lakes, and a historic downtown district. With a population of just over 2,000 full-time residents, it is predominantly a second-home community where even non-primary residents are actively involved. The town's landscape features several hiking trails, including the 4-mile Mount Haystack Trail and the 14-mile Valley Trail. Wilmington's lakes, such as Lake Whitingham and Lake Raponda, provide opportunities for swimming, boating, and winter ice fishing. The Hermitage Club, a private ski resort, and the public Mount Snow Resort in nearby Dover offer year-round recreational activities. Wilmington's historic downtown, listed on the National Register of Historic Places, showcases 59 Georgian-style buildings now housing museums, boutiques, and eateries. The residential area includes a mix of cozy cottages, sprawling chalets, Mountain Modern timber frame homes, and historical farmhouses. Wilmington's downtown features local cafes, eateries, pubs, and shops, with highlights like Dot’s diner, The Anchor, and Wilmington Village Pub. Annual events such as the Vermont Wine & Harvest Festival and the Vermont Craft Beer & Chili Stroll draw crowds to the area. Students can attend the highly rated Twin Valley Elementary School and later advance to Twin Valley Middle High School. Wilmington’s crime rate is generally lower than both the state and national averages. The town is car-dependent, with Vermont Route 100 and Vermont Route 9 connecting residents to larger New England cities and international airports.

Learn more about living in Wilmington

Frequently Asked Questions

What is the average home price in Wilmington, VT?
Homes for sale in Wilmington, VT have an average home price of $810,368.
How many homes have sold over the last 12 months in Wilmington, VT?
70 homes have sold in Wilmington, VT over the last 12 months.
What are the most popular zip codes in Wilmington, VT?
The most popular zip codes in Wilmington, VT include 05363, 05301, 05356, 05342 and 05361.
How much do you need to make to afford a house in Wilmington?
The median home price in Wilmington is $549,500. If you put a 20% down payment of $109,900 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $2,700 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K a year to afford the median home price in Wilmington. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Wilmington, VT?
Wilmington, VT has highly rated public and private schools. Some of the best schools in Wilmington based on Niche Grades are Dover Elementary School, Readsboro Elementary School and Marlboro Elementary School. Browse all the schools in Wilmington, VT to learn more.

Home Trends in Wilmington, VT

On average, homes in Wilmington, VT sell after 95 days on the market compared to the national average of 53 days. The median sale price for homes in Wilmington, VT over the last 12 months is $502,500, up 26% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$502,500
Median Single Family Sale Price
$505,000
Median Townhouse Sale Price
$449,500
Median 2 Bedroom Sale Price
$375,000
Average Price Per Sq Ft
$323
Number of Homes for Sale
46
Last 12 months Home Sales
70
Months of Supply
7.90
Median List Price
$549,500
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
26%
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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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