54

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
  • 27 Ray Hill Rd, Wilmington, VT 05363
    27 Ray Hill Rd, Wilmington, VT 05363
    27 Ray Hill Rd, Wilmington, VT 05363
    /48

    $510,000

    • 3 Beds
    • 3 Baths
    • 3,420 Sq Ft

    27 Ray Hill Rd, Wilmington, VT 05363

    Located in a desirable setting that offers both privacy and the convenience of walking to the quaint village of downtown Wilmington, this spacious country home is full of potential. The home features a large, light-filled kitchen with plenty of space for cooking and gathering. The original post-and-beam barn, which was moved to the property, has been converted into a generous living and dining

    Monica Sumner BHG Masiello Brattleboro

    27 Ray Hill 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
    /46

    $898,000

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    41 Two Brook Dr, Wilmington, VT 05363

    Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all.Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    41 Two Brook Dr, Wilmington, VT 05363
  • 100 Mowing Way, Wilmington, VT 05363
    100 Mowing Way, Wilmington, VT 05363
    100 Mowing Way, Wilmington, VT 05363
    /31

    $879,000

    • 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
  • 16 Rock Split Way, Wilmington, VT 05363
    16 Rock Split Way, Wilmington, VT 05363
    16 Rock Split Way, Wilmington, VT 05363
    /60

    $749,000

    • 4 Beds
    • 4 Baths
    • 2,964 Sq Ft

    16 Rock Split Way, Wilmington, VT 05363

    Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings,

    Chad Lackey Deerfield Valley Real Estate

    16 Rock Split Way, Wilmington, VT 05363
  • 798 Vermont Route 100, Wilmington, VT 05363
    798 Vermont Route 100, Wilmington, VT 05363
    798 Vermont Route 100, Wilmington, VT 05363
    /41

    $799,000

    • 5 Beds
    • 3 Baths
    • 3,091 Sq Ft

    798 Vermont Route 100, Wilmington, VT 05363

    Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    798 Vermont Route 100, 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
    /30

    $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
  • 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
    • 40,510 Sq Ft
    • $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, hiking,

    Sigrid Pickering Chimney Hill Realty

    564 Upper Dam Rd, Wilmington, VT 05363
  • 33 W Main St, Wilmington, VT 05363
    33 W Main St, Wilmington, VT 05363
    33 W Main St, Wilmington, VT 05363
    /31

    $459,000

    • 1 Bed
    • 2.5 Baths
    • 2,076 Sq Ft

    33 W Main St, Wilmington, VT 05363

    Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33 W Main St, Wilmington, VT 05363
  • 36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    /41

    $2,999,000

    • 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
  • 28 Upper Howes Way, Wilmington, VT 05363
    28 Upper Howes Way, Wilmington, VT 05363
    /2

    $25,000

    • Land
    • 26,136 Sq Ft
    • $41,667 per Acre

    28 Upper Howes Way, Wilmington, VT 05363

    Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

    Sigrid Pickering Chimney Hill Realty

    28 Upper Howes Way, Wilmington, VT 05363
  • 404 Fox Mountain Rd, Wilmington, VT 05363
    404 Fox Mountain Rd, Wilmington, VT 05363
    /2

    $55,000

    • Land
    • 21,780 Sq Ft
    • $110,000 per Acre

    404 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

    Sigrid Pickering Chimney Hill Realty

    404 Fox Mountain Rd, Wilmington, VT 05363
  • 29 Stable Rd, Wilmington, VT 05363
    29 Stable Rd, Wilmington, VT 05363
    /2

    $174,900

    • 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, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. 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
  • 47 Upper Howes Way Unit A-23, Wilmington, VT 05363
    47 Upper Howes Way Unit A-23, Wilmington, VT 05363
    47 Upper Howes Way Unit A-23, Wilmington, VT 05363
    /60

    $479,000

    • 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 Chimney

    Sigrid Pickering Chimney Hill Realty

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363
  • 28 Lightning Ledge Way, Wilmington, VT 05363
    28 Lightning Ledge Way, Wilmington, VT 05363
    28 Lightning Ledge Way, Wilmington, VT 05363
    /23

    $474,900

    • 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
  • 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 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

    $499,990

    • 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

    Colt Hazell 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
  • 197 Lake Raponda Rd, Wilmington, VT 05363
    197 Lake Raponda Rd, Wilmington, VT 05363
    197 Lake Raponda Rd, 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
  • Lot 4 Old Mill Ln, Wilmington, VT 05363
    Lot 4 Old Mill Ln, Wilmington, VT 05363
    Lot 4 Old Mill Ln, Wilmington, VT 05363
    /24

    $774,000

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

    Lot 4 Old Mill Ln, Wilmington, VT 05363

    Desirable Building Lot at Old Mill at Haystack Mountain. House rendering concept has been designed by The Wadsworth Design Build team who are ready to get started on your mountain home. Come discover an 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

    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
  • 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
    • 21,780 Sq Ft
    • $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
  • 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 multi-use

    Janet Boyd Boyd Real Estate

    27 Country Ct, Wilmington, VT 05363
  • 127 Fannie Hill Dr, Wilmington, VT 05363
    127 Fannie Hill Dr, Wilmington, VT 05363
    127 Fannie Hill Dr, Wilmington, VT 05363
    /59

    $2,398,000

    • 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
  • 117 Ray Hill Rd, Wilmington, VT 05363
    117 Ray Hill Rd, Wilmington, VT 05363
    117 Ray Hill Rd, Wilmington, VT 05363
    /15

    $459,000

    • 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, that is 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

    $429,000

    • 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
  • 8 Dorf Auf Radar Rd, Wilmington, VT 05363
    8 Dorf Auf Radar Rd, Wilmington, VT 05363
    8 Dorf Auf Radar Rd, Wilmington, VT 05363
    /5

    $50,000

    • 2 Beds
    • 1 Bath
    • 530 Sq Ft

    8 Dorf Auf Radar Rd, Wilmington, VT 05363

    Delightful, affordable! Be right in the heart of ski country with access to hiking, boating, fishing and biking! This tidy 2 bedroom home has a 10x16 storage shed for your gear! Big enough for a weekend of fun but small enough to keep the costs reasonable. This is better than renting, and always available when you are! This is an exciting find! The property can only be a vacation/second home only.

    Christine Lewis Brattleboro Area Realty

    8 Dorf Auf Radar Rd, Wilmington, VT 05363
  • 68 E Brook Crossing, Wilmington, VT 05363
    68 E Brook Crossing, Wilmington, VT 05363
    68 E Brook Crossing, Wilmington, VT 05363
    /31

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    68 E Brook Crossing, Wilmington, VT 05363

    Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

    Adam Palmiter Berkley & Veller Greenwood/Dover

    68 E Brook Crossing, 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
    /32

    $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
  • 44 Howes Loop, Wilmington, VT 05363
    44 Howes Loop, Wilmington, VT 05363
    44 Howes Loop, Wilmington, VT 05363
    /37

    $399,000

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    44 Howes Loop, Wilmington, VT 05363

    Thoughtfully maintained 4-bedroom, 2-bath Chimney Hill chalet offering a warm, inviting feel with natural wood finishes, open-concept design, woodstove and features that capture the essence of Vermont living. The main living areas are bright, comfortable and welcoming, with easy flow to a deck overlooking surrounding mountain ridgelines—an ideal setting for both quiet mornings and relaxed

    Jacki Murano Southern Vermont Realty Group

    44 Howes Loop, 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

    $437,000

    • 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
  • 26 N Wind Rd, Wilmington, VT 05363
    26 N Wind Rd, Wilmington, VT 05363
    26 N Wind Rd, Wilmington, VT 05363
    /60

    $429,000

    • 3 Beds
    • 3 Baths
    • 2,690 Sq Ft

    26 N Wind Rd, Wilmington, VT 05363

    Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

    Rich Caplan Deerfield Valley Real Estate

    26 N Wind Rd, Wilmington, VT 05363
  • 286 Coldbrook Rd, Wilmington, VT 05363
    286 Coldbrook Rd, Wilmington, VT 05363
    286 Coldbrook Rd, Wilmington, VT 05363
    /16

    $1,400,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,844 Sq Ft

    286 Coldbrook Rd, Wilmington, VT 05363

    This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

    Melissa Nebelski Real Broker LLC

    286 Coldbrook Rd, Wilmington, VT 05363
  • 1 Frog Hollow, Wilmington, VT 05363
    1 Frog Hollow, Wilmington, VT 05363
    1 Frog Hollow, Wilmington, VT 05363
    /55

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1 Frog Hollow, Wilmington, VT 05363

    Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

    Rich Caplan Deerfield Valley Real Estate

    1 Frog Hollow, Wilmington, VT 05363
  • 0 Theresa Ln, Wilmington, VT 05363
    0 Theresa Ln, Wilmington, VT 05363
    0 Theresa Ln, Wilmington, VT 05363
    /20

    $99,500

    • Land
    • 10.27 Acres
    • $9,688 per Acre

    0 Theresa Ln, Wilmington, VT 05363

    This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

    Lisa Mirando Deerfield Valley Real Estate

    0 Theresa Ln, Wilmington, VT 05363
  • 169 Sun and Ski Rd, Wilmington, VT 05363
    169 Sun and Ski Rd, Wilmington, VT 05363
    169 Sun and Ski Rd, Wilmington, VT 05363
    /30

    $89,000

    • Land
    • 1 Acre
    • $89,000 per Acre

    169 Sun and Ski Rd, Wilmington, VT 05363

    Dreaming of building a home in Vermont but not sure where to start? 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

    Kim Meeker Southern Vermont Realty Group

    169 Sun and Ski Rd, Wilmington, VT 05363
  • 216 Ghastly Job Way, Wilmington, VT 05363
    216 Ghastly Job Way, Wilmington, VT 05363
    216 Ghastly Job Way, Wilmington, VT 05363
    /41

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    216 Ghastly Job Way, Wilmington, VT 05363

    Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

    Monique White Deerfield Valley Real Estate

    216 Ghastly Job Way, Wilmington, VT 05363
  • 30 Upper Howes Way, Wilmington, VT 05363
    30 Upper Howes Way, Wilmington, VT 05363
    30 Upper Howes Way, Wilmington, VT 05363
    /39

    $25,000

    • Land
    • 21,780 Sq Ft
    • $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

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 $781,880.
How many homes have sold over the last 12 months in Wilmington, VT?
69 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, 05262, 05356 and 05342.
How much do you need to make to afford a house in Wilmington?
The median home price in Wilmington is $549,000. If you put a 20% down payment of $109,800 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,720 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K 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, Marlboro Elementary School and Twin Valley 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 102 days on the market compared to the national average of 56 days. The median sale price for homes in Wilmington, VT over the last 12 months is $546,000, up 21% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$546,000
Median Single Family Sale Price
$507,500
Median Townhouse Sale Price
$417,500
Median 2 Bedroom Sale Price
$307,000
Average Price Per Sq Ft
$328
Number of Homes for Sale
30
Last 12 months Home Sales
69
Months of Supply
5.20
Median List Price
$549,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
21%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group