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Wilmington, VT Homes for Sale

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  • 16 View Rd, Wilmington, VT 05363
    16 View Rd, Wilmington, VT 05363
    16 View Rd, Wilmington, VT 05363
    /24

    $579,000

    • 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
  • 20 Ray Hill Rd, Wilmington, VT 05363
    20 Ray Hill Rd, Wilmington, VT 05363
    20 Ray Hill 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
  • 5 N Main St, Wilmington, VT 05363
    5 N Main St, Wilmington, VT 05363
    5 N Main St, 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
  • 624 Boyd Hill Rd, Wilmington, VT 05363
    624 Boyd Hill Rd, Wilmington, VT 05363
    624 Boyd Hill Rd, Wilmington, VT 05363
    /28

    $599,000

    • 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
  • 42 View Rd, Wilmington, VT 05363
    42 View Rd, Wilmington, VT 05363
    42 View Rd, Wilmington, VT 05363
    /48

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,484 Sq Ft

    42 View Rd, Wilmington, VT 05363

    Situated in the highly sought-after Chimney Hill Resort community of Wilmington, Vermont, this versatile property offers a unique opportunity for vacation living and rental income. The chalet-inspired main home features an open floor plan with soaring ceilings, an upgraded kitchen with smart home features, and seamless access to a wraparound deck surrounded by mature woods. A detached garage adds

    Nick Sicard EXP Realty

    42 View Rd, Wilmington, VT 05363
  • 12 Conifer Ln, Wilmington, VT 05363
    12 Conifer Ln, Wilmington, VT 05363
    12 Conifer Ln, Wilmington, VT 05363
    /28

    $630,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    12 Conifer Ln, Wilmington, VT 05363

    Welcome to 12 Conifer Lane, your private 3 bedroom 3 bath escape in beautiful Southern Vermont. Built with quality construction and a 5 star energy rating, this home is move-in ready and should provide years of stress free ownership. The feeling inside is comfortable and cozy. Cathedral ceilings in the open concept living and dining room are anchored by the wood burning fireplace, making it a

    Mike Masters Four Seasons Sotheby's Int'l Realty

    12 Conifer Ln, Wilmington, VT 05363
  • 47 Ives Rd, Wilmington, VT 05363
    47 Ives Rd, Wilmington, VT 05363
    47 Ives 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
  • 19 Village Rd E, Wilmington, VT 05363
    19 Village Rd E, Wilmington, VT 05363
    19 Village Rd E, Wilmington, VT 05363
    /27

    $895,000

    • 4 Beds
    • 3 Baths
    • 2,546 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
  • 37 Pleasant View Ln, Wilmington, VT 05363
    37 Pleasant View Ln, Wilmington, VT 05363
    37 Pleasant View Ln, Wilmington, VT 05363
    /42

    $875,000

    • 4 Beds
    • 3.5 Baths
    • 3,553 Sq Ft

    37 Pleasant View Ln, Wilmington, VT 05363

    Seeking an upscale but also rustic, Vermont retreat? Looking for privacy but convenience to amenities? Love a water feature and a mountain view? Need a place to host large gatherings but also cozy enough for a romantic weekend getaway? This is just the place. Tucked away on a private road sits this spacious 4 bedroom, 3.5 bath, true log home with an excellent layout over 3 finished floors. All

    Jacki Murano Southern Vermont Realty Group

    37 Pleasant View Ln, Wilmington, VT 05363
  • 67 Castle Hill Rd, Wilmington, VT 05363
    67 Castle Hill Rd, Wilmington, VT 05363
    67 Castle Hill Rd, Wilmington, VT 05363
    /40

    $895,000

    • 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
  • 111 Binney Brook Rd Unit M581, Wilmington, VT 05363
    111 Binney Brook Rd Unit M581, Wilmington, VT 05363
    111 Binney Brook Rd Unit M581, Wilmington, VT 05363
    /60

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363

    Nice location on the Hill! Featuring a fairly level lot, seasonal views from the deck, a vaulted ceiling in the living room, along with a wood-burning fireplace and adjacent dining area, which is next to the kitchen. Never rented, original wood paneling and detailing are intact, a compact galley kitchen, shower bath and two bedrooms on the main upstairs level. the lower walkout level has a

    Sigrid Pickering Chimney Hill Realty

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363
  • 26 Lisle Hill Rd, Wilmington, VT 05363
    26 Lisle Hill Rd, Wilmington, VT 05363
    26 Lisle Hill Rd, Wilmington, VT 05363
    /27

    $439,000

    • 5 Beds
    • 4 Baths
    • 2,770 Sq Ft

    26 Lisle Hill Rd, Wilmington, VT 05363

    Lovely updated home just up from the village of Wilmington and with mountain views and gorgeous exposure. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access into downtown. The home sits on a functional lot with ample parking and privacy despite the small size, lovely trees and stone walls. Public sewer and water

    Adam Palmiter Berkley & Veller Greenwood/Dover

    26 Lisle Hill Rd, Wilmington, VT 05363
  • 30 Big Bend Loop, Wilmington, VT 05363
    30 Big Bend Loop, Wilmington, VT 05363
    30 Big Bend Loop, Wilmington, VT 05363
    /58

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,500 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
  • 178 Parsons Rd, Wilmington, VT 05363
    178 Parsons Rd, Wilmington, VT 05363
    178 Parsons Rd, Wilmington, VT 05363
    /29

    $299,000

    • 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
  • 121 Happy Haven Rd, Wilmington, VT 05363
    121 Happy Haven Rd, Wilmington, VT 05363
    121 Happy Haven Rd, Wilmington, VT 05363
    /43

    $295,000

    • 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
  • 290 Old Mill Ln, Wilmington, VT 05363
    290 Old Mill Ln, Wilmington, VT 05363
    290 Old Mill Ln, Wilmington, VT 05363
    /33

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    290 Old Mill Ln, Wilmington, VT 05363

    “The Camp” Are you looking for that special seasonal getaway? Look no further! This charming 1-bedroom on the main level and second bedroom upstairs sleeping loft is located in the beautiful town of Wilmington. Nestled in the woods, this cozy cabin offers a unique and special Vermont experience. Enjoy the covered front porch and large deck, perfect for entertaining friends and family. Just steps

    Richard Caplan Deerfield Valley Real Estate

    290 Old Mill Ln, Wilmington, VT 05363
  • 0 Big Bend Loop Unit 5039354, Wilmington, VT 05363
    0 Big Bend Loop Unit 5039354, Wilmington, VT 05363
    0 Big Bend Loop Unit 5039354, Wilmington, VT 05363
    /32

    $25,000

    • Land
    • 1.00 Acre
    • $25,000 per Acre

    0 Big Bend Loop Unit 5039354, 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 Chimney

    Sigrid Pickering Chimney Hill Realty

    0 Big Bend Loop Unit 5039354, Wilmington, VT 05363
  • 343 Haystack Rd, Wilmington, VT 05363
    343 Haystack Rd, Wilmington, VT 05363
    343 Haystack Rd, Wilmington, VT 05363
    /39

    $529,000

    • 7 Beds
    • 6 Baths
    • 2,978 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
  • 410 Fox Mountain Rd, Wilmington, VT 05363
    410 Fox Mountain Rd, Wilmington, VT 05363
    410 Fox Mountain Rd, Wilmington, VT 05363
    /40

    $85,000

    • Land
    • 1.03 Acres
    • $82,524 per Acre

    410 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 Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

    Sigrid Pickering Chimney Hill Realty

    410 Fox Mountain Rd, Wilmington, VT 05363
  • 408 Fox Mountain Rd, Wilmington, VT 05363
    408 Fox Mountain Rd, Wilmington, VT 05363
    408 Fox Mountain Rd, Wilmington, VT 05363
    /40

    $125,000

    • Land
    • 1.58 Acres
    • $79,114 per Acre

    408 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 Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

    Sigrid Pickering Chimney Hill Realty

    408 Fox Mountain Rd, 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
  • 402 Fox Mountain Rd, Wilmington, VT 05363
    402 Fox Mountain Rd, Wilmington, VT 05363
    402 Fox Mountain Rd, Wilmington, VT 05363
    /33

    $85,000

    • Land
    • 1.04 Acres
    • $81,731 per Acre

    402 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

    Sigrid Pickering Chimney Hill Realty

    402 Fox Mountain Rd, Wilmington, VT 05363
  • 0 Spruce Grove Rd Unit 5035135, Wilmington, VT 05363
    0 Spruce Grove Rd Unit 5035135, Wilmington, VT 05363
    0 Spruce Grove Rd Unit 5035135, Wilmington, VT 05363
    /14

    $369,000

    • Land
    • 8 Acres
    • $45,556 per Acre

    0 Spruce Grove Rd Unit 5035135, Wilmington, VT 05363

    Escape to your own private sanctuary on 8.1 acres of pristine land with stunning mountain views. This exceptional property is free from HOA restrictions, offering unlimited potential for your dream home or retreat. Featuring a cleared building site, new driveway, and a State of VT Wastewater Permit for a 4-bedroom dwelling, everything is in place for your vision. Accessible off a public road with

    Chad Lackey Deerfield Valley Real Estate

    0 Spruce Grove Rd Unit 5035135, 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

    $74,900

    • Land
    • 3.58 Acres
    • $20,922 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 158/160 High Peak Way, Wilmington, VT 05363
    LOT 158/160 High Peak Way, Wilmington, VT 05363
    LOT 158/160 High Peak Way, Wilmington, VT 05363
    /5

    $125,000

    • Land
    • 0.43 Acre
    • $290,698 per Acre

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

    Sun filled level Double lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    LOT 158/160 High Peak Way, Wilmington, VT 05363
  • Lot 162 High Peak Way, Wilmington, VT 05363
    Lot 162 High Peak Way, Wilmington, VT 05363
    Lot 162 High Peak Way, Wilmington, VT 05363
    /4

    $99,000

    • Land
    • 0.32 Acre
    • $309,375 per Acre

    Lot 162 High Peak Way, Wilmington, VT 05363

    Sun filled level corner lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    Lot 162 High Peak Way, Wilmington, VT 05363
  • 115 E Village Cir, Wilmington, VT 05363
    115 E Village Cir, Wilmington, VT 05363
    115 E Village Cir, Wilmington, VT 05363
    /51

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,203 Sq Ft

    115 E Village Cir, Wilmington, VT 05363

    This stunning 4 bedroom, 4 bath home is located just across the road from the Hermitage Club and 4 miles to Mount Snow. Entryway is set up to welcome everyone into this lovely home, with ample room for outdoor clothing. Next step into a beautiful kitchen and dining area featuring high-end kitchen appliances and a comfortable dining area. The first floor also has a living room, sitting area,

    Tony Tribuno Skihome Realty

    115 E Village Cir, 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
    /17

    $749,000

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

    Lot 3 Old Mill Ln, Wilmington, VT 05363

    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 the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 Old Mill Ln, 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
    /23

    $749,000

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

    Lot 2 Old Mill Ln, Wilmington, VT 05363

    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 the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 2 Old Mill Ln, Wilmington, VT 05363
  • Lot 5 Old Mill Ln, Wilmington, VT 05363
    Lot 5 Old Mill Ln, Wilmington, VT 05363
    Lot 5 Old Mill Ln, Wilmington, VT 05363
    /20

    $774,000

    • Land
    • 3.60 Acres
    • $215,000 per Acre

    Lot 5 Old Mill Ln, Wilmington, VT 05363

    Discover an exceptional opportunity to own a 3.6 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 the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 5 Old Mill Ln, Wilmington, VT 05363
  • 27 Haymaker Ln Unit 9H, Wilmington, VT 05363
    27 Haymaker Ln Unit 9H, Wilmington, VT 05363
    27 Haymaker Ln Unit 9H, Wilmington, VT 05363
    /34

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,127 Sq Ft

    27 Haymaker Ln Unit 9H, Wilmington, VT 05363

    Cozy convenience on Haystack Mountain adjacent to The Hermitage Club and just a short drive to Mount Snow and downtown Wilmington. This 2 bedroom/2 bathroom unit has an open living space perfect for entertaining and highlighted by the fieldstone fireplace ambiance to warm you apres ski/hike or snowshoe. The unit is being offered furnished and ready to enjoy this season and year round with access

    Cordelia Garofalo Deerfield Valley Real Estate

    27 Haymaker Ln Unit 9H, Wilmington, VT 05363
  • 100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363
    100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363
    100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363
    /36

    $85,000

    • Land
    • 1.31 Acres
    • $64,885 per Acre

    100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363

    Merged Triple Lot on 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. Located about 1/2 way up the Hill, right off the pavement. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis,

    Sigrid Pickering Chimney Hill Realty

    100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363
  • 95 Chimney Hill Rd Unit M95, Wilmington, VT 05363
    95 Chimney Hill Rd Unit M95, Wilmington, VT 05363
    95 Chimney Hill Rd Unit M95, Wilmington, VT 05363
    /38

    $85,000

    • Land
    • 1.09 Acres
    • $77,982 per Acre

    95 Chimney Hill Rd Unit M95, Wilmington, VT 05363

    Triple Merged Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! Right off the pavement about halfway up the Hill on the plateau. If you've been thinking of building your Dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season

    Sigrid Pickering Chimney Hill Realty

    95 Chimney Hill Rd Unit M95, Wilmington, VT 05363
  • 53 N Main St, Wilmington, VT 05363
    53 N Main St, Wilmington, VT 05363
    53 N Main St, Wilmington, VT 05363
    /11

    $639,000

    • 5 Beds
    • 3 Baths
    • 5,424 Sq Ft

    53 N Main St, Wilmington, VT 05363

    Formerly listed in the Wilmington Town Records as a Commercial Property, however, the owners changed that designation to Residential including a one bed./one bath apartment and (2) two bedroom, one bath apartments and a 7 bedroom/7.5 half bath once an Inn. The current owner is in the process of installing egress windows in all bedrooms in the Inn. The current owner has also electrified all smoke

    Ginny Read Read Realty LTD

    53 N Main St, Wilmington, VT 05363
  • 0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363
    0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363
    0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363
    /30

    $50,000

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

    0 Upper Dam Rd Unit 5019848, 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

    0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363
  • 0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363
    0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363
    0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363
    /37

    $50,000

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

    0 Upper Dam Rd Unit 5019824, 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

    0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363
  • 0 2 Wall Way Unit 5019786, Wilmington, VT 05363
    0 2 Wall Way Unit 5019786, Wilmington, VT 05363
    0 2 Wall Way Unit 5019786, Wilmington, VT 05363
    /30

    $25,000

    • Land
    • 0.53 Acre
    • $47,170 per Acre

    0 2 Wall Way Unit 5019786, Wilmington, VT 05363

    Single Lot on top of the Hill! Walk to the clubhouse from your very own vacation home, designed by you. Survey required and septic design. Lot is unimproved but has had recent favorable soil tests. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking, biking, snowmobiling, and more on our 1,200-acre

    Sigrid Pickering Chimney Hill Realty

    0 2 Wall Way Unit 5019786, Wilmington, VT 05363
  • 43 1st Ln Unit 28, Wilmington, VT 05363
    43 1st Ln Unit 28, Wilmington, VT 05363
    43 1st Ln Unit 28, Wilmington, VT 05363
    /21

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    43 1st Ln Unit 28, Wilmington, VT 05363

    Beautiful updated condo overlooking the 1st green at the Haystack Golf Club, as well as the mountains and sunsets beyond. This lovely private unit sits right on one of the best courses in New England, and is a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. The interior features a large open living space with vaulted ceilings, updated vinyl

    Adam Palmiter Berkley & Veller Greenwood/Dover

    43 1st Ln Unit 28, Wilmington, VT 05363
  • 0 Upper Howes Way Unit 5008127, Wilmington, VT 05363
    0 Upper Howes Way Unit 5008127, Wilmington, VT 05363
    0 Upper Howes Way Unit 5008127, Wilmington, VT 05363
    /29

    $25,000

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

    0 Upper Howes Way Unit 5008127, Wilmington, VT 05363

    BUILD your dream home in this Lot 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 200'

    Sigrid Pickering Chimney Hill Realty

    0 Upper Howes Way Unit 5008127, Wilmington, VT 05363
  • 0 Upper Howes Way Unit 5008126, Wilmington, VT 05363
    0 Upper Howes Way Unit 5008126, Wilmington, VT 05363
    0 Upper Howes Way Unit 5008126, Wilmington, VT 05363
    /32

    $25,000

    • Land
    • 0.56 Acre
    • $44,643 per Acre

    0 Upper Howes Way Unit 5008126, Wilmington, VT 05363

    BUILD your Getaway 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 200' with fitness,

    Sigrid Pickering Chimney Hill Realty

    0 Upper Howes Way Unit 5008126, Wilmington, VT 05363

Showing Results 1 - 40, Page 1 of 2

Vermont Wilmington

Real Estate & Homes for Sale in Wilmington, VT

Why Live in Wilmington

A small resort town in Southern Vermont, Wilmington has scenic mountain trails, recreational lakes and a historic downtown district. Home to slightly more than 2,000 full-time residents, this Windham County area is predominantly a second-home community. But those whose primary residence is somewhere else are still very involved with the local community. “The second-homeowner population really sees this as their home away from home, which you don’t see in other resort areas,” says Patrice Schneider, a local Realtor with Southern Vermont Realty G ...

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 $722,005.
How many homes have sold over the last 12 months in Wilmington, VT?
78 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 01247, 05356, 05301, 05201 and 01267.
How much do you need to make to afford a house in Wilmington?
The median home price in Wilmington is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $2,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Wilmington.
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, Twin Valley 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 89 days on the market compared to the national average of 49 days. The median sale price for homes in Wilmington, VT over the last 12 months is $458,825, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$458,825
Median Single Family Sale Price
$465,000
Median Townhouse Sale Price
$520,000
Median 2 Bedroom Sale Price
$344,725
Average Price Per Sq Ft
$288
Number of Homes for Sale
19
Last 12 months Home Sales
78
Months of Supply
2.90
Median List Price
$525,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
2%
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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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