17

Wilmington, VT Houses for Sale

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  • /35

    $795,000

    • 4 Beds
    • 5 Baths
    • 3,129 Sq Ft

    20 Ray Hill Rd, Wilmington, VT 05363

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

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Ray Hill Rd, Wilmington, VT 05363
  • /41

    $725,000

    • 3 Beds
    • 3.5 Baths
    • 4,219 Sq Ft

    5 N Main St, Wilmington, VT 05363

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

    Morriah Adams BHG Masiello Brattleboro

    5 N Main St, Wilmington, VT 05363
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /40

    $3,450,000

    • 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
  • /52

    $329,000

    • 3 Beds
    • 2 Baths
    • 1,239 Sq Ft

    3185 Higley Hill Rd, Guilford, VT 05301

    Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept main

    Chad Lackey Deerfield Valley Real Estate

    3185 Higley Hill Rd, Guilford, VT 05301

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 ...

Home Trends in Wilmington, VT

Housing Trends

Median Sale Price
$457,650
Median Single Family Sale Price
$460,000
Median Townhouse Sale Price
$520,000
Median 2 Bedroom Sale Price
$344,725
Average Price Per Sq Ft
$284
Number of Homes for Sale
16
Last 12 months Home Sales
79
Months of Supply
2.40
Median List Price
$515,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
1%
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