72

Wilmington, VT Homes for Sale

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

    $99,000

    $900K PRICE DROP
    • Land
    • 12.2 Acres
    • $8,115 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
  • 7 High Top Unit B117, Wilmington, VT 05363
    7 High Top Unit B117, Wilmington, VT 05363
    7 High Top Unit B117, Wilmington, VT 05363
    /42

    $489,999

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

    7 High Top Unit B117, Wilmington, VT 05363

    Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and

    Sigrid Pickering Chimney Hill Realty

    7 High Top Unit B117, 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
    /23

    $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
  • 392 Lake Raponda Rd, Wilmington, VT 05363
    392 Lake Raponda Rd, Wilmington, VT 05363
    392 Lake Raponda Rd, Wilmington, VT 05363
    /39

    $2,195,000

    • 4 Beds
    • 4 Baths
    • 3,524 Sq Ft

    392 Lake Raponda Rd, Wilmington, VT 05363

    A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake — with a private dock — just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats

    Adam Palmiter Berkley & Veller Greenwood/Dover

    392 Lake Raponda 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
    /33

    $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
  • 37 Stowe Hill Rd, Wilmington, VT 05363
    37 Stowe Hill Rd, Wilmington, VT 05363
    37 Stowe Hill Rd, Wilmington, VT 05363
    /57

    $624,900

    • 4 Beds
    • 2.5 Baths
    • 2,904 Sq Ft

    37 Stowe Hill Rd, Wilmington, VT 05363

    Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm.

    Monique White Deerfield Valley Real Estate

    37 Stowe Hill Rd, Wilmington, VT 05363
  • 5 Camelot Dr, Wilmington, VT 05363
    5 Camelot Dr, Wilmington, VT 05363
    5 Camelot Dr, Wilmington, VT 05363
    /47

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    5 Camelot Dr, Wilmington, VT 05363

    Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy

    Chad Lackey Deerfield Valley Real Estate

    5 Camelot Dr, Wilmington, VT 05363
  • 21 Big Bend Loop, Wilmington, VT 05363
    21 Big Bend Loop, Wilmington, VT 05363
    21 Big Bend Loop, Wilmington, VT 05363
    /59

    $354,900

    • 3 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    21 Big Bend Loop, Wilmington, VT 05363

    Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas. Step inside through the spacious

    Kelsey Malloy Keller Williams Realty Metro-Keene

    21 Big Bend Loop, Wilmington, VT 05363
  • 36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    36 Woffenden Rd, Wilmington, VT 05363
    /41

    $2,799,000

    $2M PRICE DROP
    • 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
    404 Fox Mountain Rd, Wilmington, VT 05363
    /39

    $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

    $154,900

    $44K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 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 1 acre 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
  • 49 West Rd, Wilmington, VT 05363
    49 West Rd, Wilmington, VT 05363
    49 West Rd, Wilmington, VT 05363
    /28

    $425,000

    • 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
  • 28 Lightning Ledge Way, Wilmington, VT 05363
    28 Lightning Ledge Way, Wilmington, VT 05363
    28 Lightning Ledge Way, Wilmington, VT 05363
    /23

    $465,900

    $33K PRICE DROP
    • 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
  • 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
  • 67 Castle Hill Rd, Wilmington, VT 05363
    67 Castle Hill Rd, Wilmington, VT 05363
    67 Castle Hill Rd, Wilmington, VT 05363
    /43

    $747,500

    • 5 Beds
    • 3.5 Baths
    • 3,436 Sq Ft

    67 Castle Hill Rd, Wilmington, VT 05363

    Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham’s boat launch and beach areas — truly four-season

    Adam Palmiter Berkley & Veller Greenwood/Dover

    67 Castle Hill Rd, Wilmington, VT 05363
  • 798 Vermont Route 100, Wilmington, VT 05363
    798 Vermont Route 100, Wilmington, VT 05363
    798 Vermont Route 100, Wilmington, VT 05363
    /43

    $774,000

    • 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
  • 555 Vermont 9, Wilmington, VT 05363
    555 Vermont 9, Wilmington, VT 05363
    555 Vermont 9, Wilmington, VT 05363
    /42

    $449,990

    $125K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    555 Vermont 9, Wilmington, VT 05363

    Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating

    Colt Hazell Flex Realty

    555 Vermont 9, Wilmington, VT 05363
  • 41 Two Brook Dr, Wilmington, VT 05363
    41 Two Brook Dr, Wilmington, VT 05363
    41 Two Brook Dr, Wilmington, VT 05363
    /47

    $798,000

    $100K PRICE DROP
    • 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
  • 216 Ghastly Job Way, Wilmington, VT 05363
    216 Ghastly Job Way, Wilmington, VT 05363
    216 Ghastly Job Way, Wilmington, VT 05363
    /34

    $460,000

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

    216 Ghastly Job Way, Wilmington, VT 05363

    Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

    Monique White Deerfield Valley Real Estate

    216 Ghastly Job Way, Wilmington, VT 05363
  • 238 Stowe Hill Rd, Wilmington, VT 05363
    238 Stowe Hill Rd, Wilmington, VT 05363
    238 Stowe Hill Rd, Wilmington, VT 05363
    /59

    $3,495,000

    • 9 Beds
    • 11 Baths
    • 6,726 Sq Ft

    238 Stowe Hill Rd, Wilmington, VT 05363

    Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    238 Stowe Hill Rd, Wilmington, VT 05363
  • 34 Rock Split Way, Wilmington, VT 05363
    34 Rock Split Way, Wilmington, VT 05363
    34 Rock Split Way, Wilmington, VT 05363
    /39

    $520,342

    • 3 Beds
    • 3 Baths
    • 1,521 Sq Ft

    34 Rock Split Way, Wilmington, VT 05363

    Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, flows seamlessly into

    Megan Quinn Southern Vermont Realty Group

    34 Rock Split Way, Wilmington, VT 05363
  • 0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363
    0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363
    0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363
    /29

    $115,000

    • Land
    • 5 Acres
    • $23,000 per Acre

    0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363

    Beautiful 5-Acre Vermont Lot with Mountain Views & Potential for Two Home Sites. Discover a rare opportunity to own a stunning 5-acre parcel in southern Vermont, ideally located on Route 100 just north of downtown Wilmington. This exceptional property offers the perfect setting for your dream home—or the potential to build two. Preliminary soil testing supports the potential for two separate

    Monique White Deerfield Valley Real Estate

    0 Happy Haven Rd Unit 5097175, 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
    /17

    $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
    /60

    $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
  • 41 Country Club Rd, Wilmington, VT 05363
    41 Country Club Rd, Wilmington, VT 05363
    41 Country Club Rd, Wilmington, VT 05363
    /14

    $50,000

    • Land
    • 12,632 Sq Ft
    • $172,414 per Acre

    41 Country Club Rd, Wilmington, VT 05363

    Set on 0.29 acres along a quiet dead-end, town-maintained paved road, this property offers a convenient and peaceful setting. The driveway is already in place, electric underground service is on site, and a natural spring is located on the property. Nearby access to the VAST Trails. Included in the sale is a 2015 Jayco Eagle Premier RV, providing comfortable seasonal living or a ready-made

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    41 Country Club 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
    /18

    $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
  • Lot 118 High Top Rd, Wilmington, VT 05363
    Lot 118 High Top Rd, Wilmington, VT 05363
    Lot 118 High Top Rd, Wilmington, VT 05363
    /23

    $30,000

    • Land
    • 21,780 Sq Ft
    • $60,000 per Acre

    Lot 118 High Top Rd, Wilmington, VT 05363

    Section B building lot! 1/2 Acre of level, flat land at the end of the cul-de-sac. Site is untested. Build your dream home and start planning your vacation getaway design! As a Lot owner, you may enjoy all of the recreational amenities Chimney Hill Resort offers on its 1,200 Acre Campus. Once you start building, Chimney Hill Owners Association also supplies a water line at the street for you to

    Sigrid Pickering Chimney Hill Realty

    Lot 118 High Top Rd, Wilmington, VT 05363
  • 2 Brook Ln, Wilmington, VT 05363
    2 Brook Ln, Wilmington, VT 05363
    2 Brook Ln, Wilmington, VT 05363
    /4

    $35,000

    • Land
    • 10,890 Sq Ft
    • $140,000 per Acre

    2 Brook Ln, Wilmington, VT 05363

    Nice building lot located in the Two Brook community, conveniently situated near Haystack Golf Course and just minutes from skiing, golf, lakes, and snowmobiling. This attractive parcel offers a peaceful setting with common land bordering the rear of the property and a stream flowing through the lot, adding to its natural appeal. Power, public water, and public sewer infrastructure are available

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    2 Brook Ln, Wilmington, VT 05363
  • 45 Mowing Way, Wilmington, VT 05363
    45 Mowing Way, Wilmington, VT 05363
    /2

    $45,000

    • Land
    • 10,890 Sq Ft
    • $180,000 per Acre

    45 Mowing Way, Wilmington, VT 05363

    Level building lot with public sewer and water at the street. Across from the Haystack Golf Course for easy year round enjoyment. Direct snowmobile access from the lot. A short drive to the public boat launch at Lake Whitingham or Mount Snow ski resort.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Mowing Way, Wilmington, VT 05363
  • 0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
    /24

    $140,000

    • Land
    • 1.4 Acres
    • $100,000 per Acre

    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363

    Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful

    Grayson VanHendrick Flex Realty

    0 Scattered Timber Rd Unit 5094122, 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
  • 14 High Top Rd Unit B124, Wilmington, VT 05363
    14 High Top Rd Unit B124, Wilmington, VT 05363
    14 High Top Rd Unit B124, Wilmington, VT 05363
    /60

    $535,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,397 Sq Ft

    14 High Top Rd Unit B124, Wilmington, VT 05363

    Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are

    Sigrid Pickering Chimney Hill Realty

    14 High Top Rd Unit B124, Wilmington, VT 05363
  • 18 Quail Ct, Wilmington, VT 05363
    18 Quail Ct, Wilmington, VT 05363
    18 Quail Ct, Wilmington, VT 05363
    /33

    $489,000

    • 4 Beds
    • 2 Baths
    • 2,070 Sq Ft

    18 Quail Ct, Wilmington, VT 05363

    Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large

    Adam Palmiter Berkley & Veller Greenwood/Dover

    18 Quail Ct, 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
    /26

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    Beautiful three story Powderhorn townhome on the slopes of Haystack Mountain at the exclusive Hermitage Club Ski Resort — a true four-season retreat with thoughtful upgrades that set it apart from anything else in the development. Wake up to sunrise winter views over the mountains through expansive windows thanks to the end unit location. Enjoy woodsy scenery over your private deck and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • 52 Ruth Way, Wilmington, VT 05363
    52 Ruth Way, Wilmington, VT 05363
    52 Ruth Way, Wilmington, VT 05363
    /59

    $425,000

    • 4 Beds
    • 3 Baths
    • 2,345 Sq Ft

    52 Ruth Way, Wilmington, VT 05363

    Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

    Donna Brown Skihome Realty

    52 Ruth Way, 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
    /20

    $39,900

    $10K PRICE DROP
    • 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
  • 60 E Brook Crossing, Wilmington, VT 05363
    60 E Brook Crossing, Wilmington, VT 05363
    60 E Brook Crossing, Wilmington, VT 05363
    /45

    $399,000

    $60K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    60 E Brook Crossing, Wilmington, VT 05363

    Tucked among mature trees in the desirable lower section of Chimney Hill, this charming home offers comfort, character, and easy living. A gently sloping gravel driveway and attached converted garage provide year-round convenience, while beautifully established perennial gardens and a gently sloping yard create an inviting outdoor setting rarely found in the area. Inside, the home exudes warmth

    Erica Reynolds Southern Vermont Realty Group

    60 E Brook Crossing, Wilmington, VT 05363

Showing Results 1 - 40, Page 1 of 2

Vermont Windham County

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 $794,675.
How many homes have sold over the last 12 months in Wilmington, VT?
73 homes have sold in Wilmington, VT over the last 12 months.
What is the average household income in Wilmington, VT?
The average household income in Wilmington, VT is $79K.
What are the most popular zip codes in Wilmington, VT?
The most popular zip codes in Wilmington, VT include 05363, 05301, 05356, 05361 and 05342.
How much do you need to make to afford a house in Wilmington?
The median home price in Wilmington is $504,950. If you put a 20% down payment of $101,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, 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. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Wilmington is $79K.
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 Prices in Wilmington, VT

The median home sale price in Wilmington, VT is $490,000, up 6% year-over-year. Homes in Wilmington sell in 105 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$490,000
Median Single Family Sale Price
$495,000
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$341,000
Median 1 Bedroom Sale Price
$354,000
Average Price Per Sq Ft
$336
Number of Homes for Sale
45
Last 12 months Home Sales
73
Months of Supply
7.40
Median List Price
$504,950
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
6%
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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.

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