37

Chimney Hill, VT Homes for Sale with Garage

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  • /29

    $420,000

    $169K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 3,518 Sq Ft

    343 Haystack Rd, Wilmington, VT 05363

    An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above

    Agent Photo

    Jessica Citera

    Cummings & Co

    343 Haystack Rd, Wilmington, VT 05363
  • /24

    $839,000

    • 4 Beds
    • 4.5 Baths
    • 3,696 Sq Ft

    7 Yodeling Ln, West Dover, VT 05356

    Beautiful 2008 log home nestled at the base of the Mount Snow ski resort, just down from Carinthia. This spectacular build has all the privacy and size you'd want in a private home, with all the convenience of being near the mountain. The home features a large open concept floor plan with vaulted kitchen and dining room areas, kitchen with island and stainless appliances, an expansive great room

    Adam Palmiter Berkley & Veller Greenwood/Dover

    7 Yodeling Ln, West Dover, VT 05356
  • /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
  • /22

    $315,000

    • 3 Beds
    • 3.5 Baths
    • 1,550 Sq Ft

    10 Tenth Ln Unit 31, Wilmington, VT 05363

    Lovely 3 bedroom, 3.5 bath townhouse just off the Haystack Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club and Mount Snow ski resorts. The deck overlooks the green mountains and is just off the 10th fairway. This unit features a vaulted open concept living room with stone hearth and efficient wood stove, spacious dining area leading out

    Adam Palmiter Berkley & Veller Greenwood/Dover

    10 Tenth Ln Unit 31, Wilmington, VT 05363
  • /27

    $249,900

    • 2 Beds
    • 1.5 Baths
    • 2,184 Sq Ft

    6 Church St, Wilmington, VT 05363

    Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home

    Julie Lowe Lowe's Real Estate, LLC

    6 Church St, Wilmington, VT 05363
  • /56

    $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
  • /47

    $269,000

    $20K PRICE DROP
    • 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
  • /41

    $2,699,000

    $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

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • /41

    $289,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356

    Adjusted to $289,000 making this the best value in Dover Green. Enjoy the best of Southern Vermont from this beautiful townhome in the sought-after Dover Green community, located just minutes south of Mount Snow. Whether you're looking for a year-round residence, a low-maintenance second home, or the perfect Vermont getaway, this spacious three bedroom, 2 two bath home offers comfort,

    Donald Koelsch Deerfield Valley Real Estate

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356
  • /42

    $424,990

    $150K 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
  • /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
  • /60

    $3,100,000

    $395K PRICE DROP
    • 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
  • /60

    $695,000

    • 3 Beds
    • 2 Baths
    • 1,885 Sq Ft

    48 High Top Rd Unit B130, Wilmington, VT 05363

    This is IT! Section B double Lot at the end of the Road! Renovated inside and out. expanded chalet style home features 3 bedrooms and two baths, a primary suite with a private covered porch with dedicated gas firepit and a bonus room awaiting your vision, landscaped grounds, woodstove-heated attached double garage with automatic doors, front deck with pergola, 2 year-old maintenance-free exterior

    Sigrid Pickering Chimney Hill Realty

    48 High Top Rd Unit B130, 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
  • /59

    $989,900

    • 4 Beds
    • 3 Baths
    • 5,697 Sq Ft

    66 Somerset Rd, Searsburg, VT 05363

    LOW TAXES! Six oversized garage bays across two multi-level outbuildings, direct access to National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

    Erica Reynolds Southern Vermont Realty Group

    66 Somerset Rd, Searsburg, VT 05363
  • /29

    $789,000

    • 5 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    15 Sawmill Village Way, Dover, VT 05356

    Beautiful contemporary farmhouse in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This bright and airy farmhouse design sits on a private level lot, and has been completely renovated to be turn key for immediate enjoyment. The interior boasts a vaulted living room with large windows, great natural light, and a gas fireplace, there is an updated chefs

    Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Sawmill Village Way, Dover, VT 05356
  • /32

    $875,000

    • 4 Beds
    • 4 Baths
    • 3,374 Sq Ft

    11 Stone Ridge Loop, Dover, VT 05356

    Beautiful custom home in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This contemporary farmhouse design has been just recently updated throughout to offer country charm with modern amenities for turn key enjoyment. The interior boasts a large great room with soaring windows, great natural light, new wood flooring throughout, a new gas fireplace on

    Adam Palmiter Berkley & Veller Greenwood/Dover

    11 Stone Ridge Loop, Dover, VT 05356
  • /60

    $2,495,000

    $394K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 6,400 Sq Ft

    56 Handle Rd, Dover, VT 05356

    Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler’s panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood

    Rich Caplan Deerfield Valley Real Estate

    56 Handle Rd, Dover, VT 05356
  • /32

    $728,000

    $47K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    15 Bears Den Rd, Dover, VT 05356

    A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living.This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front

    Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Bears Den Rd, Dover, VT 05356
  • /16

    $336,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    12A Dover Green Loop, Dover, VT 05356

    Move right in and get ready to enjoy the upcoming ski season. This mostly updated 3 bed 2 bath condo at Dover Green is ready for its next owners. With the newly updated kitchen and recently updated bathrooms you can enjoy your time on the mountain before returning to your warm and cozy getaway just a few minutes away. There's a wood burning fireplace anchoring the large living room with high

    Mike Masters Four Seasons Sotheby's Int'l Realty

    12A Dover Green Loop, Dover, VT 05356
  • /47

    $449,000

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

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363

    Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready!Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse

    Sigrid Pickering Chimney Hill Realty

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363
  • /50

    $389,000

    $46K PRICE DROP
    • 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
  • /51

    $899,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    33 Carinthia Dr, Dover, VT 05356

    LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Dr, Dover, VT 05356
  • /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
  • /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
  • /43

    $1,975,000

    • 5 Beds
    • 4.5 Baths
    • 5,063 Sq Ft

    183 Old Mill Ln, Wilmington, VT 05363

    Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, shared lake access area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby ski areas of Mount

    Adam Palmiter Berkley & Veller Greenwood/Dover

    183 Old Mill Ln, Wilmington, VT 05363
  • /41

    $639,000

    • 3 Beds
    • 2 Baths
    • 2,408 Sq Ft

    28 Stugger Rd, Dover, VT 05356

    Mount Snow is less than five minutes away, and adventure starts right outside your door! Built in 2020 and offering over 2,400 square feet, this 3-bedroom, 2-bath home delivers the perfect blend of mountain convenience, comfort and four-season recreation. With direct VAST snowmobile access and an impressive heated 28' x 40' garage, this property is built for enjoying all that Vermont has to

    Chad Lackey Deerfield Valley Real Estate

    28 Stugger Rd, Dover, VT 05356
  • /48

    $384,900

    $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    9F Brumms Way Unit 9F, Dover, VT 05356

    Beautiful end unit on edge of Bear’s Crossing Condo and Home Community with a stream and the forest as your neighbor. Close to the Ski Home trail. This mixed community is 2 minutes to Mount Snow Ski Resort and to mixed use trails for snowmobiling, xcountry skiing and mountain biking. There is also a shuttle running regularly to the resort and beyond! This unit is “turn key” with 2 bedrooms and a

    Steve Goldfarb Deerfield Valley Real Estate

    9F Brumms Way Unit 9F, Dover, VT 05356
  • /41

    $999,000

    • 4 Beds
    • 4.5 Baths
    • 5,050 Sq Ft

    3 Shannon Ridge Rd, Dover, VT 05356

    Some homes are renovated. Others are carefully crafted. 3 Shannon Ridge Road is unmistakably the latter.At first glance, the home feels elegant. Spend time inside, however, & its character begins to emerge: 16-ft.-long wide pine floors secured w/ traditional square nails, remarkably high ceilings, beautifully composed architecture, expansive windows, live-edge wood, a kitchen for entertaining and

    Jacki Murano Southern Vermont Realty Group

    3 Shannon Ridge Rd, Dover, VT 05356
  • /60

    $6,898,000

    New Construction
    • 5 Beds
    • 8 Baths
    • 4,000 Sq Ft

    88 Mann Rd, Wilmington, VT 05363

    A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At

    Rich Caplan Deerfield Valley Real Estate

    88 Mann Rd, Wilmington, VT 05363
  • /33

    $249,000

    • 1 Bed
    • 468 Sq Ft

    246 Mann Rd, Wilmington, VT 05363

    Location, location, location! This rare opportunity is surrounded by the beautiful Haystack Golf Course, offering an unbeatable setting in one of southern Vermont's premier resort destinations. The property currently features a camp and a one-car garage, allowing you to enjoy the land immediately while planning your dream home or future getaway. Just minutes from Mount Snow, The Hermitage Club,

    Jeffrey Brisson Cohn & Company

    246 Mann Rd, Wilmington, VT 05363
  • /19

    $449,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    15 Haymaker Ln Unit 6D, Wilmington, VT 05363

    Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

    Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Haymaker Ln Unit 6D, Wilmington, VT 05363
  • /7

    $3,999,000

    New Construction
    • 5 Beds
    • 8 Baths
    • 6,500 Sq Ft

    5 Old Mill Crossing, Wilmington, VT 05363

    Old Mill on Haystack Mountain is a mountain residence designed for the next chapter of family life, set on 3.58 acres within the gates of The Hermitage Club with views of the Haystack trails. With over 6,000 square feet of finished living space, the home offers the scale and flexibility to comfortably accommodate children, grandchildren, friends, and extended family while still providing a sense

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    5 Old Mill Crossing, Wilmington, VT 05363
  • /60

    $1,400,000

    • 6 Beds
    • 6 Baths
    • 3,639 Sq Ft

    4 Encore Place, Dover, VT 05356

    Location is key with this turnkey home - Carinthia and the Grommet surface lift are just across the street, and you can practically ski home - it doesn't get much better. This beautiful 6-bedroom, 6-bath home offers a cozy living room with a fieldstone fireplace for that après-ski warmth and over 3600 s.f. of living space. The landscaping provides patio privacy for barbecues and hot tub time for

    Regina Perrotto Skihome Realty

    4 Encore Place, Dover, VT 05356
  • /36

    $319,000

    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    12 Par Dr Unit 12, Wilmington, VT 05363

    Enjoy year-round Vermont living in this classic Spyglass townhome that is located right on the 10th fairway of the Haystack Golf course. Offering 3 bedrooms plus a sleeping loft and 3.5 baths. Designed for comfort and convenience, the main level features a mudroom, an open-concept living and dining area with vaulted ceilings, a fully equipped kitchen, and a cozy wood-burning fieldstone fireplace.

    Rich Caplan Deerfield Valley Real Estate

    12 Par Dr Unit 12, Wilmington, VT 05363
  • /50

    $475,000

    • 3 Beds
    • 3.5 Baths
    • 1,799 Sq Ft

    37 First Ln Unit 22, Wilmington, VT 05363

    Enjoy views of the Haystack Golf Course from this bright and spacious townhouse overlooking the course. The deck provides the perfect setting for outdoor dining, grilling, and entertaining, the sun-filled main level features an open floor plan with vaulted ceilings, exposed wood beams, skylights, updated flooring, and a striking fieldstone LP Gas fireplace. The kitchen offers wood cabinetry,

    Donald Koelsch Deerfield Valley Real Estate

    37 First Ln Unit 22, Wilmington, VT 05363
  • /47

    $1,995,000

    • 6 Beds
    • 6.5 Baths
    • 5,545 Sq Ft

    420 Ray Hill Rd, Wilmington, VT 05363

    This impressive 6-bedroom, 7-bath farm-style timber frame home, built by Davis Frame and featured on their website as “The Great White Barn,” sits on 3.51 acres just minutes from the Hermitage Club, Mount Snow, downtown Wilmington, lakes, hiking, golf, and VAST trails. Formerly known by its previous owners as “La Maison de Pommes” (House of Apples) for its old apple orchard setting, the home was

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    420 Ray Hill Rd, Wilmington, VT 05363
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