Chimney Hill, VT Homes for Sale under $500,000

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

Spacious townhome at an incredible price in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This private end unit sits nestled towards the top of the development with great privacy and parking, and has had numerous recent upgrades to the roof, foundation, paint, siding, and whole house water filtration. The interior boasts a vaulted great room, wood

Adam Palmiter Berkley & Veller Greenwood/Dover

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

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

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

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

Beautifully remodeled Suntec townhome just down from the base of the Mount Snow ski resort. This larger style spacious 4 bedroom townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has been recently fully renovated inside and out for turn key enjoyment. Featuring a large open concept floor

Adam Palmiter Berkley & Veller Greenwood/Dover

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

Kelsey Malloy Keller Williams Realty Metro-Keene

One of a kind opportunity to be trailside at Mount Snow in a truly turn key completely updated unit. A rare chance to own a unit at Glen Run, at the base of Carinthia, with easy access to the earliest and latest trails open via the magic carpet, as well as to the newly built base lodge. This convenient one bedroom unit is on the ground floor affording easy access in and out via the rear slider,

Adam Palmiter Berkley & Veller Greenwood/Dover

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

Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with the development having direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick

Adam Palmiter Berkley & Veller Greenwood/Dover

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

Three-bedroom, two-bath home on just under a half-acre in Sugar Mill Village offering a functional layout, views of Mount Snow's trails and summit, and a location that puts the area's year-round recreation close at hand. The main level features an open kitchen with breakfast bar, full dining with slider to deck, and living area centered around a wood-burning fireplace, creating a comfortable

Jacki Murano Southern Vermont Realty Group

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

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

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

Woodsy and charming ski chalet just a short drive from the village of Wilmington and Harriman Reservoir, and 10 minutes to the Mount Snow ski resort. This home sits on a private wooded lot, nestled in the Chimney Hill community with easy access thanks to a circular driveway, and just down the hill from the amenities building. The home has been partially updated and cared for and features a large

Adam Palmiter Berkley & Veller Greenwood/Dover

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

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

Charming 3-Bedroom Condo Just Minutes from Mount Snow! Open House Monday Sept. 7, 10 - 12!! Welcome to your perfect Vermont getaway! This beautifully maintained 3-bedroom, 2.5-bath condo is ideally located in Southern Vermont, just minutes from the renowned Mount Snow Ski Resort and the Mount SnowGolf Course. Whether you're an outdoor enthusiast or seeking a peaceful retreat, this property offers

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

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

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

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

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

Classic 5-bedroom, 3-bath Wilmington, Vermont chalet offering three levels of living space, outdoor hot tub, stone firepit, multiple wood-burning fireplaces, and bonus space! Tucked away on a nice lot near the end of the road but still convenient to Mount Snow, Route 100, and downtown Wilmington.The main level is the heart of the home, with soaring cathedral ceilings, an open kitchen,

Jacki Murano Southern Vermont Realty Group

Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or

Patrice Schneider Southern Vermont Realty Group

Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning

Monique White Deerfield Valley Real Estate

NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy, convenience, and value in this immaculate 3-bedroom, 2-bath double-wide manufactured home offering approximately 1,300 square feet of comfortable one-level living. Set on 1.4+/- acres on a quiet dead-end road, this property offers a peaceful setting while remaining just a short drive to downtown Wilmington

Donald Koelsch Deerfield Valley Real Estate

Nestled in a convenient Lower Chimney Hill location, this charming country saltbox offers classic Vermont character, cozy comfort, and access to the many benefits of the Chimney Hill community. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace, the home provides a warm and inviting atmosphere for year-round enjoyment.Recent updates, including the roof and

Rich Caplan Deerfield Valley Real Estate

Brand NEW building exterior, windows, doors! This beautifully maintained, bright & spacious 3 bedroom, 3 bath, plus loft townhome, offers the perfect blend of space, comfort, and convenience just minutes from Mount Snow’s main base lodge, Carinthia Lodge, and the Hermitage Club. This home features three large bedrooms with high ceilings, a versatile loft, and open concept layout, providing plenty

Prema Fitzpatrick Real Broker LLC

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

Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More

Sigrid Pickering Chimney Hill Realty

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

Enjoy the best of Southern Vermont from this spacious and inviting condo, offering a wonderful and unique blend of comfort, convenience, and privacy. Ideally located just a short drive from Mount Snow and downtown Wilmington, this property is perfectly suited as a year-round vacation retreat or four-season home.The open concept second floor offers an effortless flow between the kitchen,

Meghan Buckley Skihome Realty

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

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

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

Owners open to offers! A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple

Adam Palmiter Berkley & Veller Greenwood/Dover