New Listing! Wilmington VT Home for sale $560,000 $234 per sq.ft.

$560,000 $234 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 3 Baths |   Total Sq. Ft. 2397  |  Acres: 0.81
Listed on Thursday Apr 30, 2026
Description: 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 connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, après ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more! See Listing Details & 60 images.

Under Contract Wilmington VT Home for sale $649,000 $346 per sq.ft.

$649,000 $346 per sq.ft. Wilmington VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1874  |  Acres: 2.7
Listed on Friday Nov 21, 2025
Description: Owners will consider reasonable offers. Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous westerly views over Haystack Mountain for sunsets year round. Inside you are treated to a warm living area with natural wood post and beam joinery, beautiful light through the many updated windows, a gas burning stove for easy ambiance, a gorgeous updated kitchen with stainless appliances and granite counters, spacious dining area which leads out to the side dining deck for entertaining, family room addition with vaulted ceiling, exposed beams, and half bath, main floor primary suite also with vaulted ceiling and spa-like full bath with soaking tub, double vanity, and tiled stand up shower, a walk-in closet with custom shelving, main floor laundry and pantry space, dual upstairs bedrooms with shared full bath, a full lower level with workshop and updated boiler, double mudroom entry with ample gear storage, and perennial landscaping. The original plans called for a garage addition which would be easy to add on, and the lovely landscaped open lot gives you plenty of options. A truly Vermont style home that works perfect as a weekend getaway, or retirement downsizing option. See Listing Details & 23 images.

Under Contract Wilmington VT Home for sale $1,300,000 $442 per sq.ft.

$1,300,000 $442 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 4 Baths |   Total Sq. Ft. 2944  |  Acres: 0.8
Listed on Thursday Mar 5, 2026
Description: A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an inviting open-concept kitchen, living, and dining area--ideal for gathering with family and friends. A cozy wood-burning fireplace creates the perfect ambiance on chilly evenings, while a wood stove adds both character and efficiency. Large windows invite in natural light and frame peaceful lake views. Step outside onto the spacious deck overlooking the water--an ideal spot for morning coffee, summer dinners, or simply relaxing while taking in the tranquil surroundings. Ideally located just minutes to the charming village of Wilmington for dining, shopping, and local events, and approximately 15 minutes to world-class skiing at Mount Snow. Outdoor enthusiasts will love the surrounding beautiful hiking trails, making this a true four-season retreat. Opportunities like this don't come along often -- lakefront living in such a prime location is truly special. See Listing Details & 43 images. Includes a Virtual Tour

$579,000 $398 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1455  |  Acres: 2.01
Listed on Tuesday Apr 7, 2026
Description: Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time, offering a comfortable mix of mountain charm and practical updates. A newly built deck creates the perfect place to take in the view, while inside, a Vermont Castings wood stove brings warmth and character to the vaulted living space, it's ideal for cozy apres-ski evenings. The efficient layout makes for easy maintenance, and the attached two-car garage provides excellent storage for skis, boards, bikes, and outdoor gear. Offered furnished for added convenience, this is an easy opportunity to settle in and start enjoying the Stratton lifestyle right away. With important improvements already completed, the home is ready to be enjoyed from day one. See Listing Details & 34 images.

$750,000 $375 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2000  |  Acres: 3.5
Listed on Friday Jan 16, 2026
Description: WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres. The main level boasts newly refinished oak floors, two bedrooms, a den or living area with fieldstone wood burning fireplace and dining/living space open to kitchen with built in cabinetry for functionality. Private primary suite on upper level with additional three season sun room to enjoy the vast country side landscape you're lucky enough to witness . The lower level of the residence has three areas ready for your next project turning these rooms into a recreation room, workshop, gym, which conveniently allows you to access the oversized one car garage . Brand new deck completed this past fall just waiting for you to soak in the mountaintop views stretching from Equinox to Magic including visibility of Gale Meadow Pond. You are in the heart of ski country only a few minutes to Stratton's SunBowl or main Base Lodge, yet a short drive to Manchester. This is an opportunity for the new owner to create their own dreams lucky enough to find this rare buy. The setting is the least of your worries. Come see what we are talking about. See Listing Details & 50 images.

Under Contract Winhall VT Home for sale $1,100,000 $257 per sq.ft.

$1,100,000 $257 per sq.ft. Winhall VT Home »

3 Beds | 5 Baths |   Total Sq. Ft. 4279  |  Acres: 1.1
Listed on Wednesday Mar 11, 2026
Description: Welcome home! This property is MOVE IN READY ! This exceptional contemporary is just minutes from the Stratton base lodge. Meticulously maintained and thoughtfully updated, this home is ideal for you and your guests! Designed for both relaxation and entertaining, the open-concept floor plan ensures everyone can gather with ease. Two spacious living areas provide wonderful flexibility for everyone. The beautifully updated kitchen offers a wonderful space to cook, gather, and entertain. Expansive windows throughout the home fill the interior with natural light while capturing seasonal winter views of Stratton Mountain. At day's end, retreat to the luxurious primary suite! Two upper-level bedrooms feature newly added ensuite amenities, providing comfort and privacy for family and visitors alike. The lower level offers a generous family room, a world-class ski tuning room--easily convertible to a home gym--along with a bathroom, two bonus rooms, and the utility area. Recent exterior improvements further elevate the property and include a new roof, fresh exterior paint, a renovated garage, and a redesigned driveway. This house is equipped with a Generac Generator, radiant heat in the primary bathroom and don't forget the covered wood shed to keep your firewood dry. This remarkable Stratton property offers move-in ready convenience and an exceptional mountain lifestyle just moments from the slopes. Join us at an OPEN HOUSE Sunday, April 5th from 11:00-2:00 PM or make an appointment for a showing! See Listing Details & 52 images.

$2,800,000 $711 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 3938  |  Acres: 27.99
Listed on Monday Jul 28, 2025
Description: Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings and grand French doors that flood the interior w/ natural light. At the heart lies a chef's kitchen, equipped with premier appliances, spacious center island, custom cabinetry--ideal for both daily living and entertaining. Perfectly tailored for hosting, the home includes a dedicated cocktail and coffee bar--rich with wood accents.Step outside to enjoy the convenience of a full outdoor kitchen. Whether you're entertaining or unwinding solo, this porch is a year-round sanctuary.The luxurious primary suite is a private retreat, thoughtfully curated w/ high-end finishes and indulgent amenities.A spa-inspired ensuite bath,w/ an oversized hammered copper soaking tub invites relaxation, a sleek glass fireplace adds ambiance.From the breathtaking views, modern design, & refined blend of indoor-outdoor living this home offers a rare opportunity to experience mountain living at its finest. An entertainer's dream & a serene space to call home. this extraordinary residence invites you to slow down, settle in & savor every moment. Barn & Extraordinary Upgrades. SHOWINGS BEGIN SATURDAY AUGUST 2. See Listing Details & 59 images.

$375,000 $210 per sq.ft. Woodbury VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1786  |  Acres: 1
Listed on Wednesday Mar 11, 2026
Description: Set on a spacious 1 +/- acre corner lot, this raised ranch offers comfort, functionality, and easy access to outdoor recreation. The attached two-car garage provides convenient direct entry into the lower level great room, making everyday living easy in all seasons. The main level features a bright and inviting living room with an electric fireplace, perfect for relaxing evenings in the cooler months and a wall air conditioning unit for the warm months. The eat-in kitchen offers plenty of space for casual dining and includes a door that opens to the back deck--ideal for enjoying morning coffee or summer grilling. This level also includes a full bath, a spacious primary bedroom with double closets, and a comfortable guest bedroom. Downstairs, the lower level provides a great room warmed by a cozy wood stove, creating a welcoming gathering space. You'll also find an additional guest bedroom, a half bath, laundry, and utility room. Outside, the open acre offers plenty of room to garden, play, or simply enjoy the surroundings. A small stream runs behind the home, adding to the charm, and a storage shed provides extra space for tools and outdoor equipment. Located at the corner of two town-maintained gravel roads, the property offers a country setting while being just up the hill from VT Route 14 for an easy commute. With numerous nearby lakes and ponds to explore, this home is a great base for enjoying Vermont's outdoor lifestyle. See Listing Details & 28 images.

$650,000 $311 per sq.ft. Woodbury VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2088  |  Acres: 48.6
Listed on Monday Apr 20, 2026
Description: Forty-eight and a half acres of Woodbury homestead has been waiting for you. Hill pasture rolls into mixed softwood forest as you climb the old farm road into the mature maple stand, where the ghost of an old sugarhouse still lingers among the trees. Apple trees, blueberries, organic gardens, trails that invite you to lose track of time. Views of the local hills remind you exactly where you are. This land has been lived on, loved, tended well and it shows. The home sits quietly tucked away from the road, conscientiously sited to let the sun do some of the work. Passive solar design fills the interior with natural light and warmth. The kind that feels authentic rather than forced. Built with intention, the craftsmanship inside rewards a slow look. Sawn tamarack boards, hand hewn timbers, Rutland slate, salvaged Vermont hardwood floors, and custom woodwork sourced from the land itself. Architectural salvage chosen with a discerning eye complements the hand-crafted natural interior elements. Three bedrooms, two full baths, a dedicated office and plenty of common area make the interior spacious and comfortable. There is a stillness about the place that the road noise can't reach. Inside and outside space negotiate here, equally, by design. Two porches, an elevated deck, and a gazebo invite you to linger in the spaces between nature and home. Here the practical and the purposeful coexist in easy harmony. A new high-efficiency LP wall-hung boiler with individual room zones, 4.4kw of roof-mounted solar panels net metering against your electric bill, two EV charging plugs and wiring for a generator. An attached workshop and garage for the projects that never quite finish, plus sheds for wood, and equipment. A second building site was designed for the property about a decade ago adding versatility with an eye toward the future. Woodbury's many lakes and ponds are just a stone's skip away and 'city' amenities in Hardwick, Montpelier, and Morrisville are all within easy reach. See Listing Details & 60 images.

$1,249,950 $411 per sq.ft. Woodbury VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 3041  |  Acres: 218
Listed on Friday Sep 26, 2025
Description: Welcome to 187 East Hill Road, an extraordinary 218-acre estate in the serene town of Woodbury, Vermont. This remarkable property is a rare find, offering unparalleled natural beauty and luxurious rustic living. At the heart of this expansive estate lies a charming log cabin, meticulously crafted with exotic hardwoods that infuse warmth and character into every room. Flooring is Brazilian Cherry, the kitchen is custom crafted of Guyana Mahogany, the great room ceiling is finished in Spanish cedar, and the expansive decks and porches are made of luxurious Ipe decking. The cabin seamlessly blends with its surroundings, providing a cozy retreat while offering modern comforts. The property boasts extensive frontage on the pristine Woodbury Lake. Enjoy serene water views from your private dock, or while kayaking, fishing, and peaceful lakeside moments on your private beach, or your additional deeded access to the lake. The estate's vast network of trails invites you to explore the diverse landscape, whether by foot, horseback, or ATV, making it an outdoor enthusiast's dream. Trails follow waterfalls on one border of the property and will allow the perfect location for a zen / meditation garden allowing the opportunity to get lost in the sound of rushing water as your stress melts away. Whether you seek a private retreat, a family compound, or a nature lover's paradise, 187 East Hill Road offers endless possibilities. See Listing Details & 52 images. Includes a Virtual Tour

$125,000 $163 per sq.ft. Woodford VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 768  |  Acres: 0.28
Listed on Tuesday Apr 21, 2026
Description: Your wait is over--an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach and boat rights to the lake. Set in a peaceful, nature-filled setting, this property is ready for your vision. The existing cottage requires significant foundation repair or replacement, presenting the perfect chance to restore the structure or start fresh and build your dream mountain lake retreat. A rare opportunity for investors, builders, or buyers looking to create something special in a truly desirable Vermont location. Being sold As-Is. This is a cash-only sale. See Listing Details & 14 images.

Under Contract Woodstock VT Home for sale $530,000 $276 per sq.ft.

$530,000 $276 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $165,000 down 31% on April 17th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 6.88
Listed on Friday Sep 12, 2025
Description: This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car garage with ample storage above is connected by a breezeway. 3 mini splits for efficiency and comfort. Backup generator, pellet stove, wood stove. Newer heat pump water heater, new windows. Huge shed barn for storage or workshop. See Listing Details & 43 images.

Under Contract Woodstock VT Home for sale $639,000 $293 per sq.ft.

$639,000 $293 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2183  |  Acres: 1.32
Listed on Friday Mar 20, 2026
Description: You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This thoughtfully updated raised ranch blends comfort, style, and convenience seamlessly with plenty of natural light filling much of the home. Recent improvements include beautifully renovated bathrooms, gleaming hardwood floors, a new roof and central air for year-round comfort. The kitchen is the heart of the home, perfectly positioned for cooking, gathering and listening to laughter fill the living room just steps away. The exercise room and sitting room offer flexible spaces for hosting family and friends or for escaping to a quiet space to work from home. The expansive deck provides a perfect setting for relaxing or entertaining as it overlooks the front yard while the backyard features a fenced-in space ideal for your four-legged companions to enjoy. Just minutes from Woodstock Union High School and the charming shops, restaurants, and amenities of downtown Woodstock, this home is ready to begin its next chapter with you! See Listing Details & 27 images. Includes a Virtual Tour

$749,000 $451 per sq.ft. Woodstock VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 1660  |  Acres: 0.19
Listed on Saturday Mar 28, 2026
Description: Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and pickleball courts. The homeowners have meticulously updated the property, featuring a stunning new kitchen and a refreshed second-floor bath, blending modern comfort with timeless charm. Unwind on the covered porch with a favorite drink while soaking in the serene surroundings. The inviting living room has a cozy gas fireplace, perfect for cool evenings. The spacious dining area opens to the expanded kitchen, boasting elegant cabinetry, sleek quartz countertops, and top-quality appliances. Newly installed pine flooring adds sophistication throughout. With three spacious bedrooms and two updated bathrooms, each room is designed for comfort. A versatile sitting room off the primary bedroom is perfect as a playroom or quiet study. Additional features include a new boiler, new dining room windows, and upgraded wiring with 200 AMP service. The property also offers a two-stall garage with partially finished space above, presenting endless customization possibilities. Whether you're seeking a forever home or a peaceful retreat, this move-in-ready gem is a must-see! See Listing Details & 39 images.

Under Contract Woodstock VT Home for sale $817,000 $296 per sq.ft.

$817,000 $296 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2760  |  Acres: 10.1
Listed on Thursday Jul 3, 2025
Description: This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house .The dwelling has a wrap around deck overlooking the meadows and pond with views to the south. Antique stone walls are reminiscent of days gone by .If privacy but convenience to Woodstock village is your goal you need not look further. Some of the features include hardwood floors , open floorplan that includes dining and living room , large downstairs game room. Easy access to Killington, Okemo Mountain and of course Woodstock's own Saskadena Six for Skiing . Golf, tennis . biking and fishing are just a few of the many outdoor activities in the area . Pentangle Arts provides music and theater throughout the year. Woodstock was named the prettiest small town in America . Come make it your home in this amazing property. Call today for an appointment. See Listing Details & 57 images.

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