Under Contract Jamaica VT Home for sale $449,000 $255 per sq.ft.

$449,000 $255 per sq.ft. Jamaica VT Home »


Price Change! Reduced by $50,000 down 11% on March 1st 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1760  |  Acres: 2.1
Listed on Monday Jun 17, 2024
Description: Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand new appliances including refrigerator, stove, microwave, and dishwasher. Gather around the large dining room table when hosting meals with friends. Main level has a full bathroom and bedroom with a king bed. Second floor has a bunk room and a room with a king bed, they share another full bathroom. All bedrooms feature new plush carpeting with antimicrobial memory foam padding and ample closet and dresser space. The finished lower level offers entertainment in the form of a game room with a flat-screen TV and bean bag chairs. The outdoor space is a double lot that showcases the serene Vermont landscape. Included in the sale is a 1 acre parcel that offers additional privacy and/or future possibility to develop a second home (buyer to do due diligence). Hot Toddy Hill provides the perfect backdrop for your Vermont dreams! Being offered less a few personal items, ask us about our list of improvements! See Listing Details & 37 images.

$559,000 $272 per sq.ft. Jamaica VT Home »


Price Change! Reduced by $25,000 down 4% on March 19th 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2052  |  Acres: 2.1
Listed on Friday Feb 7, 2025
Description: Welcome to Sugar Chateau- Nestled in the serene landscape of Southern Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere. Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson Windows throughout the home as well. The finished lower level is ideal for entertainment or relaxation and provides additional living space with 3/4 bath, laundry room, den area and walk out access. Wonderful outdoor, living space- unwind on the spacious deck with stunning views of Vermont's natural beauty. Relax in the hot tub after a day of skiing or hiking. Experience the best of both worlds - tranquility and convenience. Located just 15 minutes from Stratton Mountain Resort and a short drive to Jamaica village, offering local shops, dining, and community events. Your Vermont retreat awaits, whether you're seeking a weekend getaway or a year-round residence, this charming log home offers a unique opportunity to embrace Vermont's lifestyle. Exciting Update! This stunning property has just received a price improvement, making it an even greater opportunity for buyers seeking a quintessential Vermont retreat. Join us for an Open House on Saturday, March 22nd, from 12-2 PM to experience the charm and serenity of this beautiful home in person. See Listing Details & 27 images.

Under Contract Jamaica VT Home for sale $575,000 $394 per sq.ft.

$575,000 $394 per sq.ft. Jamaica VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1459  |  Acres: 15
Listed on Tuesday Dec 17, 2024
Description: Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or let your imagination run wild! The main level of the home offers a nice size mudroom for all your gear, a 3/4 bath, large eat in kitchen and large living area with wood burning fireplace to snuggle up to on cold winter days. Upstairs has three bedrooms with large closets and a full bath. The large covered porch and front yard allows ample space to enjoy the outdoors, entertain or relax. The large full basement has house utilities, laundry and plenty of space for storage. This home offers some unique features which you have to come check out for yourself. See Listing Details & 30 images.

$590,000 $218 per sq.ft. Jamaica VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2704  |  Acres: 2.37
Listed on Friday Mar 7, 2025
Description: This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home overlooks the lovely wooded property and a back deck that enjoys long hours of sun. The main level features the primary bedroom ensuite, a bunk room, an additional bathroom, and a bonus room that can serve as a den, office, or overflow sleeping. The lower level includes a large mudroom for all your gear, a spacious bedroom, a bathroom, and another bonus room for entertaining. The house is set well off a quiet country road yet convenient to the quaint village of Jamaica, with stone walls and gladed woods. A two-car garage, storage shed for all your toys, and a timber shed complete this charming property! See Listing Details & 36 images.

$1,750,000 $209 per sq.ft. Jamaica VT Home »

7 Beds | 8 Baths |   Total Sq. Ft. 8364  |  Acres: 16.05
Listed on Friday Jul 5, 2024
Description: Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An open floor plan unfolds into a breathtaking two-story great room, showcasing panoramic mountain views. Prepare feasts fit for royalty in the commercial-grade kitchen, then unwind in one of 6 spacious bedrooms, each with a private en-suite bath. Rise with the sun on the first-floor primary suite: Cozy up by the fireplace, or step out to the deck & savor the scenery with a steaming cup of coffee. Unwind in the lower-level living room, a haven for gatherings. An exercise room, office, & billiard room cater to every mood, while a walk-out door beckons you farm-side. A two-level barn currently houses a menagerie of friendly goats, sheep, chickens, & ducks! A heated garage provides convenient access, while a workshop & storage area keep things organized. The milking room & stalls below are ready for those who dream of a farm-to-table lifestyle. Plus, a charming 1-bedroom, 1-bath guesthouse offers the perfect space for visiting family, friends or potential rental income. Just 4 mi. from Stratton & close to Bromley, Magic & Snow, Cold Moon Farm puts you at the heart of all that Vermont offers! See Listing Details & 40 images.

$2,399,000 $672 per sq.ft. Jamaica VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3569  |  Acres: 366.1
Listed on Saturday Sep 30, 2023
Description: Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round! See Listing Details & 35 images. Includes a Virtual Tour

$4,495,500 $817 per sq.ft. Jamaica VT Home »

4 Beds | 6 Baths |   Total Sq. Ft. 5500  |  Acres: 44.47
Listed on Saturday Mar 1, 2025
Description: Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate retreat. The moment you arrive; the home's striking presence is undeniable. A porte-cochère welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef's kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island. Exposed douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home's most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the home's entertainment offerings. The seamless connection between indoor and outdoor living is one of the home's greatest attributes. Heated pool, hot tub and fire place sit against a backdrop of vast mountain views. The surrounding landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens. See Listing Details & 60 images.

$8,950,000 $668 per sq.ft. Jamaica VT Home »


Price Change! Reduced by $1,000,000 down 11% on March 28th 2025
6 Beds | 10 Baths |   Total Sq. Ft. 13393  |  Acres: 417.27
Listed on Tuesday Sep 24, 2024
Description: Accessible, but miles from the everyday. Camp Endo's mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef's kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo's extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy. See Listing Details & 41 images. Includes a Virtual Tour

Under Contract Killington VT Home for sale $599,000 $523 per sq.ft.

$599,000 $523 per sq.ft. Killington VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1146  |  Acres: 3.78
Listed on Tuesday Mar 11, 2025
Description: Perched on a small hillside surrounded by trees and Vermont foliage, this updated A-frame cabin is the definition of mountain tranquility. Two bedroom, two bath home with newly renovated kitchen featuring black soapstone countertops, high-end plumbing and Bertazzoni range. An open floor plan on the main level features a wood stove and plenty of space to dine, play games, or cozy up. Thoughtful details can be found throughout to include shiplap walls, designer lighting, custom storage, a functional pantry, and more. In the summer, enjoy the expansive deck stargazing, or in the winter, relax in the hot tub after a long day on Superstar. The home is located in a private neighborhood on a dead end road, and abuts hundreds of acres of Green Mountain National Forest, a wonderful neighbor to have, complete with a long standing tradition of protecting vast stretches of Vermont wilderness. Don't miss out on this prime Killington location, just a 12 minute drive to the Killington Mountain resort, 7 minutes to Pico Mountain, 3 minutes to Green Mountain National Golf Course, and minutes away to local hiking at Gifford Woods State Park, mountain biking, fishing and kayaking on Kent Pond, and more. See Listing Details & 27 images.

Under Contract Killington VT Home for sale $825,000 $284 per sq.ft.

$825,000 $284 per sq.ft. Killington VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2902  |  Acres: 1.2
Listed on Friday Feb 14, 2025
Description: Welcome to your ultimate mountain retreat! This stunning five-bedroom, three-bathroom ski chalet is perfectly located just minutes from Killington Resort, Pico Mountain, and under a mile from Green Mountain National Golf Course. Whether you're hitting the slopes in the winter or exploring Vermont's beauty year-round, this home offers the perfect balance of adventure and relaxation. Step inside and be greeted by a bright and inviting living room with ample natural light open into the updated kitchen, perfect for unwinding after a day on the mountain. This is an entertainment floorplan, game room in the lower level while the kitchen, living room and dining room are all open on the second floor. The primary suite on the top floor is your private sanctuary, boasting an en-suite bathroom, direct access to the loft, and a space for the home office. Enjoy mountain views from the loft, living room or game room! This home has been thoughtfully upgraded with a new roof on both the house and shed, two new mini-split air conditioning systems, an updated water pump, a water softener system, a fireplace and chimney liner, an updated septic system, and a replaced oil tank over the past several years. Outdoor enthusiasts will love the expanded deck with stairs to the shed, and strategic tree removal to enhance both views and privacy. Call today to schedule a private tour. See Listing Details & 39 images.

$1,150,000 $273 per sq.ft. Killington VT Home »


Price Change! Reduced by $350,000 down 30% on April 10th 2025
Waterfront on River Ottauquechee River
3 Beds | 4 Baths |   Total Sq. Ft. 4206  |  Acres: 1.77
Listed on Tuesday Sep 24, 2024
Description: Tucked away at the end of a quiet drive, this stunning Killington property is situated at the confluence of the Ottauquechee River, Roaring and Brimstone Brooks. Surrounded by nature on all sides, it's no surprise that this inspiring spot served for years as the home & studio of a beloved local artist. Gaze out from a comfortable chair on one of the spacious decks or the brook-side bench, listen to calming sounds of falling water, and you might just be inspired to pick up a paintbrush too. Inside, the scenery is just as special. The timber-framed home boasts big, high-ceiling living areas with impressively large windows for natural light and pleasing views. Tongue and groove pine ceilings and paneling as well as a cozy wood stove lend a comfortable, rustic feel to the space. The glass-walled hot tub room is breathtaking, as is the upstairs studio space, complete with floor to ceiling windows, a bathroom, and a utility sink. The home is permitted for three bedrooms, but there are plenty of other rooms to use as you choose, from office spaces to workout/game rooms and storage. The walkout basement is a handyman's dream, with large work areas and plenty of storage space, along with another living area with a wet bar, the 4th bathroom & laundry room. A tidy attached 2-car garage keeps the vehicles safe from the Vermont elements. A paragraph or two and a list of amenities simply won't suffice to describe this beautiful property - you'll want to experience it for yourself. See Listing Details & 57 images.

$1,589,000 $928 per sq.ft. Killington VT Home »

1 Beds | 3 Baths |   Total Sq. Ft. 1713  |  Acres: 1.08
Listed on Monday Dec 30, 2024
Description: A unique architect designed contemporary 2 home compound on one of the highest buildable lots in Killington. 2 homes to be built using Scandinavian technology, homes are designed as a semi-detached duplex (no common wall), offering privacy to each side. Home 1: 1,713 gross sq.ft (smaller unit to left in exterior renderings) Upon entering the home via the entry vestibule, you have an open library / TV area with an adjacent full bathroom and sauna space. The kitchen and living areas are beyond within a two-story space which includes full height triple pane windows, a wood-burning stove and a southern facing balcony. A heated storage and ski locker space is off the parking area and forms the "link" to the adjacent home 2. The second floor offers one large bedroom suite overlooking the two-story living space below as well as having a full bath with space for a stackable washer/dryer and a private balcony. At the walk out lower level there is a large open "art studio / rec room" which can be used by the buyer as they wish. A full bathroom and laundry are adjacent to the studio. Access to a private patio with a fire pit is at grade off the studio. See Listing Details & 6 images. Includes a Virtual Tour

$1,685,000 $620 per sq.ft. Killington VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2718  |  Acres: 0.9
Listed on Friday Apr 4, 2025
Description: KILLINGTON - DESIRED SKI-IN/SKI-OUT LOCATION! Seize this rare opportunity to own a stunningly updated mountain retreat with direct access to the legendary Great Eastern Trail via a deeded easement. Perfectly positioned for skiers, snowboarders, and outdoor enthusiasts, this home also offers strong short-term rental potential, making it a prime investment opportunity. Step inside to a bright and airy open-concept main level, where a newly renovated kitchen, dining area, and living room flow seamlessly under soaring cathedral ceilings. The brand-new, two-story windows showcase breathtaking mountain views and flood the space with natural light. There is one bedroom conveniently located on the main floor. A wood-burning stove was previously removed for rental safety, but the setup remains for easy reinstallation to bring extra warmth and charm. After an epic day on the slopes, relax in your private, newly installed hot tub, perfectly positioned for soaking in the mountain air. This home has been thoughtfully upgraded with new flooring on the main level, a newer efficient boiler, and beautifully updated bathrooms. The lower level features a spacious bedroom, full bath, laundry area, recreation room, and bonus room, while the upper level boasts a luxurious primary suite with a full bath, plus an additional bedroom with charming log bunk beds and another updated bath. Opportunities like this don't come often--act fast and make this Killington dream home yours today! See Listing Details & 48 images. Includes a Virtual Tour

$1,999,000 $405 per sq.ft. Killington VT Home »

6 Beds | 5 Baths |   Total Sq. Ft. 4934  |  Acres: 35.3
Listed on Friday Oct 11, 2024
Description: As you drive along the winding driveway, you'll discover an unparalleled level of privacy that sets this property apart. Situated on 35 acres of serene land, it's just minutes from Killington Resort, Pico Mountain, and everything Vermont has to offer. A spacious three-car garage keeps your vehicles sheltered while you unwind in the tranquil charm of this custom Tudor home. The main level features an expansive kitchen complete with a center island and double dishwashers, perfect for hosting large gatherings. Adjacent to the kitchen is a beautifully appointed dining room, followed by a comfortable living room and sunroom. On the upper level, you'll find six bedrooms, including a primary suite with a unique layout: a full bathroom and an additional half bath, plus two side-by-side closets and a walk-in closet for ample storage. The primary suite also includes a well-placed home office, offering a quiet retreat just steps from the action. If you're in need of more space, the basement is ready to be transformed into a large theater room, home gym, or billiards room. This home is equipped with modern systems, including an air conditioning system that ensures comfort during the warmer months. For those seeking refined elegance and complete privacy while remaining close to New England's largest ski resort, this property is a must-see. Call today to schedule your private tour! See Listing Details & 60 images. Includes a Virtual Tour

New Listing! Killington VT Home for sale $1,999,000 $625 per sq.ft.

$1,999,000 $625 per sq.ft. Killington VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3200  |  Acres: 0.8
Listed on Tuesday Apr 22, 2025
Description: Spectacular contemporary mountain home in the heart of Killington! This 5-bedroom, 4.5-bathroom retreat sits on 0.8 acres and offers 3,200 sq ft of thoughtfully designed living space. Enjoy breathtaking views of the ski slopes right from your spacious eat-in kitchen, complete with a large center island -- ideal for hosting après-ski gatherings. This home features a private ensuite with a kitchenette, providing versatile options for guest stays or short-term rental income. The open layout blends luxury and comfort, while modern finishes throughout elevate the living experience. After a day outdoors, relax in your private hot tub, rejuvenate in the sauna, or cozy up in the inviting living area. Additional highlights include: Proven rental income history over the past two years Separate additional rental space for enhanced income potential 560 sq ft attached garage for convenient storage and parking Walking distance to local restaurants, shops, and Killington nightlife. Unbeatable mountain location, just minutes from lifts, hiking trails, and all-season recreation. Whether you're looking for a full-time residence, vacation home, or income-producing property, this is a rare opportunity in one of Vermont's most desirable ski towns. See Listing Details & 52 images.

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