$570,000 $242 per sq.ft. Jamaica VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2359  |  Acres: 14.4
Listed on Wednesday May 20, 2026
Description: Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features bright, open living and dining spaces with large picture windows showcasing beautiful views in every direction. A fieldstone hearth with wood stove creates a warm and inviting atmosphere for entertaining, while the kitchen offers abundant storage. The main level includes three bedrooms, a ¾ bath, and a sun-filled mudroom/sunroom with wall-to-wall windows and its own propane stove. Upstairs, the spacious primary suite or bunk room retreat includes a full bath, cedar walk-in closet, and mountain views. The basement with half bath, and attached 2-car garage provide excellent storage, workshop, recreation, or future living space potential. Outside, enjoy expansive lawns, meadows, a screened gazebo, private trails, mature forest, stone walls from an old homestead, and a year-round creek. Endless hiking, snowmobiling, ATV riding, and outdoor adventure await right from the property. Energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, Daikin heat pumps and mini splits, rebuilt chimney, generator-ready setup, multiple heating options, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, this is a rare opportunity to own a true Vermont escape. See Listing Details & 35 images.

New Listing! Jamaica VT Home for sale $575,000 $475 per sq.ft.

$575,000 $475 per sq.ft. Jamaica VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 1211  |  Acres: 2.34
Listed on Thursday Jun 11, 2026
Description: Rare Multi-Dwelling Retreat with Endless Possibilities A truly exceptional and meticulously maintained property featuring three separate residences on one beautifully landscaped lot--a setup buyers often dream about but rarely find. The main residence is a stylish 2-bedroom, 2-bath contemporary home thoughtfully designed for comfortable living. Built with sustainability in mind, the home features an environmentally friendly geothermal system that provides efficient heating and cooling year-round. Complementing the main home are two charming tiny houses, each with its own unique character and appeal. Whether used for guests, rental income, extended family, or creative workspace opportunities, these versatile structures offer tremendous flexibility. The grounds are nothing short of spectacular. A beautiful pond with a sandy beach and cascading waterfall creates a private oasis right outside your door. Mature landscaping throughout the property provides beauty, tranquility, and a clear sense of pride of ownership. Adding to the property's appeal is a septic system permitted for three two-bedroom residences. This substantial infrastructure provides valuable flexibility for future use. Subject to applicable permits and approvals, the existing tiny houses could potentially be replaced with larger two-bedroom cabins, or bedroom capacity could potentially be reallocated to an expanded main residence. Properties offering multiple residences, income potential, privacy, natural beauty, and convenient access to Stratton are exceptionally rare. Here, much of the groundwork has already been completed: the infrastructure is installed, the homes are in place, and significant future potential remains. Don't miss this unique opportunity to own a one-of-a-kind Vermont retreat offering flexibility for today and possibilities for tomorrow. See Listing Details & 36 images.

$595,000 $416 per sq.ft. Jamaica VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1430  |  Acres: 0.7
Listed on Wednesday May 20, 2026
Description: Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system provides efficient heating and air conditioning year-round. In 2024, the basement underwent major upgrades, including mitigation with an improved support and drainage system, along with the installation of two new water tanks--providing long-term confidence and reassurance for the next owner. Ideally located near Stratton Mountain, Ball Mountain Dam, and Jamaica State Park, this home is a perfect base for four-season recreation--from skiing and snowboarding to hiking, swimming, and exploring nature. A true turnkey retreat in an unbeatable location! See Listing Details & 22 images.

New Listing! Jamaica VT Home for sale $839,000 $218 per sq.ft.

$839,000 $218 per sq.ft. Jamaica VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3840  |  Acres: 5.7
Listed on Monday Jun 8, 2026
Description: Only eight miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, and multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you and your family to have all the room you want today. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth and light. The addition includes a grand primary suite with soaring ceilings, views over the land, walk-in closet, large tiled bathroom with a tiled shower, powerful jet tub, and double vanity. With 5 total bedrooms, 4.5 baths, 2 living spaces, and 3 bonus rooms, there is space to host or work from this 3,840SqFt home. The expansive kitchen contains large countertops with space for seating as well as a window covered breakfast nook. The butler's pantry, complete with a wet bar, makes entertaining easy. Sit by the stove while snow falls across the pasture and enjoy your snow-globe like winter scene. On warm days, open the sliders to the brick patio, or to the back deck to grill, pick berries in the garden, walk the orchard trail, or watch the leaves change during the seasons. The home is located near the town of Manchester, ski mountains (Stratton, Bromley, and Mount Snow), excellent golf courses, and local renowned dining at Honeypie, River & Rye and Solo Farm & Table within easy reach. Bradley International Airport is two hours away, Boston is three, and New York City is four. This is a home you can enjoy now. One whose location, scale, and enchanting views provide the foundation to create your dream oasis. You deserve to enjoy the Vermont life you have been dreaming of, and make this home and timeless setting part of your family's legacy. See Listing Details & 37 images.

$850,000 $264 per sq.ft. Jamaica VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 3218  |  Acres: 2
Listed on Thursday May 14, 2026
Description: Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no matter the weather. Or you can relax in the hot tub after a long day and even enjoy the sounds of a local waterfall located just a short walk from the doorstep. A 1-bedroom apartment with a separate entrance gives this home more flexibility for family and friends to stay for extended visits. The two-car garage provides space for all the outdoor gear you could need to explore the Vermont wilderness year-round. This home has all you need to enjoy all the Vermont has to offer. See Listing Details & 57 images.

$1,040,000 $309 per sq.ft. Jamaica VT Home »

Waterfront on Pond Cole Pond
5 Beds | 5 Baths |   Total Sq. Ft. 3363  |  Acres: 0.6
Listed on Saturday Sep 6, 2025
Description: Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery. This home is designed to accommodate a life of both leisure and adventure. See Listing Details & 30 images.

$1,140,000 $279 per sq.ft. Jamaica VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 4193  |  Acres: 15.13
Listed on Tuesday Sep 9, 2025
Description: Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces highlighted by two fireplaces, creating a warm and inviting atmosphere. A bonus room is an art studio to expand your creative senses. Large windows capture the natural beauty of the surroundings, while a wraparound deck extends the living space outdoors--ideal for entertaining or simply enjoying the peaceful setting. The property is uniquely enhanced by two beautiful private ponds, And an abundance of perennial gardens, offering a serene and picturesque backdrop. Relax in the outdoor hot tub after a day on the slopes. Enjoy Highland Forests private beach access to Cole Pond, This grassy space with a dock is perfect for swimming, kayaking, and quiet enjoyment. Outdoor enthusiasts will appreciate the nearby Hiking and Snowshoe trail access, making this an ideal four-season retreat. Whether you're seeking a full-time residence or a Vermont getaway, this home delivers a rare combination of space, setting, and proximity to one of Southern Vermont's premier resorts. See Listing Details & 47 images.

$1,295,000 $426 per sq.ft. Jamaica VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 3040  |  Acres: 11.12
Listed on Saturday May 23, 2026
Description: One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want--an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two fireplaces with your favorite beverage while watching the snow fall. The great room features a 90-inch TV, perfect for watching your favorite sporting event. Outdoors, you'll find a grill and seating area for dining under the stars beside a six-person hot tub and an eight-person sauna. After your meal, gather around the fire pit to roast marshmallows and take in the beauty of the surrounding forest. No expense was spared in creating this extraordinary Vermont home--thoughtfully designed for comfort, connection, and unforgettable memories. See Listing Details & 36 images.

$2,399,000 $723 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

$8,200,000 $762 per sq.ft. Jamaica VT Home »

6 Beds | 10 Baths |   Total Sq. Ft. 10763  |  Acres: 416.27
Listed on Friday Feb 6, 2026
Description: Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape--ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home's elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities, See Listing Details & 60 images.

$559,900 $316 per sq.ft. Killington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1772  |  Acres: 1.23
Listed on Wednesday May 20, 2026
Description: Gorgeous four bedroom. Three bath home just completed with new heating system. New roof, new wiring, new hot tub. Everything new, rental potential 75,000 a year. Use half and ski half. On the market now for the first time, completed. Beautiful views of Pico ski area. See Listing Details & 6 images.

$574,000 $239 per sq.ft. Killington VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2900  |  Acres: 0.9
Listed on Wednesday Dec 31, 2025
Description: Live or work 2 minutes to Killington Resort's Skyeship Gondola! This unique property along the Route 4 flats is zoned mixed use for residential and/or commercial -- it is currently split into 4 offices but permitting allows for up to 5 bedrooms (sleeps 10). The upstairs has a separate entrance in the back, so could be easily split into a duplex as well. So many opportunities! The flat driveway offers easy access/plowing with parking for 10. There is also a full basement for ample storage. See Listing Details & 11 images.

$879,000 $581 per sq.ft. Killington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1514  |  Acres: 1.8
Listed on Wednesday May 27, 2026
Description: Welcome to your family's new vacation home! First time ever offered for sale by the original owner who used it as a family retreat. Located on 1.8 private acres, consisting of two lots +/- 0.9 acres each, one with a custom built four-bedroom home while the other offers the possibility of building another home. Just minutes to the lifts and action on Killington Road, the property is located at the end of a cul-de-sac with an unobstructed view of the mountains across Route 4. 64 East Lane is a modern looking ski house with a unique cedar exterior, steep rooflines, and a cathedral ceiling living room with a striking floor to ceiling ledge stone fireplace opposite a wall of glass overlooking the mountains. The open layout of the first floor, consisting of the kitchen, dining area and living room, is warm and functional for family gathering and entertaining. Also on the main floor is a full bedroom or den and full bathroom. On the second floor are three additional bedrooms, including the primary, and a second full bath. The dry basement is designed to be finished as a game room and additional living space with a wood burning stove. The home is well insulated, including in the interior walls. Carefully maintained over time, all large windows have been replaced and the exterior was power washed and stained recently. Come see for yourself and schedule a private showing today! Or attend an OPEN HOUSE Sat 5/30 10-12. See Listing Details & 46 images. Includes a Virtual Tour

$1,300,000 $460 per sq.ft. Killington VT Home »


Price Change! Reduced by $200,000 down 15% on April 29th 2026
5 Beds | 4 Baths |   Total Sq. Ft. 3640  |  Acres: 2.11
Listed on Friday Sep 5, 2025
Description: This stunning Coventry Log Home, situated on 2.11 acres, is a true gem for outdoor enthusiasts and those seeking a peaceful mountain escape year-round. An added bonus is the ancillary unit with a separate entrance located over the garage. Savor breathtaking views of both Pico and Deer's Leap mountains. The elevated balcony deck is the perfect spot to enjoy a winter evening watching the snow cats meticulously groom the slopes for the next day of skiing. This meticulously crafted home is built by Coventry Log Homes, a company known for its quality and use of kiln-dried Eastern White Pine, ensuring a durable, long-lasting structure that stands up to Vermont's variable climate. The home is topped with a 24-gauge standing seam metal roof--a top-of-the-line choice for mountain homes that is resistant to heavy snow loads and high winds, requiring minimal maintenance. Just moments from Killington Resort, famously known as the "Beast of the East" for skiing and snowboarding, the Killington area also offers a wealth of year-round activities including mountain biking, hiking the Appalachian Trail, golfing, and a vibrant nightlife with numerous restaurants and bars. This is more than just a home; it's a gateway to an unparalleled mountain lifestyle, combining rustic elegance with modern amenities and an unbeatable location. It's a perfect family getaway or a primary residence for those who live and breathe the outdoors. Open House 4/25 11-1 See Listing Details & 55 images.

$1,495,000 $559 per sq.ft. Killington VT Home »


Price Change! Reduced by $30,000 down 2% on April 27th 2026
4 Beds | 5 Baths |   Total Sq. Ft. 4002  |  Acres: 1.1
Listed on Tuesday Feb 10, 2026
Description: The Queen's Croft--A Luxurious 4-Bedroom, 5-Bath Custom Vacation Home less than 2 miles to Bear Mountain. Built in 2007 and spanning three beautifully finished levels, this fully furnished and equipped 4,000 sq ft custom home offers the ideal blend of luxury, comfort, and convenience. The property features many thoughtfully designed rooms, and high quality details like heavily-insulated 2x6 construction, 12-inch on center deck framing, and 200 amp electrical service. Private Setting & Exceptional Outdoor Living located on peaceful, wooded, 1.1 acre lot, the home features a large deck for outdoor dining and relaxation, plus a private hot tub for unwinding after a day on the mountain. Ample parking ensures easy access for owners and guests alike. Designed for Mountain Living. Both the upper and lower entryways offer exceptional storage solutions, with the lower foyer offering storage for skis and boards, as well as a custom drying rack for wet boots and gear--keeping everything organized and ready for your next adventure. A striking stone, wood-burning fireplace anchors the main living area, creating a warm and inviting gathering space. Spacious & Fully Appointed. With four bedrooms and five bathrooms across three levels, the layout provides comfort and privacy for groups of all sizes, and the spacious chef's kitchen is perfectly appointed for feeding a hungry crowd. The home comes fully furnished and turnkey, allowing you to step right into the mountain lifestyle without lifting a finger. Strong Rental History. This property has an established rental track record, making it an excellent option for buyers seeking both personal enjoyment and investment potential. Don't miss this rare opportunity to own a luxurious, well maintained mountain retreat in one of Killington's most desirable locations. Ready for immediate enjoyment and income generation, call today to schedule a private showing. See Listing Details & 59 images.

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