71 properties for sale in West Jamaica

Welcome to 6 Jamie Lane, a private Vermont getaway tucked into the hills of Winhall, just minutes from Stratton Mountain. Set on 1.4 acres, this three bedroom home offers the space, setting, and comfort to enjoy every season in Southern Vermont. The main living area features a bright two story great room with a floor to ceiling fieldstone fireplace, warm wood details, and sliders that open to a wrap around deck. The kitchen and dining areas connect easily to the living space, creating a natural flow for meals, relaxing by the fire, and time at home after a day on the mountain. The main level includes a bedroom with a private en suite bath, while the second floor offers two additional bedrooms with a shared full bath. The finished lower level adds a second living area with another wood burning fireplace and a game room along with a private office or den, laundry area, and three quarter bath. Outside, enjoy the peaceful wooded setting, deck, hot tub, gravel driveway, and standby generato

Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter shuttle service to Stratton. Inside, natural wood, exposed beams and a brick fireplace create the warmth of a classic Vermont retreat. The updated kitchen opens to the dining area, while multiple living spaces provide room for family and friends. The expansive four season sunroom is a highlight, with a vaulted ceiling and walls of glass overlooking the surrounding woods. An additional office or den offers flexibility, and the attached one car garage adds everyday convenience. Late summer means days at the pond and evenings around the firepit. Fall brings hiking, foliage and cool evenings by the fire. When winter arrives, Strattonwald's shuttle makes sk

Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game rooms, bar, 2 fireplaces and outdoor patio. Interesting architectural features with curved staircase, high ceilings, and light filled spaces. The gourmet kitchen opens to a grand dining room where you can host large dinners on winter weekends and holidays and during those summer golf and hiking excursions. Well designed for large groups, multiple or extended families with 6 bedrooms, 5.5 baths. Custom ski room, attached garage, and Stratton Resort winter shuttle that picks you up at your driveway and delivers you to the Base and Village. Enjoy the use of the Stratton Sports Center and Stratton

4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a class

Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retreat, privately set on a secluded 1-acre lot surrounded by woods and nature. Tucked away in a peaceful setting, this inviting home offers warmth, character, and the simple beauty of country living. The first floor features an open floor plan with hardwood floors and natural woodwork throughout, a cozy livingroom with a beautiful fireplace, a small den leading to a bedroom with a knotty pine ceiling, plus a spacious rebuilt (2018) 400 sqft. Primary bedroom with wide pine floors, laundry, ample closet/storage space, and a wood stove perfect for snowy Vermont evenings. Upstairs, you'll find a third bedroom and an additional bonus room for guests, office space, or hobbies. Step outside onto the large deck, built in 2022, and take in the summer breezes and colorful fall foliage while surrounded by the peaceful beauty of rural Vermont. A loose-laid stone wall elegantly frames the garden and established pl

Ready for its next stewards, this cozy home has been cherished by the same family for many years and is set on 10 acres of open land and woodlands. Enjoy a peaceful rural setting conveniently located between two of southern Vermont's premier ski destinations: Stratton Mountain Resort and Mount Snow. At the heart of the house is an inviting kitchen featuring updated cabinets, soapstone countertops, and wood cookstove. The first floor includes a small bedroom, and living room, with two additional bedrooms and a full bath upstairs. A spacious family room leads to large deck overlooking the serene surroundings. An oversized garage provides generous workspace and storage above. Whether you are an outdoor enthusiast seeking a primary residence or a vacation retreat, this welcoming property offers comfort, character, and access to year-round recreation. Sale is subject to final subdivision approval; the family will retain the surrounding land

Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (2025), hot tub, barrel sauna, Level 2 EV charger and rooftop solar. Open great room with stone wood-burning fireplace and indoor swing, open kitchen and dining, walkout lower level with wet bar and arcade, 4 bedrooms and 4.5 baths. One of the only private heated-pool rentals near Stratton, and it earns like it: $155,716 gross in 2025 and $216,999 trailing 12 months; about $102,000 in confirmed future bookings on the books (9 stays). GOLF-COURSE ESTATE OPPORTUNITY: the seller also owns the adjoining Indian Paint Brush building lots (Lots E-13R and E-14R, 2.48+/- ac), which abut the Stratton golf course and are listed separately at $500,000. Buy both: live in or rent the Moose while you build your estate next door. Featured on the Destination Channel's Staycation TV program. Listing broker i

First Chair Lair: a proven, turnkey Stratton rental on High Meadow, on the complimentary winter-weekend Stratton shuttle route and about 5 minutes to the base. Two-story great room with brick wood-burning fireplace and cathedral pine ceilings, renovated 2024-25 kitchen and baths, dining for 12, private hot-tub deck, and a lower-level game room (pool table, arcade, darts, foosball). Five bedrooms including a king suite with soaking tub, a fireplace queen, and a bunk room; 4 full baths; 2-car garage; town water and sewer. INCOME: $158,731 gross in 2025; $147,057 trailing 12 months; about $115,000 in confirmed future bookings on the books (11 stays, including long winter stays). Currently marketed for 8 guests; capacity can increase to 12 with a fire-alarm system upgrade (quote on file). Sold fully furnished with bookings, website presence and optional continued professional management by 42 North. Listing broker is a principal and beneficial owner of the selling entity. Potential tax adv

Attention Buyers looking for a Turn Key property and or business location: Proven Short Term Rental Income, 142k gross over the past 8 years with 2 of those years virtually closed due to COVID. 135k net. Being on Route 100 gives you easy access to everything including Commercial and Mixed Use prime location. Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you'll find soaring cathedral ceilings in the living room, abundant natural light, a cozy brick hearth with wood stove, and an inviting open kitchen and dining area perfect for gathering with family and friends. This main floor also has a full bathroom. The 3 bedrooms and another full bath are upstairs. Step back outside to a spacious deck fea

Exceptional Offering and Value Located in Stratton Resort's sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent renovations include updates to the kitchen and carpeting, creating a move-in ready retreat for all seasons. A spacious wraparound deck with hot tub provides the ideal setting to relax after a day on the slopes. The separate family room, complete with an adjacent full bath, offers excellent flexibility and can easily serve as additional sleeping space for guests. Additional highlights include an attached two-car garage and shuttle service access to Stratton's ski slopes, winter activities, Stratton Village, shopping, and dining. Active Stratton Sport Center Bond. Water a

New Price; $349,000! Exceptional Southern Vermont Value Near Mount Snow and Stratton. A rare opportunity to own a classic Vermont home in a beautiful hilltop setting at an exceptional new price. Originally offered at $495,000, this property is now available for $349,000, offering buyers an outstanding opportunity to own a home in one of Southern Vermont's most desirable four-season locations. Set atop a peaceful New England hill, the property enjoys beautiful local and mountain views and is ideally located just six miles from Mount Snow, Stratton Mountain, Grout Pond, and access to the VAST snowmobile trail network. Skiing, hiking, boating, snowmobiling, and other four-season recreation are all close at hand. Filled with natural light, the home features warm wood floors, large windows that capture the surrounding scenery, and a spacious 15' x 24' patio overlooking the private backyard, an inviting spot for relaxing or entertaining. Thoughtful improvements provide modern comfort while r

Charming cabin just outside the village of Wardsboro in Southern Vermont. This home away from home is being offered for sale for the first time by the original owners that built it. Up a private drive with easy access off a paved road sits this rustic retreat, overlooking a river and short range mountain view across the way. The home has a large open concept living space with the exposed log joinery throughout, an updated kitchen and spacious dining area, stone fireplace and hearth, full bath and laundry, 4 upstairs woodsy guest bedrooms, a large covered porch as well as a screened in porch area, walkway to a private gazebo for further outdoor enjoyment, additional owners storage shed, 2 car detached garage with workshop, wood shed, and more. The septic was recently updated. A tremendous opportunity for someone looking for a home with easy access but not a lot of space to maintain

Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views. Just minutes to Stratton Mountain'sTrails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room, defined by cathedral ceilings, wood burning stone hearth and expansive windows, showcases breathtaking views and the natural beauty of the Green Mountains.Every detail showcases a design with performance and comfort in mind:Premium lighting, hardware and plumbing fixtures, exceptional wood flooring and tile baths. A gourmet kitchen with Bosch appliances and a separate scullery offers a design well suited for entertaining and apres ski gatherings. Three levels, 4 Bedrooms/3.5 Bathswith 2 ensuite primaries, a lower level with a mega bedroom designed with bunks in mind,a spacious game and media room that opens to the outdoors- just ready foryour active lifestyle.With the mountain e

Stratton Mountain Club AVAILABLE to the purchaser of this exceptional Stratton Resort Residence in High Meadow! This home's design and fit and finish creates the mountain ambiance you look for:Commanding Riverstone Fireplace, Wood accents, Cathedral Ceilings, Wide Pine Floors, an open floorplan with Gourmet Stainless Steel Kitchen and Dining. A lower level family room and game room with 2nd fireplace and entertaining space. Whether it's gathering with friends for apres ski after a day on the slopes or cozying up with family around the fireplaces, you'll experience the lifestyle you look for in a year round retreat. Four Bedrooms/4.5 baths with multiple suites on three levels offers privacy and spacious accommodation. Pull into your oversized heated garage with mudroom entry. Situated on a one acre lot to take in an abundance of sunlight and winter views. Beautifully maintained and turnkey.Resort shuttle stops at your driveway, sports center bond available. All the amenities of the reso

Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton's most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge or simply hop on the convenient shuttle for effortless access to the slopes, this property offers the best of Stratton living in every season. Step inside to find a spacious, light filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day on the mountain. With four well-appointed bedrooms, this home comfortably accommodates guests and offers flexible space for work, play, or quiet retreat. Outside, the expansive 1.37-acre lot delivers the privacy and peaceful surroundings you expect from a mountain home, including a covered deck with a hot tub and gri

Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort, the location offers easy access to the mountain, local favorites, and the best of southern Vermont living. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while radiant heat on all three levels adds warmth and comfort throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to

New Price; $349,000! Exceptional Southern Vermont Value Near Mount Snow and Stratton. A rare opportunity to own a classic Vermont home in a beautiful hilltop setting at an exceptional new price. Originally offered at $495,000, this property is now available for $349,000, offering buyers an outstanding opportunity to own a home in one of Southern Vermont's most desirable four-season locations. Set atop a peaceful New England hill, the property enjoys beautiful local and mountain views and is ideally located just six miles from Mount Snow, Stratton Mountain, Grout Pond, and access to the VAST snowmobile trail network. Skiing, hiking, boating, snowmobiling, and other four-season recreation are all close at hand. Filled with natural light, the home features warm wood floors, large windows that capture the surrounding scenery, and a spacious 15' x 24' patio overlooking the private backyard, an inviting spot for relaxing or entertaining. Thoughtful improvements provide modern comfort while r

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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

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

A true Vermont lodge in every sense-warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who return to experience this special home year after year. Inside, the expansive open-concept living areas were made for gathering after a day on the mountain, while thoughtfully designed private spaces allow everyone room to relax and recharge. Curl up beside one of two fireplaces as the snow falls outside, host movie nights in the impressive 11-foot home theater, or gather in the great room around the 90-inch TV for game day. The lodge experience continues outdoors, where four-season entertaining takes center stage. Grill and dine beneath the stars, soak in the six-person hot tub, unwind in the eigh

Located just one mile from Stratton's Base Lodge and Village, this 4-bedroom, 3-bath end-unit Styles Brook townhome offers the perfect combination of convenience, comfort, and year-round mountain living. Spanning three levels, Unit 501 enjoys the added privacy, extra windows, and abundant natural light that come with end-unit ownership. The main level is designed for gathering, featuring beautiful hickory floors, a wood-burning fireplace, a functional mudroom, powder room, and access to an expanded deck overlooking a peaceful wooded setting. Whether you're returning from a powder day, hosting friends for a golf weekend, or simply enjoying a quiet escape in the mountains, the spaces are designed to be enjoyed in every season. The Styles Brook association allows owners to add hot tubs to the deck, with required reinforcement, offering you the opportunity to create the ultimate apres-ski retreat. Upstairs, the spacious primary suite features vaulted ceilings, excellent natural light, a we

Unmatched Comfort and Convenience at Stratton's Ober Tal - trailside property Discover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Next to the Tamarack ski lift, you'll enjoy unbeatable access to the slopes and all the amenities in Stratton Village. Close enough to swing back for a quick lunch, this condo lets you make the most of your mountain time. After a day on the mountain, unwind by the wood-burning fireplace in the family room, or gather for meals in the large dining area, featuring a second wood-burning fireplace. Step outside to relax on the oversized deck with distant views of Bromley Mountain. Designed for entertaining, the spacious chef's kitchen is well-equipped for group cooking, with thoughtful amenities like double ovens, a microwave, two dishwashers, a prep sink, and a wine fridge. Gather around the long granite island with seating for five, where everyone can join in the fun or simply relax while dinner is prepare

Location, luxury, and the best of Stratton Mountain living! Just steps down to Stratton Village or up to the Wanderer ski trail, this exceptional mountain retreat offers convenience, privacy, and timeless Vermont charm. Extensively updated, the home showcases beautiful craftsmanship, soaring ceilings, exposed reclaimed timber beams, and a dramatic floor-to-ceiling stone fireplace anchoring the impressive great room. Expansive windows invite natural light throughout the day, while warm hickory floors create an atmosphere that is both elegant and comfortable. Adjacent to the custom kitchen is the stunning dining area, with its vaulted wood ceiling and walls of windows. Radiant heated floors, central air conditioning and a heated two car garage ensure year round comfort. Major improvements include a complete exterior renovation, and an expansive new deck offering generous space for outdoor entertaining with a hot tub for apres ski. In addition to five bedrooms, the thoughtfully designed i

Incredible combination of location and amenities. Walk across the street to the ski slopes and Stratton Village with its shops, restaurants, and year-round activities. This top-floor condominium features soaring ceilings, abundant natural light, and a desirable two-bedroom, two-bath layout. Long Trail offers a year-round heated outdoor pool, hot tubs, and a sauna. Heated underground parking, ski lockers, and private storage cages make mountain living simple and so convenient. Seller is listing broker

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you'll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect apres-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermon

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20-25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space. For added transparency and peace of mind, the seller has completed a pre-listing property inspe

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

Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a private loft complete with its own 3/4 bath. There is plenty of room to relax after a day on the trails, or you can step down into the sunken hot tub on the recently updated deck. Leave the keys behind, its exceptional location offers easy walking access to village shops, dining, and the in-ground pool for the ultimate hassle-free mountain getaway

Embrace the ultimate Stratton lifestyle in this turnkey, one-level 2BR/2BA condo designed for effortless mountain access. Located just moments from the Village and the Stratton training center, this home eliminates the logistics and maximizes the fun with a dedicated gear-ready mudroom and a complimentary shuttle that whisks you straight to the lifts. The interior features a bright, open-concept floor plan anchored by a classic wood-burning fireplace, while the kitchen's breakfast bar serves as the perfect hub for morning coffee or apres-ski snacks. Whether you're relaxing in the spacious primary ensuite, hosting on the private deck, or enjoying the community pool and BBQ area in the summer, this residence is the perfect four-season basecamp. Your Vermont story starts here