Properties Near 1247 Cole Pond Road Jamaica, VT

Get ready for ski season! Plenty of space for the whole family. Set up for fun with two living rooms, a hot tub and barrel sauna. Great rental history. Owner is Listing Broker.

Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort. Just minutes from Stratton Mountain, with winter weekend shuttle service right from your doorstep, this property ensures effortless access to all your outdoor adventures. Inside, you'll be greeted by a spacious living room with a striking fireplace, ideal for cozying up after a day on the slopes. The large primary suite offers a private sanctuary, and the inviting 3-season porch lets you savor the beauty of each season. Strattonwald residents also enjoy exclusive private beach and pond access, as well as tennis and pickelball courts in the summer. With Bromley and Magic Mountains nearby and the shops and restaurants of Manchester just a short drive away, this home is perfectly located for all your mountain and recreational pursuits. Experience the charm, comfort, and convenience of 73 Cranberry Hill Road—where every season offers a new story.

A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great for ice skating and hockey), a private dock, four bedrooms, three bathrooms, a great room, living room, music room, eat-in kitchen, screened in dining porch, large deck, over-sized second floor office/gym/playroom, 2-car garage and large shed. All this and sunset views over the mountain, two cherry trees, blueberries and wild blackberries. New roof in 2021.

Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse!  Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and desires.  Close to world renowned downhill skiing at Stratton, Mount Snow, Magic, Okemo & Cross Country Skiing at Viking, Grafton Outdoor Center, Wild Wings.  PLUS hiking, canoeing, outdoor life along with arts, festivals & great culinary options. Beautiful Manchester Vermont is 20 minutes away. Fabulous back yard sliding hill and plenty of land to play on, close to everything AND an expansive interior with a large addition. Walk through the WIDE entry door into the big mud room with loads of storage then into the kitchen with large peninsula, living room and kitchen / dining room.  Over to the butler’s kitchen and huge (full of windows) living/dining/playing rooms complete with beautiful hearth and chimney.  MORE space downstairs with a bedroom/bath/2nd family room and then upstairs to a sweepingly large primary with bath and 4 other bedrooms with 2 other bathrooms, still yet another play area.  This homestead is a generational gem awaiting its next Stewart.

Enjoy one of the most stunning, unobstructed views of Stratton Mountain and its slopes from this beautifully maintained 5-bedroom, 3-bath home, located on a quiet dead-end road just 3 miles from the lifts. This inviting retreat features a completely renovated kitchen, a new furnace, and comes fully furnished for turnkey enjoyment. Air conditioning throughout ensures comfort year-round—perfect for enjoying all that Vermont has to offer in every season. Outdoor living is a highlight, with a gorgeous screened-in porch and three decks—two recently upgraded with Trex decking—ideal for relaxing or entertaining while taking in the breathtaking scenery. Whether you're seeking a mountain getaway or a spacious year-round residence, this home offers comfort, style, and unbeatable proximity to Stratton’s slopes and outdoor adventures.

Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly evenings. Cathedral ceilings soar, enhancing the spacious feel. The primary suite is a true sanctuary, boasting a spa-like bathroom with double sinks, a jetted tub, a separate shower, and an expansive walk-in closet. Enjoy private balconies directly from your bedroom, offering stunning vistas and a tranquil spot for morning coffee or evening stargazing. Beyond the living areas, this home offers an array of desirable amenities including a stylish bar, ideal for gatherings, and a dedicated exercise room to maintain your wellness routine. Strategically located, this property offers unparalleled access to outdoor adventures. Just minutes from Stratton Resort, you'll enjoy world-class skiing in winter and championship golf in the warmer months. Experience the best of Vermont living with a perfect blend of luxury, comfort, and convenience. Your Winhall dream home awaits!

This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just off the deck. Automated whole house generator installed in 2020. Updated kitchen, bathroom, and flooring in 2025. See the recent renovation list. Owner is Vermont licensed real estate agent.

Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s closet—ideal for all your gear. Turnkey and move-in ready, this is the perfect mountain retreat in one of Stratton’s most desirable communities!