Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside, you’ll find an open-concept kitchen, dining, and living area that flows effortlessly onto a large deck—ideal for hosting gatherings or enjoying the quiet outdoors. Two oversized primary suites with private ensuites provide luxurious comfort for guests or multigenerational living. A standout feature is the expansive bonus room, currently outfitted as a professional recording studio with soundproofing—ideal for musicians, podcasters, or anyone in need of a creative or quiet workspace. Step outside to a private, tree-lined backyard with multiple decks perfect for relaxing or entertaining. A two-car garage adds convenience, while the whole-house Tesla battery ensures seamless comfort and peace of mind year-round. Whether you're entertaining a crowd or enjoying a peaceful evening at home, this one-of-a-kind Chester retreat offers space, versatility, and thoughtful features throughout. A wonderful value as a primary home or as a vacation home 2 families could share and still have privacy.
This is a neat spot. Close enough to the village that you can walk to shops and restaurants but just far enough out that you enjoy the peace and quiet of a dead-end road. The house sits up from the road which means that you get to enjoy some views of Okemo. If you would rather not drive up to the mountain, you can walk to the end of the street and hop on Okemo's shuttle. Built in 1993, this home offers living space on three levels. You walk into a small mudroom where you can leave your coats and boots. Then, into the large family room with space for TV, games or exercise all of which gets to take in the view. Also on this level, there is a bonus room...work from home, no problem! The full bath rounds out the lower level. Up a flight to the kitchen which is open to the large living room with brick fireplace and sliders to the wrap around deck. Two bedrooms and another full bath on this level. Up again to the primary bedroom where you would enjoy sliders, a small balcony and a view of the mountain as soon as you open your eyes in the morning. Very large bath with stall shower for the primary bedroom. There is an oversized two car garage. There are several updates in the past couple of years...new siding, sliders, roof and deck. Come have a look to see if this is what you have been waiting for!
Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide air conditioning and reliable climate control, while neutral furnishings create a welcoming, comfortable vibe. Full compliance with the current fire and safety regulations, including a modern sprinkler system, provides security and rental readiness. SouthFace Village offers direct access to nearly 200 acres of private property for year-round recreation. Hike or bike Okemo's trails in the summer, and in the winter, step outside and hop on the Sunshine chairlift. Owners also enjoy access to a private pool and fitness center, perfect for relaxing after a day of adventure. If you're looking for the ideal retreat in the heart of Vermont's four-season playground, this condominium may be the perfect fit.
Affordable Okemo Trailside 3 bedroom plus den end unit. In great condition and ready to be your ski get-a-way this season. Updates include kitchen, main level bathroom and a brand new wood burning fireplace installed in the Fall of 2025. On 2 levels, there is an open kitchen/dining/living area, bath and bedroom on the main level, 2 bedrooms, bath, laundry and a cozy den finish the lower level. The condo is nicely furnished, just walk in, light the fire and pour yourself a glass apres ski, for a warm relaxing evening. Walk to the Sachem Trail to enjoy the trails, and walk back for your down time. Trailside has a summer pool and tennis courts to get you here in the Summer months.
Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views. The modern kitchen is equipped with stainless steel appliances with views to the mountain and living/dining area, making it both functional and inviting. The spacious primary suite includes 2 queen sized beds, generous closet space and an en-suite bath with a soaking tub. A second full bathroom adds flexibility for guests along with a Murphy bed, being able to sleep 8 with the sofa bed. Enjoy full access to resort-style amenities including an indoor & outdoor heated pools, hot tubs, fitness center, ski lockers, underground heated parking and a 24-hour front desk. Dining, shopping and year round recreation are just steps away - skiing, snowboarding, hiking are all at your doorstep. Whether you're seeking a weekend escape, an income-generating property or a full-time mountain home, this condo offers it all in one unbeatable location. Turnkey and ready for your next adventure - Schedule your showing today!
Welcome to Okemo's iconic roundhouse. While not completely round, this distinctive home is only about 1,200' from the main base area - an easy walk even in ski boots. It is all about location! You will find 3+ bedrooms, 2 full baths, a sauna, and hardwood floors in the common areas. The wrap-around deck provides views of Okemo ski trails and is great for outdoor entertaining. The mudroom has a slate floor and lots of space to keep your snow gear. The bonus room has a pellet stove and can be your second living room. The main living room has a gas fireplace/stove that adds ambiance to the home along with the great natural light from the windows. The kitchen has a lot of cabinetry and the dining area flows from the kitchen to the living room. The lower bath offers a large whirlpool tub and a sauna for relaxing after a day on the mountain. Come see one of the most affordable houses that is this close to the trails. Visit the Okemo real estate community today. Taxes are based on the current town assessment.
The Castle Hill Resort & Spa is your place to enjoy and relax. Top floor end unit has 2 levels of living spaces. There are three spacious bedrooms, 3.5 baths, a second level loft area (den) and a lock out area with a bedroom, 3/4 bath and den that can be rented out if you choose. Cathedral ceilings, air conditioning, gas fireplace with an open kitchen/dining/living room. A private main level primary bedroom with a walk in closet and full bath creates a calm atmosphere away from the other bedrooms. The amenities at Castle Hill Resort include an outdoor heated pool, hot tub and tennis courts. Additionally there is an Aveda Spa with a fitness center and massage and facial rooms. Located minutes from Okemo Mountain, Ludlow village and restaurants and a beautiful golf course.
Enjoy big Okemo views from this charming three-bedroom, two-bath home tucked on a quiet dead-end street just minutes from Okemo Mountain and downtown Ludlow. A spacious mudroom welcomes you inside — perfect for storing skis and gear after a day on the slopes. The bright and inviting living room features large windows that fill the space with natural light and a wood-burning fireplace for cozy winter evenings. Step out onto the expansive deck with a hot tub and take in sweeping views of Okemo and the surrounding mountains. Whether you’re looking for a comfortable year-round home or a vacation getaway, this property offers the ideal blend of privacy, convenience, and Vermont charm. Visit the Okemo real estate community today. Taxes are based on current town assessment.
Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless glass showers. The building has all new siding, decks, windows and doors, ensuring years of headache free usage. Current special assessments are paid. Make this your 4 season happy place while skiing/boarding inn the winter months and enjoy the tennis courts and heated outdoor pool in the summer months.
Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline. Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and include a spacious eat-in kitchen, full bathroom, partial concrete basement, replacement windows, and a recently installed oil tank. The detached one-car garage provides convenient storage for your kayaks, paddleboards, and other lake toys. This property offers a spectacular location less than two miles from Okemo Mountain. Whether you’re roasting marshmallows by a lakeside campfire in summer or playing board games by the warmth of the stove on a snowy day, this home invites year-round enjoyment. Importantly, the home was unaffected by recent flooding and comes with an elevation certificate confirming it lies outside the flood plain. This property is being offered "AS IS".
Welcome to this charming home nestled in a small neighborhood along the scenic Black River in Cavendish, Vermont. This inviting property combines classic Vermont character with versatile living spaces, all within walking distance of the town green, shops, restaurants, and more. Step inside through the mudroom. The kitchen offers a warm, welcoming space with a sunny dining area perfect for morning coffee or casual meals. A formal dining room provides space for larger gatherings, while the living room, bathed in morning light, creates a cozy setting to relax and unwind. A first-floor bedroom adds convenience and flexibility for guests or main-level living. Upstairs, you’ll find three additional bedrooms and a full bathroom, providing plenty of room for family or friends. The property also includes an attached two-car garage and a studio apartment — ideal for guests, rental income, or a private home office. The studio features a full kitchen and dining area, a full bathroom, and a comfortable sleeping space. Enjoy life along the river with easy access to outdoor recreation, and the charm of a small Vermont village right outside your door. This Cavendish home is a wonderful opportunity to experience the best of Vermont living — convenient, comfortable, and full of character. Visit the Okemo real estate community today. Taxes are based on current town assessment.
Nestled on a quaint hillside in the Okemo Valley, the Castle Hill Resort offers an abundance of amenities with ownership in the resort community. This rare two-bedroom condominium provides ample space for everyone with extra windows for light and views. This is rare as most buildings are Quad-plexes and this building is a top and bottom Duplex, sharing no walls with neighbors! Enjoy an on-suite with privacy, and an additional bedroom along with a sitting room/den for separation. Ground level living with a private back deck for seasonal enjoyment. Take advantage of luxury resort amenities including two tennis courts, a year-round heated outdoor saltwater pool and hot tub, and a full-service Aveda Health Spa and fitness center. The Castle Inn Restaurant is also conveniently located within the resort complex. Visit the Okemo real estate community today. Taxes are based on current town assessment.
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