Properties Near 97 Okemo Trailside Extension Ludlow, VT

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Excellent value priced to sell - Prime location, ski-on, ski-off with direct access to Sachem Trail, with just a few steps from your door, and you'll be on the slopes! This is a bright and sunny condo featuring 3 bedrooms, 2.5 bathrooms, and a loft. The living and dining area features a cathedral ceiling, a wood-burning fireplace, and a deck offering a long-distance view. Recent updates include kitchen appliances and countertops. Enjoy this end unit with 3 levels of living space with no one living above or below you. Just minutes away from the Fox Run Golf course, a championship 18-hole course. The Okemo Trailside community features a heated swimming pool and two tennis courts for your summertime enjoyment. Guest comments include "could not beat the location for a ski weekend. We were just steps to Sachem Trail. It easily accommodated 2 families," and "just can't beat skiing home for a quick lunch and hoping right back on the trails!"
This nicely updated 3 bedroom plus family room townhome has stunning views to the east in a mid- mountain setting. Enjoy the large updated kitchen with wood cabinetry, stone countertops, and wood crafted breakfast bar. The open living area with cathedral ceiling centered by a woodburning fireplace, leads out to a covered deck and hot tub offering spectacular mountain views. The private primary bedroom suite includes an updated bath with stone countertop and custom-built cabinetry. Two additional bedrooms plus family room occupy the ground level with an updated bath accented by tile floor and stone counters, cedar sauna, and laundry room. Other updates include sliders and lighting. The entry mudroom offers built-ins and leads out to two ski closets. A private on-demand shuttle takes you to and from the Okemo's Sachem ski trail in a matter of minutes without the fuss of having to walk to the slopes.
Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy from the road with an emphasis on light and views to the south. Enter the oversized one-car garage with tremendous storage space for your skis, bikes, fishing poles, and more. Warm up by the inviting wood-burning fireplace after a day on the slopes or gather with friends and family in the open-concept living and dining area. With four generously sized bedrooms and ample bathrooms, there's room for everyone to spread out and unwind. Three of the bedrooms and two baths occupy the top floor, along with an office off the primary bedroom. The lower level features a large game room along with a bedroom and full bath. There is also extra sewer capacity for future expansion possibilities. The front lawn is level and features a stone retaining wall, perennials, and ample room for entertaining. Located near Ludlow village, you are close to excellent dining, shopping, and all the amenities this vibrant mountain town has to offer. Whether you are looking for a vacation getaway or a full-time residence, this home offers the quintessential Vermont lifestyle in an unbeatable location.
Winterplace at Okemo - Mountain Lifestyle at Winterplace L101. Discover one of Okemo’s most sought-after locations with this rare end-unit home. Positioned for maximum privacy and ease, this 3-bedroom residence is a short walk from the trail, putting the entire mountain at your doorstep. The ground-floor layout offers a spacious great room where the kitchen, dining, and living areas meet, creating an ideal hub for entertaining. After a day on the slopes, warm up by the wood-burning fireplace or take a short stroll to the top-notch Winterplace recreation center to enjoy the indoor pool and hot tubs. Whether it’s winter skiing or summer tennis and BBQing, L101 offers the very best of resort living. Visit the Okemo real estate community today. Taxes are based on current town assessment.
Sitting atop the Okemo Trailside community just below the Catnap ski trail and abutting the Okemo State Forest. Three bedroom plus family room townhome offering magnificent panoramic mountain views to the east. Large and well equipped kitchen with vaulted ceiling and breakfast bar. Open dining and living areas centered by a woodburning fireplace with cathedral ceilings leading out to a large covered deck. Private owners suite with skylit whirlpool tub. Two guest bedrooms with full bath and sauna. Separate family room. Two private ski lockers. On demand shuttle service to the Sachem ski trail. Summer amenities include swimming pool and tennis courts. Hiking right outside your door. Wonderful year round retreat.
Two Unique Homes on 16.5 Acres Near Okemo Mountain Resort and Other Outdoor Recreation Opportunities! Discover an exceptional Vermont retreat just 10 minutes from Okemo Mountain Resort—featuring two distinctive homes on 16.5 private acres in Mount Holly. Surrounded by forest, open meadows, and a peaceful stream, this property offers the perfect mix of natural beauty and year-round adventure. The main home exudes Vermont charm with natural wood interiors, exposed beams, and a striking stone fireplace. With 3 bedrooms and 2 full baths, it features a granite kitchen, open living area, and large deck ideal for soaking in mountain views. A new heat pump forced-air system adds modern efficiency, and the home is offered fully furnished for a turnkey move-in. The newly finished guesthouse, once a garage, is now a modern 1-bedroom, 2-bath residence with spacious living areas, a kitchen, dining space, and raised deck. Unfurnished and ready for your vision, it’s perfect as a rental, guest suite, or creative retreat. Enjoy access to nearby snowmobile trails, hiking paths, and all-season recreation—just minutes from Okemo’s ski slopes. Whether you live in one home and rent the other or create your own Vermont sanctuary, this rare Mount Holly property combines comfort, flexibility, and an unbeatable location.
Winterplace on Okemo Mountain. Embrace the ultimate Okemo Mountain lifestyle in this bright and inviting Winterplace F301 2-bedroom, 2-bathroom corner unit. Bathed in natural sunlight, the open living space seamlessly connects the dining area, full kitchen, and a cozy wood-burning fireplace—perfect for après-ski relaxation or entertaining friends and family. A convenient 3/4 bathroom off the living area adds functionality for guests. Two bedrooms share a Jack-and-Jill bathroom, providing privacy and comfort for family or friends. Step outside your door to enjoy true trailside living, with direct access to the slopes and the entire mountain at your fingertips. Winterplace offers exceptional amenities, including a heated indoor pool, hot tubs, a fire pit, and tennis courts, making every season enjoyable. Whether you're hitting the slopes, lounging by the fire, or taking a dip after a day on the trails, this condo is the perfect year-round retreat at Okemo. Visit the Okemo real estate community today. Taxes are based on current town assessment.
Winterplace at Okemo—where location truly makes all the difference. A104 is perfectly positioned on a coveted corner location, directly across from the resort amenities, including the indoor pool, hot tubs, and tennis courts. Step outside and enjoy effortless access to everything Okemo has to offer, a short distance away. You’ll be clicking into your skis and heading straight to the Sunburst Six, always skiing toward the top of Okemo. This fully renovated residence has been thoughtfully updated to provide comfort, style, and functionality for year-round enjoyment. Designed to accommodate your entire family and guests, the home provides a warm and inviting retreat after a day on the slopes, trails, or golf course. Whether you’re enjoying winter ski weekends, summer mountain activities, or quiet off-season escapes, this property delivers the ultimate four-season lifestyle. With unbeatable proximity to amenities, slopeside convenience, and modern updates throughout, A104 at Winterplace is an exceptional opportunity to own in one of Okemo’s most desirable communities. Schedule your showing today and experience firsthand why this location is second to none. Visit the Okemo real estate community today. Taxes are based on the current town assessment.
Discover the perfect balance of comfort, convenience, and stunning valley views in this beautifully appointed 2-bedroom, 3-bathroom residence located in the sought-after Bixby House at Jackson Gore, Okemo Mountain Resort. This spacious and well-designed unit offers an exceptional slopeside experience with direct ski access and all the amenities you need for a relaxing, four-season Vermont getaway. Enjoy a cozy, open-concept living and dining area with a gas fireplace, fully equipped kitchen, and large windows that frame sweeping views of the valley. Each bedroom is generously sized, and the unit includes three full baths for maximum privacy and comfort. The layout is ideal for families, couples, or rental guests, with a flexible floor plan and quality finishes throughout. Amenities include an onsite owners lounge, business center, private underground heated parking access to the Spring House fitness center, heated indoor and outdoor pools, slopeside hot tub and summer tennis. The unit sleeps 8 and is pet friendly.
Direct ski-on, ski-off two-bedroom top-floor unit in the Kettlebrook community. Nicely updated throughout. Enclosed mudroom entrance with built-ins, laundry, and exterior ski closet. The main level includes a well-designed kitchen and a separate dining area with a newly installed slider leading out to the deck, which looks out to the slopes; a living room with a wood burning fireplace and cathedral ceiling; and a guest bedroom with a full bath. Kitchen upgrades include wood cabinetry and floors, stainless steel appliances, and stone counters. A private primary bedroom suite with wood cabinetry, stone counters, and an oversized glass shower occupies the entire second floor. Updated baseboard heating system throughout. Enjoy one of the best locations in this Okemo slopeside community.
This beautifully located 2-bedroom, 2.5-bath condominium offers true ski-in/ski-out living, nestled directly slopeside among the Sidewinder, Promenade, and Rising Star ski trails on Okemo Mountain in Ludlow, Vermont. An easterly orientation fills the home with soft morning light, showcasing warm sunrises and picturesque winter views. The living room features a wood-burning fireplace and opens via a sliding glass door to the deck and front yard. This is an ideal set up for dog owners, children at play, or simply relaxing outdoors with a glass of wine on a sunny March and watch the action on the slopes The kitchen and bathrooms are thoughtfully appointed with maple cabinetry, granite countertops, and stainless steel appliances, blending classic mountain character with modern convenience. The primary bathroom includes a soothing jetted tub, ideal after a full day on the slopes. A dedicated ski room offers exceptional functionality with a boot dryer, bench, cubbies, and ski rack, ensuring effortless gear organization. As a Solitude owner, you and your guests enjoy exclusive access to the Solitude Day Lodge amenities, including a heated indoor/outdoor pool, hot tub, sauna, and fitness room—the perfect complement to an active mountain lifestyle.
Bixby House 640/642 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks. Guest bedroom, with 2 queen beds, offers lock-out capability for separate rental opportunity. Enjoy convenient slopeside location at Bixby House, combined with the luxury amenities including an onsite owners' lounge, business center, private underground heated parking and access to the Spring House fitness center, heated indoor and outdoor pools, ice skating at the Ice House, slopeside hot tub and summer tennis. The only residences at Jackson Gore where homeowners can bring their furry four-legged friends along. Come see for yourself why slopeside living is so sweet at Okemo's Jackson Gore. This unit sleeps 8.
Welcome home to Trailside 15C on Okemo. Fully renovated and sold turn-key furnished, this 3-bedroom, 3-bath Trailside condominium is designed for effortless mountain living. The well-thought-out floor plan maximizes space and comfort, featuring a sun-filled main level with vaulted ceilings, exposed beams, and an open-concept kitchen, living, and dining area that captures a classic Vermont vibe. The spacious mudroom provides practical storage for all of your gear, while the deck extends your living space outdoors. Upstairs, retreat to a private primary en suite sanctuary. The lower level offers two additional bedrooms and a full bath, ideal for guests and family. A dedicated outdoor ski closet adds convenience after a day on the slopes. Enjoy Trailside’s amenities, including an in-ground pool and tennis courts, plus easy access to the Sachem Trail for winter skiing and summer hikes. This is four-season Okemo living at its best. Visit the Okemo real estate community today. Taxes are based on town assessment.
Welcome to F101, a perfectly located 2-bedroom, 2-bath condominium offering exclusive slopeside access and abundant sunlight from its Southern exposure. The unit boasts a desirable open floor plan and a private entrance for ultimate convenience. Sold fully furnished, this affordable gem provides an unparalleled mountain lifestyle. Residents enjoy the exclusive Day Lodge amenities, including the heated indoor/outdoor pool, hot tub, sauna, gym facilities, and a wonderful on-site dining option. Inquire now to schedule your private showing.
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!
Set on a peaceful country road, 535 Nelson Road offers classic Vermont charm with the convenience of being just a short drive to Okemo Mountain, Ludlow village, and the area’s lakes and recreation. This gambrel-style home sits on a beautiful 13.30 acres with a mix of wooded surroundings and open, usable field—ideal for enjoying privacy, gardening, and outdoor living. Inside, warm pine floors, exposed wood beams, and wood-plank ceilings create an inviting, timeless feel. The dining area is a standout, featuring a vaulted ceiling, skylights, and a wall of windows that allow natural light to pour in while overlooking the expansive yard. An open, eat-in country kitchen offers charming built-in cabinetry and excellent functionality for everyday living and entertaining. The living room centers around a wood stove—perfect for cozy Vermont evenings. The floor plan provides exceptional flexibility. One of the three bedrooms includes a wet bar and a private upper-level entrance, making it well-suited for guests. The finished basement offers an additional living area with a large den, a bonus room, and a full bathroom ready for renovation—an excellent opportunity to customize the space to your needs. Additional features include an attached, heated two-car garage, fenced garden area for summer vegetables, and an existing tennis court that could be revitalized or repurposed. A property that blends rural tranquility, character, and versatility—all within easy reach of the best of the Okemo Valley.
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!
Located in the heart of Jackson Gore at Okemo Mountain Resort, Adams House 717/719 Q1–4 presents a rare opportunity to own 100% interest in a traditionally quarter-share residence—all four quarters conveyed together, offering full ownership with excellent rental flexibility. This turn-key, ski-on/ski-off residence is being sold fully furnished, allowing a new owner to step right into the winter season with no setup required. The one-bedroom layout features two full bathrooms and lockout capability, allowing the home to function as one larger unit or two separate accommodations. The main living space includes a full kitchen with an open living/dining area, fireplace, sleeper sofa, and a murphy bed. The lockout bedroom offers two queen beds and a full bath, creating a flexible configuration that can sleep up to eight guests when used as a single unit. The lockout design also enhances rental versatility and income potential. Enjoy full access to Jackson Gore’s exceptional amenities, including 4 personal ski lockers, heated garage, heated indoor/outdoor pool and hot tubs, and The Spring House, which offers an indoor pool, hot tub, fitness center, and sauna. Jackson Gore is located near our lakes region as well as many award-winning golf courses, making this a true four-season destination. A unique opportunity to secure full ownership in one of Okemo’s most desirable slope-side locations, offered fully furnished and ready for immediate winter enjoyment. ROFR applies.
Motivated Seller! Rare opportunity to own this beautiful year-round Vermont Cape-style home! Only 5 minutes to Jackson Gore at Okemo. This updated and well-cared-for home has it all: hardwood floors, a cathedral ceiling, a finished basement with a kitchen, a covered rear porch, a mudroom, and a 2-car attached garage. Enjoy the backyard oasis, featuring an above-ground pool, a large CedarWorks playset for children, a fire pit, a Jamaica Cottage Shop shed, a poultry coop, and ample green space for your favorite activities. Just minutes to Okemo Mountain, Buttermilk Falls, VAST (snowmobiling trails), lakes, hiking trails, bike park, and numerous outdoor events: concerts, farmers' markets, and festivals. Living made easy with the rooftop solar array panels and the warmth of the pellet stove will help reduce your energy footprint while keeping utility costs low. This home checks all the boxes: space, sustainability, peace & quiet, and it's close to everything the area offers! The sellers had a new septic wastewater leach-field installed in October 2025. Don’t miss your chance to own a slice of Vermont tranquility at 491 Alpine Drive. 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.
Motivated Seller. Come see this Fully Furnished Move in Ready Retreat! Current owners are ready to pass along their special piece of Vermont. Enjoy the charms and privacy of a dead end road while being only five minutes from Jackson Gore at Okemo. Location is ideal for rental property or personal residence. This four bedroom home with two car garage and large basement has it all. Master suite above the garage gives privacy yet easy access to the rest of the home. Large slate entry has room for all your outdoor gear. Basement currently houses a pool table with room for even more toys or games. Step outside to a wonderful backyard with fire pit. Unwind in your 4/5-person hot tub, new in 2025. Quick access to both the VAST snowmobile and Catamount nordic trail systems. At the top of the Healdville trail you will find the fire tower with expansive views of the Okemo Valley. A fairly level yard and driveway allow for easy maintenance while a wooded area gives privacy and space for nature. The Generac generator will even kick on if you ever lose power. Furnished, cared for and ready for the next owner. Come see all this location has to offer!

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