Ludlow, VT | 45 Trailside Road

Set on a scenic knoll in a picturesque farm setting, just 10 minutes from Okemo’s Jackson Gore base and Ludlow village, this remarkable 6-bedroom, 4-bathroom property offers a rare combination of privacy, convenience and truly majestic Vermont views. Encompassing 9.7 acres, the setting is nothing short of magical, with sweeping vistas toward the backside of Okemo, Mount Ascutney, Killington, expansive valleys and spectacular sunrises!! From numerous windows throughout the home and outdoor spaces, the ever-changing mountain landscape becomes part of the experience in every season. Sit Back, Relax & Enjoy! Created for both grand entertaining and relaxed Vermont living, the property features an in-ground pool with pavilion, in-ground hot tub, beautiful summer gardens, stone patios, covered porch and deck. Inside there are spacious living areas, a finished basement, wood-burning fireplace and propane fireplace provide inviting spaces for gatherings or quiet evenings after a day on the mountain. Two separate garage structures add exceptional versatility. The detached garage offers additional space above, while the three-bay outbuilding includes heated space and rooms ready to be transformed into a studio, gym, workshop, recreation space or whatever your Vermont lifestyle demands. Whether envisioned as an extraordinary primary residence or a private four-season retreat, this enchanting property offers the space, setting and unforgettable views that make Vermont living truly special. Don’t miss this opportunity for this enchanting property. Schedule your showing today!!

An irreplaceable 27-acre land holding on Okemo Mountain, offering one of the most unique ownership opportunities in southern Vermont. With direct access to the Mountain Road Trail, acreage bordering the Sidewinder Trail, and Coleman Brook defining the northern boundary, this extraordinary property occupies a setting that is virtually impossible to replicate. Selective clearing could reveal sweeping easterly mountain views. Whether your vision is a legacy family compound, an exceptional private mountain retreat, or a long-term investment, opportunities of this scale and location rarely become available. Think beyond the existing improvements and imagine what 27 trailside acres on Okemo Mountain could become. The residence offers three levels of living space plus a basement and includes five marble bathrooms. The home has been vacant, vandalized, and is in significant disrepair, requiring extensive restoration. The condition of all utilities and mechanical systems is unknown, and the property is being sold strictly "as is." Winter access is currently by ski lift, with off-season access via Mountain Road. For buyers who recognize that truly exceptional locations cannot be recreated, this is an opportunity to secure one of Okemo Mountain's most remarkable land holdings.

45 Trailside Road offers the ideal combination of mountain living, generous indoor space, and exceptional outdoor living on Okemo Mountain. This distinctive mountain home welcomes you through a spacious mudroom with barnboard details and ample space for four-season gear. Beyond, natural light fills the open kitchen, dining, and living areas, creating an inviting space for gathering. The well-appointed, custom kitchen features cherry cabinetry, stainless steel appliances, an oversized island, a cozy breakfast nook, and easy access to the expansive deck. Outdoor spaces are a highlight, including a large curved deck overlooking the private, wooded backyard, a covered porch perfect for grilling, an extensive wraparound deck, and a hot tub for relaxing after a day on the mountain. The primary suite features vaulted ceilings, generous closets, and a beautifully remodeled bath with a soaking tub and heated floor. Three additional bedrooms, a family room, and a dedicated office provide plenty of flexibility for guests, recreation, and working remotely. A three-car garage offers abundant space for vehicles and recreational equipment. Enjoy proximity to Okemo’s slopes for winter skiing and summer mountain biking, while the nearby VAST trail network adds even more four-season recreation. With its warm Craftsman-inspired details, spacious layout, and peaceful mountain setting, 45 Trailside Road is designed to be enjoyed in every Vermont season. Visit the Okemo real estate community today. Taxes are based on town assessment.

Welcome to South Face Village!  True slopeside living at its best.  This front-row, ski-in/ski-out 3-bedroom, 3-bath condo is literally on the slope.  Walk out your front door, plop your skis or board down and head to the Sunshine lift.  This gives you direct access to the South Face Express Quad. Inside this immaculate, turnkey unit is everything you'll want in your mountain château.  Step in take off your boots hang up your coat and relax in the cozy living area in front of the gas fireplace while you take in the game or your favorite show.  The kitchen is state-of-the-art, which any chef will appreciate. Stainless steel appliances, ample counter space, a working breakfast bar and beautiful cabinetry.  You'll love the slopeside dining with two big windows to take in the outdoor action.  The convenience of a first-floor bedroom and full bath will be great for guests or grandparents.  Upstairs you'll find a second living space/family room.  This is where the kids will take over.  The bunkroom, washer/dryer, and 3/4 bath are right next to this fun space.  The primary en-suite is just that—sweet!  Overlooking the slopes you'll have a bird's-eye view of the day's conditions. The beautiful bathroom has a large walk-in shower with a seat, a double-sink vanity and more than ample closet space.  This wonderful condominium shows quality through and through.  The amenities are the crème de la crème, an outdoor heated pool and hot tub, an up-to-date workout facility and an incredible owners' lounge. This is the best and newest in slopeside communities, come take advantage of all South Face has to offer! You won't be disappointed.

Experience the essence of Vermont mountain living in this exceptional five-bedroom, four-and-a-half-bath retreat, ideally located just minutes from Okemo Mountain Resort and offering partial winter views of the mountain. Nestled on approximately one acre and boasting over 3,300 square feet of beautifully finished living space, this inviting home combines timeless mountain character with the comfort and amenities today’s buyers seek. From the moment you enter you will notice a soaring cathedral ceiling, natural woodwork, abundant natural light, and stunning wide-plank wood floors that create a warm and welcoming atmosphere. The spacious living room serves as the heart of the home, where a beautiful fireplace invites family and friends to gather after a day of skiing, hiking, golfing, or exploring Vermont’s four-season recreation. Designed for both everyday living and entertaining, the well-appointed kitchen features stainless steel appliances, beautiful cabinetry, and generous workspace for preparing everything from casual breakfasts to holiday meals. The private primary suite offers a relaxing sanctuary, while four additional bedrooms and multiple baths provide ample space for family and guests. The lower-level family room is the perfect destination for game nights and après-ski gatherings, complete with a billiard table and room to unwind. Step outside onto the expansive deck to enjoy fresh mountain air, seasonal views toward Okemo, morning coffee, summer barbecues, and evenings under the stars. A two-car garage offers convenient storage for vehicles and outdoor gear, while the home’s spacious layout comfortably accommodates large gatherings and memorable weekends. Whether you’re searching for a luxury vacation home, an investment opportunity, or a year-round residence, this remarkable property delivers the ideal blend of location, comfort, and mountain lifestyle in one of Vermont’s most sought-after destinations.