Ludlow, VT | 18 Pleasant Street 3

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.

If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and handsome antique details. The main and second floor each offer three bedrooms, two baths, kitchen, and, if needed, separate entrances. Recent improvements include a large enclosed hot tub room and a new heating system. The third floor features a play room, another bath and tons of bonus space. Lots of flexibility for buyers who seek generous space for extended family, guests or rental income. A great locale for your next mountain get-away!

Welcome to The Castle Hill Resort and Spa where you'll find this beautiful three bedroom, three and a half bath, condominium with loft and bonus room. The kitchen with custom cherry cabinetry, granite counters and stainless steel appliances that will satisfy any chef's needs is open to the living, dining area. Which have soaring cathedral ceilings and a wall of windows flooding in the natural light. A french door leading to the spacious deck so you can take in the Vermont fresh air is private with wooded views. Enjoy the flames of the gas fireplace in the living room after a long day on the slopes. The condo has been tastefully decorated and the furnishings are included. The spacious primary suite is fit for any king or queen, with a two person jetted tub, custom tiled separate shower with seat the complete the primary bath. The second bedroom en-suite, has it's own sitting room that can be locked out and rented separately. Upstairs to the bunk room, 3/4 bath, loft area and bonus room are a great space for guests or the kids. The amenities at the Castle include the Aveda Spa, workout facility with Life Fitness machines, free weights and a cardio room, inground heated year round salt pool, hot tub, tennis and pickle ball courts. Massage, manicures and pedicures are offered for a fee. Enjoy the culinary delight of Chef Fonz who is on premise at the Castle Restaurant and Inn, providing meals fit for any King and Queen! Choose this condo as your Vermont retreat and be treated like royalty at the Castle Hill Resort and Spa!

Unique opportunity to own a spacious three-bedroom townhouse at The Castle, one of the area's most sought-after luxury resort communities. Offering exceptional quality and amenities unlike any other in the region, residents enjoy year-round access to an Aveda spa, heated outdoor saltwater pool, tennis courts, a fully equipped fitness center with sauna and locker rooms, and an outdoor hot tub. Designed with timeless architecture and thoughtfully planned floor plans, this beautifully maintained townhouse offers both comfort and privacy. The residence features three bedrooms, including an oversized primary suite, a generous loft, a versatile den, and 3½ bathrooms, providing ample space for family and guests. This desirable ground-level end residence offers two levels of living with no neighbors above or below, ensuring exceptional privacy and quiet enjoyment. The easy, step-free entry provides convenient access for owners and visitors alike. Ideally located just four miles from Okemo Mountain Resort and the charming village of Ludlow, you'll also be minutes from the area's lakes, hiking trails, golf courses, and countless summer recreational activities. Whether you're looking for a year-round home, vacation retreat, or investment property, this exceptional townhouse offers the perfect blend of luxury, convenience, and four-season Vermont living.

Location, Location, Ski Access! Experience the best of mountain living in this spacious three-level end-unit townhome offering exceptional ski access and room for family and friends. Beautifully updated and move-in ready, this home features a newly remodeled kitchen with stainless steel appliances, granite countertops, updated bathrooms, and fresh paint throughout. With three bedrooms, a sleeping loft, and two-and-a-half baths, there's plenty of space to accommodate everyone. Wake up to breathtaking sunrises and long-range mountain views before heading out for a day on the slopes. Located just approximately 75 yards from the Sachem Ski Trail, you'll enjoy convenient ski access directly to the Sunburst Six chairlift, allowing you to start your ski day from the summit. Families will appreciate that beginner skiers and children can easily follow Sachem Trail to the base area for ski lessons and all resort amenities. As an end unit, this home offers added privacy with only one shared wall and no neighbors above or below. Ample parking, along with an easy walk to the tennis courts and the new outdoor swimming pool, makes this an ideal four-season retreat. An exciting bonus for the new owners: brand-new decks are currently being installed, providing a beautiful outdoor living space to enjoy for years to come. Whether you're looking for a ski getaway, a year-round mountain home, or an investment property, this is an exceptional opportunity and an outstanding value that shouldn't be missed.

Opportunity on Okemo! Walk to the Sachem Trail from this ideally located mountain home offering four bedrooms, two-and-a-half baths, and three levels of living space. Enjoy eastern views and bright morning sunrises. With no association fees and access from a publicly maintained road, this property offers the benefit of low overhead compared to other mountain residences.The price reflects the home’s current exterior condition, offering buyers the opportunity to make improvements as desired. Bring your vision and create your own Okemo retreat in a location that is hard to beat. Subject to Right of First Refusal by Vail Resorts.

Welcome to this charming, easy-care country home nestled on a private road in the heart of Cavendish, Vermont. Offering 4 bedrooms and two bathrooms, this inviting property combines comfortable living with the peaceful beauty of its natural surroundings. A covered front porch welcomes you into the foyer, where you'll immediately appreciate the open-concept floor plan designed for everyday living and effortless entertaining. The spacious living room features a cozy gas fireplace and flows seamlessly into the dining area, where a sliding glass door opens to the side deck, creating the perfect indoor-outdoor gathering space. The well-appointed updated kitchen overlooks the living and dining areas and features a center island, making meal preparation and conversation easy. The main level also includes a primary bedroom and a three-quarter bathroom, offering flexibility for office space or one-level living. Upstairs, you'll find three bedrooms and a full bathroom complete with a relaxing soaking tub. Outside, enjoy the tranquility of Vermont living with a level front yard, beautifully maintained gardens, and a spacious deck surrounded by nature. A covered front porch provides the perfect place to unwind on warm summer evenings, while the 3-sided carport offers added convenience year-round. The basement is ready to finish with egress-rated windows and bathroom drains plumbed, creating a great upside to increasing value! This home has a five-star energy rating. Located near Okemo Mountain and minutes from local schools, Singleton's General Store, the Cavendish Town Green, and several local restaurants, this home offers the perfect balance of country privacy and small-town convenience. Whether you're searching for a full-time residence or a Vermont retreat, this property is ready to welcome you home. (This house has a septic rated for 12 people!) Visit the Okemo real estate community today. Taxes are based on town assessment.

Welcome to The Castle Hill Resort and Spa where you'll find this beautiful turnkey four-bedroom, three-and-a-half-bath condominium with a loft. This unit is the best value in the complex. The renovated kitchen with granite counters and stainless steel appliances is open to the living and dining area. This area has soaring cathedral ceilings and a wall of windows flooding in natural light. A French door leads to the spacious deck, which offers privacy and wooded views, perfect for taking in the Vermont fresh air. Enjoy the flames of the living room gas fireplace while relaxing on the plush sofa after a long day on the slopes. The entire condo has been tastefully decorated by a professional and the included furnishings are in great condition. The spacious primary suite is fit for any king or queen. The primary bath is complete with a two-person jetted tub and a custom-tiled separate shower with a seat. The second bedroom is an en-suite with its own sitting room that can be locked out and rented separately. Upstairs, the bunk room, 3/4 bath, loft area and bonus room provide a great space for guests. The amenities at the Castle include the Aveda Spa, a workout facility with Life Fitness machines, free weights and a cardio room, an in-ground heated year-round salt pool, a hot tub, and tennis and pickleball courts. Enjoy the culinary delight of Chef Fonz who is on premise at the Castle Restaurant and Inn, providing meals fit for a King! Choose this condo as your Vermont retreat and be treated like royalty at the Castle Hill Resort and Spa.

Trailside Village on Okemo, Unit 9C, is a meticulously maintained three-bedroom plus loft, two-bath condominium with direct ski access to the Sachem Trail. Beautifully updated throughout, the home features a renovated kitchen and bathrooms, custom wood trim, solid wood interior doors, and a warm blend of hickory hardwood flooring, tile, and plush carpeting. Thoughtful upgrades include enhanced lighting, newer appliances, and a recently installed washer and dryer. The spacious lower-level family room provides the perfect gathering space after a day on the slopes. Step outside through the sliding doors to a future outdoor retreat, where association-approved plans for a 9' x 9' deck or patio are already in place. With exterior wiring and a water spigot already installed, the space is ready for your dream hot tub. Designed for year-round comfort, the home features a Mitsubishi three-zone heat pump with WiFi controls, providing efficient heating and cooling for every season. Offered fully furnished, this turnkey property is ready for immediate enjoyment, whether you're looking for a personal mountain getaway, a full-time residence, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on the current Town of Ludlow assessment.

Set back in the woods on a quiet road, this property is within 5 minutes of Okemo Mountain Resort, golfing, shopping and dining. The open concept floor plan on the main level is inviting and warm, offering enough space for friends and family to gather. A wall of windows allows you to watch the winter snowfall, admire the summer greenery and the fall foliage, while also overlooking the back deck. The main floor also has an airlock mudroom along with two bedrooms, a full bath and a half bath. The upper floor has a nice loft, a bedroom, a bonus room/office and a 1/2 bath. There is also a 1 car garage with storage space!

Enjoy elevated, modern comfort completely off the grid. This cabin features a premium, self-sufficient utility system engineered specifically for remote living. Combining a powerful solar array with high-capacity battery storage, it delivers a quiet, reliable, and uninterrupted power supply. Smart home technology provides the convenience of monitoring and controlling the property’s essential systems, including power, battery storage, security, and climate, directly from your smartphone, giving you peace of mind from virtually anywhere in the world. This 9.45± acre property has gorgeous, expansive views of Killington and the Branch Brook Valley, is surrounded by State Forest and conserved lands, and sits adjacent to the Catamount and VAST Trails. Inside, this private sanctuary has been thoughtfully reimagined to balance modern luxury with the quiet soul of nature. The interior serves as a cozy retreat, featuring a minimalist aesthetic that prioritizes texture, light, and high-end craftsmanship. Large windows act as living art, framing the surrounding mountains and forest, and flooding the home with natural light. Located just 11 miles to Okemo Mountain and 25 miles to Stratton, with easy reach to Bromley, Magic, and Killington, and with many lakes nearby. Furnishings may be purchased separately. Now imagine yourself sitting on the deck with your favorite beverage, taking in the breathtaking Mountain Views.

Discover the quintessential Vermont mountain getaway at this inviting 3 bedroom, 2-bath South Hill home, offered fully furnished and turnkey with a proven short-term rental history. Whether you’re looking for a private retreat, an income-producing property, or the best of both, this home is ready to enjoy from day one. Set in the heart of the Okemo Valley, the location offers exceptional four-season appeal. Spend winter days skiing and snowboarding at Okemo, then return home to the warmth of a wood-burning fireplace and a relaxing soak in the 6-person hot tub. In summer and fall, enjoy hiking, biking, golf, lakes and the wonderful level and private back yard. Inside the wood two living areas, and a spacious lower-level recreation area provide plenty of room to gather and unwind. The eat-in kitchen features a massive granite-topped island with generous seating perfect for morning coffee or après-adventure meals with family and friends. Outside, the expansive two-tier deck creates an ideal setting for dining, entertaining, or simply enjoying the fresh mountain air. A detached shed provides convenient storage for skis, bikes, and other outdoor gear. With its desirable South Hill location, strong rental history, comfortable furnishings, and immediate access to the Okemo Valley lifestyle, this is a truly turnkey Vermont property with the flexibility to enjoy now and rent when you’re away.

The historic Masonic Temple building is located in the heart of Ludlow Village at the corner of Depot Street and Pleasant Street. This top-floor condo with vaulted ceilings offers the perfect blend of in-town convenience and year-round Vermont adventure. Just steps from local shops, restaurants, and everyday amenities, you’ll love the ease of village living while being only minutes from Okemo Mountain Resort. Unit #3 is a spacious four-bedroom, three-bathroom residence situated on the top floor, offering ample room for gathering with family and friends. The thoughtful layout and renovated kitchen provide both comfort and privacy, making it ideal as a primary residence, vacation getaway, or investment opportunity. This four-unit building also features a shared basement common area, perfect for relaxing or socializing after a day of outdoor activities. Whether you're hitting the slopes, exploring nearby golf courses, enjoying the lakes region, or taking advantage of hiking and biking trails, this location puts you at the center of it all. Experience the charm of village living with unbeatable access to everything Ludlow has to offer, including ski shuttle access across the street! This is your opportunity to own a piece of Vermont in one of its most desirable four-season destinations. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Welcome to your private country oasis. Nestled in a serene and peaceful setting, this pretty, two-level country home perfectly blends rustic charm with modern convenience. As you step inside, you are immediately greeted by an inviting open-concept living, dining, and kitchen area designed for seamless everyday living and effortless entertaining. This home features a magnificent stone wood-burning fireplace, ideal for warming up on crisp Vermont evenings. On warmer days, you will enjoy air conditioning. Vaulted ceilings with exposed wood beams enhance the spacious, airy feel while preserving that quintessential country warmth. The thoughtful architectural layout offers maximum flexibility, with bedrooms and bathrooms conveniently located on both levels. The lower level is dedicated to a spacious and private primary bedroom suite, serving as a peaceful retreat complete with direct, walk-out access to the yard. Upstairs and downstairs, the home delivers a true country feeling, making it easy to relax and unwind. Step outside to enjoy the beautiful covered back deck, the perfect spot for morning coffee, evening dining, or simply listening to the sounds of nature. The home sits on a nice open yard that offers abundant space for outdoor recreation, gardening, or lawn games. Adding to the utility of the property is a detached two-car garage, providing excellent storage for vehicles, ski gear, and outdoor equipment. Location is everything, and this property puts the best of the region right at your fingertips. You are just minutes away from world-class skiing and riding at Okemo Mountain Resort, championship golfing, local boutique shopping, and diverse dining options. Plus, the nearby lakes region offers endless summer boating, swimming, and fishing. Whether you are looking for a year-round residence or a premier four-season vacation getaway, this country home offers the privacy you crave with the convenience you need.

Experience true slopeside living at SouthFace Village on Okemo Mountain in this beautifully furnished one-bedroom, two-bathroom condominium with direct ski trail access. Designed for both comfort and ultimate convenience. This mountain retreat features a spacious exterior and a mudroom closet, perfect for storing all your ski gear after a day on the slopes. The main level offers an open-concept floor plan where the living room, centered around a cozy gas fireplace. This then flows seamlessly into the dining area and a well-appointed kitchen with a large island, creating the perfect space for entertaining family and friends. A convenient half bath completes the main level. Upstairs, you'll find a spacious bedroom, a full bathroom, and a versatile family room or den, offering additional living space for guests, a home office, or a relaxing lounge area. SouthFace Village offers exceptional resort-style amenities, including an outdoor heated pool, hot tub, fitness center, covered parking garage, and a private chairlift providing effortless access to the entire Okemo Mountain trail network. Whether you're seeking a weekend getaway, a year-round retreat, or an investment opportunity, this turnkey condominium delivers the ultimate Vermont mountain lifestyle in one of Okemo's premier slopeside communities. Visit the Okemo real estate community today. Taxes are based on town assessment.

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.

If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large breakfast bar. Oak cabinetry, mostly stainless steel appliances, tile backsplash and under counter lighting. You'll love the open concept of the kitchen and dining room, with a granite two sided fireplace. Mozie on into the large living room with space for the whole crew and cozy up to the other side of the fireplace. The first floor is completed with an en-suite bedroom with a beautiful view of Hawks Mountain, the bathroom is finished with a tiled shower and a natural wood vanity. Rounding off the main floor with a half bath laundry room combo and a convenient corner nook for gear storage. Upstairs you find another en-suite bedroom with double sink, natural wood vanity and tiled shower. The two other large bedrooms share a full bath. One bedroom with a balcony overlooking Hawks Mountain State Forest which is a healthy walk away for recreating. Now down the the lower level where the fun begins. Pool table, foosball or a game of cards, pick your favorite. This Ultimate Village Ski House is priced to sell! Come take a look today!

This Lake Pauline residence offers an inviting, easygoing retreat in a convenient yet quiet location close to Okemo Mountain Resort. The cottage-style home features an open living and dining area with a cozy gas stove and access to a deck overlooking the water. The lakeside yard provides plenty of room for relaxing, lawn games, swimming, kayaking, and gathering around the firepit. Improvements completed within the past two years include Andersen windows, an updated kitchen and bath, and a new furnace. A delightful four-season getaway where lake and mountain living come together.

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.

Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood stove creates the perfect setting for relaxing with family and friends. French doors lead to a spacious deck overlooking the beautiful backyard, an ideal spot for morning coffee, summer entertaining, or simply enjoying the peaceful surroundings. The home features five bedrooms, beautiful wood floors rich with history and character, and recent improvements including a newly replaced septic tank by the current owner. With its timeless appeal, spacious layout, and wonderful setting, this property presents an exceptional opportunity to restore and elevate a classic Vermont home to its next chapter.

Private, yet accessible location on South Hill. These are hard to come by! Nicely set back from the road is this two-story contemporary with room for family and guests. Nice lawn area as well as wooded acreage. You will enjoy your peace and quiet as you sit out on your covered porch with a cup of coffee or a cocktail! Enter into a small mudroom and you have a half flight of stairs going either up or down. On the upper level, you have three accessory rooms...den, office, and bonus room that would be a great laundry room. Nice kitchen space with light and it's open to the dining room and living room. Slider out to the huge, covered porch and large open deck. There's a woodstove hookup in the living room. On the lower level, there are three good sized bedrooms and a large family room with a walk out entrance and windows on three walls. This will be a wonderful home for the next owner. The current owner has enjoyed 25 years here. You can be next!

Tucked into a wooded setting just minutes from Okemo Mountain and Ludlow Village, this easy-keeping Saltbox makes a comfortable and uncomplicated Vermont home base. The main level features an open kitchen, dining and living area with vaulted ceilings, hardwood floors and a centrally located wood stove, plus a bedroom and full bath. Upstairs, an open balcony overlooks the living area and leads to two additional bedrooms and a second bath. The walkout lower level offers a den, laundry and generous storage space. A detached two-car garage and woodshed provide plenty of room for vehicles, snowmobiles and outdoor gear. Recent improvements include a new boiler and hot water heater (2025), hardwood flooring (2020) and a standing seam roof (2019). Convenient, comfortable and easy to maintain; just the kind of Vermont getaway that is close to everything be it hiking, biking, snowmobiling, skiing and golf!

Tucked along a quiet side street in Ludlow Village, 16 Smith Street is filled with warmth, character, and timeless New England charm. Beautiful wood floors, rich natural woodwork, and classic pocket doors highlight the home’s craftsmanship, while a spacious wraparound porch invites you to slow down and enjoy village life. Inside, the large country kitchen features an eat-in island and opens to an additional flexible space ideal for a breakfast nook or cozy sitting area. The inviting living room is warmed by a pellet stove, perfect for taking away the chill after a day on the slopes. With three bedrooms and three bathrooms, the home offers comfortable space for owners and guests. The primary bedroom includes a recently remodeled en-suite bath, while the two additional bedrooms share another beautifully updated bathroom. Outside, a large deck provides plenty of room for dining and entertaining, and the backyard offers space to relax and play without demanding overwhelming maintenance. A detached garage/barn adds valuable storage and versatility. All of this is within walking distance of Ludlow’s shops and dining, with Okemo Mountain Resort just minutes away. A charming village home offering comfort, convenience, and an authentic sense of place. Visit the Okemo real estate community today. Taxes are based on town assessment.

This classic old farmhouse radiates charm and captures the timeless spirit of Vermont living. Lovingly held by one family for over a century, this historic property perfectly balances privacy with exceptional convenience, sitting just over a mile from Main Street in Ludlow. The original home dates back to the pre-1900s, while a thoughtfully integrated 1970s addition introduces rich, Vermont-sourced barn beams into its architecture. Outdoor lovers will appreciate the perennial gardens, patio at the rear of home, two handy garden storage sheds, and direct frontage on Jewell Brook, the perfect spot to dip your toes in and unwind on warm afternoons. A sun-filled, three-season front porch with large windows leads to the kitchen, which has brand new appliances, and an adjacent full bathroom. This home offers three distinct and versatile common areas designed for relaxation and entertaining. The oversized living room serves as the heart of the home, anchoring the space with a wood-burning fireplace, real barn beam ceilings, and expansive windows that flood the room with natural light. Adjacent to the living room, an additional family room features exposed beams and skylights, opening directly onto a peaceful backyard patio. A separate dining room is situated just off the kitchen's other side. A spacious mudroom connects the garage with the living room and serves as the typical Vermont winter season entry, keeping outdoor gear neatly organized. The flexible floor plan accommodates main-level living with an ensuite bedroom on the ground floor. Upstairs, the home expands into two additional spacious guest bedrooms, one of which includes a convenient half bath. Adding to the property's immense potential is a two-car attached garage featuring an unfinished second floor, offering an ideal canvas for a future studio, home office, or guest suite.