Properties Near 44 Freeman Road Cavendish, VT

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.

Welcome to the House of Fives—ideally located five miles from Okemo, five minutes to Ludlow, and offering five bedrooms for comfortable mountain living. This spacious log home features two great rooms plus a third living area, providing ample space to spread out for one or even two families. The open-concept main level seamlessly connects the kitchen, living, and dining areas, centered around a pellet-burning fireplace insert. With two sets of sliders and overhead windows, natural light pours into the space, creating a bright and inviting atmosphere. Step outside onto the large deck to further enhance your outdoor living experience. The expansive unfinished area of the lower level offers a blank canvas for a game room, workshop, or additional storage. A fun loft overlooks the main living area, while knotty pine paneling throughout delivers a warm, classic cabin feel. Outdoor enthusiasts will love the direct access to the VAST snowmobile trail—ride right from your home, with plenty of room for friends to park their sleds too. Set on 23 acres, the property even offers the opportunity to create your own private trails through the woods. Visit the Okemo real estate community today. Taxes are based on the town assessment.

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.

Discover your private Vermont sanctuary on 36 acres of forest and pond. This contemporary 4-bedroom, 3-bath home blends comfort and style with an open floor plan, spacious kitchen, and living area anchored by a wood-burning fireplace. Slider doors open to a wraparound deck with a hot tub, perfect for enjoying the tranquility of nature. Two primary suites, including a first-floor option, plus two additional large bedrooms, offer flexible living for family and guests. Additional features include a mudroom and attached 2-car garage. Lovingly cared for by the same family for over 25 years, this retreat embodies the quintessential Vermont lifestyle—peaceful, private, and close to the outdoors. Just minutes from Okemo Mountain, Ludlow, and Chester, enjoy skiing, hiking, local shops, and dining. A true year-round escape where nature, recreation, and small-town charm come together.

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.

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has wooded private views. These sought after ground floor units give flexibility to owners as you can stay on one side while renting out the other with the lockout capabilities. The furnance and hot water tank have recently been updated. The Castle Resort & Spa is beautiful and enjoyed year-round. From skiing in the winter, to the lakes in the summer, golf in the spring, or hiking in the fall, this area has so much to enjoy. You can explore the area with endless adventures or stay at the resort enjoying all the amenities on site. Conveniently located inside The Castle Resort is a fine dining, French influenced American cuisine restaurant. Relax at the Aveda spa with a massage, use the fitness center, or take a Pilates class all on site at the resort. A year-round heated, salt water pool and tennis courts are more amenities you'll enjoy! After a day on the slopes at Okemo Mountain, relaxing by the fireplace or indulging in all the Castle Resort has to offer, truly make it a perfect getaway! Visit the Okemo real estate community today. Taxes are based on current town assessment.

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 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!

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.

Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the stairway, this home could be opened back up into a large single-family home. The attached barn adds some great space for fun and potential or just storage. It makes this home a true Vermont property. Both units are currently rented bringing in good income from great tenants who would like to stay. Be part of the Cavendish community just minutes from Okemo, the lakes, and an easy drive to I-91.