Properties Near 130 Pleasant Street Cavendish, VT

Looking for your dream Vermont escape? Look no further than this unique and spacious home conveniently located between the towns of Chester and Ludlow. The main floor has a master bedroom, bathroom, dining room, kitchen, and two large living rooms complete with wood burning fireplace. Upstairs are 3 more bedrooms, a bathroom, 2 large bonus rooms, 2 lofts for office, storage, or playroom space, and a book nook with a couch overlooking the main floor living room. Outside you will find a recently added stone patio with wood and propane fireplace, deck, hot tub under cover, a 20kw standby propane generator. Other great updates include a brand new roof, egress windows, newer mini splits for a/c and heat in each bedroom, paved driveway. Lots of furnishings will stay with the house, so just bring your suitcase and skis/snowboards and you are ready for the season! Magic, Okemo, Bromley, and Stratton are not far away! Don't wait, schedule your appointment today to see this beauty!

Welcome to Castle Hill E-3, a charming and meticulously maintained two-bedroom plus den condo that perfectly balances comfort and style. This inviting end unit features a cozy den complete with a wet bar, ideal for relaxation and entertaining. Step inside to discover stunning wood flooring that enhances the warm atmosphere, complemented by elegant granite countertops, modern appliances, and a breakfast counter in the kitchen. Enjoy the convenience of ample outdoor space right at your doorstep, along with hassle-free parking. Nestled in a picturesque condominium community surrounded by the majestic mountains near the historic Castle Inn, listed on the National Register of Historic Places, Castle Hill offers an exceptional living experience. Take advantage of luxury resort amenities including two tennis courts, a year-round heated outdoor saltwater swimming pool and hot tub, and a full-service Aveda Health Spa and Fitness Center. Plus, indulge your taste buds at the award-winning Castle Inn Restaurant, located within the resort complex. Experience the perfect blend of luxury and tranquility at Castle Hill E-3, your ideal mountain getaway awaits!

If royalty is how you'd like to be treated then you've found your Castle. This two bedroom condominium is located at the Castle Hill Resort and Spa with unsurpassed amenities that any king and queen would appreciate. Just 3 miles to Okemo and all Ludlow has to offer and around the corner from charming, vibrant Proctorsville Green. This impeccable condo has been updated, well cared for and loved by the current owners. Finely appointed with tasteful furnishings through out the unit. With two bedrooms, a den, and lock out capabilities, you have plenty of space and rent flexibility. In the kitchen you'll appreciate cherry cabinetry, granite counters and stainless steel appliances. Enjoy hardwood floors through out the open kitchen, dining and living areas. The gas fireplace will keep everyone cozy after a long day on the slopes. The master suite has a walk-in closet, custom tiled bath with jetted tub and cherry vanities with granite tops. The second bedroom is ensuite and has a den which can be locked out and rented on it's own. The unit has central air-conditioning for year-round comfort. Relax by the pool, soak in the outdoor hot tub, play tennis or work out in the gym at the Aveda Health Spa. Just around the corner is the quaint village of Proctorsville, the quintessential Vermont town! Home to Singleton's Store, Outer Limits Brewery and Murdock's Restaurant on the Village Green which hosts concerts Wednesday evenings in the Summer. A perfect setting for your Vermont getaway!

If royalty is how you'd like to be treated then you've found your Castle. This two bedroom condominium is located at the Castle Hill Resort and Spa with amenities that any king and queen would appreciate. Just 3 miles to Okemo and all Ludlow has to offer. And around the corner from charming, vibrant Proctorsville Green. With two bedrooms, a den, and lock out capabilities, you'll have plenty of space and rent flexibility. In the kitchen you'll appreciate granite counters and newer appliances. Enjoy hardwood floors in the open kitchen and dining areas. The gas fireplace will keep everyone cozy after a long day on the slopes. The primary en-suite has a walk-in closet, custom tiled shower, jetted tub and dual vanities with granite tops. The second bedroom is en-suite and has a den which can be locked out and rented on it's own. The unit has central air-conditioning for year-round comfort. Relax by the pool, soak in the outdoor hot tub, play tennis or work out in the gym at the Aveda Health Spa. Just around the corner is the quaint village of Proctorsville, the quintessential Vermont town! Home to Singleton's Store, Outer Limits Brewery and Murdock's Restaurant on the Village Green which hosts concerts Wednesday evenings in the Summer. A perfect setting for your Vermont getaway!

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.

This home has served as a primary residence and also as an income-producing rental. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well. It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for friends and family. Perhaps this is the reasonably-priced property not needing a lot of work that you have been waiting for? Become part of the Cavendish Community and have access to many ski mountains including Okemo. (This property has tenants with an annual lease from 9/1/2025 to 8/31/2026. Lease must be honored. Details available for interested buyers. There will be an easement from High Street to the back of the property to access the garage and back of the house, but the parking for this property is the driveway above the house on Pleasant Street.)

5 Minutes from North Springfield and 22 minutes to Ludlow sits the peaceful hamlet of Baltimore, VT. Within the town is a 6 acre lot complimented with fruit trees, a stream, and an ample barn/garage with some roughly finished area above perfect for overflow guests, a home based business or perhaps even additional living space as your needs grow. There's also a storage shed! The house is sizable with about 1,546 square feet of finished living space and a full basement under a 3rd of it. The property has about 2+ acres of open land which has been recently seeded. Enjoy one of two decks and take in nature, peace and tranquility. Or putter in your ample garage/barn. Private yet convenient to some of the best snowmobiling and skiing Vermont has to offer, this property is suitable for fulltime or vacation home use. (Listing Agent is related to Seller)

3-bedroom, 3-bath Ranch-style home in a quiet North Springfield neighborhood with garage. This single-level rambler offers ease of living with a functional floor plan. Includes a partially finished basement with 3/4 bathroom. Set on a beautiful lot complete with sugar maples, pear, plum, and peach trees, a 21' round above ground pool with decking, and patio area with firepit to enjoy the open air on these Fall evenings. With its desirable location close to town amenities, schools, and outdoor recreation, this home is a great opportunity for first-time buyers, downsizers, or anyone looking for comfortable single-level living in Springfield, Vermont. Delayed showings until open house on Sunday 9/21/25 10-12n

Bring your vision to this charming 3-bedroom, 1-bath farmhouse in the heart of Cavendish, a true opportunity for those looking to restore or reimagine a home with character. Set on a generous 1.6-acre lot, the property offers endless potential with plenty of space to expand, garden, or create your dream outdoor retreat. Inside, you’ll find original hardwood floors throughout and good bones that provide a solid foundation for updates and customization. The oversized detached garage is a major bonus, ideal for workshop space, storage, or hobby use. If you’re searching for a project with classic New England charm and room to grow, this is the one. Unlock the potential and make it your own!

AFFORDABLE SKI HOME NEAR OKEMO MOUNTAIN RESORT Discover your perfect Vermont getaway with this charming 3-bedroom, 2-bath ski home just minutes from Okemo Mountain Resort in the heart of Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept 1977 home on .26± acres combines comfort, convenience, and exceptional value in one of the most desirable areas of the Okemo Valley. Step inside to a spacious, sun-filled living room, a bright eat-in kitchen with breakfast nook, and an enclosed breezeway—the perfect spot to relax or entertain after a day on the slopes. The primary bedroom and living room offer generous space, while the two-car garage and paved driveway provide everyday practicality. Outside, enjoy mountain views, mature landscaping, and a private yard with room to gather, garden, or play. From your doorstep, walk to Proctorsville Village for local dining, the iconic Singleton’s General Store, or the nearby elementary school. Whether you’re hitting the slopes at Okemo, golfing at Fox Run Golf Course, or simply soaking in Vermont’s four-season beauty, this property is a rare opportunity to own an affordable ski home in one of southern Vermont’s most loved destinations. Move-in ready and waiting for your next adventure.

Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on the third floor and above the garage. The 2 story bay windows make an architectural statement and the lower one has a wrap-around window seat. With a standing-seam metal roof and vinyl siding, this is an easy-to-maintain exterior. This home will need some updating and will be sold fully furnished. Located less than 5 miles from Okemo Resort and walking distance to the famous Singleton's General Store and the town green where the bus stop is located. The green also hosts a summer concert series, and Murdocks Restaurant.

Step back in time with this charming brick Colonial home, built in 1830 and beautifully situated in the heart of Proctorsville Village. Rich in history and character, this residence offers the perfect blend of classic New England architecture and convenient village living—just steps from shops, schools, restaurants, and the village green that adds to its timeless charm. The main level welcomes you with a traditional layout featuring a spacious country kitchen, a formal dining room, and a large living room ideal for gatherings. A full bathroom on this level adds modern comfort and convenience. Upstairs, you’ll find four inviting bedrooms and a three-quarter bathroom, providing ample space for family and guests alike. The third level offers attic space that has the potential to become additional living space. Enjoy the best of Vermont’s four seasons from this ideal location—just a short drive to Okemo Mountain Resort for skiing and snowboarding, nearby hiking and biking trails, scenic rivers and lakes for summer adventures, and local golf courses for leisurely afternoons. This is the perfect location just to catch a concert on the green or cross the street for a cup of coffee. Whether you’re seeking a primary residence, a vacation getaway, or a piece of Vermont history, this Cavendish Village gem offers warmth, character, and endless potential in a quintessential small-town setting.