Properties Near 33 Pleasant Street Extension Ludlow, VT

Okemo Trailside 22-CL is a spacious one-bedroom with a bunk room, ideally located just a minute's walk from the Upper Sachem Trail. This ski-in/ski-out condo, which has seen significant renovations, offers flat, easy access to the slopes and community amenities. Inside, you'll find an open 884-square-foot layout. The entry features a mudroom with rustic pine accents, perfect for storing gear. The renovated kitchen with new appliances includes a breakfast bar that flows into a separate dining area, while the sunken living room centers around a cozy soon-to-be-installed Regency electric fireplace. The unit includes a primary bedroom with an en-suite bathroom, a separate bunk room, and an in-unit laundry room with a side-by-side washer and dryer. Enjoy a short walk to the community pool ( currently being totally rebuilt) and 2 tennis courts, making this condo an ideal retreat for year-round recreation.

Outstanding views of Okemo Mountain from this well maintained, 3 bedroom, 2 full-bathroom condo with upgrades throughout. Living space is open and centered on a woodburning fireplace. Great mudroom with space to store all your gear. Located on the second level, this unit is bright with a private deck to enjoy sunsets and unobstructed views of ski trails, Black River, and pool. Primary bedroom has an updated ensuite bathroom and walk-in closet with built-in shelving. Updated kitchen and breakfast bar, all new lighting throughout, new hot water tank, and air-conditioning unit. Great access to skiing on the free mountain shuttle and an easy walk to village shops and restaurants. One of the best locations in Brookhaven!

Enjoy a fantastic four-season location featuring a beautiful new in-ground pool for summer enjoyment and convenient Okemo shuttle service to the slopes during ski season. Ideally situated close to Main Street in Ludlow and just five miles from the area’s lakes. This well-maintained three-bedroom condo offers a comfortable layout with a primary suite and an open, spacious living and kitchen area. A wood-burning fireplace creates a warm and inviting atmosphere—perfect for crisp foliage-season days and cozy Vermont winter evenings after a day on the slopes. The updated kitchen provides excellent storage, and the breakfast counter is ideal for additional seating or meal preparation. The condo is light and bright and includes a private deck for relaxing outdoors. An easy-to-maintain property with plenty to offer, this condo represents an excellent value in a highly desirable location.

Recently refreshed 3BR/2Bath Condo, 5 minutes to Okemo Mountain Resort, 30 minutes to Killington Skyeship. Seasonal swimming pool.

Okemo Mountain Lodge, come experience unbeatable convenience, ideally located at the base of Okemo Mountain Resort. This one-bedroom residence offers the ease of ownership with true ski-in/ski-out access. Easy access to the main base area, where ski services, lifts, dining, and après-ski options are all right outside your door. The unit comfortably sleeps four, making it perfect for personal getaways or hosting guests. With a proven rental history through Okemo Mountain Resort, this property presents an excellent opportunity for both enjoyment and investment. Own your mountain escape and start making memories slopeside. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Opportunity meets flexibility at this charming two-unit property in the heart of Proctorsville. Ideal for an owner who wants a vacation getaway with built-in income potential — or as an easy, turnkey investment — this well-kept duplex offers multiple paths to ownership. The downstairs unit features a three-season porch/mudroom entry, two bedrooms, an open-concept living, dining area, and kitchen, a full bath, and a dedicated laundry/storage room. It comes partially furnished and currently has a lease in place, providing immediate income. Upstairs, the second unit offers two bedrooms, a comfortable open living and dining room or home office, an eat-in kitchen, a full bath, a large three-seasons porch, and a private deck overlooking open meadow views. The upper unit is vacant and ready for personal use or rental. The location is unbeatable — walk to shops, dining, and village amenities in Proctorsville, and enjoy being less than 10 minutes to Okemo Mountain. A rare opportunity to combine lifestyle and investment in one property. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Terrific village home with bright, open living spaces! This property offers the perfect backdrop for sun-drenched days, featuring charming gingerbread trim and a unique, versatile room above the porch. As you enter through the welcoming sunroom, you’ll immediately enjoy the airy, open layout that connects the sunroom, dining room, and kitchen—perfect for breezy, seasonal gatherings. The first floor provides great flexibility with a comfortable living room, a family room with convenient laundry hookups, a workshop, a bedroom, and a three-quarter bathroom. Whether you’re looking for single-floor living or extra space for guests, this home adapts to your needs. The second floor features two guest bedrooms, a three-quarter bathroom, and a spacious primary bedroom with a walk-in closet. If you need even more room to grow, both walk-up attics are ready to be transformed into bright studio or hobby spaces. When you're ready to enjoy the beautiful Vermont weather, step outside to the expansive, partially fenced yard. It is the ideal setting for gardening, hosting lawn games, or relaxing on the patio for al fresco dining during long, warm summer evenings. The property also includes a two-story barn, providing plenty of storage for bikes, kayaks, and all your outdoor gear. Located in the heart of Cavendish, you’ll be just moments away from local favorites like Singleton’s Store and the Vermont Apple Pie Bakery. With summer recreation in mind, you are only 6–8 miles from world-class golf courses, pristine lakes for swimming and boating, and the scenic trails surrounding Okemo. Schedule a showing today to see how this charming village home can be your perfect summer retreat!

Fabulous ski-in/ski-out opportunity at the base of Okemo Mountain! This top-floor (3rd level) one-bedroom, one-bath condominium offers unbeatable convenience and beautiful views overlooking the Okemo Base Lodge and the A-B chair lifts. With a sleeper sofa for additional guests, it’s the perfect Vermont retreat for weekend getaways or extended stays. A new electric fireplace provides ambiance and warmth for cozy evenings. Step right outside to enjoy the base lodge restaurants, outdoor fire pit, and year-round amenities. Walk over to the Loft for a casual burger and beverage, or take a quick two-minute drive to all the shops, dining, and entertainment along Main Street in Ludlow. You’re also just five minutes from Fox Run Golf Course, scenic Route 100, and the Lakes Region. Comfortable, convenient, and ideally located, this condo is a wonderful choice for family ski vacations or an excellent rental investment in the heart of the Okemo Valley.

This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen with breakfast nook, and a wonderful enclosed breezeway—the perfect spot to relax or entertain in 3 seasons. The living room offers generous space with picture windows creating plenty of light. The second floor spacious, primary bedroom is equipped with many outlets for charging devices. Two additional bedrooms and a 3/4 bath complete the second floor. House re-built in 70's. The two-car attached garage provides workshop and storage space off the paved driveway. A very neat, clean and dry basement with up newer oil tank, Thermopride furnace and bulkhead doors that open to the breezeway. Enjoy mountain views and a deep yard with space for gardening and winter fun tubing or sledding. Walk to Proctorsville Village for local dining, Singleton’s General Store, or the elementary school. Whether you’re hitting the slopes at Okemo, golfing at Fox Run Golf Course, or simply enjoying Vermont’s four-season beauty, this is rare opportunity to own an affordable home in one of Southern Vermont’s most popular destinations. Motivated sellers encouraging offers.

Sun-drenched and thoughtfully designed, this one-bedroom condo is ideally located in the sought-after Trailside community, just moments from the Sachem Trail, the new in-ground swimming pool, tennis courts, and additional parking. Offering true four-season appeal, it provides effortless access to Okemo Mountain while also serving as a comfortable year-round retreat. The open-concept layout is enhanced by high ceilings, bleached wood finishes, and a striking new wood-burning fireplace, creating a bright and airy ambiance throughout. The well-appointed bedroom includes ample storage, and two built-in bunk beds add flexibility for guests, making this an inviting and highly functional mountain getaway with strong rental potential.

Located in the Village Of Ludlow this turn key ranch has been a great second home/investment for the current owner. Situated on the the outskirts of town with a classic neighborhood feel and the comfort of locals nearby. Take in the Okemo views as soon as you set foot on the property with ample parking for guests in the circular driveway. Step into the recently renovated house to include windows, metal roof and updated interior. This easy keeper is fully equipped and has hardwood floors and bunk beds for the kids that will bring years of memories for the family. The bonus space is ready to be finished to add real value to the home. The plan is drafted for a primary ensuite bedroom with sitting room and a spacious family room. Come check out this village home today! It won't last long...

This charming home, cherished by one family since the mid-1950s, presents a wonderful opportunity for renovation and personalization. This nine room home has 4 bedrooms, 1 bath, and an eat-in kitchen. The location is ideally situated within walking distance of Dorsey Park and Ludlow Village. Catch the shuttle bus to Okemo for a day of skiing or walk to the restaurants, grocery store and all the amenities that Ludlow offers. While updates are needed, the property offers a solid foundation with several key improvements already in place: numerous large, newer tilt-in windows, a standing seam roof, and convenient town water and sewer. A spacious detached garage provides ample storage and a potential workshop space, making renovations easier. This property is brimming with potential for a creative new owner to create their dream home.

Great location at the Adams House! This three-bedroom residence sleeps 10 and has a deck and windows, facing up the hill giving you super slope views! Features include: Updated kitchen with stainless steel appliances, granite countertops and farm-style sink, spacious living room with queen sleeper sofa and fireplace, primary bedroom suite with king-sized bed, bathroom with jetted tub, fireplace, bedroom with two queen beds, extra large foyer, and the lockout side has a bedroom suite with a king-sized bed and washer/dryer. Soak in the outside hot tubs after skiing or snow tubing. It’s a short walk to the Spring House to enjoy the spa or added exercise of swimming, a yoga class, or the weight room. Amenities include: indoor/outdoor pools, underground heated garage, use of the Spring House, Adventure Zone, and Mountain Coaster. Enjoy the comforts of true ski on/ski off lifestyle!

Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III (includes Christmas weeks for 2026). Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The Spring House, which offers an indoor and heated outdoor pool, fitness center, and spa. Other amenities include underground parking, slopeside hot tub, and conveniently located ski lockers, just to name a few. This great open floor plan features a fully equipped kitchen, jetted bathtub, gas fireplace, and lock-out capabilities. This floor plan sleeps 10 with 2 kings, 2 queens, and a queen sleeper sofa. Ownership allows you 13 set weeks a year with the opportunity for additional bonus weeks and RCI membership. Okemo is the perfect choice for year-round fun, including a picturesque lakes region, mountain biking, local shopping, dining, and more! Visit the Okemo real estate community today. ROFR

Jackson Gore Inn at Okemo Mountain Resort. Quarter Share Ownership, Unit 342/344 QIV is a true four-season destination offering a rare combination of slope-side convenience, year-round recreation, and resort-style amenities. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This 3 bedroom - 3 bath suite with lock-out, features a fully equipped kitchen, a balcony with valley views, 2 fireplaces, living area, dining area, and laundry. The king suite lock-out is like a luxury hotel room while the other side has living spaces and 2 bedrooms. You can sleep up to 12 people. Use one side and rent the other, use both sides, or rent both sides. Enjoy direct access to skiing and après, with proximity to the Okemo Valley’s lakes region, and Fox Run, an award-winning golf course. Jackson Gore features a vibrant calendar of signature events throughout the year, including winter favorites such as Let It Glow and the popular Summer Music Series. Amenities include a heated outdoor pool and hot tubs, a sauna, and a steam room located in the main Inn. Additional outdoor hot tubs are located outside of Adam’s House. A Spring House membership is included in your ownership, which offers a fitness center, locker rooms, sauna, playground, an indoor lap pool, children's pool, and hot tub. Additional features include an owner's library and office spaces, ski lockers, a tennis court, heated underground parking, outdoor fire pits, on-site dining, a ski shop, and easy access to ticketing, rentals, and lessons. The magic carpet is there for those just beginning their mountain adventures. The Adventure Zone offers year-round activities, including the Timber Ripper Mountain Coaster, Haulback Challenge Course, mini golf, and more. Visit the Okemo real estate community today. ROFR

Jackson Gore Inn Unit 335/337 Quarter I V : Beautifully appointed 3-bedroom, 3-bathroom unit located in the highly desirable Jackson Gore area, offering stunning slope views and a private deck to enjoy all seasons. Perfectly situated in the charming stone archway, this residence provides both convenience and a classic mountain feel. The spacious layout comfortably sleeps 12, making it ideal for large families or entertaining guests. Enjoy an open-concept living and dining area, generous bedrooms, and plenty of natural light throughout. Step outside onto the deck to take in the ski trail views and fresh mountain air. This unit is centrally located just steps from the pool, Owners Locker Room, and main amenities, making access effortless whether you're skiing, relaxing, or enjoying all the resort has to offer. A rare opportunity to own a prime slopeside property in one of the most sought-after locations—this is truly a must-see. Unit G Features: 3 bedrooms, King bed, 3 fixed Queen beds, Queen sleep sofa, Double sofa bed, full kitchen, 3 full baths washer/dryer, jetted bath tub, fireplace, entertainment center.

Charming and well-maintained 3-bedroom, 2-bathroom manufactured home on leased lot in a peaceful 55+ community. This inviting home features an open concept layout, high ceilings, and is filled with natural light pouring in through multiple skylights, creating a bright and airy atmosphere. Step outside to a new deck with an awning—perfect for enjoying warm summer days. The fenced yard is great for pets or gardening and includes a garden shed for extra storage. The roof was replaced just two years ago, providing added peace of mind. Conveniently located just minutes from Okemo Mountain and Fox Run Golf Course.