Private Lessons & Coaches in Milford, MA

Coming from a background in ping pong, Charley quickly became fond of pickleball during the tail end of COVID, gathering people from his church to play. Years later, as a World Pickleball Tour National Champion (January 2025) with a 4.5+ DUPR rating, Charley has reached the pinnacle of amateur competitive pickleball. With a Massachusetts teaching license and two years of coaching experience, he is passionate about helping players of all skill levels and age groups refine their techniques and develop a deeper love for the game. Additionally, he leads a weekly group and provides extra repetition with a ball-serving machine to maximize practice and improvement. Let’s take your pickleball game to the next level—let me know when you’re ready to get started!

"Very professional and helped my game out greatly after only one lesson.

I started playing tennis in Haiti at the age of two. As a junior player, I participated in and won numerous tournaments. During my four years at Brockton High School, I was frequently featured in the Brockton Enterprise newspaper for my achievements. I continued my tennis career at Salem State University, winning two championships and participating in the NCAA tournaments twice. My accolades include being a 4-time First Team All-Conference honoree, and I am currently among the top 10 players with the most games won in Salem State history. I have been coaching for three years, working with players of all levels.

"All the feedbacks from coach Roni helps me fixing all my little mistakes that can become long term habits. Coach lets me take my time and go step by step to make sure I’m not rushing into it.

I love pickleball and the community it’s given me. Having learned from incredible mentors, I’m ready to pay it forward. A former 4-year HS tennis player, I’ve since competed in APA tournaments across all formats. My coaching is collaborative yet direct—I focus on technical skills to sharpen strengths and fix weaknesses. I offer flexible teaching tailored to what works best for you, always balancing improvement with genuine fun. All levels are welcome—let’s get on the court and level up!

With two years of coaching experience and competing as a sponsored athlete, I bring a unique perspective to pickleball instruction. My passion is helping players of all levels unlock their full potential on the court. Let's elevate your game! Please message me about any inquiries, the more time I have to prepare the better as I also play in tournaments and so my schedule can fill up quick!

"Ayann really honed in on form and gave great tips for defensive strategy. Excited to my next 2 lessons- I think Ayann is really going to help me elevate passed 3.5

James Crosson has had the prestigious honor of being selected out of 300 participants to become one of the 60 certified coaches by DUPR’s exclusive coaching program. James is registered as National Professional Pickleball DUPR coach, a National Pickleball Professional with the International Registry of Pickleball Professionals, A National Professional with the International Coaches Institute, A professional with the RPPk Registery of Pickleball Professionals, and has worked with the Tyson McGruff coaching program to deliver excellence in all categories of coaching Pickleball. For over 8+ years James has become an avid Pickleball player, and his love for the game is only exceeded by his passion for teaching others how to improve in all aspects of their Pickleball game! From teaching beginners to excel quickly into the Pickleball world, to teaching advanced techniques and strategies to already established players to improve on their game, there is nothing James won’t be able to show you! James is extremely personable to make you feel comfortable in your learning process, and his methodology is that learning Pickleball should be a fun experience instead of feeling like a chore. James is an all-around athlete and has a strong tennis background from 6 years at the Newport Tennis Hall of fame. He fell in love with Pickleball, and was the founder of the very successful Fall River Pickleball Group. James is very competitive and is constantly playing in Pickleball tournaments against some of the best players in the Rhode Island and Massachusetts area. To ignite your passion in beginning your Pickleball journey, or to overcome the obstacles holding you back from being the best Pickleball player.

"James quickly taught me how to play so I could go out on the courts and start playing in open plays without feeling nervous! He gave me the ground work to start playing and learning on my own so I can continue to play until I need his guidance again! Awesome coach and fast teacher!

As an experienced golf instructor, I am committed to fostering a love for the game. I I player competitively at the NCAA Division I level. I'll equip you with the skills and strategies needed to improve your game and enjoy your time on the golf course . Let's refine your technique and unlock your golfing potential!

"Dillon was awesome! Super knowledgeable and gave me great tips. Would highly recommend taking a lesson with him.

With 45 years devoted to tennis, I blend college coaching experience with personalized instruction. My passion is fostering skill development, sportsmanship, and a lifelong love for the game.

"Bill is responsive to my texts to schedule the appointment. He knows what my kids need to do. His drills are effective and fun. He is also kind to parents as well. Overall, he made a positive impact on my kids' tennis journey. Highly recommended.

I’m Cristian Tello, a Boston-based photographer passionate about helping people connect with the art of photography—no matter where they’re starting from. Whether you just picked up a camera or you’re looking to sharpen your creative voice, I work with photographers who want to grow both technically and creatively. My coaching is built around seeing with intention, staying curious, and learning to tell stories through your lens. It’s not just about gear or settings—it’s about slowing down, observing more, and building a skill that stays with you for life. If you’re a beginner with an interest, you’re in the right place.

"I learned so many new things ! Great vibe great energy! highly recommend!

Experience coaching youth baseball as a pitching coach. Individual workout sessions w/ semi-pro football players & baseball athletes. Non athletes I train as well for desired fitness goals. I sculpt customized programs that blend proven techniques w/ individual aspirations. My passion lies in empowering clients to surpass their fitness goals. I train kids to adults 8+. My teaching styles are individualization, verbal/tactical cues, visual demonstration & adaptive coaching. -Online demonstrations

"Davonte's attention to detail and enthusiasm for training motivated me throughout multiple sessions, keeping me in the best physical shape while also enhancing technique and mobility in my sport of focus, baseball. He's a Great active listener and focused on the exercises & workouts that helped me mentally and provided positive reinforcement. I would recommend Davonte for Anyone! Young or adult.

Andie has over 15 years of coaching and playing experience. Born in Kingston, Jamaica and migrated to New England in 2011 and began coaching professionally; while also working in Banking and Finance as a Mortgage Loan Officer. She is RSPA/USPTA CERTIFIED NewTennis Player and USTA SafeSport Certified Coach. Wheelchair Accessible Coach. Her tennis game is inspired by the likes of Monica Seles, Venus Williams and Pete Sampras to name a few. She focuses on fun drills with structured sessions to enable personal growth and expanding the reach of the game. Her knowledge comes from decades of playing and teaching alongside all levels of players. She is passionate about sharing the game with everyone!

"The lesson with Andie was pretty helpful, especially because the drills were customized based on my weaknesses mid drill, which I appreciated. Though I still need more practice to feel really confident, I think repeating this kind of tailored approach could make a difference. Still, I’d be open to trying another lesson to see how much I can improve with her guidance.