Private Pickleball Lessons & Coaches in Winchester, MA
Compare reviews, prices and open times, then book a private lesson online.
“I had taken five classes before Covid. I Wanted to get back into the game, this guy was incredible. He pointed out so many little catchphrases and his technical side was easy for me or any person to understand. He wasn't trying to dazzle me with his knowledge. He was a teacher, sharing his knowledge. Awesome lesson. Great class! Thank you.”H. E., student
About AyannWith four 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. I currently host clinics, camps for kids, and private lessons. I also travel for competition locally and nationally both as a player and a coach. Whatever it is you need, I’m here to help you find solutions! Let’s elevate your game!Go to profile99OutstandingTop rated
Ayann A.From $95 per lesson
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“I feel we made a lot of progress with technique”Sam M., studentAbout RonaldAs a passionate pickleball enthusiast and experienced tennis coach, I bring deep understanding of strategy, technique, and player development to the game. With years of coaching high-performance tennis players, my transition to pickleball was a natural evolution - one fueled by a love for competition, community and continuous learning. A major emphasis will be placed on placing the trainee on a path of self discovery for developing the student's ability to solve problems independently.Go to profile99OutstandingTop rated
Ronald J.From $65 per lesson
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“The perfect instructor to go to if you want thorough and robust lessons.”Somaly S., student
About PeterPeter embarked on a pickleball journey in July 2023 following a period of personal challenges. Introduced to the sport by a friend, pickleball quickly became a cornerstone of Peter's life, facilitating a remarkable 37-pound weight loss and reigniting a sense of passion and purpose. With a strong foundation in tennis, soccer, and ping pong, Peter seamlessly transitioned to pickleball, now leveraging this experience to help newcomers jumpstart their own love affair with the sport, promoting health, happiness, and community along the way.Go to profile99OutstandingTop rated
Peter P.From $85 per lesson
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“Jared was very patient and covered a wide range of skills to practice. Looking forward to lesson #2!”Marion K., student
About JaredWith over 13 years of tennis experience, background in exercise science, and physical therapy, I bring a deep understanding of racquet sports, footwork, strategy, and court awareness to the fast growing game of pickleball. While my pickleball journey is more recent, my extensive tennis background allows me to quickly translate proven skills such as precision volleys, serve technique, movement patterns, and shot selection into the pickleball setting.
I specialize in helping beginners and intermediate players build strong fundamentals and advance their game with clear, practical coaching. Whether you’re just picking up a paddle for the first time or looking to sharpen your consistency, I focus on making the game fun, approachable, and rewarding, while giving you tools to play with confidence.
If you’re ready to improve your pickleball skills with guidance rooted in years of racquet sport experience, I’d love to help you level up your game!Go to profile99OutstandingTop rated
Jared W.From $55 per lesson
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5.0 · 7 lessons · PickleballNext: Tomorrow, 6:00 AM
“I wanted to specifically work on resets and moving up to the kitchen at the right time and the lesson with Mike was really helpful. He was patient and the drills were excellent.”Dana P., student
About MichaelMichael, based in Haverhill, MA, is a dedicated pickleball coach passionate about teaching across the North Shore of Massachusetts and Southern New Hampshire. With experience coaching players of diverse skill levels, he has helped students prepare for the Special Olympics, facilitated corporate team-building events, and guided individuals in improving their DUPR ratings. Michael specializes in coaching beginners to upper-intermediate players, focusing on skill development and a deeper understanding of the game, ensuring every session is both effective and enjoyable.Go to profile97OutstandingTop rated
Michael C.From $115 per lesson
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“Charley was great! He truly catered to my skill level and related abilities.”Lynn B., student
About CharleyComing 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!Go to profile96GreatTop rated
Charley L.From $145 per lesson
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“Jon was great, skilled and knowledgeable. I really appreciate his calm mannerism. ”Donna S., student
About JonAs a former tennis player turned passionate Pickleball enthusiast, I've transitioned my skills, technique, and strategy into the world of Pickleball. I play nearly every day and have dedicated extensive time to mastering the game.
In addition to my racket sports background, I have experience teaching and coaching wrestling at the collegiate level. Now, my goal is to foster the growth of Pickleball and help individuals or groups enhance their skills, whether for casual play or competitive purposes. Looking forward to raising your game and having a blast on the court!Go to profile93GreatTop rated
Jon T.From $80 per lesson
“I have been having a great experience taking pickleball lessons from Jean. He’s calm and unassuming, not eager to show his skills and rather, teaches me basic skills that’re specifically for my needs. He gives me balls that are good trainings for my skill development, and alternating those with occasional instructions and tips, and more challenging balls. I look forward to gaining more skills at the next lesson!”Yune K., studentAbout JeanI'm a versatile athlete with experience in ping pong, badminton, tennis, and pickleball. Over the past 3 years, I've been actively engaging with beginners and intermediate players on the court, providing helpful tips and guidance. Let's work together to improve your game and take it to the next level!Go to profile92GreatTop rated
Jean P.From $65 per lesson
New coach · PickleballNext: Tomorrow, 6:00 AMFoss Park (Tennis Court) · 4.6 miDUPR CertifiedDUPR Certified
“I’m a beginner and was a little nervous about learning pickleball, but Joey made it fun and easy right from the start. He explained everything in simple terms and never made me feel overwhelmed. He was patient, encouraging, and kept the lesson relaxed while still helping me improve. By the end, I understood the basics, felt much more comfortable on the court, and was actually playing! I’d definitely recommend Joey to anyone who is new to pickleball and wants to learn the game, get better, and have fun doing it!”Ping, student · shared by Joey
About JoeyRPO Certified pickleball instructor with a 4.7 DUPR and a passion for helping players of all levels improve their game. I focus on fundamentals, strategy, and match play — tailoring lessons to each player’s goals, whether it’s mastering technique, boosting consistency, or improving court IQ. Patient, positive, and results-driven. Available for private lessons, group clinics, and tournament coaching. Contact me to raise your game.Go to profileJoey M.From $95 per lesson
New coach · PickleballNext: Tomorrow, 6:00 AMMills Field (tennis court) · 11.0 miPPR CertifiedPPR Certified
