Best Barber Shops In Windermere

Below are the best 6 barbershops in Windermere picked by BestProsInTown

9AM - 7PM

4750 The Grove Dr Ste 132, Windermere
Hammer & Nails- Orlando Windermere Barbers

“Love this place!! Everyone is incredible! Kapi, Isha, Jess! Great cuts, service, nails, facial! Thank you everyone!!!“

4.9 Superb154 Reviews

9AM - 6:30PM

7848 Winter Garden Vineland Rd #108, Windermere
V's Barbershop - Windermere Barbers

“Had a great experience at V’s Barbershop. The barbers are extremely professional, attentive, and take their time to make sure everything is done right. You can tell they really care about their craft and their clients. Highly recommend if you’re looking for quality service.“

4.8 Superb174 Reviews

9:30AM - 7PM

13796 Bridgewater Crossings Blvd #1080, Windermere
The Village Barber Shop Barbers

“Oliver is amazing with kids! He is patient, professional, and always makes my sons feel comfortable during their haircuts. He pays attention to every detail and consistently does a great job. The cuts always look clean and stylish, and my boys actually enjoy going to see him. Highly recommend Oliver to any parent looking for a talented and reliable barber!

— Eloisa & Family 😊“

4.9 Superb108 Reviews

8AM - 11PM

9100 Conroy Windermere Rd STE 200, Windermere
Barber Luxe Mobile Barbershop Barbers

“Barber Luxe completely exceeded my expectations. From the moment they arrived, it was clear this was a high-end operation. On time, professional, and they kept a clean working area throughout — no mess, no stress.

The attention to detail was next level. Every cut, every line — nothing was rushed.

Price was great, well worth it. Way more value than a traditional barbershop when you factor in the convenience of not leaving your home.

I’ve already recommended Barber Luxe to two friends. If you’re on the fence, just book it. You won’t regret it.“

5 Superb63 Reviews

9AM - 9PM

13500 Summerport Village Pkwy, Windermere
Hair Cuttery Barbers

“I’ve been visiting this location for 10 years now and won’t go anywhere else because of my hair stylelist – Andy. In 10 years, I’ve never been disappointed.“

4.5 Superb130 Reviews

11AM - 6PM

6536 Old Brick Rd Unit 110 Studio 25, Windermere
StayFresh StayBlessed Studio Barbers

“Xavy is awesome. Professionally, he is a perfectionist. His work is consistently on point and he listens to what you want, and executes! He is also, as a bonus, an awesome human. He's so personable it's like hanging with your best friend. I won't go elsewhere!“

5 Superb7 Reviews