Prosperous Penny

4.7
9 reviews

About

BarCocktail LoungeWine Bar
Unwind in style at Prosperous Penny, an intimate bar in Westlake Village offering handcrafted drinks, fine wines, and a curated selection of premium spirits. Located within Four Seasons Hotel Westlake Village, this elegant lounge exudes classic charm with a warm, inviting ambiance. Guests can enjoy expertly mixed cocktails, a well-stocked wine bar, and elevated small bites in a sophisticated yet relaxed setting. Whether you're looking for a refined night out or a cozy spot to sip and socialize, Prosperous Penny stands out among the best bars in Westlake Village for a truly memorable experience.

Details

  • Dine-inAvailable
  • DeliveryNot available
  • TakeoutNot available
  • Accepts reservationsNot available

Location

Prosperous Penny
2 Dole Dr, Westlake Village, CA
91362, United States

Hours

Reviews

4.7
9 reviews
5 stars
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0
1 star
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  • CR
    Cheree Ramon
    Nov 10, 2025
    4.0
    Felt nice to sit in this swanky, dimly-lit, beautiful bar. The live music was great and not too loud to also enjoy conversation. Charcuterie was decent and came with a delicious quince treat.
  • AA
    Alana
    Oct 31, 2025
    5.0
    Tucked away behind a blue door, is a classy speakeasy-themed bar with smashing decor, fabulous drinks, and mixologists with finesse. This clean, sleek gem of a place is my favorite place to have a unique cocktail and bites. The lighting is cozy and on certain nights they have live music. Go, check it out. You can stop by the main restaurant and/or step back in time and enjoy this spiffy and sophisticated spot. Love it.
  • AC
    Alan Ching
    Nov 18, 2023
    5.0
    The food and service is always great. We had a fantastic appetizer sampler and highly recommend it.
  • MP
    Mary Powers
    Jul 29, 2023
    5.0
    Her MajestyπŸ‘‘-- the perfect libation for a "royal lady"!πŸ’Ž Lovely, tasty, and light!πŸͺ­ Thank you, Tate!πŸ‘πŸ˜Ž PS: Prosperous Penny DEFINITELY needs to be open more days!!πŸ₯‚πŸΈπŸΉ
  • DS
    Deepa Samuel
    Aug 5, 2019
    5.0
    If it's possible to up the ante on 'grabbing a drink', Prosperous Penny has succeeded. Whether you are local or visiting from out of town, the personalized service you receive here is what is key. Before the end of your visit, the bartenders will know your choice of libation, know your name and remember more about you than you realized you'd told them! I challenge you: if you are an Old Fashioned person, ask Bob for the Smoked Old Fashioned. Or try the Apple infused Tequila Old Fashioned. Broaden your martini borders: try the Cucumber Martini. Likely the best I've had: so smooth I don't even realize I should have stuck with one! If you are looking for someone to talk shop (alcohol shop), Bob is the conversationalist you hope to find behind the bar at a place like PP. The patrons are just as conversational as the staff, looking to enjoy an evening out and make friends to join them back for another night at PP. Cole and Austin are wonderful servers. I don't think I have ever seen them frown and they are always on their toes. The are also very knowledgeable, don't be shy to ask them for their opinion! George and Sen are also ensuring that both staff and patrons alike are well-taken care of. It's good to see a team working so well together to make the experience of the PP a memorable evening. Thank you Austin, Bob, Cole, Eric, George and Sen!

Frequently Asked Questions About Prosperous Penny

What signature cocktails are available at Prosperous Penny?

Her Majesty, Barrel Aged Vieux Carre, Chi-Tini.

Does this bar in Westlake Village offer a selection of local or international wines?

Yes, Prosperous Penny offers a robust selection of local and international wines.