Sweet Deals Abound (Some Literal): Winter Park's Best Shopping

Winter Park is well known as a place to spend and get spent in the Orlando area; the shady, moss draped oaks and charming brick streets of its affluent downtown are enough to lull even the tightest of wallets into satisfied submission. And while there are many upscale shops in which to drop a handful of pretty pennies, it's not essential for a memorable shopping experience. Case in point: Winter Park's Saturday Farmer's Market has been delighting locals and visitors for more than 25 years and some of them never buy more than a basket of berries or a cup of coffee. On Park Avenue, glittery shops like Alex & Ani offer beautiful, delicate pieces of jewelry at quite reasonable price points that carve out a bit of scratch for all kinds of charitable organizations. Gift shops abound, of course. Collectors of everything from ancient coins to pretty pebbles will enjoy exploring Ancient Artifacts & Treasures, while collectors of comics couldn't do better than A Comic Shop, where they're happy to help you find the greatest thing you haven't yet read. 


Looking for a certain, special something for the friend or loved one who truly has everything? How about the collector in your life? This unique shop could be the perfect place. Lovers of geology, rocks and minerals will find specimens to get lost amid, as will those who find fossils fascinating. Numismatists on the hunt for ancient monies, too, will find many about which to get excited. History buffs, too, will spot treasures – whether from ancient Asia or the Civil War era. This shop isn't just a shop, it's a micro-museum of nature and history – and absolutely worth a peek.

Recommended for Winter Park's Best Shopping because: Whether you're an avid collector or simply on the hunt for a unique piece, Ancient Artifacts & Treasures is an excellent hunting ground.

A.D.'s expert tip: Shopkeeps here know their stuff so well, they're often invited to share their knowledge with school groups (and are more than happy to do the same with customers).

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Are you ready to discover universes beyond that of Marvel and DC? Winter Park's A Comic Shop is just the place in which to do so. While well versed in everything from Avengers to X-Men, staffers here will be happy to learn your likes – or those for whom you're buying – and make suggestions to suit. What's more, this little local has an on-site lounge and event space – the Geek Easy – where readers, gamers and the like are welcome to sit awhile and enjoy a cold beer or even nerdy karaoke if you come on the right night. Connect with the shop's Facebook page to keep abreast of what's going on.

Recommended for Winter Park's Best Shopping because: You don't have to know comics to shop for the comic book lover in your life. A Comic Shop is welcoming to vets and noobs.

A.D.'s expert tip: You'll certainly find fun collectibles, but the focus here is on reading.

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This quirky independent toy store makes shopping on Park Avenue that much more fun; kids and adults are invited to give many of its wares a try. Lighten Up boasts shelves, racks and cases of unique toys, games and crafts; much of its stock is geared toward learning and a friendly and knowledgeable staff is on-hand to guide you. The Kites and other collectibles abound, along with a selection of "old-fashioned" toys – as much a delight to adults as their children and grandchildren. You won't find the usual chain-store items in here, though prices range from pocket change on up, so kids can easily find a trinket for their allowance money if mom or dad say it's okay.

Recommended for Winter Park's Best Shopping because: New-fangled to old-timey, the toys and other fun items at Lighten Up make it a wonderful place not only for shopping, but nostalgia.

A.D.'s expert tip: Make this shop part of a larger Park Avenue exploration and budget time for more, even if it's just window shopping.

Read more about Lighten Up! →


If you appreciate world arts and crafts from the likes of Latin America, Asia and the Middle East, if you enjoy the boho-hippie aesthetic when it comes to jewelry, if you have a penchant for incense, you might want to check out Kathmandu, a charming Nag Champa-infused shop on the far end of Winter Park's Park Avenue. Great for gifts of all sorts – from wearable baubles to lovely home furnishings. It's an altogether different shop from most on tony Park Avenue. While many boutiques seem better suited to the purse-dog set, this one – with its Hindu prayer shawls, carved Buddhas and Fair Trade sensibility has a broader, earthier appeal.

Recommended for Winter Park's Best Shopping because: Knowledgeable staffers and a sandal-and-patchouli-friendly environment permeate the vibe (and possibly your clothes if you linger too long) at this exotic Winter Park shop.

A.D.'s expert tip: Kathmandu is browse-friendly. Ask them about their downtown location and sister business: Kush Hookah Lounge.

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If you're visiting Orlando, a furniture purchase might not be in the cards, Luckily, at Adjectives Market (which has additional locations in both Altamonte Springs and Winter Garden), home decor purchases need not require a U-Haul. This carefully curated shop is filled with an array of new, vintage and highly unique handcrafted items, throw pillows to planters, bookshelves to bookends, end tables to tableware and well beyond. Local artists' wares and phenomenal finds from your grandparents' garage mix beautifully with unique new pieces and even small gift items.

Recommended for Winter Park's Best Shopping because: Adjectives Market is the sort of place where you may not see the same thing twice. Love it? Snatch it up!

A.D.'s expert tip: Don't just buy a unique piece, learn to make your own! Adjectives Market offers regular classes that educate the DIY crowd on everything from furniture refurbishment to faux finishes to jewelry making.

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You may already know Rifle Paper Co. Why? This stationery and lifestyle brand has paired with some heavy hitter companies since its launch in 2009: Le Sportsac, Paper Crown, Puffin Books, and the list goes on from there. But its lovely little HQ is right here in Winter Park, FL. Chic and upscale, it fits right into the neighborhood, and seeing all its wares in one place, plus getting a glimpse into the creative works, is a little like peeking behind Oz's curtain. Calendars, cards, art, address books ... beauty and elegance abounds, as does the option for custom items. If letter writing has fallen away from your life, this is the store that might finally make you quit social media and spend $100+ on a fancy new pen.

Recommended for Winter Park's Best Shopping because: This divine little shop is ground zero for elegance in paper products, whether you're looking for simple blank cards or custom invitations.

A.D.'s expert tip: Follow them on social media to keep an eye out for Rifle's sidewalk sales for some phenomenal deals on beautiful merchandise.

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Shoppers will find all that glitters at Alex & Ani's Winter Park base of ops, where beautiful bangles beckon and baubles imbued with empowering vibes bling. Gifts abound for the jewelry lover in your life, of course, but selfish shoppers can splurge guilt-free, as a portion of all the sales here go toward a host of charities aiding causes ranging from autism to heart disease to bringing clean, fresh water to communities that need it. Creative and calming designs are surprisingly affordable and ever-so-spiritual, from Buddha to Aphrodite and beyond. If you've never seen their inventory, it's time you checked it out.

Recommended for Winter Park's Best Shopping because: With styles suitable for just about anyone and prices that are surprisingly wallet-friendly, Alex & Ani is definitely worth a peek.

A.D.'s expert tip: Check their Facebook page for themed events that combine snacks, drinks and charity with sale prices!

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Chocoholics beware. While the many tempting shops of Park Avenue are rife with goodies for your home, office, closet or jewelry box, Peterbrooke's could head straight to your hips! We dare you to escape the gravitational pull of this sublime chocolatier, where the smell alone might satisfy your sweet tooth if not for the high-quality visuals on display everywhere, from the bins where weight-sold chocolate-covered malt balls, toffee bits, nuts and more tempt to ridiculous-decadent creatives like the "broissant" (Peterbrooke's take on the cronut, a gooey-rich affair that seems pulled from the deepest dreams of Willy Wonka himself). Colorful, delicious handmade treats abound. And yes, they have boxed assortments for the folks back home.

Recommended for Winter Park's Best Shopping because: Confections of the highest order are what you'll find at Peterbrooke, from truffles to chocolate-dipped goodies to enormous treats on a stick.

A.D.'s expert tip: Is it hot out? Try Peterbrooke's gelato and walk it off as you peruse the neighborhood.

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While some vintage/consignment shops have a tendency – charming in most cases – to remind you of your Great Aunt's attic, Avalon is the utter antithesis. It's clean, modern, airy and bright with easily navigable racks just crammed with second-hand goodies – men's and women's – much of which is brand name. Find deals on everything from Air Jordan to Zara, Tory Burch to True Religion, Farragamo to French Connection and loads, loads more. And just because they've got an eye for brands doesn't mean you won't happen upon a one-of-a-kind find or genuine vintage piece. Friendly staffers are happy to point you in the right direction.

Recommended for Winter Park's Best Shopping because: Who doesn't love a second-hand bargain? Avalon's spacious, clean environment makes the hunt much easier.

A.D.'s expert tip: Buying hours are 11-7 Monday through Saturday, noon-5 on Sundays.

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Downtown Winter Park is charming from end to end and few places capture that community essence quite as wonderfully as its Saturday Farmer's Market, where orchids bloom, a rainbow of fresh produce sets your inner chef running rampant with playful ideas and the smell of croissants, garlic fries and other fresh-made goodies tempt at every turn. If you don't come with anything in mind, it's good to at least come hungry! Held in and around the city's beautiful old train depot, charm abounds and when you're done with your market perusal, the shops and attractions of Park Avenue are literally steps away.

Recommended for Winter Park's Best Shopping because: For locavores and lovers of small-town charm, you can't do better than this market, a Winter Park institution for more than 35 years.

A.D.'s expert tip: Come hungry! This is a charming place for coffee and/or breakfast on a beautiful Saturday morning.

Read more about Winter Park Farmers' Market →


Meet A.D. Thompson

Amy Drew has spent nearly three decades as a professional writer and roughly half her life as a Floridian. The words, she has found, come easier with bare feet and rum.

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