5401 Bay Shore Rd, Sarasota, FL 34243
The Circus Arts Conservatory and The Ringling team up for Sarasota's beloved summer tradition, with world-class circus artists performing in the air-conditioned, jewel-box Historic Asolo Theater. Tickets are $20 for adults and $15 for kids 12 and under, and adding the Circus Museum is just $5 more.
Summer Circus Spectacular website1265 First St, Sarasota, FL 34236
Florida Studio Theatre opens its summer mainstage comedy about Ralph, a widower whose chance meeting with the elegant Carol turns into an unexpected second chance at love. Warm, witty and about 1 hour 50 minutes with intermission. Tickets through the FST box office at 941-366-9000 — a good excuse to make a night of it downtown.
The Last Romance websiteLemon Ave & Main St, Sarasota, FL 34236
Downtown Sarasota's Saturday-morning staple: fresh produce, flowers, baked goods, coffee and local makers along Lemon Avenue and Main Street. Free to browse, dog-friendly, and the easiest way to see downtown at its liveliest — go early to beat the July heat.
Sarasota Farmers Market website948 Beach Rd, Siesta Key, FL 34242
Siesta Key's famous Sunday-evening ritual since 1996: drummers, dancers and hundreds of onlookers gather on the quartz sand south of the pavilion as the sun drops into the Gulf. Free, all ages, and quintessentially Siesta — arrive early for parking.
Siesta Key Drum Circle website400 Ben Franklin Dr, Lido Key
Siesta's quieter sibling, five minutes from St. Armands Circle. Wide white sand, a classic mid-century pavilion with a pool and concession stand, and far fewer crowds. This is the beach you walk to from dinner on the Circle.
Ryan's take: Luxury travelers: book sunset at a Circle restaurant, then walk the sand after. It's the lifestyle preview for every St. Armands and Lido condo buyer.
Longboat Key
Longboat's wild north tip: a driftwood 'boneyard' beach where weathered trees lie bleached on the sand and a walkable sandbar arcs into Longboat Pass. Reachable on foot from the Broadway access at low tide, or by boat — locals raft up on the pass side.
Ryan's take: Go at low tide for the full sandbar. This is the photo that makes people move here.
948 Beach Rd, Siesta Key
The famous one — 99% pure quartz sand that stays cool underfoot, repeatedly ranked the #1 beach in America (Dr. Beach 2011 & 2017, TripAdvisor's U.S. #1). Year-round lifeguards, 800+ free parking spaces, playground, concessions, tennis and volleyball.
Ryan's take: In season, be in the lot before 10am or ride the free Siesta Key Breeze trolley. Families: the lifeguarded zones and shallow shelf here are the safest swim on the Key.
2201 Ben Franklin Dr, Lido Key
Four bodies of water meet at Lido's south tip — Gulf, Big Pass, Brushy Bayou and Sarasota Bay. Kayak the mangrove tunnels (guided tours launch here), picnic under Australian pines, and watch boats run the pass with Siesta Key across the water.
Ryan's take: The mangrove-tunnel kayak tour is the single best family adventure on the Keys. Swimmers: stay clear of Big Pass — the current is real.
Ocean Blvd at Avenida Navarra, Siesta Key
The village beach access — a short barefoot walk from Siesta Key Village's restaurants and shops straight onto the quartz sand. Small free lot plus street spots.
Ryan's take: Lot fills by 9am in season. Park once in the Village, hit the beach, then walk to lunch — best car-free day on the Key.
Point of Rocks Rd, Siesta Key
Crescent Beach's south end hides Point of Rocks — limestone outcroppings with the best snorkeling on the Key. Calmer, less crowded sand than the main beach.
Ryan's take: Bring water shoes and go at slack tide for clear snorkeling. Street parking is scarce — arrive early or bike down.
8918 Midnight Pass Rd, Siesta Key
The Key's laid-back south-end beach: darker, coarser sand famous for shelling, a shaded playground, picnic shelters, volleyball, and a public boat ramp onto Little Sarasota Bay. Rarely crowded.
Ryan's take: Best shelling after a storm. The adjacent Turtle Beach Campground is the sleeper way to test-drive island life.
North end of Benjamin Franklin Dr, Lido Key
Lido's secluded stretch — no lifeguards, no concessions, just quiet white sand and sea oats a ten-minute walk from St. Armands Circle. The locals' escape hatch.
Ryan's take: Strong currents near New Pass — walk it, wade it, but save the real swimming for the lifeguarded main beach.
100 Broadway St, Longboat Key
The main public doorway to Longboat's north-end sand and the walk out to Greer Island. Real parking lot (rare on Longboat), short boardwalk, miles of uncrowded beach in both directions.
Ryan's take: This is the access locals use. Whitney Beach's wide, empty stretch runs south from here.
Gulf of Mexico Dr — General Harris St / Neptune Ave / Mayfield St, Longboat Key
Longboat keeps its beaches quiet by design: a string of small, marked accesses off Gulf of Mexico Drive (General Harris, Neptune, Mayfield, Gulfside Rd) with a handful of spaces each — and essentially private Gulf frontage once you're on the sand.
Ryan's take: If the first access is full, the next is a minute away. This scarcity of parking is exactly why Longboat beaches feel private — and why owners love it.
4052 Gulf of Mexico Dr, Longboat Key
Longboat's family hub on the bay side: playground, splash pad, kayak launch, tennis and pickleball, dog parks, and picnic lawns looking across Sarasota Bay.
Ryan's take: Launch a kayak an hour before sunset and paddle the bay side — calm water, mangroves, and skyline views.
100 Gulf of Mexico Dr, Longboat Key (south tip)
34 acres of trails and boardwalks over lagoons and mangroves at Longboat's south tip, with New Pass and the Lido skyline across the water. Ospreys, herons, and the occasional manatee in the lagoons.
Ryan's take: Pair it with lunch across the bridge — the preserve sits at the foot of the New Pass bridge to Lido.
Shell Rd, north Siesta Key
The locals’ secret at the Key’s north tip — a quiet shelling cove facing Big Pass with downtown skyline views and rarely more than a dozen people. No facilities, all serenity.
Ryan's take: Street parking only and blissfully unknown — the "north Key insider" card in any buyer conversation.
South of Turtle Beach (walk-in only)
Walk south from Turtle Beach and the crowds simply end — old Midnight Pass territory, dolphins working the bar, and sand you’ll share mostly with shorebirds.
Ryan's take: The south Key’s wild side — pairs perfectly with a Turtle Beach condo showing.
5 Bayfront Dr, Sarasota
Downtown's front porch on the bay — sailboats, a splash fountain, and the best sunset photo in the city framed by the Ringling Bridge.
Ryan's take: Walk the bridge at golden hour — the unofficial test-drive for downtown condo life.
1534 Mound St, Sarasota
Bayfront gardens famous for orchids and epiphytes, plus a banyan grove and a tree-canopy walk. A green exhale minutes from downtown.
Ryan's take: The downtown campus and the Spanish Point campus to the south are both worth it.
1600 Ken Thompson Pkwy, City Island
Sharks, manatees, and sea-turtle research on City Island — a genuine working marine lab, not just a tourist tank.
Ryan's take: The big public aquarium is now Mote SEA out by UTC — this City Island campus remains the working research lab. Watch what happens to this waterfront site.
State St & Lemon Ave, Downtown
70+ vendors take over downtown every Saturday morning — produce, flowers, prepared food, and live music. The week's best free morning out.
Ryan's take: Saturdays 7am–1pm. Grab a coffee, do a loop, then walk Main Street while it's quiet.
61 N Pineapple Ave, Sarasota
A restored 1926 Mediterranean Revival gem anchoring the downtown arts district — a big part of why Sarasota punches above its weight culturally.
Ryan's take: The arts calendar is a genuine value driver downtown; it's the first thing relocating buyers fall for.
St. Armands Circle, Sarasota
An open-air ring of boutiques, galleries, and restaurants between downtown and Lido Beach. Equal parts shopping trip and people-watching.
Ryan's take: Living within a golf-cart ride of the Circle is its own micro-market — ask me about it.
5401 Bay Shore Rd, Sarasota
John Ringling's 66-acre bayfront estate: a world-class art museum, the Cà d'Zan mansion, and a circus museum. The single best rainy-day plan in town.
Ryan's take: Mondays the art galleries are free. Give yourself half a day — people always underestimate it.
777 N Tamiami Trl, Sarasota
The unmistakable purple seashell on the bayfront — Broadway tours, concerts, and comedy with the bay shimmering through the lobby glass.
Ryan's take: The surrounding bayfront is slated for major redevelopment — a long-game reason to watch nearby addresses.
140 University Town Center Dr, Sarasota, FL 34243
Sarasota's premier shopping destination: Saks Fifth Avenue and 100+ stores and restaurants in the mall, ringed by an entire retail district (UTC), Nathan Benderson Park and Mote SEA. Five minutes off I-75 at University Parkway.
Ryan's take: This corridor is the growth engine of the Sarasota-Bradenton line — retail, dining and entertainment that new-construction buyers east of I-75 use daily.
The Mall at University Town Center websiteNorth end of Nathan Benderson Park, University Town Center Dr, Sarasota, FL 34235
Mote Marine's new flagship: a 110,000+ sq ft aquarium at Nathan Benderson Park with roughly a million gallons of exhibits, sharks, sea turtles, otters and hands-on STEM teaching labs. The area's biggest new family attraction, right off I-75 by the UTC mall.
Ryan's take: Pair it with a lap around Nathan Benderson Park — world-championship rowing venue, 3.4-mile flat loop, and the best people-watching on the east side.
Mote SEA (Science Education Aquarium) website195 University Town Center Dr, Sarasota, FL 34243
Two Tiger Woods-designed 18-hole putting courses with a full restaurant and bar, ice cream shop, outdoor games and a playground. Golf entertainment the whole family actually plays — no tee time required.
Ryan's take: Go at sunset — courses are lit, drinks flow, and the Florida evening does the rest. Book online on weekends.
PopStroke Sarasota websiteRuns Turtle Beach to the Village, daily
Free open-air trolley looping the whole island every 20–30 minutes, Turtle Beach to the Village. The answer to "where do we park?" is: you don’t.
Ryan's take: Changes the condo math — a mid-Key unit plus the Breeze equals village life without village parking.
1265 Old Stickney Point Rd, Siesta Key
Full-service marina at Stickney Point — wet slips, dry storage, fuel and a straight shot out Big Pass to the Gulf. The island’s boating hub.
Ryan's take: Slip availability is the first question every boating buyer should ask — start here.
1249 Stickney Point Rd, Sarasota (bridge east end)
Since 1957: boat rentals, guided fishing charters, kayaks and the tackle shop that knows where the snook are. The easiest on-ramp to Siesta’s boating life before you own one.
Ryan's take: Rent-before-you-buy: a season of CB’s rentals tells you exactly which boat (and slip) to purchase.
CB's Saltwater Outfitters website205 Canal Rd, Siesta Key Village
The Village’s gourmet grocer — real butcher counter, prepared meals, good wine, beach picnic fixings. Solves "is there anywhere to shop on the island?" in one visit.
Ryan's take: Daily-life proof for buyers: dinner ingredients without crossing a bridge.
444 Reid St, Siesta Key
Florida’s second-oldest independent school, founded 1924 — the pre-K–6 campus sits right on the north Key under the oaks. Families really do walk their kids to school on this island.
Ryan's take: A top-tier school ON the Key is the family-buyer unlock most visitors never discover.
Out-of-Door Academy (Siesta campus) website1445 2nd St, Sarasota, FL 34236
Craft beer taproom, wine and bottle shop. Light bites, meet-up for run/walk clubs and NY flavor (bagels & NY Giants) Food style: NY Bagels, light handhelds Vibe: Lively Price: $$-$$$ Good for: Drinks, Brunch, Social Run Club Meet-up Book: Visit website Website: https://99bottles.net
99 Bottles - Craft Beer & Wine Bar website550 Central Ave, Sarasota, FL 34236
Artisan Cheese Company curated cheese shop and bistro. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: Café, bakery & light bites Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, visitors, and locals Book: Visit website Website: https://artisancheesecompany.com
Artisan Cheese Company website27 Fletcher Ave, Sarasota, FL 34236
Wood-fired Neapolitan pizza and Italian classics. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: Italian, pizza & pasta Vibe: Casual, welcoming Price: $-$$ Good for: Families, casual dinners, groups Book: Visit website Website: https://bavarospizza.com
Bavaro’s Pizza website1287 1st St, Sarasota, FL 34236
Currently Closed for construction - confirm with restaurant on re-opening. Fine dining with French and Continental cuisine with open air patio. Food style: French & European cuisine Vibe: Upscale, Casual Price: $$$ Good for: Breakfast, brunch, casual meet-ups Book: Visit website Website: https://bijoucafe.net
Bijou Café website19 S Lemon Ave, Sarasota, FL 34236
Farm-to-table comfort food and craft cocktails. A relaxed, exposed brick vibe with indoor - outdoor seating in heart of Downtown. Fun people watching at the bar and walking by the sidewalk downtown. Food style: American & global fare Vibe: Lively Price: $$-$$$ Good for: Drinks, Date night, Lunch or Brunch Book: Google Profile Website: https://bocasarasota.com
Boca Sarasota website1528 State St, Sarasota, FL 34236
Texas-style BBQ and whiskey bar. Great happy hour specials in the heart of State Street - Downtown Sarasota. Indoor-outdoor dining with live music and casual, rustic vibe, fun early-evening spot.. Food style: BBQ & Southern-inspired Vibe: Lively Price: $$-$$$ Good for: Drinks, live music, happy hour, people watching Book: Visit website Website: https://brickssmokedmeats.com
Brick’s Smoked Meats website1298 N Palm Ave, Sarasota, FL 34236
Italian café with pastas, wine & pastries. Lively atmosphere downtown as a popular spot for drinks, dinner and desserts with European vibe. Food style: Café, bakery & light bites Vibe: Casual Price: $$-$$$ Good for: Brunch, Italian, Drinks, Dessert Book: Visit website Website: https://cafeepicure.com
Cafe Epicure website431 St Armands Cir, Sarasota, FL 34236
Mediterranean-style dining on St. Armands (formerly Cafe L'Europe) a hip, breezy space with indoor-outdoor dining, exposed-brick and coastal touches. A lively but relaxed ambience that works well for brunch, date nights, or casual dinners on the Circle. Food style: Mediterranean, small plates/shareables Vibe: Upscale, Casual Price: $$$ Good for: Breakfast, brunch, date night, drinks Website: https://cafeonstarmands.com/
Cafe on St Armands website1548 Main St, Sarasota, FL 34236
Lively bourbon, craft cocktails & tapas. Traditional bar setting with indoor-outdoor seating and live music on the weekends. A popular spot on Friday nights! Food style: Small plates & bar bites Vibe: Lively Price: $$-$$$ Good for: Happy hour, drinks, date night, late-night meetups Website: https://caskandalesrq.com
Cask & Ale website411 St Armands Cir, Sarasota, FL 34236
Historic Cuban-Spanish with Mediterranean-style dining rooms and a lively outdoor patio - ideal for casual dinners or a sip of sangria in-between shopping on the Circle. The 1905 Salad and cuban sandwich are world-famous. Food style: Cuban-Spanish, Salads and Tapas Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, drinks, lunch Book: OpenTable reservations
Columbia Restaurant website1553 Main St, Sarasota, FL 34236
C'est La Vie is an authentic French bakery and café that feels like a slice of Paris in the heart of downtown Sarasota. It's a quintessential spot for breakfast, known for amazing croissants, fresh crepes, and traditional French flair served from early morning onward. Enjoy a relaxed café vibe as downtown Sarasota wakes up around you. Food style: Café, bakery & light bites Vibe: Casual Price: $$-$$$ Good for: Breakfast, brunch, casual meet-ups, bakery Book: Visit website Website: https://cestlaviesarasota.com
C’est La Vie website700 Benjamin Franklin Dr, Sarasota, FL 34236, USA
At Drift Kitchen & Bar you'll find elevated Gulf-view dining perched on the 8th floor of Lido Beach Resort, offering panoramic, floor-to-ceiling views over Lido Beach and Sarasota's coastline. The menu highlights fresh seafood, house-made pastas, brick-oven pizzas, and contemporary American dishes that blend coastal flavors with a refined, resort-style touch. But in the end, you're here for the views and the resort feel. Open to the public Food style: Seafood & coastal American Vibe: Lively Price: $$-$$$ Good for: Drinks, date night, breakfast, brunch, dinner Book: Visit website Website: https://www.opalcollection.com/lido-beach/restaurants/drift/
Drift Kitchen & Bar - Lido Beach Resort (8th floor) website1435 Main St, Sarasota, FL 34236
Upscale seafood dining. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: Seafood & coastal American Vibe: Upscale Price: $$$ Good for: Date night, celebrations, special occasions Book: OpenTable reservations
Duval’s Fresh. Local. Seafood. website1377 Main St, Sarasota, FL 34236
Smoothies, bowls & fresh eats. Diverse menu for breakfast through dinner in an artsy, casual ambiance. Food style: American & global fare Vibe: Casual, welcoming Price: $$-$$$ Good for: Breakfast, Lunch, Dinner, Vegan, Healthy dining Book: Visit website Website: https://greenzebrasrq.com
Green Zebra (Downtown) website476 John Ringling Blvd, Sarasota, FL 34236, USA
Cozy health-conscious spot offering breakfast & vegan fare, plus organic smoothies & coffee. Food style: American & global fare Vibe: Casual, welcoming Price: $$-$$$ Good for: Breakfast, Lunch, Vegan, Healthy dining Book: Visit website Website: https://greenzebrasrq.com
Green Zebra (St Armands) website35 S Lemon Ave, Sarasota, FL 34236
Hyde Park Steakhouse delivers your traditional, upscale steakhouse experience, with prime cuts, classic sides, and polished service in a refined setting. The atmosphere strikes a balance between elegant and energetic, especially on weekends. Its lively, upscale happy hour scene makes it a central gathering spot in the heart of downtown Sarasota. Food style: Steaks & classic American Vibe: Upscale Price: $$$ Good for: Date night, celebrations, special occasions, dinner, steak, cocktails Book: OpenTable reservations
Hyde Park Prime Steakhouse website239 S Links Ave, Sarasota, FL 34236
Award-winning seasonal American cuisine. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: American & global fare Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, visitors, and locals Book: OpenTable reservations
Indigenous website1289 N Palm Ave, Sarasota, FL 34236, USA
A trendy, upscale Japanese-fusion spot where creative shareable plates meet a lively, modern crowd. The menu blends sushi, Asian-fusion small plates (like crispy nori tacos, bao buns, and wagyu steaks) with inventive cocktails and a chic bar scene. Perfect for a night out if you want fun vibes, good food, and a touch of sophistication. Food style: Japanese, tapas Vibe: Lively Price: $$$ Good for: Date night, celebrations, special occasions, drinks, dinner, happy hour Book: Visit website Website: http://eatkojo.com/
KOJO website1576 Main St, Sarasota, FL 34236
Lila brings a fresh, vegetable-forward, mostly vegan dining experience to downtown Sarasota, with creative, health-conscious dishes built around seasonal, organic ingredients. Food style: Vegan & vegetarian cuisine Vibe: Casual, Granola-y Price: $$-$$$ Good for: Dinner with friends, lunch, dinner, that relative who is Vegan or Gluten-Free Book: Visit website Website: https://lilasrq.com
Lila website1970 Main St, Sarasota, FL 34236
Classic upscale Italian. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: American & global fare Vibe: Upscale Price: $$$ Good for: Date night, celebrations, special occasions Book: Visit website Website: https://mediterraneosrq.com
Mediterraneo website516 Burns Ct, Sarasota, FL 34236
Low-country seafood + backyard vibe. The Fish Camp in historic Burns Court delivers laid-back Old-Florida charm with great local seafood and Southern comfort favorites. Anchored by its iconic banyan, it blends coastal flavors, history, and a lively front-porch fish-camp vibe. Great pies and "boozy" milkshakes to end your night. No reservations - busy on the weekends so plan for a drink and live music in their backyard while you wait. Food style: Seafood & Southern comfort. Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner, Seafood, family, live music, dessert Website: https://owensfishcamp.com
Owens Fish Camp website1255 N Palm Ave 8th floor, Sarasota, FL 34236, USA
A chic rooftop experience atop the Art Ovation Hotel, perfect for cocktails with sweeping views of Sarasota's skyline at sunset. The menu leans into shareable bites, sushi rolls, and Asian-inspired small plates to complement the drinks, but most guests come primarily for the drinks and the view. It's a great spot for a relaxed evening out or a stylish nightcap under the stars. Food style: Asian-inspired small plates Vibe: Casual, Lively Pool Bar Price: $$-$$$ Good for: Happy hour, rooftop, drinks, night cap Book: Visit website Website: https://classicosrq.com
Perspective Rooftop Bar (8th Floor - Art Ovation) website233 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Ringside at Cirque St. Armands lets you step into a whimsical, circus-inspired world filled with photo-worthy cocktails, playful décor, and theatrical touches that celebrate Sarasota's heritage as the Circus Capital of the World. The menu features modern American coastal cuisine with a creative twist, offering elevated bites and fresh seafood in a lively, immersive setting. Located directly across from Lido Beach, guests enjoy a vibrant atmosphere with peek-a-boo views of the Gulf from select seats. Food style: Seafood & coastal American Vibe: Casual, welcoming Price: $$-$$$ Good for: Breakfast, brunch, lunch, dinner, drinks Book: Google Profile Website: https://www.opalcollection.com/cirque-st-armands/restaurants/ringside/
Ringside at Cirque St. Armands website1216 1st St, Sarasota, FL 34236
Global fine dining + rooftop. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: American & global fare Vibe: Upscale Price: $$$ Good for: Date night, celebrations, special occasions Book: OpenTable reservations
Sage SRQ website1345 Main St, Sarasota, FL 34236
Selva is a landmark in downtown Sarasota dining, known for its vibrant Latin fusion cuisine and artfully plated dishes. The menu highlights Peruvian influences shaped by Asian culinary techniques, creating bold, intricate flavors that feel both exotic and refined. Long praised by visitors and critics alike as "possibly the best food in Sarasota" - this is a spot where everything on the menu truly is worth trying. Food style: Latin-Peruvian fusion Vibe: Lively, sophisticated Price: $$-$$$ Good for: Dinner with friends, date night, drinks Book: OpenTable reservations
Selva Grill website800 Broadway St, Longboat Key, FL 34228, USA
Shore Longboat Key delivers creative, seafood-forward dishes in a breezy, open-air waterfront setting with turquoise water views, craft cocktails, and unbeatable Florida ambiance. It's simply the best waterfront happy hour on our coast. Watch your speed driving Longboat Key! Food style: Modern coastal American Vibe: Casual, Yacht-rock Price: $$-$$$ Good for: Happy hour, drinks, waterfront, dinner, lunch, brunch Website: https://www.dineshore.com/location/shore-longboat-key/
Shore Longboat Key website5238 Ocean Blvd, Sarasota, FL 34242, USA
Great place for happy hour and music...
Siesta Key Oyster Bar website27.260591, -82.524063
Estimated 2025 for retail and apartments, then hotel after.The project will comprise a total of 10 retail and restaurant buildings, including a yet-to-be-named grocer. It will have 140,000 square feet of retail space, with a minimum of 7,000 square feet of office space, and an apartment building with 414 units, 25 of which will be affordable. Siesta Promenade will also include an 80-foot high, 130-room hotel, which will be larger than any single hotel on nearby Siesta Key, where space for such a dense hotel is limited. https://www.sarasotamagazine.com/home-and-real-estate/2023/09/benderson-siesta-promenade-south-sarasota-development
411 N Orange Ave, Sarasota, FL 34236
Creative Asian-fusion cuisine. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: American & global fare Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, visitors, and locals Book: Visit website Website: https://spicestationsrq.com
Spice Station website1533 State St, Sarasota, FL 34236
State Street Eating House and Cocktails serves elevated American fare in a cozy, inviting setting-all about fresh ingredients and bold flavors from brunch classics to hearty dinners. Right next door, there's a speakeasy offering proper cocktails in an intimate environment. It's a great spot for good food and refined drinks when you want something a little more special. Park right across the street at State Street parking garage. Food style: American modern, fresh ingredients Vibe: Lively Price: $$-$$$ Good for: Drinks, brunch, date night, late-night meetups Book: Visit website Website: https://statestreetsrq.com
State Street Eating House + Cocktails website411 N Orange Ave, Sarasota, FL 34236
Elevated New American cuisine. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: American & global fare Vibe: Upscale Price: $$-$$$ Good for: Dinner with friends, visitors, and locals Book: Visit website Website: https://therosemarysarasota.com
The Rosemary website100 Central Ave, Sarasota, FL 34236
Sushi & modern Japanese. It's a favorite stop for visitors and locals looking to enjoy Sarasota's dining and nightlife scene. Food style: Sushi & Japanese cuisine Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, visitors, and locals Book: OpenTable reservations
Tsunami Sushi website373 St Armands Cir, Sarasota, FL 34236
Venezia on St. Armands offers light, approachable Italian-think pizzas, pastas, salads, and gelato-served in a casual, family-friendly setting. The modern, upbeat vibe and energetic patio make it one of the best people-watching spots on one of Sarasota's busiest sidewalks. It's an easy choice for a relaxed lunch or a lively dinner in the heart of the Circle. Food style: Light Italian Comfort Vibe: Casual, welcoming Price: $$-$$$ Good for: Dinner with friends, visitors, happy hour, drink, pizza, family Book: Visit website Website: https://venezia1966.com
Venezia Italian Restaurant website1830 S Osprey Ave, Sarasota, FL 34239, USA
Coastal-chic restaurant with rooftop seating and Gulf views, popular with both locals and visitors for elevated seafood and cocktails. Food style: Coastal American, seafood, craft cocktails Vibe: Upscale casual, lively, sunset-friendly Price: $$-$$$ Good for: Date night, small groups, special occasions Book: OpenTable reservations Google: Reviews, hours & directions
Veronica Fish and Oyster website153 Avenida Messina, Siesta Key Village
Village institution for small plates and big cocktails under string lights — the patio where half the island ends up on a Friday. Live music most nights.
Ryan's take: This is the 9pm answer to "is the Village actually fun?" for buyers test-driving island life.
The Cottage website210 Avenida Madera, Siesta Key Village
The island’s beloved breakfast — courtyard tables, benedicts worth the wait, and staff who remember regulars by name. Locals’ morning ritual, in the best way.
Ryan's take: Weekday 8am feels like a members’ club for residents — the true retiree lifestyle preview.
Sun Garden Cafe website1200 Old Stickney Point Rd, Siesta Key
South-Key landmark since 1979 with an award-winning clam chowder, a backyard tiki bar, and zero pretense. Where boat people and beach people agree on dinner.
Ryan's take: The Sniki Tiki out back is the south island’s living room — five minutes from every mid-Key condo.
Captain Curt's Crab & Oyster Bar website9105 Midnight Pass Rd, Siesta Key
White-tablecloth dining on Little Sarasota Bay at the quiet south end — dock lights, mangrove views, and the Key’s most romantic table. Arrive by boat if you can.
Ryan's take: The proof that the south Key isn’t "far from everything" — it’s near the good thing.
Ophelia's on the Bay website5208 Ocean Blvd, Siesta Key Village
The waffle-cone line that never dies — Amish-recipe ice cream scooped in the Village since 1982. A rite of passage after every beach sunset.
Ryan's take: Grandkid currency. Buyers with visiting family will use this weekly.
6519 Midnight Pass Rd, Siesta Key, FL 34242
Siesta Key's original beach bar — first pour 1949. A beloved old-Florida dive steps from Crescent Beach and Point of Rocks: cold drinks, live music, friendly regulars, and a package store attached for beach provisions. Zero pretense, maximum character. Food style: Bar only — drinks & occasional food trucks Vibe: Old-Florida dive, live music Price: $-$$ Good for: Late-night drinks, live music, meeting locals Book: Walk in Website: https://www.crescentclubsiestakey.com
Ryan's take: Open until 2am every night — one of the only true late-night spots on the Key. Go on a live-music night and arrive before the after-beach crowd rolls in.
Crescent Club website1000 Circus Blvd, Sarasota
Sarasota's 1926 Donald Ross municipal, reborn: architect Richard Mandell's restoration reopened in December 2023 and Golf Digest promptly ranked it the #2 Best New or Remodeled Affordable Course in America (2024). 18 restored Ross holes plus The Gillespie 9-hole short course, wrapped in a 300-acre nature park.
Ryan's take: Walk it like it's 1926 — firm, fast, and the best golf value between Tampa and Naples. Book well ahead in season.
Bobby Jones Golf Club website3101 Longmeadow, Sarasota
Big 2026 news: the former private Meadows Country Club is now a 36-hole PUBLIC destination under Arnold Palmer Golf Management (opened to public play June 2026). The Meadows course (Ron Garl redesign) and the Arthur Hills-designed Groves course, 15 minutes from downtown.
Ryan's take: Newly public means tee times are still easy to get. That window will close.
The Meadows Golf Club website7671 The Park Blvd, University Park
27 Ron Garl-designed holes consistently rated among the best public-accessible golf in Southwest Florida — nearly five stars on GolfPass and a four-star Golf Digest 'Places to Play' fixture since 1996. Semi-private: open to daily-fee play with a 3-day public booking window.
Ryan's take: Any two of the three nines make a par-72. Course conditions here embarrass most private clubs.
University Park Country Club website8255 Legacy Blvd, Bradenton
An Arnold Palmer Signature design and one of the area's most-reviewed public courses — 4.2/5 on GolfPass across 1,100+ golfer reviews. Generous fairways, Palmer-signature risk-reward par 5s.
Ryan's take: Play early — afternoon wind makes the water carries honest.
Legacy Golf Club at Lakewood Ranch website4350 El Conquistador Pkwy, Bradenton
The 1972 El Conquistador course, now home base for IMG Academy's junior golf program. Semi-private and open to public play — par 72, 73.9 rating / 135 slope from the tips, rolling terrain over Sarasota Bay bluffs you won't find elsewhere in flat Florida.
Ryan's take: The back-nine bay views are the area's best-kept golf secret.
IMG Academy Golf Club website301 Gulf of Mexico Dr, Longboat Key
The Gulf-side course at the island's legendary club — redesigned by Ron Garl in 2014, 6,748 yards threading lagoons and sea breeze with the Gulf over your shoulder. Private club, but playable: resort guests at The Resort at Longboat Key Club can book tee times (24 hours ahead). A Golf Digest 'Best Places to Play' honoree.
Ryan's take: Stay one night at the Resort, play the next morning — the legal cheat code into one of Florida's great private clubs. Members get 45 holes; ask Ryan what membership looks like with a Longboat address.
Longboat Key Club — Links on Longboat website2100 Harbourside Dr, Longboat Key
27 tree-lined holes on the bay side of Longboat Key Club — the Red Hawk, White Egret and Blue Heron nines mix and match into three distinct 18s, winding through Sarasota Bay mangroves and the Moorings marina. Private; resort guests can play.
Ryan's take: Blue Heron at dusk, bay on three sides — this is the view that sells Harbourside condos.
Longboat Key Club — Harbourside website7011 Willow St, Sarasota
Donald Ross, 1926 — the same golden-age pedigree as Bobby Jones, kept private. Bobby Jones himself and the era's stars played exhibitions here. Classic small greens, old oaks, timeless routing minutes north of downtown.
5601 Country Club Way, Sarasota
36 holes across the Champions and Lakes courses at one of the area's established member clubs, ten minutes from downtown near UTC. A perennial choice for buyers who want two courses and a full club calendar without island pricing.
4409 TPC Dr, Sarasota
The TPC network's Sarasota outpost in gated Palmer Ranch — 36 holes including the Stadium Course that hosted the Senior PGA Tour's Chrysler Cup. Private and prestigious, with membership tied closely to the surrounding Prestancia community.
Ryan's take: Homes inside Prestancia's gates come with a direct line to membership — ask Ryan for what's available.
TPC Prestancia website2700 Gary Player Blvd, Sarasota
36 championship holes behind the gates of one of Sarasota's premier golf communities — the Gary Player-designed East course and Ron Garl's West course, on 813 oak-canopied acres.
3001 Founders Club Dr, Sarasota
Robert Trent Jones Jr. carved this one through 700 acres of old-Florida oak hammocks east of downtown — routinely named among Florida's best residential courses. Intimate membership, tournament-grade conditioning.
6773 Serenoa Dr, Sarasota
A friendly public 18 south of Clark Road: tight, tree-lined fairways, plenty of water, and more sandhill cranes than golf carts. Honest golf at an honest price.
5100 87th St E, Bradenton
A semi-private Ted McAnlis 18 in a gated community on the Sarasota–Manatee line. Limited outside play keeps the course uncrowded; the club vibe is relaxed rather than stuffy.
4950 Peridia Blvd E, Bradenton
A semi-private executive 18 — par 3s and short 4s you can walk in under three hours. The right speed for family golf, beginners, or a quick morning round before the beach.
6415 53rd Ave W, Bradenton
The area's beloved county muni — a well-kept, walkable public 18 fifteen minutes north of Longboat's north bridge. Where the locals actually play.
101 S Gulfstream Ave, Sarasota, FL 34236, USA
Built: 1974 Avg Size: 1345 Avg Fees: $861 Recent Sales: 5 Max Price: $900,000 Avg Price: $763,960 Avg PP Sq Ft: $583 as of 12/18/22
1100 Boulevard of the Arts, Sarasota, FL 34236, USA
1350 Main St, Sarasota, FL 34236, USA
Built: 2007 Avg Size: 1569 Avg Fees: $1,147 Recent Sales: 20 Max Price: $7,500,000 Avg Price: $1,466,050 Avg PP Sq Ft: $747 as of 12/18/22
332 Cocoanut Ave, Sarasota, FL 34236, USA
Built: 2021 Avg Size: 1059 Avg Fees: $307 Recent Sales: 8 Max Price: $808,885 Avg Price: $755,836 Avg PP Sq Ft: $697 as of 12/18/22
1343 4th St, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 1835 Avg Fees: $0 Recent Sales: 5 Max Price: $1,750,000 Avg Price: $1,390,000 Avg PP Sq Ft: $0 as of 12/18/22
624 S Palm Ave, Sarasota, FL 34232, USA
Built: 2018 Avg Size: 3620 Avg Fees: $2,199 Recent Sales: 2 Max Price: $3,825,000 Avg Price: $3,462,500 Avg PP Sq Ft: $963 as of 12/18/22
711 S Palm Ave, Sarasota, FL 34236, USA
Only 16 residences - Built 2019. $2MM range. Enjoy resort style amenities, including on-site part-time concierge, fitness room, 50' x 20' heated pool and spa, firepit, beautiful Cabanas, 2 gas grills, outside bathroom, 2 showers, air-conditioned storage, guest parking, and pet friendly Paw Park. Each residence has its own airconditioned storage space and 2 secured garage parking spaces with bike rack.
800 N Tamiami Trail, Sarasota, FL 34236, USA
Built: 2005 Avg Size: 1621 Avg Fees: $1,034 Recent Sales: 13 Max Price: $1,500,000 Avg Price: $878,569 Avg PP Sq Ft: $544 as of 12/18/22 First-class amenities include a secured entrance with 24-hour concierge, wine cellar, large pool area with cabanas, spa, theater room, business center, library, game room and clubroom with catering kitchen, storage room, fitness center, sauna, guest suite for your visitors, bicycle storage and fenced pet area. Current and future residents appreciate the unique increasing value with the exciting Rosemary District expansion to the east, and the Sarasota Bay.
280 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2016 Avg Size: 4101 Avg Fees: $4,744 Recent Sales: 1 Max Price: $6,495,000 Avg Price: $6,495,000 Avg PP Sq Ft: $1,584 as of 12/18/22
1255 N Gulfstream Ave, Sarasota, FL 34236, USA
Built: 1982 Avg Size: 1820 Avg Fees: $1,438 Recent Sales: 20 Max Price: $2,300,000 Avg Price: $1,343,150 Avg PP Sq Ft: $737 as of 12/18/221 year minimum Lease Period, no wait to lease. Small pets OK, no LLCs to purchase.13 condo floors with 100 residences (from engineering report) built 1982. Older crowd. Amenities include a beautiful lobby, valet parking, full-service concierge, 24 hr valet, fitness center, media room, heated swimming pool and electric car charging stations. A deeded one-car under-cover garage space conveys with the unit. Can have 2 spots depending on unit. Note: - LOWER units can have waterview blocked by trees - 2022/2023 - Special Assessment has been approved for Windows $62,000 being paid in Quarterly Installments.
301 Quay Commons, Sarasota, FL 34236, USA
Built: 2021 (Completed 2023?) Avg Size: 1958 Avg Fees: $979 Recent Sales: 13 Max Price: $2,999,000 Avg Price: $1,453,615 Avg PP Sq Ft: $0 as of 12/18/22 Amenities include a state-of-the-art fitness center and a movement studio for personal or group classes. The fifth level showcases an elevated resort-style pool and spa, entertainment areas, an outdoor kitchen, a dog park and much more. Bayso residents will also have an on-site property manager, 24-hour front desk attendants and access-controlled entry, making this a true lock-and-leave
990 Boulevard of the Arts, Sarasota, FL 34236, USA
Built: 2003 Avg Size: 2980 Avg Fees: $2,073 Recent Sales: 5 Max Price: $3,500,000 Avg Price: $2,645,000 Avg PP Sq Ft: $887 as of 12/18/22 44 residences - 24-hour concierge service, a fitness center, steam shower and sauna, a massage room, a heated pool and spa, and an outdoor kitchen.
540 N Tamiami Trail, Sarasota, FL 34236, USA
Built: 2020 Avg Size: 3704 Avg Fees: $1,910 Recent Sales: 5 Max Price: $3,999,000 Avg Price: $3,229,800 Avg PP Sq Ft: $829 as of 12/18/22
1469 5th St, Sarasota, FL 34236, USA
Built: 2023 Avg Size: 1967 Avg Fees: $0 Recent Sales: 5 Max Price: $2,095,000 Avg Price: $1,428,000 Avg PP Sq Ft: $0 as of 12/18/22 Ready Summer 2023
888 Boulevard of the Arts, Sarasota, FL 34236, USA
Built: 1982 Avg Size: 1847 Avg Fees: $869 - $1200 Recent Sales: 13 Max Price: $2,08,000 Avg Price: $1,652,769 Avg PP Sq Ft: $855 as of 12/18/22 The Southern Most Tower, 4 month lease minimums, NO Pets allowed. Garage parking, gated grounds with security 9 acre gated peninsula, docks available first come first serve.Tower II has stricter lease minimums (1 year)
770 S Palm Ave, Sarasota, FL 34236, USA
Built: 1975 Avg Size: 1455 Avg Fees: $1,060 Recent Sales: 9 Max Price: $2,175,000 Avg Price: $1,171,444 Avg PP Sq Ft: $898 as of 12/18/22 17-18 stories, Washer/Dryer in units? Only cats allowed, 3 mo lease minimum and no wait to lease.
605 S Gulfstream Ave, Sarasota, FL 34236, USA
Built: 2019 Avg Size: 4736 Avg Fees: $4,849 Recent Sales: 3 Max Price: $9,700,000 Avg Price: $6,673,667 Avg PP Sq Ft: $1,374 as of 12/18/22
707 S Gulfstream Ave, Sarasota, FL 34236, USA
Built: 1974 Avg Size: 1398 Avg Fees: $981 Recent Sales: 6 Max Price: $1,000,000 Avg Price: $803,167 Avg PP Sq Ft: $532 as of 12/18/22 12 mo lease minimum, no wait to lease. Pets allowed
509 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2024 Avg Size: 2564 Avg Fees: $2,496 Recent Sales: 5 Max Price: $3,200,000 Avg Price: $2,902,240 Avg PP Sq Ft: $0 as of 12/18/22
33 S Gulfstream Ave, Sarasota, FL 34236, USA
Built 1964, Pool over parking garage
505 S Orange Ave, Sarasota, FL 34236, USA
Built: 2007 Avg Size: 2868 Avg Fees: $1,593 Recent Sales: 3 Max Price: $2,075,000 Avg Price: $1,899,500 Avg PP Sq Ft: $664 as of 12/18/22
1750 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Built 1970, simple pool, covered parking
1800 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Built 1996, nice pool and spa on the beach. Did OK in the hurricanes. 1 spot garage parking
464 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2006 Avg Size: 3312 Avg Fees: $3,018 Recent Sales: 2 Max Price: $4,298,000 Avg Price: $3,846,500 Avg PP Sq Ft: $0 as of 12/18/2228 Residences La Bellasara is a gated, pet-friendly community with excellent amenities including concierge services, a full fitness center, armchair theatre and entertainment room, a bay-front heated pool & spa plus a community day dock.
1212 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Built 1974, 12 floors, basic pool. Covered parking
2100 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Built 1965, took on water from 2024 Hurricanes. Already dangerously close to the gulf with a retaining wall.
1770 Benjamin Franklin Dr, Sarasota, FL 34236, USA
Built 1970s, simple pool and smaller building right on the beach. Covered parking available
1233 N Gulfstream Ave, Sarasota, FL 34236, USA
Built: 2001 Avg Size: 2313 Avg Fees: $1,574 Recent Sales: 5 Max Price: $2,800,000 Avg Price: $2,083,000 Avg PP Sq Ft: $885 as of 12/18/22 There's a highly skilled executive manager and 24-hour front desk personnel. They can monitor your condo while you're out of town and will assist with unloading residents' cars from the private, monitored garage. Two deeded parking spaces are included. Owners' guests may stay in a private suite. The main floor also includes a newly luxury-designed entertainment space perfect for card games, meeting space, super bowl parties or more. At lobby level there's a covered pool, spa & fitness room
111 S Pineapple Ave, Sarasota, FL 34236, USA
Built: 2019 Avg Size: 1687 Avg Fees: $993 Recent Sales: 16 Max Price: $2,995,000 Avg Price: $1,594,288 Avg PP Sq Ft: $881 as of 12/18/22 Building amenities include an expansive fitness center, spin room, saltwater lap pool, hot tub, poolside cabana, fire pit lounge, outdoor grills, a club room with billiards, catering kitchen and bar, a media room, 24-hour concierge, assigned garage parking, and storage locker. The building is pet-friendly and allows owners to have two large pets
1100 Boulevard of the Arts, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 3567 Avg Fees: $2,387 Recent Sales: 38 Max Price: $13,694,000 Avg Price: $3,912,616 Avg PP Sq Ft: $0 as of 12/18/22The 18-story One Park is bringing a quintessential lifestyle to one of Downtown Sarasota's most sought after locations, Boulevard of the Arts. Featuring panoramic direct views from Bay Park to Downtown Sarasota. World-class amenities and services include resort-style infinity-edge pool and spa deck with lounge area, wellness spa, fully staffed One Park Executive Office Suites designed to serve as a flexible office space for residents, private theater room, and a state-of-the-art fitness studio featuring the latest high-tech exercise equipment, Pilates, yoga and cycling rooms
609 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2019 Avg Size: 2750 Avg Fees: $1,082 Recent Sales: 1 Max Price: $3,400,000 Avg Price: $3,400,000 Avg PP Sq Ft: $1,236 as of 12/18/22
223 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 2650 Avg Fees: $1,940 Recent Sales: 8 Max Price: $6,186,800 Avg Price: $3,103,100 Avg PP Sq Ft: $0 as of 12/18/22 Ready 2024
50 Central Ave, Sarasota, FL 34236, USA
Built: 2005 Avg Size: 2404 Avg Fees: $2,274 Recent Sales: 3 Max Price: $4,475,000 Avg Price: $2,356,333 Avg PP Sq Ft: $650 as of 12/18/22 An intimate pet-friendly boutique building with only 49 residence provides valet parking, resort-style heated pool & spa, grilling area, screened in gazebo with a fireplace, plus a club room with a catering kitchen, conference room, guest suite, fully equipped fitness center.
435 S Gulfstream Ave, Sarasota, FL 34236, USA
Built: 1972 Avg Size: 1602 Avg Fees: $1,049 Recent Sales: 4 Max Price: $937,500 Avg Price: $795,875 Avg PP Sq Ft: $473 as of 12/18/22 Built 1972 - Covered Parked, Building Concierge, Pool (bayside)
750 N Tamiami Trail, Sarasota, FL 34236, USA
Built: 2001 Avg Size: 1411 Avg Fees: $954 Recent Sales: 5 Max Price: $1,200,000 Avg Price: $866,600 Avg PP Sq Ft: $619 as of 12/18/22 There is concierge service, club room with a lovely fireplace, a business center, conference room, resident theater, catering kitchen, fitness center, massage rooms, saunas, heated pool and spa. There are 2 guest suites for the use of residents for the overflow of their guests
555 S Gulfstream Ave, Sarasota, FL 34236, USA
Built 1969 - Very basic pool and tiny fitness center Dated Vibe Overall
1188 N Tamiami Trail, Sarasota, FL 34236, USA
Built: 2006 Avg Size: 2411 Avg Fees: $1,183 Recent Sales: 1 Max Price: $1,050,000 Avg Price: $1,050,000 Avg PP Sq Ft: $436 as of 12/18/22 23 Units, 2 underbuilding parking spaces, 2 storage units, as well as association amenities. Relax and enjoy the outdoor heated pool, sun terrace, fitness center and sauna. A secured entrance and pet friendly building
300 S Pineapple Ave, Sarasota, FL 34236, USA
Built: 2016 Avg Size: 2363 Avg Fees: $1,681 Recent Sales: 4 Max Price: $2,350,000 Avg Price: $2,181,250 Avg PP Sq Ft: $936 as of 12/18/22
340 S Palm Ave, Sarasota, FL 34236, USA
Built: 1998 Avg Size: 3647 Avg Fees: $2,968 Recent Sales: 2 Max Price: $4,000,000 Avg Price: $3,275,000 Avg PP Sq Ft: $882 as of 12/18/22 Dated amenities, nice views
688 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 2790 Avg Fees: $984 Recent Sales: 7 Max Price: $6,888,000 Avg Price: $3,673,714 Avg PP Sq Ft: $0 as of 12/18/22 Ready 2024
500 S Palm Ave, Sarasota, FL 34236, USA
Built: 2000 Avg Size: 3072 Avg Fees: $2,092 Recent Sales: 4 Max Price: $3,425,000 Avg Price: $2,833,750 Avg PP Sq Ft: $887 as of 12/18/22 Built 2000 , priced in $2.5m+ , pool, fitness, private garage
1335 2nd St, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 3060 Avg Fees: $1,615 Recent Sales: 11 Max Price: $4,899,900 Avg Price: $2,909,064 Avg PP Sq Ft: $0 as of 12/18/22 Only 12 residences Sold Out - Ready 2022
33 S Palm Ave, Sarasota, FL 34236, USA
Built: 2020 Avg Size: 1834 Avg Fees: $837 Recent Sales: 31 Max Price: $12,500,000 Avg Price: $1,911,774 ($4m active list price) Avg PP Sq Ft: $0 as of 12/18/22 Summer 2023 39 private residences at The DeMarcay with 24/7 staff and rooftop pool and clubroom
290 Cocoanut Ave, Sarasota, FL 34236, USA
Built: 2022 Avg Size: 3068 Avg Fees: $1,109 Recent Sales: 10 Max Price: $3,742,000 Avg Price: $2,628,921 Avg PP Sq Ft: $0 as of 12/18/22 Ready 2024
1301 Main St, Sarasota, FL 34236, USA
Built: 2016 Avg Size: 4059 Avg Fees: $3,211 Recent Sales: 1 Max Price: $3,800,000 Avg Price: $3,800,000 Avg PP Sq Ft: $936 as of 12/18/22
136 Golden Gate Point, Sarasota, FL 34236, USA
Built: 2001 Avg Size: 3785 Avg Fees: $1,750 Recent Sales: 2 Max Price: $3,600,000 Avg Price: $3,350,000 Avg PP Sq Ft: $819 as of 12/18/2213 residences, featuring private 2-car garages, fitness center, pool and spa
1111 Ritz Carlton Dr, Sarasota, FL 34236, USA
Built: 2001 Avg Size: 3368 Avg Fees: $2,929 Recent Sales: 11 Max Price: $5,950,000 Avg Price: $3,229,000 Avg PP Sq Ft: $829 as of 12/18/22
401 Quay Commons, Sarasota, FL 34236, USA
Built: 2018 Avg Size: 5350 Avg Fees: $4,190 Recent Sales: 3 Max Price: $10,575,000 Avg Price: $8,808,333 Avg PP Sq Ft: $1,642
35 Watergate Dr, Sarasota, FL 34236, USA
Built: 2003 Avg Size: 3518 Avg Fees: $2,983 Recent Sales: 15 Max Price: $5,500,000 Avg Price: $3,256,933 Avg PP Sq Ft: $899 as of 12/18/22
1155 N Gulfstream Ave, Sarasota, FL 34236, USA
Built: 2017 Avg Size: 1933 Avg Fees: $1,361 Recent Sales: 14 Max Price: $3,575,000 Avg Price: $2,286,786 Avg PP Sq Ft: $1,189 as of 12/18/22
Whispering Sands Dr, Siesta Key
Gulf-front village-walkable co-op community from 1973 — towers and garden villas on one of the widest private stretches of quartz sand on the Key. The rare address where you get sunset water and a five-minute stroll to dinner.
Ryan's take: 55+ garden sections and all-ages tower units follow different rules — ask before you fall in love.
W Peppertree Dr, Siesta Key
A 1975 gulf-to-bay classic: beach on one side, fishing pier and kayak water on the other, with mid-rise and villa options between. One of the few communities where "gulf-to-bay" is literal.
Ryan's take: Units facing the gulf courtyard trade differently than bayside — walk both before choosing.
5740 Midnight Pass Rd, Siesta Key
The Key’s amenity heavyweight — 32 gulf-front acres on Crescent Beach with pools, tennis, fitness and lush grounds behind a gate. 1980s-built, resort-run, and perennially in demand.
Ryan's take: Phases differ by view and renovation wave; the beach path from any of them is the great equalizer.
Siesta Bayside Dr, Siesta Key
The quieter 1988 sibling across Midnight Pass Rd — townhomes and flats on the bay side with deeded beach access to Crescent. More space per dollar than the gulf-front big brother.
Ryan's take: Ask about boat dock availability — bayside means real water access, not just a view.
S Portofino Dr, Siesta Key
55+ boating community on the Intracoastal with docks, heated pool and a walk-to-Crescent-Beach location. 1970s bones, unbeatable harbor character, and some of the Key’s most attainable waterfront.
Ryan's take: Dock slips are the hidden value — a deeded or available slip changes the math entirely.
Cove II Pl, Siesta Key
Bayside 1979 community with gulf access via deeded beach path across the road — popular with owners who rent, thanks to flexible minimums and a real rental office on site.
Ryan's take: Strong rental history makes this a favorite first island purchase — run the numbers both ways.
6415 Midnight Pass Rd, Siesta Key
Mid-rise 1975 tower on the Intracoastal with boat docks, tennis and a genuinely social pool deck. South-Key location puts Turtle Beach and Ophelia’s within a bike ride.
Ryan's take: Water-facing stacks watch dolphins from the balcony; ask which slips are transferable.
5855 Midnight Pass Rd, Siesta Key
Twin 1976 towers on the bay with first-come docks, two pools, saunas and deeded Crescent Beach access. Yacht-and-racquet DNA at a mid-island price point.
Ryan's take: Two-week rental minimums draw steady seasonal demand — good for offsetting carry costs.