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$769,000
2 Beds ⋅ 3 Baths ⋅ Fairway Bay 1 SubDv. ⋅ 34228 Zip Code ⋅ TB8422578 MLS ⋅ Active Status
GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.

1926 Harbourside Drive Unit 1302, Longboat Key
$575,000
2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code ⋅ TB8422646 MLS ⋅ Active Status ⋅ 925 BLDG.
Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!

925 Beach Road Unit 310, Siesta Key
$529,500
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code ⋅ A4663602 MLS ⋅ Active Status ⋅ Fairmount BLDG.
Direct Waterfront, newly updated 2 bedroom 2 bath end unit with hurricane resistant windows and sliders. Sarasota Harbor East, a premier 55+ maintenance-free community in one of the most desirable bayfront locations in Sarasota! Just minutes from downtown Sarasota, St. Armands Circle, Lido Beach, and directly across from the Sarasota Yacht Club, this community offers an unmatched combination of convenience, charm, and waterfront living. This residence features a fully glass-enclosed lanai—perfect for soaking in the spectacular waterfront views. The unit also comes with a covered parking space plus ample guest parking. Community highlights include: Free boat docks for sailboats or powerboats up to 30’ (first-come, first-serve), heated waterfront pool with stunning bay views, community gas grill and picnic area, secured covered bicycle shed & kayak storage, individual storage bins for residents. With its unbeatable location, Sarasota Harbor East is a rare opportunity to own in one of Sarasota’s most sought-after waterfront communities.

771 John Ringling Boulevard Unit 7, Lido Key
$4,250,000
5 Beds ⋅ 5 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code ⋅ A4663247 MLS ⋅ Active Status
Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef’s kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota’s sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key’s world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?

160 Garden Lane, Siesta Key
$1,100,000
Siesta Rev SubDv. ⋅ 34242 Zip Code ⋅ A4663281 MLS ⋅ Active Status
Excellent Development and Investment Opportunity LOT, PLANS and PERMITS have already been city-approved to build a new home on the property located on the coveted north end of Siesta Key just minutes from Siesta Key Beach! Renderings can be found under attachments. Refurbish and renovate the existing property, or tear it down and build your dream home on this prime oversized corner lot.. The preliminary plans are attached for a coastal contemporary elevated three-story home featuring 5 bedrooms, 4 full and 1 half bathrooms, a two car garage, open floor plan, gourmet chef’s kitchen, dining room, a dedicated office, flexible bonus spaces, an elevator servicing all three levels. The outdoor area includes multiple covered lanais and balconies, spaces for entertaining, and a resort-style pool and spa with a sun shelf. Short-term rentals are permitted, allowing flexibility for many investment opportunities such as Airbnb and vacation rentals. Located just steps from Siesta Key’s world-famous beaches and only minutes from Siesta Village dining and shopping, this new construction residence offers the perfect blend of luxury, design, and island lifestyle. This is a rare opportunity to enjoy island life and the best beaches while living in a convenient location within very close proximity to Downtown Sarasota, Southside Village, top restaurants, shopping, hospitals, and entertainment.

160 Garden Lane, Siesta Key
$349,000
1 Beds ⋅ 1 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code ⋅ A4662852 MLS ⋅ Active Status ⋅ 904 BLDG.
PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene setting. This turnkey furnished unit is move-in ready and features a bright, open floor plan with tasteful coastal updates throughout. The enclosed lanai adds valuable additional living space, ideal for relaxing or entertaining. The A/C system is serviced annually and is in excellent working condition, offering added peace of mind. White Sands Village is a hidden gem, known for its affordability, strong amenities, and rental flexibility. Residents enjoy a heated community pool, a newly renovated clubhouse with kitchen and gathering spaces, beautifully maintained grounds with paver roadways, and covered carports. Community boat docks are available on a first-come basis for a nominal fee. Small pets are welcome for both owners and tenants—an increasingly rare benefit on Siesta Key. With a two-week minimum rental policy and an on-site rental agent, this community supports steady income potential, making it equally attractive as a personal retreat or investment property. The nearby free Siesta Key trolley provides easy access to Siesta Key Village, dining, shopping, and downtown Sarasota’s cultural and dining scene. This price improvement enhances an already compelling opportunity to own in one of Siesta Key’s most desirable communities—where comfort, location, and income potential come together seamlessly.

5641 Midnight Pass Road Unit 904, Siesta Key
$495,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code ⋅ A4656278 MLS ⋅ Active Status ⋅ Section 5 BLDG.
One or more photo(s) has been virtually staged. BEST PRICED UPDATED VILLA WITH GARAGE ON SIESTA KEY! Don't miss this opportunity to own this lovely REMODELED VILLA just steps from the sand! This 2 bed/2 bath villa nestled in the premier GULF FRONT property of Whispering Sands is the perfect island getaway. Remodeled in 2025, this villa features all NEW vinyl plank flooring, paint, baseboards, trim, molding, and all interior doors. The bright NEW galley kitchen is a true highlight, offering stylish soft close cabinetry, granite countertops, stainless Whirlpool appliances, a side by side fridge with icemaker/dispenser, stainless farmhouse sink, and recessed and under-cabinet lighting. Both bathrooms have been refreshed with new granite counters, cabinets, vanities, and fixtures for a clean, contemporary feel. You’ll enjoy the ease of indoor-outdoor living with a tiled screened lanai – perfect for your morning coffee or evening relaxation. It could be further enclosed with windows or sliders and turned into a sunroom. This villa also features a nice skip trowel ceiling finish and plantation shutters. One car garage with NEW 2026 epoxy floor. NEW 2025 full sized Maytag WASHER & DRYER. NEW 2025 VILLA ROOF. 2025 HVAC system and 2025 water heater. Ideally located just around the corner from Whispering Sands’ two sparkling heated pools, clubhouse (currently in the beginning stages of being remodeled and which will include a fitness center and catering kitchen), NEW beachside Tiki Hut, shuffleboard, and 800' of your own private beach on the Gulf — perfect for enjoying Siesta Key’s world famous quartz sand and spectacular sunsets! When you're not luxuriating in the pool or going for a dip in the Gulf, step out of your front door and walk to shopping and dinner! Whispering Sands is situated right around the corner from the colorful boutiques and fine restaurants of Siesta Key Village. Embrace the island lifestyle! Whether as a year-round residence or a vacation retreat, this maintenance free Gulfside villa combines ease, style, comfort - and a great investment - in one of Siesta Key’s finest Gulf front properties.

119 Whispering Sands Circle Unit V36, Siesta Key
$399,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code ⋅ A4662792 MLS ⋅ Active Status ⋅ 6157 BLDG.
BAY OAKS on WORLD FAMOUS SIESTA KEY! This 3rd floor unit is Perfectly positioned with pool view and great rental location! Watch your family swim in the pool directly from your balcony! Priced for immediate sale and ready to rent!! Now is the time to make this 2-bedroom, 2-bath condo your island paradise. With WEEKLY RENTALS allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and BRAND NEW CARPETS IN BEDROOMS making it rental ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley.

6157 Midnight Pass Road Unit E63, Siesta Key
$995,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code ⋅ A4661696 MLS ⋅ Active Status ⋅ Building 5 BLDG.
Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! An iconic condominium in the mid-century modern style, Beachplace was constructed under the direction of Tim Siebert, one of the leaders of the Sarasota School of Architecture, and spans 31 acres with a quarter mile of Gulf beachfront. This price reduction makes this an ideal residence or investment opportunity. With a direct Gulf view, and a gentle walk to the beach, this two-bedroom, two-bathroom residence offers serene living; a spacious primary suite with ensuite bath, plus a guest suite, private balcony with stunning sunset views, full kitchen and dining and living spaces, new impact glass windows, all complemented by nearby amenities, including private beach access, a Junior Olympic-sized pool, spa, and a kid's pool. A clubhouse, two fitness facilities, a sauna, tennis, and pickleball courts, and two grilling stations complete the resort lifestyle. Electric Vehicle charging is on-site. The Resort at Longboat Key Club is immediately adjacent and offers championship golf and tennis facilities, a full-service marina nearby, and fine dining for its members and guests. St. Armands Circle shopping, dining, and entertainment is a short drive south, and Sarasota, with its thriving arts and cultural communities, eclectic shopping and dining, and extraordinary architecture, is a brief ride across the bay. Thirty-day minimum rentals are permitted twelve times annually. The buyer or their agent should review the possibility of any special assessments with the condominium manager. All of the information provided is considered reliable, but should also be verified by the buyer or buyer's agent.

1105 Gulf Of Mexico Drive Unit 402, Longboat Key
$1,649,000
5 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code ⋅ A4661717 MLS ⋅ Active Status
Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.

156 Siesta Drive, Siesta Key
$12,950,000
5 Beds ⋅ 7 Baths ⋅ Saint Armands Div John Ringling Estates SubDv. ⋅ 34236 Zip Code ⋅ A4661401 MLS ⋅ Active Status
Like a Picassos’ Mona Lisa, a true masterpiece. THIS home is the GEM of all jewels. It is one of a kind, created with artistry-imagination & craftsmanship that simply cannot be replicated. This is not your typical concrete block home. It has warmth, & timeless character. Every detail reflects the skill of master craftsmen whose work has become increasingly rare. Homes of this quality are no longer built, making this residence as exceptional as it is beautiful. In a world filled with contemporary “concrete boxes” that often lack warmth, personality & charm, this home stands apart. It invites you to slow down, sit back, stay awhile, and savor every moment. It doesn’t just provide shelter—it embraces you with comfort, elegance, & a sense of belonging. Warm, ageless, and unforgettable, this is more than a home. It is a work of art that quietly whispers, “Stay here…create new memories for a lifetime” Timeless Elegance, Effortless Living where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, a neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway & Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical home. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials & artisanship. Expanded from 4,000 to nearly 10,000 sq. ft. under roof & featuring over 7,800 sq. f.t of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis-kayaks, & breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats & entertaining areas, all complemented by stunning garden water vistas, a central courtyard, & an elegant 65' saltwater pool & spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, & custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range & hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, & curated artwork create an inviting, sophisticated atmosphere, offered furnished. Instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance & modern comfort on one of Sarasota’s most coveted waterfront estates. IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.

139 S Washington Drive, Lido Key
$595,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code ⋅ A4661131 MLS ⋅ Active Status ⋅ Na BLDG.
ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen with Granite countertop, Laundry in Residence, office space off foyer. Partially Furnished! Carport! Island Reef is a serene waterfront community, one of the few Gulf to Bay community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed) two lit tennis courts, pickleball, 2 fitness rooms, Kayak Storage, Library, Billiards, game room, clubhouse, two heated pools and Gas Grills, PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key’s popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cute brunch spots and dancing and live music every night of the week!

8779 Midnight Pass Road Unit 401H, Siesta Key
$4,695,000
6 Beds ⋅ 6 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code ⋅ A4661312 MLS ⋅ Active Status
New Construction. Experience the pinnacle of waterfront luxury with this brand-new construction home in the heart of Longboat Key competitively priced and ready for its next owner. Situated on a private canal, this 5-bedroom plus den, 4,106 sqft residence offers the perfect blend of modern elegance and coastal charm. Designed for seamless indoor-outdoor living, the home features two lanais, a private pool with a spa, and an elevated foundation at 9.5 feet. Boating enthusiasts will appreciate the 10,000-lb boat lift and quick access to the Gulf of Mexico for endless days on the water. Inside, enjoy engineered hardwood flooring throughout, quartz countertops in every space, and a large walk-in pantry. The thoughtfully designed layout includes two laundry rooms for added convenience. Nestled in a quiet, private setting, yet just minutes from Longboat Key’s pristine beaches, golf courses, and fine dining, this home is a rare find. Don’t miss the chance to own a waterfront masterpiece in one of Florida’s most desirable locations.

569 Bayview Drive, Longboat Key
$995,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4660982 MLS ⋅ Active Status
This lot is located in The Preserve at Longbeach with plans and design already to go, an exclusive enclave of 12 new homes, light filled and luxurious contemporary homes. Refinement meets relaxation at the north end of LBK in Longbeach Village - where beach-to-bay access with waterfront amenities, al fresco dining, multiple kayak launch points, a neighborhood boat dock and ramp, and a free-spirited lifestyle await. Exhale and enjoy a neighborhood where the waterfront is at your fingertips and peacocks walk the streets. All that makes Coastal Florida living so enchanting is yours to enjoy here - be one of only 12. Located a short distance from the public beach access, the tranquil beaches of Longboat Key are yours to enjoy whether going for a swim in warm, Gulf waters, walking the beach or enjoying the sunset. Whether by boat or car, you're only minutes from world-class dining and shopping, a host of cultural amenities, and nearby barrier islands.

6800 Longboat Drive S, Longboat Key
$455,000
1 Beds ⋅ 1 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code ⋅ A4660419 MLS ⋅ Active Status ⋅ Na BLDG.
Attention Boaters, Kayakers and Tennis players! Located in the heart of Siesta Key overlooking the Sarasota Little Bay, the Harbor Towers Yach and Racquet Club is a resort-style community offering a long list of amenities including two heated pools, club house with adjacent outdoor grilling patio, state-of-the-art Fitness Center with treadmills, elliptical trainers, free weights, and sauna; Har-Tru Tennis Courts, that are maintained daily, Marina with 40 boat slips available on a first-come, first-served basis, Kayak dry dock with direct launch to intercoastal waters, and Bicycle storage. The complex backs to an intercoastal canal where you can enjoy sitting on benches or relaxing in the shade of Gazebo enjoying water views. Residents also enjoy complimentary access to the Siesta Key Open Air Trolley, making it easy to explore the island, with easy access to the world-famous Siesta Key beach with its quartz sand and stunning sunsets, as well as the Siesta Key Village, offering an array of boutique shopping and dining options. The building just underwent full renovation, including new stucco, new impact glass windows and sliding doors. This 1 bedroom, 1 bath unit located on 3rd floor with elevators is being offered turnkey furnished. It was updated a few years ago and the owner recently put up new vinyl flooring and new closet doors. The spacious living area and the glass and screen enclosed balcony offers partial views of the intracoastal waterway, and the apartment features a plenty of closet space (2 hallway closets and 2 closets in the bedroom), plus the lockable storage space outside of the unit on the same floor. You may enjoy this property for personal use and/or take advantage of the 2-week rental policy to generate income. If you decide to rent, you can take do it on your own or utilize HT onsite rental office. Rental history of this unit is available. Come to experience living in paradise! This complex was just featured in local newspaper!

5855 Midnight Pass Road Unit 314, Siesta Key
$600,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code ⋅ A4661181 MLS ⋅ Active Status
104 ft. x 29.5 ft. Boat Slip at Longboat Key Moorings Marina. This is a 104 ft. long T-dock/face dock ready to accommodate a large yacht; ample electrical service outlets. O-13 is 49.5 feet, and O-14 is 54.5 ft, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle o St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. Longest vessel permitted at the dock is 99 feet, usable beam is 25 feet. Vessel must be approved prior to entering the marina. A photo and boat specs must be provided to the Association.

2600 Harbourside Drive Unit O-13/14, Longboat Key
$699,000
2 Beds ⋅ 3 Baths ⋅ Northgate Of Longboat Key SubDv. ⋅ 34228 Zip Code ⋅ A4657668 MLS ⋅ Active Status ⋅ 490 BLDG.
This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

490 N Shore Road Unit 6, Longboat Key
$5,999,000
4 Beds ⋅ 5 Baths ⋅ Aria Longboat Key SubDv. ⋅ 34228 Zip Code ⋅ A4658325 MLS ⋅ Active Status ⋅ Aria BLDG.
Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most exclusive enclaves. Beyond the gated entrance, Aria unveils a serene, resort-inspired setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the community’s elegant social centerpiece. This impeccably designed, residence spans nearly 4,000 square feet and is accessed via a private elevator, opening to a grand foyer and expansive, light-filled interiors. Recent enhancements include freshly painted cabinetry throughout the home. The thoughtfully curated open-concept floor plan seamlessly integrates sophisticated living and dining spaces with a chef’s kitchen, creating an ideal environment for both everyday living and elevated entertaining. Walls of floor-to-ceiling glass and soaring ceilings invite natural light while framing sweeping, unobstructed views of the Gulf. Expansive wraparound terraces provide the perfect setting to enjoy breathtaking sunsets and coastal breezes from nearly every room. The gourmet kitchen is a statement of both form and function, featuring premium quartz surfaces, freshly painted custom wood cabinetry, and top-tier appliances by Wolf and Miele. The primary suite serves as a private sanctuary, offering a spa-inspired retreat with dual baths connected by an oversized walk-in shower an exceptional design element rarely found. Two additional ensuite bedrooms provide luxurious accommodations for guests, while a dedicated office or optional fourth bedroom adds versatility. A bonus room offers additional flexibility for hobbies, media, or storage. Residents of Aria enjoy an unparalleled suite of amenities, including a beachfront pool and spa, state-of-the-art fitness and yoga studios, massage room, and a private wine cellar. A full-time onsite caretaker ensures a seamless, service-oriented lifestyle. The residence also includes a private, oversized two-car dehumidified garage. Don't miss the NEW video tour.

2251 Gulf Of Mexico Drive Unit 301, Longboat Key
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code ⋅ A4656887 MLS ⋅ Active Status ⋅ Sea Gate Club BLDG.
Price Reduced $100k—Welcome to Sea Gate Club #10F, a rare 10th-floor corner unit with sweeping, unobstructed Gulf views on Longboat Key. This 2-bed, 2-bath residence is filled with natural light and offers stunning sunsets from nearly every room—an ideal coastal retreat for relaxing or entertaining. Located in an intimate 89-unit beachfront community, Sea Gate Club offers a quiet, refined lifestyle with extensive recent upgrades, including impact windows, new roof, exterior renovation, pool, elevators, and more—no pending special assessments. Enjoy resort-style amenities: Gulf-front pool and spa, fitness center, tennis court, library, and social spaces, plus beachside extras like tiki huts and storage for bikes and water gear. Just minutes from St. Armands Circle, you’ll have easy access to dining, shopping, and island charm. Private, peaceful, and rarely available—this is Gulf-front living at its best.

2425 Gulf Of Mexico Drive Unit 10F, Longboat Key
$669,900
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code ⋅ A4656918 MLS ⋅ Active Status
Step into your slice of paradise with this amazing lifestyle opportunity in Siesta Key's esteemed Island House Beach Resort. This impeccable 2-bedroom, 2-bath luxurious coastal Villa, which was completely renovated in 2025, seamlessly blends comfort, style, and investment potential, making it the perfect choice for discerning buyers, seasonal residents, and savvy investors alike. From the moment you enter, you'll be welcomed by a bright, open-concept living area with hurricane-impact windows and sliding glass doors that fill the space with natural light and peace of mind. The dedicated dining enclave flows into a chef-inspired kitchen, fully equipped with gleaming, state-of-the-art stainless steel appliances, ideal for preparing both gourmet meals and casual snacks after a day at the beach. Unwind in your private enclosed lanai, where gentle Gulf breezes create a serene backdrop for evening cocktails, before retiring to the villa’s two spacious bedrooms. But the real draw is that, just steps from your door, the Gulf of Mexico’s crystal-clear waters and powdery white sand are mere moments away. Whether you decide to spend the day lounging in private beach cabanas or indulging in the Island House’s other resort-style amenities, like year-round swimming in the nearby heated pool, preparing the day's fresh catch on the outdoor grills, or challenging friends in the game room or on the beachfront shuffleboard courtyard, every day feels like a vacation. Beyond the complex, endless adventure awaits. Tee off at nearby golf courses, comb one of the many nearby beaches for shells and shark teeth, go hiking or birding in one of the areas fabulous preserves and state parks, or get out on the water boating, fishing, kayaking, or flying high on a parasailing excursion; Then take the afternoon to explore vibrant local shops, acclaimed restaurants, and the charming art galleries of Siesta Key Village, Gulf Gate, and downtown Sarasota. Whether you’re seeking a luxurious personal retreat or a high-demand managed vacation rental for your investment portfolio, this villa offers unparalleled value and an enviable coastal lifestyle. Opportunities like this are scarce, so schedule your private tour today and make your dream a reality! A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.

6150 Midnight Pass Road Unit V38, Siesta Key
$550,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code ⋅ A4657767 MLS ⋅ Active Status ⋅ G-3 BLDG.
THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!

2039 Gulf Of Mexico Drive Unit G3-207, Longboat Key
$995,000
2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code ⋅ A4657483 MLS ⋅ Active Status ⋅ Unit 6 BLDG.
Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.

6308 Midnight Pass Road Unit 6, Siesta Key
$1,090,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4657391 MLS ⋅ Active Status
Discover the exceptional potential of 640 Lyons Lane, a perfectly situated vacant lot on a unique street in North Longboat Key, with homes only on one side and protected wetlands on the other. This property offers an outstanding opportunity to build your dream residence in the sought-after Longboat Key with expansive views over the tranquil canal. Adding to its allure, the property includes a newly installed pool and a convenient boat dock with a 10,000 lb lift, which can all be seamlessly integrated into the future home. Whether you're looking to create a permanent residence or a luxurious vacation retreat, 640 Lyons Lane offers the ideal canvas. Don't miss this opportunity to own a piece of paradise in Longboat Key, with proximity to pristine beaches, golf courses, and fine dining.

640 Lyons Lane, Longboat Key
$5,450,000
7 Beds ⋅ 9 Baths ⋅ Mira Mar Beach SubDv. ⋅ 34242 Zip Code ⋅ A4656843 MLS ⋅ Active Status
Luxury Living in the Heart of Siesta Key! This beautifully designed coastal retreat offers 7 bedrooms, 7 full bathrooms, and 2 half baths, providing plenty of space for hosting family and friends in total comfort. Every detail was thoughtfully crafted to blend high-end design with relaxed Florida living. The main living area is open, airy, and filled with natural light, creating an effortless flow for both everyday life and entertaining. A private elevator makes accessing all levels a breeze, while wraparound balconies and large windows showcase the lush, tropical surroundings. At the center of the home, the chef’s kitchen features a gas range, oversized island, and ample seating—perfect for gathering, cooking, and connecting. Step outside and you’ll find your own private escape: a heated pool and spa, putting green, and a spacious patio designed for making the most of every sunny day. Whether you're lounging poolside or enjoying a casual game of ping pong, this outdoor space was made for fun and relaxation. Upstairs, the second level includes three luxurious king suites with private en-suite baths. The third floor offers four additional bedrooms—three more king suites and a bunk room with two full-over-full bunks, making it ideal for large families or groups. At the top of it all, the rooftop terrace delivers incredible views of Siesta Key Village and the nearby beach. It’s the perfect spot to take in the sunset, sip a cocktail, or stargaze late into the evening. A built-in wet bar completes the experience. This is a rare opportunity to own a one-of-a-kind home in one of Siesta Key’s most coveted locations. With stunning finishes, thoughtful amenities, and a true resort-style feel, this residence offers coastal living at its finest. Schedule your private tour today.

119 Avenida Messina, Siesta Key
$575,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code ⋅ A4654536 MLS ⋅ Active Status ⋅ 5660 BLDG.
SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally situated and directly across the street from the world-renowned Siesta Key Beach, continuously celebrated for its powdery soft, white quartz sands and clear waters. This property is being offered fully furnished and is move in ready, presenting a unique chance to personalize your very own dream retreat whether as a permanent residence or a vacation getaway. This unit beams with natural light throughout, showcasing its rare beauty. With a minimum lease period of one month, up to twelve times a year, it also offers potential for rental income. Rental Proforma attached. As you enter the front doors to this beach oasis, prepare to be impressed by an open-concept kitchen that seamlessly flows into the living and dining areas, extending out to a private screened-in lanai where you can take in partial glimpses of the Gulf, creating a perfect setting for relaxation and entertaining. Need a little space? Both bedrooms feature walk-in closets, providing ample storage and comfort. In addition, the unit overlooks the community's heated pool which is maintained at 85 degrees year-round. This well-maintained community was built in 1970, offering a host of amenities designed for convenience and leisure. Residents have access to a community room with a full kitchen for social gatherings, picnic and grilling areas, elevators, laundry facilities on each floor, and a personal storage unit. In addition, your deeded carport is located just steps from your front door, ensuring ease of access. Recent updates to building include a new roof in 2020, an updated elevator installed in 2019, re-plumbed stacks completed in 2018, the addition of new vinyl fencing in 2021. The quarterly condo association fee covers access to all the amenities, pest control, basic cable, water/sewer services, grounds maintenance, weekend on-site maintenance, and community insurance. Living on Siesta Key means more than just proximity to the beach; it's about embracing a lifestyle where every day feels like a vacation. Start your mornings with a peaceful walk along the shoreline, enjoy paddleboarding in the calm Gulf waters, or partake in beach yoga sessions at sunrise and drum circle Sundays. The island's laid-back atmosphere is complemented by its vibrant community, offering a mix of friendly full-time residents and seasonal visitors. Ready to venture out for some more fun? Siesta Key Village, just a short distance away, is the heart of the island's social scene. Here, you'll find an array of casual bars, eateries, and boutiques, perfect for evening outings or weekend brunches. The community's eclectic vibe ensures there's always something happening, from local festivals to live music events. Other close by attractions include the Ringling Bridge, Downtown Sarasota and St. Armands, close proximity to top rated schools and hospitals, SRQ Airport and University Town Center. Don't let another Season pass you by from owning your own slice of paradise in the sand. Schedule your showing today.

5600 Beach Way Drive Unit 201, Siesta Key
$1,699,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code ⋅ A4654664 MLS ⋅ Active Status ⋅ Sea Gate BLDG.
BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!

2425 Gulf Of Mexico Drive Unit 14B, Longboat Key
$1,325,000
3 Beds ⋅ 2 Baths ⋅ Bird Key Sub SubDv. ⋅ 34236 Zip Code ⋅ A4654386 MLS ⋅ Active Status
Endless possibilities on Bird Key! This prime garden home sits in a location full of potential. Whether you’re looking to renovate and make it your own, start fresh with new construction, or add space to support your lifestyle—this property delivers. The lot is ideal for building a custom home that takes full advantage of the scenery and views. Already have a main residence? This could be the perfect spot for a guest house, studio, or even a car collector’s garage with room for your growing collection. The Bird Key location is convenient and has easy access to so many shops and galleries. Beach access for the beachgoers is enjoyable on Lido Key, which offers beautiful beaches and recreational activities, St Armands for upscale shopping and dining, Also , the Longboat Key Club is a very short distance away, which offers golf and tennis plus several restaurants. Waterfront living is at its best living on Bird Key, which also has a marina and clubhouse.

223 Seagull Lane, Bird Key
$6,945,000
5 Beds ⋅ 6 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code ⋅ A4652926 MLS ⋅ Active Status
A boater's dream and RARE opportunity—One of just 39 homes on this EXCLUSIVE side of St. Armands Circle offering -DIRECT GULF ACCESS- NO FIXED BRIDGES - and NO OBSTACLES. True deep-water dockage that comfortably accommodates a vessel over 60 feet. Enjoy full waterfront views of Sarasota Bay and the iconic downtown Sarasota skyline from every north-facing room in this home. This stunning, gated waterfront estate showcases the timeless elegance of Mediterranean architecture, blending classical design with refined coastal living. Expertly engineered with solid poured concrete walls reinforced by structural steel beams, this residence offers unmatched strength, integrity, and long-term value—an ideal foundation for both luxury and peace of mind. This Venetian-inspired estate is a rare architectural masterpiece, showcasing meticulously hand-applied Venetian plaster walls that exude artisan-crafted elegance—both refined and truly one-of-a-kind. The home features unmatched fit and finish throughout the entire residence. The primary floor of this home is thoughtfully designed for seamless living and exceptional entertaining value. Take in full waterfront views of Sarasota Bay and the downtown skyline while preparing a meal in the master-crafted kitchen or relaxing on the expansive waterfront veranda. The kitchen is an authentic showpiece and a true chef’s dream, featuring professional-grade appliances, a robust gas range with multiple burners, hand-carved cabinetry, and marble flooring throughout. This four-story home is equipped with a whole-house elevator for effortless access to each level. With an expansive extended garage, it’s ideal for car enthusiasts, offering multiple storage bays and additional space for organization. Looking for ease of maintenance? Enjoy the recently installed, top-of-the-line polymer turf surrounding the home. The luxury pool and spa features all brand new equipment and water heater, a premium-grade saltwater chlorination system, complete with full automation and water features. Delivering crystal-clear water and low-maintenance convenience. St. Armands Circle is one of Sarasota’s most coveted and prestigious addresses. This home's premier location places you just steps from Lido Beach. Frequent festivals, classic car shows, and seasonal events make the area lively year-round. Choose from gourmet restaurants, boutique shops, and family-friendly activities as you stroll the Circle. Downtown Sarasota’s theaters, museums, and fine arts venues are just a short drive away. For golf enthusiasts, this home is minutes from The Longboat Key Club—one of Sarasota’s most prestigious private clubs. The club features 45 holes of championship golf across two beautifully maintained courses and a full-service, resort-style experience including a world-class tennis center, private beach, deepwater marina slips, full-service spa, upscale dining, and an active calendar of social events.

290 N Washington Drive, Lido Key
$4,250,000
6 Beds ⋅ 6 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code ⋅ A4653979 MLS ⋅ Active Status
STUNNING ESTATE ON LIDO KEY!!! WELCOME TO YOUR COASTAL DREAM HOME!!! This 6 bedroom 5 1/2 bath property is TURNKEY FURNISHED, has an ELEVATOR to all levels, and boasts vaulted ceilings. The owner spared no expense when building this home. High end designer finishes and attention to detail are evident throughout. The master bedroom is a tranquil oasis and offers a private balcony providing breathtaking views. You will also find a large walk in closet and an oversized bathroom featuring double vanities, free standing bath tub, and a walk in shower. The additional four bedrooms are all en-suite and are laid out perfectly. The chef's kitchen has high end wood cabinets, quartz countertops, stainless steel appliances and a large center island. The great room floor plan is expansive and features high ceilings with wood beams. Step into your outdoor oasis with a private heated pool with a sun shelf, perfect for both kids and adults to soak up the Florida sun. A covered spa ensures year-round enjoyment. The expansive covered patio extends nearly the entire space beneath the home, ample bar-top seating, dining, TVs, and gaming areas, including a pool table and foosball. Convenience is key as you're just a short stroll to Lido Key Beach and or to St. Armand's Circle with wonderful shops and restaurants. With a 2-car garage and space for up to four cars in the driveway, you have ample parking options. This is the ultimate vacation home for you and your family. Currently a successful vacation rental with forward bookings in place.

340 Jackson Drive, Lido Key
$8,925,000
5 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4653251 MLS ⋅ Active Status
This stunning Bayfront estate delivers over 480 feet of pristine Bayfront waterfront on a prime point property. True Longboat Key gold. Special features of this home include five bedrooms, five full bathrooms, hardwood floors, sky-high ceilings plus walls of glass. The home opens to multiple covered terraces built for soaking in endless Bay views and the best of Florida living at its finest. The open-concept layout blends indoor comfort with outdoor style, perfect for hosting or unwinding in total privacy. The kitchen is sleek and spacious with high end Wolf package and Sub Zero ready for gourmet meals or casual bites with a view. The adjoining family room also features a large stone fireplace. The primary suite is a retreat all its own with private terrace access, spa-style bath and water views that never quit. Outside, the lifestyle really takes off. A large Bayfront resort-style pool with a hot tub anchors the backyard, surrounded by multiple fire pits perfect for evening gatherings under the stars. Need space for guests? A separate guest house is available to design to your personal touch, offers total privacy and comfort, ideal for hosting family or friends without sacrificing your own space. This estate isn’t just a home it’s a waterfront playground built for bold living. There's kayak storage and room for multiple docks and all your water toys. The new seawall built in 2010 adds peace of mind. There is a four car garage. This North Longboat property is a must see for anyone seeking a luxurious lifestyle combined with natural beauty. With its modern amenities, prime location, and stunning views, it stands out as a dream home. Don’t miss the opportunity to make this exquisite residence your own. This north Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.

630 De Narvaez Drive, Longboat Key
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