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535 Sanctuary Drive Unit A401, Longboat Key
$3,265,000
3 Beds ⋅ 4 Baths ⋅ Sanctuary SubDv. ⋅ 34228 Zip Code
Welcome to the largest floor plan at Sanctuary, offering over 3,100 square feet of refined coastal elegance with breathtaking Gulf-to-Bay views. This exceptional residence captures both sunrises over the bay and sunsets over the Gulf, delivering a rare, full-spectrum waterfront experience. Designed for elevated living and effortless entertaining, the expansive open-concept floor plan seamlessly blends indoor and outdoor spaces. Walls of glass frame panoramic water views, filling the home with natural light and creating a stunning backdrop from nearly every room. The residence features: Three luxurious ensuite bedrooms, Three full bathrooms plus a beautifully appointed powder room, A grand living and dining area ideal for entertaining, A spacious chef’s kitchen perfectly positioned to enjoy the views, Two private balconies plus an impressive wrap-around balcony, providing multiple vantage points for morning coffee and evening sunsets. Every detail reflects sophisticated coastal design — generous proportions, seamless flow, and expansive outdoor living spaces that elevate the everyday into something extraordinary. This is more than a residence — it is a front-row seat to the Gulf, the Bay, and the beauty of sunrise to sunset living. Additional community features include a separate fully equipped recreation building with state of the art fitness, two lighted Har-Tru tennis courts, saunas, on-site management, and 24 hour guarded entry. All located behind the gates of the Longboat Key Club. Schedule your private preview!

535 Sanctuary Drive Unit A401, Longboat Key
6601 Gulfside Road, Longboat Key
$5,600,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Discover an extraordinary opportunity to own two parcels in a newly developed beachfront enclave, complete with private entry gates when project is complete leading directly to the pristine sugar sands and turquoise waters of the Gulf of Mexico. Parcel one, identified by property ID 7847700154, offers a 2,000-square-foot homesite with 100 feet of direct Gulf frontage. Parcel two, property ID 78477000078, is a sprawling 9,757-square-foot parcel. These two exclusive Gulf-front estates are nestled at the end of North Gulfside Road on Longboat Key, offering unmatched privacy in a secluded cul-de-sac. With endless views, serene surroundings, and ultimate exclusivity, this is a rare chance to create your dream coastal haven. 6509 is also listed if you would like to have a estate size lot.

6601 Gulfside Road, Longboat Key
5965 Gulf Of Mexico Drive, Longboat Key
$38,450,000
11 Beds ⋅ 17 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Under Construction. PRE-AUCTION: Bidder registration deadline: 5 November. Rising on nearly two private Gulf-front acres, this visionary estate is poised to become one of the most architecturally significant residences conceived on Longboat Key. Designed by internationally acclaimed Sweet Sparkman Architecture & Interiors, the sculptural home pairs bold modern form with coastal sensitivity, framing uninterrupted Gulf views from a dramatic foyer, open great room, and sweeping terraces. Dual kitchens, a temperature-controlled wine cellar, dedicated space for a private cinema, and rooftop deck elevate daily living and grand-scale entertaining, while a guest house and pool house extend privacy and flexibility. Lush resort-style grounds unfold to a shimmering pool and spa. Offered at a pivotal stage of construction, the estate presents a rare chance to shape an enduring Gulf-front legacy.

5965 Gulf Of Mexico Drive, Longboat Key
775 Longboat Club Road Unit 401, Longboat Key
$1,395,000
2 Beds ⋅ 2 Baths ⋅ Beaches Of Longboat Key SubDv. ⋅ 34228 Zip Code
Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!

775 Longboat Club Road Unit 401, Longboat Key
775 Longboat Club Road Unit 808, Longboat Key
$2,145,000
3 Beds ⋅ 3 Baths ⋅ Beaches Of Longboat Key SubDv. ⋅ 34228 Zip Code
Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.

775 Longboat Club Road Unit 808, Longboat Key
1211 Gulf Of Mexico Drive Unit 403, Longboat Key
$1,695,000
2 Beds ⋅ 2 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code
Escape to elegance in this tastefully renovated, fully furnished fourth-floor residence at The Promenade on Longboat Key, where luxury meets effortless coastal living. This spacious two-bedroom, two-bath split-floor-plan condo offers breathtaking sunset views overlooking the Gulf of Mexico and beautifully landscaped community grounds. Inside, no detail has been overlooked. The residence features Café Series appliances, Quartzite countertops in the kitchen and primary bath, custom cabinetry with a hidden vent hood, and Luminette motorized blinds throughout. Spa-like bathrooms showcase mosaic glass tile showers, rain showerheads, and Delta Premier fixtures, while large-plank luxury vinyl flooring flows seamlessly through the home. Additional highlights include an Electrolux washer and dryer, designer-finished balcony tiles, and impeccably curated furnishings that complete this turnkey offering. Set on 6.5 acres of Gulf-front paradise, The Promenade delivers an exceptional amenity lifestyle with four Har-Tru tennis courts, a beachfront gazebo, pool and spa, and men’s and women’s health clubs. Residents also enjoy two elegant party rooms, concierge services, an on-site manager, and 24/7 gated security, offering both luxury and peace of mind. Ideally located on the south end of Longboat Key, this residence is minutes from world-class dining, shopping, cultural venues, and medical facilities. Sarasota-Bradenton International Airport is just 20 minutes away, while Sarasota’s renowned attractions—including St. Armands Circle, The Ringling Museum, and Mote Marine Aquarium are easily accessible. Whether you seek serene beachfront living or vibrant coastal experiences, this is more than a home it’s a lifestyle. Welcome to your personal paradise at The Promenade.

1211 Gulf Of Mexico Drive Unit 403, Longboat Key
4835 Gulf Of Mexico Drive Unit 106, Longboat Key
$675,000
2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code
Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

4835 Gulf Of Mexico Drive Unit 106, Longboat Key
4127 Gulf Of Mexico Drive Unit N102, Longboat Key
$4,700,000
3 Beds ⋅ 4 Baths ⋅ La Firenza SubDv. ⋅ 34228 Zip Code
Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.

4127 Gulf Of Mexico Drive Unit N102, Longboat Key
1000 Longboat Club Road Unit 403, Longboat Key
$949,000
2 Beds ⋅ 2 Baths ⋅ Privateer South SubDv. ⋅ 34228 Zip Code
Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach club, while Privateer South offers intimate beachfront living in a 12-story tower at 1000 Longboat Club Road. This fourth-floor corner residence is a fully renovated two-bedroom, two-bath home that captures the essence of coastal elegance. Floor-to-ceiling windows and sliding glass doors open to wraparound balconies with eastern, southern, and partial Gulf views. Begin your mornings with sunrise over Sarasota Bay and the Intracoastal Waterway, as soft hues of pink and gold fill the open living and dining spaces. By afternoon, enjoy sweeping southern views of powder-white sand and turquoise Gulf waters, accompanied by the gentle sound of waves. The interior renovation reflects modern sophistication and comfort. A sleek galley kitchen with quartz countertops, stainless steel appliances, and custom cabinetry flows seamlessly into the bright living-dining area. Neutral tones, shiplap accents, and high-end finishes create an inviting, light-filled space ideal for entertaining or relaxing. The primary suite features desirable southern exposure and a refreshed en-suite bath with dual vanities and a walk-in shower. The second bedroom offers flexibility as a guest room, office, or private retreat, with the guest bath refreshed as well, in a clean, contemporary style. Daily living feels effortlessly indulgent. From the lobby, take the elevator to the heated Gulf-front pool and spa, complete with lounge seating overlooking the shoreline. Manicured pathways lead to private beach access, where dunes, complimentary chairs and umbrellas, and uncrowded sands create the perfect setting for sunset walks and frequent dolphin and pelican sightings. Residents also enjoy beachside grilling, on-site tennis, and the simple pleasures of Gulf coastal living. Gated security, covered parking, and the low-density South tower — with approximately 62 residences — provide both privacy and a welcoming community atmosphere shared by seasonal and full-time residents alike. Evenings on the balcony are unforgettable, with brilliant sunsets fading into star-filled skies over the Gulf. Inside, the open layout invites relaxed dinners, quiet reading, and peaceful nights accompanied by the sound of the water. This beautifully renovated corner residence offers the perfect balance of comfort, elegance, and breathtaking scenery in one of Florida’s most sought-after barrier island communities.

1000 Longboat Club Road Unit 403, Longboat Key
535 Sanctuary Drive Unit C807, Longboat Key
$3,500,000
3 Beds ⋅ 3 Baths ⋅ Sanctuary SubDv. ⋅ 34228 Zip Code
Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

535 Sanctuary Drive Unit C807, Longboat Key
1485 Gulf Of Mexico Drive Unit 303, Longboat Key
$1,395,000
2 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code
Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

1485 Gulf Of Mexico Drive Unit 303, Longboat Key
6489 Gulfside Road, Longboat Key
$13,995,000
4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Ready to live directly on the Gulf? This Seaward Homes Curated Collection residence at 6489 Gulfside is move-in ready, with direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects and staged by Clive Daniel Homes, the home pairs cutting-edge, hurricane enhanced construction with exceptional quality and attention to detail throughout. Set on a coveted 90' Gulf/beach-front lot, the property offers soft sand, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a major beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the island. Gulfside Road is also one of the rare Gulf-side streets set back from the main highway, so the setting feels private and quiet, worlds away from the activity of Gulf of Mexico Drive, just minutes from Whitney Plaza and North Longboat Village, and moments from fine dining at Shore and Mar Vista. The main house is elevated over 15', with 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 square feet of air-conditioned living space, including a grade-level, air-conditioned multipurpose room ready for a home gym, a wellness studio, or whatever fits your lifestyle. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces, one on the main floor and one on the second, are ideal for enjoying the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes take the home to the next level, with large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, premium Longboard™ aluminum architectural details, and a fine light-sand stucco exterior. A resort-like pool and spa are surrounded by lush tropical landscaping, and the four-car garage leaves room to add car lifts. Longboat Key is an 11-mile barrier island just minutes from St. Armands Circle and downtown Sarasota, with Sarasota Bradenton International Airport about 25 minutes away. This is a rare chance to own this level of coastal luxury directly on the Gulf, don't wait!

6489 Gulfside Road, Longboat Key
5231 Gulf Of Mexico Drive Unit 104, Longboat Key
$499,000
1 Beds ⋅ 1 Baths ⋅ Covert Condominium SubDv. ⋅ 34228 Zip Code
Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key
5260 Gulf Of Mexico Drive Unit 403, Longboat Key
$649,999
2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv. ⋅ 34228 Zip Code
This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

5260 Gulf Of Mexico Drive Unit 403, Longboat Key
3060 Grand Bay Boulevard Unit 174, Longboat Key
$1,829,000
2 Beds ⋅ 3 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code
PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

3060 Grand Bay Boulevard Unit 174, Longboat Key
6685 Gulf Of Mexico Drive, Longboat Key
$15,550,000
8 Beds ⋅ 10 Baths ⋅ T J Oxford Subdivision SubDv. ⋅ 34228 Zip Code
Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

6685 Gulf Of Mexico Drive, Longboat Key
1115 Gulf Of Mexico Drive Unit 401, Longboat Key
$875,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
The perfect beach getaway or investment property, look no further. With stunning water views from all new windows and doors, beach access, and appealing lease policy, this 1,172 square-foot 2 bedroom, 2 bath residence in Beachplace is ready to enjoy! Watch stunning sunset views from your southwestern facing, L shaped balcony overlooking beautiful well-manicured lawn, pond, and enchanting Gulf of Mexico waters. This views can also be enjoyed while in the master bedroom. The condo residence is a corner unit, located on the 4th floor with ideal proximity to the building elevator and has wood-look tile throughout. Beachplace is perfectly located on the south end of Longboat Key, minutes from St. Armands, downtown Sarasota, SRQ Airport and much, much more. Community offers on-site management, 24-hour security, a Jr. Olympic-sized swimming pool, and newly designed hot tub area. There are lighted tennis courts, a fitness center and gas grills for the community use.

1115 Gulf Of Mexico Drive Unit 401, Longboat Key
757 Hideaway Bay Drive, Longboat Key
$6,295,000
4 Beds ⋅ 5 Baths ⋅ Hideaway Bay Subdivision SubDv. ⋅ 34228 Zip Code
Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.

757 Hideaway Bay Drive, Longboat Key
230 Sands Point Road Unit 3205, Longboat Key
$996,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, Spa/Wellness Center, white sand beach with umbrellas and waitstaff and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start your Longboat Life today!

230 Sands Point Road Unit 3205, Longboat Key
1065 Gulf Of Mexico Drive Unit 402, Longboat Key
$799,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

1065 Gulf Of Mexico Drive Unit 402, Longboat Key
1591 Gulf Of Mexico Drive Unit 216, Longboat Key
$2,750,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.

1591 Gulf Of Mexico Drive Unit 216, Longboat Key
240 Sands Point Road Unit 4102, Longboat Key
$939,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Highly desirable 1st floor walkdown Junior Suite with Gulf views in Building 4 priced to sell. This completely renovated unit is currently in the hotel program and reported more income through August 2026 than all of 2025. There is an expanded deck in addition to the covered terrace, which provides direct access to the beach. Building 4 is situated farthest north on the gulf side where owners value privacy from the pool activities, but are still close to all of the amenities. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!

240 Sands Point Road Unit 4102, Longboat Key
490 N Shore Road Unit 6, Longboat Key
$699,000
2 Beds ⋅ 3 Baths ⋅ Northgate Of Longboat Key SubDv. ⋅ 34228 Zip Code
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
2425 Gulf Of Mexico Drive Unit 14B, Longboat Key
$1,699,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code
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
1241 Gulf Of Mexico Drive Unit 603, Longboat Key
$3,295,000
3 Beds ⋅ 4 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code
Welcome to this spectacular three bedroom 6th floor southern facing Brighton floor plan located in the south building of the sensational Gulf front Water Club complex on south Longboat Key. Your private elevator opens directly into the foyer which leads to the open floorplan and the sensational views of sandy beach and the Gulf of Mexico. The condo features beautiful wood floors, a gourmet kitchen with high end appliances, granite countertops plus a serene eating area. The spacious master suite is completely private with a large walk-in closet and elegant bath plus adjacent sitting area. The master has sliding glass doors leading to a private terrace with views of the Gulf of Mexico. The southern exposure of this condo bathes it in sunlight and stunning sunrises. The Water Club is a luxurious resort style complex on the beautiful sandy beach and azure waters of the Gulf of Mexico. The Water Club amenities include four tennis courts, a centrally located large pool and spa and a 24 hour staff plus gated access. The 17,000 sq.ft clubhouse features a spa and gym area separate for men and women plus a library and a catering kitchen and ballroom. The Water Club is conveniently located just minutes from award winning restaurants plus Publix and CVS, St Armands Circle, downtown Sarasota and the Longboat Key Club for golf, tennis and restaurants are also nearby.

1241 Gulf Of Mexico Drive Unit 603, Longboat Key
1561 Gulf Of Mexico Drive Unit 403, Longboat Key
$12,750,000
3 Beds ⋅ 4 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the clubroom serves as a fantastic bonus space, featuring a wet bar equipped with an ice maker, bar sink, and wine fridge. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Wolf and Sub-Zero appliances, including a 6-burner gas cooktop, double ovens, and an integrated cabinet front side-by-side refrigerator/freezer. A semi-private elevator with keyless entry transports you directly from your private two-car garage to your residence. The owner’s suite offers a spacious walk-in closet, a luxurious soaking tub, a frameless walk-in shower, and dual vanities with separate water closets. Designed with technology-ready infrastructure, this home allows for easy customization of your automation preferences. Located within the first branded residential community and ultra-luxe 5-star resort hotel on the Gulf, The Residences at The St. Regis Longboat Key blend legendary service with the allure of a serene seaside retreat. Spanning over 17 acres with 800 feet of direct beachfront, residents can indulge in unparalleled amenities, including signature St. Regis Butler and Concierge services, a world-renowned spa, in-residence dining, a resident-only pool and spa, a private clubhouse, a fitness center, and beachside cabanas. Discover a life of luxury and leisure at The Residences at The St. Regis Longboat Key—where every day feels like a getaway. The owner will consider a lease purchase with acceptable terms on this residence.

1561 Gulf Of Mexico Drive Unit 403, Longboat Key
1591 Gulf Of Mexico Drive Unit 413, Longboat Key
$4,399,000
2 Beds ⋅ 3 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Discover an elegant and gracious two-bedroom residence featuring spacious rooms, expansive glass windows, and soaring ceilings that create an airy, inviting atmosphere. The well-appointed gourmet kitchen boasts top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, perfect for culinary enthusiasts. Retreat to the large owner's suite, complete with a luxurious primary bath that features double vanities, a deep soaking tub, a frameless walk-in shower, and a private water closet. The residence is being sold furnished from Restoration Hardware. Host unforgettable gatherings on your terrace, equipped with an outdoor gas grill and views of Sarasota Bayfront. Residents will have the ease and convenience of a private 2-car garage on the first level with easy access to your semi-private elevator opening directly into your residence. Nestled within the first branded residential community and ultra-luxe 5-star resort on the Gulf of Mexico, The Residences at The St. Regis Longboat Key blend legendary service with the serene allure of a seaside getaway on the secluded barrier island of Longboat Key, FL. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience luxury living at its finest. Welcome home to The St. Regis Longboat Key. The owner will consider a lease purchase with acceptable terms on this residence.

1591 Gulf Of Mexico Drive Unit 413, Longboat Key