Refine Search
Map
Sort by
2141 Harbourside Drive Unit 1203, Longboat Key
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code
Welcome to an exceptional turnkey, furnished, and newly renovated villa in Harbour Oaks, ideally located within Bay Isles in the heart of Longboat Key. This end-unit residence offers the right blend of natural warmth, contemporary finishes, and curated style. With high ceilings, abundant natural light, and a spacious floor plan, the home feels remarkably open and inviting. Warm hickory wood floors extend throughout the living areas, adding richness and character to the home's fresh, contemporary design. The impressive kitchen features an oversized island with a dramatic waterfall-edge quartz countertop in a concrete-inspired finish that is both beautiful and requires no maintenance. Stainless steel GE Café appliances complement the kitchen, while a custom coffee bar with floating shelves and a stunning backsplash adds another layer of style and functionality. For evening entertaining, the custom built-in bar is a standout feature, topped with a beautiful live-edge Saman wood countertop. It is the perfect place to pour a cocktail and enjoy the relaxed Longboat Key lifestyle. The spacious dining area is adjacent to a beautiful atrium that fills the home with magnificent natural light. Newly tiled with stone. It is screened overhead, allowing the sliders to be opened, creating a wonderful connection to the outdoors and inviting fresh air into the dining and living space. The oversized screened lanai is another exceptional feature, with brand-new stone pavers and a new panoramic screen enclosure. Lush new greenery surrounds the lanai, creating a private tropical setting that feels like your own outdoor retreat. The primary suite is a luxurious sanctuary with three closets, including a walk-in, all outfitted with customized shelving for exceptional organization. The beautifully renovated primary bath features Carrera marble countertops, dual sinks, warm gold fixtures, and a separate water closet. The spacious second bedroom offers a private ensuite bath with a marble-floored shower, Carrera marble vanity top, and a separate water closet. The generous third bedroom is currently used as a fitness room but offers ample space for a comfortable bedroom, along with a generous closet. Storage is abundant throughout the home. A beautifully appointed powder room serves guests. As an end unit, this villa enjoys a large manicured grass side yard and an enviable location just steps from the community pool. This home has an attached 2-car garage with a new epoxy-coated floor and an additional fridge.  An especially wonderful benefit of living in Bay Isles is automatic membership in the Bay Isles Beach Club, just minutes away on Longboat Key's beautiful sandy beaches. Enjoy five acres of beachfront, gated parking, beach chair storage, newly renovated restrooms, grills and picnic tables—a wonderful setting for family and friends to gather, sunset strolls, and memories to last a lifetime. Close proximity to the Longboat Key Club with 45 holes of golf, 5 private restaurants, and a world-class tennis and pickleball facility. This residence is more than a renovation; it is a completely reimagined home where thoughtful design, beautiful materials, and the ease of living the good life on Longboat Key come together beautifully.

2141 Harbourside Drive Unit 1203, Longboat Key
1916 Harbourside Drive Unit 804, Longboat Key
$1,599,000
4 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
FAIRWAY BAY’S FINEST — WATERFRONT LUXURY " END UNIT " WITH UNPARALLELED VIEWS Experience the ultimate Longboat Key lifestyle in this exceptional, move-in-ready waterfront residence in the prestigious gated Bay Isles community of Fairway Bay. Recently renovated and thoughtfully designed, this stunning 4-bedroom, 3-bath home offers more than 2,750 square feet of beautifully appointed living space, framed by expansive windows and soaring ceilings that invite an abundance of natural light. From nearly every room, enjoy breathtaking panoramic views across Sarasota Bay to the iconic Ringling Bridge and downtown Sarasota. The seamless open-concept design creates an effortless flow between the sophisticated great room with a fireplace, dining room & beautifully appointed kitchen, featuring high-end appliances and exquisite quartz and marble finishes throughout the home. The light-colored wide planked wood floors add great warmth & grounding while the whole family gathers around the kitchen island or wrap-around sectional to enjoy a movie together! Designed for both elegant entertaining and relaxed coastal living, the residence offers two luxurious primary suite options one on the main floor or the panoramic terraced 2nd floor, including a private second-floor retreat that serves as an office or the 4th bedroom enjoying a sunrise terrace with a colorful flowerbox to enhance your relaxation. A versatile lower-level bonus room offers ample space for hosting family and friends or creating a private fitness studio, media room, or game room. The previous owner combined recreation and guest accommodations, furnishing the space with two king beds, an oversized couch, a ping-pong table, and a shuffleboard table. Step onto your private screened terrace and enjoy sweeping views across Sarasota Bay to downtown Sarasota, framed by spectacular sunrises and sunsets. Just steps away, your private dock accommodates a boat up to 40 feet, inviting spontaneous excursions along the Intracoastal Waterway and into the Gulf of Mexico. When it’s time to unwind, Fairway Bay offers an array of resort-style amenities, including access to the private Bay Isles Beach Club, a pool, spa, clubhouse, and tennis and pickleball courts. Scenic walking and biking paths invite outdoor exploration, while convenient kayaking access offers opportunities to discover the area’s abundant coastal wildlife. Enjoy convenient access to your private Bay Isles Beach Club via a pedestrian and bicycle tunnel, allowing you to reach the beach without crossing Gulf of Mexico Drive—just one of the many features this fabulous community offers. You’re also minutes from The Resort at Longboat Key Club, with its golf, restaurants, and marina, and a short drive from St. Armands Circle for exceptional dining, shopping, and art experiences. This is more than a beautiful home—it is a private waterfront retreat offering the very best of Longboat Key living. Simply arrive, unpack and begin enjoying the waterfront luxury lifestyle you deserve.

1916 Harbourside Drive Unit 804, Longboat Key
3710 Gulf Of Mexico Drive Unit A3, Longboat Key
$525,000
2 Beds ⋅ 2 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code
DIRECT GULF FRONT/OCEAN VIEWS, FULLY FURNISHED, ELEVATED, AND BRING YOUR BOAT (BOAT SLIP opportunity for a small monthly rental fee at the NEW community marina) Beach Retreat with numerous improvements. Longboat Key living doesn't get any better than this. Located in a highly desirable waterfront co-op community, this home was raised 4 ft to enjoy more of the beautiful ocean views. All new windows with the front windows replaced with large picture windows for year round gulf/ocean views. Additional new updates include all new windows, new window coverings, new doors, new kitchen remodel which includes new countertops and painted cabinets, new bedroom fans, newly redone dining area, refreshed outdoor bathhouse, (included for description purposes as 1 of 2 bathrooms), new HVAC duct work and heating element, new Astro turf lawn, new outdoor lighting, newly painted interior, beautifully redone outdoor patio. Gulfshore of Longboat Key is perfectly situated between the Gulf of America and the Bay for beach to bay access. It has approximately 450-500 ft of private deeded beach access on the powdery sand and views of the turquoise blue water. It also has a new marina on Sarasota Bay, a large, heated community pool, a remodeled clubhouse with a commerical kitchen, a well-maintained community with a professional on-site manager, and very reasonable HOA fees! Gulfshores is a 55+ community and does not permit pets or rentals. Come live The Longboat Key Life.

3710 Gulf Of Mexico Drive Unit A3, Longboat Key
6561 Bayou Hammock Road, Longboat Key
$3,495,000
4 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34228 Zip Code
Beyond the gates of Bayou Hammock, where just 11 residences share one of north Longboat Key’s most private waterfront settings, a true coastal retreat awaits. Arrive through one of two private gated entrances, where refreshed tropical landscaping and a charming butterfly garden welcome you home. Set on an expansive 0.83-acre lot with approximately 150 feet of direct canal frontage, the property offers sailboat water and room to accommodate vessels up to approximately 70 feet. Thoughtfully reimagined by the current owner, the beautifully renovated bungalow blends timeless Old Florida character with modern comfort. The 3-bedroom, 3-bathroom main residence is complemented by an attached guest casita with its own bedroom and bathroom, creating a total of 4 bedrooms, 4 bathrooms, and approximately 2,600 square feet of air-conditioned living space. Distinctive keystone accents will continue to develop a rich, natural patina in the coastal climate, while impact-rated windows and doors, a new standing-seam metal roof, and an attached one-car garage provide lasting value and peace of mind. Life here unfolds outdoors. Begin the morning beside the pool, rinse off beneath the outdoor shower after an afternoon on the water, or step onto the brand-new dock and set out from one of two new 10,000-pound boat lifts. Spend the day boating, fishing, and exploring the surrounding waterways before returning to your own peaceful hideaway. Just moments from the beaches, dining, and relaxed charm of north Longboat Key and nearby Anna Maria Island, this exceptional property is also zoned for Anna Maria Elementary School. More than a waterfront home, it is a private island sanctuary offering rare space, remarkable boating access, and an unhurried way of life.

6561 Bayou Hammock Road, Longboat Key
1591 Gulf Of Mexico Drive Unit 618, Longboat Key
$12,500,000
4 Beds ⋅ 6 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Experience an extraordinary standard of beachfront luxury from this spectacular penthouse residence at the prestigious St. Regis Longboat Key. Showcasing breathtaking panoramic views of the Gulf of Mexico and Sarasota Bay, this exceptional home offers an unparalleled blend of sophistication, privacy, and world-class design. Spanning approximately 5,320 square feet, the residence features four spacious bedrooms, five full baths, and one half bath, thoughtfully designed to provide the ultimate in comfort and elegance. Expansive walls of glass frame mesmerizing water views from nearly every room, while the spectacular 1736 square foot wraparound terrace creates seamless indoor-outdoor living. Enjoy your own private plunge pool, outdoor gas grill, and multiple entertaining areas perfectly positioned to capture stunning sunrises over the bay and unforgettable sunsets across the Gulf. The interiors have been exquisitely curated by award-winning interior designer Kurt Lucas, with every detail reflecting impeccable craftsmanship, timeless elegance, and refined coastal luxury. The residence is offered fully furnished, allowing for an effortless transition into an exceptional waterfront lifestyle. Additional features include a private three-car garage. The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include 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 the finest in fractional luxury living at The St. Regis Longboat Key.

1591 Gulf Of Mexico Drive Unit 618, Longboat Key
760 Longboat Court, Longboat Key
$840,000
3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout.The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

760 Longboat Court, Longboat Key
1561 Gulf Of Mexico Drive Unit 404, Longboat Key
$12,750,000
3 Beds ⋅ 4 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Presented in the most coveted beachfront enclave at The St. Regis Longboat Key Resort, this is a rare opportunity to own a spectacular residence in the prestigious Armand building — the closest to the Gulf, with breathtaking, unobstructed views of the Gulf of Mexico. Encompassing nearly 5,000 square feet and offered fully furnished, this extraordinary home was masterfully designed by the award-winning Rowland and Broughton of Aspen, Colorado. Thoughtfully curated throughout, it lives like a private single-family home while enjoying the legendary St. Regis services and amenities, including butler service and in-residence dining. The gracious great room is designed for effortless entertaining, featuring porcelain wood plank flooring and dramatic accordion doors that fully retract to a sprawling terrace with a private gas grill and panoramic views of the Gulf, resort, and saltwater lagoon — creating seamless indoor-outdoor living. The chef’s kitchen is a true showpiece, anchored by a large statement island clad in exquisite Pininfarina Crystal quartzite with a dramatic waterfall edge — blending sculptural beauty with everyday functionality. The space is impeccably appointed with dual Cove dishwashers, a Wolf six-burner cooktop, Wolf double ovens and microwave, and a Sub-Zero refrigerator. A charming breakfast area offers built-in storage and shelving, along with an ice maker and beverage refrigerator for ultimate convenience. A private club room provides the perfect setting for lounging or game day gatherings, highlighted by custom built-ins and striking in-wall wine storage. The luxurious owner’s suite captures sweeping Gulf views and opens directly onto the expansive terrace. A stunning feature wall wrapped in Bijou Knits wallpaper by Phillip Jeffries adds refined texture and sophistication, complementing the custom built-ins that define this serene retreat. The spa-inspired bath features dual oversized vanities (including a dedicated makeup area), illuminated mirrors, a soaking tub, seamless glass shower, two private water closets with Toto electric toilets, and custom closets. Two additional guest suites offer comfort and privacy. The second features custom built-ins with a king Murphy bed, integrated desk, generous closets, and a bath with double vanities and glass shower, opening to terrace views of Sarasota Bay. The third is equally spacious, also opening to the terrace with bay views and offering double vanities and custom closets. An elegant laundry room continues the home’s elevated aesthetic with custom cabinetry, a utility sink, and SM Quartz by Santa Margherita countertops. Throughout, porcelain wood plank floors, electronic shades, and a state-of-the-art Crestron smart home system enhance everyday living. The integrated technology package — valued at approximately $400,000 — controls lighting, blinds, televisions, and music throughout the home. This is an exceptional opportunity to own one of the most refined residences on Longboat Key — where five-star resort living meets the privacy and comfort of a grand coastal home. Residents enjoy a private clubhouse with fitness center, resident-only pool and spa, St. Regis Butler and Concierge services, an oceanfront spa, dining venues, beachfront cabanas, lazy river, and saltwater lagoon. Set on 17 acres of pristine beachfront just 3.5 miles from St. Armands Circle, this home invites you to embrace the legendary St. Regis lifestyle.

1561 Gulf Of Mexico Drive Unit 404, Longboat Key
707 Saint Judes Drive S Unit 1, Longboat Key
$364,000
1 Beds ⋅ 1 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code
Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

707 Saint Judes Drive S Unit 1, Longboat Key
711 Spanish Drive S Unit 211, Longboat Key
$450,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Discover the best of Longboat Key living in this beautifully renovated 2-bedroom, 2-bath first-floor villa in the sought-after Spanish Main Yacht Club. Offering 1,327 square feet of light-filled living space, this south-facing residence features a stunning vaulted open-beam ceiling, new kitchen with wood cabinetry, solid-surface counters, stainless steel appliances, oversized island and breakfast bar, plus luxury vinyl and tile flooring throughout. The spacious primary suite includes a walk-in closet and beautifully renovated en-suite bath with walk-in shower, while the guest bedroom and bath are equally well appointed. A bright Florida room adds flexible living space and includes a stacked washer and dryer. Enjoy a brick patio, storage area, hurricane-rated windows and doors, ceiling fans, block construction, tile roof and assigned carport. Spanish Main Yacht Club offers deeded private beach access, heated community pool, clubhouse, shuffleboard, kayak storage and a coveted 40-slip private marina. A boat slip is currently available for lease, making this an exceptional opportunity for boating enthusiasts. Enjoy easy access to boating and fishing, plus beautiful Gulf sunsets just a short stroll away. Ideally located minutes from St. Armands Circle, Sarasota dining, shopping, arts and entertainment, and an easy drive to Anna Maria Island. Association fees include water, sewer, trash, grounds and pool maintenance, management, common-area expenses and private road maintenance. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually.

711 Spanish Drive S Unit 211, Longboat Key
448 Gulf Of Mexico Drive Unit A104, Longboat Key
$725,000
2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code
Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour, has its own private marina with no wait list, and is just one bridge to the Gulf! Beach access is within minutes from several locations on Longboat, Lido and Anna Maria Island. With a Base Flood Elevation of 10 Ft, this unit was High and Dry during the storms of 2024. It has been exquisitely redesigned with upscale quartz and Cambria counter tops, ceramic and porcelain tile flooring and Bosch Appliances. There is plenty of storage available with the pantry and built in closets. Bay Harbour is a South Longboat Key community of 39 units in two buildings with a private pool, easily accessible pool baths, community room and fitness center. Each unit has assigned carport parking and separate storage. A well-managed and well-maintained community with reserves; the condo fees are among the lowest on the gulf!

448 Gulf Of Mexico Drive Unit A104, Longboat Key
914 Spanish Drive S Unit 76, Longboat Key
$550,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after 55+ community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bathroom residence is offered fully furnished turnkey with all brand-new, high-end coastal furnishings. Ideally situated just steps from the active marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises—you'll also enjoy Gulf-side beach sunsets just a short stroll away. Thoughtfully designed, the home offers premium mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined, move-in ready living experience from the moment you arrive. Residents enjoy access to a fantastic array of community amenities, including a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, and shuffleboard courts. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a scenic drive to Anna Maria Island, this property offers the perfect blend of active-adult tranquility and local accessibility. Whether you are boating, fishing, or relaxing in the bright, inviting Florida room, this is a rare opportunity to live the ultimate Longboat Key lifestyle.

914 Spanish Drive S Unit 76, Longboat Key
683 Spanish Drive S Unit 214, Longboat Key
$450,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Experience the ultimate Longboat Key lifestyle in this beautifully renovated single-story villa located in the highly sought-after 55+ waterfront community of Spanish Main Yacht Club. This move-in-ready 2-bedroom, 2-bath residence features a bright, open floor plan, brand-new appliances, updated finishes throughout, and a spacious Florida room perfect for relaxing or entertaining. Ideally situated just steps from the community marina, enjoy peaceful mornings watching manatees and dolphins while taking in breathtaking sunrise views over Sarasota Bay. Deeded private beach access to the Gulf of Mexico is just a short stroll away, offering unforgettable sunset walks along the sugar-sand beaches. Residents enjoy a maintenance-free lifestyle with exceptional amenities, including a heated community pool, clubhouse, library, shuffleboard courts, and marina with boat docks and kayak storage (subject to availability). An active social environment makes Spanish Main Yacht Club one of Longboat Key's most desirable waterfront communities. Conveniently located just minutes from the world-class shopping and dining of St. Armands Circle and the charm of Anna Maria Island, this villa is ideal as a year-round residence, seasonal getaway, or investment opportunity. Don't miss your chance to own a slice of paradise on Longboat Key.

683 Spanish Drive S Unit 214, Longboat Key
2350 Harbour Oaks Drive, Longboat Key
$950,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code
Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key
4234 Gulf Of Mexico Drive Unit M1, Longboat Key
$649,000
2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code
COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!

4234 Gulf Of Mexico Drive Unit M1, Longboat Key
3527 Fair Oaks Lane, Longboat Key
$2,300,000
4 Beds ⋅ 5 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code
Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.

3527 Fair Oaks Lane, Longboat Key
1050 Longboat Club Road Unit 903, Longboat Key
$995,000
2 Beds ⋅ 2 Baths ⋅ Privateer North SubDv. ⋅ 34228 Zip Code
Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this beautifully renovated corner residence blends sweeping views, refined finishes and effortless coastal living. Offered TURNKEY FURNISHED, the 2-bedroom, 2-bath home looks out across the golf course, Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline, creating a view that shifts beautifully from morning light to evening sparkle. Inside, the renovation is immediately apparent. Clean neutral finishes, recessed lighting, crisp white trim and an open, comfortable floor plan keep the focus on the scenery beyond the glass. All glass is high-impact, hurricane-rated, and the residence also includes hurricane shutters for added peace of mind. The kitchen is designed for both everyday living and easy entertaining, with quartz countertops, custom cabinetry, high-end appliances, a wine refrigerator and detailed tilework. An inviting eat-in area frames bay views, bringing the water into daily life. The living and dining areas open to a terrace overlooking manicured grounds, the golf course and the bay beyond. Both bedroom suites are generously sized with walk-in closets, and the primary suite enjoys its own private terrace. The updated baths feature tasteful finishes, including a beautifully tiled walk-in shower in the primary bath. Privateer North offers a true beachfront lifestyle with a secure lobby, on-site management, heated pool and spa, fitness center, tennis and pickleball courts, social spaces and private beach access. For those seeking an even broader resort experience, optional membership at the Longboat Key Club offers access to 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining, beach and pool facilities, spa, fitness, wellness programming, social events and marina amenities. Located on the sought-after south end of Longboat Key, the residence is just minutes from St. Armands Circle, downtown Sarasota, fine dining, shopping, arts venues and the area’s best coastal amenities.

1050 Longboat Club Road Unit 903, Longboat Key
3040 Gulf Of Mexico Drive Unit 3, Longboat Key
$1,899,000
4 Beds ⋅ 3 Baths ⋅ Triton Cove SubDv. ⋅ 34228 Zip Code
Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don’t miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!

3040 Gulf Of Mexico Drive Unit 3, 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
531 Sutton Place, Longboat Key
$529,000
2 Beds ⋅ 2 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code
Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized garage for bikes, beach chairs, and island gear. The renovated kitchen features quartz countertops and Bosch appliances, and both bedrooms include walk-in closets and fully tiled baths. Unwind on two enclosed balconies overlooking a tranquil pond, then lock up and travel with confidence. Centrally located mid-island, Sutton Place offers the perfect blend of resort-style amenities in a beautiful setting.

531 Sutton Place, Longboat Key
5005 Gulf Of Mexico Drive Unit 4, Longboat Key
$7,495,000
4 Beds ⋅ 5 Baths ⋅ Bonaire Bayou SubDv. ⋅ 34228 Zip Code
Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

5005 Gulf Of Mexico Drive Unit 4, Longboat Key