Location: Longboat Key
Do Not Show Listings
569 BAYVIEW DR, LONGBOAT KEY, FL 34228
$4,695,000293 Days on yellowkey MLS ID: A4661312
REDUCED by $155,000 (3.2%) on 05/01/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Bayview EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,064
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: New Construction. Experience the pinnacle of waterfront luxury with this brand-new construction home in the heart of Longboat Key competitively priced and ready for its next owner. Situated on a private canal, this 4-bedroom plus den, 4,106 sqft residence offers the perfect blend of modern elegance and coastal charm. Designed for seamless indoor-outdoor living, the home features two lanais, a private pool with a spa, and an elevated foundation at 9.5 feet. Boating enthusiasts will appreciate the 10,000-lb boat dock and quick access to the Gulf of Mexico for endless days on the water. Inside, enjoy engineered hardwood flooring throughout, quartz countertops in every space, and a large walk-in pantry. The thoughtfully designed layout includes two laundry rooms for added convenience. Nestled in a quiet, private setting, yet just minutes from Longboat Key’s pristine beaches, golf courses, and fine dining, this home is a rare find. Don’t miss the chance to own a waterfront masterpiece in one of Florida’s most desirable locations.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$3,890,000464 Days on yellowkey MLS ID: A4640902
Bed: 5 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 4176 Built: 2025 Tax: $7,998 (2024)Community: Buttonwood HarborSpa: YesSingle Family
Taxes:$7,998
Elementary School: None
High School: None
Middle School: None
Remarks: New Construction.... GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafted Homes, perfectly positioned on Longboat Key with breathtaking Gulf and Bay views. This 13 FEET ELEVATED, hurricane-fortified residence offers 5 bedrooms, 5 full bathrooms, and 2 partial bathrooms across 4,176 square feet of luxurious living space. Home has elevator shaft blocked in and ready to receive elevator mechanics. Designed for both elegance and functionality, this home features three expansive outdoor living spaces, including two private balconies and a stunning rooftop deck, perfect for capturing the serene Gulf sunsets. The open-concept great room flows effortlessly into the gourmet kitchen, creating an entertainer’s dream, while the second-floor club room offers a private retreat for relaxation. Outdoors, a private pool and spa provide a tranquil escape, while the 5+ car garage ensures ample storage for vehicles and beach essentials. Located just steps from the beach and steps to the upcoming retail and dining destination (Est. Fall 2025), this home also offers access to a community marina with available boat slips, making it ideal for boating enthusiasts. Experience the pinnacle of modern coastal luxury in this exceptional Longboat Key residence—where timeless design, breathtaking views, and an unparalleled location create the ultimate island retreat.
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,495,000218 Days on yellowkey MLS ID: A4669195
REDUCED by $200,000 (4.3%) on 05/21/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.
7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,995,000Listed 05/27/2026 8:12AM MLS ID: A4694196
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2721 Built: 2010Monthly Fee: $317 Tax: $17,255 (2025)Community: Jew Fish KeySingle Family
Taxes:$17,255
Tax Year: 2025
Remarks: Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades. The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island. Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets. The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests. The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise. Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment. Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle. Turn Key - Furnished.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$4,999,000Listed 05/26/2026 5:02PM MLS ID: A4694394
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3842 Built: 2000Monthly Fee: $833 Tax: $29,486 (2025)Community: Manchester BaySpa: YesSingle Family
Taxes:$29,486
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,699,999215 Days on yellowkey MLS ID: A4669533
REDUCED by $100,000 (2.6%) on 05/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1173 Built: 1955 Tax: $36,688 (2024)Community: Coquina BeachSpa: NoSingle Family
Taxes:$36,688
Remarks: BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,550,000240 Days on yellowkey MLS ID: A4666688
REDUCED by $200,000 (4.2%) on 04/29/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Julie Klick (941-780-6001)
2945 PYRULA DR, LONGBOAT KEY, FL 34228
$3,125,00012 Days on yellowkey MLS ID: O6408404
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3815 Built: 2024 Tax: $36,325 (2025)Community: Coquina BeachSpa: YesSingle Family
Taxes:$36,325
Remarks: A contemporary masterpiece awaits Your going to love this house !, constructed in 2024 and completed in December of 2025 this newly built residence blends contemporary architecture with uncompromising craftsmanship. The craftsmanship, and finishing touches puts this property in a class by itself when making your buying comparisons. Worth repeating….Your going to love this house! Step into more than 3,800 square feet of modern design perfection ideally located in one of Longboat Keys most coveted neighborhoods. Just minutes on foot brings you to pristine beach access or a tee time at the prestigious Longboat Keys club. Seamless indoor- Outdoor living, a stunning floor to ceiling glass wall sets the tone from the moment you walk in revealing a private courtyard that feels like your own luxury resort, complete with an elegant pool, a relaxing spa, and a fully equipped outdoor kitchen and dining area. This harmonious flow creates an exceptional living experience where the outdoors becomes an extension of the home . Refined interiors inside , warm oak wood flooring runs throughout the home beautifully paired with stone accents , sleek cabinetry , and high end finishes. The chef designed kitchen is crafted for culinary excellence and features quartzite countertops prized for their durability, beauty, and unmistakably high end character. The primary suite is a serene retreat with glass walls overlooking the courtyard , a soaking tub , a separate shower, and generous storage. Spaces designed for comfort the home offers five bedrooms including An in law suite with a kitchenette, private laundry, spacious bedroom, and walk in shower. An additional bedroom on the main level with its own private balcony . Upstairs two guest suites connected by a bright relaxation area with courtyard views through the floor to ceiling glass. Striking modern architecture, the exterior showcases clean contemporary lines enhanced by rare hand selected stone and rich custom woodwork. Come visit this spectacular offering. ..
Listing is courtesy of: PROPERTIO (888-817-3383)
Listing Agent: Alin Zdroba (888-817-3383)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000197 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Remarks: A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
Listing Agent: John August (941-320-9795)
560 HARBOR POINT RD, LONGBOAT KEY, FL 34228
$9,700,000202 Days on yellowkey MLS ID: A4671218
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5245 Built: 2011Monthly Fee: $802 Tax: $46,237 (2025)Community: Bay IslesSpa: NoSingle Family
Taxes:$46,237
Remarks: Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jonathan Fox, Pa (941-544-6649)
6851 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,775,000117 Days on yellowkey MLS ID: A4675356
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2643 Built: 1986 Tax: $9,196 (2024)Community: Longbeach On Longboat KeySingle Family
Taxes:$9,196
Remarks: Welcome to 6851 Longboat Drive South, a completely renovated waterfront retreat offering the best of Longboat Key living. This exceptional residence features four bedrooms and four baths, including a private guest suite above the garage, and office/gym space, making it ideal for hosting family and friends in comfort and style. Designed with coastal elegance in mind, the home showcases light-filled living spaces, a modern open layout and high-quality finishes throughout. The seamless indoor-outdoor flow leads to tranquil waterfront views, ideal for entertaining or unwinding after a day on the water. Boaters will appreciate the private dock, providing direct access to the bay and making it easy to enjoy fishing, cruising or sunset rides right from your backyard. Every detail has been thoughtfully updated, offering peace of mind and turnkey convenience. Just minutes from the Gulf beaches, St. Armands Circle and Longboat Key Club, this property delivers a rare opportunity to own a move-in-ready waterfront home in one of Florida’s sought-after island communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Barbara Szumski (941-232-8776)
501 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,018,375309 Days on yellowkey MLS ID: TB8398888
REDUCED by $50,000 (4.7%) on 05/08/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1708 Built: 1972 Tax: $13,238 (2024)Community: Sleepy Lagoon ParkSpa: NoSingle Family
Taxes:$13,238
Remarks: Some homes whisper. Others make a statement. 501 De Narvaez Drive commands attention—with bold architecture, elegant updates, and a prime waterfront location that elevates the Florida lifestyle into something exceptional. Nestled on a quiet corner lot in the coveted Sleepy Lagoon Park neighborhood, this home is your gateway to prestige, privacy, and the purest form of coastal living. Spanning 1,708 square feet of refined single-story living, this 3-bedroom, 2.5-bath residence is a masterclass in modern comfort and timeless materials. Designed with block construction and finished in stucco with a durable metal roof, the home is as solid as it is stylish. Inside, terrazzo flooring sweeps across the entire home, providing a sleek and enduring foundation underfoot. Enter into a light-drenched open floor plan, where the layout has been carefully crafted for entertaining, lounging, and effortless day-to-day living. The living room flows into a dining space and gourmet kitchen—outfitted with stone counters, solid surface tops, a spacious island, and stainless steel appliances including a convection oven and cooktop. Whether you’re entertaining guests or enjoying a peaceful morning coffee, every room connects you to the water and the outdoors. The primary suite is an owner’s haven, complete with a walk-in closet and full bath featuring a tub/shower combination. Two additional bedrooms—each with walk-in closets—offer comfort, functionality, and flexibility. A second full bath, half bath, and spacious laundry area provide all the elements of ease and convenience. But what truly defines this home is what lies beyond the doors. A private, heated pool, enclosed within a screened lanai, becomes your year-round sanctuary. The oversized covered deck is perfect for afternoon shade or sunset cocktails. And then there’s the water: with direct canal access to the Intracoastal Waterway, this home is a dream for boaters. The 2022 composite dock and concrete seawall are in pristine condition and ready for your vessel. No HOA means you can live your way, and with 1-month minimum leases allowed (rental license required), this property also offers incredible short- or long-term rental potential. Add in a two-car garage, central air, electric heat, public water/sewer, and fiber optic internet, and you have every modern amenity at your fingertips. This is more than just a home—it’s a statement of lifestyle. A bold, beautiful, and rare opportunity to own in one of Longboat Key’s most established and beloved communities, just moments from world-class beaches, golf, fine dining, and everything the Sarasota area has to offer. For the visionary buyer who seeks distinction, privacy, and water access—501 De Narvaez is where your story begins.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,0005 Days on yellowkey MLS ID: A4694532
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4154 Built: 1994Monthly Fee: $833 Tax: $22,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$22,710
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Miriam Pearson (941-726-4687)
3620 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$3,150,00014 Days on yellowkey MLS ID: A4693553
Bed: 3 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3666 Built: 1991Monthly Fee: $833 Tax: $27,037 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$27,037
Remarks: Come for a visit and you will want to stay and make it yours! Strategically set back from the road, and appropriately positioned on this oversized lot, to allow for an abundance of private waterfront splendor. The expansive paver patio, with oversized pool, spa, outdoor kitchen, and fully equipped pool bath make this the prime setting for endless entertainment and fun with family and friends. Bay views expand over the mangroves to the rookeries and night lights of the Key as you take in the setting sun over Buttonwood Harbor. Get your fishing pole and binoculars ready because enjoyment is an every day event from your dock watching the beautiful Florida feather-life soar thru the skies or dropping a line to hook a surprise catch! Love the boating life? Great- your private dock awaits mooring of its next floating occupant! Upon entry you will be greeted with a customized deco- entry door offset with etched glass above. Inside this spacious home you will find three en-suite bedrooms with a highly possible 4th en-suite in the loft space. The interior space offers marble floors thru-out the entire residence, including the striking marble staircase, and ceilings that reach to great heights allowing for transom windows and a wall of glass to incorporate natural lighting and this amazing view. Like cocktails and eating? A home hi-lite is the wet bar which can serve multiple purposes- bar, buffet, or even a desk, centrally positioned between kitchen, living, dining and family room areas so that no one is too far from that beloved bartender or the delectable fare! Love art? These walls were meant for displaying the finest of your collection. This is a fabulous floorplan with a very separated bedroom layout providing plenty of space for all to spread out and make themselves comfortable. Located in Bay Isles, this home offers guarded, gated access and also deeded access to the Bay Isles Beach Club.
Listing Agent: Cindy Schatzle (941-587-7556)
3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228
$1,399,99982 Days on yellowkey MLS ID: A4684840
REDUCED by $159,001 (10.2%) on 05/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2579 Built: 1998Monthly Fee: $833 Tax: $17,916 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$17,916
Remarks: Nestled behind the gates of Queens Harbour in Bay Isles, this exceptional single-story home offers a rare blend of privacy, space, and effortless Longboat Key living—perfectly positioned on a quiet cul-de-sac with sweeping views along the 4th hole of the Longboat Key Club’s Blue Heron golf course. Spanning approximately 2,579 sq. ft., the thoughtfully designed floor plan features three bedrooms, two full baths, and a half bath, with flexible spaces that adapt beautifully to your lifestyle. A large, dedicated office/den with beautiful glass French doors and custom cabinetry offers outstanding flexibility and can serve as an additional sleeping space if desired. Inside, soaring 14-foot ceilings, rich wood flooring, and an open living-and-dining layout create an airy, welcoming atmosphere. A generous great room is framed by walls of sliding glass doors, opening to the pool and patio for seamless indoor-outdoor living—ideal for entertaining or simply unwinding with tranquil golf course views. The kitchen is perfectly placed for everyday living and gathering, featuring solid wood cabinetry, stone countertops, a center island with a veggie sink, pantry storage, a gas cooktop, and stainless-steel appliances. Two generous guest suites are ideally situated in this split plan, sharing a full bath with the ability to be closed off from the main living area. The private primary suite is a true retreat with golf course views across your private pool and spa. The spa fountain’s soft, flowing water creates a soothing backdrop that drifts into the bedroom through the sliding door access to the patio. The spacious bedroom features a walk-in closet, additional wall closet and a well-appointed en-suite bath with dual sinks, a soaking tub, separate shower, and private water closet. Outdoors, enjoy the screened private pool and spa with multiple seating areas and ample room to lounge and entertain in total comfort. The home has been immaculately maintained and includes new pool equipment and pool heater, a resurfaced pool, tile roof (2020), tankless gas water heater, as well as several additional upgrades – perfect move-in condition. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, with a community heated pool and spa just across the street. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, multiple beach volleyball courts and a pristine beach only minutes away. Perfectly located within the gates of the Resort at Longboat Key Club’s Harborside Golf course and 290 slip deep-water Moorings marina, and close to island dining—plus easy access to St. Armands Circle, Lido Beach, and downtown Sarasota—this golf course home delivers the space, privacy, and location that define Longboat Key at its best.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
548 GUNWALE LN, LONGBOAT KEY, FL 34228
$2,200,000114 Days on yellowkey MLS ID: A4680965
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 1967Monthly Fee: $17 Tax: $9,801 (2025)Community: Country Club Shores Sec 1Spa: YesSingle Family
Taxes:$9,801
Remarks: Country Club Shores - Completely renovated 3-bedroom, 2-bath canal-front home just three houses from the Bay. Updates include a new flat tile roof (2025), Carrier A/C and A.O. Smith water heater (2024), Pebble Tec pool and paver deck (2024), and newer seawall, dock, and 16,000 lb. boat lift (2.5 years). Enjoy Bay views from the 18 foot x 16 foot Trex dock with lighting and water, plus a 3 foot x 36 foot Trex dock with power and water. Interior features NuCORE waterproof flooring, plantation shutters, Silestone quartz countertops, and new Bosch and GE stainless appliances. The primary suite includes a walk-in closet with built-ins, dual sinks, whirlpool tub, and large shower. Split floor plan with guest bedrooms featuring walk-in closets; one includes a built-in office area. Move-in ready and ideally located for boaters seeking the best of Longboat Key waterfront living.
3488 MISTLETOE LN, LONGBOAT KEY, FL 34228
$3,675,000210 Days on yellowkey MLS ID: A4670010
REDUCED by $305,000 (7.7%) on 05/06/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3341 Built: 1989Monthly Fee: $1,083 Tax: $25,296 (2025)Community: Coreys LandingSpa: NoSingle Family
Taxes:$25,296
High School: Sarasota High
Remarks: Discover an exceptional opportunity to live behind the gates of the Longboat Key Club in the highly coveted Corey’s Landing neighborhood — one of the island’s premier bayfront addresses. Set within an intimate, established enclave there is a difference in this property vs. others in the neighborhood: it’s a free-standing residence which means you don’t share any common elements with an attached neighbor necessitating joint decisions on when to paint or replace a roof. There are only four free standing homes such as this, the rest are attached. This home welcomes you through double doors into a showplace of light, style, and space with immediate expansive bay views. Step outside to the expansive screened lanai — an inviting oasis for relaxing or entertaining by the pool while taking in mesmerizing bay views and the twinkling lights of downtown Sarasota. Enjoy immediate bay access with the private boat dock and lift. Inside, soaring transom windows, walls of glass, and rich wood floors enhance the open great-room design — a perfect setting for entertaining around the elegant fireplace. The updated kitchen connects seamlessly to the dining and living areas, showcasing sleek white cabinetry, a striking tile backsplash, solid-surface countertops, stainless steel appliances, and a generous breakfast bar ideal for casual gatherings. The first-floor primary suite is a private retreat with walls of glass, a cozy sitting area, custom built-ins, dual closets, and a luxurious remodeled bath featuring dual vanities, a large walk-in shower, and a separate water closet. Also on the main level are a private guest suite, second bedroom, full bathroom, a study/den, and a convenient outdoor dog space. Upstairs, a versatile loft provides the flexibility for a gym, library, or additional guest accommodations. The attached two-car garage offers ample storage, while Corey’s Landing residents enjoy access to a community pool, spa, Har-Tru tennis courts, and the private Bay Isles Beach Club. Ideally located near world-class shopping, dining, and the renowned St. Armands Circle, this residence captures the essence of the Longboat Key lifestyle — elegant, relaxed, and effortlessly connected to both land and sea.
Listing Agent: Kim Ogilvie (941-951-6660)
569 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$1,700,000215 Days on yellowkey MLS ID: A4669634
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2804 Built: 1996Monthly Fee: $3 Tax: $22,111 (2024)Community: Sleepy Lagoon ParkSpa: NoSingle Family
Taxes:$22,111
Remarks: $100,000 PRICE REDUCTION!!! Live the ultimate Florida Waterfront lifestyle in this private, calm, secure, spacious and elegant large elevated coastal home. Located on the North end of Longboat Key less than a mile to Anna Maria Island in the relaxed Sleepy Lagoon neighborhood with deeded beach access just around the corner, leading you to never crowded stretches of sand. The home is located on a boating canal just three houses in from the bay offering direct access to Sarasota Bay and the Intercoastal Waterway. This large ( 5328 SF total) very well maintained and upgraded elevated home offers 2800 SF on the main living level plus 2500 SF of bonus space on the first floor with an elevator. This elevated, well-built custom home sustained no damage nor have any flood claims ever been filed. This home spans two level of living and has an open floor plan, blending indoor and outdoor living. The main living area is upstairs with large flowing open rooms, vaulted ceilings, a fireplace and features French Doors leading to a screened Lanai overlooking the natural canal with foliage for privacy. The bedrooms are arranged in a split plan with each having en-suite bathrooms with lots of closets and built-ins. The large eat-in kitchen has custom cabinetry with crown molding, pull-outs, granite countertops and stainless appliances plus a large separate dining room perfect for all your family or friends. Just off the kitchen on the main living level is a very large laundry room along with all the closets in this home you will have all the storage you need. On the first level is the open foyer leading up to the living area with the elevator access and oversized split garages. There is an additional 2500 SF of AC/heated of interior space that is finished with polished concrete floors and walls of sliding doors leading to the pool area, porch, deck, yard and dock area. Also just outside your bonus space is private 60’ long screened, heated lap pool with a full bath. The property would provide great renal income also for a part time owner as it has in the past. Walk the beach, swim in the pool or ocean, ride your bike on the Longboat Key Bike path, fish, boat, kayak, paddle board, jet ski and enjoy your spacious home that is just a short drive to Sarasota, St. Armand’s circle and Anna Maria Island. Please see the videos. What are you waiting for? Start living the dream.
Listing Agent: Marta Altizer (941-383-7591)
3210 BAYOU SOUND, LONGBOAT KEY, FL 34228
$1,199,000316 Days on yellowkey MLS ID: A4658086
REDUCED by $100,000 (7.7%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2091 Built: 1978Monthly Fee: $104 Tax: $15,679 (2024)Community: The BayouSpa: NoSingle Family
Taxes:$15,679
Remarks: Motivated seller has a price improvement! This elevated retreat in the sought-after Bayou section of Bay Isles is ready for you! —A seamless blend of sophisticated design and relaxed coastal elegance. Encompassing nearly 2,100 sq. ft. of sunlit interiors, this residence offers an open-concept floor plan with soaring vaulted ceilings, creating an airy, inviting ambiance ideal for both everyday living and effortless entertaining. The expansive family room transitions beautifully into the contemporary eat-in kitchen, featuring clean, high-end finishes, abundant cabinetry, a large central island, and top-of-the-line stainless steel appliances that will delight. Thoughtful details such as graceful archways, ambient lighting, and tasteful materials add refined character throughout. Originally a 3-bedroom design, the home has been artfully reimagined to offer 2 bedrooms plus a dedicated office space—perfect for today’s flexible lifestyle. The oversized primary suite is a private sanctuary with a generous walk-in closet and a beautifully remodeled spa-like bath complete with double sinks and a fully tiled walk-in shower. The second bedroom is equally well-appointed, with direct access to an updated full bath. Sliders from both the kitchen and the primary suite open to the expansive screened upper-level deck with skylights—an ideal setting for al fresco dining, morning coffee, or sunset relaxation while overlooking the private lap pool, inviting patio, and meticulously refreshed landscaping. This residence offers true lock-and-leave convenience with a newer roof, advanced drainage system, updated landscaping, and low-maintenance, higher-end finishes that make it virtually maintenance-free. A rare 3-car garage provides ample space for vehicles and storage. Residents of Bay Isles enjoy access to the exclusive Bay Isles Beach Club, where sugar-white sands and the Gulf’s turquoise waters await. Enjoy proximity to the Longboat Key Club’s world-class golf, tennis, and pickleball facilities, as well as the LBK Marina. Daily conveniences—including Publix, the Caron Family Pavilion, and town services—are just moments away. A short drive brings you to the fine dining, boutique shopping, and cultural treasures of St. Armands Circle and downtown Sarasota, with Sarasota-Bradenton International Airport only 15 minutes away. This is Longboat Key luxury at its finest—simply move in, unpack, and embrace the effortless resort lifestyle you deserve.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Julie Lojacono Mackie (773-704-1438)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,790,000100 Days on yellowkey MLS ID: A4682565
REDUCED by $60,000 (2.1%) on 04/18/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Middle School: W.D. Sugg Middle
Remarks: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
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