Location: Longboat Key
Do Not Show Listings
2425 GULF OF MEXICO DR #2E, LONGBOAT KEY, FL 34228
$1,400,00029 Days on yellowkey MLS ID: A4691707
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $14,160 (2025)Community: Sea Gate ClubSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,160
Elementary School: Southside Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Amazing and Unobstructed 2nd Floor Gulf, Beach, and Pool Views! This is your perfect Direct beachfront condo, with floor to ceiling updated windows throughout! Nearly 1,500 sq. ft,. Tile floors in the main living areas, split bedroom floor plan, and amazing views from every room! Just move right in and enjoy, or bring your own creative ideas. The Sea Gate Club building has been completely remodeled! New roof, new windows, new railings, gorgeous new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities. Priced for a quick sale, hurry to come see this gorgeous condo in paradise today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$4,000,00029 Days on yellowkey MLS ID: A4691388
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3600 Built: 2027 Tax: $6,949 (2025)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$6,949
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, a premier luxury builder known for crafting high-end coastal residences with exceptional attention to detail and durability, this stunning new construction home at 592 Juan Anasco Dr offers an unparalleled blend of sophistication, comfort, and waterfront living. Perfectly positioned on a canal-front lot in Longboat Key, this 5-bedroom, 5.5-bath residence is thoughtfully designed to capture the essence of refined coastal living. Expansive windows, soaring ceilings, and a light-filled interior create an inviting atmosphere, while the home’s modern coastal aesthetic is complemented by carefully curated finishes and timeless design elements that elevate every space. The spacious and well-appointed floor plan offers a seamless balance of functionality and privacy, making it ideal for both everyday living and elevated entertaining. Generous living areas provide a welcoming environment for gathering, while the primary suite serves as a true retreat—offering a peaceful escape with a spa-like feel. Each additional bedroom is designed with comfort in mind, providing flexibility for guests, family, or extended stays. Step outside to your private waterfront oasis, where a resort-style setting invites relaxation and effortless entertaining. Whether hosting friends, enjoying quiet evenings by the water, or taking advantage of Florida’s year-round sunshine, this outdoor space is designed to be experienced. With direct canal access, boating enthusiasts will appreciate the ability to enjoy the Intracoastal lifestyle right from their backyard. Built to meet current FEMA guidelines and elevation requirements, this home offers enhanced protection, improved insurance efficiency, and long-term peace of mind—an essential advantage for waterfront properties. The elevated construction is thoughtfully designed to perform in coastal conditions while maintaining both functionality and architectural appeal. Living on Longboat Key means embracing a lifestyle that is both refined and relaxed. Known for its pristine Gulf beaches, world-class golf, and exclusive residential feel, the island offers a quieter, more private alternative to neighboring destinations. Residents enjoy convenient access to the renowned shops and restaurants of St. Armands Circle, the cultural attractions of downtown Sarasota, and nearby marinas, beach clubs, and nature preserves. From morning walks along the shoreline to sunset cruises and evenings of coastal dining, every day feels like a getaway. This is more than a home—it’s a lifestyle defined by waterfront elegance, modern construction standards, and one of Florida’s most sought-after coastal communities. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
415 L AMBIANCE DR #A701, LONGBOAT KEY, FL 34228
$6,750,00072 Days on yellowkey MLS ID: A4685660
3 Days Off yellowkey (back on 4/28/2026)
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3380 Built: 1992 Tax: $46,611 (2025)Community: L Ambiance 1Condo
Taxes:$46,611
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. This highly desirable southwest corner Royal floor plan, expertly renovated throughout by the high end construction firm Voigt Brothers, offers 180 degree panoramic views from the azure Gulf waters to Sarasota Bay and the downtown city skyline. Exiting the private elevator into the grand foyer leads to an expansive great room with new floor-to-ceiling impact sliders framing breathtaking azure water views. The chef’s kitchen was opened to enhance the Gulf and City views and equipped with top-of-the-line the SubZero, Wolf, and Cove appliances. Adjacent to the kitchen, the breakfast nook boasts big City views and also provides a breakfast/coffee station with refrigerated drawers and access to the southeast facing terrace. The great room combines the spacious dining room area with a 22’X 35’ living space, a built-in wet bar with ice maker and wine refrigeration, and access to the wraparound terrace. Owners are fully pampered in the luxurious primary suite offering two walk-in closets, dual water closets, multiple vanity stations, Hydrosystems soaking tub, separate shower with multiple shower heads and decorator features that must be seen in person. The primary bedroom showcases Gulf water views, access to the wraparound terrace and chic cove lighting. Both guest rooms are ensuite with walk-in closets - one offering southeast views of the Bay and City, the other with direct Gulf views. A versatile 9X16 bonus room can serve as an office, storage or extra bedroom. This unit comes with TWO side by side premium garage parking spaces, a wine locker and additional storage locker. The residences at L’Ambiance are free floating with no common walls between units for ultimate privacy. L’ Ambiance amenities include 24 hour concierge service, gated security, resort-style heated pool & spa, 2 private Har-Tru tennis courts, state-of-the-art fitness and club rooms, several guest suites for extended family use and an onsite resident manager. Located just minutes from St. Armands Circle with its shopping and dining attractions as well as the cultural hub of downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
545 SANCTUARY DR #B204, LONGBOAT KEY, FL 34228
$2,799,000216 Days on yellowkey MLS ID: A4667288
0 Days Off yellowkey (back on 4/28/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3115 Built: 1991 Tax: $19,659 (2025)Community: Sanctuary IiiSpa: YesCondo
Taxes:$19,659
Remarks: Under contract-accepting backup offers. Prepare to be wowed by the direct turquoise Gulf views from the oversized wraparound terrace, main living areas and primary bedroom. The chef’s kitchen is open to the main living area and offers state-of-the-art JennAir stainless steel appliances complete with built-in convection and steam ovens, oversized center island, wine refrigeration with storage and breakfast area. The massive primary suite showcases floor to ceiling windows with the same big Gulf views, access to the terrace, garden tub with separate shower and two walk-in closets. The main guest bedroom is ensuite with its own private terrace access and another walk-in closet. The 3rd bedroom is being used as a den with French doors opening to the living room, its own ensuite full bath with shower and dazzling Gulf views. Other bonus rooms include a laundry room located conveniently off the kitchen with sink, and an office nook with built-ins adjacent to the foyer. This residence comes with TWO under building parking spaces and a separate storage locker. Located behind the prestigious gates of The Longboat Key Club on the desirable South end of Longboat Key, owners will enjoy being minutes from the fine dining and shopping on St. Armands Circle in addition to the close proximity to Southwest Florida’s cultural hub of downtown Sarasota. At the Sanctuary, you will be part of 18 incredible beachfront acres with trails, an Olympic sized heated pool and spa, lighted tennis courts, a fitness center, onsite management, 24-hour manned security gate and a club house with planned activities. Become a member of the Longboat Key Club and partake in the superior golf courses, 6 private restaurants, spa and wellness center and other AAA four-diamond beach resort offerings. Roof replaced in 2023, Elevators modernized in 2022, and pool decking replaced in 2024. Building passed the Milestone Structural Integrity Inspection.
527 SUTTON PL, LONGBOAT KEY, FL 34228
$349,000138 Days on yellowkey MLS ID: A4677642
1 Days Off yellowkey (back on 4/28/2026)
REDUCED by $26,000 (6.9%) on 04/08/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1088 Built: 1972 Tax: $2,054 (2024)Community: Sutton PlaceCondo
Taxes:$2,054
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Live the Longboat Key lifestyle in this beautifully updated two-story, two-bedroom townhome, where more than $60,000 in upgrades and improvements create the perfect blend of comfort, style, and coastal charm . Features include a private deeded beach, 2 heated pools, garage, pet-friendly, a marina with boat slips, and outdoor entertaining space. Offered furnished and move-in ready. Every room reflects thoughtful, elegant design, from curated furnishings to refined color palettes. The first floor features beautiful tile flooring and numerous upgrades, including a stunning kitchen with quartz countertops and backsplash, custom cabinetry, a designer sink and faucet, Bathrooms have been tastefully updated with designer fixtures, and smart recessed lighting enhances the ambiance throughout the home. Spacious bedrooms offer ample closet space and excellent storage throughout. Upstairs, elegant dark engineered wood flooring complements the tiled bathroom, creating a warm and sophisticated retreat. The enclosed lanai provides versatile bonus space ideal for a home office or family room. Additional highlights include an A/C system with iWave-R ionization generator, washer and dryer in unit, a private garage with extra storage, an electric kayak lift with 2 tandem kayaks included. . A lovely, remodeled community room, BBQ, a private beach pavilion with parking and restrooms. Gulf to Bay access, walking distance to Bayfront Park with dog park and pickleball.
Listing Agent: Michael Yawitz (941-587-8091)
3070 GRAND BAY BLVD #632, LONGBOAT KEY, FL 34228
$699,000569 Days on yellowkey MLS ID: A4627468
REDUCED by $25,900 (3.6%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1276 Built: 1995 Tax: $7,802 (2024)Community: Grand Bay 6Spa: YesCondo
Taxes:$7,802
High School: Booker High
Remarks: Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace offering sunrise and sunset views. This particular condo has been tastefully updated with new variable speed HVAC with humidity control & Wi-Fi thermostat in 2024; new water heater & significantly updated kitchen in 2026; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer especially with the recently renewed transferable Home-Tech service contract! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.
Listing Agent: Richard Perlman (941-228-8580)
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,00055 Days on yellowkey MLS ID: A4688632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
909 SPANISH DR N, LONGBOAT KEY, FL 34228
$650,00076 Days on yellowkey MLS ID: A4684728
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1300 Built: 1969 Tax: $5,107 (2024)Community: Spanish Main Yacht ClubSpa: NoCondo
Taxes:$5,107
Remarks: One or more photo(s) has been virtually staged. This gorgeous two-bedroom, two-bath Spanish Main standalone villa is a must-see! The fully complete custom remodel has been beautifully and tastefully appointed with meticulous craftsmanship. So many upgrades. Starting with the neutral tile plank flooring that runs throughout the villa, providing a seamless flow from room to room. The kitchen is a chef's dream. All wood 42-inch cabinets complete the kitchen with tons of storage, slow-close drawers, under-counter sink. Friends and family will love the oversized kitchen with all your new appliances and served on the large quartz counter/island that will easily seat seven barstools. The open floor plan allows for easy social gatherings. The primary bedroom has an en-suite bath with a spacious shower with custom glass frameless shower doors. Double sinks are topped off with beautiful lighting. The walk-in closet provides plenty of storage and is complete with sensor lighting. New double heavy wood and glass doors separate the primary bedroom from the spacious lanai. The lanai is the place to sit and enjoy the view of the lush wetlands that provide privacy and a sense of tropical retreat in your backyard. The expansive lanai can be used as a flex room, such as a dining area, office, reading room, a third sleeping place or workout area. Roof new in 2019 plus all hurricane windows and doors. Go out the hurricane-grade sliders to see the view of the Bay waters and smell the sea air. The Bay view from the lanai and backyard is lovely and definitely an added bonus that adds even more beauty to your backyard paradise. Feel secure with motion sensor lights at back of the home. Electric blinds on the windows provide ease of privacy and light control. A retractable awning will allow you to enjoy your oversized brick paver patio without the warm Florida sun being an issue. Extra outdoor PVC storage room. This vibrant 55-plus community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, and lots of amenities, shuffleboards, swimming pool, private deeded beach access to the gorgeous Longboat Key beaches and warm Gulf waters. Fishing, boating, cycling and more. Close to St. Armands Circle and downtown Sarasota makes this location ideal for shopping, dining, theater, botanical gardens, airport and more. All 212 units in Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. New owners will receive any balance of insurance funds that are allotted to this villa. Call for details. All FEMA regulations completed, including inspections. Ready to enjoy your piece of paradise. Can be under 55 to purchase. With 1,300 square feet under air since lanai was closed in.
225 SANDS POINT RD #7205, LONGBOAT KEY, FL 34228
$699,000148 Days on yellowkey MLS ID: A4676041
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $7,183 (2025)Community: Inn On The Beach Ph IiiSpa: YesCondo
Taxes:$7,183
Remarks: This beautifully remodeled Junior Suite captures serene lagoon views while offering excellent income potential through the established hotel rental program. Hurricane-impact sliders frame the space and open to a private terrace with glass railing, allowing uninterrupted views across the tropical lagoon setting. Sold fully furnished, this residence is truly turnkey, blending personal enjoyment with resort-style investment appeal. Inside, soaring 10’ ceilings enhance the sense of space and comfort, complemented by faux wood tile floors, crown molding and warm wood accents with shiplap detailing that add texture and character. A quaint dining area features a rich wood accent wall, creating a cozy yet refined atmosphere. The kitchen is thoughtfully appointed with stone countertops, white cabinetry with glass panel accents, stainless steel appliances and a striking tile backsplash that adds visual interest without overpowering the space. The spa-inspired bath continues the elevated feel, finished with shiplap walls, dual vanities and a walk-in glass shower adorned with gorgeous tilework. Every detail has been considered to create a polished, welcoming retreat for guests and owners alike. As part of the hotel program, ownership includes access to the exclusive 410-acre Longboat Key Club. Enjoy 5 distinctive restaurants, 45 holes of championship golf, the renowned Tennis Gardens, spa and fitness facilities, a private white-sand beach with attentive service, and a full-service marina, all proudly recognized with the AAA Four-Diamond Award.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
225 SANDS POINT RD #6201, LONGBOAT KEY, FL 34228
$790,000148 Days on yellowkey MLS ID: A4676042
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $7,304 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$7,304
Remarks: Tropical elegance awaits in this thoughtfully updated Junior Suite, which pairs tranquil lagoon views with strong rental potential through the established hotel program. Impact-rated sliding glass doors lead to a private, open terrace with a glass railing, allowing the lush, tropical setting to remain the focal point while inviting the outdoors in. Inside, the residence feels airy and welcoming thanks to 10’ ceilings and a carefully curated blend of textures and finishes. Faux wood tile floors run throughout, complemented by crown molding and warm wall accents with shiplap detailing that add depth and character without overwhelming the space. The dining nook is intimate and inviting, enhanced by a rich wood feature wall that creates a relaxed, comfortable atmosphere for casual meals or evening unwinding. The kitchen is both stylish and efficient, featuring stone countertops, crisp white cabinetry with glass-panel details, stainless steel appliances and a patterned tile backsplash that brings subtle visual interest. The bathroom continues the elevated feel with a spa-inspired design, offering dual vanities, a walk-in glass shower with detailed tilework and natural textures that create a calming retreat after a day in the sun. Offered fully furnished and seamlessly integrated into the hotel rental program, this residence allows owners to enjoy flexibility while benefiting from resort-level operations. Ownership includes access to the exclusive 410-acre Longboat Key Club, with five acclaimed dining venues, 45 holes of championship golf, the award-winning Tennis Gardens, spa and fitness facilities, a private white-sand beach with attendant service, and a full-service marina. Recent property-wide updates to guest rooms, pool areas, dining spaces, and services further enhance the experience at this AAA Four-Diamond destination.
3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,595,000218 Days on yellowkey MLS ID: A4667842
REDUCED by $50,000 (1.9%) on 04/28/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4510 Built: 1992 Tax: $20,206 (2024)Community: Coreys LandingSpa: YesSingle Family
Taxes:$20,206
Remarks: Under contract-accepting backup offers. Elegant 5BR/5BA home in the gated community of Corey’s Landing within Bay Isles on Longboat Key. With over 4,500 sq ft, this spacious two-story residence offers open living areas, soaring ceilings, and refined design for both comfort and style. The light-filled great room with 22-ft ceilings opens to a gourmet kitchen with stone countertops, breakfast bar, and stainless-steel appliances. The main-level primary suite features pool access, dual vanities, soaking tub, and walk-in shower. A fifth bedroom or office, full bath, laundry room, and elevator complete the first floor. Upstairs includes three en-suite bedrooms, including a guest suite with private balcony and golf course and bay views. Outdoor living includes a screened lanai, heated pool and spa, and lush tropical landscaping. Updates include 2018 roof, new A/C (2023), tankless water heaters, and new pool/spa motors. Owners enjoy deeded beach access at the Bay Isles Beach Club plus community tennis, pool, spa, kayak launch, and 24-hour gated security. Close to the Longboat Key Club, offering world-class golf, tennis, marina facilities, dining, and a private Gulf-front beach experience, as well as the shops and restaurants of St. Armands Circle.
2600 HARBOURSIDE DR #B-08, LONGBOAT KEY, FL 34228
$425,00030 Days on yellowkey MLS ID: A4691499
Bed: Bath: 0.0 Monthly Fee: $574 Tax: $4,370 (2025)Community: Longboat Key MooringsDock-Rackominium
Taxes:$4,370
Remarks: A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 80 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
2600 HARBOURSIDE DR #B-06, LONGBOAT KEY, FL 34228
$425,00030 Days on yellowkey MLS ID: A4691498
Bed: Bath: 0.0 Built: 1985Monthly Fee: $574 Tax: $4,193 (2025)Community: Bay IslesDock-Rackominium
Taxes:$4,193
4440 EXETER DR #106, LONGBOAT KEY, FL 34228
$649,00089 Days on yellowkey MLS ID: D6146366
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $9,714 (2024)Community: Longboat HarbourCondo
Taxes:$9,714
Remarks: Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway. Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed to maximize both comfort and scenery. The bright kitchen offers a convenient pass-through to the dining area and living room, allowing you to stay connected with guests while preparing meals. The spacious living room is lined with windows facing the water, delivering breathtaking sunrise views each morning. Sliding glass doors from both bedrooms open to a tiled three-season lanai, complete with additional sliders that lead directly to the outdoors — perfect for embracing Florida’s coastal lifestyle. Both bathrooms feature elegant granite countertops for durability and easy maintenance. ?? Exceptional Community Amenities Include: Private Beach Club with Parking, Four heated pools, Tennis and pickel balls courts, Fitness center, Clubhouse, On-ste manager and boat docks. (Available on a first come basis for sail or power boats) Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this waterfront gem offers the perfect blend of luxury, comfort, and active coastal living.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Roger Richmond (941-456-6281)
4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228
$470,000173 Days on yellowkey MLS ID: A4674307
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $5,334 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$5,334
Remarks: Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation space, fitness center, sauna, pickleball and tennis courts, outdoor grilling and entertainment area, kayak and paddleboard launch with storage, billiards, poker room, woodworking shop, library and bike storage. This self-managed community has strong reserves, no special assessments and no water intrusion from the 2024 storm season. Ideally located near Bayfront Park and just minutes from Publix, Longboat Key Town Center and St. Armands Circle.
Listing Agent: Sharon Meier (407-927-5669)
501 NORTON ST, LONGBOAT KEY, FL 34228
$2,995,00084 Days on yellowkey MLS ID: A4683196
REDUCED by $255,000 (7.8%) on 04/22/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3042 Built: 1994 Tax: $25,276 (2025)Community: Sleepy Lagoon Park 2Spa: YesSingle Family
Taxes:$25,276
Remarks: PRICE IMPROVEMENT! In the tranquil north end of Longboat Key, where Gulf breezes drift through the palms and the pace slows to a whisper, this extraordinary beach retreat captures the essence of refined coastal living. Positioned on nearly half an acre of canal front property and encompassing over 3,000 square feet of interior living space (more than 6,000 square feet total), the residence sits just across from the ultra convenient public beach access. This unique residence offers the rare luxury of both boating and beachside lifestyles in one remarkable setting. Recently transformed through a stunning renovation and offered turnkey furnished, the five bedroom, three bath waterfront home showcases long, picturesque canal views and an effortless indoor outdoor flow. A NEW ROOF in 2023 and new impact windows were installed in 2022 provide peace of mind. Vaulted ceilings and light-filled spaces that feel both expansive and inviting. At the heart of the home, the chef’s kitchen blends timeless style with modern performance, featuring classic shaker cabinetry, gleaming white quartz countertops, high-end white Café appliances, and generous island seating ideal for gathering. The primary suite is a private sanctuary of nearly 700 square feet, complete with dual walk-in closets and a spa-inspired bath designed for indulgence, including a dramatic double soaking tub with jets, fireplace and TV, a Moen technology-enhanced shower, and electronic Woodbridge toilets that elevate daily living with comfort and innovation. Each of the guest bedrooms offer sizeable walk in closets. Step from the screened lanai off the living room down to a resort-caliber outdoor environment that rivals the finest destinations, where a heated pool and spa anchor the space alongside a putting green, waterfront fire pit, game area, and a beautifully pavered outdoor kitchen designed for effortless entertaining. For boating enthusiasts, the property is exceptionally equipped with a 10,000-pound boat lift and a second dock for added enjoyment. Substantial non-conforming enhanced storage beneath the home and a spacious three-car garage provide versatility without compromising luxury, making this a rare waterfront compound where mornings begin at the beach, afternoons unfold on the water, and evenings are spent poolside under the stars. Located a short distance to the Bridge Street Pier which offers ample dining, shopping and entertainment options, this residence truly is the ultimate beach getaway.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Keith Redding (941-894-4216)
1485 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
$1,395,000121 Days on yellowkey MLS ID: A4679674
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1569 Built: 1981 Tax: $11,880 (2025)Community: Players Club ISpa: YesCondo
Taxes:$11,880
Remarks: Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.
Listing Agent: Rinat Sikdar (941-993-9292)
4360 CHATHAM DR #305, LONGBOAT KEY, FL 34228
$338,900131 Days on yellowkey MLS ID: A4678390
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969 Tax: $4,654 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$4,654
Remarks: Waterfront living made easy! This furnished 1-bedroom, 1-bath condo is move-in ready and features beautiful tile flooring throughout, an updated kitchen, and an enclosed lanai perfect for relaxing. Just steps to the beach and loaded with amenities including four heated pools, private gated beach parking with pavilion and restrooms, beach chair storage, pickleball and tennis courts, and boat docks available for a minimal annual fee (up to 34’ boats). Enjoy a fitness center, billiards and card rooms, arts studio, and a banquet hall for social events. New roof already paid for. Priced to sell—don’t miss this affordable slice of waterfront paradise! ????
Listing Agent: Malihe Karimi (941-376-5099)
509 SPANISH DR N, LONGBOAT KEY, FL 34228
$369,00044 Days on yellowkey MLS ID: N6143864
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $6,955 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,955
Remarks: STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATED..........IMPACT WINDOWS..........COMMUNITY POOL...........Just **432 steps from the beach**, this is where coastal living stops being a dream and becomes your daily rhythm. Morning walks on soft sand, sunset returns under glowing skies, and the constant sense that the water is always just around the corner. **Fully renovated and never lived in**, this Longboat Key retreat feels brand new in every way — a clean, beach-inspired design with effortless flow and natural light throughout. Featuring **quartz countertops, impact windows, and a brand new water heater**, every detail has already been perfected so you can arrive and immediately exhale. Set within a **quiet waterfront community with deeded beach access**, life here feels unhurried and private, yet connected to everything that defines coastal luxury. From **boating access and a nearby pool** to the walkable, relaxed atmosphere residents cherish, it’s a setting designed for ease, not effort. With your own **covered parking and driveway**, and just minutes to **St. Armands Circle, Sarasota, and Anna Maria Island**, you’re positioned in one of the most desirable corridors on the Gulf. This is the rare combination buyers wait for — **newly finished, never occupied, and this close to the shoreline** — where every day feels like a quiet escape, and every return home reminds you why you chose it.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Garrett Sedlacek (913-461-6882)
3806 GULF OF MEXICO DR #C312, LONGBOAT KEY, FL 34228
$320,00038 Days on yellowkey MLS ID: A4690206
0 Days Off yellowkey (back on 4/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1970 Tax: $3,659 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,659
Remarks: LONGBOAT KEY 2-bedroom, 2-bathroom end-unit condo offering a coastal lifestyle with convenient access to both the Gulf of Mexico and Sarasota Bay. This third-floor corner unit is filled with natural light, turnkey furnished and offers added privacy with no unit above. Interior features include a welcoming foyer entry and a flexible second bedroom with a retractable partition and Murphy bed, ideal for guests or a multipurpose space. Tile flooring runs throughout for easy maintenance. The HVAC system was replaced in 2024. The building provides secure entry and an assigned covered carport. Beach Harbor Club is a waterfront community spanning approximately 5.3 acres on Longboat Key, consisting of 133 units and uniquely positioned between the Gulf of Mexico and Sarasota Bay. Residents enjoy deeded beach access with showers, umbrellas, and beach chairs, along with bayfront amenities including a seawall, fishing areas, and newly constructed boat slips. Community features include an oversized heated swimming pool, clubhouse, fitness center, shuffleboard courts, outdoor cooking and grilling areas, kayak launch and storage, guest parking, additional storage, and on-site management. This community supports an active coastal lifestyle with opportunities for boating, kayaking, fishing, and beachgoing. The property is located near Bayfront Park with tennis facilities and is convenient to nearby shopping and everyday essentials.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
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