Location: Longboat Key , 34228
Do Not Show Listings
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000212 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,314
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
380 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228
$1,150,000110 Days on yellowkey MLS ID: A4683391
REDUCED by $49,000 (4.1%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2380 Built: 1994 Tax: $11,342 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$11,342
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. 2BD+DEN! Positioned as the southern-most community on Longboat Keys’ Gulf of Mexico Drive is the stunning Tangerine Bay. Its presence of pristinely manicured tropical color admired by all that enter the Key. Within this gated community lies #515- horizontal to Sarasota’s bayfront experiencing views that span across blue waters abundant with active sea-life. This 2bd/Den/2.5bath/2-car private garage home, with excellent wall space for displaying your finest art collection, extends over 2,300 square feet of living space. Courtyard entry, equipped with gas hook-up for your own grill, offers slider access into the kitchen/ family room area which is perfect for a different entertaining perspective since the courtyard is large enough to also accommodate table and chairs. Of course, the coveted place to dwell will be the grand living/ dining area and balcony to experience morning sun over the calming waters or the miracle of all the hues the sky can offer as the sun begins to set behind you. Large primary en-suite enjoys the water view and slider access to the balcony, considerably sized walk-in closet and super-spacious bathroom to create the spa-like atmosphere of your dreams. #515 will not disappoint with the generous kitchen, kitchen water filtration, split floorplan, updated windows and doors, 2024 remote roll-down hurricane shutters, 2023 A/C, 2026 water heater, roof and sprinkler heads replaced approx. three years ago. With a spanning lap pool, meandering lush lounging areas, spa, fishing/day dock, tennis/ pickleball, fitness center and clubhouse- Tangerine Bay is poised for pleasure to all who get to call it home. For a small annual fee, owners can also become members of the Bay Isles Beach Club.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
550 YARDARM LN, LONGBOAT KEY, FL 34228
$3,775,000202 Days on yellowkey MLS ID: A4672604
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $20,000 (0.5%) on 04/28/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4281 Built: 2006Monthly Fee: $23 Tax: $16,615 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,615
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Motivated seller ….ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be instantly captivated by sparkling water views, soaring spaces, and the perfect blend of casual comfort and refined luxury. Designed for both relaxation and unforgettable entertaining, this 5-bedroom, 5.5-bath retreat is tailor-made for hosting family and friends in style. PRIME WATERFRONT LIVING - Private dock on a deep-water canal with no-bridge access to the bay, perfect for your weekend cruiser. LIGHT & BRIGHT OPEN LAYOUT - Walls of glass bring the outdoors in, filling the home with sunshine and stunning water views. ELEVATOR - Effortless access to main living levels from the three car garage. CHEF’S DREAM KITCHEN - High-end appliances, custom cabinetry, and an oversized island ready for gourmet meals and lively gatherings. LUXURIOUS SUITES - Owner’s retreat with a private balcony, spa-inspired bath, and dual walk-in closets. MOVIE ROOM - Your own private theater for cozy nights in. OUTDOOR OASIS - infinity pool, spacious patio, and lush landscaping for poolside lounging or sunset soirees. All this just steps to your DEEDED BEACH ACCESS and minutes from the world-class dining, shopping, and cultural treasures of St. Armands Circle and Downtown Sarasota. Whether you’re dreaming of a full-time Florida home or a seasonal escape, 550 Yardarm Lane delivers the ultimate Longboat Key lifestyle.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Melanie Russell (941-879-5882)
925 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,00047 Days on yellowkey MLS ID: A4691251
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1968 Tax: $491 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Taxes:$491
Middle School: W.D. Sugg Middle
Remarks: Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
948 SPANISH DR S, LONGBOAT KEY, FL 34228
$1,199,00091 Days on yellowkey MLS ID: A4685572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1399 Built: 1968 Tax: $4,945 (2025)Community: Spanish Main Yacht Club CondoVilla
Taxes:$4,945
Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000342 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
530 CHIPPING LN, LONGBOAT KEY, FL 34228
$5,799,00095 Days on yellowkey MLS ID: A4685275
Bed: 5 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4216 Built: 2026Monthly Fee: $21 Tax: $16,910 (2025)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,910
Remarks: Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,095,00079 Days on yellowkey MLS ID: A4686721
REDUCED by $130,000 (10.6%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3080 GRAND BAY BLVD #515, LONGBOAT KEY, FL 34228
$625,000159 Days on yellowkey MLS ID: A4674001
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1276 Built: 1996 Tax: $7,834 (2024)Community: Grand Bay 5Spa: YesCondo
Taxes:$7,834
Remarks: Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.
Listing Agent: Bruce Myer (941-376-5311)
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000229 Days on yellowkey MLS ID: A4669086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $7,875 (2024)Community: Beachplace IiiCondo
Taxes:$7,875
Remarks: One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: John Esser (515-306-8505)
1000 LONGBOAT CLUB RD #204, LONGBOAT KEY, FL 34228
$949,000208 Days on yellowkey MLS ID: A4671838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $6,901 (2024)Community: Privateer SouthCondo
Taxes:$6,901
Remarks: Sublime Gulfside Retreat at Privateer South — 1000 Longboat Club Rd #204 Experience the pinnacle of effortless beachfront living behind the prestigious gates of the Longboat Key Club. This immaculate, fully remodeled 2-bedroom/2-bath residence at Privateer South is offered turnkey furnished, presenting an immediate sanctuary of modern coastal style. Meticulously renovated with longevity in mind, the home is enveloped in impact-rated windows and sliders, ensuring quiet comfort, energy efficiency, and ultimate peace of mind. An inviting entry flows into a radiant, open-concept great room where living and dining zones transition seamlessly to the outdoors. Step onto your private covered balcony to take in unobstructed, panoramic views of the Gulf of Mexico— the ultimate backdrop for sunrise coffee, golden-hour cocktails, and the soothing sounds of the surf. Inside, cohesive coastal flooring and a sophisticated neutral palette provide an elegant canvas for personal style, accented by designer lighting and polished hardware. The renovated kitchen is a sleek culinary workspace featuring custom cabinetry, lustrous stone countertops, and premium stainless-steel appliances. The thoughtful split-bedroom layout guarantees privacy for owners and guests alike. The serene primary suite is a true retreat, offering extensive custom built-out wardrobes and a spa-inspired en-suite bath with a frameless walk-in shower. The oversized guest bedroom is equally impressive, boasting its own generous custom walk-in closet and adjacency to a second, well-appointed full bath. This residence is designed for a true "lock-and-leave" lifestyle, complete with abundant interior storage, an assigned covered parking space, and an additional dedicated storage locker. Privateer South provides an unrivaled resort experience on a pristine stretch of sugar-sand beach. Enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, a modern fitness center, a vibrant clubhouse, on-site management, and 24-hour gated security, all framed by lush tropical landscaping. Comprehensive association services handle practically everything, supporting a stress-free ownership experience. Minutes beyond the shoreline lie world-class amenities: championship golf, a full-service marina, and fine dining at the Longboat Key Club (membership optional), the chic boutiques of St. Armands Circle, and the cultural vibrancy of downtown Sarasota. A rare blend of thoughtful renovation, storm-ready construction, and amenity-rich Gulfside living, Privateer South #204 is more than a condo—it’s an endless getaway.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mike Griffin (941-586-6402)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500251 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Tax Year: 2023
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$4,000,00043 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
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
$6,750,00086 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
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)
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,00069 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.
3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,595,000232 Days on yellowkey MLS ID: A4667842
0 Days Off yellowkey (back on 4/28/2026)
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
$425,00044 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
$425,00044 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
501 NORTON ST, LONGBOAT KEY, FL 34228
$2,995,00098 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)
509 SPANISH DR N, LONGBOAT KEY, FL 34228
$369,00058 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 Agent: Garrett Sedlacek (913-461-6882)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.