5 Bedroom homes for sale & real estate in Longboat Key, FL

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
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 d

$3,995,000

5 beds5.5 baths4,281 sq ft

550 Yardarm Ln, Longboat Key, FL 34228

Owner's retreat • Waterfront luxury • Chef's dream kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon

$5,495,000

5 beds5.5 baths3,503 sq ft

7147 LA Lenaire Dr, Longboat Key, FL 34228

1.35 acre lot • Pool • Built 1990

NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
Under Construction. Poised along one of Longboat Key’s most coveted stretches, this new semi-custom estate by Mason Martin Builders delivers sophisticated coastal living with rare peace of mind. Each level is designed to capture sweeping Gulf views without the exposure of direct beachfront placement, creating a residence that feels both refined and protected. It is your private sanctuary by the sea. Currently under construction and scheduled for completion in 2026, this architectural showcase spans approximately 10,300 total square feet with 4,900 square feet under air. Mason Martin’s craftsmanship is evident throughout, with modern tropical lines, exotic landscaping, and refine

$5,299,000

5 beds5.5 baths4,826 sq ft

2944 Gulf OF Mexico Dr, Longboat Key, FL 34228

Private bar • Elevator • Butler's pantry

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit. From the moment you arrive through the circular drive, the home’s e

$11,995,000

5 beds6 baths6,959 sq ft

6001 Gulf OF Mexico Dr, Longboat Key, FL 34228

Natural gas heating • Private terrace • Primary bath remodel

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
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

$2,790,000

5 beds5 baths4,510 sq ft

3408 Fair Oaks Ln, Longboat Key, FL 34228

Gated community • Deeded beach access • Gourmet kitchen

Property at 6601 Gulfside Rd, Longboat Key, FL 34228, 5 beds, 3 baths

$5,000,000

5 beds3 baths3,492 sq ft

6601 Gulfside Rd, Longboat Key, FL 34228

Property at 670 Old Compass Rd, Longboat Key, FL 34228, 5 beds, 5.5 baths

$4,925,000

5 beds5.5 baths4,022 sq ft

670 Old Compass Rd, Longboat Key, FL 34228

Property at 6603 Gulfside Rd, Longboat Key, FL 34228, 5 beds, 5.5 baths

$15,000,000

5 beds5.5 baths4,925 sq ft

6603 Gulfside Rd, Longboat Key, FL 34228

Property at 630 DE Narvaez Dr, Longboat Key, FL 34228, 5 beds, 5.5 baths

$11,900,000

5 beds5.5 baths4,591 sq ft

630 DE Narvaez Dr, Longboat Key, FL 34228

Property at 5919 Gulf OF Mexico Dr, Longboat Key, FL 34228, 5 beds, 6 baths

$10,495,000

5 beds6 baths5,596 sq ft

5919 Gulf OF Mexico Dr, Longboat Key, FL 34228

Property at 2945 Pyrula Dr, Longboat Key, FL 34228, 5 beds, 5 baths

$3,295,000

5 beds5 baths3,815 sq ft

2945 Pyrula Dr, Longboat Key, FL 34228

Property at 597 Buttonwood Dr, Longboat Key, FL 34228, 5 beds, 6 baths

$4,199,000

5 beds6 baths4,176 sq ft

597 Buttonwood Dr, Longboat Key, FL 34228

Property at 5910 Gulf OF Mexico Dr, Longboat Key, FL 34228, 5 beds, 5 baths

$6,250,000

5 beds5 baths4,272 sq ft

5910 Gulf OF Mexico Dr, Longboat Key, FL 34228

Property at 501 Harbor Point Rd, Longboat Key, FL 34228, 5 beds, 5.5 baths

$8,500,000

5 beds5.5 baths6,125 sq ft

501 Harbor Point Rd, Longboat Key, FL 34228

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NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
Welcome to your ultimate waterfront retreat in Bradenton Beach. This extraordinary direct bayfront estate defines the very best in coastal luxury living. Spanning 3,005 sq. ft. , this stunning residence is masterfully designed for comfort, style, and effortless enjoyment, offering 7 spacious bedrooms and 7.5 beautifully appointed bathrooms—a rare opportunity ideal for multigenerational living or hosting guests in absolute comfort. Every detail has been thoughtfully curated, from the 3-car garage to the private elevator that offers seamless access to all levels of the home. Step inside to an expansive open-concept great room, where natural light and water views pour in through oversize

$4,995,000

5 beds5.5 baths3,005 sq ft

116 8th St S, Bradenton Beach, FL 34217

Private elevator • Chef's kitchen • Waterfront retreat

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
In a world where more is usually never enough……. 161 S. Polk Drive is MORE and JUST ENOUGH OF EVERYTHING YOUR DREAMS ARE MADE OF! Positioned waterfront between St. Armands Circle and Lido Beach, you can start your day walking just one block to put your toes in the sand and soak up the morning sun and then head straight to your favorite lunch spot on the circle. Upon returning home, take up lounging in the split-level, salt water pool and relax to the sounds of the water as it crests the infinity edge OR you can choose one of the many decks, from rooftop on down, canal to Gulf, to savor the sun, the breeze, the views and the peacefulness all around you. Once evening arrives,

$6,500,000

5 beds5 baths4,617 sq ft

161 S Polk Dr, Sarasota, FL 34236

Privately gated • Infinity edge • Open plan

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
New and Improved List Price! The Best of Florida Luxury Living Found Here! Situated directly on the Sarasota Bay with breathtaking views of downtown Sarasota and Longboat Key. You can find this exquisite gem behind the gates of the distinguished community of Tidy Island. Where champions were made - this iconic bayfront residence on Tidy Island was built by Hall of Fame tennis coach and IMG Academy founder Nick Bollettieri, and once served as the home of tennis legend Andre Agassi during his early training years. Blending luxury, privacy, and sports history, this extraordinary property combines two oversized condos into one grand 6,900+ sq ft estate. With soaring vaulted ceilings, pa

$2,390,000

5 beds5 baths6,900 sq ft

78 Tidy Island Blvd, Bradenton, FL 34210

Theater room • Spa • Private elevator

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
Discover incredible flexibility with this well-maintained duplex featuring two separate units, both currently vacant and ready for immediate tenant and/or owner occupancy. Whether you’re looking to generate rental income right away or explore future redevelopment potential, this property delivers outstanding possibilities. The layout includes a 3-bedroom, 1-bath unit and a 2-bedroom, 1-bath unit, each offering a 1-car carport with attached laundry and storage rooms for each unit for added convenience. A brand-new roof (April 2025) provides lasting peace of mind and reduces future maintenance costs. With a projected gross annual income of approximately $43,200 and an estimated net inco

$525,000

5 beds2 baths2,268 sq ft

904 66th Ave W, Bradenton, FL 34207

Brand new roof • Two separate units • Attached laundry

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
Welcome to this beautifully upgraded 5-bedroom, 3-bath home in the exclusive, gated community of Legends Bay. With over 3,000 sq. ft. of luxury living space and over $180,000 in upgrades - this home is truly move-in ready and designed for both comfort and entertaining. This home its High & Dry in Flood Zone X. Step inside to discover an open, light-filled floor plan enhanced by an upgraded lighting package with recessed lights, designer fixtures, and upper-cabinet illumination. The gourmet kitchen is a chef’s dream, featuring sleek Samsung black stainless appliances, a custom backsplash, and generous counter space — perfect for cooking and gathering alike. The fireplace su

$1,350,000

5 beds3 baths3,139 sq ft

6261 Champions Row St, Bradenton, FL 34210

Gated community • Gourmet kitchen • 0.33 acre lot

ABOUT THIS HOME
5 Bedroom Homes for Sale in Longboat Key, FL
Breathtaking Bayfront Estate on Bird Key | 5 Bedrooms | 5.5 Bathrooms | 5,176 SF | . 69 Acre | Experience the pinnacle of Sarasota Bayfront living in this breathtaking Bird Key estate, where timeless coastal elegance meets modern luxury. Perfectly positioned to capture sweeping bay views and unforgettable sunsets, this 5,176-square-foot residence and largest lot in Bird Key offers refined elegance, modern comfort and sophistication inside and out. A grand paver driveway welcomes you to the beautiful oversized glass doors through which you enter into an awe-inspiring open layout showcasing abundant brightness and natural light throughout, soaring tray ceilings complete with beautiful crow

$9,500,000

5 beds5.5 baths5,176 sq ft

101 Seagull Ln, Sarasota, FL 34236

Resort style pool • Private beach • Gourmet chef kitchen

Property at 3401 Avenida Madera Unit B, Bradenton, FL 34210, 5 beds, 3.5 baths

$599,500

5 beds3.5 baths3,402 sq ft

3401 Avenida Madera Unit B, Bradenton, FL 34210

Property at 149 Tyler Dr, Sarasota, FL 34236, 5 beds, 6 baths

$4,800,000

5 beds6 baths4,389 sq ft

149 Tyler Dr, Sarasota, FL 34236

Property at 6520 Clemson St, Bradenton, FL 34207, 5 beds, 3 baths

$520,000

5 beds3 baths2,176 sq ft

6520 Clemson St, Bradenton, FL 34207

Property at 7418 Westmoreland Dr, Sarasota, FL 34243, 5 beds, 4 baths

$3,749,000

5 beds4 baths3,502 sq ft

7418 Westmoreland Dr, Sarasota, FL 34243

Property at 388 S Shore Dr, Sarasota, FL 34234, 5 beds, 4.5 baths

$18,950,000

5 beds4.5 baths7,428 sq ft

388 S Shore Dr, Sarasota, FL 34234

Property at 5718 Title Row Dr, Bradenton, FL 34210, 5 beds, 4 baths

$1,550,000

5 beds4 baths3,654 sq ft

5718 Title Row Dr, Bradenton, FL 34210

Property at 1209 Westway Dr, Sarasota, FL 34236, 5 beds, 7 baths

$15,000,000

5 beds7 baths6,862 sq ft

1209 Westway Dr, Sarasota, FL 34236

Property at 303 Gulf Dr N, Bradenton Beach, FL 34217, 5 beds, 4 baths

$5,000,000

5 beds4 baths3,200 sq ft

303 Gulf Dr N, Bradenton Beach, FL 34217

Property at 139 S Washington Dr, Sarasota, FL 34236, 5 beds, 6.5 baths

$17,500,000

5 beds6.5 baths7,817 sq ft

139 S Washington Dr, Sarasota, FL 34236

Property at 310 Bryn Mawr Is, Bradenton, FL 34207, 5 beds, 3 baths

$1,495,000

5 beds3 baths2,500 sq ft

310 Bryn Mawr Is, Bradenton, FL 34207

Property at 112 11th St S, Bradenton Beach, FL 34217, 5 beds, 5.5 baths

$4,995,000

5 beds5.5 baths4,088 sq ft

112 11th St S, Bradenton Beach, FL 34217

Property at 309 Ringling Point Dr, Sarasota, FL 34234, 5 beds, 4 baths

$5,895,000

5 beds4 baths6,918 sq ft

309 Ringling Point Dr, Sarasota, FL 34234

Property at 1435 Westway Dr, Sarasota, FL 34236, 5 beds, 7 baths

$10,995,000

5 beds7 baths5,759 sq ft

1435 Westway Dr, Sarasota, FL 34236

Property at 290 N Washington Dr, Sarasota, FL 34236, 5 beds, 5 baths

$8,250,000

5 beds5 baths6,799 sq ft

290 N Washington Dr, Sarasota, FL 34236

Based on information submitted to the MLS GRID as of Sun Nov 30 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

5 Bedroom Homes for Sale in Longboat Key

There are currently 14 5 bedroom homes in Longboat Key. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Longboat Key stay on the market for 91 days. Popular neighborhoods include Longboat Key Club, The Terraces at Wild Oak Bay, Bay Shore Gardens, Longboat Harbour, and Longboat Shores. This map is refreshed with the newest listings in Longboat Key every 15 minutes.

In the past month, 39 homes have been sold in Longboat Key. In addition to houses in Longboat Key, there were also 233 condos, 5 townhouses, and 1 multi-family unit for sale in Longboat Key last month. Find your dream home in Longboat Key using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Longboat Key are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Longboat Key. Our Longboat Key real estate stats and trends will give you more information about home buying and selling trends in Longboat Key. If you're looking to sell your home in the Longboat Key area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Longboat Key with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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