5 Bedroom Homes For Sale In Siesta Key

5 Beds ⋅ 8 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Experience elevated coastal living in this exceptional 5-bedroom, 5.3-bath contemporary retreat, ideally located just steps from world-famous Siesta Public Beach and a short stroll to Siesta Village, where boutique shopping, dining, lively nightlife, and island charm await. Thoughtfully designed for effortless resort-style living, this four-level residence offers breathtaking Gulf views, expansive light-filled interiors, a private elevator, and extraordinary indoor and outdoor entertaining spaces. As the day draws to a close, the western sky transforms into a spectacular canvas of brilliant oranges, pinks, purples, and golds, creating unforgettable sunsets over the Gulf that can be enjoyed from multiple levels of the home, including the stunning rooftop retreat. The private outdoor oasis features a heated saltwater pool with sun shelf, spa, custom entertainment bar, lush tropical landscaping, and covered parking for up to four vehicles. Inside, the home showcases wide-plank wood-look porcelain flooring, painted tongue-and-groove ceilings, custom aluminum railings, and a dramatic four-story glass atrium staircase. The luxurious primary suite enjoys Gulf views, a private balcony, and a spa-inspired bath with a soaking tub, rain shower, dual vanities, and generous storage. Four additional ensuite guest bedrooms, each with private balconies and walk-in closets, provide exceptional comfort and privacy for family and guests. Designed for entertaining, the main living level features an open-concept great room with a custom fireplace, built-in dining, beverage bar, and a chef's kitchen appointed with custom cabinetry, granite countertops, GE Monogram appliances, a hidden coffee bar, oversized island, and banquet seating for ten. The adjoining Gulf-view terrace offers a fully equipped outdoor kitchen, creating the perfect setting for seamless indoor-outdoor living. Crowning the home is an extraordinary 950-square-foot rooftop terrace showcasing panoramic Gulf views and front-row seats to Siesta Key's legendary sunsets, where the ever-changing sky erupts in vibrant hues reflected across the Gulf waters. Complete with a full outdoor kitchen, beverage cooler, ice maker, automated louvered pergola, and powder bath, it is the ultimate venue for entertaining, enjoying sunset cocktails, or relaxing beneath the stars above the coastline. Additional highlights include a four-zone HVAC system, elevator service to every level including the rooftop, abundant secure storage, smart home prewiring with security cameras, low-maintenance tropical landscaping with irrigation and lighting, and superior concrete and masonry construction with a hollow-core concrete roof system and hurricane-rated impact glass, delivering exceptional durability, energy efficiency, and peace of mind. This is a rare opportunity to own a true luxury beach retreat that combines world-class construction, spectacular Gulf views, dramatic nightly sunsets painted across the Gulf sky, and an unbeatable location just steps from Siesta Beach and all the shopping, dining, and entertainment of Siesta Village.

5547 Avenida Del Mare, Sarasota

$5,690,000

5 Beds ⋅ 5 Baths ⋅ Archibald Resub SubDv. ⋅ 34242 Zip Code

Virtually Staged. Exquisite new construction on Siesta Key redefines island luxury! Substantial progress has already taken place to complete this masterpiece. This is a rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. Siesta Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its famous powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. Just moments from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity: your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock—a true island luxury! This thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate incredible craftsmanship and fine detail, the home offers 4,195 square feet of interior living space and an additional 3,756 square feet of outdoor living, seamlessly blending indoor and outdoor environments. The chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. Two beautifully appointed bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or the private elevator one level up to access the primary suite, featuring a truly custom bath with bespoke tile, designer finishes, a soaking tub, and a spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper level. Flexible, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any lifestyle, from multi-generational living to a dynamic entertainer’s paradise. Imagine a home where the luxuries of island beach life blend perfectly with a private, resort-style retreat. Step outside to your inground pool and spa for cooling off or casual lounging, head up to the rooftop deck for sunset cocktails and starlit conversation, or enjoy your private boating access just steps from your front door. When you are ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. This is more than a home; it is an invitation to own your piece of the new Siesta Key lifestyle—elevated, effortless, and extraordinary!

539 Avenida Del Norte, Sarasota

$7,675,000

5 Beds ⋅ 7 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code

Ready NOW. This exceptional waterfront estate by Dynan Construction, Sarasota's premier luxury builder, offers a rare opportunity to own a brand-new custom home without the wait. Renowned for impeccable craftsmanship, architectural integrity, and timeless coastal design, Dynan delivers a residence built to the Fortified Home Gold Standard, providing enhanced resilience against Florida's coastal elements while maintaining uncompromising luxury. Thoughtfully curated, every space reflects sophisticated design, elevated finishes, and enduring style. The gourmet kitchen is appointed with a premium Thermador appliance package, while Brizo plumbing fixtures are featured throughout the home, adding a refined level of quality and craftsmanship. This five bedroom single-story residence offers seven bathrooms - five full bathrooms, a dedicated pool bath, and an additional powder bath, creating a functional layout designed for both everyday living and effortless entertaining. Situated within the exclusive Hidden Harbor community—an intimate waterfront enclave known for its mature landscaping and lush, canopy-lined streets—the property enjoys a deep-water canal with direct access to Sarasota Bay and the Gulf of America. Designed to embrace Florida's indoor-outdoor lifestyle, expansive 10-foot sliding glass doors open to a resort-inspired outdoor living area complete with a custom pool and spa that is elevated to the finish floor of the home, covered pergola, and fully equipped outdoor kitchen. From sunrise cruises to sunset returns, enjoy the convenience of a private outdoor shower located just steps from the new dock and 10,000-pound boat lift. Every detail has been thoughtfully considered, from the seamless entertaining spaces to the carefully selected designer finishes throughout. Additional features include smart-home lighting controls, prewiring for security cameras and blinds, indoor/outdoor surround sound, and preparation for a future whole-house generator, providing convenience and peace of mind. Dual garage spaces—including a two-car garage and an additional one-car garage—offer the versatility to accommodate vehicles, water toys, bicycles, and storage with ease. Located just a short bike ride from the world-renowned Siesta Key Beach, this remarkable home combines luxury, durability, and an exceptional waterfront lifestyle with easy access to Sarasota's finest beaches, dining, shopping, and cultural attractions.

5215 Hidden Harbor Road, Sarasota

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 1142 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code

There is only one — Golden Set. Some residences embrace their surroundings. Others become an extension of them. Golden Set invites the island in—rich woods, woven textures, botanical motifs, and warm metallic accents establish a residence that feels both worldly and deeply rooted in Siesta Key. Your legacy, engineered for a lifetime of stories at a scale only you could imagine. This private resort centers around a breathtaking saltwater pool within its fully fenced backyard. Cross the sun shelf to the swim-up bar or unwind beneath the custom rock waterfall and built-in slide. Host championship matchups of pool volleyball or basketball, perfect your short game on the putting green, or dine alfresco beneath covered seating with multiple televisions and a state-of-the-art outdoor kitchen. Inside, nearly 3,600 square feet unfold across multiple levels connected by a private elevator. The great room serves as the social heart of the home – an exceptional setting for gatherings while the chef’s kitchen supports your culinary imagination. Festivities transition effortlessly from the expansive living and dining areas onto the terrace, blending the boundary between indoor elegance and outdoor paradise. The upper levels are devoted to privacy in four en-suite guest rooms and multiple viewing balconies. At the pinnacle of the residence lies its most exclusive destination. A well-appointed club room, complete with a half bath, creates an elevated entertainment hub, while the rooftop terrace, perched 50 feet above the island, is the final expression - sunrise over Siesta Key, long afternoons beneath the island sun, and evenings illuminated by the fading glow of the Gulf horizon. The secluded primary suite occupies the home's most private position, delivering breathtaking Gulf views, a spa-inspired bath, and the rare luxury of complete retreat. Here, your final view of the day is nothing short of spectacular. More than a home, Golden Set is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.

1142 Windsong Lane Unit B, Sarasota

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 1140 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code

There is only one — Siesta Springs. Some homes provide an escape. Others invite renewal. Inspired by the restorative rhythm of island living, Siesta Springs is a residence where every detail feels fresh, intentional, and connected to its surroundings. Driftwood-inspired finishes, layered coastal hues, and natural textures create a home that feels both contemporary and timeless—capturing the effortless spirit of Siesta Key without relying on convention. Designed to unfold naturally from one experience to the next, the residence balances vibrant gathering spaces with moments of quiet retreat. From private beach access and a lagoon-style pool to elevated terraces overlooking the Gulf, each level offers a new perspective while remaining connected to the whole. Across nearly 3,600 square feet and five levels connected by elevator access, the home encourages a lifestyle defined by movement, connection, and ease. The experience begins outdoors, where a resort-inspired backyard retreat features a cascading rock waterfall, custom slide, rope swing, sun shelf, ample covered patio seating with an outdoor kitchen, and lush landscaping. Here, recreation and relaxation exist in perfect balance. Inside, natural materials and modern finishes establish a sense of effortless sophistication. Driftwood-inspired flooring extends overhead, creating warmth and continuity throughout the residence, while shades of blue and gray evoke the colors of the shore beyond. A chef's kitchen supported by a dedicated scullery anchors the great room, where gatherings flow seamlessly onto expansive terraces and outdoor living spaces. Five en-suite bedrooms provide private retreats throughout the home, including a playful bunk room complete with a climbing wall—an unexpected detail that reinforces the home's spirit of energy and discovery. At the highest level, a club room designed for games, conversation, and connection opens to a rooftop terrace where sunrise and sunset become part of the daily rhythm. Nearby, the primary suite occupies the home's most private position, offering Gulf views, exceptional privacy, and a spa-inspired bath designed for restoration. More than a home, Siesta Springs is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.

1142 Windsong Lane Unit A, Sarasota

$6,990,000

5 Beds ⋅ 6 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code

Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.

4634 Higel Avenue, Sarasota

$4,490,000

5 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Currently under renovation. Welcome to an exceptional newly updated residence on he highly coveted Bay Island neighborhood on north Siesta Key, where timeless coastal architecture and modern luxury come together in one of Siesta Key’s most desirable locations. Situated on an expansive 0.48-acre homesite, this beautifully designed home offers 4,536 square feet of refined living space with a total of 5 bedrooms, 5 full bathrooms, and 1 half bath. Thoughtfully enhanced with new finishes, designer upgrades, and premium appliances throughout, the home also enjoys glimpses of the ocean water that complement its tranquil coastal setting. A private gated driveway leads to a detached 4-car garage, and guest suite with 2 bedrooms and 2 bathrooms, providing both privacy and convenience. At the center of the residence is a stunning chef’s kitchen designed for both everyday living and entertaining, complete with premium Sub-Zero refrigeration, professional-grade gas appliances, custom cabinetry, elegant stone surfaces, and a spacious center island. The adjoining great room and dining area seamlessly connect to the outdoor living spaces, while the luxurious primary suite provides a private retreat with a spa-inspired bathroom, generous walk-in closets, and peaceful views of the surrounding tropical landscape. Step outside to your own private coastal oasis, where a screened pool and expansive pool deck create the perfect setting for relaxation and entertaining year-round. Beautifully landscaped grounds and thoughtfully designed outdoor living areas enhance the home's resort-style atmosphere. Located just moments from Siesta Key’s world-renowned beaches, waterfront dining, boutique shopping, and Sarasota’s vibrant cultural amenities, this exceptional residence offers an unparalleled blend of privacy, sophistication, and convenience. A rare opportunity to own a luxury home on Norsota Way, where exceptional craftsmanship and the coveted island lifestyle come together. Photos and renderings may include virtual staging and virtual enhancements intended to illustrate the property's anticipated completion and design.

604 Norsota Way, Sarasota

$12,500,000

5 Beds ⋅ 7 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining. A scenic path leads to your private dock with a state-of-the-art electric system and space for a boat up to 37 feet, offering smooth access to the bay and Gulf. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.

546 Freeling Drive, Sarasota

$8,500,000

5 Beds ⋅ 5 Baths ⋅ Elliot M A Property Siesta Key SubDv. ⋅ 34242 Zip Code

A rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.

4034 Roberts Point Road, Sarasota

$2,895,000

5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code

There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

Sarasota

$2,895,000

5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code

There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

6910 Midnight Pass Road Unit B, Sarasota

$9,500,000

5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

Virtually Staged. Celebrated as one of SRQ Magazine’s “Home of the Year” in 2008 and born from the visionary imagination of acclaimed architect Mark Sultana and built by Voigt Construction, this extraordinary waterfront estate is not simply a home — it is a lifestyle. One of Siesta Key’s most iconic private residences, it stands as a living testament to the art of inspired modern design and the art of living beautifully. Deeply set on nearly one private acre along the tranquil Coconut Bayou, this gated 4-bedroom architectural masterpiece unfolds across multiple stories with absolute privacy, lush tropical splendor, and grounds generous enough for a pickleball court — all anchored by a fully separate guest house for family and friends who will never want to leave. From the moment the gates open, life here feels different. A breathtaking composition of glass, steel, and sculptural lines soars beneath dramatic ceilings, with natural light pouring through at every angle — whether that’s a lazy Sunday morning or a dinner party in full swing. Rise by private elevator or ascend the sweeping steel-and-glass staircase to the crown jewel of this residence: a 2,500 sq. ft. rooftop terrace, where the Siesta Key lifestyle reaches its absolute peak. Panoramic views sweep across Siesta Key, the downtown Sarasota skyline, and the shimmering waterways below — this is where memories are made. At the water’s edge, a brand-new dock on order, a double jet ski lift, and a dedicated kayak and paddleboard launch await — with direct, bridge-free access to the Intracoastal and the open Gulf beyond. This is the rare address that refuses to make you choose: the serenity of bayfront living, the thrill of open-water boating, and the privilege of private deeded beach access to the shores of Siesta Key — all from a single extraordinary estate. Designed with both beauty and resilience in mind, the residence sits impressively high and dry above the Bayou. Even through recent storms, the property remained untouched by flooding — including the pool area — offering a rare sense of peace of mind along Sarasota’s waterfront. The primary suite is a private world of its own — featuring a dedicated office/loft or exercise room, two custom walk-in closets, and a private balcony suspended above the Bayou. At the center of it all, an indulgent Champagne Jacuzzi infinity bathtub transforms every evening into a spa retreat. Downstairs, entertaining flows as naturally as conversation — from a dedicated movie theater room to tiered outdoor patios crowned by a spectacular summer kitchen, an open saltwater pool, and glowing fire bowl accents that keep the night alive. In the kitchen, Italian custom cabinetry, top-tier appliances, a service pantry, and a private wine cellar come together in a space as pleasurable to cook in as it is to gather around. Garage parking for five vehicles and separate guest quarters complete an offering with virtually nothing left to wish for. Minutes from The Out-of-Door Academy, Siesta Key Village, and Siesta Beach — this is not just an address. It is a life you’ll never want to leave.

4317 Midnight Pass Road, Sarasota

$1,200,000

5 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

This Charming Old 1948 Bungalow located just 3 Blocks behind Siesta Key Village and 4 Blocks to Siesta Key Beach!! It is quite the Interesting Property! It was converted into a Triplex many moons ago. It can easily be converted back to a single family residence. Currently, there are 2 Beds and 2 Baths downstairs and 2 Beds 1 Bath upstairs. There are 3 Kitchens, 3 Liv Areas 2 down, 1 up and there is a Bonus Rm down as well as a Screened in Patio on the front West side of the Home, an Open Patio on the East Side and a Closed in Upstairs. And, there's more... At the Rear of the Property is a Cottage, perfect for a Mother In Law Suite or Rental. It is a 1/1 with a full Kitchen and Liv Area. The grounds are Etherical, as there are private little Sitting Areas for each sector and in the center of the Backyard there is a Wash House for Laundry as well as an attached Storage Shed for Gardening. There are additional Outside Storage Units for each of the apartments, again, really a cool old school house with so much to offer. Make it back into a single family or keep it the way it is and rent the house and utilize the cottage for a personal vacay spot! Questions, call me!!

618 Avenida De Mayo, Sarasota

$4,485,000

5 Beds ⋅ 5 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code

Newly completed and move-in ready, this Coastal Contemporary waterfront residence on Siesta Key by award-winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft, and elevator—perfectly blending luxury, functionality, and coastal living. The main level features white oak wood floors, soaring beamed ceilings, and a bright open-concept layout designed for both everyday living and entertaining. The gourmet kitchen and expansive great room flow seamlessly through 10’ impact-resistant sliding glass doors to the outdoor living area, showcasing tranquil views of the pool and Grand Canal. A dedicated private office, a luxurious primary suite with a spa-inspired bath, and an additional ensuite guest bedroom complete the first floor. Upstairs, a spacious loft provides an ideal secondary gathering space. The VIP suite features a private balcony overlooking the water, while the fifth bedroom offers flexibility as a media room, fitness studio, or guest retreat. A custom wet bar enhances the upper level, creating the perfect setting for entertaining. Set along the scenic canals of Siesta Key, this property offers exceptional boating opportunities with easy access to open water—ideal for enjoying the best of Florida’s waterfront lifestyle right from your backyard. The outdoor living space is designed as a private retreat, complete with a sparkling pool, spa, and peaceful water views. Quick out to the expensive Intracoastal waterways for boaters. Florida living at its finest — sunset views, alfresco dining, and cozy evenings by the outdoor fireplace. A beautiful patio and grill setup that feels like a dream come true. Located just minutes from Siesta Key Beach, this home provides quick access to world-renowned beaches, dining, and the vibrant coastal lifestyle that makes Siesta Key one of the most desirable destinations in Florida. Exceptional opportunity to own a brand-new waterfront home with boating access in one of Sarasota’s premier locations.

558 Venice Lane, Sarasota

$1,800,000

5 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

A rare opportunity to own one of Siesta Key’s most versatile luxury properties. Situated on a rare oversized double lot within the city limits, this elevated coastal retreat offers exceptional privacy, flexibility, and proven income potential just minutes from Siesta Key Beach, Siesta Village, and the North Bridge. Completely reimagined with high-end finishes throughout, the home features nearly 3,000 square feet of thoughtfully designed living space, including 5 bedrooms, 3 bathrooms, an open-concept floor plan, designer kitchen, and spacious living areas that seamlessly blend indoor and outdoor living. Step outside to your own private backyard oasis featuring a sparkling pool, expansive patio, and multiple entertaining spaces designed for the ultimate Florida lifestyle. A detached guest suite overlooking the pool provides incredible flexibility for multigenerational living, extended guests, a private home office, or additional income-producing opportunities. Whether you’re searching for a primary residence, luxury vacation home, or investment property, this home delivers. Currently producing phenomenal rental returns, it offers a unique combination of luxury living and income potential that’s increasingly difficult to find on Siesta Key. With its elevated location, oversized lot, turnkey condition, exceptional outdoor living, and unmatched versatility, 3515 La Paloma is a rare opportunity to own a premier coastal retreat in one of Sarasota’s most desirable locations. Schedule your private showing today

3515 La Paloma Avenue, Sarasota

$2,200,000

5 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Price Reduced! Spacious island living, strong weekly rental income, and a prime north Siesta Key location come together in this beautifully maintained 5-bedroom, 3-bath furnished home just steps from beach access No. 1 at Shell Road on Big Pass. Built above base flood elevation of 11 feet, this property offers a valuable advantage on Siesta Key, along with the comfort, privacy, and usability today’s buyers are looking for. Fully gated and walled, the home sits on a generous lot surrounded by lush tropical landscaping, with an oversized 3-car garage and large paver driveway providing ample space for vehicles, beach gear, and a golf cart. Inside, the home offers large, open living spaces ideal for gathering and entertaining, featuring 12-foot ceilings, crown molding, arched openings, travertine flooring, and a spacious living room with gas fireplace. The kitchen includes stainless steel appliances, oak cabinetry, a breakfast nook overlooking the backyard oasis, and easy flow to the separate dining area and main living spaces. French doors open to a large terrace overlooking the tropical backyard, while an additional side terrace offers a private place to relax. The main-floor primary suite is a standout, offering direct terrace access, an oversized bedroom, two walk-in closets, and a luxurious en-suite bath with dual vanities, soaking tub, walk-in shower, and floor-to-ceiling travertine. Two additional bedrooms and a full bath are also located on the first floor, creating a functional and flexible layout. Upstairs, two generous guest bedrooms, a full bath, and a wet bar with beverage fridge provide an ideal retreat for visitors, with one bedroom opening to a private terrace overlooking the backyard. Designed for indoor-outdoor island living, the backyard is a true tropical oasis with mature landscaping, a heated saltwater pool with fountain, paver deck, large turf area, outdoor shower, and an exceptional tiki hut bar and outdoor kitchen complete with a built-in gas grill, two bar fridges, and porcelain countertops. An additional fenced side yard offers extra space for pets or outdoor enjoyment. Offered turn-key furnished, with a five-bedroom layout, generous lot size, multiple terraces, abundant storage, central vacuum, and expected 2026 rental income of $190,000. This home is an outstanding opportunity for those seeking a private Siesta Key retreat, income-producing investment, or both. Ideally located near world-renowned Siesta Key Beach and just a short drive to downtown Sarasota’s restaurants, shopping, and cultural attractions, this property offers the best of island living with convenience, comfort, and flexibility.

3508 La Paloma Avenue, Sarasota

$12,900,000

5 Beds ⋅ 7 Baths ⋅ Phillippi Shores SubDv. ⋅ 34242 Zip Code

Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house, and a separate waterfront cabana with bath. In total, the compound offers six bedrooms and six bathrooms, with gourmet kitchens in both the main house and guest house — each outfitted with high-end appliances throughout — ideal for multigenerational living, guest accommodations, or an exceptional private retreat. Throughout both residences, the finish detail is exceptional. Designer-selected materials create a cohesive and elevated aesthetic carried seamlessly across the entire compound. Custom wood flooring with intricate stone inlays, handcrafted stairwells featuring wood and stone risers, extensive crown molding, and refined architectural millwork highlight the level of craftsmanship invested in every space. Specialty stonework and thoughtfully curated finishes blend warmth with sophistication, creating interiors that feel timeless, substantial, and unmistakably high-end. Outdoor living is nothing short of spectacular. A dramatic infinity-edge pool with swim-assist system overlooks the water, enhanced by a striking waterfall feature that spills elegantly into the pool. New pool equipment (2025) supports the system. Natural rock waterfront frontage and a sculptural rock formation lead down to the shoreline, creating a one-of-a-kind coastal backdrop. Two docks serve the property — one with a double lift — offering outstanding boating access and rare protection on both sides of the point, with additional lift capacity for multiple watercraft. An outdoor shower provides added convenience after boating or swimming. Perched at the edge of the peninsula, the waterfront cabana and adjacent hot tub create a private, spa-like retreat suspended over the water — an unforgettable setting to take in sweeping sunset views. The residences were renovated separately: main house (2009) and guest house (2012). All A/C units have been renewed recently, along with the electric unit, and a new transformer (2024) services both properties. Sonos surround sound extends throughout all structures. Located on the highly desirable north end of Siesta Key, the estate offers convenient on-and-off island access while remaining just minutes from Southside Village and downtown Sarasota.

3750 Bayou Louise Lane, Sarasota

$1,200,000

5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!

618 Avenida De Mayo, Sarasota

$12,900,000

5 Beds ⋅ 6 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code

Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted. Photos 1 and 2 reflect the new colors that the home is being painted.

3440 Gulfmead Drive, Sarasota

$26,000,000

5 Beds ⋅ 7 Baths ⋅ Siesta Key SubDv. ⋅ 34242 Zip Code

Rising above an enviable stretch of shoreline, this Gulf-front estate showcases timeless architecture and coastal refinement. Designed by CMSA Architects and completed in 2020, the residence features layered rooflines, sculpted stone staircases, and soaring arched windows across more than 180 feet of Gulf frontage. With 10,600 square feet of interiors and 20,982 square feet in total, the home offers a grand yet effortless indoor–outdoor lifestyle, ideal for both elevated entertaining and daily living. A sweeping motor court, mature palms, and a grand double staircase create an immediate sense of arrival. Inside, natural light and uninterrupted Gulf vistas establish a feeling of calm, scale, and sophistication from sunrise to sunset. The great room, lined with floor-to-ceiling arched windows and anchored by a carved-stone fireplace, delivers both serenity and architectural presence. The main kitchen is a triumph of craftsmanship - featuring custom Campbell cabinetry, quartz countertops, designer lighting, Sub-Zero refrigeration, a Wolf six-burner dual-oven range, and a substantial island that anchors the open flow into the living and dining spaces. A prep kitchen and workspace elevate functionality with premium appliances, expansive storage, quartz counters, and a dedicated gift-wrapping wall. The bar and wine room create a refined entertaining destination, defined by custom cabinetry and designer lighting. An iron-and-glass–enclosed, temperature-controlled wine room serves as the focal point, complemented by adjacent illuminated display shelving. Sub-Zero refrigeration, an ice maker, and a Fisher & Paykel dishwasher drawer complete the space. Outdoors, the estate unfolds across three dramatic tiers of Gulf-facing living, featuring arched loggias and a resort-style alfresco kitchen with a wraparound bar that opens seamlessly to the main living spaces. An elevated infinity-edge pool and spa appear to merge with the Gulf, while thoughtfully designed outdoor areas transition effortlessly to a manicured lawn and direct access to the crystal-clear waters at Point of Rocks—where snorkeling, dolphin sightings, and sunset walks become part of daily life. The primary suite forms a private wing, introduced by an illuminated groin-vault corridor that enhances the home’s architectural rhythm. Gulf views fill the bedroom and its terrace, while the bath offers a symmetrically designed retreat with dual vanities, full-height mirrors, multiple chandeliers, a massive double-entry shower, a stone-surround soaking tub, a Sub-Zero–equipped coffee bar, and two exceptional custom closets. Nearby, the office provides a quiet, light-filled workspace. The upper level is devoted to comfort and privacy, offering four well-appointed guest suites, a spacious family room with a wet bar, multiple terraces capturing Gulf views, an additional office, and a laundry room. The ground level is enhanced by indoor–outdoor walkways connecting multiple spaces and generous storage, reinforcing the effortless, resort-style livability. A generator, 3-stop elevator, 6-plus humidity-controlled garage spaces, floor-to-ceiling shades, linear vents, whole-house automation, and shellstone and French oak flooring complete the offering. A short, shaded, tree-lined walk places you at Siesta Key Beach, the No. 1 beach in America by TripAdvisor, offering effortless access to one of the world’s most iconic shorelines.

7366 Point Of Rocks Road, Sarasota

5 Bedroom Homes For Sale In Siesta Key FL

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