Siesta Isles Real Estate, Homes, Condos for Sale in Siesta Key, FL - Ed Grabowski

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Virtually Staged. Live the ultimate island life in the highly sought-after waterfront community of Siesta Isles. Perfectly positioned just 0.8 miles from the public parking lot of world-famous Siesta Beach, you can easily stroll to the powdery white sands that make this area America's number one beach. Enjoy a short, breezy bike ride to the charming shops and incredible dining of Siesta Village, all without ever having to step foot on the main roads. This three-bedroom, two-and-a-half-bathroom single-family home presents an incredible opportunity to design your ideal coastal retreat. Serving as a true artist's blank canvas, the residence invites you to bring your creative vision and reimagine every room into a custom masterpiece. You will have piece of mind knowing the roof and AC are only 2 years old! The newer kitchen and updated appliances shine. The exterior boasts lush, mature landscaping with a gorgeous canopy of trees and gardens, providing a beautifully serene and shaded oasis for outdoor living. For boating enthusiasts, you are merely fifteen minutes by water to the spectacular Sarasota Bay, featuring direct Gulf access with just a single bridge. When you are ready for a change of pace, a quick fifteen-minute drive transports you to the vibrant heart of downtown Sarasota, rich with cultural and urban amenities. This is a one-of-a-kind opportunity to craft a dream home in an absolutely unbeatable location.

5451 Shadow Lawn Drive, Sarasota

$4,795,000

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

Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.

5572 Shadow Lawn Drive, Sarasota

$3,795,000

4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Tucked away near the end of a quiet cul-de-sac on an oversized, private waterfront lot in Siesta Isles with 109 feet of frontage on Siesta Key's Grand Canal, this exceptional 4,161-square-foot residence offers a rare combination of privacy, expansive living spaces, extensive upgrades, and breathtaking water views. Positioned at the canal's coveted "Big Bend," the home enjoys panoramic open-water vistas enhanced by neighboring county-owned green space, creating a lush natural backdrop and a remarkable sense of seclusion. Designed for both grand entertaining and everyday comfort, the light-filled floor plan features four bedrooms+bonus room, three full baths, multiple living areas, and rich wood flooring throughout. At the heart of the home is a gourmet chef's kitchen appointed with premium appliances, seamlessly connecting to an expansive great room where floor-to-ceiling glass frames stunning waterfront views. A separate entertaining bar features illuminated cabinetry, a wine refrigerator, sink, second Bosch dishwasher, and pass-through window to the lanai, making indoor-outdoor hosting effortless. The great room easily accommodates a dining table for ten while offering multiple gathering spaces to relax and enjoy the ever-changing waterfront scenery. The spacious primary suite serves as a private retreat, featuring a newly replaced waterfront deck and captivating water views from nearly every angle. Extensively upgraded with an emphasis on durability and peace of mind, the home features impact-rated windows and doors, recently replaced metal and flat roofs, two elevated HVAC systems, an elevated whole-house generator, mini-split air conditioning in the garage, two water heaters, extensive electrical upgrades, and all cast-iron sewer lines replaced with PVC. Outside, the resort-style living experience continues with expansive travertine patios, a heated saltwater pool and spa, multiple covered and open-air seating areas, and exceptional boating amenities including a new dock, 10,000-pound boat lift, and additional double jet ski/kayak lift. Professionally designed landscaping and architectural lighting enhance the home's tropical setting, creating a beautiful ambiance both day and night. With quick access to Roberts Bay and the Intracoastal Waterway, this property is perfectly suited for boating enthusiasts. Located just one mile from world-famous Siesta Key Beach and minutes from Sarasota's renowned dining, shopping, and cultural attractions, this extraordinary waterfront retreat offers the perfect blend of luxury, comfort, boating lifestyle, and privacy. This is truly A HOME FOR JOYFUL GATHERINGS!

813 Idlewild Way, Sarasota

$2,225,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Set on a beautiful street on Siesta Key near the world-renowned white quartz sands of Siesta Beach and the shops and dining of Siesta Key Village, this exceptional waterfront residence captures the essence of relaxed coastal living with deep boating water along the Grand Canal and direct access to Sarasota Bay and the Intracoastal Waterway. Beautifully landscaped on a nearly 14,000-square-foot homesite, the property welcomes with a circular paver drive, tile roof and timeless curb appeal. Thoughtfully above base flood elevation, the residence blends the beauty of waterfront living with the added comfort of elevated construction. Inside, volume ceilings and an open floor plan create a light-filled atmosphere designed for comfortable everyday living and effortless entertaining. Rich Le Château engineered wood flooring flows throughout the living spaces, complemented by refined finishes and thoughtfully selected details. The beautifully designed island kitchen is elegant and functional, featuring fine stone countertops, a gas cooktop, stainless steel appliances, custom cabinetry and a generous workspace for gathering and entertaining. The spacious floor plan offers three bedrooms, two-and-a-half baths, a private office, formal and casual living and dining areas, a split-bedroom layout and an interior laundry room. The primary suite is complemented by a spacious ensuite bath with dual vanities, a soaking tub and a separate walk-in shower, creating a private retreat within the home. Walls of glass open to an expansive 35-by-35-foot screened lanai with a freeform pool and spa overlooking the waterway, creating a seamless transition between indoor and outdoor living. A magnificent up-lit oak tree brings warmth and character to the backyard, enhancing the property’s tranquil setting. For boating enthusiasts, the Grand Canal provides easy access to Sarasota Bay and the Intracoastal Waterway with only one bridge to the bay and a mean tide clearance of approximately 13 to 14 feet. The seawall, dock and pilings for a future boat lift accommodating up to 14,000 pounds were all installed in 2020, creating an exceptional setting for enjoying life on the water. A rare opportunity to experience refined waterfront living in one of Siesta Key’s desirable locations.

819 Paradise Way, Sarasota

$1,100,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT hurricane-impact windows, multiple triple-panel sliding impact glass doors, and a 2019 tile roof. Step inside through beautifully etched, Florida-themed French doors into an open-concept floor plan filled with natural light streaming from the screened lanai. The spacious living and dining areas seamlessly connect to a chef-inspired kitchen, complete with an induction range, griddle, and premium finishes—perfect for entertaining. The home features wood-grain luxury vinyl flooring throughout and tastefully updated bathrooms. The private primary suite is situated on one side of the home and includes an attached office, offering a quiet retreat. Just beyond, you’ll find a generously sized laundry room with a brand-new stackable washer and dryer. The opposite side of the home hosts additional bedrooms and a guest bathroom, providing comfort and privacy for family or visitors. Outdoors, enjoy your own private oasis with a saltwater pool and a brand-new, state-of-the-art pump system. Located in the highly desirable Siesta Isles community, this property is ideally positioned for strong rental potential, offering opportunities for annual, monthly, or seasonal income. Enjoy the convenience of being just a 10-minute walk or 5-minute bike ride to Siesta Key Beach—without the need to access main roads. Move-in ready and perfectly situated, this exceptional home offers the ultimate in coastal living. Schedule your private showing today.

5569 Shadow Lawn Drive, Sarasota

$2,300,000

4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Short Sale. Partially complete. Interior is mostly complete and needs final punch-out completed and painting.

927 Contento Street, Sarasota

$933,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, world renown island of Siesta Key. Being offered Turnkey Finished negotiable, you are ready to move in and get to relaxing on this spacious lot of over a quarter acre of high and dry land. You will find yourself in a 3-bedroom, 2- bathroom ranch style home with an extra bonus room for friends and family. It has an attached one car garage with a nice extension for storage of bikes and beach items. A key part of this home is that it has an oversized portico in front of the home making it easy to unpack the car out of the rain and in the shade on beautiful Florida sunny days. This home comes with its own caged and heated pool overlooking the extremely private backyard that backs up to a park preserve so you will never have anyone built behind you. This tropical backyard is basically maintenance free with no grass to mow a very peaceful filtered Koi Pond. The property’s tropical landscaping is full of lighting and is watered by a well-fed irrigation system which also automatically fills the pond. It’s as easy as that! Inside the beautiful home you will find an open floor plan with premium tile floors and kitchen offering granite countertops and upgraded soft closing cabinets and drawers. This property has had the water and drainage pipes fully re-piped with PVC, has new A/C ducting, and an upgraded electrical box with a 200-watt service amp. The best part about this property is it is a short bike ride to the famous Siesta Village and .8 miles from the Public Parking Lot to Siesta Key Beach! You can get to both places without ever stepping a foot on the main roads. Schedule a showing today to the one-of-a-kind listing that you could call HOME!

5353 Shadow Lawn Drive, Sarasota

$1,575,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Discover an exceptional waterfront homesite in the quiet, highly sought-after Siesta Isles community. Tucked away on a peaceful cul-de-sac with no through traffic, this cleared property offers a tranquil setting just five minutes from world-renowned Siesta Key Beach. Boating enthusiasts will appreciate direct water access, featuring a brand-new private dock and 16,000-pound boat lift, with easy navigation to the Intracoastal Waterway and the Gulf of Mexico via a single bridge at Midnight Pass. A newly constructed 122-foot seawall (2026) adds both value and peace of mind. Spanning 14,741 square feet, this build-ready homesite has been recently cleared and is ideally positioned at a canal intersection, providing expansive open water views from the rear of the property. This is a rare opportunity to design and build a custom coastal retreat in a serene and prestigious setting. Custom home plans are available for this build-to-suit property to expedite making your dream home a reality. Ideally located near Sarasota’s renowned shopping, dining, and cultural attractions, this offering embodies the perfect blend of luxury, lifestyle, and long-term value. Build your dream home where beach, boating, and privacy come together.

822 Paradise Way, Sarasota

$1,750,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Under contract-accepting backup offers. This property checks all the boxes for a fabulous Siesta Key residence: Close to the beach, boat lift in the back, newly raised seawall, and a quiet cul-de-sac. This exceptional waterfront homesite sits in the heart of Siesta Key, one of Florida’s most sought-after coastal destinations. It offers a rare opportunity to build your custom dream home in a serene, prestigious setting where world-class beach access, effortless boating, and exceptional privacy come together perfectly. Nestled on a quiet, no-through-traffic cul-de-sac in the exclusive Siesta Isles enclave, the property enjoys a coveted island-within-an-island feel that delivers tranquility while remaining conveniently located. Just a 5-minute walk or drive away lies world-famous Siesta Key Beach with its renowned powdery quartz sand. Boating enthusiasts will love the direct deep-water access, complete with a private dock and a recently updated (2022) 10,000-pound boat lift. From here, you can cruise easily into the Intracoastal Waterway and the Gulf of Mexico, passing only one bridge at Midnight Pass. The lot features a substantially raised seawall recently elevated an additional 24 inches to an approximate elevation of 5-feet, which is significantly higher than most nearby seawalls. This provides enhanced protection and peace of mind for the new owner. Additional waterfront amenities include concrete steps, a spacious deck, and a convenient water access ladder. A capped freshwater irrigation well is also in place for easy landscaping maintenance. This build-ready property comes with submitted architectural plans for a stunning nearly 4,000 square foot 4-bedroom, 4-bath custom home featuring an impressive master suite, private elevator, and pool. Buyers can choose to use these existing plans and continue working with the current architect, or create something entirely their own. The generous lot offers approximately over 15,000 square feet (per architectural calculations), providing ample space for your vision. You’ll also enjoy convenient proximity to world-class shopping, dining, and cultural attractions in nearby Sarasota.This is a rare blend of luxury, lifestyle, and long-term value. Build your dream coastal retreat where every day feels like a vacation — in one of the most desirable waterfront locations on Siesta Key.

5448 Azure Way, Sarasota

$1,890,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

New low price and potential seller financing! Deep boating water on the Grand Canal and Siesta Key’s world-famous beaches just minutes away, experience the best of island living. This beautifully renovated three-bedroom, three-bath waterfront residence offers a peaceful island retreat with nearly 2,900 square feet of living space plus a private office, ideal for everyday living and entertaining. On a quiet cul-de-sac in the desirable Siesta Isles neighborhood, the property enjoys approximately 99 feet of canal frontage with deep boating water and convenient access to Sarasota Bay and the Gulf of Mexico via a single bridge. The dock, rebuilt in 2024, is ready for boating, paddleboarding, kayaking, fishing and enjoying Sarasota’s exceptional waterways. Recently completed renovations have transformed the home into a fresh, move-in-ready coastal residence. Bright and welcoming interiors feature new finishes and thoughtfully selected materials. The open living spaces are designed to capture the beauty of the waterfront setting, creating a natural flow for relaxed living and entertaining. The newly redesigned kitchen features classic shaker-style cabinetry, quartz countertops and new appliances, creating a functional and stylish centerpiece for the home. Impact-rated windows and doors, a newer roof (2024), and a freshly painted exterior provide beauty and peace of mind. The spacious primary suite enjoys tranquil canal views through French doors and includes a private sitting room, creating a comfortable retreat in the home. The large primary bath provides generous space and is designed for relaxation and convenience. Outdoor living is equally inviting. The expansive pool terrace with oversized pool and spa overlooks the canal, offering a private setting for relaxing or gathering with friends and family. Begin your day with coffee on the pool deck while enjoying brilliant sunrises and end the evening with Siesta Key’s vibrant sunsets just minutes away at nearby Siesta Beach. Ideally near Siesta Key’s renowned quartz-sand beaches, the boutiques and dining of Siesta Village, and cultural amenities of downtown Sarasota, including the Ringling Museum and Marie Selby Botanical Gardens, this location combines island tranquility with convenient access to the area’s best attractions. Offering the rare combination of a beautifully renovated waterfront home, deep boating water, and a peaceful Siesta Key setting, this exceptional property captures the essence of Sarasota’s island lifestyle. Possible seller financing for qualified buyers.

951 Contento St., Siesta Key

$1,945,000

4 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is the expansive Florida room, a light-filled living space designed for year-round comfort with floor-to-ceiling windows and seamless views of the water and surrounding greenery—ideal for relaxing or entertaining. The home has been thoughtfully maintained and is in excellent condition, allowing for immediate occupancy or rental income potential. Additional highlights include a heated pool, open and functional layout, and spacious living areas. Located just minutes from Siesta Key Beach and Siesta Key Village, this property combines prime location, generous living space, and waterfront charm, making it ideal as a primary residence, vacation home, or investment property. The house did not get flooded from the recent 2024 storms, a new roof was replaced in 2024, A/C was replaced in 2023, a pool heat pump was installed in 2023, re-piped and remodeled in 2022.

814 Paradise Way, Sarasota

$1,599,999

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***

5507 Contento Drive, Sarasota

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

New price! Beautifully remodeled and ideally just minutes from world-renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort, and storm-ready peace of mind. Designed for effortless coastal living, the open main living area is highlighted by a vaulted ceiling, transom windows, and abundant natural light, with French doors opening seamlessly to the private outdoor entertaining space. Porcelain flooring flows throughout the home, complemented by solid wood cabinetry, quartz countertops, and a thoughtfully designed kitchen featuring KitchenAid appliances, an electric range with exhaust hood, and clean, timeless finishes. The interior is further enhanced by solid wood interior doors, custom lighting, and new Minka ceiling fans, creating a polished yet inviting atmosphere. Significant recent upgrades add substantial value and confidence for today’s buyers, including hurricane-impact windows, a new impact front door and rear French doors (2024), a new HVAC system (2024), a shingle roof (2021), and a hurricane-rated garage door. The primary suite features a custom closet system and a separate owner’s closet, ideal for part-time use or rental flexibility. Outdoors, enjoy a resort-style heated saltwater pool and spa, enhanced by a new pool heater (2025) and pool filter (2024), surrounded by mature tropical vegetation that provides exceptional privacy. Manicured front landscaping with lush plantings, an irrigation system, a paver driveway, and a Trex front walkway complete the home’s inviting curb appeal. Additional features include epoxy-finished garage floors and a Ring doorbell with exterior security cameras. Adjacent to Glebe Park and close to Siesta Key Village, this residence offers easy access to dining, shopping, entertainment, and the beach. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Equally suited as a full-time residence, seasonal retreat or potential income-producing investment, this home delivers refined island living in one of Siesta Key’s desirable neighborhoods.

1002 Glebe Lane, Sarasota

$995,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits. A prime 12,229-square-foot property in sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream home in one of Sarasota’s desirable beach neighborhoods. Offering a clean slate for visionary design to renovate or build new. The generous size of the property and ideal location make it ideally suited for a luxury custom home with room for a pool, tropical landscaping and seamless indoor-outdoor living. Enjoy beach access just .2 miles away, or go less than a mile to Siesta Village, where eclectic shops, lively dining and local entertainment await. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Unlock the potential to create a one-of-a-kind island residence just moments from world-renowned Siesta Beach.

734 Canal Road, Sarasota

$1,650,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Big price reduction, owner will entertain all serious offers!! Build your dream home on this stunning deep Waterfront cleared 15000 sqft lot on Siesta Keys Grand Canal. 10,000 lbs boat lift already in place and room for a second boat or water toys. Located on a quiet cul-de-sac, 154 feet of water frontage with wide views and direct access to the bay and Gulf of Mexico, just two-and-a-half blocks to the powdery white sands of Siesta Key Beach, walking distance to Siesta Village's quaint shops and restaurants and approximately 15 minutes to downtown Sarasota many restaurants, shopping, cultural events and entertainment Well on premises for irrigation.

5353 Cape Leyte Drive, Sarasota

$1,650,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Set along the Grand Canal in Siesta Isles, this inviting waterfront pool home offers an effortless blend of space, comfort and classic island living. Thoughtfully designed on a single level, the approximately 2,477-square-foot residence features a desirable three-way split floor plan with three private bedroom suites, three baths, a dedicated office or den, utility room and a two-car garage. Handsome double-entry doors open to a light-filled interior with high-volume ceilings and an easy, open flow, ideal for everyday living and entertaining. The great room connects seamlessly to the kitchen and breakfast area, all of which are positioned to capture long, tranquil canal views. A separate dining room with built-in cabinetry adds flexibility for hosting, while the kitchen is well-appointed with wood cabinetry, stone countertops, stainless steel appliances and a breakfast bar. French doors extend the living space outdoors to a large, screened paver lanai with covered seating, a pool and expansive water views, creating an indoor-outdoor lifestyle. A newer seawall, private dock with a kayak lift and a separate boat lift provide quick access to Sarasota Bay, the Intracoastal Waterway and the Gulf of Mexico, with open water within approximately 15 minutes. Ideally just minutes from Siesta Key’s world-famous quartz sand beaches, the shops and restaurants of Siesta Village, and cultural offerings of downtown Sarasota, this home delivers the best of waterfront living in one of the island’s sought-after neighborhoods. Whether as a full-time residence or a coastal retreat, this Siesta Isles property offers the lifestyle, location and boating access that define life on the water.

5348 Shadow Lawn Drive, Sarasota

$4,490,000

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

Experience elevated coastal living in this award-winning “Marlin Model” by Nutter Custom Construction, perfectly positioned on Siesta Key’s coveted Grand Canal. Completed in 2023 and showcased as the builder’s signature home, this completely custom Yacht-Modern residence blends refined elegance, contemporary design, and exceptional waterfront functionality. With 4,294 sq. ft. under air and 6,405 total sq. ft., this home offers 3 ensuite bedrooms (please note gym can be converted into 4th bedroom), 3 full baths, 2 half baths—including a dedicated pool bath—plus multiple flexible indoor and outdoor living spaces ideal for relaxed luxury and entertaining. Floor-to-ceiling glass doors reveal sweeping water views and seamless indoor-outdoor flow. Elevated construction and smart-home technology offer modern security and peace of mind. No water intrusion or damage during recent hurricanes. The chef’s kitchen is a standout, featuring a 10-ft waterfall island, European white dolomite counters, hidden walk-in pantry, Wolf appliances, built-in coffee system, under-cabinet toe lighting, and formal dining with wine cooler and ice maker. The primary suite is a private retreat with dual walk-in closets, hidden entry doors, freestanding soaking tub, oversized designer shower and steam room, and private outdoor shower garden. Outside, enjoy resort-style living with a multi-level pool and raised spa with infinity spillover, expansive lounging deck, covered living and dining with motorized screens, full outdoor kitchen, turf backyard with putting green, and multiple terraces. For boating enthusiasts, the property offers 104 ft of waterfront, a new concrete seawall, 104 ft of composite dock, two Golden Gear boat lifts with remotes (20,000lb & 5,000lb), water and shore power. Hop on your boat and be in the Gulf in less than 15 minutes. This property has received prestigious recognition, earning Best Custom Home, Best Kitchen, and Best Staircase in the Parade of Homes awards — reflecting exceptional craftsmanship and design distinction. The oversized 2.5-car garage provides excellent storage and functionality, offering space for a golf cart or the option to create a golf simulator setup. Located in Siesta Isles with a voluntary HOA, less than one mile to Siesta Key Beach and moments to Siesta Village by golf cart or bike. Click on the Virtual Tour Link to get a behind the scenes look! ** Furniture negotiable

5362 Shadow Lawn Drive, Sarasota

$1,400,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

JUST REDUCED!! SIESTA ISLES Waterfront Gem. Experience the best of Siesta Key living in this well maintained 3-bedroom + den, 3-bath pool home with 135+ feet of frontage on the Grand Canal. Situated on an oversized 15,269 sq ft /.35-acre lot, this residence offers the perfect blend of privacy, upgrades, and waterfront lifestyle. Situated well back from the street, the home opens with a welcoming foyer and expansive great room featuring vaulted ceilings, impact windows and impact sliding glass doors flooding the space with natural light while framing serene garden and waterway views. Two bedrooms feature en-suite baths and direct access to the back yard, while the primary suite’s bath connects conveniently to the pool area. Enjoy the privacy of this tropical retreat, swim in the sparkling pool, rinse off in the outdoor shower, or launch kayaks and paddleboards from the floating dock. With space to add a full dock or lift, boaters will love the water access via one fixed bridge to the Intracoastal Waterway. Practical updates bring peace of mind, including a durable metal roof and maintenance contracts for irrigation, AC, pest control, and alarm systems. The home has county water and sewer and there's a shared irrigation well that sustains the mature landscaping. The home experienced NO WATER INTRUSTION during last year’s storms and is truly move-in ready. A winding walkway through lush landscaping leads to the waterfront patio, while an extended brick paver driveway offers ample guest parking. Just minutes from Siesta Key’s world-famous beaches and The Village’s varied dining and shopping options, this home is ideal as a full-time residence or lucrative rental investment. Don’t miss your chance to own a slice of paradise on the Grand Canal—schedule your private showing today!

5215 Cape Leyte Drive, Sarasota

$700,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location. Enjoy the best of Siesta Key living—just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the dining and shopping of Siesta Village. Despite its proximity to these sought-after amenities, the property feels peaceful and secluded, tucked away on a quiet street removed from the island’s main thoroughfares. With nearly 100 feet of street frontage and a depth of 120 feet, the lot offers a generous and flexible building footprint. Whether you envision a sleek, modern coastal retreat or a charming, classic island cottage, this is a rare opportunity to create your ideal Siesta Key home in one of its most desirable neighborhoods.

5587 Shadow Lawn Drive, Sarasota

$1,700,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Designer waterfront retreat on Siesta Key. Welcome to your dream coastal getaway! Tucked away on a quiet cul-de-sac, just moments from the world-renowned, powdery quartz sands of Siesta Beach, this impeccably renovated and landscaped waterfront home captures the essence of laid-back luxury and island living. Boaters will delight in the deepwater Grand Canal access—just one fixed bridge to Sarasota Bay and the Intracoastal Waterway, with direct Gulf of Mexico access. This fabulous single-level, three-bedroom, two-bath residence offers an open and airy floor plan filled with natural light, making it ideal for both full-time residence and an exceptional vacation retreat. A stunning 2023 designer renovation has infused the home with texture, warmth, and playful sophistication. From natural materials and artistic wallpaper to colorful accents and layered finishes, every detail is thoughtfully curated. Upgrades include new flooring, kitchen, bathrooms, plumbing, lighting, electrical systems, and front and garage doors. Enter through the statement front door into a welcoming foyer that opens to the expansive living room, featuring sleek, floating built-ins. The heart of the home is the striking kitchen and dining space, featuring a custom terrazzo island, quartz counters, Wolf and Miele appliances, and handcrafted cabinetry that offers generous storage. The island’s induction cooktop, drop-down exhaust fan, and bar seating blend form and function beautifully. A dedicated bar area with a wine cooler enhances the entertaining experience. The wide plank engineered oak flooring flows throughout, uniting each space with warmth and elegance. The spacious waterfront primary suite is a serene escape, complete with a spa-inspired bath, dual sinks, and a walk-in shower with private access to the pool. A thoughtful split floor plan provides privacy for two guest bedrooms and a second full bath. Even the laundry room is a showpiece, featuring art tile, a stacked washer and dryer, a beverage cooler, and whimsical details. Additional features include remote-controlled blinds, reverse osmosis in the kitchen, impact glass doors, windows, and garage door, an air-conditioned two-car garage with a paver driveway and walkways, Leaf Guard gutters, a 2023 HVAC system, 2023 attic and exterior insulation, and a 2020 roof. Seamless indoor-outdoor living begins with sliding impact glass doors that lead to the covered lanai and an oversized paver deck. Enjoy alfresco dining by the heated saltwater pool, resurfaced and retiled in 2022 with a sun shelf and spa also added for lounging. The lush, tropically landscaped backyard is fully fenced with faux turf, a putting green, and a fenced dog run, making it ideal for relaxation or play. Boating and water activities are a breeze from your private dock with a 14,000-pound remote-controlled lift, kayak launch, and seawall (2022). Just 15 minutes to open water, you'll savor days of fishing, paddleboarding, and Gulf cruising—right from your backyard. Ideally located near Siesta Village’s charming shops and restaurants, yet just minutes from mainland amenities, top-rated schools, and vibrant downtown Sarasota. Grab your flip-flops and sunscreen; this one-of-a-kind home offers the complete island lifestyle.

1031 Contento Street, Sarasota

$900,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

OWNER IS MOTIVATED! PLEASE BRING A REASONABLE OFFER. WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. LOT, has a private dock and features 102 FEET OF FRONTAGE ON THE GRAND CANAL. Only one fixed bridge at Midnight Pass Rd means GREAT BOATING ACCESS to Sarasota Bay and the Gulf. Or take a short bike ride or walk to SIESTA BEACH, the #1 beach in the US. This spacious home has over 2,000 Sq. Ft. of living area. It had minor flooding during Hurricane Helene. The water and carpet were quickly removed. Removal of the carpet revealed Terrazzo Floors in the main part of the house. THE PRIME WATERFRONT LOCATION CLOSE TO THE BEACH makes this property an excellent candidate to use as your MID-CENTURY STYLE beach retreat, or to BUILD YOUR DREAM HOME. The existing home has a split bedroom plan that wraps around the LARGE SCREENED LANAI. Pocketing sliding doors lead to the spacious lanai from four rooms. From there, you will enjoy privacy, nice water views and quick access to your boat at YOUR PRIVATE DOCK. All three bedrooms are a good size. The Family Room is off the kitchen. This spacious room has its own mini split AC system and great storage space. The Inside Laundry Room has convenient built-ins and a small workshop area. An exterior door leads to the private outdoor shower. Very handy when you come back from the beach or boating. Small storage shed in back. In addition to the unbeatable beach and boating, this excellent Mid-Key location offers convenient access to the shops and restaurants of Siesta Village. Downtown Sarasota is a short drive away where you can enjoy various Theaters, Art Galleries, The Farmer's Market and fine dining. Motivated owner has made this the LOWEST PRICED WATERFRONT HOME IN SIESTA ISLES!

5572 Shadow Lawn Drive, Sarasota

$640,000

2 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Discover a rare opportunity to own a piece of Siesta Key history with this early Ruth Richmond designed single family home, ideally situated on a spacious high and dry 12,000 sq ft lot surrounded by sea grape and mature oaks. The two bedroom two bath fixer upper includes a studio with full bath and separate entrance - perfect for guests or rental income. Inside, enjoy a wood burning fireplace and large sliding glass doors which open to a large patio and a beautiful free form swimming pool. Kitchen is piped for gas stove. While the home needs work and has not been updated, the A/C is brand new. The home offers incredible potential to restore or reimagine. Step outside to your private swimming pool and enjoy the serenity of a 75 foot rear barrier that backs up to Glebe Park, ensuring both privacy and natural beauty. This property did not flood in the hurricanes. Location, character, and potential - this is your chance to create your dream retreat in one of Siesta Key's most sought-after neighborhoods.

5369 Shadow Lawn Drive, Sarasota

$700,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Siesta Key Beach Retreat – Now $829,000 Welcome to 5223 Shadow Lawn Dr, a 3-bedroom, 2-bath home in coveted Siesta Isles, just 1 mile from the sugar sands of Siesta Key Beach. Located on a quiet cul-de-sac with preserve views and mature palms, this 1,459 sq. ft. property blends lifestyle, privacy, and investment potential. Inside, you'll find a bright open layout, modern laminate flooring, neutral finishes, and a renovated kitchen with granite countertops, stainless steel appliances, and crisp light cabinetry. The living area opens to a spacious screened lanai with a fully restored pool (completed October 2025)—now crystal clear and ready to enjoy. The primary suite features an updated en-suite bath, while two additional bedrooms and a second bath provide flexibility for guests, family, or a home office. With no HOA, 30-day rentals permitted, and a prime location near Siesta Village and Downtown Sarasota, this property delivers both lifestyle and upside. Highlights: - 3 Beds | 2 Baths | 1,459 Sq. Ft. - Fully restored pool (Oct 2025) - Renovated kitchen with granite & stainless - Spacious screened lanai + private preserve backdrop - Quiet cul-de-sac location - No HOA | 30-day rentals allowed - 1 mile to Siesta Key Beach One of the best-priced homes in Siesta Isles.

5223 Shadow Lawn Drive, Sarasota

$1,500,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The home sits high up on almost a 1/3 of an acre. This home was not affected by hurricane damage. Enter thru the charming Spanish style courtyard with its new landscaping, double front doors and wide foyer. Boasting a flowing floor plan with tile floors and crown molding, the living room & dining room open to the custom gourmet kitchen, featuring handsome wood cabinets, granite counters, & tumbled stone backsplash, perfect for entertaining while overlooking the Grand Canal from any window. The master bedroom ensuite with private sitting area is nice to enjoy. A new lanai cage installed July 2025. The lanai area faces southeast . There is a paver sundeck & outdoor dining area along with a covered lanai with rectangular pool, boat lift, dock, and cement seawall. Relax while you enjoy the serene water views and fabulous Florida wildlife, manatee, native birds and many types of fish. You may also enjoy fishing or kayaking from your backyard! Tropical mature foliage in park-like yard. Minutes to the open bay by boat and near Siesta Key Village where you can enjoy shops and restaurants. This truly is Paradise! Isn't this the lifestyle you've been planning? Selling Turn Key! Great Rental Income!

1038 Contento Street, Sarasota

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Here's the opportunity you have been waiting for. Incredible floor plan with this concrete block home. Large bedrooms with three on one side and the owner's suite on the other. Large in-home laundry, oversized garage and a corner lot. Wonderful private waterfront living with a pool, dock and easy access to Siesta Beach. The existing floor plan makes it easy to update and if you love terrazzo floors, they are under the carpet ready to come back alive. No water or hurricane damage sustained during last year's events, according to the owner. The owner’s suite and one of the guest suites have sliding doors to the pool lanai. Two bedrooms share a Jack and Jill bath. There's even a private outdoor shower. This is a solid home waiting for someone to update and begin creating memories. Schedule your showing today.

1014 Contento Street, Sarasota

$1,010,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Newly adjusted price - an exceptional opportunity to own a charming beach retreat on Siesta Key minutes from world-famous Siesta Beach—consistently ranked among the best beaches in the U.S. With powdery white sands, crystal-clear turquoise waters, and unforgettable Gulf sunsets close by, this home captures the essence of relaxed island living. Located in the desirable, deed-restricted community of Siesta Isles, this three-bedroom, two-bath residence is set on a lushly landscaped, nearly 15,000-square-foot lot adorned with more than 40 mature palm trees, bromeliads, and a rare, show-stopping staghorn fern. The expansive property offers exceptional outdoor privacy, ample room for entertaining or recreation, and space to add a pool. Inside, the open-concept floor plan features generously sized rooms filled with natural light. A wraparound wall of windows in the living and breakfast areas frames serene views of the tropical backyard, creating a seamless indoor-outdoor connection. The renovated kitchen is thoughtfully designed with white quartz countertops, glass tile backsplash, and newer appliances, while a separate dining room provides comfortable space for gatherings. The primary suite includes an en-suite bath and a tranquil retreat feel. Two additional bedrooms offer flexibility, including a third bedroom with contemporary barn doors—ideal for a home office, den, or guest space. With a base flood elevation of 8'8" the home remained high and dry with no water intrusion during the storms; the elevation certificate and inspection certification are available. Additional highlights include a private, low-maintenance, six-foot fenced backyard, an oversized circular paver driveway with generous parking, and a two-car garage for storage and convenience. The home may be purchased turnkey furnished (with a few exclusions), making it well-suited as a beach getaway, seasonal residence, or income-producing property. Recent improvements totaling over $100,000 add peace of mind and value, including a metal roof (2022), HVAC system (2023), paver driveway (2022), six-foot PVC fencing (2020), and re-piped sewer and water lines. Just one mile from Siesta Village’s boutiques, dining, and live music—and a short drive to downtown Sarasota’s cultural attractions, farmers markets, and waterfront destinations—this property also offers long-term potential as a future residential building site due to its prime island location. With a voluntary HOA of only $200 annually and a newly improved price, this is a compelling opportunity to secure your place on Siesta Key. Schedule your private showing today and experience the island lifestyle you’ve been waiting for.

5432 Cape Leyte Drive, Sarasota

$1,081,500

3 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this highly sought after neighborhood with its excellent boating water and close proximity to the beach. The current home on the property consists of a 3-bedrooms, 4 bathrooms and 2,337 square feet of living area. The current home experienced some water intrusion during Hurricane Helene (but not Milton).

5502 Shadow Lawn Drive, Sarasota

$1,200,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Views, Views, Views! This property is located on the desirable Grand Canal and boasts one of the best wide canal views on Siesta Key. Enjoy gorgeous long water views on 122 ft. of Canal frontage. Situated on a quiet cul-de-sac on a beautiful tree lined street with easy access to beaches and Siesta Key Village. While this home did experience some water intrusion during Hurricane Helene, it has been professionally remediated offering significant potential for you to remodel to your liking or build new. It is being sold as-is for land value only. Roof is under five years old. Minutes to beach and the vibrant Siesta Key Village. This is a unique opportunity to create your dream home. Come see why they call this street Paradise Way!

822 Paradise Way, Sarasota

$2,260,000

4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Luxury Waterfront Home on Siesta Key - Boater's and Entertainer's Paradise! Welcome to your dream waterfront retreat on Siesta Key! This stunning 4 bedroom, 3.5-bathroom home plus bonus room comes FULLY turnkey furnished ready to live in or make it an income earning vacation rental (monthly rentals allowed -some wall art is not included). There are 3 bedrooms on the main floor each with walk-in closets and the second floor is exclusively the primary suite with large walk-in closet and spa-like bathroom with an air-jetted tub. Bring your toothbrush and enjoy a home that is ready to move in, perfectly situated towards the end of a cul-de-sac street and faces a canal which leads to Sarasota Bay. Featuring a private dock with a boat lift, heated swimming pool with spa and don't forget the tropical waterslide! Duchateau flooring throughout main living areas, quartz countertops in kitchen, and travertine flooring in bathrooms. Enjoy entertaining in the extra-large party room/second living area which features a built-in bar, pool table, hideaway pocket sliders with disappearing wall that leads right to outdoor dining area/pool. There is also a bonus room that is currently being used as a home gym. The backyard is fully fenced for pets and the home did not have any water intrusion during hurricanes and sits at 8 ft elevation per the elevation certificate.

815 Paradise Way, Sarasota

$1,300,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Enjoy true Florida living on Siesta Key on this high & dry lot in beautiful Siesta Isles. This one level home offers nearly 1900 sf of living space set on a 104' wide deep-water canal lot with access to Roberts Bay, the Intracoastal, and the Gulf of Mexico. NO STORM DAMAGE during the recent hurricanes! Move right in and update it to make it your own. Offering a Split Plan of 3 bedrooms, two full bathrooms, office, art studio, and a spacious enclosed Florida Room with loads of natural light. Enjoy watching the boats cruise by from the private Gazebo overlooking 104 ft. of canal waterfront. Plenty of outdoor space in the large, fenced yard with a sweet Mango tree - this shade tree produces fruit every year and is surrounded by a brick paver patio and walkways. The home has been re-plumbed during a prior remodel along with a new roof. Bring your boat or kayak and enjoy waterfront living in Sarasota. The community with 4 miles of salt water canal front waterways and a short bike ride to the #1 rated Siesta Key Public Beach. Room for POOL and BOAT LIFT.

5402 Shadow Lawn Drive, Sarasota

$1,860,000

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

BRING ALL THE FAMILY - MOVE IN READY! Florida living on this high & dry lot on Siesta Key. Your own private tropical deep-water canal frontage. Large saltwater pool and spa, private screened courtyard adjacent to a large game room and theater room – perfect for entertaining. NO STORM DAMAGE during the recent hurricanes! This 4 BR spacious home offers 3700+ sq. ft. of living space including two primary suites, two additional bedrooms and 4.5 bathrooms. The upstairs primary ensuite bedroom, with balcony overlooking the water, offers a 19x8 walk-in closet that will excite the most discerning buyer. Other notable details include recently installed hurricane impact windows, high-end interior shutters and window treatments, undercabinet lighting in the kitchen, built-ins and upgraded flooring throughout. The office offers a custom built-in desk and hidden murphy bed. The seawall was replaced in 2022 and mooring piles installed for the owner’s 45 ft Sea Ray. A short bike ride to the #1 rated Siesta Key Public Beach. Furnishings are optional. Move in today and start enjoying paradise! Located in beautiful Siesta Isles, a boating community with saltwater waterways with access to Roberts Bay, the Intracoastal, and the Gulf.

5376 Shadow Lawn Drive, Sarasota

$1,200,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Nestled in the highly sought-after Siesta Isle neighborhood, this exceptional 14,000+ sq. ft. corner lot presents an unparalleled opportunity to create your dream home just steps from the main entrance of world-renowned Siesta Key Beach. Whether you choose to remodel the existing two-bedroom, two-bath single-family home to your specifications or build an exquisite custom estate, this prime location offers limitless potential. Unbeatable location! This home is the closest lot to the main entrance of Siesta Key Beach currently available for sale, without the premium price of being directly on the sand. Enjoy unparalleled access to one of the worlds most renowned beaches, just steps from your doorstep. A rare opportunity to own prime real estate in this highly sought-after area!

5602 Cape Leyte Drive, Sarasota

$840,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Location Location Location!!! Incredible Opportunity for this large Siesta lot that is a short walk to the beach and Siesta village! Home was a 1 time only flood from Helene and the property has been cleaned out. Come build a new home or invest in fixing this one if you choose! Almost 15300 SF of LAND! Approximately Five Minute walk to Beach Access 11! Or 10 minute walk to main public Siesta Key Beach

5420 Cape Leyte Drive, Sarasota

$1,350,000

4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers on a spacious island kitchen with generous seating, a breakfast bar, and abundant workspace, flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.

5560 Shadow Lawn Drive, Sarasota

$1,400,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Once in a generation, an opportunity to acquire a remarkable waterfront location on Siesta Key may come your way. While waterfront properties come and go, few offer the additional amenities of this coveted street, Cape Leyte Drive, situated two blocks from the remarkably world-famous destination, "Crescent Beach" with its crystal sands and turquoise water. It's not just a beach, it's a national treasure with visitors from all over the globe. Living on Siesta Key with THE beach just outside the front door, and a backyard pool plus dock on the canal, within comfortable proximity to the charming artsy Village scene of this enchanting island is worth serious consideration. Home was flooded during Helene. Owners had drywall taken out right away and A/C has been running. Being sold "As Is". Nothing warranted by sellers. Fabulous location only 2 blocks from Siesta Key public beach. Pool is salt water with no cage. Large dock with 20,000 lift ( also as is) overlooking Grand Canal. One bridge to bay. Rebuild or tear down and build new home. Terrific opportunity to own a piece of Siesta Key paradise. Close to the Village. Tremendous value. Previous owner replaced roof in 2015 among other improvements.

5537 Cape Leyte Drive, Sarasota

$1,100,000

4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

$100k PRICE REDUCTION. RARE LOCATION! Rare opportunity to live just five houses from the street entrance to famed Siesta Key public beach. No need for a car or to worry about parking. Just a 5 minute walk and you’ll be enjoying the beautiful quartz sand and crystal clear water. If that isn't enough, this rare parcel is situated between two properties, and has a direct bird's eye view of the Gulf of Mexico. Build an elevated two-story home and you’ll have Gulf views without paying $3 million+ for the lot! This property is 1/4 acre oversized lot that is 100X108 in dimension, so the possibilities are endless. Flood water entered the home. Current home had water intrusion.

5624 Cape Leyte Drive, Sarasota

$1,800,000

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

One or more photo(s) has been virtually staged. This property is priced to sell! Situated on one of the most beautiful boat basins on the island providing exceptional open serene views. Ideally poised on a generous 16,000+ sq ft lot close to the world-renowned Siesta Key Beach, this home offers easy access to powdery white sands and breathtaking sunsets. Enjoy the convenience of Siesta Village which provides nearby shops and restaurants with a variety of dining and shopping options minutes away. This home is perfect for multi-generational families or those wanting separate yet attached guest quarters. The second floor addition was added in 2008 with a separate entrance making the perfect in-law suite or 2 BR guest quarters. The home is equipped with a majority of hurricane rated windows and sliding doors. There's an opportunity for a dock at a designated cut-in on the seawall. A large oak tree with a tree swing adds a touch of nostalgia and provides the perfect spot to reflect on the lovely water views. Inside, the home is bathed in natural light, creating a warm and inviting atmosphere throughout. Five generously sized bedrooms ensure comfort and privacy for family and guests. The living areas are generously sized for entertaining with views of the water. The oversized 3 car garage has expansive storage. Step outside to your private oasis, where the expansive outdoor spaces are perfect for enjoying the Florida sunshine. A stunning pool and outdoor entertaining area offer the ideal setting for al fresco dining, lounging, and hosting gatherings with friends and family. Beautiful mature trees adorn the lot and the circular drive offers convenient access. This stunning Siesta Isles home is a rare find, offering the best of Siesta Key living. Don't miss the opportunity to make this your new waterfront paradise. Storms caused only minor exterior damage with a skim of wind-blown water in garage.

5531 Contento Drive, Sarasota

$2,075,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. WATERFRONT + ONE BLOCK TO SIESTA KEY BEACH! Location, location, location—don’t miss this chance to own a stunning canal-front home with 100 feet of frontage, just a block from the world-famous Siesta Key Beach! This property features impressive upgrades: - New Seawall and Dock - New Roof (Nov. 2022) - Hurricane-Impact Rated Windows, Sliders, Doors, and Garage Door (2023) - New Circular Driveway with Lighting - Paver Paths and Rear Patios - Newly Resurfaced Pool - Fresh Exterior Paint and Epoxied Garage Floor - All New Irrigation Lines and Landscape Lighting This meticulously updated 3-bedroom, 2-bath charmer offers captivating coastal appeal. Perfect for enjoying water activities, the coastal lifestyle, or simply relaxing in a serene setting. Seize the opportunity to own this beautiful waterfront property on Siesta Key!

5613 Cape Leyte Drive, Sarasota

$1,965,000

4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Welcome to your personal island paradise on Siesta Key! This stunning 4-bedroom, 2.5-bath home with a 2-car garage and office is the epitome of beach and boating bliss. Just a short walk from the world-renowned Siesta Key Beach, famous for its powdery white quartz sand and dazzling azure waters, this 2,527 square-foot gem sits on the grand canal, offering deep boating water and a front-row seat to spectacular, colorful sunsets every evening. Step inside to an open, light-filled floor plan that has been lovingly expanded and renovated. A new 2024 roof new gutters, 2021 & 2017 HVACs, a new second 200-amp electrical panel, a new 100-amp sub-panel, 50-amp EV charging outlet, new tankless water heater, new pool pump & heater, hurricane impact sliders, with plumbing hydrojetted, descaled & lined in 2023, provides peace of mind & affordable insurance for decades to come. The entire interior has been freshly painted, including the trim and ceilings, with new door hardware and modern touches. The bamboo floors in the bedrooms have been refinished, creating a warm & inviting atmosphere throughout. The heart of this home is the gourmet kitchen, a masterpiece of high-end design and functionality. Custom-built cabinetry with a sleek melamine finish, including a coffee station and appliance garage, all feature push-to-open mechanisms. The floating butcher block table adds a touch of charm, complemented by custom pendant lights and a ceiling flush mount light fixture in the kitchen nook. The kitchen is adorned with hand-crafted Moroccan tile and boasts top-of-the-line appliances: an Ilve Majestic II induction 36-inch range with an external venting hood, a Liebherr built-in panel-ready fridge and freezer, a Miele built-in panel-ready dishwasher, a Summit Combination Dual Zone Wine Cellar, a Moen smart touchless faucet, and a Ruvati stainless steel sink with new garbage disposal. Even the bougiest of chefs would approve! The great room and dining area flow effortlessly to the expansive outdoor entertaining space. The dining room, featuring a striking wood ceiling and sliding glass doors, opens to a lush, tropical backyard. Here, you can relax by the pool, catch some rays, or dine alfresco under the stars on the trellised patio. An extensive landscaping rebuild has transformed the yard into a tropical oasis. The owner's suite is a serene retreat with a custom wood ceiling, bamboo floors, and a large master bath featuring a separate shower, jetted tub, and new Toto toilet. French doors open to a versatile space that can serve as a den, office, or fifth bedroom. The guest wing includes three large bedrooms with bamboo floors, walk-in closets, one-and-a-half baths, and access to a private outdoor shower. For the boating enthusiast, the 14,000-pound boat lift and dock with water & power are just minutes from the open bay, with only one higher fixed bridge to the Intracoastal Waterway. The Pelican whole-house water filtration system ensures comfort and convenience, while the two-car garage with epoxy flooring & extra storage, and expansive circular driveway provide ample parking. This home is just a short walk from the vibrant Siesta Key Village, with its charming boutiques, eclectic restaurants, and lively nightlife. Downtown Sarasota, offering a wealth of shopping, dining, and cultural amenities, is only a 15-minute drive. Embrace the ultimate beach lifestyle with this Siesta Key gem. Contact us today to schedule your private showing!

5536 Contento Drive, Sarasota

$1,800,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

The moment you step into this home it presents itself with a tastefully done interior decor and captivating views of a large basin on the Grand Canal. This Coastal island neighborhood is unique since all the homes are nestled on the water! Take a 3.5 block stroll to the number one beach in the U.S with sand like powdered sugar and turquoise Gulf of Mexico waters. Fun and safe place to raise a family with minimal traffic and four Cul-De-Sac ending roads in this neighborhood for family to walk and bike safetly. East facing rear yard gives your patio some shade in the hot afternoons and yet a nice sunrise to wake up too in the morning. A Screened pool to refresh yourself after a day out on the boat. There is a boat lift which is situated to one side of the lot that allows for you to see more of the relaxing water views. The low maintenance roofing is made of Aluminum, but made to look like barrel tile. There are Lexan hurricane panels for windows and doors. . A nice sized inside laundry room is in a convenient location. There is a cozey side patio to take your morning coffee and a sunning patio next to the pool. The yard has relaxing paths and a calming feeling with the Zen style landscape design. Take a look at the photos, then the videos link, and do a walk through yourself with the matterport link option. I believe you will get a good idea of the quality and style of this home before you make your appointment to get the wonderful feeling that this home will present you the moment you arrive! Make your appointment today!!

5515 Contento Drive, Sarasota

$1,340,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Nestled in the heart of picturesque Siesta Key, this stunning turnkey 3-bedroom, 3-bathroom single-family home offers the perfect blend of luxury, comfort, and convenience. As you step inside, you're greeted by an expansive open concept living area, complete with vaulted ceilings that enhance the sense of space and elegance. Natural light floods through large windows, creating a warm and welcoming atmosphere that is perfect for both relaxation and entertaining. The home boasts a spacious primary suite, designed for ultimate comfort and privacy, featuring an en-suite bathroom that promises a tranquil retreat from the hustle and bustle of daily life. A second bedroom also includes an en-suite, offering guests or family members their own private space. The kitchen opens seamlessly to the living and dining areas, ensuring that whether you're cooking up a storm or hosting a gathering, you're always part of the action. With ample storage, and sleek countertops make this kitchen a chef's dream. Step outside to the backyard oasis, where a sparkling pool awaits, complete with a mesmerizing water feature that adds a touch of serenity. The pool area is the perfect spot for soaking up the Florida sun, hosting barbecues, or simply enjoying a quiet evening under the stars. For those who require a bit more space, the oversized two-car garage offers ample room for vehicles and storage, ensuring that your space remains clutter-free. Situated just a 1/4 of a mile from the world-renowned Siesta Key Beach, this home places you minutes away from pristine white sand beaches and crystal-clear waters. The Village of Siesta Key, with its charming shops, restaurants, and entertainment options, is only 3/4 of a mile away, making it easy to enjoy the best of what Siesta Key has to offer. This property is not only a luxurious residence but also a proven investment, boasting a great rental history. Whether you're looking for a permanent home, a vacation getaway, or a lucrative rental property, this home on Siesta Key offers it all.

5322 Cape Leyte Drive, Sarasota

$1,250,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Siesta Key Waterfront Opportunity. BEACH & BOAT! A beautiful LONG view down the canal. Almost 2000 SF, this well maintained 3/2 home located in the highly desirable Siesta Isles is just waiting for you to call it your own. The kitchen and one bathroom have been updated along with a new air conditioning. The spacious owners suite overlooks the 50 feet of water frontage and has two walk in closets, and a sliding glass door out to the extra sized screened lanai. The large backyard with direct water front is waiting for your design. A beautiful vast lot with ample room for a POOL. This home has great bones and is just waiting for the new owner to make it their own. Please contact us to see this very special one of a kind property.

5544 Contento Drive, Sarasota

$2,178,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Totally renovated in 2016, this charming canal front home is in turn-key furnished and ready for you to enjoy the Siesta Key lifestyle. Situated at the end of a cul-de-sac, on the widest part of the canal, there is nothing to do but enjoy the surrounding beauty of your tropical oasis. A new sea wall was installed in 2022, the home was repainted inside and out in 2023, hurricane grade windows and sliders, furniture purchased in 2023. Metal roof with warranty installed in 2016. When you want perfection and attention to detail, you have found your home!

5409 Azure Way, Sarasota

$1,800,000

3 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Welcome to your dream waterfront home in the highly coveted Siesta Isles canal community is a prime location of Siesta Key. Where you will experience the tranquility of this coastal neighborhood which is its own Island within an Island features many dead-end streets providing a peaceful environment for you and your family. This residence is located in the confluence of two canals, with 98 liner feet of waterfront. You'll enjoy wide breathtaking water views and have endless opportunities for water activities and boating adventures. Complete with a boat lift, dock for paddle boarding, kayaking, jet skiing, or fishing right from your backyard. Imagine starting your day with a beautiful sunrise followed by just an 8-minute walk to the main entrance of Siesta Key Beach where you will take a leisurely stroll on the white crystal sands. Spend your evenings fishing for snook, relax by the heated pool and watch the manatees and dolphins playful show or take your boat out for a short 15 minute sunset cruise to Sarasota Bay. On Sundays you can join and experience the traditional Drum Circle on the beach. 5455 Azure Way boasts 3 bedrooms, 4 bathrooms (2 en-suites), in the spacious layout with 2,736 Sq ft of living space which has been freshly painted white, inside and out, adding a modern touch of elegance and class. The open concept with high ceiling and abundance of natural light creates a bright and airy atmosphere. A generous living room-dining room combo can be ideal for entertaining guests. White modern kitchen features stainless steel appliances, double oven, tile backsplash, granite and tall cabinets provide abundance of storage. The original master bedroom is on the ground level, while the current master upstairs offers privacy and stunning views from the front and back balconies. The office/den with a full bathroom offers versatility and functionality, making it ideal for remote work or guest accommodations (with the option to convert it into another en-suite if desired). Open the large sliding glass doors for a seamless blend of indoor comfort with outdoor oasis. The screened-in brick patio offers ample room for living and dining or entertaining. Immerse yourself in the heated pool, for relaxation and rejuvenation. Whether you're enjoying a swim, simply lounging by the water's edge or enjoying a peaceful evening under the stars, everyday will feel like a vacation.Elevate your lifestyle experience and make this aspiration become your reality today!

5455 Azure Way, Sarasota

$2,250,000

4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Priced Reduced for Quick Sale! Step into your island paradise! Sold beautifully furnished, this stunningly renovated 4-bedroom 3 bath home is located in the highly sought after Siesta Isles neighborhood, just minutes to world renowned Siesta Key Beach. From the moment you enter this fabulous home, you are met with an expansive open floor plan with water views across the entire back of the house. Ideal for entertaining, this home affords multiple options for hosting, including a more-formal living room, dining area, a comfortable, cozy den with large screen television, a gourmet kitchen with sit-at bar, and a spacious screened and covered lanai with terrazzo flooring. The kitchen features all-white cabinets with black stainless appliances including a 5-burner gas cooktop, microwave/convection double wall oven, and wine refrigerator. A convenient pass-through window makes for easy food and drink service to the attached lanai. A split floor-plan, the master suite overlooks the pool and basin and incorporates a separate bedroom - perfect for young grandchildren. At the opposite side of the house a third bedroom, fourth bedroom/den/office and bath are the ideal guest retreat. New, large impact windows and sliders throughout the home allow for spectacular sunlight and vistas of the pool and basin. A beautifully manicured lawn contains a heated salt-water pool and terrace to the basin. White vinyl fencing at both sides of the lawn affords coveted privacy. A boater's dream, the dock supports a 10,000 lb lift and a convenient launch for your kayak. The attached two car garage has undergone recent enhancements including an epoxy-coated floor, steel cabinetry, and an impact exterior overhead garage door. Whether you seek an entertainer’s dream home or a serene sanctuary to call your own, this property seamlessly combines both, offering the perfect balance of luxury and tranquility. Welcome to your new paradise! Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

5319 Cape Leyte Drive, Sarasota

$1,900,000

3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Prime location on Siesta Key! This unique coastal neighborhood of Siesta Isles is it's own Island within an Island. This home sits on a desirable cul-de-sac at the end of Azure Way giving it a peaceful atmosphere with minimal traffic. The lot offers you beautiful views of the waterways that surround it because it is at the confluence of two canals. This home is walking distance to the beautiful white sand beach of the famous Siesta Beach and Siesta Village. Enjoy an early morning walk or bike ride on the beach, take a quiet kayak ride or paddle board in the canals or on the beach, watch the beautiful sunsets by the pool and experience the fun of the Sunday evening Drum Circle. A complete relaxed island lifestyle. It also has a great dock and Intracoastal boating access from the back door. This spacious home with 2,798 Sq ft of living space features all rooms on a single level with a split floor plan. There are 2 large master bedrooms each with en-suites and walk-in closets in addition to a 3rd bedroom. Multiple sliding glass doors and large windows create a natural light with stunning panoramic waterfront views. A spacious open concept family room with high ceilings. The home is situated on a 16,400 SqFt (0.38 acres) lot offering privacy from your neighbors and about 204 LFT of waterfront on the Grand Canal. Present dock can accommodate a boat up to 28 ft. long. There is also a powered boat lift which can accommodate a 9 ft. beam, and a separate kayak launch area for fishing. Pool resurfaced, pool pump and new A/C all in 2019

5400 Azure Way, Sarasota

$1,000,000

Siesta Isles SubDv. ⋅ 34242 Zip Code

Looking to build your dream home on Siesta Key? Then here is the property for you. This lot is oversized and one of the largest in Siesta Isles. Back yard is 228 feet wide, and is fenced in. Home has a swimming pool on the property. Best to remove the home that is presently there, if not it will need major renovations. Lot is located on a private cul-de-sac and is a short 1.5 blocks walk to Siesta Key Beach and pavilion. As you drive up to the home you should notice all the newer homes that have been built over the last few years. Since there is an existing home on the property, power, water and sewer are already in place.

5544 Cape Leyte Drive, Sarasota

$1,300,000

2 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Why buy a condominium when you can own your own single family home on magnificent Siesta Key, across the street from the breath-taking white sand on the most beautiful beach in the world !!! Situated on one of the largest lots near the beach, this Florida style home with salt water pool and spa is in the sought after Siesta Isles neighborhood in the heart of Siesta Key. Siesta Key Public beach is approximately 100 steps) and Siesta Key village is less than a mile away. Owner has active rental history available upon request, consisting of one long term (Jan-Mar) contract and active listings on VRBO and Airbnb with all 5 star reviews that can be transferred to new owner.

5579 Cape Aqua Drive, Sarasota

$2,475,000

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

This fabulous home has been repriced to the market. Experience the pinnacle of modern coastal living in this extraordinary four-bedroom-plus-office, four-and-a-half-bath waterfront residence. Ideally located on Siesta Key, on the deep boating water of the Grand Canal, nestled on an oversized, 16,200-square-foot lot on a private street near the renowned white quartz sands of Siesta Key Beach. This stunning contemporary home offers direct access to Sarasota Bay, making it a true haven for water enthusiasts. Upon entering, be captivated by the grandeur of the soaring 20-foot ceilings in the entryway, showcasing a floating staircase adorned with sleek stainless steel rails and cables; this architectural feature sets the tone for the entire home. Enhancing the ambiance, a two-sided fireplace serves as a central focal point, gracing both the living room and family room, boasting floor-to-ceiling walls of windows, which continue to the dining room. The heart of the home is the gourmet island kitchen, a culinary dream equipped with top-of-the-line appliances, granite countertops, and an abundance of storage, complete with a spacious pantry. The main level seamlessly combines entertainment and functionality, boasting a media room and a thoughtfully designed office space. A convenient first-floor bedroom suite adds an element of versatility and convenience. Ascend the staircase to an expansive loft overlooking the lower level, offering additional office space and a quiet reading nook. The master bedroom suite is a true retreat, with waterfront views and a private balcony - a perfect spot to unwind and enjoy a morning coffee and gentle evening breezes. An adjoining sitting room leads to the luxurious master bath, featuring a spa-like ambiance, and a generously sized walk-in closet that will indulge even the most discerning fashion enthusiast. Privacy and comfort define the split bedroom plan, with two additional guest suites on the upper level, each providing an oasis of relaxation and a private en-suite bath. Step outside to the lush outdoor living space, where the waterfront beckons. A private dock offers direct access for boating, fishing, or simply embracing the tranquility of waterfront living. Whether basking in the sun by the poolside, hosting gatherings on the expansive patio, or embarking on nautical adventures by boat, paddleboard, or kayak, every aspect of the Florida lifestyle is beautifully embraced and surrounded by lush tropical gardens. The spacious side-entry garage offers ample room for vehicles and storage, while the generously sized paver driveway and circular drive ensure no shortage of parking spaces for residents and visitors alike. Elevated construction - low flood insurance rate ($1,075/yr.) Close to Siesta Key Village’s unique boutiques and eateries, the Out-of-Door Academy, and minutes over the bridge to Sarasota’s vibrant cultural downtown, entertainment, restaurants, and shopping.

816 Edgemere Ln, Sarasota

$2,625,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Welcome to Siesta Isles on Siesta Key where you will find this completely remodeled and fully furnished 3-bedroom/ 2 bath pool home on the Grand Canal basin. All the hard work has been finished and now is the time to enjoy. This stunning home is located 6/10ths of a mile walk to the world-famous Siesta Key Beach. As you enter the home you will immediately appreciate the amazing light filled open floor plan design. The kitchen has been arranged to allow for interacting with the family and guests while preparing great meals and refreshments on the large waterfall island. An oversized great room with a full wall of pocket sliders allows for bird, fish and Manatee watching or fabulous movie nights. The master Bedroom has pocket sliders that open directly out to the covered lanai. The views continue out the rear of the home to a beautiful saltwater pool and large deck also offering a covered lanai with motorized screens. Wander down to the dock which features a IMM 16,000 lb. boat lift with water and electric service. Enjoy your evenings dockside at the outdoor fire table while listening to the pool fountain surrounded by the lush lit landscaping. The Grand Canal will take you out to the Intercoastal Waterway. You will enjoy the relaxed feel you get from this exceptional property.

925 Contento Circle, Sarasota

Browse All Siesta Isles Properties for Sale

Siesta Isles Real Estate & Homes