Location: Siesta Isles, Sarasota
Do Not Show Listings
814 PARADISE WAY, SARASOTA, FL 34242
$1,995,00026 Days on yellowkey MLS ID: TB8483961
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1962Monthly Fee: $17 Tax: $14,830 (2025)Community: Siesta IslesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,830
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: 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.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
5507 CONTENTO DR, SARASOTA, FL 34242
$1,775,00040 Days on yellowkey MLS ID: A4683288
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSingle Family
Taxes:$15,484
Middle School: Sarasota Middle
Remarks: 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***
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
5569 CAPE LEYTE DR, SARASOTA, FL 34242
$4,495,00020 Days on yellowkey MLS ID: A4685577
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3654 Built: 2016 Tax: $32,419 (2025)Community: Siesta IslesSingle Family
Taxes:$32,419
Remarks: LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one bridge with about 15’ clearance to the Gulf). Oversized 16,163 sf Lot, elevated concrete block home and spectacular pool in your view from most every room! Not just the best location, but this custom-built in 2016 West Indies style home is a fortress all on one level, including the pool, and is well above the FEMA flood zone. High and dry through the "storms of the century" in 2024. Beautiful, engineered hardwood floors, custom cabinetry throughout by Elite Woodworking in the Kitchen, all Bathrooms and Great Room. The entire house has been freshly painted inside & out. Three large en-suite bedrooms. Additional rooms currently utilized as office with Murphy Bed as well as very large Bonus Room could be utilized as additional bedrooms #4 & 5, if desired. Even the powder bath has a shower for guest convenience. Large walls of sliding glass doors in all waterfront rooms extend living spaces to a huge, screened Lanai which adds over 500 sf to living space under roof, and much more in the screened Lanai area.. All hurricane rated extra heavy duty PGT doors and windows. The total A/C space is 3,654 sf, with a overall total of 5,075 under roof. The oversized 3-car garage with an Epoxy floor has a very high ceiling which allows 2 more cars to be added on lifts for a total of 5 vehicles for the enthusiast. Isonene insulated and floored attic storage space is available above the garage. New in the past year: A/C Condenser & Air Handler system in 1 (of 2) zones, water heater, refrigerator, ice maker, boat lift control boxes on both Lifts. The large free form pool and spa have new (wifi) Pentair pool pump & heater & auto chlorinator. Both boats as well as professional decorator staged furniture, decor and pictures may be available for separate purchase for "Turn-Key" possession. DEFINITELY check out the Virtual Tour, since it provides “3D walk through any direction” photos which can really give you the flow of the house as you manipulate your way around.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Steve Hagan (941-900-4126)
5432 CAPE LEYTE DR, SARASOTA, FL 34242
$1,125,000343 Days on yellowkey MLS ID: A4649500
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1659 Built: 1974Monthly Fee: $21 Tax: $10,946 (2025)Community: Siesta Isles Unit 2Single Family
Taxes:$10,946
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,549,000434 Days on yellowkey MLS ID: A4636955
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2124 Built: 1970Monthly Fee: $17 Tax: $8,052 (2025)Community: Siesta IslesSingle Family
Taxes:$8,052
Remarks: Siesta Key Waterfront Living—Priced to Embrace the Island Lifestyle An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this beautifully maintained residence is ideally positioned just moments from the powdery white sands of 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 around a spacious island kitchen with generous seating, 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 durable 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.
5362 SHADOW LAWN DR, SARASOTA, FL 34242
$5,395,000148 Days on yellowkey MLS ID: A4667008
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 4294 Built: 2023Community: Siesta IslesSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 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
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
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