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4-Bedroom Houses for Sale in Siesta Key, FL with Private Pool

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  • /85

    $1,800,000

    • 4 Beds
    • 2 Baths
    • 2,185 Sq Ft

    746 Plymouth St, Sarasota, FL 34242

    Nestled in the heart of Siesta Key, this home offers the perfect blend of relaxation and opportunity. Whether you're seeking a serene beach getaway, a lucrative vacation rental, or a full-time residence, this property checks all the boxes. The home’s unique floor plan is flooded with natural light, creating a bright, inviting atmosphere throughout. A rare find, both the home and the garage are

    Agent Photo

    Carla Rayman Kidd

    COLDWELL BANKER REALTY

    (941) 239-2641

    746 Plymouth St, Sarasota, FL 34242
  • /42

    $5,392,000 New Construction

    • 4 Beds
    • 6 Baths
    • 4,220 Sq Ft

    4819 Higel Ave, Sarasota, FL 34242

    New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths and two half baths. Step inside the

    Agent Photo

    Cassandra Meyer

    BRIGHT REALTY

    (941) 231-6297

    4819 Higel Ave, Sarasota, FL 34242
  • /76

    $18,500,000

    • 4 Beds
    • 6 Baths
    • 8,138 Sq Ft

    3799 Flamingo Ave, Sarasota, FL 34242

    Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with

    Joel Schemmel DOUGLAS ELLIMAN

    3799 Flamingo Ave, Sarasota, FL 34242
  • /100

    $2,699,999

    • 4 Beds
    • 3 Baths
    • 3,541 Sq Ft

    5012 Higel Ave, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts

    Rachelle Tirey PREFERRED SHORE LLC

    5012 Higel Ave, Sarasota, FL 34242
  • /98

    $6,995,000

    • 4 Beds
    • 4.5 Baths
    • 5,532 Sq Ft

    3935 N Shell Rd, Siesta Key, FL 34242

    Nestled along the pristine northern shores of Siesta Key, this magnificent three-story waterfront retreat redefines coastal luxury and exclusivity. The home features 10,600 sq ft under roof with approximately 5,500sq ft under air. This exceptional home is crafted for grand entertaining and effortless relaxation. While Siesta Beach and Village are just minutes away by golf cart, the gated personal

    Curtis Ware KW COASTAL LIVING III

    3935 N Shell Rd, Siesta Key, FL 34242
  • /6

    $6,000,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,482 Sq Ft

    4644 Higel Ave, Sarasota, FL 34242

    Pre-Construction. To be built. Under construction. Designed and developed by the renowned M&J Pham Development team, this residence is a masterpiece of innovative design and flawless craftsmanship, offering unparalleled luxury and coastal elegance at 4644 Higel Avenue, Sarasota. Nestled on a nearly 14,000-square-foot lot with 118 feet of prime canal frontage, this waterfront home blends modern

    Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

    4644 Higel Ave, Sarasota, FL 34242
  • /24

    $3,250,000 New Construction

    • 4 Beds
    • 4 Baths
    • 3,146 Sq Ft

    4903 Commonwealth Dr, Siesta Key, FL 34242

    Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. This Coastal Contemporary residence offers 3,200 sq. ft. of interior living space and over 5,500 sq. ft. of total indoor/outdoor living, thoughtfully designed to maximize both luxury and comfort. Enjoy three spacious balconies, an outdoor kitchen, and a generous covered

    Morgan Marziali NCC PROPERTIES LLC

    4903 Commonwealth Dr, Siesta Key, FL 34242
  • /100

    $4,299,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,996 Sq Ft

    603 Tremont St, Siesta Key, FL 34242

    Perfectly positioned in the heart of Siesta Key, this masterfully crafted new construction estate by M&J Pham Development epitomizes modern luxury and architectural brilliance, offering 3,996 square feet of exquisitely designed living space with 4 bedrooms and 4.5 bathrooms. From the moment you step inside, you are greeted by a breathtaking open-concept layout accentuated by soaring 20-foot

    Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

    603 Tremont St, Siesta Key, FL 34242
  • /94

    $5,399,000 New Construction

    • 4 Beds
    • 6 Baths
    • 4,007 Sq Ft

    4544 Woodside Rd, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Welcome to a brand-new coastal masterpiece that redefines luxury living on world-renowned Siesta Key. Designed with both sophistication and comfort in mind, this waterfront retreat blends timeless architecture with modern amenities, all just moments from Siesta Village and the powdery sands of Siesta Beach. Inside, soaring ceilings and walls of

    Thomas Cail RE/MAX ALLIANCE GROUP

    4544 Woodside Rd, Sarasota, FL 34242
  • /52

    $3,250,000

    • 4 Beds
    • 4 Baths
    • 3,256 Sq Ft

    300 Garden Ln, Sarasota, FL 34242

    A Rare Opportunity on North Siesta Key – 350 Feet of Waterfront!Discover this unique single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—is truly a boater’s and

    Holly Parry WILLIAM RAVEIS REAL ESTATE

    300 Garden Ln, Sarasota, FL 34242
  • /53

    $3,900,000

    • 4 Beds
    • 3 Baths
    • 3,471 Sq Ft

    1444 Ridgewood Ln, Sarasota, FL 34231

    Substantial bayfront property with sweeping views , this rare waterfront location offers an unparalleled opportunity for builders and investors alike. Boasting an impressive 255 feet of water frontage, this 4-bedroom, 3-bath home is perfectly positioned to capture breathtaking sunsets and panoramic bay views. Whether you choose to renovate the existing residence or create a custom luxury estate

    Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

    1444 Ridgewood Ln, Sarasota, FL 34231
  • /70

    $5,950,000

    • 4 Beds
    • 4.5 Baths
    • 6,827 Sq Ft

    749 Freeling Dr, Sarasota, FL 34242

    Experience coastal elegance and ultimate island living in this extraordinary gated waterfront estate, Casa della Fontana, the Fountain House. This home offers the ideal blend of luxury, privacy, and convenience on a tranquil street on Siesta Key's coveted north end. Just minutes from everything on and off the island, this residence is poised on a deep sailboat water bayou just off Sarasota Bay

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    749 Freeling Dr, Sarasota, FL 34242
  • /100

    $2,450,000

    • 4 Beds
    • 3.5 Baths
    • 2,988 Sq Ft

    5365 Calle Florida, Sarasota, FL 34242

    This newer construction home is perfect for year-round living or as a beach retreat. Additionally, it has made nearly $100,000.00 in rental income. Its design and amenities are exceptional as is it’s versatility! The elevator extends from the street level 3+ car garages to the main living floor and the upper floor. You are greeted on the main floor with a large living room opening to a main

    David DAngelo MICHAEL SAUNDERS & COMPANY

    5365 Calle Florida, Sarasota, FL 34242
  • /40

    $1,100,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 1,967 Sq Ft

    795 Plymouth St, Sarasota, FL 34242

    Welcome to your slice of paradise on Siesta Key. This beautifully updated 4-bedroom home offers the perfect blend of coastal charm and modern comfort, nestled on a peaceful, tree-lined street in one of the island’s most sought-after neighborhoods. Step inside to discover a bright, airy interior filled with natural light, where spacious living areas flow effortlessly into a large open-air pool,

    Courtney Church COLDWELL BANKER REALTY

    795 Plymouth St, Sarasota, FL 34242
  • /41

    $1,895,000

    • 4 Beds
    • 3 Baths
    • 2,450 Sq Ft

    4879 Commonwealth Dr, Sarasota, FL 34242

    Own a Rare Piece of Sarasota's Architectural History on Siesta Key!Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly

    Daniel Petrilla PREFERRED SHORE LLC

    4879 Commonwealth Dr, Sarasota, FL 34242
  • /72

    $2,795,000 Open Wed 12PM - 2PM

    • 4 Beds
    • 4.5 Baths
    • 5,078 Sq Ft

    512 Treasure Boat Way, Sarasota, FL 34242

    Elevated Living. Expanded Luxury. Move-In Ready.More space. More land. More peace of mind — and better value than new construction.This rare Siesta Key estate offers twice the living space and double the lot size of typical new construction homes on the Key, while sitting high and dry on an above-flood-level lot. No construction delays. No compromises.Designer Waterfront

    Derek Edwards KELLER WILLIAMS ON THE WATER S

    512 Treasure Boat Way, Sarasota, FL 34242
  • /57

    $2,900,000

    • 4 Beds
    • 4 Baths
    • 2,854 Sq Ft

    238 Island Cir, Sarasota, FL 34242

    Welcome to your dream island retreat, perfectly nestled in the heart of Siesta Key’s Palm Island, just minutes away from the world-famous Siesta Beach and vibrant Siesta Village. This beautifully renovated 4-bedroom, 4-bathroom home is the epitome of coastal luxury, offering the ultimate island lifestyle where you can enjoy sun, sand, and all the amenities of this exclusive locale. Meticulously

    Thomas Cail RE/MAX ALLIANCE GROUP

    238 Island Cir, Sarasota, FL 34242
  • /21

    $1,850,000

    • 4 Beds
    • 3 Baths
    • 2,392 Sq Ft

    306 Island Cir, Sarasota, FL 34242

    Move right in to this freshly renovated waterfront home, located on Palm Island, the "Heart of Siesta Key". Four bedrooms, two with en-suite bathrooms, large open floor plan, stylish new kitchen, sparkling swimming pool with spa, a dock with boat lift, and low maintenance landscape. This home has it all! Move in now and start enjoying the beach and boating lifestyle one can only find on Siesta

    Timothy Bloch QUEST PROPERTIES INC

    306 Island Cir, Sarasota, FL 34242
  • /48

    $1,595,000

    • 4 Beds
    • 2.5 Baths
    • 2,598 Sq Ft

    749 Tropical Cir, Sarasota, FL 34242

    Siesta Key sanctuary, a coastal retreat with modern luxury. Discover a private tropical paradise in this contemporary, renovated four-bedroom, 2.5-bath pool home, ideally on nearly half an acre in one of Siesta Key’s sought-after communities. Designed with elegance and ease in mind, this stunning concrete block residence blends timeless charm with modern upgrades, offering the ultimate coastal

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    749 Tropical Cir, Sarasota, FL 34242
  • /86

    $7,495,000

    • 4 Beds
    • 4.5 Baths
    • 7,003 Sq Ft

    4205 Higel Ave, Sarasota, FL 34242

    New price! Palm Beach meets Siesta Key, a waterfront masterpiece. A stunning Palladian villa with a modern twist, this gated waterfront estate on the protected deep waters of Cocoanut Bayou offers an unparalleled blend of luxury, elegance and coastal serenity. Boasting 120 feet of deep sailboat water, a private dock, private beach access, and partial gulf views, this exquisite home presents over

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4205 Higel Ave, Sarasota, FL 34242
  • /47

    $1,695,000

    • 4 Beds
    • 3 Baths
    • 2,124 Sq Ft

    5560 Shadow Lawn Dr, Sarasota, FL 34242

    New price! Discover the epitome of coastal living with this stunning waterfront home on Siesta Key, steps from the world-famous white sands of Siesta Beach and the aqua waters of the Gulf of Mexico. On an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath oasis offers an unparalleled blend of luxury and comfort. Entertain effortlessly in the open-concept floor plan, featuring

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    5560 Shadow Lawn Dr, Sarasota, FL 34242
  • /33

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 2,753 Sq Ft

    5072 Higel Ave, Sarasota, FL 34242

    SIGNIFICANT PRICE IMPROVEMENT! Discover the rare opportunity to build or renovate on an exceptional .36-acre canal-front property located in the sought-after Sara Sands neighborhood on Siesta Key. Tucked away in a serene, upscale enclave just moments from the vibrant Siesta Key Village and the world-renowned Siesta Key Beach, this property offers the perfect blend of tranquility and convenience.

    Susie Gillum COLDWELL BANKER REALTY

    5072 Higel Ave, Sarasota, FL 34242
  • /28

    $2,730,950 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    105 Island Cir, Sarasota, FL 34242

    Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be

    Linda Scheller COLDWELL BANKER REALTY

    105 Island Cir, Sarasota, FL 34242
  • /44

    $2,800,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    6924 Bochi Cir, Sarasota, FL 34242

    Under Construction. **Short term promotional pricing, take advantage now while it's available!**Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels,

    Jeremy Hartmark LPT REALTY, LLC

    6924 Bochi Cir, Sarasota, FL 34242
  • /9

    $4,985,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,132 Sq Ft

    558 Venice Ln, Sarasota, FL 34242

    Under Construction. –A luxury, Coastal Contemporary Home on Siesta Key. Welcome to your future coastal retreat, brought to life by Heritage Builders, an award-winning custom home builder known for excellence in design and craftsmanship. This stunning two-level waterfront residence on Siesta Key offers the pinnacle of luxury living, with 4,132 square feet of thoughtfully designed space, four

    Sara Boudarga HB REALTY GROUP INC.

    558 Venice Ln, Sarasota, FL 34242
  • /15

    $4,795,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,995 Sq Ft

    601 Tremont St, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Under Construction. Set in a hammock of old growth oak trees and mature landscaping, this masterpiece of a home sits on over 1/3 of an acre and is located on one of the most treasured streets on Siesta Key. It is just a short walk from The Out-of-Door Academy, minutes from the world-famous Siesta Key Village and another few blocks to our cherished

    Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

    601 Tremont St, Sarasota, FL 34242
  • /94

    $6,995,000 New Construction

    • 4 Beds
    • 6 Baths
    • 4,711 Sq Ft

    3550 Flamingo Ave, Sarasota, FL 34242

    READY FOR OCCUPANCY. CONSTRUCTION COMPLETED. LOWEST NEW CONSTRUCTION price on highly desirable North Siesta Key. Situated on 1/3 acre with 102 feet of wide canal waterfront and no bridges to the bay. The 4,711 square foot home is solid block construction on all levels. The house has been thoughtfully designed, maximizing privacy and use of space. The main level features a designer kitchen with an

    Barbara May MICHAEL SAUNDERS & COMPANY

    3550 Flamingo Ave, Sarasota, FL 34242

Home Trends in Siesta Key, FL

Housing Trends

Median Sale Price
$2,600,000
Median Single Family Sale Price
$2,975,000
Median 2 Bedroom Sale Price
$750,000
Average Price Per Sq Ft
$1,095
Number of Homes for Sale
7
Last 12 months Home Sales
3
Months of Supply
28.00
Median List Price
$2,812,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-41%
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