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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
  • /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
  • /55

    $1,750,000

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

    311 Island Cir, Sarasota, FL 34242

    Welcome to 311 Island Circle, your dream Oasis on one of Siesta Key’s most desirable streets! Nestled on an expansive 22,000 sq ft lot on Palm Island, this property comes with a shiny new 2025 Bintelli golf cart, perfect for zipping over to Siesta Beach or the Village—just a stone's throw away at less than a mile! This stunningly renovated home offers four cozy bedrooms, a dedicated office for

    Tina Ellis COMPASS FLORIDA LLC

    311 Island Cir, 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 PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3799 Flamingo Ave, Sarasota, FL 34242
  • /72

    $2,990,000

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

    512 Treasure Boat Way, Sarasota, FL 34242

    Designer Waterfront Living on Treasure Boat Way – Rare Value Meets Lasting StyleModern Waterfront Estate on Siesta Key | 512 Treasure Boat WayPerfectly situated on a spacious .44-acre corner lot in one of Siesta Key’s most sought-after boating communities, this fully renovated modern estate offers over 5,000 square feet of sophisticated living. With 4 bedrooms, 4.5 bathrooms, and a

    Derek Edwards KELLER WILLIAMS ON THE WATER S

    512 Treasure Boat Way, Sarasota, FL 34242
  • /72

    $4,799,000

    • 4 Beds
    • 4 Baths
    • 3,721 Sq Ft

    244 Cedar Park Cir, Sarasota, FL 34242

    Located in an exclusive enclave of multi-million-dollar homes, this custom residence offers a special combination of privacy, prestige, and move-in-ready waterfront living. Ideal for boating and car enthusiasts, this residence was completely updated in 2018 and is set on a beautifully landscaped 0.6-acre lot. Cedar Park owners can enjoy private beach access to a pristine beach overlooking Big

    Bev Murray BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    244 Cedar Park Cir, 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
  • /36

    $2,695,000

    • 4 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1248 Northport Dr, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Siesta Key, island living at its best. Welcome to your waterside home where you’ll enjoy a carefree, tropical lifestyle all year long. This home has been nicely maintained along with an extensive addition completed in 2015. The original home included two guest bedrooms with adjoining Jack-n-Jill bath plus a primary suite. The 1,200-square-foot

    Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1248 Northport Dr, Sarasota, FL 34242
  • /28

    $2,830,950 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
  • /6

    $3,250,000 New Construction

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

    4903 Commonwealth Dr, Siesta Key, FL 34242

    Pre-Construction. To be built. An opportunity to own a Custom Home on Siesta Key built by Nutter Custom Construction. Limited time during the pre-construction phase to influence selections. This beautifully designed Coastal Contemporary Home has 3200 sf of indoor living space and 5500 sf of total indoor/outdoor space with 3 balconies including outdoor kitchen and fantastic covered lanai. Inside

    Terence Nutter 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
  • /4

    $5,399,000 New Construction

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

    4544 Woodside Rd, Sarasota, FL 34242

    Under Construction. Welcome to your dream home on Siesta Key! This home, crafted by the esteemed custom home builder Maglich Homes, boasts over 4,000 square feet of luxurious living space with an open floor plan designed to maximize natural light and showcase breathtaking canal views. Situated on the pristine Grand Canal, this exquisite residence offers unparalleled access to the water, with just

    Thomas Cail RE/MAX ALLIANCE GROUP

    4544 Woodside Rd, 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
  • /53

    $4,200,000

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

    1444 Ridgewood Ln, Sarasota, FL 34231

    Nestled along the pristine bay-front of Sarasota, this rare waterfront property 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 to

    Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

    1444 Ridgewood Ln, Sarasota, FL 34231
  • /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
  • /81

    $1,695,000

    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    5581 Shadow Lawn Dr, Sarasota, FL 34242

    Your Siesta Key dream starts right here! This spectacular, fully renovated 4-bedroom, 3-bath home in the highly sought-after Siesta Isles community is the total package—modern, stylish, move-in ready, and just a short walk to the world-famous white sands of Siesta Beach and the vibrant energy of Siesta Village. Homes like this are rare, and this one truly checks every box. Step inside and be

    Jonathan Abrams MICHAEL SAUNDERS & COMPANY

    5581 Shadow Lawn Dr, 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
  • /37

    $1,595,000

    • 4 Beds
    • 3.5 Baths
    • 2,611 Sq Ft

    4408 Midnight Pass Rd, Sarasota, FL 34242

    BACK ON THE MARKET!! IMPROVED PRICING FOR SUMMER SALE! SELLER REDUCED 100k! Truly an escape from the ordinary! This incredible property has 2 (TWO) completely independent homes on an estate sized lot with over half an acre. Property is being sold fully furnished and ready to go! The home is also one of the 54 homes eligible for the coveted Cocoanut Bayou Association on Siesta Key which is a

    Michelle Shiver KELLER WILLIAMS ON THE WATER S

    4408 Midnight Pass Rd, Sarasota, FL 34242
  • /92

    $1,399,000

    • 4 Beds
    • 4 Baths
    • 2,927 Sq Ft

    4646 Gleason Ave, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma on our famed Siesta Key. Renovated with meticulous attention to detail,

    Logan Clark LPT REALTY, LLC

    4646 Gleason Ave, 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
  • /49

    $895,000

    • 4 Beds
    • 3 Baths
    • 1,934 Sq Ft

    514 Ralph St, Sarasota, FL 34242

    Huge Price Reduction.....Motivated Seller.....Location and opportunity...Don't miss this 4 bedroom, 3 bath pool home that sits on a well positioned larger lot with 97 ft. of canal access. The home was impacted by hurricane Helene but has been remediated and is ready for renovations, redesign or rebuild. The existing open floor plan features a large kitchen and dining area, living room with wood

    Tim Yocum, Sr COLDWELL BANKER REALTY

    514 Ralph St, Sarasota, FL 34242
  • /98

    $7,740,000

    • 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
  • /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
  • /54

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 3,451 Sq Ft

    940 Siesta Key Place, Sarasota, FL 34242

    Exceptional New Price for Siesta Key Canal-Front Living.Discover an unparalleled waterfront retreat on the highly coveted North Siesta Key, where luxury and tranquility converge. This extraordinary property boasts over 300 feet of pristine water frontage, offering breathtaking panoramic views and seamless access to Sarasota’s renowned waterways.Spanning over 3,450 sq. ft. of

    Frederick Insogna COLDWELL BANKER REALTY

    940 Siesta Key Place, Sarasota, FL 34242
  • /53

    $1,229,900

    • 4 Beds
    • 2 Baths
    • 1,915 Sq Ft

    567 Venice Ln, Sarasota, FL 34242

    SELLER CREDIT OF $20K TOWARDS CLOSING COSTS. Under the canopy of grand oaks and banyan trees, this move-in-ready FURNISHED Siesta Key POOL home offers the perfect blend of luxury and coastal charm. Located minutes from the world-famous beach and village, this retreat has been redesigned for island living with almost every inch of the home renovated to perfection!A freshly painted

    Conner Ashley PREFERRED SHORE LLC

    567 Venice Ln, Sarasota, FL 34242
  • /13

    $1,598,000

    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft

    4839 Primrose Path, Sarasota, FL 34242

    Primrose Path is a quiet street only one block long. The property has 250 feet of wide Canal front which is extremely rare. It includes a newer extra-large cement cap. The pretty setting is next to a picturesque bridge and has another long canal view facing the front of the lot. It is very close to Siesta Village. The existing house could possibly support a second-floor addition as the first

    Brian Livesey WATERSIDE REALTY LLC

    4839 Primrose Path, 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

    $1,500,000

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

    5072 Higel Ave, Sarasota, FL 34242

    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. The existing

    Georgia Salaverri COLDWELL BANKER REALTY

    5072 Higel Ave, Sarasota, FL 34242
  • /38

    $1,900,000

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

    4865 Featherbed Ln, Sarasota, FL 34242

    Canal front home on over half an acre, ideally on a quiet street just 1.5 blocks from Siesta Key Village and a short distance to Crescent Beach. The property is being sold as-is. The home did incur water damage due to recent hurricanes. Mold remediation has been performed. This desirable lot is .60 acres, an ideal place to build your dream home.

    Janet Borden PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4865 Featherbed Ln, Sarasota, FL 34242
  • /87

    $1,975,000

    • 4 Beds
    • 3.5 Baths
    • 2,641 Sq Ft

    577 Venice Ln, Sarasota, FL 34242

    NEW, NEW,NEW... COMPLETED 2021! New Price! Hands down the absolute lowest priced, best value, new construction home on Siesta Key! Why consider spending money on a wet remediated home, or a 40-year-old renovated low ceiling, low lying home with non-impact glass and plumbing and electrical infrastructure issues? Why subject yourself to those older home realities that also come with astronomical

    Robert Ruiz WILLIAM RAVEIS REAL ESTATE

    577 Venice Ln, Sarasota, 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. Pre-Construction. To be built. 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

    Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

    4644 Higel Ave, 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
  • /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
  • /94

    $7,400,000 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
$1,035,000
Median Single Family Sale Price
$1,035,000
Average Price Per Sq Ft
$582
Number of Homes for Sale
1
Last 12 months Home Sales
2
Months of Supply
6.00
Median List Price
$1,300,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-76%
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