2-Story Homes for Sale in 34242

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  $899,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5250 Calle de Rio, Sarasota, FL 34242

  Just a short two-block stroll from Siesta Key's vibrant village, you'll find yourself surrounded by a delightful array of casual and fine dining restaurants, lively shops, and bars with nightly live music. Yet, this charming home is nestled in a peaceful, quiet neighborhood; offering the perfect blend of convenience and tranquility. Enjoy the best of both worlds with a short walk or bike ride to

  Kelli Eggen COLDWELL BANKER REALTY

  5250 Calle de Rio, Sarasota, FL 34242
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  $1,099,000

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  4117 Roberts Point Cir, Sarasota, FL 34242

  Nestled on a tranquil street, in the highly sought-after Roberts Point neighborhood of Siesta Key, this stunning elevated home offers the perfect blend of luxury, privacy, and coastal charm. Situated just moments from the world-renowned Siesta Beach and the vibrant Siesta Village, this beautifully maintained two-story residence offers the perfect combination of comfort, convenience, and Florida

  Jim Mast KELLER WILLIAMS ON THE WATER S

  4117 Roberts Point Cir, Sarasota, FL 34242
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  $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
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  $1,998,000

  • 3 Beds
  • 3 Baths
  • 2,628 Sq Ft

  3721 Flamingo Ave, Sarasota, FL 34242

  Highly Motivated Sellers! Bring All Offers to rebuild your dream home in the exclusive community of Bay Island nestled on the Barrier Island of Siesta Key! Remodel, Rebuild or bring a development opportunity to desirable north Siesta Key. Bay Island is a true gem - this highly sought-after community of single-family neighborhoods on Siesta Key, offers unparalleled privacy and luxury. Great

  Sandra McCourtney FINE PROPERTIES

  3721 Flamingo Ave, Sarasota, FL 34242
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  $8,250,000

  • 3 Beds
  • 4 Baths
  • 3,788 Sq Ft

  679 Norsota Way, Sarasota, FL 34242

  Set on one of the most coveted streets on Siesta Key, this beautifully crafted 1926 Spanish-style home sits on a double lot with 150 feet of deep-water bay frontage, significantly larger than most properties’ 100 feet of frontage. Spanning 3,788 square feet with three bedrooms and four bathrooms, this gorgeous historic home exudes timeless character and craftsmanship and showcases authentic

  Michael Hays MICHAEL SAUNDERS & COMPANY

  679 Norsota Way, Sarasota, FL 34242
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  $5,995,000

  • 6 Beds
  • 7 Baths
  • 7,099 Sq Ft

  4136 Roberts Point Cir, Sarasota, FL 34242

  Situated on the coveted North end of Siesta Key, this waterfront retreat offers a perfect blend of luxury, elegance, and tranquility with breathtaking views of South Coconut Bayou and direct access to Roberts Bay. Thoughtfully designed to embrace natural light, the home features soaring ceilings, oversized windows, and seamless indoor-outdoor living spaces. The gourmet kitchen stands out with

  Nina Bayan KELLER WILLIAMS ON THE WATER S

  4136 Roberts Point Cir, Sarasota, FL 34242
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  $1,899,000

  • 2 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  5112 Jungle Plum Rd, Sarasota, FL 34242

  Attention architecture enthusiasts: This midcentury-modern waterfront home seamlessly blends timeless design with modern convenience. Resilient through three major storms, it sustained no damage beyond minor landscaping impacts and minimal water in the garage. Set on a lush 0.61-acre lot in the coveted Hidden Harbor neighborhood, this jungle oasis offers an unparalleled living experience. The

  Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5112 Jungle Plum Rd, Sarasota, FL 34242
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  $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
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  $4,950,000

  • 1 Bed
  • 1 Bath
  • 1,500 Sq Ft

  3460 Flamingo Ave, Sarasota, FL 34242

  New price! Exclusive waterfront opportunity on Siesta Key. Discover the pinnacle of waterfront living with this gated, estate-sized 1.27-acre property located on highly coveted Bay Island at the desirable north end of Siesta Key. This exceptional property is a boater's paradise, offering 178 feet of sailboat (no bridges) waterfront with oversized dockage and unparalleled access to the Gulf of

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3460 Flamingo Ave, Sarasota, FL 34242
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  $2,750,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,943 Sq Ft

  508 Siesta Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Experience the ultimate in coastal living with this two-story residence in the highly desirable Bay Island Shores on the world-renowned Siesta Key. Located in a prime waterfront setting, this all-concrete block home boasts a new tile roof in 2016 and offers unparalleled access to deep water and sailboat-friendly waters, making it the perfect haven

  Kevin Milner PREMIER SOTHEBY'S INTERNATIONAL REALTY

  508 Siesta Dr, Sarasota, FL 34242
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  $650,000

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft

  4189 Roberts Point Cir, Sarasota, FL 34242

  Motivated Seller! This is a rare opportunity on the north end of Siesta Key for investors or homeowners looking to renovate, rebuild, or start fresh. Set on a secluded 6,250 sq. ft. lot in one of Sarasota’s most desirable island communities, this property includes a 3-bedroom, 2-bath, 1,757 sq. ft. home that has been professionally remediated following storm damage. Buyers have multiple options:

  Shane Lewis MICHAEL SAUNDERS & COMPANY

  4189 Roberts Point Cir, Sarasota, FL 34242
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  $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
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  $1,398,000

  • 6 Beds
  • 5 Baths
  • 3,549 Sq Ft

  4915 Primrose Path, Sarasota, FL 34242

  Fantastic lot to build your dream house on ~ .32 of an ACRE and on a great canal-front lot (100x154x81). CONSTRUCTION FINACING AVAILABLE FOR QUALIFIED BUYER! This home has had significant storm damage and is now being sold as a tear down!! Situated in one of Sarasota’s premier canal locations, this property is located a quick bike ride to the beautiful sands of Siesta Key beach. Siesta Key

  Tony Andrews ANDREWS & ASSOCIATES REALTY

  4915 Primrose Path, Sarasota, FL 34242
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  $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
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  $499,000

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit C12, Sarasota, FL 34242

  PRICE DECREASE! The perfect opportunity for the Florida Lifestyle! MOVE-IN READY. This 2-bed, 2.5-bath condo is being sold TURNKEY FURNISHED with comfortable living space, all in WALKING distance from the sugary sands of Siesta Key Beach. This is a great investment opportunity as Bay Oaks has a ONE WEEK RENTAL MINIMUM. Inside, enjoy a spacious and homey area for relaxing or entertaining. The

  Ariela Carmona KELLER WILLIAMS ON THE WATER S

  6157 Midnight Pass Rd Unit C12, Sarasota, FL 34242
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  $28,000,000 New Construction

  • 7 Beds
  • 9 Baths
  • 8,570 Sq Ft

  4050 Higel Ave, Siesta Key, FL 34242

  Pre-Construction. To be built. This unmatched luxury beach estate on direct gulf frontage will show sweeping ocean views, with its own private beach on Siesta Key. The upcoming iconic estate plan hosts resort-level amenities in its privately gated and tucked away property, which is being developed, built, and designed by M&J Pham Development. The stunning newly constructed home will have 16,547

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  4050 Higel Ave, Siesta Key, FL 34242
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  $5,495,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,676 Sq Ft

  8800 Midnight Pass Rd, Sarasota, FL 34242

  Auction Property. LUXURY REAL ESTATE AUCTION on-site on Wednesday, August 20, 2025, at 11:00 a.m. Previews begin on Saturday, August 2 and will run every Saturday and Sunday from 1:00 to 4:00 p.m. until the auction. Private appointments are available; please call for details. Host your family, friends, or dream vacations at this New Construction Luxury Beach House with Ocean Views on

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  8800 Midnight Pass Rd, Sarasota, FL 34242
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  $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
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  $16,000,000 New Construction

  • 5 Beds
  • 5 Baths
  • 5,524 Sq Ft

  7324 Point of Rocks Rd, Sarasota, FL 34242

  Under Construction. Imagine waking up to the soft sound of waves, stepping onto your private terrace, and feeling the soothing Gulf breeze as the sun rises. This is the Siesta Key lifestyle—a rare blend of barefoot luxury, tranquility, and world-class beauty. Property adjacent is available for sale as well. Making it possible for a beautiful estate and privacy.Set to be completed by

  Karen Chandler MICHAEL SAUNDERS & COMPANY

  7324 Point of Rocks Rd, Sarasota, FL 34242
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  $18,905,000 New Construction

  • 5 Beds
  • 9 Baths
  • 6,985 Sq Ft

  4214 Higel Ave, Sarasota, FL 34242

  Pre-Construction. To be built. Presenting an unparalleled opportunity to bring a world-class waterfront estate to life. 4214 Higel Avenue is one of only 7 estates on this ultra-exclusive stretch of Siesta Key boasting a private beach. Designed by Stofft-Cooney Architects in collaboration with Perrone Construction, this visionary concept offers the foundation for an extraordinary coastal

  Hailey Kendall WILLIAM RAVEIS REAL ESTATE

  4214 Higel Ave, Sarasota, FL 34242
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  /13

  $6,270,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,400 Sq Ft

  44 Rockwell Ln, Sarasota, FL 34242

  Pre-Construction. To be built. WALK TO YOUR OWN PRIVATE BEACH!New construction on Sandy Hook.Inspirational photo only. Buyer may use our design, or work with our team for custom design requirements.Final Plans "must" be approved by Sandy Hook HOA.All rules to met and approved before construction begins.Call for all details. Many possibilities. 12 month build

  Joseph Russo COURTYARD MODERN

  44 Rockwell Ln, Sarasota, FL 34242
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  $29,995,000 New Construction

  • 7 Beds
  • 11 Baths
  • 13,035 Sq Ft

  3990 Higel Ave, Sarasota, FL 34242

  Under Construction. Welcome to 3990 Higel Avenue, set to be completed in early 2026 and can be offered fully furnished. Where architectural brilliance meets unrivaled luxury on Sarasota’s exclusive Gulf-front shores. 3990 Higel is 1 of 1. Having direct ocean frontage while having the ability to have your own private bock/lift. This 13,035 square-foot masterpiece is designed by the acclaimed DSDG

  Adnan Dedic COMPASS FLORIDA LLC

  3990 Higel Ave, Sarasota, FL 34242
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  $18,000,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,853 Sq Ft

  3200 Higel Ave, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to 3200 Higel Ave, an extraordinary waterfront estate that exudes unparalleled luxury and sophistication, by M&J Pham Development. Set on the pristine shores of Sarasota Bay, this 2025 under construction masterpiece offers a boater’s dream lifestyle combined with breathtaking views of Big Pass, South Lido Beach

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  3200 Higel Ave, Sarasota, FL 34242
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  $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
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  $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

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