15

Siesta Key, FL Homes for Sale under $2,000,000

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  • /60

    $1,999,999

    $249K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    5361 Siesta Ct, Sarasota, FL 34242

    PRICE IMPROVEMENT! Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior

    David James CHARLES RUTENBERG REALTY INC

    5361 Siesta Ct, Sarasota, FL 34242
  • /84

    $1,600,000

    • 3 Beds
    • 2.5 Baths
    • 2,557 Sq Ft

    5231 Siesta Cove Dr, Sarasota, FL 34242

    Tucked inside the private enclave of Siesta Cove, this beautifully updated island home offers that rare blend of privacy, space, and an easy walk to world-famous Siesta Key Beach. Set on an oversized 0.35-acre lot, the property features 3 bedrooms, 2.5 baths, and more than 2,500 square feet of bright, open living space designed for both everyday comfort and effortless entertaining. Vaulted

    Natalie Gutwein MICHAEL SAUNDERS & COMPANY

    5231 Siesta Cove Dr, Sarasota, FL 34242
  • /20

    $1,700,000

    • Land
    • 14,810 Sq Ft
    • $5,000,000 per Acre

    5323 Calle Florida, Sarasota, FL 34242

    Rare Double-Lot Coastal Compound Opportunity on Siesta Key — Offered Together at $1,700,000 | 14,636 Total Sq. Ft.Embrace the quintessential Florida lifestyle on prestigious Palm Island—a peaceful, golf-cart-friendly sanctuary surrounded by deep-water canals, mature tropical canopies, and magnificent luxury residences. Combining Lot A (8,619 sq. ft.) and Lot B (6,017 sq. ft.), this rare

    Bethany Behrmann REAL BROKER, LLC

    5323 Calle Florida, Sarasota, FL 34242
  • /11

    $1,595,000

    • Land
    • 13,503 Sq Ft
    • $5,145,161 per Acre

    4950 Commonwealth Dr, Sarasota, FL 34242

    Unique opportunity to own an exceptional double-lot homesite on the Grand Canal on Siesta Key. Tucked away on a quiet cul-de-sac in one of the island’s most desirable waterfront neighborhoods, this expansive property offers 107 feet of canal frontage and seawall, creating an outstanding setting for your future Siesta Key residence.Located along a low-wake arm of the Grand Canal, the

    Andrew Haddad COMPASS FLORIDA LLC

    4950 Commonwealth Dr, Sarasota, FL 34242
  • /58

    $1,589,000

    • 2 Beds
    • 2 Baths
    • 2,042 Sq Ft

    1280 Dolphin Bay Way Unit 402, Sarasota, FL 34242

    Welcome to Dolphin Bay, one of Siesta Key's premier waterfront communities, where luxury coastal living meets breathtaking scenery. This beautifully maintained 2-bedroom, 2-bath residence offers 2,217 square feet of thoughtfully designed living space with panoramic views of the Intracoastal Waterway, downtown Sarasota, and beyond.Filled with natural light, the open-concept floor plan was

    Mary Zilinskiy COLDWELL BANKER REALTY

    1280 Dolphin Bay Way Unit 402, Sarasota, FL 34242
  • /53

    $1,649,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242

    It's all about THE VIEW and the DIRECT SIESTA KEY BEACH ACCESS!!! This first floor condominium has a FULL GULF VIEW from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You'll walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion or water damage to this unit in past storms, as several

    Susan Keal MICHAEL SAUNDERS & COMPANY

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242
  • /40

    $1,795,000

    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft

    6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242

    From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an

    Roger Pettingell COLDWELL BANKER REALTY

    6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242
  • /52

    $1,559,000

    • 2 Beds
    • 2 Baths
    • 1,187 Sq Ft

    5400 Ocean Blvd Unit 17-04, Sarasota, FL 34242

    The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and durability. Situated directly on Siesta Key Beach, and built with walls of sliding glass doors in every room to take advantage of the diverse, magnificent views in all directions. This is the penthouse being offered turnkey

    Carol Thomas MICHAEL SAUNDERS & COMPANY

    5400 Ocean Blvd Unit 17-04, Sarasota, FL 34242
  • /41

    $1,500,000

    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft

    6146 Midnight Pass Rd Unit 12S, Sarasota, FL 34242

    Best beachfront value on Siesta Key!!!This second-floor condo features two bedrooms and two bathrooms, including a primary ensuite with a king-size bed and a guest bedroom. The interior offers a spacious living area, a formal dining space, and a fully equipped kitchen with granite countertops. Residents and guests can enjoy spectacular views of the Gulf of Mexico and sunsets from the private

    Joshua Beckmann BECKMANN REAL ESTATE

    6146 Midnight Pass Rd Unit 12S, Sarasota, FL 34242
  • /76

    $1,950,000

    Open House 10/04
    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft

    5740 Midnight Pass Rd Unit 403, Sarasota, FL 34242

    A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked.From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping

    Drew Jacobsen COMPASS FLORIDA LLC

    5740 Midnight Pass Rd Unit 403, Sarasota, FL 34242
  • /71

    $1,850,000

    • 3 Beds
    • 2 Baths
    • 2,165 Sq Ft

    5880 Midnight Pass Rd Unit 907, Sarasota, FL 34242

    TOP FLOOR. TOP BEACH. TOP NOTCH. This Siesta Key condo checks ALL the hard to find boxes — THREE bedrooms. PRIVATE Beach. TOP Floor. RESORT Style Amenities. GARAGE Parking Space. NO Work Needed! Welcome to Unit 907, a beautifully refreshed top-floor residence offering generous living space, a calm coastal feel, and the easy beach lifestyle buyers are looking for. From the moment you open the

    Christa Spalding COLDWELL BANKER REALTY

    5880 Midnight Pass Rd Unit 907, Sarasota, FL 34242
  • /64

    $1,500,000

    • 2 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1280 Dolphin Bay Way Unit 504, Sarasota, FL 34242

    At the pinnacle of an intimate, gated community on world-renowned Siesta Key, this penthouse condominium offers a rare opportunity to enjoy sweeping bayfront living with breathtaking views stretching across the water to the skyline of Sarasota. Offered turnkey furnished, this beautifully maintained residence is ready for immediate enjoyment, whether as a full-time home or a luxurious island

    Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1280 Dolphin Bay Way Unit 504, Sarasota, FL 34242
  • /2

    $1,900,000

    • Land
    • 15,246 Sq Ft
    • $5,428,571 per Acre

    4838 Higel Ave, Sarasota, FL 34242

    Short Sale. Lot currently has slab in place but building stopped. Plans could be taken over and completed and build your own dream home on Siesta Key. Short walk to the village and all it has to offer. Pics are the rendering of the permitted house to be built.

    Troy Jenkins REALTY EXECUTIVES GALLERY

    4838 Higel Ave, Sarasota, FL 34242
  • /91

    $1,599,999

    $195K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,788 Sq Ft

    5507 Contento Dr, Sarasota, FL 34242

    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. The heated pool and panoramic pool cage

    Livya Hament PREFERRED SHORE LLC

    5507 Contento Dr, Sarasota, FL 34242
  • /48

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 2,244 Sq Ft

    5143 Sandy Beach Ave, Sarasota, FL 34242

    Just bring your wardrobe! Welcome to this beautifully updated and fully furnished and equipped 4-bedroom, 3-bath cottage-style home in one of Siesta Key’s most sought-after neighborhoods - just a short stroll to public beach access at top-rated Siesta Key Beach. Meticulously renovated in 2025, this true turnkey entertainer's paradise offers a vacation-every-day lifestyle complete with thoughtful

    Hannah Thorn VREELAND REAL ESTATE LLC

    5143 Sandy Beach Ave, Sarasota, FL 34242

Home Price Trends

Median Sale Price
$2,680,000
Median Single Family Sale Price
$3,250,000
Median 2 Bedroom Sale Price
$605,000
Average Price Per Sq Ft
$831
Number of Homes for Sale
4
Last 12 months Home Sales
7
Months of Supply
6.90
Median List Price
$3,250,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
3%
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