Siesta Key, FL Homes

/94
$948,000
- 3 Beds
- 2 Baths
- 2,255 Sq Ft
635 Tropical Cir, Sarasota, FL 34242

Discover luxurious coastal living on tropical Siesta Key, #1 beach in the US and #4 in the world! Set on an elevated lot that sustained NO storm damage, includes a NEW TAMKO hurricane proof ROOF with transferable workmanship warranty, new gutters, oversized side-entry 2-car garage, and circular driveway surrounded by lush tropical landscaping. Currently being used as an income producing home

Tami Cashi

COLDWELL BANKER REALTY

(941) 273-8651

635 Tropical Cir, Sarasota, FL 34242
/54
$3,300 per month
- 2 Beds
- 2 Baths
- 1,435 Sq Ft
- Condo for Rent
4822 Ocean Blvd Unit 5F, Sarasota, FL 34242

Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass

Cody Smith RENT SARASOTA

4822 Ocean Blvd Unit 5F, Sarasota, FL 34242
/2
$2,250,000 Sold Jun 03, 2025

1241 Big Oak Ln, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,848 Sq Ft
- Built 1979
Last Sold Summary
- 13% Below List Price
- $1,218/SF
- 49 Days On Market
Current Estimated Value $2,240,910

Last Listing Agent Anthony Dalesandro BRIGHT REALTY

1241 Big Oak Ln, Sarasota, FL 34242

/2
Est $7,614,556 Not Listed For Sale

3960 Roberts Point Rd, Sarasota, FL 34242
- 4 Beds
- 7 Baths
- 5,282 Sq Ft
- Built 2024
3960 Roberts Point Rd, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $1,534/SF
- 145 Days On Market
Last Sold Price $8,100,000

Last Listing Agent Tammy Dentici BRIGHT REALTY

/46
$1,250,000
- 3 Beds
- 4 Baths
- 3,050 Sq Ft
5324 Siesta Ct, Sarasota, FL 34242

In a market where location defines value, this contemporary residence in Siesta Cove delivers on every level. Positioned on more than a quarter-acre just minutes from Siesta Key Beach and Siesta Key Village, the property pairs architectural character with rare privacy and scale. Equally important, it offers something increasingly essential in coastal real estate: confidence. The property has

Renee Nadiv

WILLIAM RAVEIS REAL ESTATE

(941) 401-1686

5324 Siesta Ct, Sarasota, FL 34242
/49
$5,000 per month
- 2 Beds
- 2 Baths
- 1,389 Sq Ft
- Condo for Rent
1355 S Portofino Dr Unit 103, Sarasota, FL 34242

Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points.This

Alison Kanter DANIELLE GLADDING & CO. REALTY

1355 S Portofino Dr Unit 103, Sarasota, FL 34242
/2
$1,450,000 Sold Nov 04, 2025

4108 Roberts Point Rd, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 2,511 Sq Ft
- Built 2001
Last Sold Summary
- 23% Below List Price
- $577/SF
- 142 Days On Market
Current Estimated Value $1,423,202

Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

4108 Roberts Point Rd, Sarasota, FL 34242

/2
Est $692,078 Not Listed For Sale

5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- Built 1974
5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $672/SF
- 1 Day On Market
Last Sold Price $739,500

Last Listing Agent Rudy Dudon Michael Saunders

/24
$349,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242

PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene

Jim Gammello

WILLIAM RAVEIS REAL ESTATE

(941) 207-9258

5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242
/90
$6,000 per month
- 3 Beds
- 2 Baths
- 2,295 Sq Ft
- House for Rent
5310 Hidden Harbor Rd, Sarasota, FL 34242

Siesta Key Annual rental. Located just a half mile from Siesta Key Beach, this four-bedroom, two-bath home is tucked away in the quiet Hidden Harbor area. Set in a beautiful tropical environment with canopy-lined streets, the property features 2,300 square feet of living space and a 1200-square-foot lanai.The interior offers an open floor plan with vaulted ceilings, skylights, and updated

Margaret Young JENNETTE PROPERTIES, INC.

5310 Hidden Harbor Rd, Sarasota, FL 34242
/2
$520,000 Sold Mar 26, 2025

1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 975 Sq Ft
- Built 1974
Last Sold Summary
- 19% Below List Price
- $533/SF
- 36 Days On Market
Current Estimated Value $513,289

Last Listing Agent Marc Rasmussen CORCORAN DWELLINGS REALTY

1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

/62
Est $604,909 Not Listed For Sale

5600 Beach Way Dr Unit 101, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,359 Sq Ft
- Built 1970
5600 Beach Way Dr Unit 101, Sarasota, FL 34242

Last Sold Summary
- 12% Below List Price
- $504/SF
- 5 Days On Market
Last Sold Price $685,000

Last Listing Agent Michael Bridges RE/MAX

/53
$475,000
- 1 Bed
- 1 Bath
- 845 Sq Ft
1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your

Jessica Ross, PA

COLDWELL BANKER REALTY

(941) 292-2778

1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
/13
$6,972 per month
- 1 Bed
- 1 Bath
- 672 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242

New photos coming soon! Villa 36 at Aloha Kai is perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
/2
$1,100,000 Sold Jun 16, 2025

5239 Siesta Cove Dr, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 2,333 Sq Ft
- Built 1983
Last Sold Summary
- 20% Below List Price
- $471/SF
- 86 Days On Market
Current Estimated Value $1,105,234

Last Listing Agent Christopher Grant GRANT TEAM REAL ESTATE, LLC

5239 Siesta Cove Dr, Sarasota, FL 34242

/2
Not Listed For Sale

5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1974
5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242

Last Sold Summary
- 3% Below List Price
- $600/SF
- 1 Day On Market
Last Sold Price $600,000

Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

/83
$1,995,000 Open Thu 1PM - 3PM
- 4 Beds
- 3 Baths
- 2,657 Sq Ft
4817 Ocean Blvd, Sarasota, FL 34242

Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart ofSiesta KeySet on a tranquil spring-fed lake just moments from Siesta Beach and the Village, thisflood resilient and meticulously maintained coastal residence offers year-roundenjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, itblends timeless coastal style with

Gerard Healy

WILLIAM RAVEIS REAL ESTATE

(941) 541-8336

4817 Ocean Blvd, Sarasota, FL 34242
/13
$8,970 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 61, Sarasota, FL 34242

Villa 61 at Aloha Kai warmly welcomes you with its cheerful coastal décor, designed to help you forget your worries and simply be happy. Its casual, comfortable style will make you feel right at home, while offering the luxury of both beach and pool access—you’ll just have to decide which you prefer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 61, Sarasota, FL 34242
/2
$735,000 Sold Nov 27, 2025

1055 Beach Rd Unit B204, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
- Built 1981
Last Sold Summary
- 5% Below List Price
- $610/SF
- 29 Days On Market
Current Estimated Value $724,160

Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY

1055 Beach Rd Unit B204, Sarasota, FL 34242

/72
Est $609,584 Not Listed For Sale

101 Whispering Sands Dr Unit 206, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
- Built 1969
101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

Last Sold Summary
- 11% Below List Price
- $539/SF
- 1 Day On Market
Last Sold Price $685,000

Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

/10
$899,000 Pending
- 2 Beds
- 2 Baths
- 1,069 Sq Ft
5144 Oxford Dr, Sarasota, FL 34242

Under contract-accepting backup offers. Build New or Major Redevelopment Near Siesta Beach. Large lot located just minutes from Siesta Beach in a well-established Sarasota neighborhood close to Siesta Key, shopping, and dining. County records indicate the property includes two platted lots of record (Lots 9 and 10). The existing structure has sustained significant damage; renovation may be

April Green

DUNCAN REAL ESTATE, INC.

(941) 900-3468

5144 Oxford Dr, Sarasota, FL 34242
/28
$7,050 per month
- 2 Beds
- 2 Baths
- 1,105 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
/2
$580,000 Sold Mar 13, 2026

101 Whispering Sands Dr Unit 307, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
- Built 1969
Last Sold Summary
- 19% Below List Price
- $456/SF
- 261 Days On Market
Current Estimated Value $650,071

Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

101 Whispering Sands Dr Unit 307, Sarasota, FL 34242

/36
Est $841,937 Not Listed For Sale

1600 Cove II Place Unit 420, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
- Built 1979
1600 Cove II Place Unit 420, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $523/SF
- 57 Days On Market
Last Sold Price $900,000

Last Listing Agent Peter Lev EXCEPTIONS REALTY

/52
$75,000
- 3 Beds
- 3 Baths
- 1,780 Sq Ft
915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242

Fractional Ownership. Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an

Kelly Mooney

DOUGLAS ELLIMAN

(941) 279-2172

915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242
/16
$7,470 per month
- 1 Bed
- 1 Bath
- 572 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242

Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
/2
$692,000 Sold Oct 06, 2025

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,387 Sq Ft
- Built 1981
Last Sold Summary
- 13% Below List Price
- $499/SF
- 165 Days On Market
Current Estimated Value $678,902

Last Listing Agent Marci McFarland MICHAEL SAUNDERS & COMPANY

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/35
Est $1,995,861 Not Listed For Sale

6900 Bochi Cir, Sarasota, FL 34242
- 4 Beds
- 4.5 Baths
- 3,774 Sq Ft
- Built 2012
6900 Bochi Cir, Sarasota, FL 34242

Last Sold Summary
- 4% Above List Price
- $510/SF
- 242 Days On Market
Last Sold Price $1,925,000

Last Listing Agent Malia Smiley KELLY RIGHT REAL ESTATE

/13
$6,400,000
- 8 Beds
- 8.5 Baths
- 5,313 Sq Ft
5610 Avenida Del Mare, Sarasota, FL 34242

Prime Siesta Key investment opportunity or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence.

Tonna Gruber

COLDWELL BANKER REALTY

(941) 841-7869

5610 Avenida Del Mare, Sarasota, FL 34242
/31
$8,900 per month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 302AA, Sarasota, FL 34242

Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a Gulfside Highrise building on the 3rd floor. The kitchen has been renovated with stainless steel appliances and is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig. The master bedroom

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1055 W Peppertree Dr Unit 302AA, Sarasota, FL 34242
/2
$645,000 Sold Jun 17, 2025

6415 Midnight Pass Rd Unit 710, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
- Built 1975
Last Sold Summary
- 1% Below List Price
- $500/SF
- 3 Days On Market
Current Estimated Value $638,722

Last Listing Agent Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

6415 Midnight Pass Rd Unit 710, Sarasota, FL 34242

/47
Est $823,275 Not Listed For Sale

1321 Dockside Place, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,307 Sq Ft
- Built 1982
1321 Dockside Place, Sarasota, FL 34242

Last Sold Summary
- 9% Below List Price
- $692/SF
- 3 Days On Market
Last Sold Price $905,000

Last Listing Agent Tyler Shanahan COLDWELL BANKER REALTY

/82
$330,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
5641 Midnight Pass Rd Unit 902, Sarasota, FL 34242

PRICE IMPROVEMENT: Affordable, Pet-Friendly Siesta Key Beach Condo Now Offered at $330,000 Experience the allure of coastal living at White Sands Village, ideally located along Midnight Pass Road on stunning Siesta Key. This beautifully furnished one-bedroom, one-bathroom residence is just a short walk from the world-famous Siesta Key Public Beach, making it an exceptional opportunity for beach

Jim Gammello

WILLIAM RAVEIS REAL ESTATE

(941) 206-4956

5641 Midnight Pass Rd Unit 902, Sarasota, FL 34242
/31
$7,500 per month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242

Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The condo is in a Gulf-side High-rise building on the 5th floor. Assigned covered parking located in the parking garage under the building.A luxurious dining area greets you as you enter, that flows through to the living room and out to the lanai. The lanai works as an extended living

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
/2
$3,270,000 Sold Apr 01, 2025

77 Sandy Hook Rd N, Sarasota, FL 34242
- 2 Beds
- 2.5 Baths
- 2,627 Sq Ft
- Built 1966
Last Sold Summary
- 14% Below List Price
- $1,245/SF
- 75 Days On Market
Current Estimated Value $3,217,368

Last Listing Agent Daniel Shattuck FLORIDA REALTY INVESTMENTS

77 Sandy Hook Rd N, Sarasota, FL 34242

/2
Est $6,798,989 Not Listed For Sale

1250 Hidden Harbor Way, Sarasota, FL 34242
- 5 Beds
- 5.5 Baths
- 7,506 Sq Ft
- Built 2002
1250 Hidden Harbor Way, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $966/SF
- 502 Days On Market
Last Sold Price $7,250,000

Last Listing Agent Kim Ogilvie Michael Saunders

/44
$115,000
- 3 Beds
- 3 Baths
- 1,900 Sq Ft
915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242

Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 4-7), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on America’s

Kelly Mooney

DOUGLAS ELLIMAN

(941) 842-0963

915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242
/24
$8,500 per month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 606AA, Sarasota, FL 34242

his condo is in a Gulf-side High-rise on the 6th floor, approximately 75 yards from Crescent Beach.A beautiful remodeled kitchen awaits you with stainless steel appliances, granite counter tops and recessed lighting. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker.The formal dining area has seating for 6 and

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1055 W Peppertree Dr Unit 606AA, Sarasota, FL 34242
/2
$1,400,000 Sold Dec 18, 2025

4865 Featherbed Ln, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 4,482 Sq Ft
- Built 1955
Last Sold Summary
- 26% Below List Price
- $312/SF
- 348 Days On Market
Current Estimated Value $1,562,838

Last Listing Agent Janet Boyden PREMIER SOTHEBY'S INTERNATIONAL REALTY

4865 Featherbed Ln, Sarasota, FL 34242

/72
Est $1,349,067 Not Listed For Sale

22 Sandy Cove Rd Unit 502, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 1,876 Sq Ft
- Built 1969
22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

Last Sold Summary
- 16% Below List Price
- $853/SF
- 360 Days On Market
Last Sold Price $1,600,000

Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

Showing Results 41 - 80, Page 2 of 18

Florida Sarasota County Siesta Key

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Siesta Key, FL Homes

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