Siesta Key, FL Homes

/27
$989,000
- 3 Beds
- 1 Bath
- 1,240 Sq Ft
5026 Calle Minorga, Siesta Key, FL 34242

RARE OPPORTUNITY IN SIESTA KEY VILLAGE! This charming cottage-style property is ideally located in the heart of Siesta Key Village, just steps from world-renowned Siesta Beach, boutique shopping, and vibrant dining. Zoned OPI (Office, Professional, Institutional), this versatile property offers endless potential for professional office use, boutique business, or residential conversion (buyer to

Kim Donahue

MEDWAY REALTY

(941) 395-0691

5026 Calle Minorga, Siesta Key, FL 34242
/36
$7,500 Per Month
- 1 Bed
- 1 Bath
- 728 Sq Ft
- Condo for Rent
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

Robert Bevington SHOWTIME REALTY

5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
/2
$1,525,000 Sold May 07, 2026

312 Canal Rd, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 1,792 Sq Ft
- Built 1986
Last Sold Summary
- 20% Below List Price
- $851/SF
- 11 Days On Market
Current Estimated Value $1,617,287

Last Listing Agent Curtis Ware KW COASTAL LIVING III

312 Canal Rd, Sarasota, FL 34242

/2
Est $903,172 Not Listed For Sale

6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
- Built 1980
6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242

Last Sold Summary
- 6% Above List Price
- $548/SF
- 1 Day On Market
- Last Sold Price $850,000
- May 01, 2025
Last Listing Agent Jeff Bray LPT REALTY, LLC

/35
$719,000
- 2 Beds
- 2 Baths
- 1,463 Sq Ft
1200 E Peppertree Ln Unit 302, Sarasota, FL 34242

PRICE IMPROVEMENT OF $20.000!! Turnkey coastal living in the desirable mid-rise tower at Peppertree Bay on Siesta Key. This sought-after split-plan residence offers bright open living spaces, exceptional privacy, and the convenience of effortless island living with resort-style Gulf-to-Bay amenities just moments from world-famous Siesta Beach. Offered fully turnkey furnished, this beautifully

Renee Nadiv

WILLIAM RAVEIS REAL ESTATE

(941) 421-5862

1200 E Peppertree Ln Unit 302, Sarasota, FL 34242
/34
$3,500

Total Monthly Price
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1300 N Portofino Dr Unit 205, Siesta Key, FL 34242

Welcome to your newly renovated dream coastal escape in beautiful Siesta Harbor on Siesta Key, Sarasota, Florida, USA! This turnkey furnished; spacious one-bedroom, two-bath condo featuring brand new furniture is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short 5-minute stroll, you'll enjoy

1300 N Portofino Dr Unit 205, Siesta Key, FL 34242
/2
$650,000 Sold Mar 31, 2026

4660 Ocean Blvd Unit E2, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1971
Last Sold Summary
- 1% Below List Price
- $542/SF
- 25 Days On Market
Current Estimated Value $653,049

Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

4660 Ocean Blvd Unit E2, Sarasota, FL 34242

/2
Est $334,576 Not Listed For Sale

5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 797 Sq Ft
- Built 1975
5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242

Last Sold Summary
- 10% Above List Price
- $381/SF
- 45 Days On Market
- Last Sold Price $303,500
- Apr 28, 2025
Last Listing Agent Mary Jo Violett Michael Saunders

/55
$374,900
- 1 Bed
- 2 Baths
- 780 Sq Ft
1350 N Portofino Dr Unit 107, Sarasota, FL 34242

SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly IDILYING By and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat at your home! BUT WAIT till you see this TOTALLY RENOVATED BEAUTIFUL 1 bedroom 2 full bathroom condo! NEW, NEW, NEW...everything is new...Ceramic tile flooring, baseboards, interior doors &

Scotty Ledford

VUE REALTY, LLC

(941) 207-7524

1350 N Portofino Dr Unit 107, Sarasota, FL 34242
/18
$5,970 Per Month
- 1 Bed
- 1 Bath
- 696 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242

This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. 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 12, 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 $2,261,247

Last Listing Agent Anthony Dalesandro BRIGHT REALTY

1241 Big Oak Ln, Sarasota, FL 34242

/42
Est $848,996 Not Listed For Sale

5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 720 Sq Ft
- Built 1970
5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242

Last Sold Summary
- 13% Below List Price
- $1,354/SF
- 0 Days On Market
- Last Sold Price $975,000
- May 08, 2023
Last Listing Agent Rudy Dudon Michael Saunders

/85
$1,500,000
- 4 Beds
- 3 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 vacation rental, or a full-time residence, this property checks all the boxes. The interior style will delight those who love mid-century modern decor! The home’s unique floor plan is flooded with natural light, creating a bright, inviting

Carla Rayman Kidd

COLDWELL BANKER REALTY

(941) 239-2641

746 Plymouth St, Sarasota, FL 34242
/15
$1,695 Per Month
- 1 Bed
- 1 Bath
- 340 Sq Ft
- Condo for Rent
5215 Calle de Costa Rica Unit C, Siesta Key, FL 34242

5215 Calle de Costa Rica Unit C, Siesta Key, 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 $1,434,890

Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

4108 Roberts Point Rd, Sarasota, FL 34242

/50
Est $4,824,154 Not Listed For Sale

3954 Roberts Point Rd, Sarasota, FL 34242
- 5 Beds
- 5 Baths
- 4,214 Sq Ft
- Built 2014
3954 Roberts Point Rd, Sarasota, FL 34242

Last Sold Summary
- 12% Below List Price
- $1,305/SF
- 9 Days On Market
- Last Sold Price $5,499,000
- Nov 29, 2023
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

/54
$80,000
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
915 Seaside Dr Unit 312, Weeks 8-9, Sarasota, FL 34242

Fractional Ownership. Introducing the Winter Fractional Package, offering 1/16th ownership in a stunning luxury residence on Siesta Key Beach. Now, your dream of owning a beachfront home on America's most celebrated shore can become a reality. Enjoy the benefits of owning a slice of paradise, complete with world-class amenities and services. This exclusive opportunity offers the ultimate in

Kelly Mooney

DOUGLAS ELLIMAN

(941) 389-0934

915 Seaside Dr Unit 312, Weeks 8-9, Sarasota, FL 34242
/80
$8,500 Per Month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- House for Rent
5216 Calle de Costa Rica, Sarasota, FL 34242

Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key

Beth Dilley ASCENDIA REAL ESTATE

5216 Calle de Costa Rica, Sarasota, FL 34242
/2
$1,113,000 Sold May 06, 2026

5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,285 Sq Ft
- Built 1976
Last Sold Summary
- 13% Below List Price
- $866/SF
- 126 Days On Market
Current Estimated Value $1,214,684

Last Listing Agent Beverly Schroeder PLUMLEE GULF BEACH REALTY

5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242

/60
Est $7,708,843 Not Listed For Sale

5131 Jungle Plum Rd, Sarasota, FL 34242
- 6 Beds
- 6.5 Baths
- 6,369 Sq Ft
- Built 2001
5131 Jungle Plum Rd, Sarasota, FL 34242

Last Sold Summary
- 17% Below List Price
- $1,465/SF
- 252 Days On Market
- Last Sold Price $9,330,000
- Dec 04, 2023
Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

/53
$59,000
- 3 Beds
- 3 Baths
- 2,255 Sq Ft
915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242

Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

Kelly Mooney

DOUGLAS ELLIMAN

(941) 352-4595

915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242
/42
Call for Price
- 1 Bed
- 1 Bath
- 820 Sq Ft
- Condo for Rent
797 Beach Rd Unit 305, Sarasota, FL 34242

Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and

797 Beach Rd Unit 305, 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 $1,104,908

Last Listing Agent Christopher Grant GRANT TEAM REAL ESTATE, LLC

5239 Siesta Cove Dr, Sarasota, FL 34242

/2
Est $7,628,305 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
- Feb 27, 2025
Last Listing Agent Tammy Dentici BRIGHT REALTY

/24
$575,000
- 1 Bed
- 1 Bath
- 600 Sq Ft
6006 Midnight Pass Rd Unit 51, Sarasota, FL 34242

PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an

Daniel Hut

HUT REALTY, LLC

(941) 292-7027

6006 Midnight Pass Rd Unit 51, Sarasota, FL 34242
/54
$9,500 Per Month
- 3 Beds
- 2 Baths
- 1,835 Sq Ft
- Condo for Rent
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

Andy Moore GULF COAST REALTY & MANAGEMENT

1389 Siesta Bayside Dr Unit 1389F, 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 $735,994

Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY

1055 Beach Rd Unit B204, Sarasota, FL 34242

/2
Est $696,361 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
- Dec 18, 2024
Last Listing Agent Rudy Dudon Michael Saunders

/52
$584,500
- 2 Beds
- 2 Baths
- 1,287 Sq Ft
6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242

Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor

Anthony DeLuca

DELUCA REALTY INC

(941) 419-2073

6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242
/58
$3,300 Per Month
- 2 Beds
- 2 Baths
- 1,435 Sq Ft
- Annual UNfurnished Siesta Key Gulf front 2/2 condo with water views!
4822 Ocean Blvd, 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

4822 Ocean Blvd, 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 $691,016

Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

101 Whispering Sands Dr Unit 307, 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
- Nov 13, 2024
Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

/60
$1,995,000
- 4 Beds
- 3.5 Baths
- 2,971 Sq Ft
116 Garden Ln, Sarasota, FL 34242

Effortless Island Living on Siesta Key’s Coveted North End.Discover the perfect blend of modern luxury and low-maintenance living in thiscontemporary coastal retreat, ideally located on the quiet North End of Siesta Key.Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortlessproximity to Siesta Village, the North Bridge, and downtown Sarasota.Built in

Gerard Healy

WILLIAM RAVEIS REAL ESTATE

(941) 337-4899

116 Garden Ln, 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
$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 $683,961

Last Listing Agent Marci McFarland MICHAEL SAUNDERS & COMPANY

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/72
Est $652,380 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
- 5% Below List Price
- $539/SF
- 1 Day On Market
- Last Sold Price $685,000
- Aug 25, 2023
Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

/79
$1,725,000
- 3 Beds
- 3.5 Baths
- 2,080 Sq Ft
548 Beach Rd Unit A540, Sarasota, FL 34242

This beautifully renovated Tiffany Sands townhome on Siesta Key offers the perfect blend of space, style, and an unbeatable location with serene beach views. Featuring 3 bedrooms and 3.5 baths, the open and inviting floor plan is designed for both comfort and effortless coastal living, with each spacious bedroom offering its own walk-in closet. A versatile first-floor bonus room, complete with a

Jennifer Thompson

WILLIAM RAVEIS REAL ESTATE

(941) 265-8533

548 Beach Rd Unit A540, Sarasota, FL 34242
/19
$2,200 Per Month
- 1 Bed
- 1 Bath
- 656 Sq Ft
- 1 Bedroom 1 Bath Condo Sandy Cove II Short Term Rental/Annual Rental
111 Pass Key Rd, Siesta Key, FL 34242

Available off season till 10/31/26 for $2200 per month!!! Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ

111 Pass Key Rd, Siesta Key, FL 34242
/2
$2,850,000 Sold Apr 17, 2026

4651 Higel Ave, Sarasota, FL 34242
- 4 Beds
- 3 Baths
- 3,500 Sq Ft
- Built 2007
Last Sold Summary
- 5% Below List Price
- $814/SF
- 0 Days On Market
Current Estimated Value $2,871,751

Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

4651 Higel Ave, Sarasota, FL 34242

/36
Est $853,363 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
- 5% Below List Price
- $523/SF
- 57 Days On Market
- Last Sold Price $900,000
- May 08, 2024
Last Listing Agent Peter Lev EXCEPTIONS 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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