Siesta Key, FL Homes

/44
$640,000
- 2 Beds
- 2 Baths
- 1,575 Sq Ft
1345 Moonmist Dr Unit T6, Sarasota, FL 34242

Welcome to your dream villa! This spacious coastal villa retreat on Siesta Key boasts 2-bedrooms and 2-bathrooms and offers 1,575 square feet of comfortable, open-concept living space, perfect for both relaxing and entertaining. Step inside to a freshly painted interior featuring a modern, neutral palette that complements any decor. This wonderful detached-villa is in a serene location just

Dean Hall WATERSIDE REALTY LLC

1345 Moonmist Dr Unit T6, Sarasota, FL 34242
/18
$7,700 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops

Andy Moore GULF COAST REALTY & MANAGEMENT

1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
/2
$570,000 Sold Aug 01, 2025

5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1976
Last Sold Summary
- 12% Below List Price
- $495/SF
- 59 Days On Market
Current Estimated Value $564,865

Last Listing Agent Christine Green COLDWELL BANKER REALTY

5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

/2
Est $540,680 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
5600 Beach Way Dr Unit 107, Sarasota, FL 34242

5600 Beach Way Dr Unit 107, Sarasota, FL 34242

/47
$724,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
4900 Ocean Blvd Unit 201, Sarasota, FL 34242

Enjoy coastal living in this updated 2-bedroom, 2-bath Siesta Key condo, just minutes from Siesta Key Village and the beach. The second-floor residence features a fresh coastal design and a kitchen remodeled in 2020 with granite countertops, stainless-steel appliances, and a washer/dryer. Natural light fills the space through large sliders that open to two spacious lanais with peaceful water and

David Broecker PINPOINT REALTY GROUP LLC

4900 Ocean Blvd Unit 201, Sarasota, FL 34242
/89
$4,700 per month
- 3 Beds
- 3 Baths
- 1,867 Sq Ft
- Condo for Rent
4900 Ocean Blvd Unit 501, Sarasota, FL 34242

Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the

Beth Dilley ASCENDIA REAL ESTATE

4900 Ocean Blvd Unit 501, Sarasota, FL 34242
/2
$550,000 Sold Nov 12, 2025

5222 Winding Way, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
- Built 1963
Last Sold Summary
- 3% Below List Price
- $484/SF
- 35 Days On Market
Last Listing Agent Robert Moffatt MICHAEL SAUNDERS & COMPANY

5222 Winding Way, Sarasota, FL 34242

/72
Est $5,006,960 Not Listed For Sale
- 4 Beds
- 4 Baths
- 4,131 Sq Ft
5119 Jungle Plum Rd, Sarasota, FL 34242

5119 Jungle Plum Rd, Sarasota, FL 34242

/28
$659,000
- 2 Beds
- 2 Baths
- 1,025 Sq Ft
145 Avenida Messina Unit 3, Sarasota, FL 34242

Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic

Joe Cleary RE/MAX ALLIANCE GROUP

145 Avenida Messina Unit 3, Sarasota, FL 34242
/35
$8,200 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

Andy Moore GULF COAST REALTY & MANAGEMENT

1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
/2
$1,150,000 Sold Oct 22, 2025

4915 Primrose Path, Sarasota, FL 34242
- 6 Beds
- 5 Baths
- 3,549 Sq Ft
- Built 1960
Last Sold Summary
- 38% Below List Price
- $324/SF
- 320 Days On Market
Last Listing Agent Tony Andrews ANDREWS & ASSOCIATES REALTY

4915 Primrose Path, Sarasota, FL 34242

/45
Est $1,450,279 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
313 Beach Rd Unit 313S1, Sarasota, FL 34242

313 Beach Rd Unit 313S1, Sarasota, FL 34242

/42
$1,200,000
- 2 Beds
- 2 Baths
- 1,840 Sq Ft
1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242

Experience Unparalleled Bayfront Living at Dolphin Bay on Siesta Key! Enjoy one of the most breathtaking views on Siesta Key with unobstructed, direct water views of the Bay and Intracoastal from your spacious enclosed lanai, complete with impact glass doors. Start your mornings with coffee on your private brick patio overlooking the water, which leads directly to the community dock and fishing

Tony Andrews ANDREWS & ASSOCIATES REALTY

1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
/27
$6,300 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

Andy Moore GULF COAST REALTY & MANAGEMENT

1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
/2
$850,000 Sold Jun 05, 2025

5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,471 Sq Ft
- Built 1984
Last Sold Summary
- 17% Below List Price
- $578/SF
- 165 Days On Market
Current Estimated Value $915,977

Last Listing Agent Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242

/100
Est $7,863,085 Not Listed For Sale
- 6 Beds
- 9 Baths
- 8,615 Sq Ft
4300 Higel Ave, Sarasota, FL 34242

4300 Higel Ave, Sarasota, FL 34242

/27
$950,000
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
315 Avenida de Paradisio, Sarasota, FL 34242

Bring your hammer! If you want a house on the water with rock solid bones and a great floorplan this is probably it. 1/4 acre lot, nice covered lanai, walking distance to the Village and beach just beyond that. House has brand new plumbing, windows and roof only a couple years old, ready to be put back together. Can be purchased in tandem with 307 Avenida if you want to start fresh and combined

Jason Skowronski COMPASS FLORIDA LLC

315 Avenida de Paradisio, 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
$1,200,000 Sold May 07, 2025

822 Paradise Way, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 1,517 Sq Ft
- Built 1962
Last Sold Summary
- 8% Below List Price
- $791/SF
- 14 Days On Market
Current Estimated Value $1,170,853

Last Listing Agent Sue Ann Levin COLDWELL BANKER REALTY

822 Paradise Way, Sarasota, FL 34242

/81
Est $6,424,193 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 7,003 Sq Ft
4205 Higel Ave, Sarasota, FL 34242

4205 Higel Ave, Sarasota, FL 34242

/50
$2,500,000
- 3 Beds
- 3.5 Baths
- 2,468 Sq Ft
5024 Commonwealth Dr, Sarasota, FL 34242

Nestled in the quaint neighborhood along the Grand Canal on Siesta Key, this Key West style home offers the perfect blend of old-world charm and modern living. This exceptionally well-appointed custom-built home is being offered turnkey. The home's grand entrance welcomes you through a covered porch that leads to an oversized foyer. You are greeted with a spectacular open floor plan, where an

Gabi Charity CHARITY & WEISS INTERNATIONAL LLC

5024 Commonwealth Dr, Sarasota, FL 34242
/35
$7,400 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

Andy Moore GULF COAST REALTY & MANAGEMENT

1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
/2
$2,350,000 Sold Jan 09, 2025

5740 Midnight Pass Rd Unit 506, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 1986
Last Sold Summary
- 9% Below List Price
- $1,173/SF
- 10 Days On Market
Current Estimated Value $2,076,791

Last Listing Agent Tina Johns COLDWELL BANKER REALTY

5740 Midnight Pass Rd Unit 506, Sarasota, FL 34242

/2
Est $1,830,102 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
3928 Roberts Point Rd, Sarasota, FL 34242

3928 Roberts Point Rd, Sarasota, FL 34242

/37
$6,000,000
- 5 Beds
- 7 Baths
- 4,496 Sq Ft
5507 Calle Del Invierno, Sarasota, FL 34242

There is only one – The Lookout. Effortlessly close to everything yet a world apart, this modern Siesta Key estate embodies the essence of the Vunique Homes experience—architectural artistry, intentional design, and a lifestyle defined by luxury and ease. Steps from Siesta Key Beach and the vibrant Siesta Village, this turnkey furnished residence is ideally positioned for those who value

Rudy Dudon MICHAEL SAUNDERS & COMPANY

5507 Calle Del Invierno, Sarasota, FL 34242
/36
$9,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242

Welcome to your elevated sanctuary in paradise – a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-concept living space that seamlessly integrates the interior with the scenic beauty beyond. The living area, adorned with coastal-inspired décor, invites you to relax in comfort while large

Andy Moore GULF COAST REALTY & MANAGEMENT

1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
/2
$910,000 Sold Apr 22, 2025

5300 Ocean Blvd Unit 803, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,375 Sq Ft
- Built 1973
Last Sold Summary
- 37% Below List Price
- $662/SF
- 267 Days On Market
Current Estimated Value $936,569

Last Listing Agent Diane Goodwin EXP REALTY LLC

5300 Ocean Blvd Unit 803, Sarasota, FL 34242

/68
Est $530,532 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

/61
$2,690,000
- 4 Beds
- 3.5 Baths
- 3,228 Sq Ft
467 Canal Rd Unit 467, Sarasota, FL 34242

Possible Seller Finance. High & Dry!! BEACH, BOATING & BISTROS!!!! SIESTA KEY`CANAL FRONT featuring WEEKLY RENTALS!! DOCK & LIFT!! GULF VIEWS!! BEACH ACCESS STEPS AWAY!!! Great location with Gulf Views steps to Public Beach Access #8 offering the ultimate waterfront lifestyle of this rare, furnished 3 bedroom/3.5 Bath plus office (or 4th bedroom), RMF-zoned opportunity on Siesta Key. Built in

Dan Miller PREFERRED SHORE LLC

467 Canal Rd Unit 467, Sarasota, FL 34242
/41
$7,600 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

Andy Moore GULF COAST REALTY & MANAGEMENT

1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
/2
$625,000 Sold Oct 24, 2025

199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,557 Sq Ft
- Built 1970
Last Sold Summary
- 8% Below List Price
- $401/SF
- 62 Days On Market
Last Listing Agent Tracy Srodes FINE PROPERTIES

199 Whispering Sands Dr Unit 105, Sarasota, FL 34242

/26
Est $517,643 Not Listed For Sale
- 1 Bed
- 1 Bath
- 728 Sq Ft
6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

/80
$6,000,000 Pending
- 4 Beds
- 3.5 Baths
- 3,446 Sq Ft
251 Cedar Park Cir, Sarasota, FL 34242

Under contract-accepting backup offers. This award-winning Modernist home was designed to provide privacy while maintaining direct tranquil water views framed by mature tropical landscaping. In the desired and private lot enclave of Cedar Park, one approaches the residence via a canopied private lane before entering the ideal spot for boaters, car enthusiasts, or those who just enjoy the serenity

Steve Wexler PREMIER SOTHEBY'S INTERNATIONAL REALTY

251 Cedar Park Cir, Sarasota, FL 34242
/30
$7,700 per month
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
- Condo for Rent
1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242

A spacious two bedroom/two bath ground floor home with attached garage. Relax on the private south-facing lanai overlooking a lake featuring a fountain and frequent visits by numerous water birds. After a long day enjoy HDTV and high-speed internet ready to stream your favorite programs. Wireless internet is also available throughout Bayside and at the pools. The living area is tiled, and the

Andy Moore GULF COAST REALTY & MANAGEMENT

1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
/2
$482,500 Sold Jun 06, 2025

5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Built 1975
Last Sold Summary
- 3% Below List Price
- $477/SF
- 7 Days On Market
Current Estimated Value $462,633

Last Listing Agent Linda Williams GULF SHORES REALTY

5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

/2
Est $481,002 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

/99
$690,000
- 1 Bed
- 1 Bath
- 816 Sq Ft
797 Beach Rd Unit 509, Sarasota, FL 34242

PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional

Sandy Gamble Hulvat WATERSIDE REALTY LLC

797 Beach Rd Unit 509, Sarasota, FL 34242
/24
$4,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242

Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when

Andy Moore GULF COAST REALTY & MANAGEMENT

1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
/2
$860,000 Sold Oct 03, 2025

1055 Beach Rd Unit B302, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
- Built 1981
Last Sold Summary
- 7% Below List Price
- $714/SF
- 262 Days On Market
Last Listing Agent Michele Tanner PREFERRED SHORE LLC

1055 Beach Rd Unit B302, Sarasota, FL 34242

/52
Est $496,138 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

Showing Results 281 - 320, Page 8 of 18

Florida Sarasota County Siesta Key

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage