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SIESTA KEY | Southwest FL Real Estate
Siesta Key Homes - Sarasota, FL
Siesta Key has been voted the #1 beach by Trip Advisor Travelers in 2015! It is reached by 2 bridges from Sarasota and has 4 distinct areas: Siesta Beach, Crescent Beach, Turtle Beach and Siesta Key Village. It has miles of "the world's finest, whitest sand" and offers fishing, boating, parasailing, kayaking, jet skiing and more. You can find yoga on the beach and live music in the Village. Homes on the island include condominiums, villas and townhouses and single family homes from the $200,000s to over $10,000,000. Let us help you find your "Piece of Beach Paradise"! More information can be found at www.siestakeychamber.com.
Siesta Key | Latest Homes for Sale on Siesta Key
This beautiful 2/2 turnkey furnished condominium is updated and tastefully decorated. New cabinets, tile, counter tops, appliances, electric window treatments, built in d...
- 2 Beds
- 2 Baths
- Gulf & Bay Club SubDv.
- 34242 Zip Code
Boaters alert. This priced to sell 2 bedroom/ 2 bath turnkey furnished unit on Siesta Key has dockage available on sailboat water with direct access to the intercoastal ...
- 2 Beds
- 2 Baths
- Siesta Harbor SubDv.
- 34242 Zip Code
This home is located 10-15 minutes away by walking from the Siesta Key beach. The interior of the home has an updated look, including the beautiful wood burning fireplace...
- 3 Beds
- 2 Baths
- Siesta Cove Sub SubDv.
- 34242 Zip Code
Enjoy the finest of coastal living on Siesta Key. Beautiful views of Little Sarasota Bay and pool greet you as you enter this bright and impeccably maintained one bedroo...
- 1 Beds
- 1 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
LOCATION, DESIGN, QUALITY!!! Completely remodeled gorgeous house on Cul-de-sac at the end of a quiet street, located on Siesta Key close to the bay!!! Beautiful contempo...
- 4 Beds
- 2.5 Baths
- Oyster Cove SubDv.
- 34242 Zip Code
Come and enjoy your new home in paradise in Building 9 at Midnight Cove II. This beautiful first floor unit is just a short walk to the white sands of Crescent Beach. Ste...
- 2 Beds
- 2 Baths
- Midnight Cove Ii SubDv.
- 34242 Zip Code
Whether you are a beach lover, water sports enthusiast or just love the island lifestyle, this home is for you! Located on a quiet section of Siesta Key, this home offers...
- 4 Beds
- 3 Baths
- Sandy Hook SubDv.
- 34242 Zip Code
DEEDED BEACH ACCESS!! Your feet will be in the Gulf of Mexico in 60 seconds!!! This immaculate pool home features large rooms and volume ceilings. Lovely oak floors and s...
- 3 Beds
- 3.5 Baths
- Tortoise Estates SubDv.
- 34242 Zip Code
CAREFREE CONDO LIVING AT IT'S BEST! RELAX ISLAND STYLE ON THE WHITE SANDY BEACH OF SIESTA KEY - ENJOY LIVING ON THE FIRST FLOOR FOR EASY ACCESS TO THE BEACH AND POOL - J...
- 2 Beds
- 2 Baths
- Island Reef SubDv.
- 34242 Zip Code
This BRIGHT & UPDATED 2 Bedroom, 2 Bath, 1365 sq ft, FIRST FLOOR condo includes rarely available 900 sq ft of OUTDOOR LIVING SPACE! Enjoy the beauty of Florida’s indoo...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
On a clear day, you can see forever! Experience AMAZING VIEWS and only the gentle sound of the breaking waves from this sunny 11th floor Gulf front property in the North...
- 2 Beds
- 2 Baths
- Whispering Sands SubDv.
- 34242 Zip Code
Absolutely stunning, one of a kind, THREE BEDROOM condo at the south end of Siesta Key. Enjoy amazing sunrises across the Intrarcoastal waterway and beautiful sunsets ove...
- 3 Beds
- 2 Baths
- Pointe On Midnight Pass SubDv.
- 34242 Zip Code
EXCELSIOR on SIESTA KEY is premier community from bay to beach with fishing pier, two heated pools and spas, three lighted tennis courts, pickle ball courts, grill and pi...
- 2 Beds
- 2 Baths
- Excelsior Beach To Bay SubDv.
- 34242 Zip Code
Enjoy Siesta Key Beach from this top-floor, turnkey furnished, updated condo with 2 bedrooms, 2 baths and open concept floor plan. You’ll love these updates - architectur...
- 2 Beds
- 2 Baths
- Beachway Apts SubDv.
- 34242 Zip Code
Great Gulfside location in Peppertree on Siesta Key. This luxurious condo has been professionally remodeled. The 1055 building is the closest midrise building to the be...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
A “GULF TO BAY” lifestyle is yours in the exclusive gated community of Spice Bay. Stroll across the cul-de-sac to your deeded deep water dock on the Intracoastal, or take...
- 4 Beds
- 4.5 Baths
- Spice Bay SubDv.
- 34242 Zip Code
A MUST SEE, charming, three-bedroom, two-bath home located on a private lake within walking distance of Siesta Key Village. An inviting, spacious, fenced backyard is ador...
- 3 Beds
- 2 Baths
- Ocean Beach SubDv.
- 34242 Zip Code
Paradise Found! The search is over for the most spectacular water views of the Gulf, the Intracoastal Waterway and Blind Pass in this exceptional home! This COMPLETELY ...
- 2 Beds
- 2 Baths
- Pointe On Midnight Pass SubDv.
- 34242 Zip Code
Everything you should be looking for in a rental income property is right here in this super cute, happy little condo! $36,207 in gross rental income for fiscal year 2019...
- 1 Beds
- 1 Baths
- Ebbtide SubDv.
- 34242 Zip Code
Beautifully appointed and freshly renovated 5th Floor Gulf view at Siesta Sands Beach Resort on the southern end of world renowned Crescent Beach. Featuring a captivatin...
- 2 Beds
- 2 Baths
- Siesta Sands Resort (Timeshare) SubDv.
- 34242 Zip Code
Updated Siesta Isles pool home on a HUGE lot under $700k! This 3 bedroom, 3 bathroom home is currently configured as 4 bedroom 3 bath and has been nicely updated with l...
- 4 Beds
- 3 Baths
- Siesta Isles SubDv.
- 34242 Zip Code
Gorgeous panoramic views of Gulf and magnificent sunsets! This true three bedroom, three bath, sixth floor condo is one of the largest units Harbor Towers offers. Experie...
- 3 Beds
- 3 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
This residence is located the closest to the beach in the building, the very Gulf Front stack so act fast on this rare opportunity! With 2 bedrooms and 2 full bathrooms h...
- 2 Beds
- 2 Baths
- House Of The Sun (Was Known As Haleakala) SubDv.
- 34242 Zip Code
This beautiful condo, located in the sought-after Grand Tower of the Palm Bay Club has breathtaking views of the famous Siesta Key Beach from both the bedroom and living ...
- 1 Beds
- 1 Baths
- Palm Bay Club SubDv.
- 34242 Zip Code
Arrive by boat or by car! This home offers breathtaking water views of Blind Pass... of the world famous Siesta Key. Enjoy the million dollar views from this open concep...
- 2 Beds
- 2 Baths
- Moorings SubDv.
- 34242 Zip Code
Peppertree Bay condo. Over 1400 sq/ft of living space includes two bedrooms, 2 bathrooms, spacious living/dining room, large kitchen, laundry/utility room, and enclosed ...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
Discover your piece of island paradise on Siesta Key where this furnished 2015-built residence is an ode to Florida family living. Situated on a canal only three homes fr...
- 4 Beds
- 4 Baths
- Secluded Harbour SubDv.
- 34242 Zip Code
Enjoy resort-style living at Harbor Towers Yacht and Racquet Club, located on Siesta Key! Harbor Towers is a boaters paradise, situated along the Intra-coastal waterway, ...
- 1 Beds
- 1 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
Evoking the feel of an endless beach vacation, this Beachaven villa certainly lives up to its name. Situated on Siesta Beach-named the #1 beach in the nation-this under t...
- 1 Beds
- 1 Baths
- Beachaven SubDv.
- 34242 Zip Code
Upon entering this beautifully updated and meticulously maintained Siesta Key residence you will get a sense of what life on the water is all about. From the moment you ...
- 3 Beds
- 3 Baths
- Siesta Bayside SubDv.
- 34242 Zip Code
With panoramic views of the crystal white sand and the azure waters of the Gulf, this top floor end unit will wow the most discriminating buyer. Totally redone with Subze...
- 2 Beds
- 2 Baths
- Jamaica Royale SubDv.
- 34242 Zip Code
Fantastic income opportunity! Freshly updated with new paint and furniture. Located midway in the garden area, this unit is a 1 bedroom, 1 bath with an in unit Washer/Dr...
- 1 Beds
- 1 Baths
- Jamaica Royale SubDv.
- 34242 Zip Code
FULL WATERFRONT VIEW ON SIESTA KEY! Great INCOME-PRODUCING, remodeled, 2-bedroom condo with FIRST FLOOR living! Best views of Intracoastal where you can cast a line on ...
- 2 Beds
- 1 Baths
- Bay Oaks Estates SubDv.
- 34242 Zip Code
Ultimate island living with views of the azure waters of the Gulf of Mexico and the powdery quartz sand of Siesta Key from every room. A few steps and your toes are in th...
- 2 Beds
- 2 Baths
- Jamaica Royale Elev Apts SubDv.
- 34242 Zip Code
Amazing income property opportunity! 2 units, each 2 bedroom/2 bathroom. Enjoy this 4 bedroom/4 bath, 1st and 2nd floor Siesta Village Duplex located just half a block aw...
- Sarasota Beach SubDv.
- 34242 Zip Code
Amazing income property opportunity! 2 units, each 2 bedroom/2 bathroom. Enjoy this 4 bedroom/4 bath, 1st and 2nd floor Siesta Village Duplex located just half a block aw...
- 4 Beds
- 4 Baths
- Sarasota Beach SubDv.
- 34242 Zip Code
Superb contemporary home on north Siesta Key with glorious views of Bayou Nettie. Located on quiet, private, prestigious Roberts Point Road, this .46 acre property has 55...
- 4 Beds
- 5.5 Baths
- Siesta Rev SubDv.
- 34242 Zip Code
The iconic setting is Cocoanut Bayou. The house is a work of art with a cool, mid-century vibe. This one-of-a-kind 4BR/4 plus two half BA residence is re-worked renovated...
- 4 Beds
- 4.5 Baths
- Cocoanut Bayou SubDv.
- 34242 Zip Code
An extremely rare property in the heart of Siesta Key Village and the worlds #1 beach. Enjoy this open, light and bright 2 bedroom 1 bath condo and then lease the propert...
- 2 Beds
- 1 Baths
- Calle Minogra SubDv.
- 34242 Zip Code
Pristine beautifully updated 2-bedroom 2-bath condo with extended living room in desirable ground floor location with walkout to lawn and view of boat basin. This tastef...
- 2 Beds
- 2 Baths
- Midnight Cove Ii SubDv.
- 34242 Zip Code
Bay front home situated on little under ½ acre lot, this custom built 5,233 sq/ft residence 4 bedrooms and 4 baths with high ceilings including an office which can easily...
- 4 Beds
- 4 Baths
- Siesta Bayside SubDv.
- 34242 Zip Code
LOCATION * LOCATION * LOCATION* Gorgeous updated and remodeled Coastal DUPLEX situation on a Corner Lot now available in the HEART of beautiful Siesta Key Village and the...
- Sarasota Beach SubDv.
- 34242 Zip Code
A spectacular 2-acre Gulf front estate in exclusive Sanderling Club on Siesta Key's coveted beach with arguably the most beautiful vistas in all of Sarasota. 189’ of pris...
- 5 Beds
- 4.5 Baths
- Sanderling Club SubDv.
- 34242 Zip Code
SIESTA KEY BAY-FRONT~Island Paradise Open Great Room concept with Breathtaking Bay Views! Spectacular Sunrises overlooking Little Sarasota Bay & Coveted Inter-Coastal Wat...
- 3 Beds
- 2.5 Baths
- Mangroves Sub The SubDv.
- 34242 Zip Code
This unique home is boasting with TONS of updates throughout, starting with the first floor has 2 bedrooms with a full master suite and access to the pool and canal. Next...
- 4 Beds
- 4.5 Baths
- Siesta Cove Sub SubDv.
- 34242 Zip Code
Showstopping Sarasota Bay and downtown city skyline views from the best vantage in Sarasota! Walls of windows towering 24 ft high greet you upon entry with the intracoast...
- 6 Beds
- 6.5 Baths
- Bay Island SubDv.
- 34242 Zip Code
Incredible location on the finest section of Siesta Keys white , wide Crescent Beach . This charming Florida townhouse is a short stroll to the wonderful Siesta Key Villa...
- 3 Beds
- 2.5 Baths
- Surfside Four SubDv.
- 34242 Zip Code
Enjoy stunning full Gulf Views and dazzling sunsets from this 6th floor condo in the South Tower. Whispering Sands, a 55 plus community has the luxury of having their own...
- 2 Beds
- 2 Baths
- Whispering Sands SubDv.
- 34242 Zip Code
Located within the exclusive gated community of Spice Bay on Siesta Key with just 14 homes, the two-story London Bay Homes' residence offers luscious garden views and dis...
- 4 Beds
- 4 Baths
- Spice Bay SubDv.
- 34242 Zip Code
**CHECK OUT 3D TOUR**SIESTA KEY CANAL FRONT RESIDENCE W/ A DOCK! This immaculate residence is poised on the quiet south end of Higel w/ canal access to SRQ Bay & the Gul...
- 3 Beds
- 3 Baths
- Sara Sands SubDv.
- 34242 Zip Code
Welcome to one of only a handful of WEEKLY RENTAL condos on Siesta Key...The Anchorage! This unit has been almost completely updated with new kitchen including granite to...
- 2 Beds
- 2 Baths
- Anchorage SubDv.
- 34242 Zip Code
PARADISE AWAITS in this recently updated CANAL FRONT HOME on Siesta Key and the ownership opportunities are ENDLESS! Primary, Secondary, OR Income Producing Property...Y...
- 3 Beds
- 2 Baths
- Siesta Manor SubDv.
- 34242 Zip Code
This custom built home, designed by an architect is surrounded by lush vegetation including a rare Staghorn Fern, Hong Kong Orchid trees, Oak trees, and a Gold Tree. The ...
- 3 Beds
- 3 Baths
- Royal Palm Harbor SubDv.
- 34242 Zip Code
One or more photo(s) has been virtually staged. World Class sunsets will be yours from this 3 level townhouse with unobstructed, stunning, Gulf and Beach views. Seldom on...
- 3 Beds
- 4.5 Baths
- Tiffany Sands SubDv.
- 34242 Zip Code
This location is supreme with just a short walk across the street to the white crystal sand of #1 Beach in America - Siesta Key Beach!! This condo is ideal for the perfe...
- 2 Beds
- 2 Baths
- Our House At The Bch SubDv.
- 34242 Zip Code
Siesta Key, Bay Island, spectacular home on corner lot. Ideal location 90' X 180' lot. Crystal sands of Shell Beach are only a half mile away! This 3 bedroom, 2 bath home...
- 5 Beds
- 3 Baths
- Bay Island Park SubDv.
- 34242 Zip Code
The most impressive view of the LITTLE SARASOTA BAY from all bedrooms and balconies of this luxuriously designed three story building.Directly on the INTRACOASTAL waterwa...
- 4 Beds
- 4.5 Baths
- Derby Bay South SubDv.
- 34242 Zip Code
Beautiful, turnkey furnished, not a single thing to-do, top floor 2BR/2BA unit ~ 300 yards south of Capt. Curts! Updated kitchen with wood cabinets, granite counters, new...
- 2 Beds
- 2 Baths
- Vista Hermosa SubDv.
- 34242 Zip Code
Under Construction. Located just a few homes from the mouth of Siesta Key's Grand Canal, this custom new home epitomizes the Florida lifestyle. The large 16,000SF+ lot f...
- 5 Beds
- 5.5 Baths
- Siesta Beach SubDv.
- 34242 Zip Code
An extremely rare property in the heart of Siesta Key Village and the worlds #1 beach. Enjoy this open, light and bright 2 bedroom 2 bath condo and then lease the propert...
- 2 Beds
- 2 Baths
- Calle Minogra SubDv.
- 34242 Zip Code
A classic, lovingly cared for single family home in a great location on Siesta Key! Imagine living just minutes away from the crystal quartz sands of Siesta Key beach. ...
- 3 Beds
- 2 Baths
- Waterside East SubDv.
- 34242 Zip Code
Gulf of Mexico view and the lowest price in Harbor Towers! Welcome to this nicely renovated condo with a Gulf of Mexico view. Renovations include a beautiful open kitchen...
- 1 Beds
- 1 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
Savor breathtaking azure Gulf views from this fabulous, custom-built Key West style home and guest house. Poised on the edge of the Gulf on a private lane near Siesta Key...
- 4 Beds
- 3.5 Baths
- Twitchell Ralph S Siesta Key SubDv.
- 34242 Zip Code
Wonderful Intracoastal Views! Immediately when you walk in the MOST desirable southeast view overlooking the intracoastal and pool greets you. This fully renovated condo ...
- 1 Beds
- 1 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
"This gorgeous two-bedroom, two-bath unit has a split floor plan that facilitates privacy between both master suits. The unit also has an open floor plan with multiple ac...
- 2 Beds
- 2 Baths
- Siesta Towers SubDv.
- 34242 Zip Code
Bayside Highrise with Western Exposure, Gulf Horizon Views, Bright and Light Unit. Elevator Access with Underground Parking for one car. Full Size Washer and Dryer in th...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
MILLION DOLLAR VIEW OF THE BAY from this sunny SIESTA KEY condo! Some of the many upgrades include Quartz counter tops requiring no maintenance, luxury vinyl plank floori...
- 2 Beds
- 2 Baths
- Sunrise Cove SubDv.
- 34242 Zip Code
Open and spacious living with magnificent views of the intracoastal waterway. Views from all living areas including a Florida room with lots of privacy for year-round enj...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
SIESTA KEY GEM ANYONE?? Here's your opportunity to own this exquisite 3/2, canal home with private saltwater pool, nestled in one of Siesta Key's most sought after commun...
- 3 Beds
- 2 Baths
- Siesta Isles SubDv.
- 34242 Zip Code
Accepted offer Pending Contract Execution MULTIPLE OFFERS - Seller Requests Highest & Best Offers By Deadline: 1/21/20, 5:00 PM (EST) SIESTA KEY ~ This is the ONE yo...
- 4 Beds
- 3 Baths
- Siesta Bayside SubDv.
- 34242 Zip Code
Charming and Beachy Siesta Key home centrally located on tree-lined property. Walk into a quiet 4 bed, 3.5 bath home with a large living room and open kitchen layout. It ...
- 4 Beds
- 3.5 Baths
- Siesta Beach SubDv.
- 34242 Zip Code
INVESTOR ALERT!!!BAY FRONT Turn Key BOHEMIAN CHIC Penthouse unit with gulf views. GREAT RENTAL WITH INCOME of $49,750.00 for 2019 ! 2020 BOOKINGS$$$$$$$$28,379.26 Through...
- 2 Beds
- 2 Baths
- Bay Oaks Estates SubDv.
- 34242 Zip Code
The opportunities are ENDLESS! Primary, Secondary, OR Income Producing Property...YOU PICK! The golden rule in Real Estate is LOCATION...and this GORGEOUS Siesta Key ho...
- 3 Beds
- 3.5 Baths
- Casa Del Soleil SubDv.
- 34242 Zip Code
Far removed but not far away, this enchanting Siesta Key home with separate guest house is designed for relaxed island living. Extremely private and set on unobstructed c...
- 4 Beds
- 3.5 Baths
- Ocean Beach SubDv.
- 34242 Zip Code
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Testimonials
Lisa Salvato - 5 stars! John is fabulous! He listened to what we wanted and emailed us only properties that applied. We live in New York and were interested in purchasing a Florida property. Having never met him prior to our visit to view the key properties of interest, from his e-mails, we didn't know what to expect . We feel like we hit the jackpot, John was professional, courteous and went out of his way to show us condos in a spread-out area. We have now closed on that purchase. Thank-you John for being a great negotiator and knowledgeable in your field. Your follow-through beyond the closing is appreciated and impressive. Thank-you Leslie for your work in the background to follow-up with all of the condo documents. We have sold and purchased homes before and John is at the top! February 2018
Robert Theofel — Above and beyond! Every aspect of the home buying process from initial search to closing went without a hitch due to Leslie and John’s expertise. When searching for a home, we received recommendations that were within our search criteria and the team was always available to show the homes that we selected. The recommendations we received during the negotiating, buying and closing process were excellent and we were able to close within a month of the initial viewing of the property. I would highly recommend them to anyone looking to buy a home!
Curt Johnson — My wife and I needed to sell our house, however there was much to do to get it ready. John and Leslie let us know how to fix-up the house to get the best possible response at the showings. We got it done and sold our house within 2 days of listing it with them. I think one of the best things I walked away with from the experience is how I felt trusting them with my home knowing that they had my best interest at hand. I would recommend John and Leslie to anyone who wants to be successful in selling or buying a home.
Jennifer Pearson — Leslie and John went above and beyond to help us sell our home! We had relocated 1900 miles away as we were trying to sell our house. They were in constant contact with us regarding the house and showings. They helped us find maintenance people when needed and even completed some things themselves. We would highly recommend them and should we return to the area, we will definitely use them to purchase a home!
Valerie Bologna — 5 stars! John helped my husband and I find a condo in Sarasota while we are living in another state. If there was something that we were interested in, he would go out right away and take pictures of the place and e-mail them to us. He never made us feel like we were wasting his time even though our purchase was not a million dollar listing! In a few years we will be calling on John again to find us a permanent place to live instead of seasonally. My husband and I appreciate all that he and his wife Leslie have done for us to make this purchase go as smooth as possible and we feel like we have gained new friends as well!
Victoria Harlow — 5 stars! Leslie went above and beyond with advice on staging, open houses, and cleaning and caring for my property while I was absent. Her teammate and husband John make a stellar team. I was so happy to get a great offer so close to my asking price. Awesome work! Thank-you for being vigilant and for the awesome care you took with selling my house. Your are the best that I've encountered after selling three houses over the years!
Edy Campos — 5 stars! - Can't get any better than John! He helped me all the way until the end, gives great advice, works fast, follows up and doesn't waste time. If you are serious about finding a place to call "home", I really recommend John Gregory!
Nancy Gallagher — If you're looking for a new home in Florida, John is a tireless agent to have on your side! If he doesn't know the answer to a question (which is rare) he will find it and in a timely manner! I highly recommend his services.
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