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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
Premier Resort Community with sweeping views of meticulous landscaping, beach and sunsets! This spacious 2 bedroom 2 bath condo has a glassed and screened lanai for enjoy...
- 2 Beds
- 2 Baths
- Gulf & Bay Club SubDv.
- 34242 Zip Code
Property is two parcels, Sarasota County Property ID #'s 0108090033 and 0108080015 totaling 2.86+/- acres. Direct Intracoastal Waterway frontage. Build a large estate/co...
- Stickney Point Sub SubDv.
- 34242 Zip Code
***World Class Siesta Key Beaches*** are located across the street from this completely remodeled 2- bedroom, 2 bath Waterfront condo. Harbor Towers Yacht & Racquet Club ...
- 2 Beds
- 2 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
WELCOME to this Turnkey furnished, pet friendly, vacation/income producing property. Just a short walk across the street to the #1 rated Siesta Key Beach with its abundan...
- 1 Beds
- 1 Baths
- White Sands Village SubDv.
- 34242 Zip Code
Tropical north Siesta Key waterfront lot to build your dream home. This desirable homesite of over 19,000 square feet is located on Coconut Bayou with a boat dock and lif...
- Siesta Rev SubDv.
- 34242 Zip Code
*VIRTUAL SHOWING AVAILABLE* This Siesta Key old Florida cottage is one story, 2 Bed/2 ½ Bath home With Guest House. Just 2 properties from Public Beach Access #8. It is a...
- 4 Beds
- 4 Baths
- Sarasota Beach SubDv.
- 34242 Zip Code
Location, location, location! A truly tropical beach front community with private beach, fishing pier and an easy walk to Siesta Key Village. A rarely available 2 bedroom...
- 2 Beds
- 1.5 Baths
- Sandy Cove SubDv.
- 34242 Zip Code
Dramatic southwest views down crescent beach. 10th floor 2b/2b priced to sell. You won't find a better buy on crescent beach. Consistent rental income year after year m...
- 2 Beds
- 2 Baths
- Crystal Sands SubDv.
- 34242 Zip Code
Located on The World Famous Siesta Key Beach. This remarkable 1 bedroom /1 bathroom unit is an amazing investment opportunity. Offering weekly rentals at Jamaica Royale. ...
- 1 Beds
- 1 Baths
- Jamaica Royale SubDv.
- 34242 Zip Code
Priced to Sell! On the Water views from your lanai, master bedroom and living room, Deep water canal for your boating pleasure, Beach Access, this unit has it all! 2 bedr...
- 2 Beds
- 2 Baths
- Siesta Harbor SubDv.
- 34242 Zip Code
Immaculate End Unit in Sailfish! Open and Airy sold with furniture, hurricane upgraded windows, Corian counters in the kitchen, dining area open to living room, lots of ...
- 2 Beds
- 2 Baths
- Siesta Harbor SubDv.
- 34242 Zip Code
Calling all boaters! A rare protected harbor for sailboats. DEEDED DEEP WATER BOAT DOCK #11 and lift accommodates a 45 ft boat. You have direct access to the Intracoastal...
- 3 Beds
- 2 Baths
- Harbour Towne SubDv.
- 34242 Zip Code
Here is your chance to own a condo that was featured on HGTV Beachfront Bargin Hunters, Bay Oaks is an amazing waterfront community. It has it's own fishing pier and doc...
- 2 Beds
- 2 Baths
- Bay Oaks SubDv.
- 34242 Zip Code
Discover 1.3 acres of beachfront perfection on north Siesta Key, where this private hideaway is the ideal place to enjoy endless tropical serenity. Imagine your island oa...
- Fidder Bayou SubDv.
- 34242 Zip Code
A treasure such as this rarely becomes available for sale. For those who savor midcentury modern design, this offering is exceptional. Designed in 1963 by famed architect...
- 3 Beds
- 2.5 Baths
- Siesta Isles SubDv.
- 34242 Zip Code
This luxurious home is located in highly desirable Tropical Cove on the upscale island of Siesta Key. The custom built, one-of-a-kind home was designed with entertaining ...
- 3 Beds
- 2 Baths
- North Harbor Sub SubDv.
- 34242 Zip Code
Virtual Tour Link available! Rarely available, Fisherman’s Cove beachfront condo with excellent rental income opportunity. A unique setting, at the southern and most priv...
- 2 Beds
- 2 Baths
- Fishermans Cove SubDv.
- 34242 Zip Code
A perfect fusion of sophistication, elegance, and coastal allure – this waterfront estate epitomizes the luxurious Florida lifestyle. Situated behind the private gates of...
- 5 Beds
- 4.5 Baths
- Midnight Harbor Sub SubDv.
- 34242 Zip Code
Located on Siesta Key’s bay front, this Three-bedroom estate captures an active and elegant island lifestyle with seamless indoor-outdoor living. Large double doors revea...
- 3 Beds
- 3.5 Baths
- Secluded Harbour SubDv.
- 34242 Zip Code
On Siesta Key, #1 beach in world. Walk to restaurant's, the beach and the ocean surf.
- 2 Beds
- 1 Baths
- Bay Oaks Estates SubDv.
- 34242 Zip Code
Welcome to the Sanderling Club, one of Siesta Key’s most coveted waterfront neighborhoods; a historic, Gulf-to-Bay community of canopied, estate-sized homesites. Located ...
- 4 Beds
- 4 Baths
- Sanderling Club SubDv.
- 34242 Zip Code
THE ONLY ONE OF ITS KIND on Siesta Key Beach. 180 degree UNOBSTRUCTED sunrise & sunset beachfront living! Only complex left with open air out-door dining lanai!! Jamaica ...
- 2 Beds
- 2 Baths
- Jamaica Royale Tower Ii SubDv.
- 34242 Zip Code
Experience vacation bliss at Jamaica Royale where this two-bedroom, two-bathroom condominium is positioned to view breathtaking beach and Gulf vistas. Situated in the Tow...
- 2 Beds
- 2 Baths
- Jamaica Royale Tower Ii SubDv.
- 34242 Zip Code
Turnkey furnished 2 bedroom 2 bath villa on Siesta key just south of the Stickney Point Bridge. Walk or bike to restaurants, shopping and the World Famous beaches of Si...
- 2 Beds
- 2 Baths
- Vista Hermosa SubDv.
- 34242 Zip Code
Exceptional Modern European Home. Recently redesigned and completely remodeled in 2018, this amazing home offers the highest standards of design, materials and functional...
- 3 Beds
- 2.5 Baths
- Ocean Beach SubDv.
- 34242 Zip Code
Cute and Cozy Beach Bungalow on Siesta Key! Walk to the beach and bike to Siesta Key Village! This property includes a quaint 2BR/2BA cottage with an additional, separate...
- 3 Beds
- 2.5 Baths
- Sarasota Beach SubDv.
- 34242 Zip Code
Wow! Steps to Siesta Key Beach, this residence is a boaters and beach lover’s dream come true. The deep-water boat dock is right outside your door, is 40 x 14 and accommo...
- 3 Beds
- 3 Baths
- Harbour Towne SubDv.
- 34242 Zip Code
You’ve long dreamed of your own distinct waterfront oasis, built exactly to your taste and positioned for the precise views and exposure of your choice. Set in the cozy f...
- Sarasota Beach SubDv.
- 34242 Zip Code
ACCESS THE VIRTUAL TOUR HERE! https://www.youtube.com/watch?v=vbTEWqOfShw 0.5 ACRE DIRECT GULF ACCESS, BOATER PARADISE | 85 FT WATERFRONT | VALUE IS IN THE LAND | Hom...
- 4 Beds
- 2 Baths
- 34242 Zip Code
Stroll to the cool, sugary sands of Siesta Key from this lovely condominium at Palm Bay Club. Situated near the pool, tennis courts, and new fitness center, you’ll enjoy ...
- 1 Beds
- 1.5 Baths
- Palm Bay Club SubDv.
- 34242 Zip Code
Lowest priced lot on Siesta Key. Now is the time to take advantage of this opportunity on world-famous Siesta Key – once again home to the #1 beach in the Nation. Majesti...
- Siesta Beach SubDv.
- 34242 Zip Code
Located on the coveted north end of Siesta Key with 104’ on boating water, this is the ultimate island lifestyle. Experience privacy and quick boating access to the azure...
- 3 Beds
- 3 Baths
- Vacated Gulf Ave SubDv.
- 34242 Zip Code
TRANQUIL SETTING AT THIS GULF TO BAY COMMUNITY WITH BEACH & BOAT DOCKS. Every day is like a vacation with two heated pools, saunas, two lighted tennis courts, pickle ba...
- 2 Beds
- 2 Baths
- Island Reef SubDv.
- 34242 Zip Code
Island living on Siesta Key… makes this spacious, corner condo your own perfect, Florida ‘get away’. Enjoy the greenbelt view of lush topical landscaping from your 19’ la...
- 2 Beds
- 2 Baths
- Excelsior Beach To Bay SubDv.
- 34242 Zip Code
BACK ON MARKET! Seasonal renters gone, ready to show with new, reduced price! Shows Very Well! Remarkable THREE Water View from this South Siesta Key condo. Yes, you ge...
- 2 Beds
- 2 Baths
- 34242 Zip Code
Gorgeous 7th floor unit with a view of the inter-coastal looking for new owners! Have your own slice of paradise on fabulous Siesta Key in this incredible complex, with a...
- 2 Beds
- 2 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
Penthouse Condo with Water views everywhere - living room, bedroom, lanai, kitchen. Charming one bedroom condo in resort-like Harbor Towers Yacht & Racquet Club that has...
- 1 Beds
- 1 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
More pics to come... Welcome to beautifully-maintained Bay Tree Club on Siesta Key! This is a fourth-floor END UNIT CONDO with BUILDING ELEVATOR. There are FOUR end unit ...
- 2 Beds
- 2 Baths
- Bay Tree Club SubDv.
- 34242 Zip Code
Land Value on this property is incredible and at this price you would be hard pressed to find a better deal! The home has been lovingly cared for by the original owner an...
- 3 Beds
- 3 Baths
- Sara Sands SubDv.
- 34242 Zip Code
Experience the epitome of life at the beach from this two-bedroom, two-bath condominium offering sweeping views of sugar sands and azure waters. Situated in Gulf and Bay ...
- 2 Beds
- 2 Baths
- Gulf & Bay Club SubDv.
- 34242 Zip Code
Looking for a piece of paradise on Siesta Key? Look no further. This one bedroom, one bathroom condo in Sunrise Cove can be your full-time residence, your pied-a-terre, y...
- 1 Beds
- 1 Baths
- Sunrise Cove SubDv.
- 34242 Zip Code
Own a part of Paradise and live on the pristine quartz sandy beach of Siesta Key. Inside your 5th floor condo have lunch on your screen balcony overlooking the full garde...
- 2 Beds
- 2 Baths
- Siesta Breakers SubDv.
- 34242 Zip Code
Sparkling One Bedroom with Two Full Baths! Once in a while a charmer that's been redone comes on the market! This is it! Gorgeous New Kitchen New Flooring, New Bathrooms,...
- 1 Beds
- 2 Baths
- Siesta Harbor SubDv.
- 34242 Zip Code
GROUND FLOOR UNIT NEAR THE ENTRANCE TO THE BUILDING - SPACIOUS 1271 SF UNIT WITH A 7' x 35' CLOSED PORCH OR LANAI MAKING 1,557 SF TOTAL UNIT. LAMINATE FLOORING THRU MOST...
- 2 Beds
- 2 Baths
- Whispering Sands SubDv.
- 34242 Zip Code
Welcome to Island Life! Siesta Key tropical home with a private pool surrounded by lush landscaping 1 mile from the Worlds Number One beach and 3/4 mile from the village...
- 3 Beds
- 2 Baths
- Siesta Beach SubDv.
- 34242 Zip Code
ENJOY AWESOME SUNRISES AND SUNSETS from this lovely one bedroom one bath condo at the southernmost end of Siesta Key. If you seek INCREDIBLE VIEWS, look no further. Beau...
- 1 Beds
- 1 Baths
- Pointe On Midnight Pass SubDv.
- 34242 Zip Code
Key West type home located on a canal with no bridges to the ICW. Two story with wood floors , plantation shutters, crown molding. Kitchen has corian countertops, maple c...
- 3 Beds
- 2 Baths
- Secluded Harbour SubDv.
- 34242 Zip Code
VIRTUAL TOUR LINK: https://www.youtube.com/embed/3kxBdnlmg0I Please call for a live virtual or personal tour scheduled at your convenience! 1/4 Acre Stunning Tropical...
- 2 Beds
- 3 Baths
- Sanderling Club SubDv.
- 34242 Zip Code
Epitomizing the essence of island living, this three-bedroom condominium is poised to enjoy all the tropical amenities of Siesta Key, home to what has been named the No. ...
- 3 Beds
- 3.5 Baths
- Casarina SubDv.
- 34242 Zip Code
Savor spectacular azure Gulf of Mexico views and the powdery white sands of world-famous Siesta Beach from this fabulous Gulf-front Siesta Key condo. With a desirable Sou...
- 3 Beds
- 3 Baths
- Crescent Siesta Key SubDv.
- 34242 Zip Code
What POSSIBILITIES! Such a UNIQUE and special site, Wow the history! A sample of Sarasota School of Architecture. Ralph Erickson was the designer and architect. One fami...
- 2 Beds
- 1 Baths
- Siesta Beach SubDv.
- 34242 Zip Code
Fantastic investment opportunity at Aloha Kai! This Gulf front complex features the largest pool on the island! With 3 night minimum rentals, this unit generates fantasti...
- 1 Beds
- 1 Baths
- Aloha Kai Apts SubDv.
- 34242 Zip Code
Super Value for Siesta Key! Peppertree a Gulf to Bay Property which means you have the Bayfront on the fishing pier; or to your own private beach on the Gulf of Mexico. (...
- 2 Beds
- 2 Baths
- Peppertree Bay SubDv.
- 34242 Zip Code
Charming vintage Florida condo - nicely updated and meticulously maintained. Wonderful location on Siesta Key near Turtle Beach. Bring your boat. Dock located right outsi...
- 2 Beds
- 2 Baths
- Coral Shores SubDv.
- 34242 Zip Code
Enjoy stunning sunset views from this exquisite 3rd floor, gulf front corner residence. With over 2400 square feet of luxurious living space, this property boasts 4 bedro...
- 4 Beds
- 3 Baths
- Residences On Siesta Key Beach SubDv.
- 34242 Zip Code
Just in time for season and located in one of Siesta Keys most popular resort communities. This ground floor unit has been updated with a newer kitchen, guest bath, windo...
- 2 Beds
- 2 Baths
- Palm Bay Club SubDv.
- 34242 Zip Code
Full Gulf Views from this rarely available 3rd floor, 2 bedroom condominium located directly across the street from the main entrance to Siesta Key Beach. Siesta Key b...
- 2 Beds
- 1 Baths
- La Siesta SubDv.
- 34242 Zip Code
LOCATION, LOCATION, LOCATION! Move right into this 2 bed/2 bath condo at beautiful Seashell. This complex is ideally situated along Siesta Key's Crescent Beach and offers...
- 2 Beds
- 2 Baths
- Seashell SubDv.
- 34242 Zip Code
Experience the essence of waterfront island living from this tropical Siesta Key home, located on Sarasota Bay with deeded beach access. Tucked away on the quieter south ...
- 3 Beds
- 4.5 Baths
- Tortoise Estates SubDv.
- 34242 Zip Code
This canal-front home's roots stem from a classic Florida flat-roofed beach cottage, which was completely updated in 2016 and sits privately in the heart of Siesta Key, j...
- 2 Beds
- 2 Baths
- Siesta Manor SubDv.
- 34242 Zip Code
Welcome to paradise, where a canopy tree-lined street escorts you to the tropically landscaped gardens of this private Gulf-front compound. Enjoy the serene sound of roll...
- 5 Beds
- 5.5 Baths
- White Beach Fruit Co Property SubDv.
- 34242 Zip Code
Beautifully remodeled condo in move in condition. New kitchen, baths and new flooring. Wonderful resort style community that includes a marina for owners. Tennis courts l...
- 2 Beds
- 2 Baths
- Harbor Towers Y & R SubDv.
- 34242 Zip Code
Don’t miss this fantastic opportunity to build your dream home on this 14,424 sf lot on the North End of Siesta Keys Grand Canal, only minutes to the Bay! Take advantage...
- Siestas Bayside Waterside SubDv.
- 34242 Zip Code
At the edge of the Gulf, just ½ mile north of Siesta Village, is a stylishly updated 2 bed, 2 bath, Ground floor unit "walk out" with far reaching views that start at the...
- 2 Beds
- 2 Baths
- Sea Village SubDv.
- 34242 Zip Code
Perfectly situated on the azure waters of Sarasota Bay this expansive 1+ acre waterfront home site is located on world-famous Siesta Key. With 130 feet of water frontage,...
- Cedars Of Siesta Key The SubDv.
- 34242 Zip Code
ABSOLUTELY STUNNING WATERFRONT HOME designed to deliver the very BEST of ISLAND LIFE. Ideally situated mid-Siesta Key, this 6,000 square foot home affords easy access to ...
- 5 Beds
- 5.5 Baths
- Royal Palm Harbor SubDv.
- 34242 Zip Code
LIVE IN PARADISE! What a RARE gem, this special lot is in a natural state! Paths have been created for a walk through. Build a retreat near the world famous #1 beach, S...
- Siesta Beach SubDv.
- 34242 Zip Code
Incredibly rare 3 bedroom free-standing villa on Siesta Key. Recently renovated with fully updated kitchen and baths, large private fenced back patio and 1 -car garage. L...
- 3 Beds
- 2 Baths
- Whispering Sands SubDv.
- 34242 Zip Code
A masterful & expansive private Gulf Front resort style retreat on over 1 acre of lush tropical landscaping with 150 ft of exclusive white sand beach affording infinite &...
- 5 Beds
- 6 Baths
- Sanderling Club SubDv.
- 34242 Zip Code
A Gulf front garden oasis in the exclusive Sanderling Club, this masterfully restored Mid-Century bungalow is the epitome of casual coastal grace, updated for today’s dis...
- 5 Beds
- 3.5 Baths
- Sanderling Club SubDv.
- 34242 Zip Code
This one of a kind home is located in Siesta Bayfront, an exclusive community of elegant and spacious estates. One of a kind home on deep sailboat water, minutes to the o...
- 5 Beds
- 3 Baths
- Siesta Bayside SubDv.
- 34242 Zip Code
Gulf & Bay Club Bayside is one of the prettiest communities on Siesta Key! Offering weekly rentals, resort style amenities, and deeded beach access plus a private garage...
- 3 Beds
- 2 Baths
- Gulf & Bay Club Bayside SubDv.
- 34242 Zip Code
Duplex in Tropical Old Florida setting on Siesta Key plus vacant buildable lot. 2 Upstairs units where you can open the windows and doors, letting the breeze sift throug...
- 34242 Zip Code
Perfectly located 1st floor unit in Harbour Towne Yacht Club with stunning views of the marina and canal to Robert’s Bay. Just a stone’s throw away from world famous Sies...
- 2 Beds
- 2 Baths
- Harbour Towne SubDv.
- 34242 Zip Code
LOWEST PRICED 2-BED ON ALL OF SIESTA KEY! Indulge yourself in this lush waterfront resort on world-famous Siesta Key, Florida… home to America's #1 beach! This exceptio...
- 2 Beds
- 2 Baths
- Bay Oaks Estates 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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Leslie Gregory
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