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Siesta Key Real Estate Search

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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

6157 Midnight Pass Road Unit E33, Siesta Key image
6157 Midnight Pass Road Unit E33, Siesta Key — 33 $469,990

WOW ! Just when you thought you ran out of options, this gorgeous 3rd floor, elevator equipped, 2 bedroom/2 full bath condo becomes available. This is the ONLY 2 bed/2 Ba...

  • 2 Beds
  • 2 Baths
  • Bay Oaks Estates SubDv.
  • 34242 Zip Code
704 Siesta Key Circle, Sarasota image
704 Siesta Key Circle, Sarasota $2,500,000

Casual Siesta Key elegance on sailboat water, no bridges, direct to Sarasota Bay and the Gulf of Mexico. This spectacular 4-bedroom, 3.5-bath fully turn-key furnished hom...

  • 4 Beds
  • 3 Baths
  • Siestas Bayside SubDv.
  • 34242 Zip Code
6268 Midnight Pass Road Unit 105, Sarasota image
6268 Midnight Pass Road Unit 105, Sarasota — Excelsior Beach To Bay $750,000

Enjoy your piece of paradise in a resort-style community on America’s top-rated beach. Beach chairs and lounges will await you on your own private beach to soak up the su...

  • 2 Beds
  • 2 Baths
  • Excelsior Beach To Bay SubDv.
  • 34242 Zip Code
4725 Gleason Avenue, Sarasota image
4725 Gleason Avenue, Sarasota $1,450,000 ▲

This beautiful and unique Siesta Key Mid-Century Home fCentury home has been designed by a Modernist Architect. It offers a spacious 3000 sq ft of living area and it i...

  • 3 Beds
  • 3 Baths
  • Ocean Beach SubDv.
  • 34242 Zip Code
1084 Sun N Sea Drive Unit 103E, Sarasota image
1084 Sun N Sea Drive Unit 103E, Sarasota $410,000

Excellent resort investment property with long term history. The Beach Club at Siesta Key is located just steps away from the sugar sand beach that has made Siesta Key wo...

  • 2 Beds
  • 2 Baths
  • Siesta SubDv.
  • 34242 Zip Code
6732 Sarasea Circle Unit 104C, Sarasota image
6732 Sarasea Circle Unit 104C, Sarasota $425,000

Excellent resort investment property with long term history. The Beach Club at Siesta Key is located just steps away from the sugar sand beach that has made Siesta Key wo...

  • 2 Beds
  • 2 Baths
  • Siesta SubDv.
  • 34242 Zip Code
6157 Midnight Pass Road Unit A52, Sarasota image
6157 Midnight Pass Road Unit A52, Sarasota — A $550,000

One of the biggest and nicest condo in Bay Oaks! Comes fully furnished and turn key so it's instantly ready to produce income and enjoy yourself. Each of 2 bedrooms are...

  • 2 Beds
  • 2 Baths
  • Bay Oaks Estates SubDv.
  • 34242 Zip Code
1084 Sun N Sea Drive Unit 101E, Sarasota image
1084 Sun N Sea Drive Unit 101E, Sarasota $410,000

Excellent resort investment property with long term history. The Beach Club at Siesta Key is located just steps away from the sugar sand beach that has made Siesta Key wo...

  • 2 Beds
  • 2 Baths
  • Siesta SubDv.
  • 34242 Zip Code
6732 Sarasea Circle Unit 100 C, Sarasota image
6732 Sarasea Circle Unit 100 C, Sarasota $425,000 ▲

Excellent resort investment property with long term history. The Beach Club at Siesta Key is located just steps away from the sugar sand beach that has made Siesta Key wo...

  • 2 Beds
  • 2 Baths
  • Siesta SubDv.
  • 34242 Zip Code
4510 Higel Avenue, Sarasota image
4510 Higel Avenue, Sarasota $1,250,000

Move-in ready 4 bedroom, 3 bath plus office. Just two miles from World Famous Siesta Key Beach and less than a mile from Siesta Key Village. This two story tropical retr...

  • 4 Beds
  • 3 Baths
  • Ocean Beach SubDv.
  • 34242 Zip Code
102 Pass Key Road Unit 102, Sarasota image
102 Pass Key Road Unit 102, Sarasota — 1 $320,000

Sandy Cove is the best-kept secret on Siesta Key. Here you have the close proximity to the famous Siesta Village, Siesta Public Beach to fill your time with shopping, di...

  • 1 Beds
  • 1 Baths
  • Sandy Cove SubDv.
  • 34242 Zip Code
6236 Midnight Pass Road Unit 208, Sarasota image
6236 Midnight Pass Road Unit 208, Sarasota — 1 $650,000

Siesta Dunes is a highly sought-after Siesta Key resort, and this is a fantastic opportunity to secure a unit at only $650,000. Weekly minimum rentals allow owners to max...

  • 2 Beds
  • 2 Baths
  • Siesta Dunes Beach SubDv.
  • 34242 Zip Code
1035 Seaside Drive Unit 305, Sarasota image
1035 Seaside Drive Unit 305, Sarasota — Ten35 Seaside $3,800,000

Pre-Construction. To be built. Pre-Construction. To be built. Introducing TEN35 SEASIDE. Located directly on the sands of world-renowned Siesta Key Beach, TEN35 SEASIDE b...

  • 3 Beds
  • 3 Baths
  • Siesta Beach SubDv.
  • 34242 Zip Code
1300 N N Portofino Dr Drive Unit 304SAI, Sarasota image
1300 N N Portofino Dr Drive Unit 304SAI, Sarasota — Sailfish $349,900

Unusually Available! Spacious one bedroom Condo with two Full Baths! In addition, Fully Glass Enclosed Lanai with view of the canal and intracoastal waterway!Updated Kitc...

  • 1 Beds
  • 2 Baths
  • Siesta Harbor SubDv.
  • 34242 Zip Code
6300 Midnight Pass Road Unit 1201, Sarasota image
6300 Midnight Pass Road Unit 1201, Sarasota — Crystal Sands $1,300,000

Beachfront Corner Penthouse Unit with Stunning Views as far as the eye can see of the Gulf of Mexico towards Venice! Enjoy the beautiful quartz sand of Siesta Key Beach ...

  • 2 Beds
  • 2 Baths
  • Crystal Sands SubDv.
  • 34242 Zip Code
757 Beach Road Unit 106, Sarasota image
757 Beach Road Unit 106, Sarasota — 757 $675,000

First Floor, walk out unit, directly across the street from Siesta Key’s famous, Powdery White Sand Beach. You will love the fresh air in your screened in lanai. Weekly ...

  • 2 Beds
  • 2 Baths
  • Crescent Royale SubDv.
  • 34242 Zip Code
1055 Beach Road Unit B-703, Sarasota image
1055 Beach Road Unit B-703, Sarasota — East Tower $790,000

This seventh floor, END UNIT, "Penthouse" offers the amazing Siesta Key Beach directly across the street! Wake up to spectacular sunrise sky's, exercise on the beach, or...

  • 2 Beds
  • 2 Baths
  • Our House At The Bch SubDv.
  • 34242 Zip Code
8424 Midnight Pass Road, Sarasota image
8424 Midnight Pass Road, Sarasota $3,999,000

Siesta Key custom built waterfront home. This 2 story modern home with basement sits on 1 full flat acre and offers 200' (aprox) of unobstructed panoramic water views on ...

  • 3 Beds
  • 3 Baths
  • 1350 Main Residential SubDv.
  • 34242 Zip Code
4027 Roberts Point Road, Sarasota image
4027 Roberts Point Road, Sarasota $3,295,000

Water water everywhere! Walk in the house and don't be surprised to see dolphins jumping in the water adjacent to one of two back decks. This 3-story house--with an ele...

  • 5 Beds
  • 5 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
6535 Peacock Road, Sarasota image
6535 Peacock Road, Sarasota — 6535 $829,900

Looking for something in the middle of paradise?! GREAT DUPLEX WITH GREAT LOCATION! Located in the highly sought-after community of Great Siesta Key, right in the heart ...

  • Stickney Point Sub SubDv.
  • 34242 Zip Code
5361 Siesta Court, Sarasota image
5361 Siesta Court, Sarasota $829,000

Perfectly located Siesta Key home in desirable Siesta Cove neighborhood with quick access to the #1 beach in the USA. Tucked amongst lush Florida landscaping this 3 bedro...

  • 3 Beds
  • 2 Baths
  • Siesta Cove Sub SubDv.
  • 34242 Zip Code
6300 Midnight Pass Road Unit 701, Sarasota image
6300 Midnight Pass Road Unit 701, Sarasota — Crystal Sands $979,000

This stunning 7th floor unit boasts magnificent Southwest views of Siesta Key’s blue waters and unforgettable sunsets. The unit has been thoughtfully UPDATED with beautif...

  • 2 Beds
  • 2 Baths
  • Crystal Sands SubDv.
  • 34242 Zip Code
513 Givens Street, Sarasota image
513 Givens Street, Sarasota $1,850,000

Very comfortable Siesta-style living inside and out, by the pool and canal. House painted, new ac, courtyard in front for entertaining/relaxed vibe. Courtyard area in fro...

  • 3 Beds
  • 3 Baths
  • Ocean Beach SubDv.
  • 34242 Zip Code
319 Ogden Street, Sarasota image
319 Ogden Street, Sarasota $1,295,000

Incredible move-in ready home located on the coveted north end of Siesta Key. Explore and walk through this stunning 4 bedroom, 3 bathroom home with the 3D virtual tour...

  • 4 Beds
  • 3 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
3821 Flamingo Avenue, Sarasota image
3821 Flamingo Avenue, Sarasota $6,900,000

This magnificent estate on 1 ½ acres on the open Bayfront was originally built in 1925 by John Tuttle with heart pine floors and first cut, clear cut cypress on the beame...

  • 5 Beds
  • 4 Baths
  • Bay Island SubDv.
  • 34242 Zip Code
5151 Windward Avenue, Sarasota image
5151 Windward Avenue, Sarasota $2,950,000

Magnificent canal front home on the north end of Siesta Key. This 2017 custom built Arthur Rutenberg model has 4 bedrooms, 5.5 baths and a media room/5th bedroom. The enc...

  • 4 Beds
  • 5 Baths
  • Sara Sands SubDv.
  • 34242 Zip Code
1200 E Peppertree Lane Unit 602, Sarasota image
1200 E Peppertree Lane Unit 602, Sarasota — 1200 $849,900

Penthouse on Siesta Key! Stunning views of downtown Sarasota and the Intercoastal Bay. Peppertree is on 16 tropical acres from our own private beach to the bay. It is cen...

  • 2 Beds
  • 2 Baths
  • Peppertree Bay SubDv.
  • 34242 Zip Code
222 Beach Road Unit 3, Sarasota image
222 Beach Road Unit 3, Sarasota — 222 Beach Road $4,395,000 ▲

A rare offering; experience the ultimate lifestyle on Siesta Key. Savor the beach life while making wonderful family memories in this spectacular townhome facing the ocea...

  • 3 Beds
  • 3 Baths
  • 0222 Beach Rd SubDv.
  • 34242 Zip Code
5961 Midnight Pass Road Unit 325, Sarasota image
5961 Midnight Pass Road Unit 325, Sarasota — 5961 $1,199,000

Unbelievable! A unit like this hasn't been on the market in over 10 years! This is the anomaly property you have been waiting for. Almost double the size of a standa...

  • 2 Beds
  • 2 Baths
  • Palm Bay Club SubDv.
  • 34242 Zip Code
5400 Ocean Boulevard Unit 10-2, Sarasota image
5400 Ocean Boulevard Unit 10-2, Sarasota — 5400 $1,165,000

This is it! Once in a lifetime opportunity at the iconic Terrace on Siesta Key! Designed by the renowned Frank Folsom Smith, the Terrace offers some of the most unparalle...

  • 1 Beds
  • 1 Baths
  • Terrace SubDv.
  • 34242 Zip Code
3536 Bayou Louise Lane, Sarasota image
3536 Bayou Louise Lane, Sarasota $6,975,000

One of the best locations in Sarasota on the coveted north end of Siesta Key, this Gulf-front estate has it all. Enjoy endless views of the Gulf of Mexico, Big Pass, Sout...

  • 4 Beds
  • 4 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
3484 Hamilton Avenue, Sarasota image
3484 Hamilton Avenue, Sarasota $1,249,000

Siesta Key, Bay Island, home on double corner lot. Crystal sands of Shell Beach are only a walk or bike away! This 3 bedroom, 2 bath home upstairs, and downstairs with an...

  • 5 Beds
  • 3 Baths
  • Bay Island Park SubDv.
  • 34242 Zip Code
469 Canal Road Unit 469, Sarasota image
469 Canal Road Unit 469, Sarasota $2,050,000

•*´¨SIESTA KEY`*•.¸¸.•WEEKLY RENTAL•.¸¸.•*´CANAL FRONT¨`*•.¸PRIVATE DOCK / LIFT¸.•*** •*´BEACH VIEWS¨`*•.¸PRIVATE ELEVATOR¸.••.¸1/2 MILE TO VILLAGE¸.•*´ ...

  • 3 Beds
  • 3 Baths
  • Grand Siesta SubDv.
  • 34242 Zip Code
3916 N Shell Road, Sarasota image
3916 N Shell Road, Sarasota $4,350,000

Paradise awaits in this private retreat located in the desirable North End of Siesta Key. Custom built in 2017, this one of a kind home is minutes from Siesta Key beach/v...

  • 4 Beds
  • 3 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
221 Garden Lane, Sarasota image
221 Garden Lane, Sarasota $1,650,000

Whether you make this Siesta Key Beauty your home, your winter get-away or a guest retreat, it will be the perfect choice. Just a short walk to Shell Beach or take the tr...

  • 4 Beds
  • 4 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
3446 Anglin Drive, Sarasota image
3446 Anglin Drive, Sarasota $1,495,000

Attention all Investors! Bay Isle pool home is a rarity as it resides in the only area on Siesta Keys where weekly rentals are legally permitted. The home will stun you,...

  • 4 Beds
  • 3 Baths
  • Bay Island Park SubDv.
  • 34242 Zip Code
8423 Midnight Pass Road, Sarasota image
8423 Midnight Pass Road, Sarasota $7,995,000

Escape to your very own private island paradise on world-famous Siesta Key. Majestically poised along the shimmering waters of the Intracoastal Waterway sits this masterf...

  • 6 Beds
  • 6 Baths
  • Siesta Key SubDv.
  • 34242 Zip Code
6518 Midnight Pass Road Unit 512, Sarasota image
6518 Midnight Pass Road Unit 512, Sarasota — House Of The Sun $1,100,000

Very Rarely Available Top Floor Gulf Front Unit. Owners have held this real estate since 1986! Located at the very top corner of the entire building! Highest and best G...

  • 2 Beds
  • 2 Baths
  • House Of The Sun (Was Known As Haleakala) SubDv.
  • 34242 Zip Code
1087 W Peppertree Drive Unit 221D, Sarasota image
1087 W Peppertree Drive Unit 221D, Sarasota — 1087 $799,000

Gulfside garden downstairs unit with steps; 2 bedroom 2 bath with garage and lake view! You will love this split-level unit with great room size and floor plan. Short w...

  • 2 Beds
  • 2 Baths
  • Peppertree Bay SubDv.
  • 34242 Zip Code
901 Beach Road Unit 202, Sarasota image
901 Beach Road Unit 202, Sarasota — 901 $499,000

This spectacular 2 bedroom 1 bath condo, directly facing magnificent Siesta Key Beach, where the sugary sand never disappoints. This condo has easy access to Siesta villa...

  • 2 Beds
  • 1 Baths
  • La Siesta SubDv.
  • 34242 Zip Code
6300 Midnight Pass Road Unit 806, Sarasota image
6300 Midnight Pass Road Unit 806, Sarasota — 6300 $1,150,000

Crystal Sands offers the best beach views on Siesta Key. Every room provides unobstructed enchanting views of sunsets and the glittering lights of downtown Sarasota in th...

  • 2 Beds
  • 2 Baths
  • Crystal Sands SubDv.
  • 34242 Zip Code
6905 Point Of Rocks Road, Sarasota image
6905 Point Of Rocks Road, Sarasota $3,499,000 ▲

Fantastic income producing property just steps to world famous Siesta Beach. This 4 unit building consists of 2 2 bedroom 2 bath units and 2 1 bedroom 1 bath units. The...

  • Point Of Rocks Terrace SubDv.
  • 34242 Zip Code
6342 Midnight Pass Road Unit 320, Sarasota image
6342 Midnight Pass Road Unit 320, Sarasota — 3 $1,115,000

Sweeping Gulf of Mexico views create a captivating scene within this coastally inspired condominium. A picture-perfect vision of paradise is just beyond your screened lan...

  • 2 Beds
  • 1 Baths
  • Midnight Cove Ph 1 & 2 SubDv.
  • 34242 Zip Code
6140 Midnight Pass Road Unit 208, Sarasota image
6140 Midnight Pass Road Unit 208, Sarasota — 6140 $1,189,000

Immerse yourself in the breathtaking views of Siesta Key’s world-famous white sand beach and shimmering ocean from this rarely available extra-large furnished corner unit...

  • 2 Beds
  • 2 Baths
  • Horizons West SubDv.
  • 34242 Zip Code
5966 Midnight Pass Road Unit G-54, Sarasota image
5966 Midnight Pass Road Unit G-54, Sarasota — Grand Tower $750,000

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
5830 Midnight Pass Road Unit 19, Sarasota image
5830 Midnight Pass Road Unit 19, Sarasota — Jamaica Royale $450,000

Welcome and relax in this open floor plan that allows the sunlight to flow continuously throughout, providing a warm and inviting ambience experienced the moment you walk...

  • 1 Beds
  • 1 Baths
  • Jamaica Royale SubDv.
  • 34242 Zip Code
4972 Ocean Boulevard, Sarasota image
4972 Ocean Boulevard, Sarasota $800,000

Walk to Siesta Key Beaches! Walk to The Village! Canal Front with Gulf Access! Total 1/2 Acre Cleared lot with permitted boat dock on property.

  • Siesta SubDv.
  • 34242 Zip Code
5342 Hidden Harbor Road, Sarasota image
5342 Hidden Harbor Road, Sarasota $2,995,000

A rare offering on Siesta Key, this nearly 1-acre parcel with frontage along Roberts Bay is an unprecedented opportunity to build the island home of your dreams in an unp...

  • Hidden Harbor SubDv.
  • 34242 Zip Code
304 Calle Miramar Unit 304-S2, Sarasota image
304 Calle Miramar Unit 304-S2, Sarasota — 304-S2 $1,895,000

Stunning Siesta Key 4 Bedroom 3.5 Bath Multi-level Penthouse in the heart of the Village. This exquisite property offers 3,236 sq ft of living space with attached 2 car g...

  • 4 Beds
  • 3 Baths
  • Beach Villas At The Oasis SubDv.
  • 34242 Zip Code
311 Ogden Street, Sarasota image
311 Ogden Street, Sarasota $1,595,000

This is the One! Incredible custom built home featuring 5 bedroom and 4.5 bathroomslocated on World Famous Siesta Key*Bright and open spacious floor plan* heated pool ho...

  • 5 Beds
  • 4 Baths
  • Siesta Rev SubDv.
  • 34242 Zip Code
719 Avenida Del Norte, Sarasota image
719 Avenida Del Norte, Sarasota $1,500,000

One or more photo(s) has been virtually staged. Rare opportunity to own a private gated estate directly on Grand Canal with 228' of deep water canal frontage in the heart...

  • 4 Beds
  • 3 Baths
  • Sarasota Beach SubDv.
  • 34242 Zip Code
4750 Ocean Boulevard Unit 202, Sarasota image
4750 Ocean Boulevard Unit 202, Sarasota — Oceane $4,850,000

An exceptional designer residence on Siesta Key with an expansive layout, endless Gulf views and thoughtful integrations for upscale living, Océane sets a new standard in...

  • 4 Beds
  • 4 Baths
  • Oceane SubDv.
  • 34242 Zip Code
5239 Calle Menorca, Sarasota image
5239 Calle Menorca, Sarasota $2,699,000 ▼

This proven high producing income property is finally for sale! This quadplex is perfectly located in the heart of Siesta Village making it a highly coveted spot for rent...

  • 8 Beds
  • 6 Baths
  • Sarasota Beach SubDv.
  • 34242 Zip Code
5241 Calle Menorca, Sarasota image
5241 Calle Menorca, Sarasota $2,699,000 ▼

This proven high producing income property is finally for sale! This quadplex is perfectly located in the heart of Siesta Village making it a highly coveted spot for rent...

  • Sarasota Beach SubDv.
  • 34242 Zip Code
341 Avenida De Mayo, Sarasota image
341 Avenida De Mayo, Sarasota $999,995

WATERFRONT HOME SIESTA VILLAGE,siesta key canal front home .This property is right in the heart of siesta village,it is a 1 minute walk to ocean blvd. and canal rd. Thi...

  • Sarasota Beach SubDv.
  • 34242 Zip Code
6300 Midnight Pass Road Unit 309, Sarasota image
6300 Midnight Pass Road Unit 309, Sarasota — Section 2 $974,000 ▼

This beautifully renovated condominium sits front and center on the world famous Crescent Beach on Siesta Key. Upon entering this property you will immediately be drawn ...

  • 2 Beds
  • 2 Baths
  • Crystal Sands SubDv.
  • 34242 Zip Code
116 Vista Hermosa Circle Unit 306C, Sarasota image
116 Vista Hermosa Circle Unit 306C, Sarasota — C $350,000

LOWEST PRICED 2/2 ON #1 BEACH #SIESTA KEY! THIS AFFORDABLE UNIT IS LOCATED NEAR BEACH ACCESS AND JUST A BLOCK TO SIESTA SOUTH VILLAGE SHOPS AND DINING! This 2BR/2Ba unit ...

  • 2 Beds
  • 2 Baths
  • Vista Hermosa SubDv.
  • 34242 Zip Code
4708 Ocean Boulevard Unit E4, Sarasota image
4708 Ocean Boulevard Unit E4, Sarasota — Windward Passage $1,575,000 ▼

Magnificent Gulf of Mexico Sunset Views along with wide sweeping views of Big Pass are just the beginning. Arguably one of the VERY best water views you might see! Step r...

  • 3 Beds
  • 3 Baths
  • Windward Passage SubDv.
  • 34242 Zip Code
5920 Midnight Pass Road Unit 1106TO, Sarasota image
5920 Midnight Pass Road Unit 1106TO, Sarasota — Tower $1,099,000 ▼

Iconic Sarasota Surf and Racquet Club 11th floor Tower unit with sweeping Gulf of Mexico views. Positioned in a prime location on the # 1 ranked beach in the USA. These...

  • 2 Beds
  • 2 Baths
  • Sarasota Surf & Racquet SubDv.
  • 34242 Zip Code
5855 Midnight Pass Road Unit 218, Sarasota image
5855 Midnight Pass Road Unit 218, Sarasota — Harbor Towers $629,900 ▼

Enjoy resort style living in this 3 bedroom, 3 full bath end unit in recently renovated Harbor Towers Yacht and Racquet Club. This condo has tile flooring throughout, gra...

  • 3 Beds
  • 3 Baths
  • Harbor Towers Y & R SubDv.
  • 34242 Zip Code
1001 Point Of Rocks Road Unit 611, Sarasota image
1001 Point Of Rocks Road Unit 611, Sarasota — Siesta Sands Building C $2,600,000

Rare opportunity to own a top floor 3 bedroom 2 bath Gulf Front condo located on the southern end of world renowned Crescent Beach. Featuring expansive and captivating v...

  • 3 Beds
  • 2 Baths
  • Siesta Sands Resort (Timeshare) SubDv.
  • 34242 Zip Code
5255 Calle Menorca Unit 5259, Sarasota image
5255 Calle Menorca Unit 5259, Sarasota $1,395,000

Imagine waking up in your very own beach bungalow in the heart of Siesta Key Village with your own private backyard oasis! You will fall in love with this adorable 2-bedr...

  • 2 Beds
  • 2 Baths
  • Sarasota Beach SubDv.
  • 34242 Zip Code
6264 Midnight Pass Road Unit 101, Sarasota image
6264 Midnight Pass Road Unit 101, Sarasota — Na $999,000

PERFECT PLACE TO WATCH THE SUNSET!! 2 bedroom/2 bath gulf front condo located on Crescent Beach. Walk out onto your patio and directly down to the courtyard area with a p...

  • 2 Beds
  • 2 Baths
  • Excelsior Beach To Bay SubDv.
  • 34242 Zip Code
135 Avenida Veneccia, Sarasota image
135 Avenida Veneccia, Sarasota $1,895,000

Siesta Key living at it finest and only a short stroll to the beach! This adorable beach cottage awaits you and has all the amenities you want in your home away from home...

  • 3 Beds
  • 2 Baths
  • Mira Mar Beach SubDv.
  • 34242 Zip Code
548 Beach Road Unit 548, Sarasota image
548 Beach Road Unit 548, Sarasota — Tiffany Sands $1,695,000

Live the dream - savor stunning views of the Gulf of Mexico and Siesta Beach every day and amazing sunsets each evening from this rarely available, end-unit townhouse con...

  • 3 Beds
  • 3 Baths
  • Tiffany Sands SubDv.
  • 34242 Zip Code
9393 Midnight Pass Road Unit 901, Sarasota image
9393 Midnight Pass Road Unit 901, Sarasota — 9393 $699,000

BREATHTAKING WATER VIEWS ON 3 SIDES & FROM EVERY ROOM -- Surrounded by water, this light and bright, rarely available 9th floor 2 bedroom 2 bath END UNIT affords some of ...

  • 2 Beds
  • 2 Baths
  • Pointe On Midnight Pass SubDv.
  • 34242 Zip Code
1260 Dolphin Bay Way Unit 301, Sarasota image
1260 Dolphin Bay Way Unit 301, Sarasota — 0000 $1,175,000 ▼

The minute you walk into this recently remodeled 3 bedroom, 3 full-bath, Siesta Key condo you’ll be blown away by the amazing water view that spans the entire width of th...

  • 3 Beds
  • 3 Baths
  • Dolphin Bay-Siesta Key SubDv.
  • 34242 Zip Code
915 Seaside Drive Unit 507, Sarasota image
915 Seaside Drive Unit 507, Sarasota — Siesta Key Beach Residences $2,375,000

We present to you an immaculate, BEACHFRONT residence with PANORAMIC WATERFRONT VIEWS from the highly-regarded Hyatt Beach Residence Club of Siesta Key! Luxury awaits fro...

  • 3 Beds
  • 3 Baths
  • Siesta SubDv.
  • 34242 Zip Code
5400 Ocean Boulevard Unit 1-4, Sarasota image
5400 Ocean Boulevard Unit 1-4, Sarasota — Terrace $799,999 ▼

This oversized one bedroom, one bathroom condo in The Terrace building offers ideal island living. The Terrace, designed by Frank Folsom Smith, sits on the widest sectio...

  • 1 Beds
  • 1 Baths
  • Terrace SubDv.
  • 34242 Zip Code
5400 Ocean Boulevard Unit 1-3, Sarasota image
5400 Ocean Boulevard Unit 1-3, Sarasota — Terrace $1,649,999 ▼

One or more photo(s) has been virtually staged. The Virtual Tour is a Future Rendering. An unpolished gem ready to be renovated. Three-bedroom, two-and-a-half bathroom...

  • 3 Beds
  • 2 Baths
  • Terrace SubDv.
  • 34242 Zip Code
1214 Sharswood Lane, Sarasota image
1214 Sharswood Lane, Sarasota $850,000

Take advantage of this ready to build opportunity in a boutique gated waterfront community on world-famous Siesta Key. Spice Bay, home to only 14 homesites, most of which...

  • Spice Bay SubDv.
  • 34242 Zip Code
5966 Midnight Pass Road Unit G-52, Sarasota image
5966 Midnight Pass Road Unit G-52, Sarasota — 1 $895,000

Location Location Vacation!! This gorgeous 5th floor turn-key furnished tower unit is front and center with direct panoramic views of the Gulf of Mexico's crystalline wat...

  • 1 Beds
  • 1 Baths
  • Palm Bay Club SubDv.
  • 34242 Zip Code
445 Beach Road, Sarasota image
445 Beach Road, Sarasota $3,149,000

Located just steps from world-famous Siesta Key Beach, residences A, and B at 445 Beach Road present a stunning opportunity for year-round living, a seasonal getaway, or ...

  • Casa De La Playa SubDv.
  • 34242 Zip Code
640 Calle Del Otono, Sarasota image
640 Calle Del Otono, Sarasota $2,490,000 ▼

This gorgeous duplex on Siesta Key is a must-see! Perfectly located only feet from the world-famous siesta key beach and only minutes from the Siesta village with all of ...

  • Sarasota Beach SubDv.
  • 34242 Zip Code
6266 Midnight Pass Road Unit 404, Sarasota image
6266 Midnight Pass Road Unit 404, Sarasota — 6266 $895,000 ▼

Appreciating Gulf of Mexico views and the true essence of island bliss, this completely remodeled condominium in Excelsior Beach to Bay grants a life of posh relaxation. ...

  • 2 Beds
  • 2 Baths
  • Excelsior Beach To Bay SubDv.
  • 34242 Zip Code
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Community Info & Listings

Sarasota County (click on each line)

  • Palmer Ranch
  • Longboat Key
  • Siesta Key
  • Venetian Golf & River
  • Downtown Sarasota
  • East Sarasota
  • Lido Key
  • South Sarasota
  • Osprey & Nokomis
  • Venice & Venice Island
  • North Port
  • Englewood

Manatee County (click on each line)

  • Anna Maria Island
  • Lakewood Ranch
  • Palma Sola
  • University Park
  • Greyhawk Landing
  • Heritage Harbour
  • Mote Ranch
  • Waterlefe
  • East Bradenton
  • West Bradenton
  • Parrish
  • Palmetto

Helpful Links (click on each line)

  • Sarasota County | Taxes • Schools • Chamber
  • Manatee County | Taxes • Schools • Chamber
  • Charlotte County | Taxes • Schools • Chamber
  • Pinellas County | Taxes • Schools • Chamber
  • Hillsborough County | Taxes • Schools • Chamber

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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FINE Properties
5224 Paylor Lane
Sarasota, FL 34240
John Gregory: 941-725-9946
Leslie Gregory: 941-238-7714

 

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