Siesta Key: A Famous Barrier Island with Great Real Estate

Home buyers who are concerned about the reputation of the real estate market they choose to invest in will find that Siesta Key excels in this regard. Siesta Key is one of the most famous barrier islands in Florida, and it is among the most exclusive housing markets. This does not mean, however, that properties on this island are beyond reach.

The two best-known facts about Siesta Key are related to the dazzling, white-sandy beaches that people from around the world come to visit each year. Of all beaches in Florida, Siesta Key has an enviable reputation as being perfect for families. A lesser-known fact is that there are 50 residential neighborhoods on this island, and they are all waiting to be discovered.

Siesta Key is highly recommended for real estate investors looking for waterfront property. To this effect, there are quite a few options: Beachfront condominiums, handsome estates overlooking Roberts Bay, and single-family residences lined up alongside the canals, lagoons and bayous of the island. Most visitors head straight to Siesta Beach and miss the various communities on the northern and southern ends of the island.

Siesta Key is connected to the Florida mainland by Siesta Drive in the north and Stickney Point road in the south. Between these two scenic causeways, home shoppers can find low-rise condominium units and villas starting around $200K. All homeowners in Siesta Key live just blocks away from the beach, and the lucky ones enjoy sweeping views of the Gulf of Mexico and the Sarasota skyline.

The main amenity for Siesta Key residents is, of course, enjoying the incredible beach. Many neighbors are also boaters, anglers and scuba divers. Most condominium residents have access to swimming pools, fitness centers, clubhouses, tennis courts, and more. A few of the neighborhoods follow special themes; for example, those who live at the Hyatt Siesta Key get to enjoy a maintenance-free, resort lifestyle. Fisherman’s Cove is ideal for angler and fishing enthusiasts; Roberts Point is a nautical neighborhood, and the fancy Sarasota Surf and Racquet Club is perfect for tennis lovers.

There are abundant suburban comforts to enjoy in Siesta Key without having to leave the island; however, South Sarasota and its numerous commercial districts are located just across the bay. As of 2014, one private learning academy served the island, but most young residents are served by nearby public schools.

Siesta Key Florida Homes & Condos for Sale

5058 Windward Avenue, Sarasota $2,299,000

Under Construction. Anticipated completion date expected May of 2020. Nutter Custom Construction introduces,"The Anchorage", a contemporary coastal design with 3,471 air...

3 Beds
3 Baths
Sara Sands SubDv.
34242 Zip Code

9062 Midnight Pass Road Unit 7, Sarasota image

9062 Midnight Pass Road Unit 7, Sarasota — 9062 $395,000

You absolutely cannot miss this on the water beauty! Tucked down at the end of Siesta Key just past Turtle Beach is the home that you have been looking for. This 2 bedroo...

2 Beds
2 Baths
Moorings SubDv.
34242 Zip Code

9240 Midnight Pass Road Unit B, Sarasota image

9240 Midnight Pass Road Unit B, Sarasota — B $520,000

Looking to own a piece of paradise? Here's a great investment with solid tenants in place. At the south end of Siesta just past Turtle Beach on the water with water acces...

3 Beds
2 Baths
Starlite Roof SubDv.
34242 Zip Code

5740 Midnight Pass Road Unit 401, Sarasota image

5740 Midnight Pass Road Unit 401, Sarasota — 5740 $1,625,000

Shimmering turquoise waters of the Gulf of Mexico and pillow-soft sands of Siesta Key Beach grant an experience of retreat living from the moment you enter this perfectly...

3 Beds
2 Baths
Gulf N Bay SubDv.
34242 Zip Code

5964 Midnight Pass Road Unit 148, Sarasota image

5964 Midnight Pass Road Unit 148, Sarasota — 5964 $619,000

Enjoy beachside bliss at Palm Bay Club, a tropical resort spanning from the beach to the bay on Siesta Key. This two-bedroom residence is the perfect island hideaway for ...

2 Beds
2 Baths
Palm Bay Club SubDv.
34242 Zip Code

6415 Midnight Pass Road Unit 605, Sarasota image

6415 Midnight Pass Road Unit 605, Sarasota — 6415 $477,900

Turnkey furnished open and bright condo on the 6th floor with low fees. The Anchorage on Siesta Key is in such demand that there are rarely any condos for sale. Seldom on...

2 Beds
2 Baths
Anchorage SubDv.
34242 Zip Code

6342 Midnight Pass Road Unit 220, Sarasota image

6342 Midnight Pass Road Unit 220, Sarasota — 2 $1,300,000

Rarely available!! A beautiful, spacious, clean, and cared-for Midnight Cove beachside townhome with 2 master suites, walk-in closets, full sized washer and dryer, 2 expa...

2 Beds
2.5 Baths
Midnight Cove Ph 1 & 2 SubDv.
34242 Zip Code

5760 Midnight Pass Road Unit 103, Sarasota image

5760 Midnight Pass Road Unit 103, Sarasota — D $835,000

Are you ready to see an exceptional condo located in one of Siesta Keys most desirable resort communities? Now you can! This 2 bedroom,2 bath plus DEN condo in building ...

2 Beds
2 Baths
Gulf N Bay SubDv.
34242 Zip Code

1350 Siesta Bayside Drive Unit 1350-B, Sarasota image

1350 Siesta Bayside Drive Unit 1350-B, Sarasota — 1350 $675,000 ▼

Amazing vacation and/or investment property. ACT SOON and ENJOY all the rental INCOME for this season!!! Just across the street from world famous Siesta Beach with dedica...

3 Beds
2 Baths
Gulf & Bay Club Bayside SubDv.
34242 Zip Code

622 Tropical Circle, Sarasota $879,900

BEAUTIFUL Siesta Key home!! Fully remodeled modern home with ample upgrades throughout. A true coastal beauty!! Home is situated near the quaint village of Siesta Key and...

3 Beds
2 Baths
Siesta SubDv.
34242 Zip Code

20 Whispering Sands Drive Unit 1101, Sarasota image

20 Whispering Sands Drive Unit 1101, Sarasota — 20 $775,000

Paradise Alert! Welcome home to this beautifully furnished two-bedroom, two-bath Whispering Sands 11th floor corner end unit, perfectly situated in Siesta Key Village wit...

2 Beds
2 Baths
Whispering Sands SubDv.
34242 Zip Code

7712&7660 Sanderling Road, Sarasota image

7712&7660 Sanderling Road, Sarasota $12,900,000

Offering one of the area's most coveted lifestyles, this tropical sanctuary, known as Aquadisia, consists of just over 3 acres on the Gulf of Mexico in the coveted Sander...

3 Beds
3.5 Baths
Sanderling Club SubDv.
34242 Zip Code

1357 Moonmist Drive Unit T-4, Sarasota image

1357 Moonmist Drive Unit T-4, Sarasota — 1 $519,000

Within a short distance to the Intracoastal and the community's fishing pier, this beautiful "Blue Heron" 2/2 villa benefits from the majestic breezes and the sparkling l...

2 Beds
2 Baths
Polynesian Gardens SubDv.
34242 Zip Code

711 Mangrove Point Road, Sarasota $4,439,000

The tropical shores of Siesta Key set a stunning picture from this coastal traditional estate poised on one-and-a-half acres of botanical beauty. Within secluded South Co...

4 Beds
4.5 Baths
South Cocoanut Bayou SubDv.
34242 Zip Code

99 Island Circle, Sarasota $635,000

Beach cottage colors accent this mid-century 3 bed, 2 bath island home being offered turn-key furnished. Walk to #1 rated Siesta Beach from this 1713 SF home on a generou...

3 Beds
2 Baths
Sarasota Beach SubDv.
34242 Zip Code

746 Siesta Drive, Sarasota $2,000,000

Experience exceptional waterfront living and the island lifestyle on the coveted northern tip of Siesta Key, the choice for serious boaters who value deep water and quick...

6 Beds
3.5 Baths
Bay Island Shores SubDv.
34242 Zip Code

1102 Horizon View Drive, Sarasota $1,587,900

Combining elegance with the charm of coastal living, this four-bedroom home in Tortoise Estates is only moments away from the Sparkling Gulf waters of your private deeded...

4 Beds
3 Baths
Tortoise Estates SubDv.
34242 Zip Code

121 Vista Hermosa Circle Unit 46-B, Sarasota image

121 Vista Hermosa Circle Unit 46-B, Sarasota — Vista Hermosa $350,000

A private, secluded pied-a-terre on south Siesta Key is ideal for personal use, as an investment property (2 week minimum, 26 times per year), or as the perfect spot for ...

2 Beds
2 Baths
Vista Hermosa SubDv.
34242 Zip Code

1001 Point Of Rocks Road Unit 309, Sarasota image

1001 Point Of Rocks Road Unit 309, Sarasota — Building C $675,000

Paradise Awaits! This two bedroom two bathroom Gulf Front condo does not disappoint and is offered turnkey-furnished. With 1100 sgft of living area, this home has plenty ...

2 Beds
2 Baths
Sarasota Sands (Timeshare) SubDv.
34242 Zip Code

6300 Midnight Pass Road Unit 1004, Sarasota image

6300 Midnight Pass Road Unit 1004, Sarasota — 6300 $1,125,000

First time on the market in 40 years!This recently renovated 2 bed, 2 bath unit boasts one of the best views on Siesta Key. Whether you are an investor or a year- round r...

2 Beds
2 Baths
Crystal Sands SubDv.
34242 Zip Code

363 Avenida Milano, Sarasota $799,000

Siesta Key waterfront, minutes to Intracoastal Bay. 3/2 Mediterranean style home with easy access to the Siesta Village and being offered turn-key. A large pool with summ...

3 Beds
2 Baths
Siesta Manor SubDv.
34242 Zip Code

5830 Midnight Pass Road Unit 21, Sarasota image

5830 Midnight Pass Road Unit 21, Sarasota — 21 $415,000

Welcome home to this turnkey cozy beach cottage located on Siesta Key Beach! This spacious 1 bedroom allows the gardens views and pavered patio to carry the party outside...

1 Beds
1 Baths
Jamaica Royale SubDv.
34242 Zip Code

524 Beach Road Unit D, Sarasota — 524 Beach Rd $749,900

Location, Location, Location. Full Gulf views from this condo located in the heart of Siesta Key beach. This sits "Smack dab on the beach" with no roads to cross. Jus...

2 Beds
2 Baths
0524 Beach Road SubDv.
34242 Zip Code

1350 N Portofino Drive S Unit T109, Sarasota image

1350 N Portofino Drive S Unit T109, Sarasota — Tarpon House $369,900

Unusually Available! Fabulous Siesta Harbor First Floor No Steps! Unobstructed view of the canal and the main intercoastal waterway! Walk outside your lanai, directly to ...

2 Beds
2 Baths
Siesta Harbor SubDv.
34242 Zip Code

5855 Midnight Pass Road Unit 429, Sarasota image

5855 Midnight Pass Road Unit 429, Sarasota — Harbor Towers Y & R $549,000

Live the island life on beautiful Siesta Key and enjoy the finest of coastal living in this rarely available magnificent three bedroom, two bath condo. This spacious sout...

3 Beds
2 Baths
Harbor Towers Y & R SubDv.
34242 Zip Code

5045 Commonwealth Drive, Sarasota $695,000

SIESTA KEY. Come and see this well-constructed four bedroom, three and a half bath, pool home in the heart of Siesta Key. High ceilings, granite counters, two car garage,...

4 Beds
3.5 Baths
Siesta Beach SubDv.
34242 Zip Code

5760 Midnight Pass Road Unit 109D, Sarasota image

5760 Midnight Pass Road Unit 109D, Sarasota — D $729,000

Rare ground floor condo available at one of the most sought after complexes on Siesta Key. A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true...

2 Beds
2 Baths
Gulf & Bay Club SubDv.
34242 Zip Code

20 Whispering Sands Drive Unit 104, Sarasota image

20 Whispering Sands Drive Unit 104, Sarasota — Whispering Sands $589,000

This 2 BD/ 2 BA first floor condo gives you direct access from your lanai to the pool and onto the private crystal sand beach on the Gulf of Mexico. Whispering Sands offe...

2 Beds
2 Baths
Whispering Sands SubDv.
34242 Zip Code

1080 W Peppertree Lane Unit 406A, Sarasota image

1080 W Peppertree Lane Unit 406A, Sarasota — 1080 $720,000

AMAZING GULF & BEACH VIEWS! Own your own slice of Paradise just steps from the beach and enjoy beautiful sunsets from your 260 ft enclosed lanai, complete with newer wind...

2 Beds
2 Baths
Peppertree Bay SubDv.
34242 Zip Code

1202 Siesta Bayside Drive Unit 1202-C, Sarasota image

1202 Siesta Bayside Drive Unit 1202-C, Sarasota — 1202 $529,900

This is your opportunity to own in sought-after Gulf & Bay Club Bayside, a charming community with DEEDED beach access. Located in the heart of the island, Gulf & Bay Bay...

2 Beds
2 Baths
Gulf & Bay Club Bayside SubDv.
34242 Zip Code

1100 Cove Ii Place Unit 911, Sarasota image

1100 Cove Ii Place Unit 911, Sarasota — 9 $640,000

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. St...

2 Beds
2 Baths
Midnight Cove Ii SubDv.
34242 Zip Code

5516 Contento Drive, Sarasota $729,900

This Siesta Isles home features location second to none, an ample lot, and lots of possibilities! This classic Siesta Key home sits proudly overlooking a boat basin and c...

2 Beds
3 Baths
Siesta Isles SubDv.
34242 Zip Code

Sarasota $509,900

Rare opportunity to own a property located on Heron Lagoon on Siesta Key. Also, detached guest quarters. This property can be rented, remodeled, or as is. Adorable house ...

2 Beds
1 Baths
34242 Zip Code

5035 Sandy Beach Avenue, Sarasota $1,185,000

Welcome to your brand new home just minutes from the beach and downtown Siesta shops and restaurants! Set on a quiet street, this custom built, move-in ready home boasts ...

4 Beds
3.5 Baths
Siesta Beach SubDv.
34242 Zip Code

6600 Peacock Road Unit 107, Sarasota image

6600 Peacock Road Unit 107, Sarasota — 6600 $398,000

Welcome to Paradise Cove, a hidden gem on Siesta Key where everyday feels like a vacation. While the beaches are only moments away, this two-bedroom condominium is tucked...

2 Beds
2 Baths
Paradise Cove SubDv.
34242 Zip Code

1387 Moonmist Drive Unit G-2, Sarasota image

1387 Moonmist Drive Unit G-2, Sarasota — Na $450,000

Opportunity knocks! Do yourself a favor and check out this lowest priced Villa in Polynesian Gardens! Don't miss out on your chance to own a Piece of Paradise on Siesta K...

2 Beds
2 Baths
Polynesian Gardens SubDv.
34242 Zip Code

5964 Midnight Pass Road Unit 147, Sarasota image

5964 Midnight Pass Road Unit 147, Sarasota — 5964 $450,000

Epitomizing the essence of island living, this one-bedroom condominium is poised to enjoy all the tropical amenities of Siesta Key, home to what has been named the No. 1 ...

1 Beds
1.5 Baths
Palm Bay Club SubDv.
34242 Zip Code

1151 Lake House Circle Unit C-217, Sarasota image

1151 Lake House Circle Unit C-217, Sarasota — C-217 $499,000

Our House at the Beach can be YOUR House at the Beach! You'll be living the Idyllic Island Lifestyle as you stroll across the street to the #1 Beach in the U.S. to relax,...

2 Beds
2 Baths
Our House At The Bch SubDv.
34242 Zip Code

3460 Seagrape Drive, Sarasota $425,000

One of the last buildable vacant parcels on the north end of Siesta Key. This lot is in an area of multi million $$ homes with a fantastic location just two blocks from ...

Bay Island SubDv.
34242 Zip Code

5129 Sandy Cove Avenue, Siesta Key image

5129 Sandy Cove Avenue, Siesta Key — 5129 $1,399,900

Beautifully Remodeled, Siesta Key's waterfront home, Located on a quiet cul-de-sac on boating water, this 4 bedroom, 3 bath home will delight . Custom kitchen, with high ...

4 Beds
3 Baths
Sara Sands SubDv.
34242 Zip Code

6480 Midnight Pass Road Unit 203, Sarasota image

6480 Midnight Pass Road Unit 203, Sarasota — Siesta Breakers $799,000

Own a part of paradise and live on the pristine quartz sandy beach of Siesta Key. Inside your 2nd floor condo have lunch on the lanai overlooking the pool, garden, and Gu...

2 Beds
2 Baths
Siesta Breakers SubDv.
34242 Zip Code

254 Garden Lane, Sarasota $599,000

Key West style home located on a canal on Siesta Key. Located in an enclave of lush tropical landscaping! Home has been re-piped, new kitchen sink, faucet, bathroom sink,...

2 Beds
1 Baths
Siesta Rev SubDv.
34242 Zip Code

5911 Midnight Pass Road Unit 305, Sarasota image

5911 Midnight Pass Road Unit 305, Sarasota — 5911 $629,900

Ready to impress even the finest buyer! Luxury residence with full direct water views, open and split floor plan. Located on the bay side of Florida’s barrier Island -Sie...

2 Beds
2 Baths
Boca Siesta SubDv.
34242 Zip Code

5760 Midnight Pass Road Unit 609, Sarasota image

5760 Midnight Pass Road Unit 609, Sarasota — D $915,000

Beautiful Gulf views from this Stunning remodel at Gulf & Bay Club in the heart of Siesta Key. This turnkey furnished unit is one of the best units in the entire "D" ...

2 Beds
2 Baths
Gulf & Bay Club SubDv.
34242 Zip Code

6157 Midnight Pass Road Unit E01, Sarasota image

6157 Midnight Pass Road Unit E01, Sarasota — Bldg E $357,000

Spectacular first floor condo (no steps or elevator to deal with here. Just walk in). Great rental history - 2018 gross income $29,670, 2017 gross income $32,357, 2016 gr...

2 Beds
2 Baths
Bay Oaks Estates SubDv.
34242 Zip Code

5066 Sandy Beach Avenue, Sarasota $849,900

Waterfront property in the neighborhood of Sara Sands. Beautifully remodeled picture-perfect home conveniently located on North Siesta close to the Siesta Key Village and...

4 Beds
2.5 Baths
Sara Sands SubDv.
34242 Zip Code

414 Island Circle, Sarasota $1,575,000

Siesta Key beach-house + boating retreat! 3/3 with den and 2-car garage. Recently renovated and being sold turn-key. Major recent improvements: new roof, dock with a lift...

3 Beds
3 Baths
Sarasota Beach SubDv.
34242 Zip Code

5966 Midnight Pass Road Unit G-101, Sarasota image

5966 Midnight Pass Road Unit G-101, Sarasota — 5966 $1,350,000

Live at the beach in this stunning two-bedroom residence at Palm Bay Club where turquoise waters and white sands are your daily backdrop. Located on the tenth floor in th...

2 Beds
2 Baths
Palm Bay Club SubDv.
34242 Zip Code

4822 Ocean Boulevard Unit 5F, Sarasota image

4822 Ocean Boulevard Unit 5F, Sarasota — Siesta Towers $599,000

SIESTA KEY - SIESTA TOWERS - Full GULF VIEWS, The Perfect Siesta Key location, close to Siesta Key Beach, close to Siesta Key Village and an easy on /and off the Island t...

2 Beds
2 Baths
Siesta Towers SubDv.
34242 Zip Code

9240 Midnight Pass Road Unit D, Sarasota image

9240 Midnight Pass Road Unit D, Sarasota — Mangrove Bay $749,000

Great Buy On Siesta Key!! Tastefully and Fully Updated throughout county records say built in 2011. With these Full water views from every level of all 5 balconies makes ...

3 Beds
2.5 Baths
Starlite Roof SubDv.
34242 Zip Code

7208 Melaleuca Way, Sarasota $2,449,000

Crowning an acre+ in one of Siesta Key’s most beloved deeded beach access neighborhoods, Sanderling Club. Skip the wait of building with this magnificent single-level 201...

4 Beds
4.5 Baths
Sanderling Club SubDv.
34242 Zip Code

Lot 21 Midnight Pass Road, Sarasota image

Lot 21 Midnight Pass Road, Sarasota $389,000

Siesta Key! Build the home of your dreams on this 12,320 sq. ft. cleared lot located just across the street from the beautiful Gulf of Mexico. Property includes your own ...

Tortoise Estates SubDv.
34242 Zip Code