• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

The Wendy Lynn Group: Sarasota Homes and Condos

The Wendy Lynn Group - www.SarasotaHomesandCondos.com

  • Home Search
  • Areas
  • Featured Listings
    • Sold Listings
  • Selling
  • Blog
  • About
    • Wendy Lynn
    • Josh Lynn
    • Testimonials
  • Contact
  • Email
  • Facebook
  • Instagram
  • LinkedIn
  • Phone
  • Pinterest
  • Twitter
  • YouTube

Real Estate Search

You are here: Home / Siesta Isles in Siesta Key : Homes for Sale in a Waterfront Community

Siesta Isles in Siesta Key : Homes for Sale in a Waterfront Community

The Siesta Key housing market has more to offer athan imposing beachfront condo towers; if you are looking for a quiet residential setting where you can enjoy boating, fishing and raising a family, Siesta Isles is highly recommended. Located between Hidden Harbor Road and Beach Road, Siesta Isles in Siesta Key is a large neighborhood that tourists do not get to see unless they venture to explore beyond the public beaches.  Initially developed in the 1960s, Siesta Isles is a feat of engineering that initially involved years of dredging for the purpose of creating deepwater canals connecting to Roberts Bay.

Siesta Isles evokes an ambiance that combines Old Florida charm with the feeling of a Caribbean resort. With a four-mile network of canals, nearly three-quarters of all properties are guaranteed waterfront views or private docking space. If you see a listing with a Contento Street or Azure way address, you can be assured of waterfront property because those two roads are within islands.

Unlike other subdivisions in Siesta Key, the homes at Siesta Isles enjoy generous home sites measuring between 12,000 and 16,000 square feet. Architectural styles range from Florida ranches built in the late 1960s to remodeled properties that have been turned into Mediterranean revival estates. Pricing starts at $595K for a two-bedroom Florida ranch located just a block away from a canal and three blocks from the beach. Once you start looking at waterfront homes with private docking space, covered swimming pool, and three bedrooms, you can find prices below $800K, which is very reasonable when considering the location.

To get an idea of how close boaters are to Roberts Bay and the Intracoastal Waterway, even those living in the southern section of Siesta Isles can exit Siesta Key in about 20 minutes. Residents who live on the bay side of the neighborhood can walk to the beach in 10 minutes, and this is how long it takes to the restaurants, pubs and neighborhood markets along Ocean Boulevard. For more comprehensive shopping, driving to the Publix supermarket at Sarasota Pavilion takes about 11 minutes. The Downtown Sarasota arts and culture districts are just 15 minutes away.

Homes for Sale at Siesta Isles in Siesta Key

  • List View
  • Map View
  • Grid View
  • 1038 Contento Street, Sarasota, FL
    1038 Contento Street
    Sarasota, FL
    Photo of 1038 Contento Street, Sarasota, FL 34242 (MLS # A4650938)
    $1,725,000
    • Lot Size
      13,504 sqft

    • Home Size
      2,217 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1972

    • Days on Market
      9

    View Virtual Tour
  • 734 Canal Road, Sarasota, FL
    734 Canal Road
    Sarasota, FL
    Photo of 734 Canal Road, Sarasota, FL 34242 (MLS # A4651051)
    $1,000,000
    • Lot Size
      12,197 sqft

    • Home Size
      1,412 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1963

    • Days on Market
      15

    View Virtual Tour
  • 5502 Shadow Lawn Drive, Sarasota, FL
    5502 Shadow Lawn Drive
    Sarasota, FL
    Photo of 5502 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4649470)
    $1,399,000
    • Lot Size
      14,375 sqft

    • Home Size
      2,337 sqft

    • Beds
      3 Beds

    • Baths
      4 Baths

    • Year Built
      1961

    • Days on Market
      22

    View Virtual Tour
  • 5432 Cape Leyte Drive, Sarasota, FL
    5432 Cape Leyte Drive
    Sarasota, FL
    Photo of 5432 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4649500)
    $1,295,000
    • Lot Size
      14,811 sqft

    • Home Size
      1,659 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1974

    • Days on Market
      29

    View Virtual Tour
  • 1014 Contento Street, Sarasota, FL
    1014 Contento Street
    Sarasota, FL
    Photo of 1014 Contento Street, Sarasota, FL 34242 (MLS # A4650604)
    $1,580,000
    • Lot Size
      13,504 sqft

    • Home Size
      2,397 sqft

    • Beds
      4 Beds

    • Baths
      4 Baths

    • Year Built
      1969

    • Days on Market
      41

    View Virtual Tour
  • 5525 Shadow Lawn Drive, Sarasota, FL
    5525 Shadow Lawn Drive
    Sarasota, FL
    Photo of 5525 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4642030)
    $1,195,000
    • Lot Size
      13,504 sqft

    • Home Size
      1,644 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1964

    • Days on Market
      79

    View Virtual Tour
  • 927 Contento Street, Sarasota, FL
    927 Contento Street
    Sarasota, FL
    Photo of 927 Contento Street, Sarasota, FL 34242 (MLS # A4640177)
    $3,995,000
    • Lot Size
      11,762 sqft

    • Home Size
      3,649 sqft

    • Beds
      4 Beds

    • Baths
      4 Baths

    • Year Built
      2024

    • Days on Market
      92

    View Virtual Tour
  • 5376 Shadow Lawn Drive, Sarasota, FL
    5376 Shadow Lawn Drive
    Sarasota, FL
    Photo of 5376 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4634690)
    $2,200,000
    • Lot Size
      13,940 sqft

    • Home Size
      3,721 sqft

    • Beds
      4 Beds

    • Baths
      5 Baths

    • Year Built
      1964

    • Days on Market
      103

  • 951 Contento St. St, Siesta Key, FL
    951 Contento St. St
    Siesta Key, FL
    Photo of 951 Contento St. St, Siesta Key, FL 34242 (MLS # A4639209)
    $2,299,000
    • Lot Size
      11,762 sqft

    • Home Size
      2,882 sqft

    • Beds
      3 Beds

    • Baths
      4 Baths

    • Year Built
      1967

    • Days on Market
      117

    View Virtual Tour
  • 5560 Shadow Lawn Drive, Sarasota, FL
    5560 Shadow Lawn Drive
    Sarasota, FL
    Photo of 5560 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4636955)
    $1,695,000
    • Lot Size
      14,375 sqft

    • Home Size
      2,124 sqft

    • Beds
      4 Beds

    • Baths
      3 Baths

    • Year Built
      1970

    • Days on Market
      133

    View Virtual Tour

See all Siesta Isles Siesta Key Homes for Sale.
(all data current as of 5/15/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.

 
 

Primary Sidebar

The Lynn Group - Wendy Lynn - eXp Sarasota

eXp Realty
Phone: (941) 421-7375
E-mail Us!

Siesta Key Neighborhoods & Condo Communities

  • Aloha Kai
  • Anchorage
  • Bay Island
  • Bay Oaks
  • Bay Tree Club
  • Bayou Louise
  • Beach Club
  • Beach Villas
  • Beach Way
  • Boca Siesta Bayside
  • Casarina
  • Casa Blanca Villas
  • Casa Mar
  • Cocoanut Bayou
  • Continentals Sea Club
  • Coquille
  • The Crescent
  • Crescent Arms
  • Crescent Royale
  • Crystal Sands
  • Dolphin Bay
  • El Presidente
  • Excelsior
  • Fiddler Bayou
  • Fishermans Cove
  • Fishermans Haven
  • Grand Siesta
  • Gulf & B C Bayside
  • Gulf & Bay Club
  • Gulfmead Estates
  • Hamilton Club
  • Harbor Towers
  • Harbour Towne
  • Harmony
  • Hidden Harbor
  • Horizons West
  • House of the Sun
  • Hyatt Siesta Beach
  • Island House
  • Island Reef
  • Jamaica Royale
  • La Siesta
  • Lands End
  • Mangroves
  • Marina Del Sol
  • Midnight Cove
  • Midnight Sea
  • Mira-Mar Beach
  • Moorings
  • Ocean Beach
  • Ocean View
  • Our House at the Beach
  • Palm Bay Club
  • Peppertree
  • Point Crisp
  • Point of Rocks
  • Pointe on Midnight Pass
  • Polynesian Gardens
  • Provincial Gardens
  • Riegels Landing
  • Roberts Point
  • Royal Palm Harbor
  • Sanderling Club
  • Sandy Cove
  • Sandy Hook
  • Sara Sands
  • Sarasota Beach
  • Sarasota Surf & Racquet
  • Sea Breeze
  • Sea Grove
  • Sea Shell
  • Sea Village
  • Sea Winds
  • Siesta Bayside
  • Siesta Beach
  • Siesta Beach House
  • Siesta Breakers
  • Siesta Cove
  • Siesta Dunes
  • Siesta Estates
  • Siesta Harbor
  • Siesta Isles
  • Siesta Manor
  • Siesta Rev
  • Siesta Sands
  • Siesta Sun
  • Siesta Towers
  • Siesta Villa
  • Siestas Waterside
  • Solymar
  • Somerset Cay
  • Somerset Cove
  • South Siesta Key
  • Spice Bay
  • Summer Cove on Siesta
  • Sunset Royale
  • Tiffany Sands
  • Terrace
  • Terrace East
  • Tivoli by the Sea
  • Tortoise Estates
  • Tortuga
  • Turtle Bay
  • Turtle Beach
  • Turtle Cove
  • Twin Palms
  • Vista Hermosa
  • Windward Passage
  • Whispering Sands
  • White Sands Village

Areas We Serve

  • Anna Maria Island
  • Bird Key
  • Bradenton
  • Bradenton Beach
  • Casey Key
  • Cortez
  • Downtown Sarasota
  • Ellenton
  • Englewood
  • Golden Gate
  • Holmes Beach
  • Lakewood Ranch
  • Lido Key
  • Longboat Key
  • Nokomis
  • North Port
  • Osprey
  • Palmer Ranch
  • Palmetto
  • Parrish
  • Sarasota
  • Siesta Key
  • Terra Ceia
  • University Park
  • Venice
  • West of the Trail

Things to do in Siesta Key

https://www.youtube.com/watch?v=jwx88CpiL0M&t=37s

Footer

The Lynn Group - Wendy Lynn - eXp Sarasota

eXp Realty
Phone: (941) 421-7375
E-mail Us!

Connect with Us!

  • Email
  • Facebook
  • Instagram
  • LinkedIn
  • Phone
  • Pinterest
  • Twitter
  • YouTube

Latest Real Estate

  • $335,000 904 Winter Garden Drive
    Sarasota, FL
  • $186,000 1758 35th Street
    Sarasota, FL
  • $299,900 8849 Attalla Avenue
    North Port, FL
  • $265,000 8105 Grand Estuary Trail #105
    Bradenton, FL
  • $1,700,000 3018 Gulf Drive
    Holmes Beach, FL
  • $1,300,000 208 Peacock Lane
    Holmes Beach, FL
  • $599,000 2745 62nd Avenue E
    Ellenton, FL
  • $739,995 1311 Siesta Bayside Drive #1311-A
    Sarasota, FL
  • $1,650,000 1255 N Gulfstream Avenue #402
    Sarasota, FL
  • $299,000 3421 70th Avenue E
    Ellenton, FL
  • $1,995,000 2485 S Milmar Drive
    Sarasota, FL
  • $6,900,000 5132 Jungle Plum Road
    Sarasota, FL
  • $424,990 4625 Arden Way
    Lakewood Ranch, FL
  • $390,000 907 63rd Avenue W #907 & 909
    Bradenton, FL
  • $350,000 3003 58th Way E
    Palmetto, FL
  • $360,000 5407 Kedgewick Lane
    North Port, FL
  • $439,999 4621 34th Court E
    Bradenton, FL
  • $497,500 1745 Hyssop Loop
    North Port, FL
  • $378,990 10721 Hidden Banks Glen
    Parrish, FL
  • $376,990 10722 Hidden Banks Glen
    Parrish, FL
904 Winter Garden Drive
Sarasota, FL
Photo of 904 Winter Garden Drive, Sarasota, FL 34243 (MLS # A4652416)
$335,000
Lot Size
10,455 sqft

Home Size
1,222 sqft

Beds
3 Beds

Baths
2 Baths

1758 35th Street
Sarasota, FL
Photo of 1758 35th Street, Sarasota, FL 34234 (MLS # A4652687)
$186,000
Lot Size
5,228 sqft

Home Size
979 sqft

Beds
3 Beds

Baths
1 Bath

8849 Attalla Avenue
North Port, FL
Photo of 8849 Attalla Avenue, North Port, FL 34287 (MLS # C7509994)
$299,900
Lot Size
10,019 sqft

Home Size
1,261 sqft

Beds
3 Beds

Baths
2 Baths

8105 Grand Estuary Trail #105
Bradenton, FL
Photo of 8105 Grand Estuary Trail #105, Bradenton, FL 34212 (MLS # A4652339)
$265,000
Lot Size
N/A

Home Size
1,121 sqft

Beds
2 Beds

Baths
2 Baths

3018 Gulf Drive
Holmes Beach, FL
Photo of 3018 Gulf Drive, Holmes Beach, FL 34217 (MLS # A4651692)
$1,700,000
Lot Size
5,228 sqft

Home Size
2,320 sqft

Beds
N/A

Baths
N/A

208 Peacock Lane
Holmes Beach, FL
Photo of 208 Peacock Lane, Holmes Beach, FL 34217 (MLS # A4651677)
$1,300,000
Lot Size
7,841 sqft

Home Size
1,738 sqft

Beds
N/A

Baths
N/A

2745 62nd Avenue E
Ellenton, FL
Photo of 2745 62nd Avenue E, Ellenton, FL 34222 (MLS # A4652457)
$599,000
Lot Size
6,099 sqft

Home Size
3,027 sqft

Beds
5 Beds

Baths
3 Baths

1311 Siesta Bayside Drive #1311-A
Sarasota, FL
Photo of 1311 Siesta Bayside Drive #1311-A, Sarasota, FL 34242 (MLS # A4652576)
$739,995
Lot Size
N/A

Home Size
1,130 sqft

Beds
2 Beds

Baths
2 Baths

1255 N Gulfstream Avenue #402
Sarasota, FL
Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4649907)
$1,650,000
Lot Size
1.55 ac

Home Size
2,064 sqft

Beds
3 Beds

Baths
3 Baths

3421 70th Avenue E
Ellenton, FL
Photo of 3421 70th Avenue E, Ellenton, FL 34222 (MLS # A4652160)
$299,000
Lot Size
6,970 sqft

Home Size
1,296 sqft

Beds
3 Beds

Baths
2 Baths

2485 S Milmar Drive
Sarasota, FL
Photo of 2485 S Milmar Drive, Sarasota, FL 34237 (MLS # A4652094)
$1,995,000
Lot Size
10,455 sqft

Home Size
2,876 sqft

Beds
4 Beds

Baths
4 Baths

5132 Jungle Plum Road
Sarasota, FL
Photo of 5132 Jungle Plum Road, Sarasota, FL 34242 (MLS # A4651663)
$6,900,000
Lot Size
22,652 sqft

Home Size
6,928 sqft

Beds
5 Beds

Baths
7 Baths

4625 Arden Way
Lakewood Ranch, FL
Photo of 4625 Arden Way, Lakewood Ranch, FL 34211 (MLS # W7875550)
$424,990
Lot Size
4,792 sqft

Home Size
1,848 sqft

Beds
3 Beds

Baths
3 Baths

907 63rd Avenue W #907 & 909
Bradenton, FL
Photo of 907 63rd Avenue W #907 & 909, Bradenton, FL 34207 (MLS # TB8386131)
$390,000
Lot Size
13,940 sqft

Home Size
1,944 sqft

Beds
4 Beds

Baths
4 Baths

3003 58th Way E
Palmetto, FL
Photo of 3003 58th Way E, Palmetto, FL 34221 (MLS # N6138890)
$350,000
Lot Size
7,406 sqft

Home Size
1,417 sqft

Beds
3 Beds

Baths
2 Baths

5407 Kedgewick Lane
North Port, FL
Photo of 5407 Kedgewick Lane, North Port, FL 34288 (MLS # TB8386032)
$360,000
Lot Size
11,762 sqft

Home Size
1,984 sqft

Beds
5 Beds

Baths
3 Baths

4621 34th Court E
Bradenton, FL
Photo of 4621 34th Court E, Bradenton, FL 34203 (MLS # A4652634)
$439,999
Lot Size
10,019 sqft

Home Size
2,271 sqft

Beds
4 Beds

Baths
2 Baths

1745 Hyssop Loop
North Port, FL
Photo of 1745 Hyssop Loop, North Port, FL 34289 (MLS # C7509158)
$497,500
Lot Size
6,970 sqft

Home Size
1,997 sqft

Beds
3 Beds

Baths
2 Baths

10721 Hidden Banks Glen
Parrish, FL
Photo of 10721 Hidden Banks Glen, Parrish, FL 34219 (MLS # A4652632)
$378,990
Lot Size
6,970 sqft

Home Size
2,260 sqft

Beds
4 Beds

Baths
3 Baths

10722 Hidden Banks Glen
Parrish, FL
Photo of 10722 Hidden Banks Glen, Parrish, FL 34219 (MLS # A4652630)
$376,990
Lot Size
6,099 sqft

Home Size
2,260 sqft

Beds
4 Beds

Baths
3 Baths

  • 904 Winter Garden Drive
    Sarasota, FL
    Photo of 904 Winter Garden Drive, Sarasota, FL 34243 (MLS # A4652416)
    $335,000
    Lot Size
    10,455 sqft

    Home Size
    1,222 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 1758 35th Street
    Sarasota, FL
    Photo of 1758 35th Street, Sarasota, FL 34234 (MLS # A4652687)
    $186,000
    Lot Size
    5,228 sqft

    Home Size
    979 sqft

    Beds
    3 Beds

    Baths
    1 Bath

  • 8849 Attalla Avenue
    North Port, FL
    Photo of 8849 Attalla Avenue, North Port, FL 34287 (MLS # C7509994)
    $299,900
    Lot Size
    10,019 sqft

    Home Size
    1,261 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 8105 Grand Estuary Trail #105
    Bradenton, FL
    Photo of 8105 Grand Estuary Trail #105, Bradenton, FL 34212 (MLS # A4652339)
    $265,000
    Lot Size
    N/A

    Home Size
    1,121 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 3018 Gulf Drive
    Holmes Beach, FL
    Photo of 3018 Gulf Drive, Holmes Beach, FL 34217 (MLS # A4651692)
    $1,700,000
    Lot Size
    5,228 sqft

    Home Size
    2,320 sqft

    Beds
    N/A

    Baths
    N/A

  • 208 Peacock Lane
    Holmes Beach, FL
    Photo of 208 Peacock Lane, Holmes Beach, FL 34217 (MLS # A4651677)
    $1,300,000
    Lot Size
    7,841 sqft

    Home Size
    1,738 sqft

    Beds
    N/A

    Baths
    N/A

  • 2745 62nd Avenue E
    Ellenton, FL
    Photo of 2745 62nd Avenue E, Ellenton, FL 34222 (MLS # A4652457)
    $599,000
    Lot Size
    6,099 sqft

    Home Size
    3,027 sqft

    Beds
    5 Beds

    Baths
    3 Baths

  • 1311 Siesta Bayside Drive #1311-A
    Sarasota, FL
    Photo of 1311 Siesta Bayside Drive #1311-A, Sarasota, FL 34242 (MLS # A4652576)
    $739,995
    Lot Size
    N/A

    Home Size
    1,130 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 1255 N Gulfstream Avenue #402
    Sarasota, FL
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4649907)
    $1,650,000
    Lot Size
    1.55 ac

    Home Size
    2,064 sqft

    Beds
    3 Beds

    Baths
    3 Baths

  • 3421 70th Avenue E
    Ellenton, FL
    Photo of 3421 70th Avenue E, Ellenton, FL 34222 (MLS # A4652160)
    $299,000
    Lot Size
    6,970 sqft

    Home Size
    1,296 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 2485 S Milmar Drive
    Sarasota, FL
    Photo of 2485 S Milmar Drive, Sarasota, FL 34237 (MLS # A4652094)
    $1,995,000
    Lot Size
    10,455 sqft

    Home Size
    2,876 sqft

    Beds
    4 Beds

    Baths
    4 Baths

  • 5132 Jungle Plum Road
    Sarasota, FL
    Photo of 5132 Jungle Plum Road, Sarasota, FL 34242 (MLS # A4651663)
    $6,900,000
    Lot Size
    22,652 sqft

    Home Size
    6,928 sqft

    Beds
    5 Beds

    Baths
    7 Baths

  • 4625 Arden Way
    Lakewood Ranch, FL
    Photo of 4625 Arden Way, Lakewood Ranch, FL 34211 (MLS # W7875550)
    $424,990
    Lot Size
    4,792 sqft

    Home Size
    1,848 sqft

    Beds
    3 Beds

    Baths
    3 Baths

  • 907 63rd Avenue W #907 & 909
    Bradenton, FL
    Photo of 907 63rd Avenue W #907 & 909, Bradenton, FL 34207 (MLS # TB8386131)
    $390,000
    Lot Size
    13,940 sqft

    Home Size
    1,944 sqft

    Beds
    4 Beds

    Baths
    4 Baths

  • 3003 58th Way E
    Palmetto, FL
    Photo of 3003 58th Way E, Palmetto, FL 34221 (MLS # N6138890)
    $350,000
    Lot Size
    7,406 sqft

    Home Size
    1,417 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 5407 Kedgewick Lane
    North Port, FL
    Photo of 5407 Kedgewick Lane, North Port, FL 34288 (MLS # TB8386032)
    $360,000
    Lot Size
    11,762 sqft

    Home Size
    1,984 sqft

    Beds
    5 Beds

    Baths
    3 Baths

  • 4621 34th Court E
    Bradenton, FL
    Photo of 4621 34th Court E, Bradenton, FL 34203 (MLS # A4652634)
    $439,999
    Lot Size
    10,019 sqft

    Home Size
    2,271 sqft

    Beds
    4 Beds

    Baths
    2 Baths

  • 1745 Hyssop Loop
    North Port, FL
    Photo of 1745 Hyssop Loop, North Port, FL 34289 (MLS # C7509158)
    $497,500
    Lot Size
    6,970 sqft

    Home Size
    1,997 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 10721 Hidden Banks Glen
    Parrish, FL
    Photo of 10721 Hidden Banks Glen, Parrish, FL 34219 (MLS # A4652632)
    $378,990
    Lot Size
    6,970 sqft

    Home Size
    2,260 sqft

    Beds
    4 Beds

    Baths
    3 Baths

  • 10722 Hidden Banks Glen
    Parrish, FL
    Photo of 10722 Hidden Banks Glen, Parrish, FL 34219 (MLS # A4652630)
    $376,990
    Lot Size
    6,099 sqft

    Home Size
    2,260 sqft

    Beds
    4 Beds

    Baths
    3 Baths

Previous Next
 
  • © 2010–2025
  • SARASOTA HOMES & CONDOS SITEMAP
  • HOME PAGE