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You are here: Home / Windward Bay at Longboat Key : Bayside Condos for Sale with Amenities

Windward Bay at Longboat Key : Bayside Condos for Sale with Amenities

Windward Bay at Longboat Key offers Bayside Condos for Sale in a Gated Community. Near Bradenton, Sarasota, Golf & St Armands Circle. Amenities include a Pool, Tennis Courts, Boat Docks & More.

Windward Bay at Longboat Key Amenities

Condos for Sale at Windward Bay in Longboat Key

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  • 4500 Gulf Of Mexico Drive #PH4, Longboat Key, FL
    4500 Gulf Of Mexico Drive #PH4
    Longboat Key, FL
    Photo of 4500 Gulf Of Mexico Drive #PH4, Longboat Key, FL 34228 (MLS # A4649405)
    $675,000
    • Lot Size

    • Home Size
      1,312 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      42

    View Virtual Tour
  • 4800 Gulf Of Mexico Drive #204, Longboat Key, FL
    4800 Gulf Of Mexico Drive #204
    Longboat Key, FL
    Photo of 4800 Gulf Of Mexico Drive #204, Longboat Key, FL 34228 (MLS # A4650568)
    $650,000
    • Lot Size

    • Home Size
      1,325 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      49

    View Virtual Tour
  • 4840 Gulf Of Mexico Drive #Villa 15, Longboat Key, FL
    4840 Gulf Of Mexico Drive #Villa 15
    Longboat Key, FL
    Photo of 4840 Gulf Of Mexico Drive #Villa 15, Longboat Key, FL 34228 (MLS # A4652683)
    $569,900
    • Lot Size
      26.67 ac

    • Home Size
      1,084 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1974

    • Days on Market
      54

    View Virtual Tour
  • 4800 Gulf Of Mexico Drive #205, Longboat Key, FL
    4800 Gulf Of Mexico Drive #205
    Longboat Key, FL
    Photo of 4800 Gulf Of Mexico Drive #205, Longboat Key, FL 34228 (MLS # A4649789)
    $799,000
    • Lot Size
      26.67 ac

    • Home Size
      1,325 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      59

    View Virtual Tour
  • 4760 Gulf Of Mexico Dr. Villa 7, Longboat Key, FL
    4760 Gulf Of Mexico Dr. Villa 7
    Longboat Key, FL
    Photo of 4760 Gulf Of Mexico Dr. Villa 7, Longboat Key, FL 34228 (MLS # A4646680)
    $595,000
    • Lot Size
      26.67 ac

    • Home Size
      931 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1974

    • Days on Market
      79

    View Virtual Tour
  • 4968 Gulf Of Mexico Drive #Villa 22, Longboat Key, FL
    4968 Gulf Of Mexico Drive #Villa 22
    Longboat Key, FL
    Photo of 4968 Gulf Of Mexico Drive #Villa 22, Longboat Key, FL 34228 (MLS # A4650036)
    $1,200,000
    • Lot Size
      26.13 ac

    • Home Size
      1,422 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1974

    • Days on Market
      83

  • 4600 Gulf Of Mexico Drive #202, Longboat Key, FL
    4600 Gulf Of Mexico Drive #202
    Longboat Key, FL
    Photo of 4600 Gulf Of Mexico Drive #202, Longboat Key, FL 34228 (MLS # A4642183)
    $590,000
    • Lot Size
      21.13 ac

    • Home Size
      1,312 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      111

    View Virtual Tour
  • 4600 Gulf Of Mexico Drive #206, Longboat Key, FL
    4600 Gulf Of Mexico Drive #206
    Longboat Key, FL
    Photo of 4600 Gulf Of Mexico Drive #206, Longboat Key, FL 34228 (MLS # A4636663)
    $800,000
    • Lot Size
      26.67 ac

    • Home Size
      1,523 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      147

    View Virtual Tour
  • 4900 Gulf Of Mexico Drive #205, Longboat Key, FL
    4900 Gulf Of Mexico Drive #205
    Longboat Key, FL
    Photo of 4900 Gulf Of Mexico Drive #205, Longboat Key, FL 34228 (MLS # A4632746)
    $725,000
    • Lot Size

    • Home Size
      1,312 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      168

    View Virtual Tour
  • 4800 Gulf Of Mexico Drive #PH 3, Longboat Key, FL
    4800 Gulf Of Mexico Drive #PH 3
    Longboat Key, FL
    Photo of 4800 Gulf Of Mexico Drive #PH 3, Longboat Key, FL 34228 (MLS # A4633460)
    $599,900
    • Lot Size
      26.00 ac

    • Home Size
      1,312 sqft

    • Beds
      2 Beds

    • Baths
      2 Baths

    • Year Built
      1975

    • Days on Market
      172

    View Virtual Tour

See all Windward Bay Longboat Key Condos for Sale.
(all data current as of 6/16/2025)

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

 
 

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The Lynn Group - Wendy Lynn - eXp Sarasota

  • 1540 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • Email Us

Longboat Key Neighborhoods & Condo Communities

  • Aquarius Club
  • Aria
  • Banyan Bay
  • Bay Harbour
  • Bay Isles
  • Bayview Estates
  • Bayport
  • Beach Castle
  • Beach Harbor Club
  • Beaches Of LBK
  • Beachplace
  • Beachcomber
  • Bleu Claire
  • Boathouse on LBK
  • Buttonwood Cove
  • Buttonwood Harbour
  • Cabana Beach
  • Casa del Mar
  • Castillian
  • Cedars
  • Club Longboat
  • Conrad Beach
  • Coreys Landing
  • Covert
  • Country Club Shores
  • Diplomat
  • Dream Island
  • Emerald Harbor
  • En Provence
  • Fairway Bay
  • First Longboat Harbour
  • Grand Bay
  • Grand Mariner
  • Harbour Oaks
  • Harbour Court
  • Harbour Villa Club
  • Hideaway Bay
  • Infinity LBK
  • Inn on the Beach
  • Islander Club
  • Islands West
  • L Ambiance
  • La Playa
  • Laguna Yacht
  • Longbeach
  • Longboat Beach
  • Longboat Cove
  • Longboat Harbour
  • Longboat Harbour Towers
  • Longboat Key Club
  • LBK Moorings
  • Longboat Key Towers
  • LBK Yacht Club
  • Longboat Pass
  • Longboat Shores
  • Marina Bay
  • Pelican Harbour
  • Pierre
  • Players Club
  • Portobello
  • Positano
  • Privateer
  • Promenade
  • Queens Harbour
  • Reclinata
  • Regent Place
  • Sabal Cove
  • Sands Point
  • Sanctuary
  • Sea Gate Club
  • Sea Pines Condo
  • Sea Twig
  • Seaplace
  • Silver Sands
  • Shore Condo
  • Sleepy Lagoon
  • Spanish Main YC
  • Sunset Beach
  • Sutton Place
  • Tangerine Bay
  • Triton Bend
  • Turtle Crawl Condo
  • Villa Di Lancia
  • Vizcaya
  • Water Club
  • Westchester
  • Weston Pointe
  • Whitney Beach
  • Winding Oaks
  • Windward Bay

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 Longboat Key

https://www.youtube.com/watch?v=PvxuAZ5k20k

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  • 941-421-7375
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Latest Real Estate

  • $329,945 3305 Notre Dame Place #3305
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3305 Notre Dame Place #3305
Bradenton, FL
Photo of 3305 Notre Dame Place #3305, Bradenton, FL 34207 (MLS # A4655891)
$329,945
Lot Size
3,921 sqft

Home Size
1,230 sqft

Beds
2 Beds

Baths
2 Baths

4802 51st Street W #1313
Bradenton, FL
Photo of 4802 51st Street W #1313, Bradenton, FL 34210 (MLS # A4656007)
$170,000
Lot Size
39.01 ac

Home Size
750 sqft

Beds
1 Bed

Baths
1 Bath

1559 Running Tide Place
Sarasota, FL
Photo of 1559 Running Tide Place, Sarasota, FL 34240 (MLS # TB8397341)
$1,169,990
Lot Size
5,663 sqft

Home Size
2,847 sqft

Beds
4 Beds

Baths
4 Baths

7750 Ridgelake Circle
Bradenton, FL
Photo of 7750 Ridgelake Circle, Bradenton, FL 34203 (MLS # A4656001)
$468,000
Lot Size
7,406 sqft

Home Size
1,622 sqft

Beds
3 Beds

Baths
2 Baths

19023 Mangieri Street
Venice, FL
Photo of 19023 Mangieri Street, Venice, FL 34293 (MLS # A4655980)
$425,000
Lot Size
6,099 sqft

Home Size
1,437 sqft

Beds
2 Beds

Baths
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1224 38th Street W
Bradenton, FL
Photo of 1224 38th Street W, Bradenton, FL 34205 (MLS # A4656002)
$275,000
Lot Size
10,019 sqft

Home Size
936 sqft

Beds
2 Beds

Baths
1 Bath

4745 Trout River Crossing
Ellenton, FL
Photo of 4745 Trout River Crossing, Ellenton, FL 34222 (MLS # TB8397326)
$474,000
Lot Size
9,148 sqft

Home Size
2,035 sqft

Beds
3 Beds

Baths
2 Baths

4531 Useppa Drive
Bradenton, FL
Photo of 4531 Useppa Drive, Bradenton, FL 34203 (MLS # A4655998)
$579,000
Lot Size
10,019 sqft

Home Size
2,794 sqft

Beds
4 Beds

Baths
2 Baths

4124 Herrick Lane
Sarasota, FL
Photo of 4124 Herrick Lane, Sarasota, FL 34241 (MLS # TB8395122)
$400,000
Lot Size
10,455 sqft

Home Size
1,630 sqft

Beds
3 Beds

Baths
2 Baths

3915 Meadow Creek Drive
Sarasota, FL
Photo of 3915 Meadow Creek Drive, Sarasota, FL 34233 (MLS # A4655993)
$580,000
Lot Size
17,860 sqft

Home Size
1,870 sqft

Beds
3 Beds

Baths
2 Baths

4001 Beneva Road #319
Sarasota, FL
Photo of 4001 Beneva Road #319, Sarasota, FL 34233 (MLS # A4655995)
$215,000
Lot Size
8.10 ac

Home Size
1,419 sqft

Beds
3 Beds

Baths
3 Baths

160 Coolidge Drive
Sarasota, FL
Photo of 160 Coolidge Drive, Sarasota, FL 34236 (MLS # A4655744)
$1,490,000
Lot Size
6,099 sqft

Home Size
2,050 sqft

Beds
4 Beds

Baths
2 Baths

5523 Secluded Oaks Way
Sarasota, FL
Photo of 5523 Secluded Oaks Way, Sarasota, FL 34233 (MLS # A4655542)
$769,000
Lot Size
10,890 sqft

Home Size
2,827 sqft

Beds
4 Beds

Baths
3 Baths

5005 Torrey Pines Run
Bradenton, FL
Photo of 5005 Torrey Pines Run, Bradenton, FL 34211 (MLS # A4655972)
$450,000
Lot Size
8,277 sqft

Home Size
1,571 sqft

Beds
3 Beds

Baths
2 Baths

6516 Palm Leaf Court
Sarasota, FL
Photo of 6516 Palm Leaf Court, Sarasota, FL 34243 (MLS # A4655967)
$575,000
Lot Size
8,277 sqft

Home Size
2,150 sqft

Beds
3 Beds

Baths
2 Baths

19927 Bridgetown Loop
Venice, FL
Photo of 19927 Bridgetown Loop, Venice, FL 34293 (MLS # N6139290)
$649,900
Lot Size
6,534 sqft

Home Size
2,198 sqft

Beds
3 Beds

Baths
3 Baths

3404 56th Dr E
Bradenton, FL
Photo of 3404 56th Dr E, Bradenton, FL 34203 (MLS # A4655973)
$399,900
Lot Size
11,326 sqft

Home Size
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Beds
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481 Saturn Avenue
Sarasota, FL
Photo of 481 Saturn Avenue, Sarasota, FL 34243 (MLS # A4655968)
$425,900
Lot Size
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Home Size
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3810 75th Street W #128
Bradenton, FL
Photo of 3810 75th Street W #128, Bradenton, FL 34209 (MLS # A4655966)
$289,900
Lot Size
1.44 ac

Home Size
1,450 sqft

Beds
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152 Coolidge Drive
Sarasota, FL
Photo of 152 Coolidge Drive, Sarasota, FL 34236 (MLS # A4655758)
$1,700,000
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Home Size
1,428 sqft

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3 Beds

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  • 3305 Notre Dame Place #3305
    Bradenton, FL
    Photo of 3305 Notre Dame Place #3305, Bradenton, FL 34207 (MLS # A4655891)
    $329,945
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    3,921 sqft

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    1,230 sqft

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    2 Beds

    Baths
    2 Baths

  • 4802 51st Street W #1313
    Bradenton, FL
    Photo of 4802 51st Street W #1313, Bradenton, FL 34210 (MLS # A4656007)
    $170,000
    Lot Size
    39.01 ac

    Home Size
    750 sqft

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    Baths
    1 Bath

  • 1559 Running Tide Place
    Sarasota, FL
    Photo of 1559 Running Tide Place, Sarasota, FL 34240 (MLS # TB8397341)
    $1,169,990
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  • 7750 Ridgelake Circle
    Bradenton, FL
    Photo of 7750 Ridgelake Circle, Bradenton, FL 34203 (MLS # A4656001)
    $468,000
    Lot Size
    7,406 sqft

    Home Size
    1,622 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 19023 Mangieri Street
    Venice, FL
    Photo of 19023 Mangieri Street, Venice, FL 34293 (MLS # A4655980)
    $425,000
    Lot Size
    6,099 sqft

    Home Size
    1,437 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 1224 38th Street W
    Bradenton, FL
    Photo of 1224 38th Street W, Bradenton, FL 34205 (MLS # A4656002)
    $275,000
    Lot Size
    10,019 sqft

    Home Size
    936 sqft

    Beds
    2 Beds

    Baths
    1 Bath

  • 4745 Trout River Crossing
    Ellenton, FL
    Photo of 4745 Trout River Crossing, Ellenton, FL 34222 (MLS # TB8397326)
    $474,000
    Lot Size
    9,148 sqft

    Home Size
    2,035 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 4531 Useppa Drive
    Bradenton, FL
    Photo of 4531 Useppa Drive, Bradenton, FL 34203 (MLS # A4655998)
    $579,000
    Lot Size
    10,019 sqft

    Home Size
    2,794 sqft

    Beds
    4 Beds

    Baths
    2 Baths

  • 4124 Herrick Lane
    Sarasota, FL
    Photo of 4124 Herrick Lane, Sarasota, FL 34241 (MLS # TB8395122)
    $400,000
    Lot Size
    10,455 sqft

    Home Size
    1,630 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 3915 Meadow Creek Drive
    Sarasota, FL
    Photo of 3915 Meadow Creek Drive, Sarasota, FL 34233 (MLS # A4655993)
    $580,000
    Lot Size
    17,860 sqft

    Home Size
    1,870 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 4001 Beneva Road #319
    Sarasota, FL
    Photo of 4001 Beneva Road #319, Sarasota, FL 34233 (MLS # A4655995)
    $215,000
    Lot Size
    8.10 ac

    Home Size
    1,419 sqft

    Beds
    3 Beds

    Baths
    3 Baths

  • 160 Coolidge Drive
    Sarasota, FL
    Photo of 160 Coolidge Drive, Sarasota, FL 34236 (MLS # A4655744)
    $1,490,000
    Lot Size
    6,099 sqft

    Home Size
    2,050 sqft

    Beds
    4 Beds

    Baths
    2 Baths

  • 5523 Secluded Oaks Way
    Sarasota, FL
    Photo of 5523 Secluded Oaks Way, Sarasota, FL 34233 (MLS # A4655542)
    $769,000
    Lot Size
    10,890 sqft

    Home Size
    2,827 sqft

    Beds
    4 Beds

    Baths
    3 Baths

  • 5005 Torrey Pines Run
    Bradenton, FL
    Photo of 5005 Torrey Pines Run, Bradenton, FL 34211 (MLS # A4655972)
    $450,000
    Lot Size
    8,277 sqft

    Home Size
    1,571 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 6516 Palm Leaf Court
    Sarasota, FL
    Photo of 6516 Palm Leaf Court, Sarasota, FL 34243 (MLS # A4655967)
    $575,000
    Lot Size
    8,277 sqft

    Home Size
    2,150 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 19927 Bridgetown Loop
    Venice, FL
    Photo of 19927 Bridgetown Loop, Venice, FL 34293 (MLS # N6139290)
    $649,900
    Lot Size
    6,534 sqft

    Home Size
    2,198 sqft

    Beds
    3 Beds

    Baths
    3 Baths

  • 3404 56th Dr E
    Bradenton, FL
    Photo of 3404 56th Dr E, Bradenton, FL 34203 (MLS # A4655973)
    $399,900
    Lot Size
    11,326 sqft

    Home Size
    1,310 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 481 Saturn Avenue
    Sarasota, FL
    Photo of 481 Saturn Avenue, Sarasota, FL 34243 (MLS # A4655968)
    $425,900
    Lot Size
    13,068 sqft

    Home Size
    1,428 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 3810 75th Street W #128
    Bradenton, FL
    Photo of 3810 75th Street W #128, Bradenton, FL 34209 (MLS # A4655966)
    $289,900
    Lot Size
    1.44 ac

    Home Size
    1,450 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 152 Coolidge Drive
    Sarasota, FL
    Photo of 152 Coolidge Drive, Sarasota, FL 34236 (MLS # A4655758)
    $1,700,000
    Lot Size
    6,099 sqft

    Home Size
    1,428 sqft

    Beds
    3 Beds

    Baths
    2 Baths

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