Longboat Key, FL Homes

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  /30

  $974,500

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft

  1000 Longboat Club Rd Unit 403, Longboat Key, FL 34228

  Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  (941) 239-4757

  1000 Longboat Club Rd Unit 403, Longboat Key, FL 34228
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  /75

  $13,500 per month

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Condo for Rent

  716 Bayport Way Unit 716, Longboat Key, FL 34228

  GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open concept floor plan. This home welcomes you into an expansive Living/Dining/Kitchen and offers plenty of natural light. In addition, it boasts a generous size master bedroom with en suite bathroom and an alcove that accommodates a desk and seating area. Bayport Beach & Tennis Club

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 206-0566

  716 Bayport Way Unit 716, Longboat Key, FL 34228
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  $1,600,000 Sold Mar 16, 2026

  3060 Grand Bay Blvd Unit 154, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $627/SF
  • 70 Days On Market

  Current Estimated Value $1,702,399

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3060 Grand Bay Blvd Unit 154, Longboat Key, FL 34228
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  /2

  Est $755,517 Not Listed For Sale

  1930 Harbourside Dr Unit 117, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1982

  1930 Harbourside Dr Unit 117, Longboat Key, FL 34228

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 4 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Cindy Schatzle COLDWELL BANKER REALTY
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  /33

  $590,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2301 Gulf of Mexico Dr Unit 54, Longboat Key, FL 34228

  Under contract-accepting backup offers. ****MOTIVATED SELLER. GET A CONDO ON THE BEACH BELOW MARKET IN AN UPGRADED BUILDING. Enormous and beautiful outside balcony for warm breeze enjoyment. Building is directly beachfront. ****Creatively coined “Studio 54,” located at The Islander Club on Longboat Key Beach, this 2-bedroom, 2-bathroom condominium has an enormous lanai that brings the beautiful

  

  Meredith Van Vaals

  COLDWELL BANKER REALTY

  (941) 220-0872

  2301 Gulf of Mexico Dr Unit 54, Longboat Key, FL 34228
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  /56

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  522 Bayport Way Unit 522, Longboat Key, FL 34228

  GORGEOUS LONG TERM RENTAL!! Bayport Beach & Tennis CLub is an amenity-rich community at sea's edge and is situated in the middle ofLongboat Key. This 2 bedroom, 2 bathroom fully furnished rental is beautifully appointed. This residence offers a wonderful retreat as a annual. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-0065

  522 Bayport Way Unit 522, Longboat Key, FL 34228
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  /2

  $940,000 Sold Jun 23, 2025

  1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,827 Sq Ft
  • Built 1985

  Last Sold Summary

  • 27% Below List Price
  • $515/SF
  • 73 Days On Market

  Current Estimated Value $973,319

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  /20

  Est $1,001,846 Not Listed For Sale

  1105 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1981

  1105 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  Last Sold Summary

  • $665/SF
  • 13 Days On Market

  Last Sold Price $1,000,000

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  /57

  $995,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft

  1050 Longboat Club Rd Unit 301, Longboat Key, FL 34228

  Huge price reduction now under $1mm for direct 180 degree gulf front!Imagine waking up every morning to the sound of gentle waves and stepping onto your balcony to enjoy uninterrupted, straight-on Gulf views—this rarely available 01-stack residence delivers beachfront living exactly the way it should be. Perfectly positioned behind the private gates of the Longboat Key Club and nestled

  

  Greg Martin

  STERLING REALTY

  (941) 369-9007

  1050 Longboat Club Rd Unit 301, Longboat Key, FL 34228
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  /68

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  720 Bayport Way Unit 720, Longboat Key, FL 34228

  Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical setting with a spacious eat-in kitchen that is open to the living area. Elegantly furnished in a natural color pallet. The master suite is tastefully decorated, with a built in vanity, double sinks and his and her closets. It also features a small alcove with a desk with access

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 206-3379

  720 Bayport Way Unit 720, Longboat Key, FL 34228
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  /2

  $949,000 Sold Apr 23, 2025

  1050 Longboat Club Rd Unit 305, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Built 1974

  Last Sold Summary

  • $736/SF
  • 2 Days On Market

  Current Estimated Value $954,947

  Last Listing Agent Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

  1050 Longboat Club Rd Unit 305, Longboat Key, FL 34228
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  /2

  Est $2,094,126 Not Listed For Sale

  1241 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft
  • Built 1996

  1241 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Above List Price
  • $657/SF
  • 95 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC
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  /93

  $4,750,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 4,209 Sq Ft

  1571 Harbor Cay Ln, Longboat Key, FL 34228

  Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key.Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area

  

  Julie Klick

  MICHAEL SAUNDERS & COMPANY

  (941) 207-2668

  1571 Harbor Cay Ln, Longboat Key, FL 34228
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  /60

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  744 Bayport Way Unit 744, Longboat Key, FL 34228

  Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fully furnished and equipped with flat screen TV's, cable and WiFi. This residence features a spacious screened lanai with garden views in addition to an outdoor sun deck with loungers for basking in the sun. Bayport sits on 27 lushly landscaped acres and has 1200

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 294-6846

  744 Bayport Way Unit 744, Longboat Key, FL 34228
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  /2

  $1,940,000 Sold Dec 19, 2025

  565 Sanctuary Dr Unit A203, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,375 Sq Ft
  • Built 1989

  Last Sold Summary

  • 27% Below List Price
  • $817/SF
  • 321 Days On Market

  Current Estimated Value $1,923,365

  Last Listing Agent Kathy Callahan MICHAEL SAUNDERS & COMPANY

  565 Sanctuary Dr Unit A203, Longboat Key, FL 34228
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  /2

  Est $1,793,903 Not Listed For Sale

  575 Sanctuary Dr Unit A201, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,823 Sq Ft
  • Built 1990

  575 Sanctuary Dr Unit A201, Longboat Key, FL 34228

  Last Sold Summary

  • $987/SF
  • 29 Days On Market

  Last Sold Price $1,800,000

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /50

  $530,000

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  597 Sutton Place, Longboat Key, FL 34228

  Experience the best of Longboat Key living at Sutton Place, ideally positioned mid-island with convenient access to both Sarasota Bay and the Gulf of Mexico. Enjoy deeded beach access just moments away—perfect for daily beach outings, sunset walks, and the pristine Gulf shoreline.Active living comes naturally here. Bike to Bayfront Park for pickleball or tennis, or visit the nearby dog parks

  

  Simone Schaerf

  MICHAEL SAUNDERS & COMPANY

  (941) 336-7456

  597 Sutton Place, Longboat Key, FL 34228
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  /54

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  517 Bayport Way Unit 517, Longboat Key, FL 34228

  Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness center

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 325-0092

  517 Bayport Way Unit 517, Longboat Key, FL 34228
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  /2

  $1,550,000 Sold Nov 07, 2025

  2525 Gulf of Mexico Dr Unit 3F, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 1972

  Last Sold Summary

  • 9% Below List Price
  • $1,062/SF
  • 163 Days On Market

  Current Estimated Value $1,519,169

  Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2525 Gulf of Mexico Dr Unit 3F, Longboat Key, FL 34228
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  /52

  Est $786,313 Not Listed For Sale

  1065 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1981

  1065 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  Last Sold Summary

  • 3% Above List Price
  • $507/SF
  • 88 Days On Market

  Last Sold Price $762,500

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  /54

  $925,000

  • 4 Beds
  • 3 Baths
  • 2,242 Sq Ft

  651 Jungle Queen Way, Longboat Key, FL 34228

  PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous 1⁄4-acre lot. Canal offers direct access to Sarasota Bay

  

  Lori Campbell

  ALLEGIANT REAL ESTATE GROUP

  (941) 770-4539

  651 Jungle Queen Way, Longboat Key, FL 34228
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  /74

  $15,000 per month

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Condo for Rent

  603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228

  LONGBOAT KEY CLUB – GULF FRONT LUXURY RENTAL Enter the private, gated community of Longboat Key Club and experience true coastal paradise with breathtaking Gulf-front views. This completely remodeled 2-bedroom, 2-bath condominium showcases elegant, high-end finishes throughout. The bright and open living area features stunning marble flooring and walls, with expansive windows and a large private

  

  Lily Behrends

  RE/MAX ALLIANCE GROUP

  (941) 299-8853

  603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228
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  $1,300,000 Sold Mar 25, 2026

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $838/SF
  • 214 Days On Market

  Current Estimated Value $1,512,183

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  Est $442,684 Not Listed For Sale

  5310 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 711 Sq Ft
  • Built 1973

  5310 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

  Last Sold Summary

  • 2% Below List Price
  • $633/SF
  • 2 Days On Market

  Last Sold Price $450,000

  Last Listing Agent John Heidemann COLDWELL BANKER SARASOTA CENT.
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  /37

  $799,000

  • Land
  • 0.15 Acre
  • $5,326,667 per Acre

  766 Saint Judes Dr N, Longboat Key, FL 34228

  The Ultimate Boater's Foundation! Rare Canal-Front Lot with Twin Lifts & New Seawall! This prime, cleared canal-front lot offers the most turn-key building opportunity on Longboat Key. While other buyers are stuck in the permitting phase for marine infrastructure, this one already has it complete and you can dock your fleet on day one. Unmatched Infrastructure Value:• Brand New Seawall: 100

  

  Nikki Spirakis

  BRG REAL ESTATE INC

  (941) 688-9189

  766 Saint Judes Dr N, Longboat Key, FL 34228
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  /65

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Condo for Rent

  601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228

  Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2026. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course

  

  Irma Scherer

  COMPASS FLORIDA LLC

  (941) 401-1756

  601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
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  $631,000 Sold Aug 28, 2025

  826 Bayport Way Unit 826, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 1981

  Last Sold Summary

  • 30% Below List Price
  • $376/SF
  • 347 Days On Market

  Current Estimated Value $652,974

  Last Listing Agent Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  826 Bayport Way Unit 826, Longboat Key, FL 34228
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  Est $2,085,371 Not Listed For Sale

  3161 Bayou Sound, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 3,684 Sq Ft
  • Built 1990

  3161 Bayou Sound, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Below List Price
  • $597/SF
  • 67 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Linda Weber COLDWELL BANKER REALTY
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  /49

  $2,000,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 3,383 Sq Ft

  2450 Harbourside Dr Unit 234, Longboat Key, FL 34228

  Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized

  

  Beverly St Hilaire

  MICHAEL SAUNDERS & COMPANY

  (941) 960-7660

  2450 Harbourside Dr Unit 234, Longboat Key, FL 34228
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  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228

  Introducing a remarkable opportunity to rent a piece of paradise at 829 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. As you enter the community, you are greeted by meticulously landscaped grounds that set the

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 239-2327

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228
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  $585,000 Sold Jun 20, 2025

  653 Cedars Ct Unit 25, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 1988

  Last Sold Summary

  • 16% Below List Price
  • $406/SF
  • 110 Days On Market

  Current Estimated Value $569,437

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  653 Cedars Ct Unit 25, Longboat Key, FL 34228
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  /15

  Est $396,571 Not Listed For Sale

  2600 Harbourside Dr Unit L-10, Longboat Key, FL 34228

  • Studio
  • Built 1985

  2600 Harbourside Dr Unit L-10, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • 66 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /59

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 2,385 Sq Ft

  415 L Ambiance Dr Unit B202, Longboat Key, FL 34228

  Gulf-front enclave offers a rare blend of luxury, location, and lifestyle that transforms every day into a retreat. From the moment you step inside, you’re greeted by an atmosphere of refined elegance and architectural clarity—crafted for those who appreciate design as a way of life. This residence exudes sophistication with interiors envisioned by an internationally acclaimed designer,

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  (941) 300-0171

  415 L Ambiance Dr Unit B202, Longboat Key, FL 34228
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  /40

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,514 Sq Ft
  • Condo for Rent

  615 Dream Island Place Unit 201, Longboat Key, FL 34228

  available January 15 through February and March 2027. And January-March 2027 due to cancellation. BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  (941) 279-2178

  615 Dream Island Place Unit 201, Longboat Key, FL 34228
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  $385,000 Sold Nov 20, 2025

  556 Spanish Dr N Unit 154, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1969

  Last Sold Summary

  • $276/SF

  Current Estimated Value $384,706

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  556 Spanish Dr N Unit 154, Longboat Key, FL 34228
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  /28

  Est $664,005 Not Listed For Sale

  561 Gulf Bay Rd, Longboat Key, FL 34228

  561 Gulf Bay Rd, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • 52 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /80

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft

  1932 Harbourside Dr Unit 254, Longboat Key, FL 34228

  Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Inside, the kitchen showcases granite

  

  Beverly St Hilaire

  MICHAEL SAUNDERS & COMPANY

  (941) 390-0836

  1932 Harbourside Dr Unit 254, Longboat Key, FL 34228
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  /30

  $7,750 per month

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  (941) 207-4034

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
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  $1,000,000 Sold Aug 18, 2025

  1211 Gulf of Mexico Dr Unit 701, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1985

  Last Sold Summary

  • 37% Below List Price
  • $476/SF
  • 155 Days On Market

  Current Estimated Value $1,082,386

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  1211 Gulf of Mexico Dr Unit 701, Longboat Key, FL 34228
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  Est $3,624,881 Not Listed For Sale

  6941 Bayside Dr, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 2023

  6941 Bayside Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 19% Below List Price
  • $1,375/SF
  • 123 Days On Market

  Last Sold Price $4,500,000

  Last Listing Agent Kate Enis FINE PROPERTIES

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