Longboat Key, FL Homes

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  /50

  $599,999

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft

  3320 Gulf of Mexico Dr Unit 207-C, Longboat Key, FL 34228

  Modern Waterfront Living in the Heart of Longboat Key-Experience the best of coastal living in this beautifully renovated 2-bedroom, 2-bathroom condo, perfectly situated on the water in one of Longboat Key’s most desirable communities. This light-filled residence features a newly reimagined open-concept kitchen with gleaming quartz countertops, bright modern cabinetry, premium stainless steel

  

  Tami Cashi

  COLDWELL BANKER REALTY

  (941) 206-4076

  3320 Gulf of Mexico Dr Unit 207-C, Longboat Key, FL 34228
• Explore Longboat Key

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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
• 

  $1,425,000 Sold Nov 26, 2025

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 11 Days On Market

  Current Estimated Value $1,423,654

  Last Listing Agent Irma Scherer COMPASS FLORIDA LLC

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228
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  /2

  Est $555,295 Not Listed For Sale

  575 Sutton Place Unit T-4, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,450 Sq Ft
  • Built 1972

  575 Sutton Place Unit T-4, Longboat Key, FL 34228

  Last Sold Summary

  • 4% Below List Price
  • $399/SF
  • 23 Days On Market

  Last Sold Price $579,000

  Last Listing Agent Michael Yawitz Michael Saunders
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  /42

  $1,299,000

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  603 Longboat Club Rd Unit 402N, Longboat Key, FL 34228

  Nestled behind the exclusive gates of the Longboat Key Club, Longboat Key Towers stands as one of the island’s most distinguished Gulf-front communities. Within the north tower, this elegant fourth-floor residence captures breathtaking views from sunrise to sunset — with two expansive balconies overlooking the shimmering Gulf of Mexico to the west and the rolling greens and bay waters to the

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  (941) 401-4630

  603 Longboat Club Rd Unit 402N, Longboat Key, FL 34228
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  /56

  $6,000 per month

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

  706 Bayport Way Unit 706, Longboat Key, FL 34228

  This beautiful 2 bedroom/2 bath split and open floor plan condo is spacious and bright. The kitchen featuring a built-in desk and granite counters has been opened to the dining/living room area with views of the pond, fountain and lush tropical landscaping. A stackable washer/dryer in closet for your convenience. Lanai enclosed with tropical views. Bayport Beach and Tennis Club is bordered by the

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 274-3620

  706 Bayport Way Unit 706, Longboat Key, FL 34228
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  /2

  $585,000 Sold Jan 16, 2026

  4320 Falmouth Dr Unit 301, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1969

  Last Sold Summary

  • 10% Below List Price
  • $445/SF
  • 33 Days On Market

  Current Estimated Value $586,064

  Last Listing Agent Kevin Tai PREFERRED SHORE LLC

  4320 Falmouth Dr Unit 301, Longboat Key, FL 34228
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  /2

  Est $776,154 Not Listed For Sale

  7165 Longboat Dr N, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1964

  7165 Longboat Dr N, Longboat Key, FL 34228

  Last Sold Summary

  • 3% Below List Price
  • $592/SF
  • 466 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Monica Newcomer COLDWELL BANKER REALTY
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  /71

  $649,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228

  Luxury Coastal Living at Longboat Harbour: Experience stunning canal views and modern elegance in this impeccably renovated 3rd-floor condo, ideally situated in the desirable all-age community of Longboat Harbour. Offered turnkey furnished, this beautifully curated residence is ready for your immediate enjoyment, whether you're seeking a winter retreat or full-time coastal living. Step inside to

  

  Marsha Winegarden

  WAGNER REALTY

  (941) 239-6809

  4350 Chatham Dr Unit 307, 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

  $655,000 Sold Dec 10, 2025

  560 Cedar St, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft
  • Built 1970

  Last Sold Summary

  • 12% Below List Price
  • $359/SF
  • 64 Days On Market

  Current Estimated Value $902,138

  Last Listing Agent Lauren Hofing THE KEYES COMPANY - SARASOTA

  560 Cedar St, Longboat Key, FL 34228
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  /2

  Est $857,676 Not Listed For Sale

  5655 Gulf of Mexico Dr Unit D205, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1975

  5655 Gulf of Mexico Dr Unit D205, Longboat Key, FL 34228

  Last Sold Summary

  • 2% Below List Price
  • $687/SF
  • 81 Days On Market

  Last Sold Price $875,000

  Last Listing Agent John Milkovich CHARLES RUTENBERG REALTY INC
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  /95

  $450,000

  • 1 Bed
  • 2 Baths
  • 1,244 Sq Ft

  619 Cedars Ct, Longboat Key, FL 34228

  Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover

  

  Simone Schaerf

  MICHAEL SAUNDERS & COMPANY

  (941) 219-0078

  619 Cedars Ct, 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

  $350,000 Sold Jul 03, 2025

  3802 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1970

  Last Sold Summary

  • 18% Below List Price
  • $251/SF
  • 70 Days On Market

  Current Estimated Value $385,056

  Last Listing Agent Kathleen Magnus FLORIDA GALLERY REAL ESTATE

  3802 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  Est $521,559 Not Listed For Sale

  4440 Exeter Dr Unit 304, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1970

  4440 Exeter Dr Unit 304, Longboat Key, FL 34228

  Last Sold Summary

  • 3% Above List Price
  • $509/SF
  • 38 Days On Market

  Last Sold Price $505,000

  Last Listing Agent Malihe Karimi Michael Saunders
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  /82

  $10,900,000

  • 8 Beds
  • 8 Baths
  • 5,886 Sq Ft

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228

  Rare opportunity, two fully furnished TWIN residences (TWO UNITS BEING SOLD AS ONE 4473+4477 Gulf of Mexico Drive ). Directly on the pristine shores of Longboat Key! Combined 8 bedrooms, 8 Bathrooms. Spanning nearly 6,000 sq. ft., on .58 GULF-FRONT acres, this two-story property offers mirror-image residences, each thoughtfully decorated with both modern and timeless designs. A true investment

  

  Curtis Andrews

  BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  (941) 841-8278

  4473 Gulf of Mexico Dr, 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

  $1,098,000 Sold Jul 30, 2025

  240 Sands Point Rd Unit 4201, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1982

  Last Sold Summary

  • 8% Below List Price
  • $1,464/SF
  • 162 Days On Market

  Current Estimated Value $1,092,535

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  240 Sands Point Rd Unit 4201, Longboat Key, FL 34228
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  /2

  Est $4,727,331 Not Listed For Sale

  596 Yawl Ln, Longboat Key, FL 34228

  • 5 Beds
  • 5.5 Baths
  • 7,374 Sq Ft
  • Built 1996

  596 Yawl Ln, Longboat Key, FL 34228

  Last Sold Summary

  • 4% Above List Price
  • $619/SF
  • 69 Days On Market

  Last Sold Price $4,563,500

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /33

  $590,000

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

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

  ****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 island breezes in all year long. Located

  

  Meredith Van Vaals

  COLDWELL BANKER REALTY

  (941) 220-0872

  2301 Gulf of Mexico Dr Unit 54, 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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  $549,000 Sold Feb 05, 2026

  2045 Gulf of Mexico Dr Unit M1410, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Built 1974

  Last Sold Summary

  • $592/SF
  • 0 Days On Market

  Current Estimated Value $548,968

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  2045 Gulf of Mexico Dr Unit M1410, Longboat Key, FL 34228
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  /2

  Est $1,424,867 Not Listed For Sale

  4241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft
  • Built 1980

  4241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • $934/SF
  • 51 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /32

  $1,590,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  601 Longboat Club Rd Unit 504S, Longboat Key, FL 34228

  Welcome to Unit 504S at Longboat Key Towers, a rare corner beachfront condo for sale on the highly sought-after south end of Longboat Key, ideally located behind the gates of Longboat Key Club and just minutes from St. Armands Circle and downtown Sarasota. Perfectly positioned above the sand and sea, this spacious 2-bedroom 2.5 bath residence captures uninterrupted sweeping views of the Gulf of

  

  Irma Scherer

  COMPASS FLORIDA LLC

  (941) 401-0752

  601 Longboat Club Rd Unit 504S, Longboat Key, FL 34228
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  /58

  $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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  /2

  $880,000 Sold Apr 07, 2025

  1930 Harbourside Dr Unit 113, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1982

  Last Sold Summary

  • $462/SF

  Current Estimated Value $866,852

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

  1930 Harbourside Dr Unit 113, Longboat Key, FL 34228
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  /2

  Est $2,004,222 Not Listed For Sale

  3030 Grand Bay Blvd Unit 396, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,925 Sq Ft
  • Built 1998

  3030 Grand Bay Blvd Unit 396, Longboat Key, FL 34228

  Last Sold Summary

  • $684/SF
  • 3 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Mark Midyett KELLER WILLIAMS ON THE WATER S
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  /89

  $2,000,000

  • 3 Beds
  • 3.5 Baths
  • 3,690 Sq Ft

  2410 Harbourside Dr Unit 111, Longboat Key, FL 34228

  Longboat Key luxury living with sweeping water views. Introducing bayside luxury at Marina Bay within Bay Isles. Now available for the first time to purchase, this unique single level condominium residence boasts a private elevator lobby. This unique residence fitted with impact glass and newer roofing is secured for the quality of your peace of mind. The condo association offers resident

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  (941) 206-2461

  2410 Harbourside Dr Unit 111, 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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  $975,000 Sold Jul 28, 2025

  663 Penfield St, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,446 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $674/SF
  • 7 Days On Market

  Current Estimated Value $1,004,509

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  663 Penfield St, Longboat Key, FL 34228
• 

  /2

  Est $601,949 Not Listed For Sale

  620 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1968

  620 Fox St, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Above List Price
  • $339/SF
  • 49 Days On Market

  Last Sold Price $567,000

  Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES
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  /57

  $995,000

  • 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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  /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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  /2

  $1,250,000 Sold Apr 15, 2025

  541 Edlee Ln, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1976

  Last Sold Summary

  • 10% Below List Price
  • $469/SF
  • 50 Days On Market

  Current Estimated Value $1,261,965

  Last Listing Agent Lisa Garcia COLDWELL BANKER REALTY

  541 Edlee Ln, Longboat Key, FL 34228
• 

  /2

  Est $739,523 Not Listed For Sale

  4700 Gulf of Mexico Dr Unit PH6, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1975

  4700 Gulf of Mexico Dr Unit PH6, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Below List Price
  • $515/SF
  • 294 Days On Market

  Last Sold Price $784,950

  Last Listing Agent Debby McCaig COLDWELL BANKER REALTY
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  /56

  $889,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft

  1211 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  Under contract-accepting backup offers. NEW PRICE- Great Value! Welcome to your dream beachfront retreat at The Promenade. This sunny, south-facing seventh-floor residence offers an open, spacious interior encompassing 1585 sq. ft. of living space. It’s waiting for you to make it your own and embrace the captivating views of the Gulf, Sarasota Bay, and downtown Sarasota from its wraparound

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  (941) 271-0250

  1211 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /81

  $13,000 per month

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

  806 Bayport Way Unit 806, Longboat Key, FL 34228

  Discover a tranquil retreat at 806 Bayport Way, where coastal living meets sophisticated design. This exceptional property is ideally located near a private beach, providing residents with exclusive access to sun-soaked shores and beautiful ocean views.Upon entering, you’ll be greeted by a thoughtfully designed space that emphasizes both comfort and functionality. The kitchen features

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 390-2885

  806 Bayport Way Unit 806, Longboat Key, FL 34228
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  /2

  $4,000,000 Sold Mar 25, 2025

  3480 Bayou Sound, Longboat Key, FL 34228

  • 5 Beds
  • 4.5 Baths
  • 3,926 Sq Ft
  • Built 2024

  Last Sold Summary

  • 23% Below List Price
  • $1,019/SF
  • 57 Days On Market

  Current Estimated Value $3,588,645

  Last Listing Agent Nicholle McKiernan COLDWELL BANKER REALTY

  3480 Bayou Sound, Longboat Key, FL 34228
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  /2

  Est $651,660 Not Listed For Sale

  4440 Exeter Dr Unit 301, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Built 1970

  4440 Exeter Dr Unit 301, Longboat Key, FL 34228

  Last Sold Summary

  • 1% Below List Price
  • $563/SF
  • 94 Days On Market

  Last Sold Price $657,500

  Last Listing Agent Sandra Endres COLDWELL BANKER REALTY

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