Longboat Key, FL Homes

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  $375,000

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228

  Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
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  $5,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

  Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais,

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
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  $1,100,000 Sold Feb 17, 2026

  2110 Harbourside Dr Unit 558, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 2,550 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $431/SF
  • 11 Days On Market

  Current Estimated Value $1,124,576

  Last Listing Agent Scott Rickards RE/MAX ALLIANCE GROUP

  2110 Harbourside Dr Unit 558, Longboat Key, FL 34228
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  Est $274,798 Not Listed For Sale

  699 El Centro Unit 182, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft
  • Built 1969

  699 El Centro Unit 182, Longboat Key, FL 34228

  Last Sold Summary

  • 31% Above List Price
  • $158/SF
  • 24 Days On Market

  • Last Sold Price $210,000
  • Apr 07, 2025

  Last Listing Agent Geoff Scalera AUM FLORIDA REAL ESTATE LLC
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  /65

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228

  Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit!Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms,

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228
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  $40,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228

  An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
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  $2,000,000 Sold Apr 10, 2026

  100 Sands Point Rd Unit 114, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $955/SF
  • 28 Days On Market

  Current Estimated Value $1,764,981

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  100 Sands Point Rd Unit 114, Longboat Key, FL 34228
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  /66

  Est $487,667 Not Listed For Sale

  583 Spanish Dr S Unit 129, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • Built 1968

  583 Spanish Dr S Unit 129, Longboat Key, FL 34228

  Last Sold Summary

  • 23% Below List Price
  • $452/SF
  • 223 Days On Market

  • Last Sold Price $633,000
  • Aug 16, 2023

  Last Listing Agent Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $595,000

  • Land
  • 6,098 Sq Ft
  • $4,250,000 per Acre

  641 Broadway St, Longboat Key, FL 34228

  Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available on Longboat Key, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities,

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  641 Broadway St, Longboat Key, FL 34228
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • House for Rent

  957 Spanish Dr N, Longboat Key, FL 34228

  AVAILABLE STARTING MAY 1, 2026. WITH 4 MONTH MINUMUM RENTAL DURING SEASON and 3 MONTHS OFF SEASON. FULL WATERFRONT NEWLY RENOVATED and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main

  Norma Mladineo COLDWELL BANKER REALTY

  957 Spanish Dr N, Longboat Key, FL 34228
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  $1,200,000 Sold May 01, 2026

  3030 Grand Bay Blvd Unit 323, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft
  • Built 1998

  Last Sold Summary

  • 19% Below List Price
  • $471/SF
  • 57 Days On Market

  Current Estimated Value $1,558,850

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  3030 Grand Bay Blvd Unit 323, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G26, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1980

  3710 Gulf of Mexico Dr Unit G26, Longboat Key, FL 34228

  Last Sold Summary

  • $274/SF

  • Last Sold Price $250,000
  • Feb 10, 2025

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $490,000

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft

  6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Tucked within the intimate Whitney Beach community on Longboat Key's serene north end, this beautifully reimagined two-bedroom, two-bath end unit occupies one of the community's most coveted positions — a corner residence offering protected water views over Bishop's Bayou from both the kitchen and living room, sheltered from the wake and noise of

  Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
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  $7,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  $900,000 Sold Apr 27, 2026

  6841 Longboat Dr S, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1935

  Last Sold Summary

  • 24% Below List Price
  • $652/SF
  • 112 Days On Market

  Current Estimated Value $1,100,081

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  6841 Longboat Dr S, Longboat Key, FL 34228
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  Est $1,343,213 Not Listed For Sale

  603 Longboat Club Rd Unit 903N, Longboat Key, FL 34228

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

  603 Longboat Club Rd Unit 903N, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Above List Price
  • $861/SF
  • 26 Days On Market

  • Last Sold Price $1,255,000
  • Mar 07, 2025

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  $2,400,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228

  Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2025, fee for

  Michael Moulton MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228
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  $3,200 Per Month

  • 1 Bed
  • 1 Bath
  • 667 Sq Ft
  • Condo for Rent

  747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228

  GORGEOUS BAY VIEWS. Located in a quiet association of only eight units. Annual Unfurnished unit; open kitchen/living and dining area with master bedroom and tub/shower combo in en-suite bath. Canal views with private dock and boat lift (a boater and fisherman's dream). Drop a line outside your back door! Screened lanai with washer/dryer. Exterior parking immediately outside the unit with gas BBQ

  Gregory Koss WAGNER REALTY

  747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
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  $1,400,000 Sold Feb 18, 2026

  513 Bayport Way Unit 513, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 2,186 Sq Ft
  • Built 1980

  Last Sold Summary

  • $640/SF
  • 8 Days On Market

  Current Estimated Value $1,391,265

  Last Listing Agent Alexis Smith-Frady COMPASS FLORIDA LLC

  513 Bayport Way Unit 513, Longboat Key, FL 34228
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  Est $538,915 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

  • 7% Below List Price
  • $399/SF
  • 23 Days On Market

  • Last Sold Price $579,000
  • Feb 28, 2025

  Last Listing Agent Michael Yawitz Michael Saunders
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  /54

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  842 Bayport Way Unit 842, Longboat Key, FL 34228

  Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in

  Rosemarie McKee COLDWELL BANKER REALTY

  842 Bayport Way Unit 842, Longboat Key, FL 34228
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  $10,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • Condo for Rent

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228

  Stunning Gulf-Front Condo with Breathtaking Views at Islands West! Experience the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom condominium on the 12th floor of Islands West, where full Gulf views become a part of your daily life. This beautifully furnished unit is not just a rental; it’s a lifestyle choice that offers you the chance to wake up to the soothing sounds of waves

  Jane Hunter JENNETTE PROPERTIES INC

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
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  $2,700,000 Sold Jul 14, 2025

  549 Sloop Ln, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 4,127 Sq Ft
  • Built 2000

  Last Sold Summary

  • 37% Below List Price
  • $654/SF
  • 255 Days On Market

  Current Estimated Value $2,670,851

  Last Listing Agent Tracey Stetler COLDWELL BANKER REALTY

  549 Sloop Ln, Longboat Key, FL 34228
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  Not Listed For Sale

  2721 Gulf of Mexico Dr Unit 308, Longboat Key, FL 34228

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

  2721 Gulf of Mexico Dr Unit 308, Longboat Key, FL 34228

  Last Sold Summary

  • $1,476/SF
  • 14 Days On Market

  • Last Sold Price $1,305,000
  • Oct 29, 2024

  Last Listing Agent Cody Craig EXIT KING REALTY
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  $380,000

  2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228

  Unique location on the lawn at Longboat Key Club Moorings! A 70 x 21 slip that is conveniently located near the Marina Village. One of the boaters favorite location. Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228
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  $7,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

  Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
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  $2,200,000 Sold Jan 08, 2026

  1281 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228

  • 2 Beds
  • 3 Baths
  • 2,655 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $829/SF
  • 221 Days On Market

  Current Estimated Value $2,278,123

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  1281 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
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  Est $271,201 Not Listed For Sale

  2600 Harbourside Dr Unit Q5, Longboat Key, FL 34228

  • Studio
  • Built 1983

  2600 Harbourside Dr Unit Q5, Longboat Key, FL 34228

  Last Sold Summary

  • 10% Below List Price
  • 59 Days On Market

  • Last Sold Price $300,000
  • Jan 31, 2025

  Last Listing Agent Mark J Baron COLDWELL BANKER REALTY
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  $699,000 Pending

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

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  Under contract-accepting backup offers. NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  $2,500 Per Month

  • 1 Bed
  • 1 Bath
  • 689 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

  1-bed, 1-bath seasonal or annual rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
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  $3,100,000 Sold Jan 07, 2026

  435 L Ambiance Dr Unit K506, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,820 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $1,099/SF
  • 12 Days On Market

  Current Estimated Value $3,160,741

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  435 L Ambiance Dr Unit K506, Longboat Key, FL 34228
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  Est $1,586,502 Not Listed For Sale

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

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

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $1,131/SF
  • 8 Days On Market

  • Last Sold Price $1,700,000
  • Jul 23, 2024

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  $1,695,000

  • 3 Beds
  • 2 Baths
  • 2,317 Sq Ft

  690 Jungle Queen Way, Longboat Key, FL 34228

  LONGBOAT KEY HOME WITH WATER VIEWS. BEST PRICE PER SQ FT! Attention boating enthusiasts! Sailboat waterfront home in Longboat Key with Florida's favorite southern exposure. Park your boat on the stationary, or floating dock with a boat lift, 10,000 pounds boat lift, NEW seawall 125 ft., stainless ladder and fillet station. The outdoor kitchen is paved with a cedar pergola, a firepit, kitchen

  Reeny Kaney RE/MAX ALLIANCE GROUP

  690 Jungle Queen Way, Longboat Key, FL 34228
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  $3,300 Per Month

  • 1 Bed
  • 1 Bath
  • 798 Sq Ft
  • House for Rent

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228

  SPECIAL RENTAL INCENTIVES AVAILABLE. CALL TO DISCUSS. Stunning Bayfront and Marina views, this is a rare opportunity for a 1 bedroom, 1 bath, FURNISHED in a 55 + community on Longboat key . This is a beautifully designed and outfitted villa in the community of Twin Shores-located Mid Key(Close to both St. Armand's Circle and Anna Maria Island). Not only are you Sitting within Steps to Panoramic

  Joseph Patoray FINE PROPERTIES

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
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  $8,625,000 Sold Feb 23, 2026

  600 Wedge Ln, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 4,338 Sq Ft
  • Built 2016

  Last Sold Summary

  • 13% Below List Price
  • $1,988/SF
  • 65 Days On Market

  Current Estimated Value $9,367,814

  Last Listing Agent Debra Lichter SARASOTA BEACH TO BAY INC

  600 Wedge Ln, Longboat Key, FL 34228
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  Not Listed For Sale

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Built 1970

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  Last Sold Summary

  • $1,134/SF
  • 132 Days On Market

  • Last Sold Price $1,400,000
  • Feb 16, 2024

  Last Listing Agent Mark Midyett KELLER WILLIAMS ON THE WATER S
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  /24

  $670,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  843 Bayport Way, Longboat Key, FL 34228

  This exceptionally clean and well maintained 2-bedroom, 2-bath residence in Bayport Beach and Tennis Club is offered turnkey, ready for immediate enjoyment. Currently the lowest-priced unit in the community, it also presents a rare opportunity for a new owner to customize and renovate at their own pace—adding personal style while building value. Ideally positioned as a bright and private

  Camilo Perez HOME SOLD REALTY LLC

  843 Bayport Way, Longboat Key, FL 34228
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228

  Available for season 2027! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by

  Maureen Plichta STRINGER MANAGEMENT INC

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
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  $525,000 Sold Mar 13, 2026

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $490/SF
  • 87 Days On Market

  Current Estimated Value $611,040

  Last Listing Agent Marsha Winegarden WAGNER REALTY

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228
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  Est $844,359 Not Listed For Sale

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

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

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $1,502/SF
  • 4 Days On Market

  • Last Sold Price $987,000
  • Jun 15, 2023

  Last Listing Agent Ian Addy, PA Michael Saunders

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