Longboat Key, FL Homes

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  $629,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true

  John Esser KELLER WILLIAMS ON THE WATER S

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /13

  $4,500 Per Month

  • 4 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • House for Rent

  600 Russell St, Longboat Key, FL 34228

  Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room

  Gregory Koss WAGNER REALTY

  600 Russell St, Longboat Key, FL 34228
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  $1,725,000 Sold Feb 12, 2026

  2550 Harbourside Dr Unit 322, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,830 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $610/SF
  • 323 Days On Market

  Current Estimated Value $1,711,845

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2550 Harbourside Dr Unit 322, Longboat Key, FL 34228
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  /29

  Est $1,246,755 Not Listed For Sale

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1981

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Above List Price
  • $632/SF
  • 164 Days On Market

  • Last Sold Price $1,150,000
  • Feb 23, 2024

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
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  /16

  $6,999,000 Pending

  • Land
  • 38,332 Sq Ft
  • $7,953,409 per Acre

  6351 Gulf of Mexico Dr, Longboat Key, FL 34228

  Under contract-accepting backup offers. Rarely does an estate-sized Gulf-front lot of this stature become available on the northern end of Longboat Key. 6351 Gulf of Mexico Drive presents a truly exceptional 100-foot by 388-foot direct beachfront parcel — nearly 39,000 square feet of pristine Gulf of Mexico frontage. This distinguished property stands as one of the final remaining full beachfront

  Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  6351 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /65

  $12,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • House for Rent

  Unlisted Address

  Enjoy resort-style living on prestigious Longboat Key in this completely updated and renovated 3-bedroom, 2.5-bathroom villa. Located in Harbour Circle, an enclave of 42 villas in the guard-gated, maintenance-free, community of Bay Isles, this 2,396 SF open floorplan has soaring ceilings and an abundance of natural light through the new high-impact doors and windows that uplifts and illuminates.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  Unlisted Address
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  /2

  $30,300,000 Sold Jul 31, 2025

  845 Longboat Club Rd, Longboat Key, FL 34228

  • 6 Beds
  • 8 Baths
  • 19,300 Sq Ft
  • Built 2005

  Last Sold Summary

  • 13% Below List Price
  • $1,570/SF
  • 25 Days On Market

  Current Estimated Value $17,793,852

  Last Listing Agent Rich Polese COMPASS FLORIDA LLC

  845 Longboat Club Rd, Longboat Key, FL 34228
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  /13

  Not Listed For Sale

  17 Main Street Dr, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1985

  17 Main Street Dr, Longboat Key, FL 34228

  Last Sold Summary

  • $339/SF
  • 23 Days On Market

  • Last Sold Price $325,000
  • Sep 18, 2023

  Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S
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  /55

  $1,995,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,122 Sq Ft

  775 Longboat Club Rd Unit 408, Longboat Key, FL 34228

  Panoramic Gulf views and unforgettable sunsets take center stage in this beautifully updated fourth-floor residence at The Beaches of Longboat Key, offered fully furnished and ready for immediate enjoyment. Walls of glass and a wraparound terrace create a seamless connection to the water, bringing natural light deep into the open living spaces while framing panoramic coastal vistas. Spanning more

  Roger Pettingell COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 408, Longboat Key, FL 34228
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  /25

  $5,835 Per Month

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
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  $995,000 Sold Apr 24, 2026

  1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Built 1972

  Last Sold Summary

  • 9% Below List Price
  • $771/SF
  • 139 Days On Market

  Current Estimated Value $1,004,125

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228
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  /32

  Est $875,654 Not Listed For Sale

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228

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

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $1,567/SF
  • 142 Days On Market

  • Last Sold Price $1,018,500
  • Dec 06, 2023

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /30

  $370,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  620 Spanish Dr N, Longboat Key, FL 34228

  Some Photo's have been virtually staged. Don't miss this rare opportunity to own a renovated standalone villa with a lake view on Longboat Key! This very light, bright, and charming 2 bedroom 2 bath home is almost ready for occupancy at an exceptionally low price. As you enter the home, you can see a lovely lake view through the large back windows. The rear, shady, landscaped patio is a perfect

  Adrienne Scott MICHAEL SAUNDERS & COMPANY

  620 Spanish Dr N, Longboat Key, FL 34228
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  $15,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft
  • Condo for Rent

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

  C. Alison Hunter JENNETTE PROPERTIES INC

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  $715,000 Sold Dec 18, 2025

  2110 Harbourside Dr Unit 522, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,039 Sq Ft
  • Built 1988

  Last Sold Summary

  • 25% Below List Price
  • $351/SF
  • 302 Days On Market

  Current Estimated Value $742,008

  Last Listing Agent Andrew Vac RE/MAX ALLIANCE GROUP

  2110 Harbourside Dr Unit 522, Longboat Key, FL 34228
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  /54

  Est $797,688 Not Listed For Sale

  5265 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,453 Sq Ft
  • Built 1974

  5265 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $637/SF
  • 271 Days On Market

  • Last Sold Price $925,000
  • Apr 29, 2024

  Last Listing Agent Adam Cuffaro Michael Saunders
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  /67

  $750,000

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  490 N Shore Rd Unit 6, Longboat Key, FL 34228

  This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  490 N Shore Rd Unit 6, Longboat Key, FL 34228
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  /20

  $12,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft
  • Condo for Rent

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228

  Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip

  Jerome Henin HENIN REALTY

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228
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  $625,000 Sold Mar 09, 2026

  6901 Poinsetta Ave, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 2,173 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 2 Days On Market

  Current Estimated Value $659,488

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  6901 Poinsetta Ave, Longboat Key, FL 34228
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  /35

  Est $549,742 Not Listed For Sale

  3330 Gulf of Mexico Dr Unit 106-D, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • Built 1971

  3330 Gulf of Mexico Dr Unit 106-D, Longboat Key, FL 34228

  Last Sold Summary

  • 19% Below List Price
  • $613/SF
  • 117 Days On Market

  • Last Sold Price $678,000
  • Nov 06, 2023

  Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES
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  $11,900,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,689 Sq Ft

  1600 Harbor Sound Dr, Longboat Key, FL 34228

  Pre-Construction. To be built. Positioned directly across from the iconic St. Regis Longboat Key Resort, this exceptional waterfront residence offers immediate access to world-class amenities, pristine Gulf beaches, fine dining, and championship golf. Located within the exclusive double-gated Harbor Section of Bay Isles on Longboat Key, 1600 Harbor Sound Drive represents a rare convergence of

  Rinat Sikdar COLDWELL BANKER REALTY

  1600 Harbor Sound Dr, Longboat Key, FL 34228
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  $2,500 Per Month

  • 1 Bed
  • 1.5 Baths
  • 761 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find

  Brigette Marcus NEXTHOME EXCELLENCE

  3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  $1,550,000 Sold Aug 18, 2025

  2450 Harbourside Dr Unit 233, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft
  • Built 1990

  Last Sold Summary

  • 11% Below List Price
  • $503/SF
  • 68 Days On Market

  Current Estimated Value $1,621,463

  Last Listing Agent Linda Weber COLDWELL BANKER REALTY

  2450 Harbourside Dr Unit 233, Longboat Key, FL 34228
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  /45

  Est $4,807,581 Not Listed For Sale

  4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 3,640 Sq Ft
  • Built 2016

  4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228

  Last Sold Summary

  • 16% Below List Price
  • $1,566/SF
  • 12 Days On Market

  • Last Sold Price $5,700,000
  • Sep 06, 2023

  Last Listing Agent Pam Charron COMPASS FLORIDA LLC
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  $4,995,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  681 Old Compass Rd, Longboat Key, FL 34228

  Welcome to a crisp & clean Florida ranch. Located in popular Emerald Harbor which is a bayside enclave of just 82 homes. Homes are located on broad lagoon-style canals that provide direct boating access to Sarasota Bay. 20 ft. private Beach access is a real bonus for sunworshippers. This 3 bedroom 3.5 bath custom home blends Dutch Cape and West Indies architectural style. It is a split design

  Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  681 Old Compass Rd, Longboat Key, FL 34228
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  /31

  $17,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,556 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228

  Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
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  $900,000 Sold Nov 14, 2025

  3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,608 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $345/SF
  • 2 Days On Market

  Current Estimated Value $911,374

  Last Listing Agent Julie Klick MICHAEL SAUNDERS & COMPANY

  3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228
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  /37

  Est $287,007 Not Listed For Sale

  3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 712 Sq Ft
  • Built 1970

  3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228

  Last Sold Summary

  • 2% Below List Price
  • $413/SF
  • 2 Days On Market

  • Last Sold Price $294,000
  • Jun 15, 2023

  Last Listing Agent Dakota Magnus FLORIDA GALLERY REAL ESTATE
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  /54

  $4,950,000 Pending

  • 4 Beds
  • 6 Baths
  • 4,145 Sq Ft

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228

  Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers

  Toni Zarghami KW COASTAL LIVING III

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /21

  $5,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Townhouse for Rent

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip

  Victoria Campbell LPT REALTY LLC

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
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  $1,150,000 Sold Jan 08, 2026

  4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

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

  Last Sold Summary

  • 15% Below List Price
  • $693/SF
  • 117 Days On Market

  Current Estimated Value $1,183,202

  Last Listing Agent Ian Greenberg BRISTA REALTY LLC

  4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /19

  Est $317,658 Not Listed For Sale

  2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228

  • Studio
  • 1,820 Sq Ft

  2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • $206/SF
  • 62 Days On Market

  • Last Sold Price $375,000
  • Jul 28, 2023

  Last Listing Agent Jennifer Wilson LBRE LLC
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  $35,000 Pending

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228

  Welcome to Slip #2112 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6''Lx8'6''Wx7'2''H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228
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  $8,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,273 Sq Ft
  • Condo for Rent

  2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228

  LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
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  $879,000 Sold Apr 15, 2026

  2045 Gulf of Mexico Dr Unit M1309, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $695/SF
  • 2 Days On Market

  Current Estimated Value $883,623

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  2045 Gulf of Mexico Dr Unit M1309, Longboat Key, FL 34228
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  /79

  Est $395,169 Not Listed For Sale

  3810 Gulf of Mexico Dr Unit F102, Longboat Key, FL 34228

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

  3810 Gulf of Mexico Dr Unit F102, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Below List Price
  • $432/SF
  • 88 Days On Market

  • Last Sold Price $422,000
  • Sep 07, 2023

  Last Listing Agent Anna Lieggi REAL BROKER, LLC
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  /45

  $985,000

  • 3 Beds
  • 2.5 Baths
  • 2,219 Sq Ft

  2367 Harbour Oaks Dr, Longboat Key, FL 34228

  NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with

  Sandra Endres COLDWELL BANKER REALTY

  2367 Harbour Oaks Dr, Longboat Key, FL 34228
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  $11,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Condo for Rent

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  $435,000 Sold Dec 19, 2025

  1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 933 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Below List Price
  • $466/SF
  • 112 Days On Market

  Current Estimated Value $468,720

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228
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  /42

  Est $468,578 Not Listed For Sale

  781 Saint Judes Dr N Unit B, Longboat Key, FL 34228

  • 2 Beds
  • 1.5 Baths
  • 882 Sq Ft
  • Built 1972

  781 Saint Judes Dr N Unit B, Longboat Key, FL 34228

  Last Sold Summary

  • 9% Below List Price
  • $584/SF
  • 1 Day On Market

  • Last Sold Price $515,000
  • Jun 09, 2023

  Last Listing Agent Jonna Humphries WAGNER REALTY

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