$1,299,000
- 2 Beds
- 2 Baths
- 1,503 Sq Ft
1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
Roger Pettingell COLDWELL BANKER REALTY
11,645
Longboat Key, FL Homes
-
1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
-
$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
1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228An 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
-
$925,000
Sold Jul 10, 20255055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 1973
Last Sold Summary
- 27% Below List Price
- $570/SF
- 25 Days On Market
Current Estimated Value $978,910
Last Listing Agent Nathan Mathers PREMIER SOTHEBY'S INTERNATIONAL REALTY
5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228 -
Not Listed For Sale3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1977
Last Sold Summary
- 65 Days On Market
-
$995,000
- Land
- 6,969 Sq Ft
- $6,218,750 per Acre
6800 Longboat Dr S, Longboat Key, FL 34228
6800 Longboat Dr S, Longboat Key, FL 34228 -
$5,500 Per Month
- 2 Beds
- 2 Baths
- 1,399 Sq Ft
- House for Rent
957 Spanish Dr N, Longboat Key, FL 34228
957 Spanish Dr N, Longboat Key, FL 34228AVAILABLE 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
-
$350,000
Sold Sep 15, 2025655 Spanish Way, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,241 Sq Ft
- Built 1968
Last Sold Summary
- 11% Below List Price
- $282/SF
- 74 Days On Market
Current Estimated Value $369,730
Last Listing Agent Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY
655 Spanish Way, Longboat Key, FL 34228 -
Not Listed For Sale
90 Main Street Dr, Longboat Key, FL 34228
- 1 Bed
- 1 Bath
- 568 Sq Ft
- Built 1959
Last Sold Summary
- 21 Days On Market
-
$435,000
- 2 Beds
- 2 Baths
- 1,327 Sq Ft
711 Spanish Dr S, Longboat Key, FL 34228
711 Spanish Dr S, Longboat Key, FL 34228Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY
-
$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
4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228SEASONAL: 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
-
$2,500,000
Sold Apr 16, 2026600 Dream Island Rd, Longboat Key, FL 34228
- 3 Beds
- 2 Baths
- 1,982 Sq Ft
- Built 1970
Last Sold Summary
- 30% Below List Price
- $1,261/SF
- 276 Days On Market
Current Estimated Value $2,353,137
Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC
600 Dream Island Rd, Longboat Key, FL 34228 -
Est $1,341,936
Not Listed For Sale2525 Gulf of Mexico Dr Unit 11B, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,491 Sq Ft
- Built 1972
Last Sold Summary
- 96 Days On Market
-
$1,499,000
$726K PRICE DROP- 3 Beds
- 3 Baths
- 3,229 Sq Ft
721 Binnacle Point Dr, Longboat Key, FL 34228
721 Binnacle Point Dr, Longboat Key, FL 34228James Frost KINCAID REALTY
-
$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
747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228GORGEOUS 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
-
$1,500,000
Sold Mar 11, 20262425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
- Built 1973
Last Sold Summary
- 3% Above List Price
- $1,020/SF
Current Estimated Value $1,478,582
Last Listing Agent Robert Delaney MICHAEL SAUNDERS & COMPANY
2425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228 -
Est $1,374,680
Not Listed For Sale1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,172 Sq Ft
- Built 1981
Last Sold Summary
- 20 Days On Market
-
$2,995,000
$455K PRICE DROP Pending- 3 Beds
- 3.5 Baths
- 2,634 Sq Ft
435 L Ambiance Dr Unit J704, Longboat Key, FL 34228
435 L Ambiance Dr Unit J704, Longboat Key, FL 34228Reid Murphy DEVELOPERS REALTY LBK, INC
-
$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
1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228Welcome 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
-
$1,430,000
Sold Jun 03, 20261485 Gulf of Mexico Dr Unit 110, Longboat Key, FL 34228
- 2 Beds
- 3 Baths
- 1,971 Sq Ft
- Built 1981
Last Sold Summary
- 13% Below List Price
- $726/SF
- 76 Days On Market
Current Estimated Value $1,498,046
Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
1485 Gulf of Mexico Dr Unit 110, Longboat Key, FL 34228 -
Est $1,383,743
Not Listed For Sale1965 Gulf of Mexico Dr Unit G5-201 & 203, Longboat Key, FL 34228
- 4 Beds
- 3 Baths
- 2,425 Sq Ft
- Built 1977
Last Sold Summary
- 186 Days On Market
-
$849,900
$400K PRICE DROP Pending- 2 Beds
- 2 Baths
- 1,393 Sq Ft
4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228Donna Wrobel BERKSHIRE HATHAWAY HOMESERVICE
-
$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
3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 342281-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
-
$1,100,000
Sold Feb 17, 20262110 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 $1,137,053
Last Listing Agent Scott Rickards RE/MAX ALLIANCE GROUP
2110 Harbourside Dr Unit 558, Longboat Key, FL 34228 -
Not Listed For Sale
3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 680 Sq Ft
- Built 1974
Last Sold Summary
- 26 Days On Market
-
$5,999,000
$251K PRICE DROP- 4 Beds
- 4.5 Baths
- 3,921 Sq Ft
2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228
2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228Rachel Woodruff HOUSE MATCH
-
$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
3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228SPECIAL 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
-
$2,000,000
Sold Apr 10, 2026100 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 $1,961,874
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
100 Sands Point Rd Unit 114, Longboat Key, FL 34228 -
Est $1,421,664
Not Listed For Sale1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
- 2 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Built 1981
Last Sold Summary
- 39 Days On Market
-
$1,000,000
- Land
- 19,166 Sq Ft
- $2,272,727 per Acre
6604 Gulf of Mexico Dr, Longboat Key, FL 34228
6604 Gulf of Mexico Dr, Longboat Key, FL 34228 -
$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
3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228Available 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
-
$1,200,000
Sold May 01, 20263030 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 $1,447,879
Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
3030 Grand Bay Blvd Unit 323, Longboat Key, FL 34228 -
Est $832,779
Not Listed For Sale750 Saint Judes Dr N, Longboat Key, FL 34228
- 3 Beds
- 2 Baths
- 1,246 Sq Ft
- Built 1958
Last Sold Summary
- 134 Days On Market
-
$2,595,000
$195K PRICE DROP Pending- 5 Beds
- 5 Baths
- 4,510 Sq Ft
3408 Fair Oaks Ln, Longboat Key, FL 34228
3408 Fair Oaks Ln, Longboat Key, FL 34228Bruce Myer COLDWELL BANKER REALTY
-
$10,000 Per Month
- 2 Beds
- 2.5 Baths
- 1,957 Sq Ft
- Condo for Rent
1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with
Brad Wilson M&M PROPERTY MANAGEMENT GROUP
-
$900,000
Sold Apr 27, 20266841 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 $981,742
Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY
6841 Longboat Dr S, Longboat Key, FL 34228 -
Est $8,447,597
Not Listed For Sale60 Lighthouse Point Dr, Longboat Key, FL 34228
- 5 Beds
- 8 Baths
- 7,170 Sq Ft
- Built 2000
Last Sold Summary
- 185 Days On Market
-
$22,500,000
$3M PRICE DROP- 6 Beds
- 9 Baths
- 9,243 Sq Ft
612 Juan Anasco Dr, Longboat Key, FL 34228
612 Juan Anasco Dr, Longboat Key, FL 34228Charles Buky COLDWELL BANKER REALTY
-
$7,200 Per Month
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- Condo for Rent
4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
-
$1,400,000
Sold Feb 18, 2026513 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 $1,395,442
Last Listing Agent Alexis Smith-Frady COMPASS FLORIDA LLC
513 Bayport Way Unit 513, Longboat Key, FL 34228 -
Not Listed For Sale
3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 880 Sq Ft
- Built 1974
Last Sold Summary
- 0 Days On Market
Showing Results 281 - 320, Page 8 of 18
Copyright © 2026 CoStar Group
