$1,349,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 1,679 Sq Ft
1445 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
Kathy Callahan MICHAEL SAUNDERS & COMPANY
$1,349,000 Open Sun 1PM - 4PM
1445 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
Kathy Callahan MICHAEL SAUNDERS & COMPANY
$3,975 per month
3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
A perfect island getaway. This well appointed and updated Longboat Key condo is available as a six or seven month rental from late June through January. Located Bay side, you'll enjoy a sparkling pool, tennis, kayak launch, fishing pier, grill area and clubhouse, plus deeded beach access is 250ft from your front door. There's plenty of room to spread out with an open, split floor plan and a huge
Rosemarie McKee COLDWELL BANKER REALTY
$200,000 Sold Jun 27, 2025
2800 Harbourside Dr Unit M-01, Longboat Key, FL 34228
2800 Harbourside Dr Unit M-01, Longboat Key, FL 34228Est $202,137 Not Listed For Sale
2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228
2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228$1,595,000
1055 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
Jim Weingart COLDWELL BANKER REALTY
$7,000 per month
4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! 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, large walk-in closets and
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$580,000 Sold Jun 25, 2025
681 Fox St, Longboat Key, FL 34228
681 Fox St, Longboat Key, FL 34228Est $359,024 Not Listed For Sale
2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228
2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228$425,000
5310 Gulf of Mexico Dr Unit 18, Longboat Key, FL 34228
George Sanchez EZ CHOICE REALTY
$11,700 per month
448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
LONGBOAT KEY SOUTH...This is a 3 bedroom, 2 bathroom, end unit on the main floor which makes this unit light & bright with extra windows. The interior is decorated tastefully with warm neutral colors. Beautiful views of Sarasota Bay. Fully equipped kitchen which features stainless appliances, granite countertops and wood cabinets. There is a king size bed in the main bedroom and a queen bed in
Teresa Ribaudo JENNETTE PROPERTIES INC
$661,000 Sold Jun 25, 2025
3630 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
3630 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228Est $604,696 Not Listed For Sale
5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228
5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228$449,000
6800 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC
$5,000 per month
4780 Gulf of Mexico Dr, Longboat Key, FL 34228
Rented January-April 2026. This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of
Joseph Stephens ONE STEP AHEAD REALTY INC
$69,000 Sold Jun 24, 2025
408 Gulf of Mexico Dr Unit 2233, Longboat Key, FL 34228
408 Gulf of Mexico Dr Unit 2233, Longboat Key, FL 34228Est $1,124,446 Not Listed For Sale
1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228$3,995,000
2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228
Steve and Janet Walter MICHAEL SAUNDERS & COMPANY
$10,500 per month
4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease JANUARY and FEBRUARY 2026 with the option to include APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath
Norma Mladineo COLDWELL BANKER REALTY
$1,000,000 Sold Jun 23, 2025
3540 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
3540 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228Est $667,623 Not Listed For Sale
4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228$2,595,000
260 N Shore Rd Unit 2, Longboat Key, FL 34228
Reid Murphy DEVELOPERS REALTY LBK, INC
$8,500 per month
4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
BEAUTIFULLY RENOVATED VACATION RENTAL: Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$940,000 Sold Jun 23, 2025
1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228Est $942,387 Not Listed For Sale
1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228$1,350,000
4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
Ian Greenberg BRISTA REALTY LLC
$6,500 per month
1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
AVAILABLE ONLY FOR AFTER APRIL 2026 SEASON! MINIMUM 2 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give
Brigette Marcus NEXTHOME EXCELLENCE
$325,000 Sold Jun 20, 2025
29 Main Street Dr, Longboat Key, FL 34228
29 Main Street Dr, Longboat Key, FL 34228Est $776,163 Not Listed For Sale
1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228$45,000
408 Gulf of Mexico Dr Unit 2119, Longboat Key, FL 34228
Peter Snyder COLDWELL BANKER REALTY
$6,000 per month
3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
PORTOBELLO - SHORT TERM RENTAL - 2 Bedrooms, 2 Baths in the #1 Beach of Florida, white quartz sand and dreamy sunsets Ample and chic apartment fully furnished to enjoy vacation time. 2 Parking spots
Valeria Fucaraccio Benesch Brokers, LLC
$62,500 Sold Jun 20, 2025
408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228
408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228Est $1,943,030 Not Listed For Sale
2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228$649,000
1945 Gulf of Mexico Dr Unit M2213, Longboat Key, FL 34228
Michael Renick MANGROVE REALTY ASSOCIATES
$5,500 per month
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor
Scott Nold TNG PROPERTY MANAGEMENT
$207,000 Sold Jun 20, 2025
2600 Harbourside Dr Unit O-05, Longboat Key, FL 34228
2600 Harbourside Dr Unit O-05, Longboat Key, FL 34228Est $846,362 Not Listed For Sale
4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228$2,925,000 Open Sun 11AM - 1:30PM
3310 Bayou Rd, Longboat Key, FL 34228
Ryan Heers COLDWELL BANKER REALTY
$15,000 per month
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
$416,000 Sold Jun 20, 2025
250 Sands Point Rd Unit 5105, Longboat Key, FL 34228
250 Sands Point Rd Unit 5105, Longboat Key, FL 34228Est $1,160,767 Not Listed For Sale
1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228Showing Results 321 - 360, Page 9 of 18