$1,150,000
Under Contract
- 3 Beds
- 3.5 Baths
- 2,608 Sq Ft
3460 Winding Oaks Dr Unit 38, Longboat Key, FL 34228
Bruce Myer COLDWELL BANKER REALTY
11,338
Longboat Key, FL Homes
-
3460 Winding Oaks Dr Unit 38, Longboat Key, FL 34228
-
$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
-
$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 $1,930,658
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
100 Sands Point Rd Unit 114, Longboat Key, FL 34228 -
Est $754,158
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
Last Listing Agent Chevon Eaton CHEVON EATON
-
$1,648,000
- 2 Beds
- 2 Baths
- 1,598 Sq Ft
1211 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
1211 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228Leah George COLDWELL BANKER REALTY
-
$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
-
$1,875,000
Sold Jul 01, 2026230 Sands Point Rd Unit 3703, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,394 Sq Ft
- Built 1982
Last Sold Summary
- $1,345/SF
- 0 Days On Market
Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY
230 Sands Point Rd Unit 3703, Longboat Key, FL 34228 -
Est $9,065,684
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
Last Listing Agent Candy Swick CANDY SWICK & COMPANY
-
$599,000
$120K PRICE DROP- 2 Beds
- 2 Baths
- 1,172 Sq Ft
1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228John Esser KELLER WILLIAMS ON THE WATER S
-
$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 $1,233,164
Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
3030 Grand Bay Blvd Unit 323, 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
Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
-
$6,495,000
$504K PRICE DROP- Land
- 38,332 Sq Ft
- $7,380,682 per Acre
6351 Gulf of Mexico Dr, Longboat Key, FL 34228
6351 Gulf of Mexico Dr, Longboat Key, FL 34228 -
$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 $924,441
Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY
6841 Longboat Dr S, Longboat Key, FL 34228 -
Est $3,656,230
Not Listed For Sale1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
- 3 Beds
- 5 Baths
- 3,400 Sq Ft
- Built 1996
Last Sold Summary
- 278 Days On Market
Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
-
$699,000
$51K PRICE DROP- 2 Beds
- 2.5 Baths
- 1,350 Sq Ft
490 N Shore Rd Unit 6, Longboat Key, FL 34228
490 N Shore Rd Unit 6, Longboat Key, FL 34228JoDene Moneuse MICHAEL SAUNDERS & COMPANY
-
$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 $1,360,761
Last Listing Agent Alexis Smith-Frady COMPASS FLORIDA LLC
513 Bayport Way Unit 513, Longboat Key, FL 34228 -
Est $1,475,228
Not Listed For Sale2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228
- 3 Beds
- 3 Baths
- 2,462 Sq Ft
- Built 1984
Last Sold Summary
- 0 Days On Market
Last Listing Agent Terri Thacker MICHAEL SAUNDERS & COMPANY
-
$11,900,000
New Construction- 5 Beds
- 5.5 Baths
- 5,689 Sq Ft
1600 Harbor Sound Dr, Longboat Key, FL 34228
1600 Harbor Sound Dr, Longboat Key, FL 34228Rinat Sikdar COLDWELL BANKER REALTY
-
$12,000 Per Month
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Condo for Rent
4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
-
$2,200,000
Sold Jan 08, 20261281 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 $2,224,058
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
1281 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228 -
Not Listed For Sale
3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228
- 2 Beds
- 1 Bath
- 693 Sq Ft
- Built 2007
Last Sold Summary
- 61 Days On Market
Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
-
$449,000
$51K PRICE DROP Under Contract- 2 Beds
- 2 Baths
- 1,132 Sq Ft
600 Sutton Place Unit 302, Longboat Key, FL 34228
600 Sutton Place Unit 302, Longboat Key, FL 34228Christina Weger COLDWELL BANKER REALTY
-
$25,000 Per Month
- 3 Beds
- 3 Baths
- 3,230 Sq Ft
- House for Rent
690 Old Compass Rd, Longboat Key, FL 34228
690 Old Compass Rd, Longboat Key, FL 34228Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size
Teresa Ribaudo JENNETTE PROPERTIES INC
-
$1,690,000
Sold May 27, 2026340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228
- 3 Beds
- 3 Baths
- 2,365 Sq Ft
- Built 1991
Last Sold Summary
- 35% Below List Price
- $715/SF
- 333 Days On Market
Current Estimated Value $1,693,040
Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY
340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228 -
Est $781,396
Not Listed For Sale5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228
- 3 Beds
- 3 Baths
- 1,498 Sq Ft
- Built 1974
Last Sold Summary
- 58 Days On Market
Last Listing Agent Jens Pinkernell DOUGLAS ELLIMAN
-
$1,000,000
- Land
- 19,602 Sq Ft
- $2,222,222 per Acre
6608 Gulf of Mexico Dr, Longboat Key, FL 34228
6608 Gulf of Mexico Dr, Longboat Key, FL 34228 -
$11,950 Per Month
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
- Condo for Rent
2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room.Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom,
Andrey markov ANMARK REALTY LLC
-
$3,100,000
Sold Jan 07, 2026435 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 $3,185,241
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
435 L Ambiance Dr Unit K506, Longboat Key, FL 34228 -
Est $2,352,730
Not Listed For Sale210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,284 Sq Ft
- Built 1982
Last Sold Summary
- 6 Days On Market
Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY
-
$12,950,000
New Construction $300K PRICE DROP- 3 Beds
- 3.5 Baths
- 4,187 Sq Ft
1561 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
1561 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228Michael Moulton MICHAEL SAUNDERS & COMPANY
-
$15,000 Per Month
- 2 Beds
- 2.5 Baths
- 2,135 Sq Ft
- Condo for Rent
1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228Gorgeous gulf front vacation rental available now through 2027!! You will love this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
-
$8,625,000
Sold Feb 23, 2026600 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 $8,616,364
Last Listing Agent Debra Lichter SARASOTA BEACH TO BAY INC
600 Wedge Ln, Longboat Key, FL 34228 -
Est $1,141,173
Not Listed For Sale1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
- 2 Beds
- 2.5 Baths
- 1,859 Sq Ft
- Built 1982
Last Sold Summary
- 155 Days On Market
Last Listing Agent Jonathan Fox MICHAEL SAUNDERS & COMPANY
-
$2,050,000
- 3 Beds
- 3.5 Baths
- 3,083 Sq Ft
2450 Harbourside Dr Unit 244, Longboat Key, FL 34228
2450 Harbourside Dr Unit 244, Longboat Key, FL 34228Ian Addy, PA MICHAEL SAUNDERS & COMPANY
-
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,409 Sq Ft
- Property for Rent
1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of
Marni Hayden CHROME REALTY LLC
-
$525,000
Sold Mar 13, 20264350 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 $520,590
Last Listing Agent Marsha Winegarden WAGNER REALTY
4350 Chatham Dr Unit 307, Longboat Key, FL 34228 -
Est $832,829
Not Listed For Sale1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
- 2 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 1981
Last Sold Summary
- 123 Days On Market
Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY
Showing Results 321 - 360, Page 9 of 18
Copyright © 2026 CoStar Group
