Gated Communities in Longboat Key, FL: Homes for Sale

This page tracks every Longboat Key listing whose MLS record reports a gated community (manned gate, unmanned gate or security gate), by community, with live counts and asking prices, and the fee questions that come with the gate.

133 homes in gated communities are for sale or pending in Longboat Key, FL today across 53 communities. The median asking price is $980,000, from $39,900 to $13,000,000. Listings in Longboat Key without that feature have a median of $750,000. Most listings right now: Longboat Harbour (9), Longboat Key Moorings Marina (9), Longboat Key Moorings (8). Updated September 28, 2026 from the MLS.

Live gated community homes in Longboat Key: the listings

108 active listings carry the flag today (43% of Longboat Key inventory), median asking $955,000, $717/sq ft, median 132 days on market. Photo cards link to the listing; refreshed nightly.

Newest gated community homes in Longboat Key

1591 Gulf Of Mexico Drive #312, gated community for sale in Longboat Key
$4,290,000 New
2 bd · 2.5 ba · 2,154 sq ft · built 2024
1591 Gulf Of Mexico Drive #312, 34228
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2600 Harbourside Drive #B-16, gated community for sale in Longboat Key
$500,000 New
· built 1985
2600 Harbourside Drive #B-16, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of LBRE LLC
2600 Harbourside Drive #L-11, gated community for sale in Longboat Key
$425,000 New
· built 1985
2600 Harbourside Drive #L-11, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of LBRE LLC
2800 Harbourside Drive #E-07, gated community for sale in Longboat Key
$300,000 New
· built 1985
2800 Harbourside Drive #E-07, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of LBRE LLC
2800 Harbourside Drive Drive #M-10, gated community for sale in Longboat Key
$289,000 New
· built 1999
2800 Harbourside Drive Drive #M-10, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of LBRE LLC
2600 Harbourside Drive #P-07, gated community for sale in Longboat Key
$225,000 New
· built 1985
2600 Harbourside Drive #P-07, 34228
Listing courtesy of LBRE LLC
2600 Harbourside Drive #Q-10, gated community for sale in Longboat Key
$225,000 New
· built 1985
2600 Harbourside Drive #Q-10, 34228
Listing courtesy of LBRE LLC
2600 Harbourside Drive #O-07, gated community for sale in Longboat Key
$216,000 New
· built 1985
2600 Harbourside Drive #O-07, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of LBRE LLC
1561 Gulf Of Mexico Drive #404, gated community for sale in Longboat Key
$12,750,000 New
3 bd · 3.5 ba · 4,967 sq ft · built 2024
1561 Gulf Of Mexico Drive #404, 34228
Listing courtesy of MICHAEL SAUNDERS & COMPANY
455 Longboat Club Road #905, gated community for sale in Longboat Key
$5,295,000 New
3 bd · 3.5 ba · 2,880 sq ft · built 1990
455 Longboat Club Road #905, 34228
Listing courtesy of DEVELOPERS REALTY LBK, INC
3530 Mistletoe Lane, gated community for sale in Longboat Key
$2,675,000 New
4 bd · 3.5 ba · 3,102 sq ft · built 1991
3530 Mistletoe Lane, 34228
Listing courtesy of COLDWELL BANKER REALTY
1241 Gulf Of Mexico Drive #303, gated community for sale in Longboat Key
$2,495,000 New
3 bd · 4 ba · 3,045 sq ft · built 1996
1241 Gulf Of Mexico Drive #303, 34228
Listing courtesy of DEVELOPERS REALTY LBK, INC
1241 Gulf Of Mexico Drive #608, gated community for sale in Longboat Key
$2,200,000 New
2 bd · 4 ba · 2,965 sq ft · built 1996
1241 Gulf Of Mexico Drive #608, 34228
Listing courtesy of RE/MAX ALLIANCE GROUP
1211 Gulf Of Mexico Drive #403, gated community for sale in Longboat Key
$1,695,000 New
2 bd · 2 ba · 1,585 sq ft · built 1985
1211 Gulf Of Mexico Drive #403, 34228
Listing courtesy of COMPASS FLORIDA LLC
2101 Harbourside Drive #1103, gated community for sale in Longboat Key
$1,495,000 New
3 bd · 2.5 ba · 2,204 sq ft · built 1984
2101 Harbourside Drive #1103, 34228
Listing courtesy of MICHAEL SAUNDERS & COMPANY
1241 Gulf Of Mexico Drive #109, gated community for sale in Longboat Key
$989,000 New
2 bd · 2.5 ba · 2,000 sq ft · built 1996
1241 Gulf Of Mexico Drive #109, 34228
Listing courtesy of COLDWELL BANKER REALTY
2020 Harbourside Drive #442, gated community for sale in Longboat Key
$699,000 New
2 bd · 2 ba · 1,192 sq ft · built 1984
2020 Harbourside Drive #442, 34228
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2600 Harbourside Drive #L-05, gated community for sale in Longboat Key
$425,000 New
· built 1985
2600 Harbourside Drive #L-05, 34228
Listing courtesy of LBRE LLC
3360 Bayou Sound, gated community for sale in Longboat Key
$4,699,999 New
5 bd · 4.5 ba · 4,000 sq ft · built 2026
3360 Bayou Sound, 34228
Listing courtesy of COLDWELL BANKER REALTY
1075 Gulf Of Mexico Drive #205, gated community for sale in Longboat Key
$1,099,000 New
3 bd · 2 ba · 1,819 sq ft · built 1981
1075 Gulf Of Mexico Drive #205, 34228
Listing courtesy of COLDWELL BANKER REALTY
1075 Gulf Of Mexico Drive #303, gated community for sale in Longboat Key
$925,000 New
2 bd · 2 ba · 1,503 sq ft · built 1981
1075 Gulf Of Mexico Drive #303, 34228
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2321 Harbour Oaks Drive, gated community for sale in Longboat Key
$835,000
3 bd · 2.5 ba · 2,478 sq ft · built 1986
2321 Harbour Oaks Drive, 34228
Listing courtesy of WHITE SANDS REALTY GROUP FL
3040 Grand Bay Boulevard #225, gated community for sale in Longboat Key
$1,349,000
3 bd · 3.5 ba · 2,250 sq ft · built 1996
3040 Grand Bay Boulevard #225, 34228
Listing courtesy of COLDWELL BANKER REALTY
4370 Chatham Drive #304, gated community for sale in Longboat Key
$425,000
2 bd · 2 ba · 1,072 sq ft · built 1969
4370 Chatham Drive #304, 34228
Listing courtesy of PREFERRED SHORE LLC
3080 Grand Bay Boulevard #512, gated community for sale in Longboat Key
$549,000
2 bd · 2 ba · 1,276 sq ft · built 1996
3080 Grand Bay Boulevard #512, 34228
Listing courtesy of COLDWELL BANKER REALTY
4390 Exeter Drive #107, gated community for sale in Longboat Key
$425,000
2 bd · 2 ba · 1,152 sq ft · built 1970
4390 Exeter Drive #107, 34228
Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
2800 Harbourside Drive #E-12, gated community for sale in Longboat Key
$300,000
· built 1985
2800 Harbourside Drive #E-12, 34228
Listing courtesy of LBRE LLC
4340 Falmouth Drive #D-204, gated community for sale in Longboat Key
$479,000
2 bd · 2 ba · 1,072 sq ft · built 1969
4340 Falmouth Drive #D-204, 34228
Listing courtesy of WAGNER REALTY
2350 Harbour Oaks Drive, gated community for sale in Longboat Key
$950,000
3 bd · 2.5 ba · 2,451 sq ft · built 1987
2350 Harbour Oaks Drive, 34228
Listing courtesy of CORCORAN DWELLINGS REALTY
2600 Harbourside Drive #P-05, gated community for sale in Longboat Key
$200,000
2600 Harbourside Drive #P-05, 34228
8177 - Longboat Key Moorings Marina
Listing courtesy of RIVER HILLS PROPERTIES, LLC B

The most expensive gated community homes in Longboat Key

ListingAskingSq ftCommunity
1561 Gulf Of Mexico Drive #304$13,000,0004,967—
6680 Gulf Of Mexico Drive$12,900,0006,408—
1561 Gulf Of Mexico Drive #403$12,825,0004,187—
1561 Gulf Of Mexico Drive #404$12,750,0004,967—
1600 Harbor Sound Drive$11,900,0005,689—
2251 Gulf Of Mexico Drive #301$5,999,0003,921—
455 Longboat Club Road #905$5,295,0002,880—
3606 Fair Oaks Place$4,999,0003,842—
3360 Bayou Sound$4,699,9994,000—
1591 Gulf Of Mexico Drive #413$4,429,0002,154—

Gated Community Homes by price

BandFor saleShare
Under $300K1211%
$300K–$500K1918%
$500K–$750K109%
$750K–$1M1918%
$1M+4844%

Longboat Key gated community homes by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

CommunityGated Community HomesNew buildMedian listFrom
Longboat Harbour90$479,000$307,000
Longboat Key Moorings Marina90$250,000$225,000
Longboat Key Moorings80$412,500$189,000
St. Regis Longboat Key62$8,589,500$2,750,000
Bay Isles62$4,175,000$1,100,000
Beachplace Iii60$1,199,000$599,000
Queens Harbour50$2,650,000$2,100,000
Islander Club Of Longboat50$950,000$625,000
Beachplace Ii50$775,000$599,000
Water Club 01 At Longboat Key30$2,200,000$1,050,000
Marina Bay30$1,995,000$1,800,000
Promenade30$1,695,000$1,648,000
Sands Point30$980,000$915,000
Inn On The Beach Ph Ii30$950,000$899,900
Fairway Bay 130$769,000$497,000
Sanctuary Iv20$3,507,500$3,265,000
Villa Di Lancia Ph 120$2,172,500$1,995,000
Grand Bay 120$1,462,000$1,095,000
Grand Bay 220$1,404,500$1,349,000
Inn On The Beach Ph I20$1,393,000$996,000
Players Club Iv20$1,007,500$975,000
Seaplace I20$912,500$675,000
Privateer South20$906,450$863,900
Harbour Oaks 220$892,500$835,000
Fairway Bay20$536,000$449,000
Seaplace Vi20$509,000$449,000
Rauch10$12,900,000$12,900,000
Lighthouse Point10$6,995,000$6,995,000
Aria Longboat Key10$5,999,000$5,999,000
Pierre10$5,295,000$5,295,000
La Firenza10$4,700,000$4,700,000
Weston Pointe10$3,100,000$3,100,000
L Ambiance 110$2,950,000$2,950,000
Sanctuary Iv Longboat Key10$2,899,000$2,899,000
Coreys Landing10$2,675,000$2,675,000
L Ambiance At Longboat Key Club10$2,580,000$2,580,000
Beaches Of Longboat Key10$2,145,000$2,145,000
Sanctuary Iii10$2,100,000$2,100,000
Emerald Pointe South10$1,950,000$1,950,000
Harbor Oaks Ph I & Ii10$1,495,000$1,495,000
Beaches Of Longboat Key Ph-110$1,495,000$1,495,000
Players Club I10$1,395,000$1,395,000
Tangerine Bay Club10$1,044,000$1,044,000
Privateer North10$995,000$995,000
Water Club At Longboat Key10$989,000$989,000
Seaplace Iv10$949,000$949,000
Beachplace I10$875,000$875,000
Seaplace Iii10$849,000$849,000
Fairway Bay 2 Ph 110$699,000$699,000
Grand Bay 510$549,000$549,000
Seaplace V10$485,000$485,000
Longboat Key Moorings Marina 210$350,000$350,000
Boathouse On Longboat10$39,900$39,900

What the gate costs and what it actually does

A gate is an HOA amenity, so it shows up in dues: an unmanned keypad or transponder gate adds little; a 24-hour manned gate is a six-figure annual staffing line shared by the homeowners, and the roads behind it are usually private, which means the association, not the county, pays to repave them. Ask for the current HOA budget and reserve study, whether the roads are private, and whether a gate or road assessment is pending. The MLS field records the gate, not its staffing, so confirm which kind it is before you value it. Our true cost of ownership calculator puts HOA dues, taxes and insurance into one monthly number.

Questions to ask about any gated-community listing

Is the gate manned, and during what hours? Are the roads private, and what do the reserves look like for repaving? What are the HOA dues today and what did they run three years ago? Is there a CDD or a special assessment on the books? What are the guest-access and delivery rules? A local agent who works the community will know which gates are staffed and which associations are underfunded.

Common questions

How many homes in gated communities are for sale in Longboat Key?
As of September 28, 2026, 133 Longboat Key, FL listings whose MLS record reports a gated community are active or pending, across 53 communities. The count updates with every MLS refresh.
What do gated community homes cost in Longboat Key?
The median asking price today is $980,000, with listings from $39,900 to $13,000,000. Longboat Key listings without that feature have a median of $750,000.
Which Longboat Key community has the most gated community homes for sale?
Longboat Harbour has the most right now (9), followed by Longboat Key Moorings Marina (9), Longboat Key Moorings (8), St. Regis Longboat Key (6).
Are gated communities more expensive to own?
Usually the HOA dues are higher, because the gate, any guard staffing and the private roads behind it are paid for by the homeowners. Home prices vary by community; the table above shows the asking prices in each gated community with listings today, and the HOA figure on each community's own guide shows what the dues actually run.

Keep exploring Longboat Key

Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Longboat Key, FL whose MLS record reports a gated community. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.

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