Longboat Key, FL Real Estate | Explore Luxury Homes

Longboat Key, FL -- At a Glance

Population

7,512

Median Age

71.5 years

ZIP Code

34228

Avg. Individual Income

$138,251

Listing Agent

Roger Pettingell

Rental Policy

30-day minimum (no STR)

Longboat Key Zone Guide -- South vs. North

Zone	Vibe	Property Type	Key Communities	Price Range
South Key	Resort, Golf Club, exclusive gated	St. Regis Residences, Country Club Shores	The St. Regis Longboat Key, Bay Isles, Country Club Shores	[INSERT: current South Key range]
Mid-Key	Panoramic Gulf views, high-rise	Luxury condos and co-ops	Water Club, Promenade, Grand Bay, L'Ambiance	[INSERT: current Mid-Key range]
North Key	Old Florida charm, low-rise, private	Private estates, low-rise condos	The Village, Whitney Beach area, Queen's Harbor	[INSERT: current North Key range]

Price ranges updated from active MLS. Verify current figures with Roger Pettingell. MLS data

Looking for a Longboat Key Realtor?

Roger Pettingell has more Longboat Key closed sales than any other individual agent in Sarasota. He knows every zone, every building, and every canal on this island.

Contact Roger Pettingell

Explore Sarasota's Barrier Islands

Who is the best real estate agent on Longboat Key?

Roger Pettingell is consistently ranked the top-producing individual agent on Longboat Key, with over $200 million in closed sales volume and decades of experience representing buyers and sellers across every zone of the island. He has sold more homes on Longboat Key than any other agent and knows the specific attributes of each community -- from the South Key gated estates near the St. Regis to the high-rise condos along Mid-Key and the Old Florida private estates on the North End. For buyers, he provides off-market access. For sellers, he brings the buyer network that moves luxury property at full price.

Is Longboat Key a good place to buy real estate?

Longboat Key is one of the most consistently desirable barrier islands in Florida for luxury real estate investment. Its 30-day minimum rental policy protects property values and neighborhood character, making it ideal for end-users, snowbirds, and buyers who prioritize equity appreciation over short-term rental income. The island's limited land supply, Gulf-front positioning, and access to Sarasota's arts and cultural amenities create sustained demand. The St. Regis resort presence on the south end has further elevated the island's profile for ultra-luxury buyers.

What is the difference between North and South Longboat Key?

South Longboat Key (the gated "The Gates" area) is characterized by resort-adjacent exclusivity -- the St. Regis Longboat Key, Country Club Shores, and Bay Isles are concentrated here, offering golf club access and the highest price per square foot on the island. Mid-Key features panoramic Gulf-view high-rises including Water Club, Grand Bay, and L'Ambiance. North Longboat Key (The Village) has an Old Florida atmosphere with low-rise estates and private residences, attracting buyers who prefer a quieter, less resort-driven lifestyle at slightly lower price points than the south end.

What are the rental rules on Longboat Key?

Longboat Key enforces a 30-day minimum rental policy, which prohibits short-term rentals (Airbnb, VRBO, or weekly rentals) throughout the island. This ordinance is one of the defining factors that separates Longboat Key from Siesta Key, which allows weekly and daily rentals. The 30-day minimum makes Longboat Key more attractive to buyers focused on a quiet residential experience and long-term appreciation rather than rental cash flow.

Where is Longboat Key located?

Longboat Key is a barrier island located west of Sarasota, Florida, in Sarasota County. It stretches 12 miles along the Gulf of Mexico, connected to the mainland via bridges. The island runs from Sarasota Bay on the east to the Gulf on the west, with Sarasota directly to the south and Manatee County at the north end. ZIP code is 34228. It is approximately 10 minutes from downtown Sarasota by car.

How far is Longboat Key from Siesta Key?

Longboat Key and Siesta Key are separated by approximately 15-20 minutes of driving time (around 12 miles), passing through downtown Sarasota. They are not directly connected -- you travel via the mainland. Despite being neighboring barrier islands in the Sarasota area, they have distinctly different characters: Longboat Key is quieter, more exclusive, and resort-adjacent, while Siesta Key is more tourist-oriented with weekly rental activity and the famous white-quartz sand beach that draws significant seasonal traffic.

Welcome to Longboat Key

Idyllic island community with Gulf and Sarasota Bay views

Longboat Key (34228) is a waterfront community on a barrier island between the Gulf of Mexico and Sarasota Bay. Gorgeous white sand beaches run for 11 miles along the coastline.

However, Longboat Key is not a single neighborhood; it is a diverse collection of lifestyles. Divided by man-made canals and defined by its proximity to either the Gulf (Beach) or the Bay (Boating), choosing the right "Zone" is your first step.

The Longboat Key Lifestyle Map

Before you explore the neighborhoods below, decide which "Zone" fits your vision.

Zone	The Vibe	Real Estate Type
South Key (The Gates)	Resort & Golf Club	The St. Regis / Country Club Shores
Mid-Key	Panoramic Views	High-Rise Condos (Water Club, Promenade)
North Key (The Village)	Old Florida Charm	Low-Rise / Private Estates

Dining, Entertainment & Shopping

Longboat Key is home to a fantastic array of restaurants that combine sublime cuisine with mesmerizing waterfront views.

The Shore: Serves seafood specialties such as Key West shrimp and scallop risotto.
The Drydock Waterfront Grill: Overlooking the marina, this is one of the 100 best al fresco dining experiences in the US.
Chart House: A refined steakhouse with a terrace perched above the Gulf waters.

Neighborhood Video Tours

Queen's Harbor

Grand Bay

Water Club

Promenade

Beachplace

L'Ambiance

Country Club Shores

Bay Isles Harbor

Ready to Tour Longboat Key?

Roger Pettingell knows every building and every canal. Schedule a private boat or home tour today.

Contact Roger Pettingell

Overview for Longboat Key, FL

7,512 people live in Longboat Key, where the median age is 71.5 and the average individual income is $138,251. Data provided by the U.S. Census Bureau.

7,512

Total Population

71.5 years

Median Age

High

Population Density Population Density
This is the number of people per square mile in a neighborhood.

$138,251

Average individual Income

Around Longboat Key, FL

There's plenty to do around Longboat Key, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

8

Car-Dependent

Walking Score

51

Bikeable

Bike Score

Points of Interest

Explore popular things to do in the area, including Albritton Fruit, Colony Flower Shop, and T R L Enterprises.

Name	Category	Distance	Reviews	Ratings by Yelp
Visit the Albritton Fruit page on Yelp Search 4016 Gulf Of Mexico Dr on Google Maps	Dining	0.38 miles	0 reviews	0/5 stars
Visit the Colony Flower Shop page on Yelp Search 1620 Gulf Of Mexico Dr on Google Maps	Dining	3.09 miles	0 reviews	0/5 stars
Visit the T R L Enterprises page on Yelp Search 30 Ave Of The on Google Maps	Shopping	0.4 miles	0 reviews	0/5 stars
Visit the Two Sides of Nature page on Yelp Search 5360 Gulf Of Mexico Dr on Google Maps	Shopping	1.87 miles	0 reviews	0/5 stars
Visit the Le Tennique page on Yelp Search 1620 Gulf Of Mexico Dr on Google Maps	Shopping	3.09 miles	0 reviews	0/5 stars
Visit the Rum International page on Yelp Search 4134 Gulf Of Mexico Dr on Google Maps	Active	0.32 miles	0 reviews	0/5 stars

Demographics and Employment Data for Longboat Key, FL

Population Households Employment

Longboat Key has 4,172 households, with an average household size of 1.8. Data provided by the U.S. Census Bureau. Here’s what the people living in Longboat Key do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 7,512 people call Longboat Key home. The population density is 1,842 and the largest age group is Data provided by the U.S. Census Bureau.

7,512

Total Population

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

71.5 years

Median Age

47 / 53%

Men vs Women

Population by Age Group

0-9:

0-9 Years

10-17:

10-17 Years

18-24:

18-24 Years

25-64:

25-64 Years

65-74:

65-74 Years

75+:

75+ Years

Education Level

Less Than 9th Grade
High School Degree
Associate Degree
Bachelor Degree
Graduate Degree

4,172

Total Households

1.8

Average Household Size

$138,251

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married

Single

Divorced

Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes

15 to 29 Minutes

30 to 59 Minutes

60+ Minutes

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Schools in Longboat Key, FL

All ()

Primary Schools ()

Middle Schools ()

High Schools ()

Mixed Schools ()

The following schools are within or nearby Longboat Key. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.

Type

Name

Featured Properties

For Sale

$6,999,000

1199 WESTWAY DR, SARASOTA, FL 34236
For Sale
$6,995,000

246 MORNINGSIDE DR, SARASOTA, FL 34236
- 4 Beds
- 6 Baths
- 4,617 Sq.Ft.
For Sale
$6,850,000

2116 CASEY KEY RD, NOKOMIS, FL 34275
- 4 Beds
- 4 Baths
- 5,590 Sq.Ft.
For Sale
$4,795,000

2417 CASEY KEY RD, NOKOMIS, FL 34275
- 2 Beds
- 2 Baths
- 1,484 Sq.Ft.
For Sale
$3,895,000

1960 BOYCE ST, SARASOTA, FL 34239
- 4 Beds
- 5 Baths
- 3,674 Sq.Ft.
Pending
$3,499,000

1300 BENJAMIN FRANKLIN DR #908, SARASOTA, FL 34236
- 2 Beds
- 3 Baths
- 3,330 Sq.Ft.
Pending
$3,499,000

7689 COVE TER, SARASOTA, FL 34231
- 4 Beds
- 4 Baths
- 4,564 Sq.Ft.
For Sale
$2,999,000

8250 HUGH ALISON PL, SARASOTA, FL 34240
- 5 Beds
- 5 Baths
- 5,163 Sq.Ft.
For Sale
$2,995,000

340 GULF OF MEXICO DR #136, LONGBOAT KEY, FL 34228
- 3 Beds
- 4 Baths
- 2,880 Sq.Ft.
Active Under Contract
$2,895,000

3548 FAIR OAKS LN, LONGBOAT KEY, FL 34228
- 4 Beds
- 5 Baths
- 3,470 Sq.Ft.
Pending
$2,795,000

705 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
- 4 Beds
- 4 Baths
- 3,083 Sq.Ft.
For Sale
$2,675,000

3530 MISTLETOE LN, LONGBOAT KEY, FL 34228
- 4 Beds
- 4 Baths
- 3,102 Sq.Ft.
Pending
$2,595,000

2410 HARBOURSIDE DR #142, LONGBOAT KEY, FL 34228
- 3 Beds
- 4 Baths
- 3,382 Sq.Ft.
For Sale

$2,295,000

355 S SHORE DR, SARASOTA, FL 34234
For Sale
$1,795,000

6300 MIDNIGHT PASS RD #809, SARASOTA, FL 34242
- 2 Beds
- 2 Baths
- 1,271 Sq.Ft.
For Sale
$1,699,000

3194 CHARLES MACDONALD DR, SARASOTA, FL 34240
- 4 Beds
- 4 Baths
- 3,833 Sq.Ft.
For Sale
$1,695,000

99 SUNSET DR #401, SARASOTA, FL 34236
- 3 Beds
- 3 Baths
- 2,516 Sq.Ft.
For Sale
$1,595,000

2425 GULF OF MEXICO DR #3A, LONGBOAT KEY, FL 34228
- 2 Beds
- 2 Baths
- 1,639 Sq.Ft.
For Sale
$1,175,000

3808 GULF OF MEXICO DR #E412, LONGBOAT KEY, FL 34228
- 3 Beds
- 3 Baths
- 2,544 Sq.Ft.
For Sale
$1,125,000

4525 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228
- 2 Beds
- 2 Baths
- 1,362 Sq.Ft.
For Sale
$1,095,000

1919 LAUREL ST, SARASOTA, FL 34236
- 2 Beds
- 2 Baths
- 1,713 Sq.Ft.
For Sale
$944,000

2098 PALM VIEW RD, SARASOTA, FL 34240
- 4 Beds
- 3 Baths
- 3,732 Sq.Ft.
For Sale
$899,000

1350 SIESTA BAYSIDE DR #1350B, SARASOTA, FL 34242
- 3 Beds
- 2 Baths
- 1,495 Sq.Ft.
For Sale
$899,000

2546 LOMA LINDA ST, SARASOTA, FL 34239
- 3 Beds
- 3 Baths
- 1,779 Sq.Ft.
For Sale
$799,000

5311 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
- 2 Beds
- 2 Baths
- 1,110 Sq.Ft.
For Sale
$799,000

9000 BLIND PASS RD #303, SARASOTA, FL 34242
- 1 Bed
- 2 Baths
- 871 Sq.Ft.
For Sale
$699,000

1328 SIESTA BAYSIDE DR #1328C, SARASOTA, FL 34242
- 2 Beds
- 2 Baths
- 1,280 Sq.Ft.
For Sale
$699,000

800 N TAMIAMI TRL #321, SARASOTA, FL 34236
- 2 Beds
- 2 Baths
- 1,734 Sq.Ft.
For Sale
$329,000

1749 HILLVIEW ST #1, SARASOTA, FL 34239
- 2 Beds
- 1 Bath
- 743 Sq.Ft.
Pending
$309,900

631 N ORANGE AVE #208, SARASOTA, FL 34236
- 2 Beds
- 2 Baths
- 784 Sq.Ft.
For Sale
$299,000

631 N ORANGE AVE #108, SARASOTA, FL 34236
- 2 Beds
- 2 Baths
- 784 Sq.Ft.
For Sale
$150,000

2491 CRISPIN CT #G3, SARASOTA, FL 34235
- 2 Beds
- 2 Baths
- 1,230 Sq.Ft.