Condos for Sale in Longboat Key, FL

40 of 48 results

3806 GULF OF MEXICO DRIVE UNIT C208, LONGBOAT KEY, FL 34228
Active
$295,000
Condo
1 bd • 1 ba • 712 sq ft
3806 GULF OF MEXICO DRIVE UNIT C208, LONGBOAT KEY, FL 34228
SLIPSTREAM
4310 FALMOUTH DRIVE UNIT 105, LONGBOAT KEY, FL 34228
Active
$399,900
Condo
1 bd • 1 ba • 747 sq ft
4310 FALMOUTH DRIVE UNIT 105, LONGBOAT KEY, FL 34228
SLIPSTREAM
4473 GULF OF MEXICO DRIVE UNIT 4473, LONGBOAT KEY, FL 34228
Active
$10,900,000
Condo
8 bd • 8 ba • 7,474 sq ft
4473 GULF OF MEXICO DRIVE UNIT 4473, LONGBOAT KEY, FL 34228
SLIPSTREAM
4430 EXETER DRIVE UNIT M108, LONGBOAT KEY, FL 34228
Active
$649,900
Condo
2 bd • 2 ba • 1,376 sq ft
4430 EXETER DRIVE UNIT M108, LONGBOAT KEY, FL 34228
SLIPSTREAM
4430 EXETER DRIVE UNIT 106, LONGBOAT KEY, FL 34228
Active
$695,000
Condo
2 bd • 2 ba • 1,152 sq ft
4430 EXETER DRIVE UNIT 106, LONGBOAT KEY, FL 34228
SLIPSTREAM
4235 GULF OF MEXICO DRIVE UNIT T101, LONGBOAT KEY, FL 34228
Active
$825,000
Condo
1 bd • 1 ba • 839 sq ft
4235 GULF OF MEXICO DRIVE UNIT T101, LONGBOAT KEY, FL 34228
SLIPSTREAM
4127 GULF OF MEXICO DRIVE UNIT N102, LONGBOAT KEY, FL 34228
Active
$4,900,000
Condo
3 bd • 4 ba • 3,521 sq ft
4127 GULF OF MEXICO DRIVE UNIT N102, LONGBOAT KEY, FL 34228
SLIPSTREAM
4234 GULF OF MEXICO DRIVE UNIT U1, LONGBOAT KEY, FL 34228
Active
$625,000
Condo
2 bd • 2 ba • 1,248 sq ft
4234 GULF OF MEXICO DRIVE UNIT U1, LONGBOAT KEY, FL 34228
SLIPSTREAM
750 BAYPORT WAY UNIT 750, LONGBOAT KEY, FL 34228
Active
$850,000
Condo
2 bd • 2 ba • 1,570 sq ft
750 BAYPORT WAY UNIT 750, LONGBOAT KEY, FL 34228
SLIPSTREAM
4311 GULF OF MEXICO DRIVE UNIT 501, LONGBOAT KEY, FL 34228
Active
$1,095,000
Condo
2 bd • 2 ba • 1,585 sq ft
4311 GULF OF MEXICO DRIVE UNIT 501, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$995,000
Condo
2 bd • 2 ba • 1,574 sq ft
4401 GULF OF MEXICO DRIVE UNIT 601, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$850,000
Condo
2 bd • 2 ba • 1,641 sq ft
815 BAYPORT WAY UNIT 815, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$389,000
Condo
2 bd • 2 ba • 1,046 sq ft
3806 GULF OF MEXICO DRIVE UNIT C310, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$545,000
Condo
2 bd • 2 ba • 1,144 sq ft
600 SUTTON PLACE UNIT 104B, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$397,000
Condo
2 bd • 2 ba • 1,133 sq ft
3804 GULF OF MEXICO DRIVE UNIT B207, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$485,000
Condo
2 bd • 2 ba • 1,144 sq ft
605 SUTTON PLACE UNIT 102, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$675,000
Condo
2 bd • 2 ba • 1,570 sq ft
842 BAYPORT WAY UNIT 842, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$338,900
Condo
1 bd • 1 ba • 747 sq ft
4360 CHATHAM DRIVE UNIT 305, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$445,000
Condo
2 bd • 2 ba • 1,007 sq ft
3804 GULF OF MEXICO DRIVE UNIT B305, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$999,000
Condo
2 bd • 2 ba • 1,456 sq ft
4325 GULF OF MEXICO DRIVE UNIT 305, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$340,000
Condo
1 bd • 1 ba • 837 sq ft
4390 EXETER DRIVE UNIT 305, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$625,000
Condo
2 bd • 2 ba • 1,152 sq ft
4420 EXETER DRIVE UNIT 303, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$470,000
Condo
2 bd • 2 ba • 1,072 sq ft
4370 CHATHAM DRIVE UNIT 104, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$525,000
Condo
2 bd • 2 ba • 1,072 sq ft
4320 FALMOUTH DRIVE UNIT 103, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$649,000
Condo
2 bd • 2 ba • 1,376 sq ft
4440 EXETER DRIVE UNIT 106, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$585,000
Condo
2 bd • 2 ba • 1,376 sq ft
4440 EXETER DRIVE UNIT 301, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$949,000
Condo
2 bd • 2 ba • 1,570 sq ft
806 BAYPORT WAY UNIT 806, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$1,095,000
Condo
2 bd • 2 ba • 1,250 sq ft
4485 GULF OF MEXICO DRIVE UNIT 804, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$530,000
Condo
2 bd • 2 ba • 1,072 sq ft
4340 FALMOUTH DRIVE UNIT D104, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$499,000
Condo
2 bd • 2 ba • 1,152 sq ft
4380 EXETER DRIVE UNIT H202, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$649,900
Condo
2 bd • 2 ba • 1,072 sq ft
4310 FALMOUTH DRIVE UNIT 102, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$675,000
Condo
2 bd • 2 ba • 1,316 sq ft
4350 CHATHAM DRIVE Unit E-208, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$619,000
Condo
2 bd • 2 ba • 1,304 sq ft
605 SUTTON PLACE UNIT 201, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$475,000
Condo
2 bd • 2 ba • 1,132 sq ft
600 SUTTON PLACE UNIT B302, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$529,000
Condo
2 bd • 2 ba • 1,152 sq ft
4390 EXETER DRIVE UNIT 206, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$595,000
Condo
2 bd • 2 ba • 1,346 sq ft
4234 GULF OF MEXICO DRIVE UNIT D1, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$648,800
Condo
2 bd • 2 ba • 1,248 sq ft
4234 GULF OF MEXICO DRIVE UNIT Q2, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$849,000
Condo
3 bd • 2 ba • 1,794 sq ft
4234 GULF OF MEXICO DRIVE UNIT G2, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$399,000
Condo
2 bd • 2 ba • 1,007 sq ft
3802 GULF OF MEXICO DRIVE UNIT A203, LONGBOAT KEY, FL 34228
SLIPSTREAM
Active
$399,000
Condo
2 bd • 2 ba • 1,072 sq ft
4350 CHATHAM DRIVE UNIT 106, LONGBOAT KEY, FL 34228
SLIPSTREAM
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Longboat Key, FL Market Summary

Current MLS market statistics for active listings in this area.

Active listings50
New listings last 30 days9
Median list price$622,000
Median price per sq ft$519
List price range$295,000 - $10,900,000
Median bedrooms2
Median bathrooms2
Median living area1,151 sq ft
Typical HOA fees$917 – $1,978 / month

Medians are based on 50 sampled active listings when available.

Longboat Key has a distinctly structured condo market defined by low-density development, a quiet residential environment, and a strong concentration of waterfront properties. Stretching approximately 12 miles along the Gulf Coast, the island maintains a controlled development pattern that directly limits supply and shapes long-term property values.

Longboat Key Condo Market Overview

The condo market on Longboat Key is built around waterfront positioning and building quality, with inventory concentrated in established developments along both the Gulf of Mexico and Sarasota Bay.

Typical price ranges:

  • Entry-level condos (older buildings or limited views): $400,000 – $800,000
  • Mid-range condos (updated units or partial water views): $800,000 – $1.8M
  • Gulf-front and bayfront condos: $1.8M – $4M+
  • Luxury residences and newer developments: $4M+

Pricing is driven primarily by direct water exposure, building upgrades, and overall development quality, with Gulf-front units consistently commanding the highest premiums.

Low-Density Development and Supply Constraints

One of the defining features of Longboat Key is its controlled development pattern.

  • The island avoids overdevelopment and large-scale commercial expansion
  • Residential communities are spaced out along a linear coastal layout
  • New construction opportunities are limited due to land constraints

This creates a more stable, supply-limited condo market compared to nearby areas.

Property Types in Longboat Key Condos

Condo inventory reflects decades of development across the island.

  • Mid-rise and high-rise condominium buildings
  • Gulf-front developments along the western shoreline
  • Bayfront and canal-front communities along Sarasota Bay
  • Gated and managed residential complexes

Many buildings were developed in earlier cycles, resulting in a mix of original units and fully renovated properties within the same communities.

Rental Restrictions and Ownership Profile

Longboat Key differs from nearby barrier islands in how rental policies are structured.

  • Many condo buildings enforce minimum rental periods (monthly or longer)
  • Fewer properties allow high-frequency short-term rentals
  • Rental rules vary by building and HOA

This shifts the market toward:

  • Second-home buyers
  • Seasonal residents
  • Long-term ownership rather than short-term investment

HOA Fees on Longboat Key Condos

HOA costs are a central part of ownership and vary based on building size, services, and location.

Typical ranges:

  • Older or smaller buildings: $600 – $1,000/month
  • Mid-range condo communities: $1,000 – $1,800/month
  • Luxury and full-service buildings: $1,800 – $3,500+/month

HOA fees typically include:

  • Exterior and structural maintenance
  • Shared amenities such as pools and fitness centers
  • Building operations and management
  • Insurance components for coastal properties
  • Water, trash, and common services

Higher-end developments often include more comprehensive services and amenities.

What Defines Condo Living on Longboat Key

Longboat Key offers a quieter and more controlled coastal environment compared to nearby islands.

  • Lower overall density and reduced congestion
  • Strong emphasis on residential use rather than tourism
  • Direct access to Gulf beaches and Sarasota Bay
  • Preserved natural areas and waterfront landscapes
  • A more private, less commercialized setting

The environment supports a lifestyle focused on relaxation, space, and long-term use, rather than short-term activity.

Natural Environment and Its Impact on Demand

Longboat Key’s preserved environment plays a direct role in its real estate appeal.

  • Access to natural areas such as Greer Island (Beer Can Island) and coastal preserves
  • Walking trails and waterfront boardwalks within protected park areas
  • Regular visibility of wildlife, including dolphins and coastal bird species
  • Mangrove and bay ecosystems supporting outdoor recreation

These factors contribute to a market that appeals to buyers prioritizing environment, privacy, and outdoor access over density or nightlife.

Accessibility and Location

Longboat Key is positioned between two major coastal hubs while maintaining separation.

  • Southern access toward Sarasota and St. Armands Circle
  • Northern access toward Bradenton and Anna Maria Island
  • Bridge connections providing access without high-density traffic patterns

This allows residents to access amenities while maintaining a more residential atmosphere.

What Drives Demand for Longboat Key Condos

  • Direct Gulf and bayfront access
  • Low-density, controlled development environment
  • Strong appeal to second-home and retirement buyers
  • Limited new supply due to land constraints
  • Preference for quieter coastal living

Demand tends to be more stable and less dependent on short-term rental cycles.

Key Condo Areas on Longboat Key

  • Gulf-front developments along Gulf of Mexico Drive
  • Bayfront communities along Sarasota Bay
  • Mid-island residential condo clusters
  • Gated and resort-style communities

What You Get with Longboat Key Condos

  • Waterfront-focused condo living
  • Access to beaches without heavy tourist density
  • Condo ownership within a more private residential environment
  • Strong long-term appeal tied to location and limited supply

What to Expect When Buying on Longboat Key

  • Significant variation between older buildings and renovated units
  • HOA fees as a major component of ownership cost
  • Rental restrictions that vary by community
  • Premium pricing for Gulf-front and updated properties
  • Lower turnover compared to more active markets

Who Longboat Key Condos Fit Best

  • Buyers looking for second homes or seasonal residences
  • Buyers prioritizing privacy and quieter environments
  • Buyers less focused on short-term rental income
  • Buyers comfortable with HOA-based ownership

How to Decide if a Longboat Key Condo Is Right for You

Longboat Key condos work best when your priority is waterfront living, privacy, and long-term use.

They are a strong fit if:

  • You want a quieter barrier island environment
  • You prioritize waterfront access without heavy tourist activity
  • You are comfortable with rental restrictions in some buildings
  • You value long-term ownership over short-term income