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  1. Home
  2. /Longboat Key, FL
  3. /500 - 4995 GULF OF MEXICO DRIVE
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$5,695,000est. $28,797 MortgageInfo icon
Date Listed : Jan 13, 2026 Days on HelloCondo: 183

500- 4995 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228

BEDS

beds

4

BATHS

baths

4

PARKING

parking

-

SQFT

sqft
3344

Description

Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.

Description

Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.
listing image
listing image 2
listing image 3
500 -
$5,695,000
est. $28,797.02 MortgageInfo icon
Date Listed : Jan 13, 2026
Days on HelloCondo: 183

500 -

4995 GULF OF MEXICO DRIVE #500, LONGBOAT KEY, FL 34228

BEDS

4

BATHS

4

PARKING

-

SQFT

3,344

Description

Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.

Description

Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.

Glen Gardens Estate Market Stats Last 12 months

LOCKER
Contact Us for Info

POSSESSION
Contact Us for Info
HOA FEESinfo
Contact Us for Info

OUTDOOR SPACE
Balcony, Cou
TAXES
$47,518.52 (2024)

BUILDING AGE
19 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$1703

Market Stats

HOA FEESinfo
Contact Us for Info

OUTDOOR SPACE
Balcony, Cou
TAXES
$47,518.52 (2024)

BUILDING AGE
19 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$1703

Amenities

Parking
Parking
-
Locker
Locker
Concierge
Concierge
-
Elevator(s)
Elevator(s)
-
Central AC
Central AC
Check Icon
Pool
Pool
Check Icon
Fitness Center
Fitness Center
Check Icon
Visitors Parking
Visitors Parking
-

Amenities

Unit
Parking GarageParking Garage
Building
PoolPool

Policies

Pet Allowed
Check
Pet Allowed Info icon
Check Icon
BBQ Permitted
BBQ Permitted
Sublet Allowed
Sublet Allowed
Short-term Rental Allowed
Short-term Rental Allowed

Unit Price History

DateMLSStatusPrice
Jan 2026MLS#: A4677613Pending$6,495,000
Aug 2019MLS#: A4428638Closed$4,200,000
Feb 2013MLS#: A3950796Closed$3,565,000

Unit Price History

$6,495,000

Pending

Jan 2026MLS#: A4677613

$4,200,000

Closed

Aug 2019MLS#: A4428638

$3,565,000

Closed

Feb 2013MLS#: A3950796

Monthly Payment Calculator

$33,302 / Monthly

All calculations are estimates and provided by HelloCondo.com
for informational purposes only. Actual amounts may vary.

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Monthly Payment Calculator

$33,302
Est.
Listing Price
Down Payment
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Terms
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Down Payment
Interest Rate
Terms
$33,302 / Monthly

All calculations are estimates and provided by HelloCondo.com for informational purposes only. Actual amounts may vary.

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Monthly Mortgage: $28,797
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The Neighborhood: LONGBOAT KEY, FL

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  1. Home
  2. /Longboat Key, FL
  3. /500 - 4995 GULF OF MEXICO DRIVE
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