Longboat Key

Longboat Key

Geography

Longboat Key is located North of St. Armand’s Key and South of Bradenton Beach, Holmes Beach, and Anna Maria Island. This 11 mile expanse includes both Sarasota and Manatee counties. The Gulf of Mexico Drive runs the length of the island and branches off to residential neighborhoods and streets. From some locations, one can see both Sarasota Bay and the Gulf of Mexico.

Attractions

The greatest attraction of Longboat Key is its private, quiet and peaceful waterside living. Imagine your own sequestered oasis: white sandy beaches offered only to residents and renting guests of Longboat Key. Those who live on Longboat Key generally prefer a laidback lifestyle that may include fishing, boating and enjoying…
[read more=”more” less=”less”]excellent dining. Dining options cater to any palate. Whether you are looking to enjoy a cheeseburger and a beer, cracking stone crabs, or getting outfitted impressively for an evening of fine dining, Longboat Key has your perfect restaurant.

There are just enough conveniences, including grocery stores, banks and dry cleaners to allow you to never leave the confines of this paradise, but not so much activity that the tranquility of the island is disturbed. Should you choose to explore off the island, the surrounding cities of Sarasota and Bradenton provide Longboat Key with a vast and varied list of amenities.[/read]

Real Estate

Almost the entire land area of Longboat Key is now occupied by either single-family homes or condominiums. Most of the condominium communities offer pools, tennis courts, water views and beach accesses. Many of the individually owned homes are as many as 45 years old, annexed to comparatively small parcels. Over…
[read more=”more” less=”less”]the past few years, many of these homes have been purchased, demolished and rebuilt by new owners who have replaced the aged residence with ornate homes. These homes have been constructed to remain for years to come while preserving the imperturbable lifestyle on Longboat Key. Ready to find for your private peace of paradise?[/read]

LISTING INVENTORY

UNITS
Average Residential price $1,222,291 Based on 209 Residential listings.
Priced from $79,900 to $14,500,000.
Luxury Homes 71 Homes listed over $1M
New in the last 30 days 63 +30% over prev 30 days

    FULL LISTING6171 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1508

    Under Construction. Gulf front Estate under construction directly on the beach with 100 feet of Gulf frontage. The home exhibits the latest in modern architectural design....

    4
    6
    7,352
    $14,500,000

    FULL LISTING5541 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1903

    Enjoy the easy lifestyle of this home with awe-inspiring views overlooking the wide waters of Gulf of Mexico. A Rare Find and a must see Beachfront Luxury three story, 5...

    11
    14
    14,005
    $8,000,000

    FULL LISTING612 JUAN ANASCO DRIVE
    Longboat Key, Florida FL 34228-1425

    This exquisite property is a stunning Bayfront estate with over 600 feet of Bayfront with captivating panoramic views of Sarasota Bay, the intracoastal waterway and...

    6
    8
    8,976
    $7,800,000

    FULL LISTING1620 GULF OF MEXICO DRIVE605
    Longboat Key, Florida FL 34228-3403

    Pre-Construction. To be built. This 4-bedroom corner PENTHOUSE offers a wonderful opportunity to be above it all at the new St. Regis Resort and Spa. Beautifully appointed...

    4
    5
    4,017
    $6,970,000

    FULL LISTING771 OLD COMPASS ROAD
    Longboat Key, Florida FL 34228-1647

    Exceptional direct Bayfront custom Key West style home has spectacular water views plus extraordinary designer details.This magnificent Bayfront home was upgraded in...

    4
    6
    5,259
    $6,950,000

    FULL LISTING4651 GULF OF MEXICO DRIVEPH A
    Longboat Key, Florida FL 34228-2101

    Pre-Construction. To be built. Nestled within more than 3 acres of Longboat Key’s pristine landscape, Sage Longboat Key Residences is an incredible oasis of new...

    4
    5
    4,000
    $6,240,000

    FULL LISTING4651 GULF OF MEXICO DRIVE3 C
    Longboat Key, Florida FL 34228-2101

    Pre-Construction. To be built. Nestled within more than 3 acres of Longboat Key’s pristine landscape, Sage Longboat Key Residences is an incredible oasis of new...

    4
    5
    4,100
    $5,260,000

    FULL LISTING4651 GULF OF MEXICO DRIVE2B
    Longboat Key, Florida FL 34228-2101

    Pre-Construction. To be built. Nestled within more than 3 acres of Longboat Key’s pristine landscape, Sage Longboat Key Residences is an incredible oasis of new...

    4
    5
    3,900
    $4,845,000

    FULL LISTING4651 GULF OF MEXICO DRIVE1 D
    Longboat Key, Florida FL 34228-2101

    Pre-Construction. To be built. Nestled within more than 3 acres of Longboat Key’s pristine landscape, Sage Longboat Key Residences is an incredible oasis of new...

    4
    5
    3,900
    $4,380,000

    FULL LISTING2333 GULF OF MEXICO DRIVE1C4
    Longboat Key, Florida FL 34228-3262

    Bask in the endless glowing sunsets only the Gulf Coast of Florida can offer. This exquisite, custom designed beachfront condominium features direct views of the Gulf of...

    4
    5
    3,540
    $3,999,000

    FULL LISTING5861 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1701

    Direct Gulf front estate lot for building your dream home right on the beach! The site is 100 feet on the beach and approximately 500 feet deep. This parcel is cleared...

    $3,950,000

    FULL LISTING1620 GULF OF MEXICO DRIVE411
    Longboat Key, Florida FL 34228

    Pre-Construction. To be built. Very spacious 2 -bedroom corner residence offers wrap around floor to ceiling windows and doors in the Gathering Room with a fabulous wet...

    2
    3
    3,130
    $3,920,000

    FULL LISTING35 LIGHTHOUSE POINT DRIVE
    Longboat Key, Florida FL 34228-3918

    This casually elegant custom designed residence by DSDG Architects is in the exclusive gated Lighthouse Point waterfront enclave of just 16 custom residences at the...

    4
    5
    4,430
    $3,875,000

    FULL LISTING5005 GULF OF MEXICO DRIVE8
    Longboat Key, Florida FL 34228-2090

    BONAIRE, AN EXCLUSIVE GULF SIDE COMMUNITY, WHICH HAS 9 CUSTOM HOMES AND A PRIVATE COMMUNITY BEACH ACCESS. THIS EXTRAORDINARY HOME IS DESIGNED IN THE TRADITIONAL BRITISH...

    5
    6
    4,115
    $3,788,000

    FULL LISTING6603 GULFSIDE ROAD
    Longboat Key, Florida FL 34228-1416

    A rare, quintessential beach house on 100 feet of powdery white quartz sand and the crystal clear waters of the Gulf of Mexico. By far the prettiest 20,430 sq. ft....

    3
    3
    3,051
    $3,750,000

    FULL LISTING5005 GULF OF MEXICO DRIVE5
    Longboat Key, Florida FL 34228-2090

    Extraordinary property in the beautiful, exclusive Gulf side community of Bonaire. Brand new British West Indies home is only steps away from a private beach access and...

    4
    5
    3,595
    $3,650,000

    FULL LISTING8 WINSLOW PLACE
    Longboat Key, Florida FL 34228-2919

    Spectacular waterfront home located on a protected bayou in a private, lush setting with great boating water. The dock will accommodate multiple water crafts and the...

    3
    4
    4,169
    $3,345,000

    FULL LISTING6489 GULFSIDE ROAD
    Longboat Key, Florida FL 34228

    GULF FRONT; GULF FRONT ; GULF FRONT-Prime Gulf Front Property for sale. Location ,Location, Location!!! 0,63 acre of Gulf Front property enjoying almost 100 feet of Gulf...

    $3,250,000

    FULL LISTING1511 GULF OF MEXICO DRIVE202
    Longboat Key, Florida FL 34228-3429

    Positioned on the second floor, overlooking the Gulf of Mexico azure horizon, this beachfront treasure presents upscale class with relaxed coastal style. The perfect...

    3
    4
    2,940
    $3,200,000

    FULL LISTING1241 GULF OF MEXICO DRIVE701
    Longboat Key, Florida FL 34228-4623

    “Shelter-in-Paradise” from this sought-after DIRECT Gulf front location on the 7th floor at the coveted Water Club on Longboat Key. Be “Wowed” by mesmerizing Gulf,...

    3
    5
    3,400
    $3,195,000

    FULL LISTING1281 GULF OF MEXICO DRIVEPH1108
    Longboat Key, Florida FL 34228-4629

    VIEWS BEYOND YOUR EXPECTATIONS! Unobstructed direct Gulf, Bay & City views from this spectacular 3 bedroom Gulf-to-Bay penthouse residence. The unparalleled, panoramic...

    3
    5
    3,273
    $3,175,000

    FULL LISTING6321 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1512

    Welcome to the lowest-priced, single family, Gulf-front property for sale on Longboat Key, offering extraordinary potential for a discriminating buyer, whose imagination...

    $2,700,000

    FULL LISTING435 L AMBIANCE DRIVEK605
    Longboat Key, Florida FL 34228-3927

    The luxurious L’Ambiance lifestyle is a sought-after, resort-style experience that wonderfully complements this sixth-floor residence.

    2
    3
    2,820
    $2,699,000

    FULL LISTING541 HARBOR POINT ROAD
    Longboat Key, Florida FL 34228-3503

    A boater’s dream, this private waterfront residence is wonderfully placed with views of Sarasota Bay as the picture-perfect backdrop. Set among the coastal landscape of...

    4
    7
    5,114
    $2,695,000

    FULL LISTING545 SANCTUARY DRIVEB705
    Longboat Key, Florida FL 34228-3847

    Rarely for sale, this high-floor Sanctuary 3-BR, 3-Bath condo with perfect east/west views offers total privacy. Relax, unwind, and enjoy the magnificent views of the...

    3
    3
    2,580
    $2,690,000

    FULL LISTING435 L AMBIANCE DRIVEK405
    Longboat Key, Florida FL 34228-3927

    Ready to escape to the sandy beaches of Longboat Key and experience a property that elevates gracious, luxurious living to a new level? L ‘Ambiance, a highly sought...

    2
    3
    2,820
    $2,599,000

    FULL LISTING524 SCHOONER LANE
    Longboat Key, Florida FL 34228-3728

    Enjoy the highest quality construction in this 4,438ft 4BR, 4-1/2BA custom Country Club Shores home built in 2008 on an oversized waterfront lot. A masterpiece of poise...

    4
    5
    4,438
    $2,499,999

    FULL LISTING672 DREAM ISLAND ROAD
    Longboat Key, Florida FL 34228-1503

    Canal front custom home built in 2014 on a half acre lot. There is 400 sq. ft. of dock with a 16,000 lb. boat lift and the boater enjoys direct access to the inter coastal...

    4
    4
    2,712
    $2,395,000

    FULL LISTING535 SANCTUARY DRIVEC107
    Longboat Key, Florida FL 34228-3836

    The tropical splendor of a beachfront lifestyle meets the ease and convenience of maintenance-free living in this spacious, fully furnished 3BR walk-down residence in the...

    3
    3
    2,580
    $2,300,000

    FULL LISTING581 WEDGE LANE
    Longboat Key, Florida FL 34228-3525

    One or more photo(s) has been virtually staged. EXQUISITE NEW CONSTRUCTION HOME IN COUNTRY CLUB SHORES WITH FULL BAY VIEWS!!! Stunning home on one of the best lots in...

    3
    4
    3,127
    $2,299,000

    FULL LISTING560 HORNBLOWER LANE
    Longboat Key, Florida FL 34228-3718

    Big water views and southern exposure abounds! On an oversized lot, only two homes in from Sarasota Bay, this beautiful John Cannon home in Country Club Shores is in ideal...

    4
    5
    4,206
    $2,295,000

    FULL LISTING3381 BAYOU SOUND
    Longboat Key, Florida FL 34228-3001

    Casual elegance at its best, this modern masterpiece showcases an unprecedented collaboration between the architect and designer and landscape and lighting specialists....

    4
    4
    3,363
    $2,195,000

    FULL LISTING415 L AMBIANCE DRIVEE707
    Longboat Key, Florida FL 34228-3908

    Spectacular Gulf, bay and city views are the highlight as soon as you enter this beautifully updated seventh floor L’Ambiance residence. Nearly every inch of this...

    2
    3
    2,460
    $2,195,000

    FULL LISTING612 RANGER LANE
    Longboat Key, Florida FL 34228-3726

    Poised on a saltwater canal only four homes in from Sarasota Bay, this stunning two-story John Cannon built home makes a bold impression, inside and out. Beautiful palm...

    5
    4
    4,030
    $2,100,000

    FULL LISTING210 SANDS POINT ROAD2807
    Longboat Key, Florida FL 34228-3960

    One-of-a-kind deluxe residence expertly renovated to perfection offering panoramic views from the Gulf of Mexico to the downtown city skyline perched atop Sarasota Bay....

    2
    2
    1,700
    $1,990,000

    FULL LISTING771 EMERALD HARBOR DRIVE
    Longboat Key, Florida FL 34228-1609

    Make your Clients Dream Come True with this Gorgeous Resort Style Bay Front home!! New Agent - New Home - Priced to Sell and Completing Update to a 4 Bedroom with Fire...

    4
    3
    3,750
    $1,899,000

    FULL LISTING5630 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228

    The best, and perhaps the only, large parcel of land on the bay side of Gulf of Mexico Dr. Currently zoned C1 BUT by referendum the commission approved the request for the...

    $1,850,000

    FULL LISTING501 GUNWALE LANE
    Longboat Key, Florida FL 34228-3709

    BRAND NEW construction in south Longboat's Country Club Shores! Hard to find anything new on the water for this price! Just completed, this stunning West Indies home is...

    3
    3
    2,523
    $1,799,000

    FULL LISTING680 NEPTUNE AVENUE
    Longboat Key, Florida FL 34228-2916

    IDYLLIC ISLAND LIFESTYLE ON LONGBOAT KEY – Incorporating the finest brands in luxury, this coastal inspired design was constructed in 2014 by TODD JOHNSTON, a legend in...

    4
    5
    3,245
    $1,795,000

    FULL LISTING760 MARBURY LANE
    Longboat Key, Florida FL 34228-1442

    Sleepy Lagoon has long been home to many of the finest residences on the amazing barrier island and this custom estate built in 2012 is a shining example. Situated on a...

    4
    3
    2,611
    $1,750,000

    FULL LISTING501 CUTTER LANE
    Longboat Key, Florida FL 34228-3705

    "Under the Tuscan Sun " is the feeling emanating in describing this magnificent Mediterranean Villa situated here on beautiful Longboat Key. This masonry custom home has...

    4
    4
    3,536
    $1,739,000

    FULL LISTING5870 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1702

    Waterfront charm nestled on nearly .60 acres on Gulf of Mexico Drive. This is a unique home built at a time when Longboat Key was just incorporated in the mid 1950's. ...

    4
    4
    2,316
    $1,699,000

    FULL LISTING1485 GULF OF MEXICO DRIVEA503
    Longboat Key, Florida FL 34228

    See and hear the Gulf of Mexico from every room in this penthouse condo at Player’s Club. Totally renovated to the studs using only the finest materials, creating a...

    3
    3
    2,200
    $1,699,000

    FULL LISTING6809 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1305

    Beach Walk, a small Gulf front development with big square footage on northern Longboat Key. Complete interior remodel in 2016, including new exterior Hardy Board for the...

    3
    3
    2,496
    $1,695,000

    FULL LISTING560 OUTRIGGER LANE
    Longboat Key, Florida FL 34228-3722

    This remodeled Country Club Shores home is situated in the perfect location on the canal. Located only three lots in from the open water this home features stunning views...

    3
    4
    2,917
    $1,560,000

    FULL LISTING5650 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1906

    A rare opportunity to own a parcel of prime commercial property on Gulf of Mexico Drive. The property already has a 2000 Sq.Ft. commercial building in pristine condition...

    2,009
    $1,495,000

    FULL LISTING3040 GRAND BAY BOULEVARD211
    Longboat Key, Florida FL 34228-4199

    Unparalled panoramic views of Sarasota Bay take center stage as you take an elevator to the inviting foyer of this stunning corner residence. Twinkling city skyline, lush...

    3
    4
    2,925
    $1,495,000

    FULL LISTING5809 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1701

    Gulf-front lot ready to build upon! Enjoy this ideal setting that offers Gulf-front living and a wonderful place to build your dream home. This location is just steps away...

    $1,450,000

    FULL LISTING525 RECLINATA DRIVE
    Longboat Key, Florida FL 34228-1308

    Elegant expression of contemporary style on Longboat Key with deeded beach and bay access.

    4
    4
    3,182
    $1,449,000

    FULL LISTING3452 MISTLETOE LANE
    Longboat Key, Florida FL 34228-4147

    ONLY FULLY WALLED LANAI BETWEEN UNITS & OVERSIZED DECK AREA TOO!!! Beautiful 2 story home with direct bay front & views of Sarasota Bay in Corey's Landing with Private...

    3
    4
    2,810
    $1,399,500

    FULL LISTING3527 FAIR OAKS LANE
    Longboat Key, Florida FL 34228-4121

    An undeniable introduction to quality and distinctive updates will leave a lasting impression in your mind as you embark on a memorable tour of this custom 2-story home...

    4
    5
    4,154
    $1,399,000

    FULL LISTING548 CUTTER LANE
    Longboat Key, Florida FL 34228-3706

    Sarasota has just been named the #1 city to retire to. Make your purchase now before prices increase any further. This is a completely remodeled home on a canal in the...

    3
    3
    1,907
    $1,379,000

    FULL LISTING4239 GULF OF MEXICO DRIVEMH2
    Longboat Key, Florida FL 34228-2424

    Turnkey furnished and immediately ready to move right into, this coastal contemporary beach home is a tropical treat! This completely renovated single-family beach getaway...

    3
    3
    1,350
    $1,350,000

    FULL LISTING3030 GRAND BAY BOULEVARD326
    Longboat Key, Florida FL 34228-4407

    Antigua residences (one of the largest floor plans in the community) do not come on the market often in the sought-after Grand Bay neighborhood. The breathtaking direct...

    3
    4
    2,925
    $1,350,000

    FULL LISTING569 KINGFISHER LANE
    Longboat Key, Florida FL 34228-2611

    Come live the dream in this beautifully renovated, open concept Beach to Bay home on Longboat Key! Homes in Longboat Key Estates rarely come up for sale, this is a unique...

    4
    2
    2,809
    $1,339,995

    FULL LISTING3060 GRAND BAY BOULEVARD142
    Longboat Key, Florida FL 34228-4178

    Waterfront living behind the gates of the Longboat Key Club! Wake to amazing sunrises with beams of light glistening across the waters of Sarasota Bay and end the day...

    3
    4
    2,250
    $1,325,000

    FULL LISTINGLONGBOAT KEY
    Florida Fl 34228-3508

    3 Bedroom canal-front home ready for move in. This home has the best location for natural daylight all day long. This split plan home is ideal for the family who...

    3
    2
    2,308
    $1,300,000

    FULL LISTING3060 GRAND BAY BOULEVARD124
    Longboat Key, Florida FL 34228-4177

    COMPLETELY RENOVATED! The stylish, custom upgrades offered throughout this gorgeous Grand Bay residence will mesmerize you as soon as you enter. Immediately fall in love...

    2
    3
    2,550
    $1,295,000

    FULL LISTING601 LONGBOAT CLUB ROAD101S
    Longboat Key, Florida FL 34228-3806

    Walk-out, three-bedroom beach residences don’t come on the market often at Longboat Key Towers! A flourish of direct breathtaking sunset and panoramic beach views from...

    3
    3
    2,420
    $1,295,000

    FULL LISTING792 SAINT JUDES DRIVE N
    Longboat Key, Florida FL 34228-1814

    Location! Location! Location! Don’t miss out on this rare opportunity to own a spectacular build ready waterfront end lot with 125’ of direct waterfront access. ...

    $1,275,000

    FULL LISTING7149 LA LENAIRE DRIVE
    Longboat Key, Florida FL 34228

    short stories:....It really is a paradise"..like a nature preserve with abundant plant and wildlife...local lore of jewfish island has hidden treasure of it's own once a...

    $1,271,490

    FULL LISTING2165 GULF OF MEXICO DRIVE122
    Longboat Key, Florida FL 34228-3260

    Nowhere is the Elegance and Distinction of the Florida Waterfront Lifestyle more present than in the town of Longboat Key, a coveted and exclusive island brimming with...

    3
    3
    2,448
    $1,250,000

    FULL LISTING636 DREAM ISLAND ROAD
    Longboat Key, Florida FL 34228-1503

    Wide canal location with Southern exposure. Opportunity to have your boat and other water toys docked in your backyard with deep water direct access to the intra coastal...

    4
    2
    2,624
    $1,225,000

    FULL LISTING5461 GULF OF MEXICO DRIVE201
    Longboat Key, Florida FL 34228-1922

    Longboat Cove is poised on the serene waters of Gulf of Mexico. This true three bedroom unit includes eat-in kitchen, full Gulf views from the privacy of your lanai and...

    3
    2
    1,721
    $1,200,000

    FULL LISTING455 LONGBOAT CLUB ROAD301
    Longboat Key, Florida FL 34228

    Step into your own 5 star resort. Unparalleled value and luxury in this open corner residence featuring two decks to enjoy your ocean and golf views. This light filled...

    3
    4
    2,780
    $1,199,000

    FULL LISTING3305 SABAL COVE CIRCLE
    Longboat Key, Florida FL 34228-4153

    One or more photo(s) has been virtually staged. An idyllic mid-key location provides the perfect blend of ambiance and convenience to a world of local attractions for this...

    3
    4
    2,881
    $1,199,000

    FULL LISTING3559 FAIR OAKS LANE
    Longboat Key, Florida FL 34228-4121

    The appeal of moving right in to enjoy this updated Queens Harbour home will immediately impress you. Set among lush greenery, this beautiful three-bedroom plus den...

    3
    4
    3,251
    $1,195,000

    FULL LISTING6320 GULF OF MEXICO DRIVE
    Longboat Key, Florida FL 34228-1513

    Opportunity to own a wonderful three bedroom home across from the beach and gorgeous Gulf water with a deeded dock with a lift. The Bay water is direct access to the...

    3
    4
    2,583
    $1,195,000

    FULL LISTING7149 LONGBOAT DRIVE N
    Longboat Key, Florida FL 34228-1047

    The coastal contemporary transformations adorning the exterior and interior of this cozy waterfront home will immediately draw you in and make it hard to ever leave....

    3
    3
    2,616
    $1,195,000

    FULL LISTING541 CHIPPING LANE
    Longboat Key, Florida FL 34228-3517

    Updated to perfection! Charming sailboat waterfront home in Country Club Shores, close to the point on south Longboat Key. No Bridges to Bay to or the Gulf of Mexico!...

    3
    2
    2,036
    $1,195,000

    FULL LISTING4239 GULF OF MEXICO DRIVEMH4
    Longboat Key, Florida FL 34228-2424

    Welcome to this exclusive move in ready beach oasis located in the highly sought after Pelican Harbour & Beach Club, a secluded Gulf-side cul-de-sac made up of only 5...

    3
    2
    1,549
    $1,195,000

    FULL LISTING340 GULF OF MEXICO DRIVE114
    Longboat Key, Florida FL 34228-4028

    Beautifully Remodeled and Updated 3 BR, 2 BA, 2-Car Garage Furnished (some exceptions) End Unit with Full Sarasota Bay views is located in Desirable Tangerine Bay on the...

    3
    3
    2,394
    $1,190,000

    FULL LISTING1955 GULF OF MEXICO DRIVEG6-411
    Longboat Key, Florida FL 34228-3346

    Beyond compare, this gorgeous move-in ready top-floor condominium, on the southern point of Longboat Key fulfills your greatest island dreams. Higher ceilings and...

    2
    2
    1,492
    $1,175,000

    FULL LISTING573 JUAN ANASCO DRIVE
    Longboat Key, Florida FL 34228-1422

    This beautiful mediterranean style home is located at the opening of the canal offering waterfront living with partial bay view! Bright open floor plan is flanked with...

    5
    4
    3,027
    $1,149,000

    FULL LISTING3030 GRAND BAY BOULEVARD324
    Longboat Key, Florida FL 34228-4407

    This charming, direct bayfront Cayman residence at Grand Bay offers a bright and open living space that is arranged to ideally frame stunning vistas of Sarasota Bay,...

    3
    4
    2,550
    $1,095,000

    FULL LISTING3030 GRAND BAY BOULEVARD393
    Longboat Key, Florida FL 34228-4407

    The spectacular, ninth-floor views of Harbourside Moorings Marina, golf course, Sarasota Bay, downtown and the Gulf of Mexico that welcome you to this Grand Bay Cayman...

    2
    4
    2,550
    $1,095,000

    FULL LISTING383 FIREHOUSE LANE
    Longboat Key, Florida FL 34228-1172

    Bring the most Discerning Buyer to this Contemporary, chic, maintenance-free and impeccably furnished beach house in the Boutique Enclave of Conrad Beach on Longboat Key....

    2
    2
    2,117
    $1,050,000

    FULL LISTING5005 GULF OF MEXICO DRIVE7
    Longboat Key, Florida FL 34228-2090

    Great opportunity to purchase a buildable lot west of gulf on Longboat key. This over 10,000 sqft lot is located in a Gulfside Community with a private beach access, and...

    $1,050,000

    FULL LISTING455 LONGBOAT CLUB ROAD802
    Longboat Key, Florida FL 34228-3841

    NOTE-lot of features to read but WORTH YOUR TIME reading if you are a buyer. This condo HAS IT ALL. Enjoy GULF FRONT LIVING in this spacious 2400+ sq ft huge open floor...

    3
    3
    2,410
    $1,050,000

    FULL LISTING3060 GRAND BAY BOULEVARD183
    Longboat Key, Florida FL 34228-4180

    Breathtaking direct views of Sarasota Bay, the Gulf of Mexico, and the Harbourside Golf Course from this eighth-floor turnkey Cayman model residence at Grand Bay. This...

    3
    4
    2,550
    $1,049,000

    FULL LISTING713 PENFIELD STREET
    Longboat Key, Florida FL 34228

    short stories"...Perfect beach house..all on one level an elevated ranch home..with parking below for all your toys boat too"...with dock and add $40,000 for new pool with...

    3
    2
    2,132
    $987,000

    FULL LISTING575 SANCTUARY DRIVEA303
    Longboat Key, Florida FL 34228-3800

    This exceptional and furnished 3-Bedroom, 2.5-Bathroom beachfront condominium can be found at the one-and-only Sanctuary behind the prestigious gates of the Longboat Key...

    3
    3
    1,823
    $975,000

    FULL LISTING3629 FAIR OAKS PLACE
    Longboat Key, Florida FL 34228-4152

    SINGLE FAMILY HOME THAT LIVES LIKE A CONDO Located in the resort community of the Longboat Key Club now you can live like you are on vacation every day in the luxury...

    3
    4
    2,825
    $959,000

    FULL LISTING2120 HARBOURSIDE DRIVE647
    Longboat Key, Florida FL 34228-4265

    !!! BRING OFFERS!!! Welcome to The Atrium at Fairway Bay on Longboat Key. This 4th-floor residence behind the gates of Bay Isles rewards you with magnificent Sarasota Bay...

    3
    2
    2,039
    $950,000

    FULL LISTING3030 GRAND BAY BOULEVARD382
    Longboat Key, Florida FL 34228-4411

    TURNKEY FURNISHED, MOVE RIGHT IN! Coveted eighth-floor views abound around every corner of this lovely three-bedroom residence. Panoramic vistas will captivate you,...

    3
    3
    2,250
    $949,000

    FULL LISTING1701 GULF OF MEXICO DRIVE604
    Longboat Key, Florida FL 34228-3434

    This Aquarius Club three-bedroom penthouse residence has been completely remodeled including the kitchen, bathrooms, flooring and windows, and is stylishly furnished and...

    3
    2
    1,551
    $925,000

    FULL LISTING2105 GULF OF MEXICO DRIVE3503
    Longboat Key, Florida FL 34228-3246

    Unique opportunity to enjoy direct Gulf views, from one of only five penthouses, in an uncrowded southern Longboat Key setting. A Sally Trout, ASID, masterpiece, this...

    2
    2
    1,463
    $925,000

    FULL LISTING565 SANCTUARY DRIVEA203
    Longboat Key, Florida FL 34228-3883

    Live like you are on vacation every day on the south end of Longboat Key, behind the exclusive gates of the Longboat Key Club Islandside with easy beach access and...

    3
    3
    2,375
    $910,000

    FULL LISTING2110 HARBOURSIDE DRIVE553
    Longboat Key, Florida FL 34228-4259

    Discover the carefree, tropical lifestyle you’ve desired, where stunning water views are the gorgeous backdrop for your beautifully appointed penthouse. Perfectly...

    3
    2
    2,031
    $899,000

    FULL LISTING1211 GULF OF MEXICO DRIVE710
    Longboat Key, Florida FL 34228-3651

    Well-appointed and beautifully upgraded, this light and open residence at the sought-after Promenade is a flourish of direct Gulf-to-bay views that stretch out to the...

    2
    2
    1,827
    $899,000

    FULL LISTING1211 GULF OF MEXICO DRIVE609
    Longboat Key, Florida FL 34228-3650

    Incomparable location. Architectural elegance. Uncompromised quality. Welcome to Longboat Key's Promenade, which offers all the bells and whistles including a 24hr hour...

    2
    2
    1,827
    $899,000

    FULL LISTING3060 GRAND BAY BOULEVARD152
    Longboat Key, Florida FL 34228-4178

    Welcome to Grand Bay! One of Sarasota's more exclusive and private communities on Longboat Key. Come find out why owning this spectacular condo will be something you and...

    3
    3
    2,143
    $895,000

    FULL LISTING603 LONGBOAT CLUB ROAD1002N
    Longboat Key, Florida FL 34228-3813

    Stunning views from the Gulf of Mexico to Sarasota Bay and downtown are the perfect backdrop to begin renovating your own 10th floor beach home at Longboat Key Towers. The...

    2
    2
    1,458
    $895,000

    FULL LISTING5055 GULF OF MEXICO DRIVE536
    Longboat Key, Florida FL 34228

    Rarely available, premier 3BD/3BA northwest corner unit with all new windows and sliding glass doors! Just steps to the crystal beaches and azure blue seas of the Gulf of...

    3
    3
    1,484
    $889,000

    FULL LISTING6941 BAYSIDE DRIVE
    Longboat Key, Florida FL 34228-1003

    Perfectly situated across from the Sarasota Bay, this build-able home site offers spectacular views. Long Beach Village is only steps from kayaking, fishing, recreational...

    $849,900

    FULL LISTING775 LONGBOAT CLUB ROAD605
    Longboat Key, Florida FL 34228-3878

    Beaches #605 is a must-see. Panoramic water views from the Gulf of Mexico to Sarasota Bay, phenomenal sunrises and sunsets, the beach to the west and the golf course to...

    2
    2
    1,602
    $849,000

    FULL LISTING2425 GULF OF MEXICO DRIVE5C
    Longboat Key, Florida FL 34228-3212

    From the second you enter this unit you will be mesmerized by the beautiful gulf views. The unit has been completely renovated from top to bottom. The kitchen has...

    2
    2
    1,470
    $849,000

    FULL LISTING6326 LAGUNA DRIVE
    Longboat Key, Florida FL 34228-1500

    Large house in a private gated enclave of only 8 single family homes. Very secluded and quiet location. This community sits on 5.2 acres of shared common grounds that...

    4
    3
    2,200
    $845,000

    FULL LISTING3427 WINDING OAKS DRIVE14
    Longboat Key, Florida FL 34228-4129

    Custom upgrades by LHI Interiors abound in this impeccable 3 bedroom, 3 bath Harbourside Golf Course waterfront residence that lives like a single family home with the...

    3
    3
    2,678
    $845,000

    FULL LISTING575 SANCTUARY DRIVEA103
    Longboat Key, Florida FL 34228-3828

    Imagine living on vacation every day in this fully furnished South East corner residence at Sanctuary. This true 3 bedroom residence is perfect as a full time home or...

    3
    3
    1,823
    $829,000

    FULL LISTING2365 HARBOUR OAKS DRIVE
    Longboat Key, Florida FL 34228-4189

    If you are looking for a resort, island lifestyle in a maintenance free community that lives like a single family home, look no further! Rarely available, this charming,...

    3
    2
    2,245
    $825,000

    FULL LISTING7151 LA LENAIRE DRIVE
    Longboat Key, Florida FL 34228

    Have you ever thought about owning your own secluded white sandy beach? This remarkable piece of property on this famous Jewfish Key tropical Island is ready for your...

    $819,000

    FULL LISTING3390 BAYOU SOUND
    Longboat Key, Florida FL 34228-3020

    Beautifully remodeled home in the Bayou section of the exclusive gated community of Bay Isles on Longboat Key. The large great room featuring a vaulted ceiling is the...

    3
    3
    2,021
    $815,000

    FULL LISTING1050 LONGBOAT CLUB ROAD905
    Longboat Key, Florida FL 34228-4646

    NEW PRICE! BRING OFFERS! Step foot into this lovely residence at The Privateer behind the gates of The Longboat Key Club. Complete with full Gulf views and partial...

    2
    2
    1,290
    $800,000

    FULL LISTING2105 GULF OF MEXICO DRIVE3102
    Longboat Key, Florida FL 34228-3241

    Welcome to this direct Gulf front with full Gulf views, with walk-down to beach from a 32x16 private deck at Sunset Beach. As you enter the beach getaway, you will notice...

    2
    2
    1,273
    $799,900

    FULL LISTING775 LONGBOAT CLUB ROAD404
    Longboat Key, Florida FL 34228-3876

    Your move-in ready, carefree resort lifestyle on Longboat Key awaits on the light, bright south-side of Beaches, a beautiful Gulf front community perfectly set behind the...

    2
    2
    1,602
    $799,000

    FULL LISTING521 BROADWAY STREET
    Longboat Key, Florida FL 34228-1007

    short stories:...PLEASE NOTE"...THE TWO OLDER HISTORICAL HOMES PRESENTLY ON LOTS "'..ARE NOT INCLUDED!!!! AND SCHEDULED TO BE MOVED OFF.SOON....THE SUBJECT PROPERTY.. THIS...

    $797,000

    FULL LISTING5635 GULF OF MEXICO DRIVE203
    Longboat Key, Florida FL 34228-1930

    Direct unobstructed views of the azure Gulf of Mexico waters are enjoyed from almost every room in this spacious 2 bedroom residence located in the intimate community of...

    2
    2
    1,786
    $795,000

    FULL LISTING2525 GULF OF MEXICO DRIVE14B
    Longboat Key, Florida FL 34228-3122

    FOR A 3D VIEW OF THIS PROPERTY PLEASE CLICK ON VIRTUAL TOUR ABOVE! Breathtaking panoramic views from this 14th floor residence can be yours. Enjoy gazing at the azure...

    2
    2
    1,491
    $794,900

    FULL LISTING2045 GULF OF MEXICO DRIVEM1-208
    Longboat Key, Florida FL 34228-3251

    Best priced updated, 3 bedroom, turnkey furnished beachfront condo in the midrise towers of Seaplace on Longboat Key. This meticulously upgraded and impeccably maintained...

    3
    2
    1,532
    $785,500

    FULL LISTING454 FIREHOUSE COURT
    Longboat Key, Florida FL 34228-1118

    Walk to the beach and the Gulf, from this 1994 Long Beach village two-story contemporary beach house, located west of Gulf of Mexico Drive, in the Conrad Beach residential...

    2
    2
    2,041
    $783,750

    FULL LISTING5210 GULF OF MEXICO DRIVE201
    Longboat Key, Florida FL 34228-2032

    FULL BAY VIEWS!!! REMODEL COMPLETE! Brand new luxury vinyl plank flooring throughout and freshly painted interior! Absolutely stunning FULL Bay views to this amazing,...

    3
    2
    1,914
    $770,000

    FULL LISTING1925 GULF OF MEXICO DRIVEG8-101
    Longboat Key, Florida FL 34228-3344

    Looking for a tropical island escape? Come home to your dream condo at Seaplace! This unit, which offers 3 bedrooms and 2 bathrooms, has been beautifully remodeled. The...

    3
    2
    1,492
    $769,000

    FULL LISTING2010 HARBOURSIDE DRIVE2001
    Longboat Key, Florida FL 34228-4236

    Best three-bedroom full bay-front Fairway Bay townhome with updates currently on the market! Privately located behind the gates of Bay lsles, this spacious end-unit...

    3
    3
    2,135
    $765,000

    FULL LISTING3444 WINDING OAKS DRIVE42
    Longboat Key, Florida FL 34228-4132

    Words can’t describe this stunning, completely remodeled 3brm (or 2brm/den) 2 Bath, 2 car garage home in Winding Oaks, a maintenance-free community of 56 Nantucket-style...

    3
    2
    2,189
    $755,000

    FULL LISTING520 DE NARVAEZ DRIVE
    Longboat Key, Florida FL 34228

    On the pristine and peaceful shores of the North End of Longboat Key you will find this charming waterfront home ready for you to start living your best island life. 3...

    3
    2
    1,640
    $749,900

    FULL LISTING5635 GULF OF MEXICO DRIVE103
    Longboat Key, Florida FL 34228-1929

    Refreshed and Renewed and Back on the Market, Just Painted and ready for new owners to enjoy... Magnificent North Longboat Key Location situated directly on the Gulf of...

    2
    2
    1,786
    $749,000

    FULL LISTING3438 WINDING OAKS DRIVE43
    Longboat Key, Florida FL 34228-4132

    Tucked behind the gates of Bay Isles, you enter the enclave of Winding Oaks, a collection of maintenance free residences affording the ambiance of a single-family home. A...

    2
    2
    2,112
    $749,000

    FULL LISTING2003 HARBOUR LINKS DRIVE2003
    Longboat Key, Florida FL 34228-4280

    This sunny three-bedroom villa residence overlooks the 13th green of the Harbourside golf course lush grounds and abounds in tranquil water views. You will love the...

    3
    3
    2,500
    $749,000

    FULL LISTING1211 GULF OF MEXICO DRIVE505
    Longboat Key, Florida FL 34228-3648

    Located on the best side of the building in Promenade, the captivating fifth-floor views of lush community grounds and rolling waves of the Gulf of Mexico that stretch out...

    2
    2
    1,598
    $749,000

    FULL LISTING370 GULF OF MEXICO DRIVE411
    Longboat Key, Florida FL 34228-4021

    FIRST LIVING LEVEL, PRIVATE ENTRY WITH STAIRS BUT ALSO HAS ELEVATOR IF YOU CHOOSE. Come enjoy this tropical oasis in the highly sought after TANGERINE BAY CLUB. This...

    3
    4
    2,476
    $735,000

    FULL LISTING4964 GULF OF MEXICO DRIVE24
    Longboat Key, Florida FL 34228-2040

    WOW VIEWS, PRIVATE LOCATION, and THREE BEDROOMS! Irresistible, panoramic water views and a serene private location with very few neighbors can be yours as you enjoy this...

    3
    2
    1,442
    $725,000

    FULL LISTING1050 LONGBOAT CLUB ROAD904
    Longboat Key, Florida FL 34228-4646

    Your piece of Florida paradise awaits you in this lovely 2 bedroom, 2 bath condo situated on the highly desirable Longboat Key in The Privateer. With full Gulf to Bay...

    2
    2
    1,409
    $719,000

    FULL LISTING510 BAYPORT WAY
    Longboat Key, Florida FL 34228-2609

    Spectacular sunsets, stunning views of the Gulf of Mexico and an island resort lifestyle await you at Bayport Beach & Tennis Club. Unparalleled views of the Gulf can be...

    2
    2
    1,601
    $695,000

    FULL LISTING2425 GULF OF MEXICO DRIVE2F
    Longboat Key, Florida FL 34228-3282

    Direct Gulf-Beach front end unit on Longboat Key. Magnificent Gulf, Beach and Sunset views 12 months of the year from floor to ceiling windows.This 2 bedroom/ 2 bath open...

    2
    2
    1,513
    $679,000

    FULL LISTING1975 GULF OF MEXICO DRIVEG4-107
    Longboat Key, Florida FL 34228-3348

    NEW PRICE: On this great large two bedroom/2bath condominium with Direct Unobstructed Gulf and Garden Views. Enjoy every day having a beverage of your choice and reading...

    2
    2
    1,257
    $675,000

    FULL LISTING690 JUNGLE QUEEN WAY
    Longboat Key, Florida FL 34228-1808

    Waterfront Home. Walk to the Beach, with deeded beach access. Situated on a sailboat water canal, leading to the Gulf. Once you enter through the double door entryway,...

    3
    2
    2,317
    $650,000

    FULL LISTING100 SANDS POINT ROAD219
    Longboat Key, Florida FL 34228-3904

    The condominiums of Sands Point sit Beachfront on the Southern most tip of Longboat Key, behind the Gates of the Longboat Key Club Resort. Full Unobstructed views of the...

    2
    2
    1,492
    $648,400

    FULL LISTING3480 BAYOU SOUND
    Longboat Key, Florida FL 34228-3000

    Hurry and get the LAST remaining lot in Bayou Sound in Bay Isles!!! A spacious 100 X 125 feet lot cleared and ready to build on with your custom builder: gas, electric,...

    $640,000

    FULL LISTING1075 GULF OF MEXICO DRIVE105
    Longboat Key, Florida FL 34228-3634

    Welcome to Beachplace on WORLD FAMOUS Longboat Key and This FABULOUS First-Floor Unit Featuring Private Steps Leading From Your Balcony Down to COVERED ASSIGNED PARKING &...

    3
    2
    1,819
    $638,900

    FULL LISTING5055 GULF OF MEXICO DRIVE512
    Longboat Key, Florida FL 34228-2003

    Direct Gulf front at Club Longboat. Offered turnkey furnished, including a Steinway baby grand piano, 2 sleeper sofas, and wine cooler. Enjoy year round sunsets from...

    2
    2
    1,484
    $635,000

    FULL LISTING735 SAINT JUDES DRIVE S
    Longboat Key, Florida FL 34228-1815

    Ready to wake up on the water? This two-story home has canal for your boat in the back and breathtaking views of the Sarasota Bay in the front. Deeded access! A/C...

    4
    2
    2,014
    $635,000

    FULL LISTING4825 GULF OF MEXICO DRIVE401
    Longboat Key, Florida FL 34228-2120

    Direct gulf front 2 bedroom/2 bath residence offers full unobstructed views of the Gulf of Mexico from almost every room. Open the sliders or sit on the terrace and listen...

    2
    2
    1,393
    $615,000

    FULL LISTING5135 GULF OF MEXICO DRIVE203
    Longboat Key, Florida FL 34228-2012

    LIVE ON VACATION NOW! 3 bedrooms are hard to find on this relaxing Longboat Key Gulf beach, especially in a quiet 2 story 8 unit building! Lots space for a family and...

    3
    2
    1,516
    $599,999

    FULL LISTING5311 GULF OF MEXICO DRIVE9
    Longboat Key, Florida FL 34228

    Hitting the Market Now, Beach Castle Beach Resort, perfect for your dream beach home. This Key West style boutique resort is directly on the Sands of the stunning white...

    2
    2
    1,110
    $599,000

    FULL LISTING3416 WINDING OAKS DRIVE50
    Longboat Key, Florida FL 34228-4125

    Winding Oaks in Bay Isles of Longboat Key is one of the most popular neighborhoods with its coastal architecture, lakes and proximity to the amenities of the Longboat Key...

    2
    2
    2,112
    $599,000

    FULL LISTING1115 GULF OF MEXICO DR.403
    Longboat Key, Florida FL 34228

    Views to Ocean and Bay from fourth floor reimagined prime unit in Brand New Skin.Turnkey withover $100,000 in upgrades Light Bright GRANITE COUNTERS NEW BATHS Plank Tiles ...

    2
    2
    1,503
    $599,000

    FULL LISTING1095 GULF OF MEXICO DRIVE604
    Longboat Key, Florida FL 34228-3671

    Sunrise to sunset views abound! This turnkey furnished penthouse Beachplace residence with new windows, sliders and front door, is ready to rent, renovate or enjoy. Top...

    2
    2
    1,503
    $589,000

    FULL LISTING724 MARBURY LANE
    Longboat Key, Florida FL 34228-1442

    Reduced to sell! $100,000 price reduction on this prime canal front lot on Longboat Key. Over $60,000 invested in a new seawall completed in 2019. The homesite comes with...

    $579,000

    FULL LISTING3235 GULF OF MEXICO DRIVEA506
    Longboat Key, Florida FL 34228-2838

    Fully unobstructed views of Gulf of Mexico's surf, powdery sands and incredible Florida sunsets 365 days a year! Located in serene Longboat Key's Portobello condo...

    2
    2
    1,505
    $565,000

    FULL LISTING736 BAYPORT WAY
    Longboat Key, Florida FL 34228-2636

    Spectacular sunsets, stunning views of the Gulf of Mexico and an island resort lifestyle await you at Bayport Beach & Tennis Club. This second floor unit was fully...

    2
    2
    1,260
    $560,000

    FULL LISTING5393 GULF OF MEXICO DRIVE103
    Longboat Key, Florida FL 34228-2025

    First floor residence offering a secluded private, park like setting with a ground level walkout to the beach. Wake to the sound of surf and dip your toes in the Gulf of ...

    2
    2
    1,300
    $559,000

    FULL LISTING515 FOREST WAY
    Longboat Key, Florida FL 34228-1826

    Investors take notice!! Tremendous income property. Turnkey furnished and ready for your group (Can sleep 8 comfortably). Historically, current owner has made $50k to...

    3
    3
    2,880
    $559,000

    FULL LISTING4900 GULF OF MEXICO DRIVE201
    Longboat Key, Florida FL 34228-2011

    Great water views, luxury finishes, tile floors throughout, boat slips (lifts allowed) and beach access! What could be better? This beautifully updated, light and airy,...

    2
    2
    1,561
    $558,000

    FULL LISTING650 TRITON BEND
    Longboat Key, Florida FL 34228-2929

    Imagine the wonderful home you can build to enjoy a lifestyle that is incomparable to anywhere else. Wake up each morning to eye-catching sunrises in the east, and drift...

    $550,000

    FULL LISTING610 NEPTUNE AVENUE
    Longboat Key, Florida FL 34228

    Imagine the wonderful home you can build to enjoy a lifestyle that is incomparable to anywhere else. Wake up each morning to eye-catching sunrises in the east, and drift...

    $550,000

    FULL LISTING580 LINLEY STREET
    Longboat Key, Florida FL 34228-1024

    Located in the quaint neighborhood of Longbeach Village and tucked away within lush landscaping the Linley Cottage is everything you are looking for and so much more!...

    2
    2
    1,673
    $544,900

    FULL LISTING2089 GULF OF MEXICO DRIVEG1-202
    Longboat Key, Florida FL 34228

    BEACHFRONT GET-AWAY! BE AWED BY GLOWING SUNSETS AND SOOTHED BY THE SOUND OF THE GULF WATERS from this rarely available 1 BR loft with 2 FULL baths. Ready for immediate...

    1
    2
    1,094
    $525,000

    FULL LISTING1912 HARBOURSIDE DRIVE603
    Longboat Key, Florida FL 34228-4209

    CONDO LIVING THAT FEELS LIKE A HOUSE IN UPDATED FLORIDA STYLE AND NO EXTERIOR CARE WORRY! This 2BD/2.5BA/ 2 car garage townhome offers a sought-after desire for today’s...

    2
    3
    1,700
    $523,000

    FULL LISTING4700 GULF OF MEXICO DRIVE306
    Longboat Key, Florida FL 34228-2147

    Great Sarasota Bay views, luxury finishes and a turn-key furnished chic decor are yours to be had in this sunny and inviting 2 bedroom/2 bathroom end unit condo with 1561...

    2
    2
    1,376
    $519,000

    FULL LISTING712 BAYPORT WAY712
    Longboat Key, Florida FL 34228-2626

    Relax and enjoy gorgeous direct Gulf Views from your lanai, living room and master bedroom from this second floor (top floor) condominium. Listen to the sounds of the surf...

    2
    2
    1,260
    $514,000

    FULL LISTING3453 GULF OF MEXICO DRIVE252
    Longboat Key, Florida FL 34228-2827

    Welcome to The Sea Horse Resort on Longboat Key. 2-bedroom/2-bath direct Gulf front with full Gulf views. End unit, updated with the luxury of nightly rentals with an...

    2
    2
    994
    $499,900

    FULL LISTING3630 GULF OF MEXICO DRIVE103
    Longboat Key, Florida FL 34228-2830

    A rare combination of features at Buttonwood Cove awaits your discovery. Situated on 5 superbly landscaped acres on the Gulf of Mexico with 500 feet of beach as well as...

    2
    2
    1,479
    $499,000

    FULL LISTING821 BAYPORT WAY
    Longboat Key, Florida FL 34228-2666

    Stunning Bay views and an island resort lifestyle await you at Bayport Beach & Tennis Club. This highly desirable and sought after first floor unit is waiting for your...

    2
    2
    1,601
    $489,000

    FULL LISTING4725 GULF OF MEXICO DRIVE109
    Longboat Key, Florida FL 34228-2129

    Sand Cay is a "Gem by the Sea." This community will provide you and your family with years of of memories as it has for the family who owned this residence for decades....

    2
    2
    1,032
    $475,000

    FULL LISTING2930 GULF OF MEXICO DRIVE2930
    Longboat Key, Florida FL 34228-2905

    Treehouse at Seaside Garden Retreat is situated to capture coastal breezes and brilliant light defining the true meaning of light and airy. Literally a stone’s throw...

    2
    2
    1,451
    $475,000

    FULL LISTING3440 GULF OF MEXICO DRIVE7
    Longboat Key, Florida FL 34228-2809

    If old Florida atmosphere appeals to you, you have found it in The Dock on the Bay. This beautifully updated townhouse lives like a home in a charming, intimate complex...

    2
    3
    1,679
    $469,000

    FULL LISTING1085 GULF OF MEXICO DRIVE203
    Longboat Key, Florida FL 34228-3666

    A perfect getaway or investment property in the luxurious Beachplace Community. This mostly furnished 1,503 square foot, 2 Bedroom, 2 bathroom condominium balcony...

    2
    2
    1,503
    $464,900

    FULL LISTING530 COMPANION WAY
    Longboat Key, Florida FL 34228-1802

    DIRECTLY LOCATED ACROSS THE STREET FROM THE BEACH- Privately owned deeded access leads you to one of the finest beaches on Longboat Key. Its quiet and pristine, with no...

    2
    1
    1,104
    $459,000

    FULL LISTING625 JACKSON WAY
    Longboat Key, Florida FL 34228

    Introducing The Preserve at Longbeach, an exclusive enclave of 12 new construction, light filled and luxurious contemporary homes. Refinement meets relaxation at the north...

    $450,000

    FULL LISTING2016 HARBOURSIDE DRIVE352
    Longboat Key, Florida FL 34228-4243

    Looking for a smaller boutique building? Something with private views where you are not looking into your neighbors’ balcony? How about more than a sliver of water view?...

    2
    2
    1,192
    $449,000

    FULL LISTING827 BAYPORT WAY827
    Longboat Key, Florida FL 34228-2670

    FURNISHED 2/2 resident-preferred, first level, END UNIT with no condo above, no condo below and no unit to the right. This is Bayport Beach and Tennis Club’s popular...

    2
    2
    1,378
    $449,000

    FULL LISTING4140 GULF OF MEXICO DRIVE6
    Longboat Key, Florida FL 34228-2643

    NEW PRICE: Nestled amid lush and well-maintained landscaping this casual intimate bay to beach community with only eight residences is located mid-Longboat Key with boat...

    2
    2
    1,144
    $439,000

    FULL LISTING420 FIREHOUSE COURT6
    Longboat Key, Florida FL 34228-1146

    Great opportunity to own a gorgeous and meticulously decorated villa style home in the coveted north end of Longboat Key. Just steps away from the pristine gulf water and...

    2
    2
    1,015
    $434,900

    FULL LISTING3330 GULF OF MEXICO DRIVE102-D
    Longboat Key, Florida FL 34228-2819

    Looking for a place to escape and enjoy what the island lifestyle has to offer, look no more! New to the market and rarely available is this completely renovated, two-...

    2
    2
    1,362
    $425,000

    FULL LISTING842 EVERGREEN WAY
    Longboat Key, Florida FL 34228-1850

    Island life reimagined. Begin every day beautifully in this one-of-a-kind, stunning renovation with fit and finishes that will impress the most discerning, nestled in the...

    2
    3
    1,440
    $425,000

    FULL LISTING5841 GULF OF MEXICO DRIVE247
    Longboat Key, Florida FL 34228-1701

    A great weekend getaway on the beach or an excellent rental investment. Designed as a 2/2 condo or two 1/1 condos and available to rent even for one night occupation....

    2
    2
    760
    $419,000

    FULL LISTING4340 FALMOUTH DRIVE104
    Longboat Key, Florida FL 34228-2326

    It's a great time to be a part of this extremely active, amenity rich community. A perfect place for all the possibilities... year round living, vacation, investment or...

    2
    2
    1,072
    $409,999

    FULL LISTING3330 GULF OF MEXICO DRIVE207-D
    Longboat Key, Florida FL 34228-2842

    This Turnkey furnished 2nd-floor condominium is located off the Intracoastal Waterway of Sarasota Bay. It is well-appointed and the interior was painted just days ago....

    2
    2
    1,362
    $409,000

    FULL LISTING4621 GULF OF MEXICO DRIVE11D
    Longboat Key, Florida FL 34228-2101

    Premier Rental Community on the Gulf of Mexico Longboat Key offers owners year round rental income through the convenient Association managed on-site rental program. Unit...

    2
    2
    756
    $405,000

    FULL LISTING4340 FALMOUTH DRIVE303
    Longboat Key, Florida FL 34228-2327

    Enjoy the island life in this beautiful, move-in ready home within the friendly, active community of Longboat Harbour. Beautifully updated and located on the top floor for...

    2
    2
    1,072
    $400,000

    FULL LISTING6324 LAGUNA DRIVE
    Longboat Key, Florida FL 34228

    Incredible opportunity to build your own custom home on the last available lot in Laguna Yacht Village. Enjoy the privacy and convenience of this gated 5 acre Longboat Key...

    $400,000

    FULL LISTING4540 GULF OF MEXICO DRIVEPH2
    Longboat Key, Florida FL 34228-2251

    Ready for immediate enjoyment or earning much desired rental income, you're going to love this sunny and bright 2 Bedroom/2 Bathroom, Turn-Key Furnished PENTHOUSE condo...

    2
    2
    1,312
    $400,000

    FULL LISTING843 EVERGREEN WAY
    Longboat Key, Florida FL 34228-1851

    Experience the pinnacle of a carefree island lifestyle in this updated, contemporary-style residence in Cedar’s East on Longboat Key. Sold beautifully furnished...

    2
    3
    1,440
    $395,000

    FULL LISTING6830 LONGBOAT DRIVE S
    Longboat Key, Florida FL 34228

    Introducing The Preserve at Longbeach, an exclusive enclave of 12 new construction, light filled and luxurious contemporary homes. Refinement meets relaxation at the north...

    $395,000

    FULL LISTING5310 GULF OF MEXICO DRIVE12
    Longboat Key, Florida FL 34228

    One of the best small resort style properties on Longboat Key! Tropical Key West style boutique resort. Located in Mid- North Longboat Key which provides a tranquil and...

    2
    2
    1,014
    $395,000

    FULL LISTING4330 FALMOUTH DRIVE106
    Longboat Key, Florida FL 34228-2362

    Excellent 2/2 furnished condo with WATER VIEW! Beautiful 2 bedrooms and 2 bathrooms condo direct on the canal overlook the harbor. Longboat Harbour is a waterfront...

    2
    2
    1,072
    $395,000

    FULL LISTING524 SPANISH DRIVE S125
    Longboat Key, Florida FL 34228-1630

    Lovely updated villa at Spanish Main Yacht Club. All new windows 6/20, all new flooring 2/20, new appliances 4/20, Landscape redone, Baths Redone, Roof 3 years (tile and...

    2
    2
    1,399
    $387,500

    FULL LISTING450 GULF OF MEXICO DRIVEB302
    Longboat Key, Florida FL 34228-4044

    A boater lover’s dream location on Sarasota Bay with deep water access and dockage with this beautifully remodeled and meticulously maintained 1,306 SF residence with...

    2
    2
    1,194
    $384,900

    FULL LISTING723 EL CENTRO723
    Longboat Key, Florida FL 34228-1617

    You are going to fall in LOVE with arguably one of the best remodeled and expanded free standing homes at this landmark Longboat Key community. Most others available are...

    3
    2
    1,441
    $375,000

    FULL LISTING682 SPANISH DRIVE S105
    Longboat Key, Florida FL 34228-1632

    Welcome, all boaters to this beautifully updated and meticulously maintained 1,419 square foot villa in the highly sought-after waterfront community of Spanish Main Yacht...

    2
    2
    1,419
    $374,900

    FULL LISTING4310 FALMOUTH DRIVEA-103
    Longboat Key, Florida FL 34228-2316

    IT'S THIS SPECTACULAR FULL SARASOTA BAY VIEW FROM THIS 2 BEDROOM, 2 BATH CONDO THAT WILL SELL THIS CONDO TO YOU! Relax on the enclosed lanai, the beautiful water birds and...

    2
    2
    928
    $369,000

    FULL LISTING3320 GULF OF MEXICO DRIVE206-C
    Longboat Key, Florida FL 34228-2841

    Bring your boat and enjoy paradise! Lovely second floor condo with a view from the front patio of the bay and pool. The unit was completely renovated in 2017 and...

    2
    2
    1,187
    $359,900

    FULL LISTING862 EVERGREEN WAY862
    Longboat Key, Florida FL 34228-1852

    Gorgeous newly renovated condo with brand new kitchen and bath! This condo sits on the Sarasota Bay and is only steps away from the water. Bring your kayak and bathing...

    2
    3
    1,440
    $352,000

    FULL LISTING6860 LONGBOAT DRIVE S
    Longboat Key, Florida FL 34228-1036

    Introducing The Preserve at Longbeach, an exclusive enclave of 12 new construction, light filled and luxurious contemporary homes. Refinement meets relaxation at the north...

    $349,500

    FULL LISTING739 EL CENTRO
    Longboat Key, Florida FL 34228-1617

    This beautifully renovated ground-level villa has been meticulously maintained, and is located a stone’s throw away from the heated community pool, beautiful marina and...

    2
    2
    1,394
    $349,000

    FULL LISTING603 CEDARS COURT603
    Longboat Key, Florida FL 34228-1845

    Nicely updated townhome in the popular Cedars East Tennis Resort. This unit is in an excellent location that is just steps away to the Jr. Olympic heated swimming pool,...

    2
    2
    1,332
    $345,000

    FULL LISTING4390 EXETER DRIVEI-102
    Longboat Key, Florida FL 34228-2209

    Great waterfront 2 bedroom with updated bathrooms and beautiful ceramic tiles throughout. The Lanai is enclosed with sliding doors, adding more living space and offered...

    2
    2
    992
    $345,000

    FULL LISTING528 FOREST WAY
    Longboat Key, Florida FL 34228-1833

    Cedars East Bayfront Resort Community on Longboat Key’s tranquil north end! This spacious, completely updated, fully furnished 2 bedroom, 2 ½ bath townhome has 9ft...

    2
    3
    1,440
    $340,000

    FULL LISTING600 SUTTON PLACE101
    Longboat Key, Florida FL 34228-2314

    No elevator, no stairs, Sutton Place has it all! This perfect get away or full time home for you and your pets. Tiled throughout with a spacious open kitchen (newer...

    1
    1
    696
    $335,000

    FULL LISTING676 EL CENTRO
    Longboat Key, Florida FL 34228-1616

    All the work has been done, just come and enjoy this delightfully updated 2-bedroom, 2-bath 1,427 sq. ft. villa in the beautiful waterfront community of Spanish Main Yacht...

    2
    2
    1,427
    $334,500

    FULL LISTING3330 GULF OF MEXICO DRIVE304-D
    Longboat Key, Florida FL 34228-2821

    READY FOR REHAB...IF you're looking for an investment opportunity this could be your lucky day! With spectacular 3rd floor Water Views, potential for a Dock, updated...

    2
    2
    1,106
    $330,000

    FULL LISTING622 CEDARS COURT14
    Longboat Key, Florida FL 34228-1843

    The winning trifecta. Water view plus one-year paid full family membership plus booked vacation rentals early 2021. This meticulously maintained furnished Cedars townhome...

    2
    3
    1,440
    $328,000

    FULL LISTING3320 GULF OF MEXICO DRIVE103-C
    Longboat Key, Florida FL 34228-2801

    This two-bedroom - two bath ground floor residence is located in a small quiet complex on beautiful Longboat Key. Unit has been freshly painted and is in move in...

    2
    2
    1,155
    $324,900

    FULL LISTING5841 GULF OF MEXICO DRIVE244
    Longboat Key, Florida FL 34228-1701

    Ready to purchase your beachfront property? This quaint 1-bedroom / 1-bathroom condo is located on the offshore barrier island of Longboat Key. The entire length of the...

    1
    1
    520
    $320,000

    FULL LISTING802 EVERGREEN WAY802
    Longboat Key, Florida FL 34228-1848

    Well maintained townhome located in popular Cedars East Tennis Resort. Partial bay views from lanai, kitchen, master bedroom and guest bedroom. Enjoy the comforts of the...

    2
    3
    1,501
    $319,900

    FULL LISTING6750 GULF OF MEXICO DRIVE167
    Longboat Key, Florida FL 34228

    Beach lovers welcome to Whitney Beach! This lush & tropical community is located on the North Shore of pristine Longboat Key. Lush mature landscapes abound with room to...

    1
    1
    836
    $309,500

    FULL LISTING2039 GULF OF MEXICO DRIVEG3-211
    Longboat Key, Florida FL 34228-3252

    This wonderfully maintained two-bedroom townhome at Seaplace is light and open, offering lush garden views of the community. Turnkey furnished and ready to enjoy, the...

    2
    3
    1,214
    $300,000

    FULL LISTING4420 EXETER DRIVE105
    Longboat Key, Florida FL 34228-2219

    FULL BAY FRONT, WALK IN, WALK OUT CONDO THAT HAS HAD A COMPLETE INTERNAL RECONSTRUCTION. THE WATER VIEW IS TRULY AMAZING AND MUST BE SEEN TO BE APPRECIATED. Fully...

    1
    1
    725
    $299,000

    FULL LISTING610 HIBISCUS WAY
    Longboat Key, Florida FL 34228

    Introducing The Preserve at Longbeach, an exclusive enclave of 12 new construction, light filled and luxurious contemporary homes. Refinement meets relaxation at the north...

    $295,000

    FULL LISTING620 HIBISCUS WAY
    Longboat Key, Florida FL 34228

    Introducing The Preserve at Longbeach, an exclusive enclave of 12 new construction, light filled and luxurious contemporary homes. Refinement meets relaxation at the north...

    $295,000

    FULL LISTING3320 GULF OF MEXICO DRIVE101-C
    Longboat Key, Florida FL 34228-2801

    Excellent purchase for any investor to own this 2 bedroom, 2 bath first floor corner unit at Longboat Arms. The beach access is conveniently located just across the...

    2
    2
    1,154
    $285,000

    FULL LISTING2600 HARBOURSIDE DRIVER-13
    Longboat Key, Florida FL 34228-4115

    80 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. The deep water marina is as...

    $275,000

    FULL LISTING3465 GULF OF MEXICO DRIVE106
    Longboat Key, Florida FL 34228-2827

    A golden opportunity to own a Gulf front condo directly on the beach, plus put money in your pocket. This ground floor studio is located on Longboat Key minutes from St....

    1
    342
    $274,900

    FULL LISTING3806 GULF OF MEXICO DRIVEC-312
    Longboat Key, Florida FL 34228-2738

    Rush to this Outstanding Longboat Key Deal of the Day!! One of the Lowest Priced FURNISHED 2 Bedroom, 2 Bathroom Units available on the Island! This Super 3rd Floor Unit...

    2
    2
    1,062
    $269,900

    FULL LISTING3806 GULF OF MEXICO DRIVEC303
    Longboat Key, Florida FL 34228-2738

    ACCEPTING BACK-UP CONTRACTS. “Run, don’t walk”! This is one of the lowest priced 2 bedroom, 2 bath condos on Longboat Key. Hurry the Gulf views are spectacular from...

    2
    2
    1,046
    $269,900

    FULL LISTING3806 GULF OF MEXICO DRIVEC102
    Longboat Key, Florida FL 34228

    Beautiful remodeled Condo in the luxurious Beach Harbor Club. This Condominium spans from the gulf to the bay with access to both. On one side you have a private beach...

    2
    2
    1,027
    $269,000

    FULL LISTING2600 HARBOURSIDE DRL-05
    Longboat Key, Florida FL 34228

    NICE 68 X 22 SLIP. EASY TO DOCK YOUR VESSEL IN THIS SLIP, GREAT VIEW OF THE BAY W/ ADDED DOCK SPACE ON L DOCK! WORLD CLASS YATCH CLUB SLIP INCLUDES: Telephone, cable...

    $258,500

    FULL LISTING4360 CHATHAM DRIVEF304
    Longboat Key, Florida FL 34228-2335

    Relaxing Water view from this 3rd floor one bedroom condo with partial gulf view form magnificent updated Kitchen with granite counter tops& extended backsplash, stainless...

    1
    1
    747
    $249,000

    FULL LISTING3440 GULF OF MEXICO DRIVE14
    Longboat Key, Florida FL 34228-2809

    Charming, casual, ground floor villa-style unit ready for you. Ideal for an island rental or getaway! Furnished with a few exceptions so just bring yourself and a...

    1
    1
    900
    $245,000

    FULL LISTING86 TWIN SHORES BOULEVARD86
    Longboat Key, Florida FL 34228-2714

    Twin Shores is an amazing community on Longboat Key with Gulf to Bay access. The residents enjoy private beach access, along with a private marina on the property for...

    2
    2
    880
    $241,000

    FULL LISTING40 TWIN SHORES BOULEVARD
    Longboat Key, Florida FL 34228-2711

    Wonderful relaxing Beach Home, completely remodeled, furniture included. New roof, New Electric, New Plumbing New Baths New kitchen etc etc. Owner Financing Available.

    2
    2
    847
    $222,222

    FULL LISTING2600 HARBOURSIDE DRIVER-5
    Longboat Key, Florida FL 34228-4115

    A 65 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina located on R-dock with uninterrupted views of Sarasota Bay. Enjoy all the amenities of the private Longboat Key...

    $210,000

    FULL LISTING630 COMPANION WAY
    Longboat Key, Florida FL 34228

    Deeded beach access across the street, a canal easement for dropping in a kayak, canoe, or paddleboard, and located across the street from the Cedars Tennis Resort,. In...

    $208,750

    FULL LISTING85 TWIN SHORES BOULEVARD85
    Longboat Key, Florida FL 34228-2714

    Come take advantage of Island living at this beautiful community of Twin Shores on Longboat Key. This community features private beach access, marina access for the...

    2
    2
    800
    $191,000

    FULL LISTING2800 HARBOURSIDE DRIVEE-06
    Longboat Key, Florida FL 34228-3124

    55 x 21 ft. Boat Slip at Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other...

    $190,000

    FULL LISTING2600 HARBOURSIDE DRIVEC-19
    Longboat Key, Florida FL 34228-4115

    A 72 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other...

    $187,000

    FULL LISTING571 SAINT JUDES DRIVE2
    Longboat Key, Florida FL 34228-1801

    This condo is the best value on Longboat Key under 200K that is fully updated and ready to enjoy. This is one of just 8 units and has a true Old Florida beachy feel to...

    1
    1
    372
    $180,000

    FULL LISTING2600 HARBOURSIDE DRIVEH-04
    Longboat Key, Florida FL 34228-4115

    55 x 20 ft. Boat Slip at Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other...

    $175,000

    FULL LISTING2800 HARBOURSIDE DRIVEF-06
    Longboat Key, Florida FL 34228-3124

    A 70 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member....

    $175,000

    FULL LISTING571 SAINT JUDES DRIVE8
    Longboat Key, Florida FL 34228-1801

    Island living with Old Florida charm. Remarkable studio with potential for separate 1 bedroom, open floor plan, kitchen and private bath. Cozy and comfortable, located in...

    1
    391
    $169,000

    FULL LISTING571 SAINT JUDES DRIVE7
    Longboat Key, Florida FL 34228-1801

    Old Florida Charm!!! Pied-a-terre, Beach Cabana, Weekend Getaway, or strictly investment, it doesn't get finer than this. Located in a quaint, private community of only 8...

    1
    1
    391
    $169,000

    FULL LISTING2600 HARBOURSIDE DRIVEH-07
    Longboat Key, Florida FL 34228-4115

    55 x 20 ft. Boat Slip at Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other...

    $169,000

    FULL LISTING3710 GULF OF MEXICO DRIVEF2
    Longboat Key, Florida FL 34228-2764

    PERFECT BEACH-TO-BAY COMMUNITY! Gulfshore of Longboat Key, Inc. offers it all. It has approximately 450 feet of frontage on the Gulf of Mexico, a marina on Sarasota Bay, a...

    2
    1
    680
    $164,900

    FULL LISTING2800 HARBOURSIDE DRIVEF-07
    Longboat Key, Florida FL 34228-3124

    70' Boat Slip at the full-service Longboat Key Moorings Marina. World class facilities and resort amenities await you including storm-protected deep water yacht slips,...

    $150,000

    FULL LISTING2800 HARBOURSIDE DRIVEF-05
    Longboat Key, Florida FL 34228-3124

    70' Boat Slip at the full-service Longboat Key Moorings Marina. World class facilities and resort amenities await you including storm-protected deep water yacht slips,...

    $150,000

    FULL LISTING3710 GULF OF MEXICO DRIVEC20
    Longboat Key, Florida FL 34228-2755

    MAKE THIS YOUR PART OR FULL TIME FLORIDA GETAWAY!!! As you enter this home, you will find furnishings and colors that will make you feel right at home. The floor plan...

    1
    1
    640
    $149,900

    FULL LISTING3710 GULF OF MEXICO DRIVEB21
    Longboat Key, Florida FL 34228-2753

    TROPICAL PARADISE. Gulfshore of Longboat Key, Inc. offers it all. It extends from the Gulf of Mexico to Sarasota Bay. It has approximately 450 feet of frontage on the...

    1
    1
    564
    $135,500

    FULL LISTING3710 GULF OF MEXICO DRIVEE11
    Longboat Key, Florida FL 34228-2761

    BEACH TO BAY COMMUNITY! Gulfshore of Longboat Key has it all - private, pristine sand beach, on the Gulf of Mexico, a marina on Sarasota Bay, large community pool,...

    2
    1
    608
    $129,900

    FULL LISTING2600 HARBOURSIDE DRIVEP-11
    Longboat Key, Florida FL 34228-4115

    48 x 20 ft. Boat Slip with exceptional views of Sarasota Bay on the east side of the marina along with a very desirable location just inside the T-dock for ease of access,...

    $120,000

    FULL LISTING2600 HARBOURSIDE DRIVEC-14
    Longboat Key, Florida FL 34228-4115

    55 x 20 ft. Boat Slip with exceptional views of Sarasota Bay on the east side of the marina along with a very desirable location just inside the T-dock for ease of access,...

    $95,000

    FULL LISTING2600 HARBOURSIDE DRIVEI-12
    Longboat Key, Florida FL 34228-4115

    45 x 21 ft. Boat Slip at Longboat Key Moorings Marina with easy dock access. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as...

    $79,900
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