Longboat key | Southwest Florida Real Estate

LONGBOAT KEY | Southwest FL Real Estate

Longboat Key Homes

Longboat Key is on the southern tip of Anna Maria Island and lies within Manatee County to its north and Sarasota County to its south. It is surrounded by the Gulf of Mexico and Sarasota Bay. The New Pass Bridge connects it to Lido Key to its south and the Longboat Pass Bridge connects it to Anna Maria Island to its north. It draws residents and visitors from all over the world to its beaches and parks. Homes on the island include condominiums, villas and townhouses, mobile homes and single family homes priced from $100,000 up to $22,000,000.

The Water Club - The two 11-story towers of The Water Club are found on the Gulf of Mexico on the southern end of Longboat Key. There are 172 two and three bedroom luxury condos ranging from 1,400 to over 3,400 square feet. The resort-style community has a junior Olympic-sized swimming pool and hot tub, 4 Har Tru tennis courts, a fitness facility with a sauna and steam room and a community clubhouse with a library, game and billiard rooms, ballroom and fully equipped catering kitchen. A wooden boardwalk takes you to a private beach. There is secured parking under the buildings along with some enclosed garages. Gates are guarded around the clock and there is also a concierge service. The buildings overlook a sparkling water fountain and the beautiful Gulf of Mexico.

Seaplace - This waterfront condominium community is located on the Gulf of Mexico on 42 acres with tropical landscaping, flowering trees and gardens. It consists of 2 mid-rise buildings, 9 garden buildings and 12 townhomes. Amenities include 2 heated pools with spas, 3 Har Tru tennis courts, clubhouse with fitness center, walking trails, water access and a 24 hour guarded gate. You'll find views of the Gulf of Mexico, Sarasota Bay and the gardens. Fees include cable t.v., security, manager, water, sewer and trash.

Let us help you with your search for your "Piece of Beach Paradise"! More information can be found at www.longboatkey.org.

Just Listed | Latest Homes for Sale on Longboat Key

2525 Gulf Of Mexico Drive Unit 6C, Longboat Key image

2525 Gulf Of Mexico Drive Unit 6C, Longboat Key $1,650,000

Nestled directly on the pristine shores of Longboat Key, this stunning 6th floor beachfront 2 bedroom, 2 bathroom condominium has been meticulously remodeled to offer the...

2 Beds
2 Baths
Islands West SubDv.
34228 Zip Code

554 Jessmyth Drive, Longboat Key $2,995,000

Rare near half acre (.48) lot with bay and canal views! This Longboat Estates property features a brand new 155ft concrete seawall and allows for boating, fishing or sim...

Longboat Key Estates SubDv.
34228 Zip Code

2045 Gulf Of Mexico Drive Unit M1-507, Longboat Key image

2045 Gulf Of Mexico Drive Unit M1-507, Longboat Key — M-1 $748,750

This turnkey-furnished fifth floor unit is on the southwest side of Building M-1, one unit back from the direct gulf front corner unit #508. Unit #507 has southern angle ...

2 Beds
2 Baths
Seaplace SubDv.
34228 Zip Code

2185 Gulf Of Mexico Drive Unit 211, Longboat Key image

2185 Gulf Of Mexico Drive Unit 211, Longboat Key — Villa Di Lancia $2,095,000

Welcome to an exceptional find in Villa Di Lancia, one of the premier communities on the south end of Longboat Key and where luxury meets convenience. This remarkable cor...

3 Beds
3 Baths
Villa Di Lancia SubDv.
34228 Zip Code

3060 Grand Bay Boulevard Unit 153, Longboat Key image

3060 Grand Bay Boulevard Unit 153, Longboat Key — Grand Bay I $1,999,500

Welcome to tropically elegant living at its finest in this exquisite 5th floor residence in Longboat Key’s esteemed Grand Bay community. With 2,550 sq. ft. of living area...

2 Beds
3.5 Baths
Grand Bay SubDv.
34228 Zip Code

2055 Gulf Of Mexico Drive Unit G2-213, Longboat Key image

2055 Gulf Of Mexico Drive Unit G2-213, Longboat Key — G2 $725,000

NO EXPENSE SPARED, EVERYTHING REPLACED, GULF AND GREEN BELT VIEWS AWAIT FROM YOUR TOP FLOOR SEAPLACE CONDO! Completely remodeled in 2022, this beautiful gulf-facing one-b...

1 Beds
1.5 Baths
Seaplace SubDv.
34228 Zip Code

2165 Gulf Of Mexico Drive Unit 111, Longboat Key image

2165 Gulf Of Mexico Drive Unit 111, Longboat Key — Villa Di Lancia $2,250,000

Charming coastal haven on Sarasota’s nicest island, Longboat Key. This 3 Bedroom, 3 Bath, nearly 2,500 sq ft END UNIT condo has FULL GULF VIEWS. As you step onto your nea...

3 Beds
3 Baths
Villa Di Lancia SubDv.
34228 Zip Code

2600 Harbourside Drive Unit H-05, Longboat Key image

2600 Harbourside Drive Unit H-05, Longboat Key $350,000

55 x 20 ft. Boat Slip with easy access to the Marina Village at the south end of the basin in Longboat Key Moorings Marina. Direct access to Sarasota Bay and the ICW. The...

Bay Isles SubDv.
34228 Zip Code

726 Spanish Drive N, Longboat Key $539,000

Welcome to this charming 2/2 villa with beautiful Terrazzo floors that lives like a single-family home and has a real neighborhood feel. Meticulously kept with one of the...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

2120 Harbourside Drive Unit 627, Longboat Key image

2120 Harbourside Drive Unit 627, Longboat Key — Fairway Bay Atrium $949,000

Located behind the gates of Bay Isles, Fairway Bay is a resort style, amenity rich community. Walk through the welcoming & tropical atrium and take the elevator to the se...

3 Beds
2 Baths
Fairway Bay SubDv.
34228 Zip Code

3060 Grand Bay Boulevard Unit 182, Longboat Key image

3060 Grand Bay Boulevard Unit 182, Longboat Key — 1 $2,195,000

Soaring Sarasota Bay and Gulf of Mexico views from every room of this 8th floor residence at Grand Bay. This 2-bedroom + Den Biscayne floor plan is located on the corner ...

2 Beds
3.5 Baths
Grand Bay SubDv.
34228 Zip Code

2303 Harbour Oaks Drive, Longboat Key image

2303 Harbour Oaks Drive, Longboat Key $1,250,000

** Professional photography not yet complete but here are a few pics to make you want more** CRAFTED WITH CARE AND DETAIL TO MAKE IT THEIR OWN…….. BUT PLANS CHANGE! This...

3 Beds
2.5 Baths
Harbour Oaks SubDv.
34228 Zip Code

524 Schooner Lane, Longboat Key $4,850,000

Nestled in the heart of the Country Club Shores, you're about to uncover a coastal masterpiece that spans a generous 4,438 square feet. Built in 2008, this sumptuous 4-be...

4 Beds
4.5 Baths
Country Club Shores SubDv.
34228 Zip Code

360 Gulf Of Mexico Drive Unit 312, Longboat Key image

360 Gulf Of Mexico Drive Unit 312, Longboat Key — 3 $1,650,000

Welcome to Tangerine Bay Club! An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/d...

3 Beds
2.5 Baths
Tangerine Bay Club SubDv.
34228 Zip Code

530 Chipping Lane, Longboat Key $1,950,000

Fabulous Country Club Shores water-front lot. Ideal location, great deep-water boating, direct Bay and Gulf access, underground utilities, and brand new 100' seawall. F...

Country Club Shores SubDv.
34228 Zip Code

3808 Gulf Of Mexico Drive Unit 205E, Longboat Key image

3808 Gulf Of Mexico Drive Unit 205E, Longboat Key — E $387,000

This Meticulously maintained and updated 1 bedroom, 1 bath condo in Beach Harbor Club which comes fully furnished and priced to sell. Move in ready. There is a storage ar...

1 Beds
1 Baths
Beach Harbor Club SubDv.
34228 Zip Code

455 Longboat Club Road Unit 807, Longboat Key image

455 Longboat Club Road Unit 807, Longboat Key — Pierre $1,995,000

As you step into this eighth-floor haven at The Pierre, prepare to be captivated by the breathtaking Gulf-to-bay views. Tucked away behind the secure gates of the prestig...

3 Beds
3 Baths
Pierre SubDv.
34228 Zip Code

1485 Gulf Of Mexico Drive Unit 104, Longboat Key image

1485 Gulf Of Mexico Drive Unit 104, Longboat Key — 1485 $1,850,000

Welcome to Players Club on Longboat Key, S/W gulf views from the oversized balcony. 3 bedrooms, completely renovated with high quality, custom finishes in 2021/2022, incl...

3 Beds
3 Baths
Players Club SubDv.
34228 Zip Code

2675 Gulf Of Mexico Drive Unit 304, Longboat Key image

2675 Gulf Of Mexico Drive Unit 304, Longboat Key — 2676 $2,750,000

Welcome to this oceanfront paradise at Veinte! This condo offers the ultimate beachfront living experience with breathtaking panoramic unobstructed sunset views, direct b...

3 Beds
3 Baths
Veinte SubDv.
34228 Zip Code

100 Sands Point Road Unit 211, Longboat Key image

100 Sands Point Road Unit 211, Longboat Key — Sands Point $1,595,000

Your exceptional tropical escape awaits in Sands Point, a sought-after beachfront community within the gates of the Longboat Key Club and set on the gorgeous southern tip...

2 Beds
2 Baths
Sands Point SubDv.
34228 Zip Code

2364 Harbour Oaks Drive, Longboat Key image

2364 Harbour Oaks Drive, Longboat Key $1,200,000

Exceptional Opportunity Awaits! Experience Exclusive Coastal Luxury Living Welcome to a truly unique gem that offers an unparalleled coastal lifestyle. This magnificent ...

3 Beds
2.5 Baths
Harbour Oaks SubDv.
34228 Zip Code

2295 Gulf Of Mexico Drive Unit 83s, Longboat Key image

2295 Gulf Of Mexico Drive Unit 83s, Longboat Key — South $1,700,000

If you’ve ever dreamt of awakening to the sound of surf and forever views of the Gulf of Mexico out your windows, than you need to make this 8th floor condo your reality....

2 Beds
2 Baths
Islander Club Of Longboat SubDv.
34228 Zip Code

4325 Gulf Of Mexico Drive Unit 205, Longboat Key image

4325 Gulf Of Mexico Drive Unit 205, Longboat Key — 4325 $979,000

Enjoy spectacular sunsets from this beachfront condominium at Tiffany Plaza! This 2 BD/2 BA condo offers a spacious living/dining area, split floorplan with comfortably s...

2 Beds
2 Baths
Tiffany Plaza SubDv.
34228 Zip Code

549 Sloop Lane, Longboat Key $5,499,000

Welcome to the epitome of luxurious coastal living on Longboat Key Florida with this dream coastal oasis home! Nestled amidst the picturesque shores of Longboat Key thi...

4 Beds
3.5 Baths
Country Club Shores SubDv.
34228 Zip Code

380 N Shore Road Unit 6, Longboat Key image

380 N Shore Road Unit 6, Longboat Key — 380 $585,000

A rare opportunity to own a beautifully renovated waterfront weekly rental on the northern tip of Longboat Key! Choose when you want to use your own slice of paradise and...

1 Beds
1 Baths
Long Boat Pass Condominium SubDv.
34228 Zip Code

4900 Gulf Of Mexico Drive Unit PH5, Longboat Key image

4900 Gulf Of Mexico Drive Unit PH5, Longboat Key — 'B' $975,000

JAW-DROPPING! MULTI-MILLION $ WATER VIEWS! Step inside this 2-bedroom/2 bath Luxurious Penthouse Condo and instantly be captivated by the seamless fusion of elegance and ...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

1641 Harbor Cay Lane, Longboat Key image

1641 Harbor Cay Lane, Longboat Key $5,397,111

" short stories " ...Live Exquisite on the island of Longboat Key in Bay Isles Harbor Section, an active boating community of 67 architect-designed homes. The subject pro...

Harbour Links SubDv.
34228 Zip Code

597 Buttonwood Drive, Longboat Key image

597 Buttonwood Drive, Longboat Key $4,699,000

PreConstruction. Soon to grace Longboat Key, an exquisite coastal contemporary masterpiece by Brista Homes awaits, boasting a generous 4,176 square feet of luxurious livi...

5 Beds
5.5 Baths
Buttonwood Harbor SubDv.
34228 Zip Code

4540 Gulf Of Mexico Drive Unit 204, Longboat Key image

4540 Gulf Of Mexico Drive Unit 204, Longboat Key — F Building $650,000

Discover coastal living in this bright and airy two-bedroom, two-bathroom condo that has passed its milestone structural integrity inspection! Showcasing captivating view...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

597 Buttonwood Drive, Longboat Key $995,000

Indulge in the allure of your very own coastal paradise, as you uncover this exquisite .42-acre residential lot (lot 1A)—a sprawling canvas awaiting the masterpiece of yo...

Buttonwood Harbor SubDv.
34228 Zip Code

3240 Gulf Of Mexico Drive Unit B504, Longboat Key image

3240 Gulf Of Mexico Drive Unit B504, Longboat Key — Portobello 3240 $869,900

Beautifully remodeled furnished condo with gorgeous water view. Fifth floor unit is perfectly positioned for inviting morning light and full afternoon shade on the terra...

2 Beds
2 Baths
Portobello SubDv.
34228 Zip Code

651 Cedars Court, Longboat Key — 651 $695,000

Now is the time to seize the opportunity and purchase this exquisite turnkey furnished townhome in Cedars East Tennis & Fitness Resort on Longboat Key. Whether you're loo...

2 Beds
2 Baths
Cedars East SubDv.
34228 Zip Code

600 Dream Island Road, Longboat Key image

600 Dream Island Road, Longboat Key $4,250,000

We are proud to present this 1.06 Acre Property on a deep water canal with no bridges to the intercoastal waterway and 10 minutes to the Gulf of Mexico. Great opportunity...

3 Beds
2 Baths
Charlies Subdivision SubDv.
34228 Zip Code

1105 Gulf Of Mexico Drive Unit 404, Longboat Key image

1105 Gulf Of Mexico Drive Unit 404, Longboat Key — 5 $1,395,000

Nestled on the fourth floor, this beachfront Beachplace residence presents a true three-bedroom sanctuary. With the lush community grounds and the captivating Gulf of Mex...

3 Beds
2 Baths
Beachplace SubDv.
34228 Zip Code

591 Russell Street, Longboat Key $2,500,000

Beautiful home in a beautiful location on 2 lots. This classic cozy home in the beautiful longboat key area can be yours today. Immaculate landscaping in a massive yard g...

3 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

3806 Gulf Of Mexico Drive Unit C208, Longboat Key image

3806 Gulf Of Mexico Drive Unit C208, Longboat Key — C208 $399,000 ▼

We're pleased to present the opportunity to acquire a Rare gem property in a highly demanded Longboat Key, FL. Nested in an enjoyable neighborhood, and minutes from loca...

1 Beds
1 Baths
Beach Harbor Club SubDv.
34228 Zip Code

561 Gulf Bay Road, Longboat Key $1,200,000

When you’re looking TO BUILD on LONGBOAT KEY, this unique LOT is ready for construction. Property includes SURVEY and COMPLETED PLANS for a 3Bd/2Ba Pool Home designed by ...

Bailey-Dobson SubDv.
34228 Zip Code

605 Spanish Drive N, Longboat Key $585,000

Imagine a life where the beach is just a short distance away or perhaps a quick jaunt to the marina and pool. Welcome to the Spanish Main Yacht Club Condo on the illustri...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

3802 Gulf Of Mexico Drive Unit A107, Longboat Key image

3802 Gulf Of Mexico Drive Unit A107, Longboat Key — A $630,000

Welcome to this completely renovated 2 bedroom, 2 bath first floor corner unit at Beach Harbor Club. This is a true beach to bay community with all the amenities you coul...

2 Beds
2 Baths
Beach Harbor Club SubDv.
34228 Zip Code

4234 Gulf Of Mexico Drive Unit D2, Longboat Key image

4234 Gulf Of Mexico Drive Unit D2, Longboat Key — Pelican Harbour And Beach Club $799,000

Cherish the island life. Enjoy it all in this gorgeous custom renovated bayfront condominium in Pelican Harbour and Beach Club. A true beach-to-bay community with priva...

2 Beds
2 Baths
Pelican Harbour & Beach Club SubDv.
34228 Zip Code

2045 Gulf Of Mexico Drive Unit M1-402, Longboat Key image

2045 Gulf Of Mexico Drive Unit M1-402, Longboat Key — 2045 $649,000

Welcome to this bright and beautifully updated, tastefully furnished 2 bedroom, 2bath residence with an open kitchen outfitted for a chef, featuring granite counters, new...

2 Beds
2 Baths
Seaplace SubDv.
34228 Zip Code

5005 Gulf Of Mexico Drive Unit 3, Longboat Key image

5005 Gulf Of Mexico Drive Unit 3, Longboat Key $12,000,000

Unveiling the pinnacle of coastal living at this pristine beachfront residence at Bonaire Longboat Key. A newer gem completed in 2020, this luxurious home, offered turnke...

5 Beds
5.5 Baths
Bonaire At Longboat Key SubDv.
34228 Zip Code

2295 Gulf Of Mexico Drive Unit 112, Longboat Key image

2295 Gulf Of Mexico Drive Unit 112, Longboat Key $1,600,000 ▼

Live the Florida dream on your private, quiet, secluded crystal white beach at The Islander Club. Full views of the Gulf of Mexico and city lights including the Ringling ...

2 Beds
2 Baths
Islander Club Of Longboat SubDv.
34228 Zip Code

669 Spanish Drive N Unit 21, Longboat Key image

669 Spanish Drive N Unit 21, Longboat Key $425,000 ▼

Major Price Reduction for a quick sale! Calling all boaters. Are you looking for a lovely maintenance-free coastal community that lives like a single-family home? You may...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

565 Spanish Drive N, Longboat Key $445,000 ▼

Best of both worlds, boating and beach! This highly sought-after Longboat Key community, Spanish Main Yacht Club, offers an on-site deep-water marina accommodating up to ...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

420 Firehouse Court Unit 7, Longboat Key image

420 Firehouse Court Unit 7, Longboat Key $848,750

This is the only west side (beachside) of Gulf of Mexico villa for sale on Longboat Key. Walking distance to the beach and gulf. Walking distance to Whitney's and the Whi...

2 Beds
2 Baths
Faine Apartments A Condominium SubDv.
34228 Zip Code

2600 Harbourside Drive Unit R-5, Longboat Key image

2600 Harbourside Drive Unit R-5, Longboat Key $295,000

65 ft x 21 ft Boat Slip at Longboat Key Moorings Marina is for sale! The views from the slip are fantastic; located east side cul-de-sac. LBK Club membership required. Di...

Bay Isles SubDv.
34228 Zip Code

2800 Harbourside Drive Unit D-16, Longboat Key image

2800 Harbourside Drive Unit D-16, Longboat Key $450,000

A great 75 ft x 26 ft Boat Slip at Longboat Key Moorings Marina. Great location, easy in and out of the slip due to the large turning radius. LBK Club membership is optio...

Bay Isles SubDv.
34228 Zip Code

4700 Gulf Of Mexico Drive Unit 201, Longboat Key image

4700 Gulf Of Mexico Drive Unit 201, Longboat Key — D $1,125,000

This beautiful, spacious, fully furnished 1561 square foot 2 bedroom 2 full bath end unit condo was completely renovated down to the studs in 2022. EVERYTHING IS NEW! LE...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

4234 Gulf Of Mexico Drive Unit D1, Longboat Key image

4234 Gulf Of Mexico Drive Unit D1, Longboat Key — D $820,000 ▼

Experience the serenity of island living on Longboat Key in this newly renovated, ground floor walkout, Pelican Harbour bayfront condo. Have it all: gorgeous bayfront vi...

2 Beds
2 Baths
Pelican Harbour & Beach Club SubDv.
34228 Zip Code

6701 Gulf Of Mexico Drive Unit 331, Longboat Key image

6701 Gulf Of Mexico Drive Unit 331, Longboat Key — 6701 $1,150,000

Discover paradise within this Gulf front condominium that blends the lifestyle of a relaxed community with the luxury of a 5-star hotel. Tucked away within a serene and u...

2 Beds
2 Baths
Whitney Beach SubDv.
34228 Zip Code

1211 Gulf Of Mexico Drive Unit 802, Longboat Key image

1211 Gulf Of Mexico Drive Unit 802, Longboat Key — Promenade $1,995,000

Welcome to your dream beachfront retreat at The Promenade on the shores of Longboat Key’s pristine beaches. This sunny, south-facing eighth-floor residence offers an open...

3 Beds
3 Baths
Promenade SubDv.
34228 Zip Code

3040 Grand Bay Boulevard Unit 221, Longboat Key image

3040 Grand Bay Boulevard Unit 221, Longboat Key — Ii $2,495,000

Move right in! Enjoy this season in an updated, turnkey furnished 3 full bedrooms 3.5 bath residence highlighting sweeping Sarasota Bay and City views from every room. Th...

3 Beds
3.5 Baths
Grand Bay SubDv.
34228 Zip Code

2295 Gulf Of Mexico Drive Unit 25S, Longboat Key image

2295 Gulf Of Mexico Drive Unit 25S, Longboat Key — 25s $750,000

Rarely available Islander Club on the south end of Longboat Key. This is one of the few amazing units left in this area at a very competitive price point for the island....

2 Beds
2 Baths
Islander Club Of Longboat SubDv.
34228 Zip Code

500 Harbor Point Road, Longboat Key image

500 Harbor Point Road, Longboat Key $9,850,000

This spectacular custom home is situated in the exclusive Bay Isles Harbor sub-division behind security gates that are manned 24 hours. The home is on an oversized corner...

5 Beds
5.5 Baths
Bay Isles SubDv.
34228 Zip Code

3605 Fair Oaks Place, Longboat Key image

3605 Fair Oaks Place, Longboat Key $2,200,000

Set in the highly desirable Queens Harbour community located behind the Bay Isles gates in the Harbourside section of the Longboat Key Club, sits this picturesque 4 bedro...

4 Beds
3.5 Baths
Queens Harbour (F/K/A Manchester Bay) SubDv.
34228 Zip Code

1085 Gulf Of Mexico Drive Unit 101, Longboat Key image

1085 Gulf Of Mexico Drive Unit 101, Longboat Key — 11 $759,000

Live the Lifestyle You Deserve in this gated gulf front condo community. BEACHPLACE - located on the south end of esteemed Longboat Key, Florida! Rare opportunity to be ...

2 Beds
2 Baths
Beachplace SubDv.
34228 Zip Code

1955 Gulf Of Mexico Drive Unit G6-202, Longboat Key image

1955 Gulf Of Mexico Drive Unit G6-202, Longboat Key — 1955 $599,000 ▼

Looking for a vacation get-away, second home, investment property, or your permanent residence? This is might be the one! Second floor, 2BD/2BA "A" floor plan residence n...

2 Beds
2 Baths
Seaplace SubDv.
34228 Zip Code

7153 La Lenaire Drive, Longboat Key image

7153 La Lenaire Drive, Longboat Key $7,200,000

Pre-Construction. To be built. IMAGINE your own 1.26-acre lushly landscaped waterfront oasis on a private island! Your imagination can become reality on exquisite Jewf...

5 Beds
5.5 Baths
La Lenaire Isle SubDv.
34228 Zip Code

102 Twin Shores Boulevard, Longboat Key image

102 Twin Shores Boulevard, Longboat Key — 102 $449,000 ▼

BOATERS PARADISE FOUND! BOAT slips AVAILALBE! Rarely available FURNISHED/RENOVATED 2 Bedroom, 2 Bath concrete VILLA with BAY to BEACH access in active 55+ maintenance f...

2 Beds
2 Baths
Twin Shores Mobile Home SubDv.
34228 Zip Code

7094 Longboat Drive E, Longboat Key image

7094 Longboat Drive E, Longboat Key $2,990,000 ▼

Discover an unparalleled chance to own a truly unique property in the enchanting village of Longbeach on the esteemed North end of Longboat Key. This spectacular 11,252 s...

Long Beach SubDv.
34228 Zip Code

7094 Longboat Drive E, Longboat Key $2,990,000 ▼

Rare Opportunity to Embrace Historic Living in Longbeach Village, Longboat Key. Discover an unparalleled chance to own a truly unique property in the enchanting village o...

3 Beds
2.5 Baths
Long Beach SubDv.
34228 Zip Code

4540 Gulf Of Mexico Drive Unit 201, Longboat Key image

4540 Gulf Of Mexico Drive Unit 201, Longboat Key — 'F' $795,201

NATURE’S DREAM HOME! LONGBOAT KEY! This Beautiful and Spacious 1561 square foot 2-bedroom, 2-bath corner deluxe end unit condo, offers a peaceful retreat for nature lover...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

545 Sanctuary Drive Unit B406, Longboat Key image

545 Sanctuary Drive Unit B406, Longboat Key — Building 3 $2,475,000

Welcome to luxury living at The Sanctuary behind the gates of the Longboat Key Club on south Longboat Key! Whether you're looking for a peaceful retreat or a permanent re...

3 Beds
2.5 Baths
Sanctuary SubDv.
34228 Zip Code

2525 Gulf Of Mexico Drive Unit 6B, Longboat Key image

2525 Gulf Of Mexico Drive Unit 6B, Longboat Key — Islands West $1,695,000

Fully-remodeled, move-in ready, ultra-luxury beach residence on Longboat Key. Over-the-top upgrades include Cucine Ricci European cabinetry, quartz countertops, marble fl...

2 Beds
2 Baths
Islands West SubDv.
34228 Zip Code

2600 Harbourside Drive Unit I-12, Longboat Key image

2600 Harbourside Drive Unit I-12, Longboat Key $220,000

A 45 ft x 21 ft Boat Slip is available at Longboat Key Moorings Marina. The only north/south pier in the marina! Direct access to Sarasota Bay and the ICW. The purchase...

Bay Isles SubDv.
34228 Zip Code

793 Jungle Queen Way, Longboat Key image

793 Jungle Queen Way, Longboat Key $2,250,000 ▼

This charming, canal front Key West Style home has four generous bedrooms and three baths and is located mid Longboat Key on a quiet street on a 150’ Wide lot with mature...

4 Beds
3.5 Baths
Longboat Key SubDv.
34228 Zip Code

3060 Grand Bay Blvd. Unit 126, Longboat Key image

3060 Grand Bay Blvd. Unit 126, Longboat Key — 3060 $2,399,000 ▼

Discover an exquisite lifestyle with stunning southeast views spanning the vibrant city skyline and sparkling Sarasota Bay from this residence in sought-after Grand Bay o...

3 Beds
3.5 Baths
Grand Bay SubDv.
34228 Zip Code

621 Hibiscus Way, Longboat Key $865,000

Build your dream home on this idyllic 7200 sf lot in the most desirable part of Longboat Key, the Historic village. This northern location off Broadway puts you walking d...

Long Beach SubDv.
34228 Zip Code

100 Sands Point Road Unit 113, Longboat Key image

100 Sands Point Road Unit 113, Longboat Key — Sands Point $2,850,000

RARE opportunity to own this LEGACY property. The same family purchased this property from the developer and has held it in the family for 50 years. This building was c...

4 Beds
3 Baths
Sands Point SubDv.
34228 Zip Code

210 Sands Point Road Unit 2304, Longboat Key image

210 Sands Point Road Unit 2304, Longboat Key — 2 $1,050,000

Enjoy direct views of the Gulf of Mexico and tangerine sunsets along with a healthy income from this completely renovated, west facing, turnkey furnished Junior Suite at ...

1 Beds
1 Baths
Inn On The Beach SubDv.
34228 Zip Code

656 Tarawitt Drive, Longboat Key $998,900

Spectacular opportunity to build your dream home on this 10,800 SF canal front lot with optimal southern exposure and 120’ of water frontage located on the north end of L...

Longboat Key SubDv.
34228 Zip Code

598 Lyons Lane, Longboat Key $3,499,000

This stunning, 2021 new custom estate home is nestled on one of the canal lots on the exclusive near north end of Longboat Key. Built by Mason Martin builders, this proje...

3 Beds
3.5 Baths
Sleepy Lagoon SubDv.
34228 Zip Code

545 Sanctuary Drive Unit B206, Longboat Key image

545 Sanctuary Drive Unit B206, Longboat Key — 545 $2,200,000 ▼

Welcome to a lifestyle that surpasses all expectations in the Sanctuary community, where luxury living meets breathtaking views! Nestled on the 2nd flr, this 3BR, 3BA con...

3 Beds
3 Baths
Sanctuary SubDv.
34228 Zip Code

5265 Gulf Of Mexico Drive Unit 304, Longboat Key image

5265 Gulf Of Mexico Drive Unit 304, Longboat Key — Na $1,200,000

Gulf to Bay community of 44 units, pets welcome, incredible Gulf views. This 3 bedroom condo has high vaulted ceiling and has lots of closet space. Owner improvements inc...

3 Beds
3 Baths
Banyan Bay SubDv.
34228 Zip Code

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Testimonials

Lisa Salvato - 5 stars! John is fabulous! He listened to what we wanted and emailed us only properties that applied. We live in New York and were interested in purchasing a Florida property. Having never met him prior to our visit to view the key properties of interest, from his e-mails, we didn't know what to expect . We feel like we hit the jackpot, John was professional, courteous and went out of his way to show us condos in a spread-out area. We have now closed on that purchase. Thank-you John for being a great negotiator and knowledgeable in your field. Your follow-through beyond the closing is appreciated and impressive. Thank-you Leslie for your work in the background to follow-up with all of the condo documents. We have sold and purchased homes before and John is at the top! February 2018

Robert Theofel — Above and beyond! Every aspect of the home buying process from initial search to closing went without a hitch due to Leslie and John’s expertise. When searching for a home, we received recommendations that were within our search criteria and the team was always available to show the homes that we selected. The recommendations we received during the negotiating, buying and closing process were excellent and we were able to close within a month of the initial viewing of the property. I would highly recommend them to anyone looking to buy a home!

Curt Johnson — My wife and I needed to sell our house, however there was much to do to get it ready. John and Leslie let us know how to fix-up the house to get the best possible response at the showings. We got it done and sold our house within 2 days of listing it with them. I think one of the best things I walked away with from the experience is how I felt trusting them with my home knowing that they had my best interest at hand. I would recommend John and Leslie to anyone who wants to be successful in selling or buying a home.

Jennifer Pearson — Leslie and John went above and beyond to help us sell our home! We had relocated 1900 miles away as we were trying to sell our house. They were in constant contact with us regarding the house and showings. They helped us find maintenance people when needed and even completed some things themselves. We would highly recommend them and should we return to the area, we will definitely use them to purchase a home!

Valerie Bologna — 5 stars! John helped my husband and I find a condo in Sarasota while we are living in another state. If there was something that we were interested in, he would go out right away and take pictures of the place and e-mail them to us. He never made us feel like we were wasting his time even though our purchase was not a million dollar listing! In a few years we will be calling on John again to find us a permanent place to live instead of seasonally. My husband and I appreciate all that he and his wife Leslie have done for us to make this purchase go as smooth as possible and we feel like we have gained new friends as well!

Victoria Harlow — 5 stars! Leslie went above and beyond with advice on staging, open houses, and cleaning and caring for my property while I was absent. Her teammate and husband John make a stellar team. I was so happy to get a great offer so close to my asking price. Awesome work! Thank-you for being vigilant and for the awesome care you took with selling my house. Your are the best that I've encountered after selling three houses over the years!

Edy Campos — 5 stars! - Can't get any better than John! He helped me all the way until the end, gives great advice, works fast, follows up and doesn't waste time. If you are serious about finding a place to call "home", I really recommend John Gregory!

Nancy Gallagher — If you're looking for a new home in Florida, John is a tireless agent to have on your side! If he doesn't know the answer to a question (which is rare) he will find it and in a timely manner! I highly recommend his services.

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Longboat Key Real Estate Search

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