Longboat Key, FL Homes

/53
$895,000 Pending
- 3 Beds
- 3 Baths
- 2,608 Sq Ft
3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228

This stunning three-bedroom, three-bath villa offers a serene waterfront retreat in the desirable Winding Oaks community of Longboat Key Club. With a spacious open floor plan spanning 2,608 Sf, the maintenance-free home is bathed in natural light and features vaulted ceilings that enhance its airy feel. The inviting living/dining room combo seamlessly connects to a screened-in back deck, perfect

Julie Klick

MICHAEL SAUNDERS & COMPANY

(941) 206-8039

3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228
/57
$9,500 per month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
519 Bayport Way Unit 519, Longboat Key, FL 34228

Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both directions for miles along the Gulf of Mexico shore. The complex includes a large pool surrounded by flowering trees, four immaculately maintained clay tennis courts, fitness center, a large clubhouse,

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 273-0449

519 Bayport Way Unit 519, Longboat Key, FL 34228
/2
$64,000 Sold Oct 30, 2025
- 0 Days On Market
408 Gulf of Mexico Dr Unit 2210, Longboat Key, FL 34228

Protect your boat from the harsh SW Florida Elements in your personal Dry Stack Slip #2210 in the coveted Boat House on Longboat Key. Call the office when you are ready for a day of boating and they will remove your cover and have the boat in the water ready for your adventures. When you return they will hose your boat down, flush the engines, put the cover on and put it back in your Hurricane

Sean Clark MICHAEL SAUNDERS & COMPANY

408 Gulf of Mexico Dr Unit 2210, Longboat Key, FL 34228

/20
Not Listed For Sale
- Studio
2600 Harbourside Dr Unit C-2324, Longboat Key, FL 34228

2600 Harbourside Dr Unit C-2324, Longboat Key, FL 34228

/84
$985,000 Pending
- 3 Beds
- 3 Baths
- 2,381 Sq Ft
2358 Harbour Oaks Dr, Longboat Key, FL 34228

Under contract-accepting backup offers. This expansive villa offers the space and comfort of a private home, paired with the ease of maintenance-free living in Harbour Circle. Vaulted ceilings, oversized rooms, and natural light define the interior, while nearly 760 square feet of outdoor living—including a double-deck lanai overlooking a saltwater pond fed by the bay—create the perfect backdrop

Rachel Tritschler

RE/MAX ALLIANCE GROUP

(941) 239-3436

2358 Harbour Oaks Dr, Longboat Key, FL 34228
/68
$10,000 per month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
720 Bayport Way Unit 720, Longboat Key, FL 34228

Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical setting with a spacious eat-in kitchen that is open to the living area. Elegantly furnished in a natural color pallet. The master suite is tastefully decorated, with a built in vanity, double sinks and his and her closets. It also features a small alcove with a desk with access

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 206-3379

720 Bayport Way Unit 720, Longboat Key, FL 34228
/2
$530,000 Sold Oct 29, 2025
- 1,479 Sq Ft
- $358/SF
- 169 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
3540 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

Spellbinding Sunrises, Sunsets, and magical water views from this nicely updated Bayfront Beauty in an ideal Mid-Key Bay to Beach setting can be yours now. Delight in the panoramic Bay to Gulf views from the moment you wake up until you turn in after a fun-filled day at the private beach, or after taking your boat, kayaks or paddleboards out to explore paradise. The spacious patio is the perfect

Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

3540 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

/30
Est $1,043,204 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,172 Sq Ft
1125 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

1125 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

/53
$289,900 Pending
- 2 Beds
- 2 Baths
- 800 Sq Ft
3740 Gulf of Mexico Dr Unit 5-A, Longboat Key, FL 34228

Longboat Key Living! Enjoy the private beach directly across the street! 2 bedroom 2 bath home located in Twin Shores Beach & Marina Community. Island life is waiting for you. This home offers updated granite counters in the kitchen, 2 updated bathrooms and ample living space. The living/ Dining room combo is large enough to entertain your friends, family and neighbors. Enjoy some of the best

Jill Young

CENTURY 21 INTEGRA

(941) 206-5844

3740 Gulf of Mexico Dr Unit 5-A, Longboat Key, FL 34228
/60
$9,500 per month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
744 Bayport Way Unit 744, Longboat Key, FL 34228

Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fully furnished and equipped with flat screen TV's, cable and WiFi. This residence features a spacious screened lanai with garden views in addition to an outdoor sun deck with loungers for basking in the sun. Bayport sits on 27 lushly landscaped acres and has 1200

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 294-6846

744 Bayport Way Unit 744, Longboat Key, FL 34228
/2
$600,000 Sold Oct 29, 2025
- Land
- 0.14 Acre
- $4,285,714 per Acre
- 185 Days On Market
2929 Pyrula Dr, Longboat Key, FL 34228

Build your dream home on this exceptional vacant lot located in the heart of Longboat Key. Nestled midway on the island, this rare offering includes deeded beach access just a short stroll away, allowing you to enjoy the pristine Gulf shores at your leisure. Perfectly positioned for both privacy and convenience, the property is just moments from the upscale shopping and dining of St. Armands

Zain Hartman HARTMAN REAL ESTATE & COMPANY

2929 Pyrula Dr, Longboat Key, FL 34228

/69
Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,470 Sq Ft
3750 Gulf of Mexico Dr, Longboat Key, FL 34228

3750 Gulf of Mexico Dr, Longboat Key, FL 34228

/37
$799,000
- Land
- 0.15 Acre
- $5,326,667 per Acre
766 Saint Judes Dr N, Longboat Key, FL 34228

Prime CANAL lot on beautiful Long Boat Key. l with 2 new working boat lifts installed in 2023 (10,000lb capacity & 13,000lb capacity)! Ready to be built on - lot has been cleared. New 100' sea wall installed in 2022. Deeded beach access to the gulf as well. Perfect location near amazing restaurants and beautiful beaches.

Nikki Spirakis

BRG REAL ESTATE INC

(941) 688-9189

766 Saint Judes Dr N, Longboat Key, FL 34228
/54
$9,500 per month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
517 Bayport Way Unit 517, Longboat Key, FL 34228

Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 325-0092

517 Bayport Way Unit 517, Longboat Key, FL 34228
/2
$535,000 Sold Oct 29, 2025
- 1,248 Sq Ft
- $429/SF
- 168 Days On Market
- 2 Beds
- 2 Baths
- Built 1965
640 Fox St, Longboat Key, FL 34228

Price improvement! Here is a buyer's opportunity to create your vision and enjoy a unique coastal lifestyle in the sought-after historic Longbeach Village on Longboat Key’s north end. The concrete block home has an open living area, two expanded bedrooms, two baths with a lanai and a one-car garage. The home sits on spacious corner lot with mature shade trees in this great neighborhood with no

Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

640 Fox St, Longboat Key, FL 34228

/97
Est $1,140,382 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,358 Sq Ft
2101 Gulf of Mexico Dr Unit 2501, Longboat Key, FL 34228

2101 Gulf of Mexico Dr Unit 2501, Longboat Key, FL 34228

/70
$649,000
- 2 Beds
- 2 Baths
- 1,072 Sq Ft
4350 Chatham Dr Unit 307, Longboat Key, FL 34228

Luxury Coastal Living at Longboat Harbour: Experience stunning canal views and modern elegance in this impeccably renovated 3rd-floor condo, ideally situated in the desirable all-age community of Longboat Harbour. Offered turnkey furnished, this beautifully curated residence is ready for your immediate enjoyment, whether you're seeking a winter retreat or full-time coastal living. Step inside

Marsha Winegarden

WAGNER REALTY

(941) 239-6809

4350 Chatham Dr Unit 307, Longboat Key, FL 34228
/58
$9,000 per month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
829 Bayport Way Unit 829 B, Longboat Key, FL 34228

Introducing a remarkable opportunity to rent a piece of paradise at 829 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. As you enter the community, you are greeted by meticulously landscaped grounds that set the

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 239-2327

829 Bayport Way Unit 829 B, Longboat Key, FL 34228
/2
$810,000 Sold Oct 29, 2025
- 1,427 Sq Ft
- $568/SF
- 239 Days On Market
- 3 Beds
- 3 Baths
- Built 1964
600 Fox St, Longboat Key, FL 34228

Experience the charm of historic Longboat Key living in this delightful 3-bedroom, 3-bathroom single-family home – Coastal Haven Cottage! Nestled in the heart of the village, you're just a short stroll away from pristine Gulf beaches and the area's renowned waterfront restaurants. Enjoy the convenience of golf cart access throughout the village and a quick ride over the bridge to explore the

Lindsey Leech Strickland DUNCAN REAL ESTATE, INC.

600 Fox St, Longboat Key, FL 34228

/57
Est $4,443,351 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,319 Sq Ft
4995 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

4995 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

/76
$695,000 Open Sun 1PM - 3PM
- 2 Beds
- 2 Baths
- 1,312 Sq Ft
4540 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views. Every detail has been thoughtfully updated ,this home has been renovated from top to bottom, featuring new flooring, new plumbing, new electrical, new lighting, hurricane-impact windows with shutters for peace of mind

Paulina Vasiliev

KELLER WILLIAMS ON THE WATER S

(941) 759-9957

4540 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
/40
$9,000 per month
- 2 Beds
- 2 Baths
- 1,514 Sq Ft
- Condo for Rent
615 Dream Island Place Unit 201, Longboat Key, FL 34228

Picturesque Water view of Sarasota Bay . The Harbour Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boatramp, kayak launch/storage, 3 tennis courts, covered parking and 400' of boat slips and bayfront. Features include over 1500 sq ft of livingspace in this end unit, high ceilings, Waterview available in all rooms, open floor plan, large enclosed balcony

William Glade

WILLIAM GLADE LIC. REAL ESTATE BROKER

(941) 279-2178

615 Dream Island Place Unit 201, Longboat Key, FL 34228
/2
$1,215,000 Sold Oct 28, 2025
- 1,508 Sq Ft
- $806/SF
- 128 Days On Market
- 3 Beds
- 3 Baths
- Built 1970
791 Saint Judes Dr N, Longboat Key, FL 34228

Rarely is there a renovation that starts below the foundation (all sewer drain lines with new PVC), to the 2-year-old metal roof. Top to bottom, that's right roof, windows, electrical, water lines, HVAC, flooring insulation all new ductwork. The shellcrete exterior concrete (front yard, side yard leading to one dock and both driveways) as well as the pool deck, that's right all shellcreted. These

Bruce Meyer MICHAEL SAUNDERS & COMPANY

791 Saint Judes Dr N, Longboat Key, FL 34228

/88
Est $675,705 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,453 Sq Ft
5260 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

5260 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

/59
$2,100,000
- 2 Beds
- 2 Baths
- 1,485 Sq Ft
2295 Gulf of Mexico Dr Unit 83S, Longboat Key, FL 34228

Imagine waking up each morning to the gentle sound of waves and a breathtaking view of the Gulf from every room in your home. This stunning 2-bedroom, 2-bathroom residence offers just that, with a 35-foot lanai that perfectly frames the spectacular scenery. Recently remodeled, this home embodies luxury, comfort, and style. The interior of this residence is nothing short of remarkable. Light-toned

Peter Ingrasselino

DEAL HOUSE REALTY LLC

(941) 274-4734

2295 Gulf of Mexico Dr Unit 83S, Longboat Key, FL 34228
/30
$7,750 per month
- 3 Beds
- 3 Baths
- 1,672 Sq Ft
- Condo for Rent
5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

William Glade

WILLIAM GLADE LIC. REAL ESTATE BROKER

(941) 207-4034

5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
/2
$1,560,000 Sold Oct 28, 2025
- 2,462 Sq Ft
- $634/SF
- 185 Days On Market
- 3 Beds
- 3 Baths
- Built 1984
2020 Harbourside Dr Unit 454, Longboat Key, FL 34228

An incredible opportunity to own a rarly redone to the highest stanard condo. Now available sought after top floor three bedroom condo offering almost 2500, sq. ft. of living space. The special feature of this condo is the amazing unobstructed views of Sarasota Bay and downtown Sarasota plus views of the beach and the Gulf of Mexico from the kitchen. This very spacious Bay front condominium has

Reid Murphy DEVELOPERS REALTY LBK, INC

2020 Harbourside Dr Unit 454, Longboat Key, FL 34228

/56
Est $369,569 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,007 Sq Ft
3804 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

3804 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

/57
$1,250,000
- 2 Beds
- 2 Baths
- 1,395 Sq Ft
726 Jungle Queen Way, Longboat Key, FL 34228

Waterfront Paradise on Longboat Key – Deeded Beach Access + Private Pool + Private Dock! Welcome to your dream coastal retreat! This fully renovated 2 bedroom, 2 bath canal-front home on Longboat Key is the ultimate blend of luxury, comfort, and convenience. Nestled just steps from 10 miles of pristine Gulf beaches—with deeded beach access—you’ll enjoy the best of both water worlds: boat out

Brooke O'Malley

CLUB REALTY

(941) 882-9192

726 Jungle Queen Way, Longboat Key, FL 34228
/81
$13,000 per month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
806 Bayport Way Unit 806, Longboat Key, FL 34228

Discover a tranquil retreat at 806 Bayport Way, where coastal living meets sophisticated design. This exceptional property is ideally located near a private beach, providing residents with exclusive access to sun-soaked shores and beautiful ocean views.Upon entering, you’ll be greeted by a thoughtfully designed space that emphasizes both comfort and functionality. The kitchen features

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 390-2885

806 Bayport Way Unit 806, Longboat Key, FL 34228
/2
$917,000 Sold Oct 27, 2025
- 2,905 Sq Ft
- $316/SF
- 25 Days On Market
- 3 Beds
- 3 Baths
- Built 1968
749 Penfield St, Longboat Key, FL 34228

An extraordinary opportunity awaits the next visionary owner of this spacious waterfront Mediterranean-style home. Whether you choose to renovate the current home or build your new dream home, it is ideally located on a wide canal with no fixed bridges to the Gulf of Mexico. A day out on the water is right out of your back door! It is just a short stroll to the pristine beach in the highly

JoDene Moneuse MICHAEL SAUNDERS & COMPANY

749 Penfield St, Longboat Key, FL 34228

/24
Est $1,025,008 Not Listed For Sale
628 Lyons Ln, Longboat Key, FL 34228

628 Lyons Ln, Longboat Key, FL 34228

/38
$1,370,000
- Land
- 0.41 Acre
- $3,341,463 per Acre
560 Gulf Bay Rd, Longboat Key, FL 34228

RARE DOUBLE-SIZED ESTATE LOT ON LONGBOAT KEY – 18,000 SQ FT OF ISLAND LUXURY READY FOR YOUR VISION. Opportunities like this are few and far between. Nestled in one of the most coveted areas of Longboat Key, this expansive 18,000-square-foot estate lot at 560 Gulf Bay Road offers a blank canvas for your dream coastal retreat—just steps from the sugar-white sands of the Gulf of Mexico. Perfectly

Gregory Claxton

PREFERRED SHORE LLC

(941) 352-8416

560 Gulf Bay Rd, Longboat Key, FL 34228
/79
$13,000 per month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
609 Bayport Way Unit 609, Longboat Key, FL 34228

ELEGANTLY PRESENTED! This bright and spacious property located just steps away from a private deeded beach is perfect for those who appreciate easy access to sun and sand. This residence boasts modern features and well-thought-out design, making it an ideal retreat for relaxation and comfort.The living area is characterized by an open layout that seamlessly connects to the kitchen,

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 214-7905

609 Bayport Way Unit 609, Longboat Key, FL 34228
/2
$1,550,000 Sold Oct 24, 2025
- 1,823 Sq Ft
- $850/SF
- 18 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1990
575 Sanctuary Dr Unit A302, Longboat Key, FL 34228

Renovated in 2023 and perfectly positioned on the 3rd floor, this 2BR/2.5BA residence at The Sanctuary offers a refined retreat where sweeping views and timeless design come together. Wood plank tile flooring runs throughout, while high-impact glass frames the vibrant greens of the Links golf course and the shimmering waters beyond. Neutral tones set an elegant backdrop, allowing the natural

Bruce Myer COLDWELL BANKER REALTY

575 Sanctuary Dr Unit A302, Longboat Key, FL 34228

/53
Est $864,321 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,172 Sq Ft
1085 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

1085 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

/6
$649,000
- Land
- 0.14 Acre
- $4,635,714 per Acre
6981 Lois Ave, Longboat Key, FL 34228

LOCATION ALERT!!! Build your dream home on this 6,000 sq ft vacant residential lot. This spacious lot offers a creative, vast playground of architectural possibilities and also those famous and coveted gorgeous, Gulf sunsets and sunrises. You are located in the heart of The Village in Longboat Key, convenient walking distance to fabulous restaurants like The Shore, Mar Vista and Whitney's. The

Jason Sato

SATO REAL ESTATE INC.

(941) 763-6831

6981 Lois Ave, Longboat Key, FL 34228
/34
$7,000 per month
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
- Condo for Rent
737 Bayport Way Unit D, Longboat Key, FL 34228

BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two

Marianne LeBar

ROSEBAY INTERNATIONAL REALTY, INC

(941) 946-6594

737 Bayport Way Unit D, Longboat Key, FL 34228
/2
$595,000 Sold Oct 24, 2025
- 624 Sq Ft
- $954/SF
- 41 Days On Market
- 1 Bed
- 1 Bath
- Built 1977
5155 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

Direct Beachfront Gem! Wake up to the sound of waves and breathtaking Gulf views from this beautifully updated one bedroom, one bath condo located directly on the beach! Whether you're seeking a serene getaway, an investment property or a full-time coastal retreat, this condo offers the perfect blend of comfort, style and location. This end unit is a bright and airy open floor

Kathryn Cooper COLDWELL BANKER REALTY

5155 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

/17
Est $198,328 Not Listed For Sale
- Studio
- 800 Sq Ft
2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228

2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228

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