Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$600,000 (USD)
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Sarasota Area Single Family Home

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5113 Flagstone Drive Sarasota, FL 34238

3 Bed
2 Baths
1822 sqft
MLS# A4684602
Virtual Tour
Brand NEW ROOF (2025) offers peace of mind and potential insurance savings in this beautifully maintained lakeside home in The Hamptons in Palmer Ranch!

Lakeside luxury living awaits in this 3-bedroom, 2-bath single-family home located in one of Palmer Ranch’s most desirable communities. The HOA includes weekly lawn and landscaping maintenance, allowing for easy, carefree living.

Enjoy serene panoramic lake and preserve views from the exceptionally private screened lanai (new in 2025), the perfect place to relax or entertain while taking in the peaceful natural surroundings.

Inside, the open-concept living area provides an inviting space for gathering, while the desirable split floor plan offers privacy for family members and guests. The home features updated ceramic plank flooring throughout the living areas, bedrooms, and closets, creating a cohesive and modern feel.

The spacious primary suite offers a large walk-in closet and an ensuite bathroom complete with dual vanities, a Roman soaking tub, separate shower, and private water closet.

Bedrooms two and three share a well-appointed guest bathroom.

The open kitchen features recently upgraded appliances and a gas stove, ideal for the home chef who enjoys preparing meals while staying connected to family and guests.

A separate laundry room with washer and dryer, (New in 2024) leads to the spacious 2-car garage, which includes additional storage cabinets.

Additional highlights include:
• Brand New Roof (2025)
• Metal hurricane shutters and specialty storm blinds
• Re-plumbed with Uponor PEX piping (2017)
• New Washer/Dryer (2024)
• New Lanai screened in cage with no-seeum screen

Residents of The Hamptons enjoy access to a resort-style heated community pool, located just a short walk from the home.

Ideally located in Palmer Ranch, just minutes to the world-famous beaches of Siesta Key and close to the Legacy Trail, shopping, dining, and Sarasota’s vibrant arts and cultural scene.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Sheryl Van Duren
$599,000 (USD)
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Longboat Key Area Townhome

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847 Evergreen Way Longboat Key, FL 34228

2 Bed
3 Baths
1440 sqft
MLS# A4665172
Refined Coastal Living with Proven Income Potential – Experience the best of Longboat Key in this impeccably appointed, turnkey furnished residence within the coveted Cedars East Tennis Resort. This elegant 2BR/2.5BA townhome spans 1,440 square feet of thoughtfully curated living space, where tasteful coastal design meets modern comfort. The gourmet kitchen is adorned with granite surfaces and flows seamlessly into a bright, open living area designed for effortless entertaining. A tranquil, private lanai invites you to unwind amid lush tropical surroundings. The primary suite serves as a serene retreat, complete with dual vanities and a spa-inspired ambiance, while upstairs laundry enhances everyday ease. With a strong history of rental performance, this property offers a rare opportunity to blend lifestyle with investment. Residents and guests enjoy an array of resort-caliber amenities, including championship Har-Tru tennis courts, a heated Olympic-style pool, fitness center, and exclusive bayfront features such as a kayak launch, fishing pier, and scenic mangrove boardwalks. An on-site dining option adds to the effortless luxury. Ideally located just moments from the beautiful beaches of Longboat Key, the boutiques and dining of St. Armands Circle, downtown Sarasota, and Anna Maria Island.
A distinctive offering for the discerning buyer seeking both coastal elegance and exceptional return on investment.
No flood damage | New A/C (2025)
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Christine "Kiki" Bowers
$599,000 (USD)
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Longboat Key Area Condominium

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2301 Gulf Of Mexico Drive 25N Longboat Key, FL 34228

2 Bed
2 Baths
1235 sqft
MLS# A4667153
Virtual Tour
This inviting residence at the Islander Club of Longboat Key offers a peaceful retreat with beautiful views of the landscaped grounds. Spanning 1,235 sq ft, the home features two bedrooms, two full bathrooms, and an open floor plan that provides a comfortable space for both living and entertaining. The spacious kitchen and dining area offer plenty of room for cooking and gathering, with ample cabinetry and an open flow that makes the space perfect for hosting. The 38-foot private balcony, accessible from both the living room and bedrooms, offers a tranquil spot to enjoy the coastal breeze and the surrounding scenery. The primary suite serves as a peaceful retreat with an en-suite bathroom and a walk-in closet, while the guest bedroom, located next to the second full bathroom, ensures comfort and privacy. Additional features include a private covered parking space and secure storage. Situated in the heart of Longboat Key, this residence is conveniently located near waterfront dining, shopping, golf, and a short drive to St. Armands Circle and downtown Sarasota. The Islander Club offers a range of resort-style amenities, including 800 feet of private beach frontage, two Har-Tru tennis courts, a renovated community room with a full kitchen, billiards, table tennis, a library, fitness center and a heated pool. This is a wonderful opportunity to enjoy Longboat Key living in a residence that provides both comfort and ample space.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Bruce Myer
$599,000 (USD)
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Longboat Key Area Condominium

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1930 Harbourside Drive 122 Longboat Key, FL 34228

2 Bed
2 Baths
1192 sqft
MLS# A4692494
Virtual Tour
Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day.

Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle.

The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests.

The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style.

Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity.

Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches.

Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape.

This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / David Leventhal
$599,000 (USD)
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Sarasota Area Single Family Home

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2374 Arlington Street Sarasota, FL 34239

3 Bed
2 Baths
1126 sqft
MLS# A4680088
Virtual Tour
One or more photo(s) has been virtually staged. Located in Sarasota’s highly sought-after Arlington Park neighborhood, this thoughtfully updated residence delivers a compelling combination of comfort, functionality, and proximity to the city’s most popular destinations. With a renovated three-bedroom layout, the home is move-in ready and ideally positioned just minutes from downtown Sarasota and the area’s renowned Gulf beaches.
The interior features an open-concept design that connects the living, dining, and kitchen areas, creating an easy flow for everyday living and entertaining. Luxury vinyl plank flooring extends throughout the main living spaces, while freshly painted walls in a neutral color palette enhance the light-filled atmosphere. Two updated bathrooms provide modern convenience and a cohesive finish.
The kitchen serves as the heart of the home, offering granite countertops, a full-height tile backsplash, ample cabinetry, and a central island that adds workspace and casual seating. Sliding doors open to a spacious, fully fenced backyard—an inviting outdoor setting with room to relax, garden, or create a customized outdoor retreat. Additional exterior storage adds everyday practicality.
Residents enjoy immediate access to Arlington Park, known for its playground, fountains, walking paths, picnic areas, basketball courts, and tennis facilities—just moments from the front door. The nearby Southside Village offers popular dining spots, local boutiques, and everyday conveniences, while downtown Sarasota’s arts, dining, and waterfront attractions are only a short drive away.
World-famous beaches including Siesta Key Beach and Lido Key are easily accessible, providing endless opportunities for coastal recreation. This Arlington Park home offers an ideal balance of neighborhood charm, city convenience, and access to Sarasota’s best lifestyle amenities.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Roger Pettingell
$599,000 (USD)
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Bradenton Area Condominium

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3608 54th Drive W 202 Bradenton, FL 34210

3 Bed
3 Baths
1981 sqft
MLS# A4679378
Virtual Tour
Located within the gated Bollettieri Villas at IMG Academy, this spacious villa offers an exceptional opportunity to own one of Bradenton’s most convenient & private locations—just steps from IMG Academy’s East Campus tennis and basketball facilities and minutes from beaches, shopping, dining, and SRQ Airport. Spanning 1,981 square feet, the home features three bedrooms, three full bathrooms, plus a versatile bonus room that can easily function as a 4th bedroom, home office, gym, or study. Cathedral ceilings throughout much of the home create an open, airy feel, while plantation shutters and large windows provide natural light and tranquil preserve views, offering both privacy and a peaceful setting. There is additional flex space off the living room giving owners the opportunity to utilize as a formal dining space or as additional living space.
The residence has been thoughtfully maintained and partially updated, while also presenting a strong value with opportunity for future cosmetic upgrades, allowing a buyer to personalize the space and build immediate equity. The primary suite sits on its own wing of the property and includes an ensuite bathroom with soaking tub, walk-in shower, and quality finishes. Two bedrooms with shared full bathroom sit on the opposite wing of the home from the master creating additional privacy for all. The kitchen includes extended counterspace overlooking the spacious living room, a breakfast nook, and a dedicated walk-in pantry. The property includes its own laundry room in unit with a sink cabinet. There is an additional storage closet just off the outdoor front porch. The HVAC system is equipped with humidistat and ultraviolet purification to support air quality.
A private, gated front balcony provides a quiet outdoor retreat, ideal for morning coffee or relaxing evenings. A brand-new canvas awning with a metal frame will add the rare benefit of three covered parking spaces, a standout feature within the community.
Residents enjoy access to a heated community pool, spa, and fitness room, along with walkable proximity and golf-cart access throughout IMG Academy. The community allows one-month minimum rentals, making this property well-suited for long-term rental investment, seasonal use, or owner occupancy—a flexible option in a high-demand area driven by IMG Academy and nearby amenities.
Just a short drive to grocery stores, UTC Mall, downtown Sarasota, and the Gulf beaches, this villa offers an ideal blend of location, space, investment potential, and long-term value. (One or more of these photo(s) have been virtually staged)
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Matthew Huffman
$599,000 (USD)
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Longboat Key Area Condominium

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1932 Harbourside Drive 242 Longboat Key, FL 34228

2 Bed
2 Baths
1192 sqft
MLS# A4688978
Virtual Tour
Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Ryan Ackerman
$599,000 (USD)
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Sarasota Area Condominium

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800 S Blvd Of The Presidents 19 Sarasota, FL 34236

2 Bed
2 Baths
1090 sqft
MLS# A4675312
Virtual Tour
Experience the perfect blend of modern design and an unbeatable location in this meticulously renovated 2-bedroom, 2-bathroom, 2-story townhome at Embassy Villas on Lido Key. Just two blocks from the pristine sands of Lido Beach and a short stroll to the shops and dining options of St. Armands Circle, this home offers both convenience and style. Spanning over 1,090 sq. ft., this residence feels exceptionally spacious thanks to its soaring ceilings, large windows, and sleek contemporary exterior. Natural light pours in from every direction, highlighting the airy, open layout and creating a bright, welcoming atmosphere throughout. Inside, the living space is designed for both beauty and functionality. The stylish galley kitchen features all-white cabinetry, engineered stone countertops, a modern tile backsplash, stainless steel appliances, dual sinks, and under-cabinet lighting, all accented by a breakfast bar that opens to the main living area. The first-floor primary suite offers a serene retreat, surrounded by windows for an abundance of natural light, and includes a chic en suite bath with dual vanities and contemporary finishes. Upstairs, the loft-style second bedroom provides a private getaway with striking angles, abundant light, and its own well-appointed en suite bath. Embassy Villas is a boutique community offering relaxed living in one of the Suncoast’s most desirable, walkable areas. Residents enjoy easy access to the public heated pool at Lido Beach, and the home’s generous rental policy allows for two-week minimum stays up to 26 times per year. Pets are welcome, with a limit of two (up to 20 lbs. each). This townhome is an ideal seasonal retreat, full-time residence, or investment property.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Bruce Myer