My Active Listings

Some or all of the listings below are provided by the Longboat Key office.
$1,095,000 (USD)
Active

Longboat Key Area Condominium

Active

1000 Longboat Club Road 402 Longboat Key, FL 34228

2 Bed
2 Baths
1290 sqft
MLS# A4670053
Virtual Tour
Coastal Elegance at Privateer South, Longboat Key!
Set directly along the Gulf of Mexico, this beautifully renovated two-bedroom residence at Privateer South offers effortless beachfront living within the gates of the prestigious Longboat Key Club. Move-in ready, every detail of this turnkey fourth-floor getaway speaks to comfort, style, and sophistication, framed by sweeping Gulf views and warm coastal light.
Porcelain tile floors extend throughout, creating a seamless flow from room to room, while all-impact glass sliders and windows frame tranquil vistas and ensure peace of mind. The open-concept great room is spacious yet inviting, with defined living and dining areas that connect effortlessly to one of two private terraces—perfect for morning coffee or evening sunsets over the water.
The modern kitchen features solid wood, shaker style cabinetry (unified throughout the home), sleek granite countertops, stainless-steel appliances, wine refrigerator, and breakfast bar seating, offering the perfect blend of beauty and function. Built-in shelving adds both storage and architectural character, while subtle lighting and window treatments complete the refined aesthetic.
The primary suite serves as a private retreat with direct terrace access, a generous wall-to-wall custom-built closet, and a revamped en-suite bathroom featuring dual vanities, granite counters, and a spacious shower with multiple heads. The second bedroom is thoughtfully designed to function as a stylish office or guest suite, complete with a walk-in closet and custom Murphy bed concealed behind clean cabinetry—ideal for flexible use of space. A second full bath with tub/shower combination is equally well-appointed.
Two terraces—overlooking the shimmering Gulf and eastern sunrise views—extend the living experience outdoors. The residence also includes an assigned covered parking space, the convenience of interior laundry, and abundant storage throughout.
Privateer South is one of Longboat Key’s premier beachfront communities, offering resort-style amenities in a serene and secure setting. Residents enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, fitness center, and clubhouse, all surrounded by lush tropical landscaping with direct access to one of Florida’s most pristine stretches of sand. Association fees include cable, water, waste collection, grounds care, and 24-hour gated security for a truly maintenance-free lifestyle.
Perfectly positioned within the Longboat Key Club gates, the location allows members to enjoy world-class golf, a full-service marina, and exceptional dining just moments away (membership options available separately). A short drive brings you to St. Armands Circle for boutique shopping and fine restaurants, or over the bridge to downtown Sarasota, where theater, art, and culture thrive.
Offering a rare combination of coastal tranquility, thoughtful design, and resort-style living, Privateer South #402 captures the best of Gulf-front Sarasota living—an inspired residence where every day feels like a retreat.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$1,090,000 (USD)
Active

Sarasota Area Condominium

Active

101 Benjamin Franklin Drive 63 Sarasota, FL 34236

2 Bed
2 Baths
1275 sqft
MLS# A4668335
Virtual Tour
Experience stunning, unobstructed views of the Gulf from this 2-bedroom, 2-bath condo located directly on the beach in highly sought-after Lido Key. Just a short walk to world-famous St. Armands Circle, you'll enjoy easy access to upscale shopping, dining, and entertainment—all while living steps from the sand and surf. This fully furnished, move-in-ready residence offers 1,275 sq ft of light-filled living space, with breathtaking water views from every room. Neutral tile flooring flows throughout, creating a clean, coastal feel. Step out onto your private 240 sq ft balcony to soak in nightly sunsets and the soothing sound of waves—there’s plenty of room for dining or lounging in style. Inside, enjoy the convenience of electric shades, ample closet space, and a separate storage locker located right in front of your assigned parking space. Hurricane shutters provide added peace of mind, and yes—your small pet (up to 25 lbs) is welcome too! The building has undergone significant renovations including updates to the lobby, community spaces, kitchen, library, gym, bathrooms, plumbing re-lining, and resurfaced heated pool. On-site maintenance management adds another layer of ease to your beachside lifestyle—and best of all, the building is fully funded. Live just minutes from Lido Beach's Tiki Bar and Pavilion, or explore the nearby nature preserve with kayaking, paddleboarding, and fishing. Downtown Sarasota—with its vibrant arts scene, fine dining, and cultural venues—is just a short drive away via the Ringling Bridge. This is more than a condo—it’s your gateway to the ultimate coastal lifestyle. Schedule your showing today and own a front-row seat to the Gulf of Mexico.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Nathalie Nolander
$1,074,000 (USD)
Active

Longboat Key Area Condominium

Active

5311 Gulf Of Mexico Drive 3 Longboat Key, FL 34228

2 Bed
2 Baths
1028 sqft
MLS# A4635657
Virtual Tour
Turnkey furnished and ready to enjoy or rent, this charming beachfront retreat on Longboat Key offers the perfect blend of coastal living and investment potential. Situated directly on the pristine shores of the Gulf of Mexico, this two-bedroom residence grosses an average of six figures in annual rental income, making it an exceptional opportunity for personal enjoyment or weekly rentals. Set within Beach Castle Resort, this first-floor, direct Gulf-front property boasts breathtaking water views and effortless beach access just steps from the outdoor entertaining spaces. Inside, the light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a granite kitchen with modern cabinetry, appliances, and upgraded plumbing and electrical systems (2006). The open-concept layout seamlessly connects the kitchen, living, and dining areas, with sliders leading to an inviting patio and a screened-in space ideal for relaxation. The two-bedroom split layout ensures privacy for guests. The primary suite enjoys private patio access and serene Gulf views, creating a peaceful retreat for owners and visitors alike. Beach Castle Resort is one of the rare Longboat Key communities offering flexible daily, weekly, or monthly rental programs. Residents and guests appreciate the beach-to-bay amenities, including deeded beach access, barbecue grilling areas, a sundeck with a heated swimming pool and spa, a fishing pier, and a day dock for boating enthusiasts (no overnight docking, first-come basis). The north end of Longboat Key offers a relaxed, tropical lifestyle. Bayfront Park and Cedars Tennis Resort are minutes away, while the southern end of the island brings the liveliness of the Longboat Key Club, fine dining, boutique shopping at St. Armands Circle, and the cultural attractions of downtown Sarasota. This beachfront retreat is an ideal escape, combining Gulf-front tranquility with exceptional rental income potential.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$1,025,000 (USD)
Active

Sarasota Area Single Family Home

Active

795 Plymouth Street Sarasota, FL 34242

4 Bed
3 Baths
1967 sqft
MLS# A4661729
Virtual Tour
Welcome to your slice of paradise on Siesta Key. This beautifully updated 4-bedroom home offers the perfect blend of coastal charm and modern comfort, nestled on a peaceful, tree-lined street in one of the island’s most sought-after neighborhoods. Step inside to discover a bright, airy interior filled with natural light, where spacious living areas flow effortlessly into a large open-air pool, ideal for relaxing afternoons or entertaining under the sun. The heart of the home is designed for easy Florida living, with a thoughtful layout that invites connection and calm. The primary suite features a generous walk-in closet and a calming, private ambiance, perfect for unwinding after a day in the sun. Recent upgrades include a new roof installed in 2021 and a high-efficiency HVAC system from 2020, offering peace of mind and year-round comfort. Outside, the hardscaped, low-maintenance yard adds tropical appeal without the upkeep, while the paver driveway enhances curb appeal with a touch of elegance. Whether you're hosting poolside gatherings or enjoying quiet mornings with coffee and birdsong, this home delivers the kind of lifestyle that feels like vacation every day. And with Siesta Beach just minutes away, you’ll have world-class sand and surf practically at your doorstep. Move-in ready and lovingly maintained, this property is more than a home, it’s a serene escape in the heart of paradise. Did not flood during 2024 storms.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Courtney Church
$1,000,000 (USD)
Active

Sarasota Area Single Family Home

Active

221 Island Circle Sarasota, FL 34242

3 Bed
2 Baths
1159 sqft
MLS# A4668472
Virtual Tour
Experience the best of island living in this beautifully maintained Turnkey FULLY FURNISHED, Key West-style home just moments from Siesta Key Public Beach and the vibrant Siesta Village. Offering 3 bedrooms, 2 bathrooms, and a 2-car garage with brand-new doors, this residence has been thoughtfully updated over the years with major recent improvements including a 2023 metal roof and all-new impact glass windows and doors for peace of mind. Head upstairs to the main living level where an open-concept layout welcomes you with luxury vinyl plank flooring, vaulted ceilings, and plantation shutters that fill the space with natural light. The kitchen features stainless steel appliances only a few years old, granite countertops, and a convenient connection to the dining area—ideal for hosting friends and family. Each bedroom showcases plantation shutters and crown molding for added charm. The primary suite is a true retreat, complete with a walk-in closet with built-in organization, an ensuite bathroom with a glass-enclosed shower tucked behind a stylish barn door, and direct access to the backyard deck through sliding glass doors. The two guest bedrooms share a tastefully updated full bathroom. Step outside to the elevated deck overlooking the private backyard, where a cozy fire pit area awaits in the corner—perfect for evening conversations and coastal breezes. An outdoor shower is the perfect spot to rinse off after a long day at the beach. Whether you’re seeking a full-time residence or the ideal vacation getaway, the flexibility of no HOA allows you to live as you please. Located just down the road from the powdery white sands of world-renowned Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home delivers the quintessential Siesta Key lifestyle.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Kaisen Mitchell
$995,000 (USD)
Pending

Longboat Key Area Condominium

Pending

1000 Longboat Club Road 1103 Longboat Key, FL 34228

2 Bed
2 Baths
1409 sqft
MLS# A4662719
Virtual Tour
Perched atop the 11th floor, this penthouse residence at Privateer South captures an extraordinary sweep of views spanning Longboat Key Club’s lush golf course, the expanse of Sarasota Bay, the downtown skyline, and the Gulf of Mexico’s turquoise waves. Offering more than 1,400 square feet, the light-filled interiors flow effortlessly between living, dining, and kitchen spaces, framed by impact windows and glass sliders that open to two private terraces—one Gulf-facing and one Bay-facing—inviting you to enjoy sunrises and sunsets alike. The modernized kitchen balances style and function with quartz countertops, a sleek tile backsplash, shaker cabinetry, and stainless-steel appliances. Porcelain tile flooring adds a timeless touch, enhancing the airy ambiance throughout. The split-bedroom plan ensures privacy when guests visit, with the primary suite offering direct access to the larger terrace, a spacious walk-in closet, and a private en-suite bath, while the guest suite is positioned on the opposite wing with its own serene views. Additional comforts include newer impact-rated windows and sliders, covered parking, and an owner’s storage unit located on the same floor. Privateer South, set directly on the Gulf of Mexico, has recently been enhanced with upgrades that further elevate its appeal, including a newer roof, refreshed lobby, and updated common areas. Residents enjoy a lifestyle that blends leisure and convenience, with a beachside heated pool and spa on an expansive deck, tennis, pickleball, and shuffleboard courts, fitness center, fire pit lounge, barbecue area with outdoor seating, social room with catering kitchen, and guest suites for visitors. On-site management and security provide peace of mind in this sought-after community. Beyond the gates, Longboat Key delivers a lifestyle defined by natural beauty and cultural access. Championship golf and fine dining await for members at the Longboat Key Club, while the boutiques and restaurants of St. Armands Circle are minutes away. Downtown Sarasota, with its world-class theaters, museums, galleries, and vibrant waterfront, is an easy drive south. Award-winning beaches, including those of neighboring Lido and Siesta Key, complete the picture, offering endless opportunities to explore, relax, and savor life on the Gulf Coast. This penthouse is more than a residence—it’s a front-row seat to the very best of Sarasota living.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$959,000 (USD)
Active

Osprey Area Single Family Home

Active

238 Lookout Point Drive Osprey, FL 34229

3 Bed
3 Baths
2676 sqft
MLS# A4650720
Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impeccably maintained residence offers an enviable lifestyle for those who cherish the water. The journey begins at the inviting brick paver entry, guiding you into a gracious foyer that sets the tone for the home's elegant charm. Upon entering, you are welcomed by a spacious great room featuring new tile flooring and a wall of sliding glass doors that seamlessly connect to the expansive covered lanai. The open floor plan is perfect for entertaining, with a dining area adjacent to the sophisticated kitchen equipped with 42” cabinets, stone countertops, stainless steel appliances, a breakfast bar, and easy access to the grilling area. Relax in the enormous owner’s retreat, thoughtfully secluded for privacy. This luxurious space boasts an ensuite bathroom with dual sinks and a free-standing shower, offering a serene sanctuary for unwinding after a day on the water. The home's layout includes two additional guest suites, providing comfort and privacy for visitors. A separate den with a wood-burning fireplace adds a cozy touch, creating a perfect spot for relaxation or reading. The outdoors are effortlessly integrated with the interior, featuring a lavish 12x60 screened lanai that is ideal for alfresco dining or simply enjoying the serene surroundings. Recent improvements, including newer plumbing throughout, a 2021 roof, and new screened lanai cage, make this home truly maintenance-free. Southbay Yacht & Racquet Club offers a variety of amenities designed to enhance your active lifestyle. The community-owned deep-water marina provides boat slips that accommodate large vessels, ensuring easy access for your nautical adventures. The club features lighted tennis courts, a heated community pool, an exercise room, a playground, and numerous clubs and social activities, catering to diverse interests. While the community is beautifully balanced with nature and the Bayfront, you'll still be minutes away from a plethora of fantastic restaurants, shopping destinations, and the pristine Casey Key beach. This sought-after location ensures that you can enjoy the best of both worlds—tranquility and convenience. Southbay Yacht & Racquet Club embodies the perfect blend of luxury and natural beauty, offering a unique opportunity to live an active lifestyle centered around the water. Whether you're an avid boater, a tennis enthusiast, or someone who simply loves the charm of coastal living, this community has something extraordinary to offer.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Stephanie Church
$957,000 (USD)
Active

Sarasota Area Single Family Home

Active

2021 Misty Sunrise Trail Sarasota, FL 34240

5 Bed
4 Baths
3182 sqft
MLS# A4667841
Virtual Tour
Nestled beneath a lush canopy of majestic oaks and palms, this exceptional residence embodies a lifestyle that seamlessly blends the timeless charm of Old Florida with the contemporary comforts of a newer home. Located in the highly desirable Sylvan Lea community of Sarasota, the property sits on a picturesque, tree-lined street where neighbors enjoy leisurely strolls, and breathtaking sunrises greet you each morning. Step inside to discover a meticulously designed and pristinely maintained two-story home featuring 5 bedrooms, 4 bathrooms, and versatile spaces which could be used for a virtual office or an expansive workout room—perfectly suited for modern living. The heart of the home is the inviting great room, enhanced by a trey ceiling and effortless access to the gourmet kitchen. Here, stone countertops, a generous island, stainless steel appliances and abundant white cabinetry create an ideal setting for both casual family meals and sophisticated entertainment. The main floor offers true convenience and privacy with a split plan offering three spacious guest rooms. Escape to the lavishly spacious primary suite, featuring a spa-inspired bathroom with dual vanities, a custom-tiled shower, separate soaking tub, and a private water closet. Enjoy abundant storage in the expansive walk-in closet. The full laundry room located on the main floor adds practicality and ease to daily routines. Upstairs, a fifth bedroom and bonus area with a full bathroom offer a private retreat—perfect for guests or in-laws seeking their own space to relax and unwind. Step outside to embrace the Florida lifestyle on the expansive screened brick paver patio, featuring a private, heated pool—your personal oasis for evening gatherings or peaceful relaxation. The fully fenced backyard creates wonderful space, allowing your four-legged family members to roam safely and freely. A spacious three-car garage completes the home, providing ample storage and convenience. With whole home hurricane protection, a brand-new roof and fresh interior and exterior paint, this home offers true maintenance-free living. Sylvan Lea presents a rare Sarasota experience with peaceful, canopy streets that feel secluded, yet you’re just minutes from I-75, downtown Sarasota, and the world-renowned white-sand beaches of Siesta Key. Enjoy the perfect blend of convenience and tranquility in this remarkable home.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Stephanie Church
$951,288 (USD)
Sold

Sarasota Area Single Family Home

Sold

10177 Silent Night Lane Sarasota, FL 34241

4 Bed
3 Baths
3004 sqft
Sold Data Entry Only - New Construction
Listing Courtesy of STELLAR / Stellar Non-Member Office
$949,000 (USD)
Active

Sarasota Area Single Family Home

Active

7426 Weeping Willow Boulevard Sarasota, FL 34241

3 Bed
3 Baths
3276 sqft
MLS# A4656257
Virtual Tour
**SIGNIFICANT PRICE REDUCTION** Luxury just became more attainable - recent price adjustment makes this home an unbeatable value! Welcome to a peaceful paradise in the sought-after Woodlands of Bent Tree! This lovely 3-bedroom, 3-bathroom residence is perfectly situated on a sprawling waterfront homesite and showcases pride of ownership from the moment you arrive. With thoughtful design and meticulous maintenance, this property embodies the quintessential Florida lifestyle while offering wide scenic lake views from most rooms.
A spacious and inviting master suite features two large custom walk-in closets and a master bath with updated cabinetry and quartz counters, ensuring both luxury and practicality. Each generously sized guest bedroom offers glass sliders leading to lush garden views, creating a serene retreat for family or guests. A true office space with double frosted-glass doors provides the perfect environment for working from home or managing personal affairs. An additional bonus space can serve as another office or fitness room.
The heart of the home is the expansive kitchen which boasts upgraded cabinetry, granite countertops, and a sleek pass-through to the lanai, complete with a built-in buffet and outdoor refrigerator. The kitchen blends with ease to the large family room, with soaring ceilings, a stunning coral-surround wood-burning fireplace, and walls of glass doors, seamlessly connects to the lanai, perfect for entertaining.
Disappearing sliding glass doors allow for effortless indoor-outdoor living, showcasing the home's sunny southern exposure and natural light from multiple skylights.
The resurfaced sparkling pool is generously sized for lap swimming and surrounded by a spacious brick pavered lanai with ample undercover seating.
Enjoy the tranquil lake views while entertaining guests or savoring quiet moments in the lush, landscaped setting.
Additional Highlights include a brand new roof offering peace of mind for years to come, a 3-car side-entry garage, with the 3rd bay air-conditioned, provides extensive storage and workshop options. The long driveway includes a generous turnaround pad making entering or exiting the garage a breeze.
An exceptional amount of thoughtful storage systems and closets throughout the home ensure organization and convenience. For your comfort a gasoline-powered portable house generator and water filtration system are included.
This pristine home has been lovingly maintained by its long-time owner, and it’s ready for you to make it your own. Don't miss the opportunity to experience luxurious waterfront living in the established community of The Woodlands of Bent Tree. Schedule your private showing today and discover the perfect blending of comfort, elegance, and natural beauty.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Kelly Rosenberg

Coldwell Banker - Longboat Key

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