My Active Listings

Some or all of the listings below are provided by the Longboat Key office.
$999,999 (USD)
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Sarasota Area Single Family Home

Active

2518 Dick Wilson Drive Sarasota, FL 34240

3 Bed
3 Baths
3023 sqft
MLS# A4672995
Virtual Tour
With its thoughtful layout, open-concept interiors, and seamless indoor-outdoor flow, this 3 bedroom, 3 bathroom home effortlessly combines luxury, function, and privacy — all within a captivating courtyard setting surrounded by over 3000 sf of living space. It is perfect for those who love to entertain thanks to its triple split floorplan and large common spaces. The moment you enter, you’re greeted by the serene centerpiece of the home — a sparkling heated pool and spa, outdoor kitchen with vented gas grill, and shaded al fresco dining space. The main house showcases soaring ceilings with crown molding, while French doors and transom windows flood the interiors with natural light. A sunroom in the back functions as a perfect playroom for little ones, or as an inspiring office, art studio, or library. The guest suite is thoughtfully designed with a custom Murphy bed and library shelves, and is ideal offering the independence and comfort of a true guest house within the property’s secluded courtyard embrace. ** The property offers peace of mind, inside and out, as it has a brand new AC and water heaters, was recently re-plumbed, and has a 2017 barrel tile roof. It has been beautifully maintained, with a recently updated pool heater and pump and a brand new well for irrigation. The oversized two-car garage with golf cart space includes a large air-conditioned storage room, is EV charging ready with a 40amp wall outlet, and there is additional parking space for all the guests who will be clamoring to come visit! ** Enjoy care-free living as this enclave of Laurel Oak includes lawn maintenance in your HOA fees. Laurel Oak Estates offers a lifestyle of distinction, featuring a 24 hour guarded gate and stunning manicured grounds. Membership to the club is optional, and has its privileges: 36 holes of championship golf, 12 tennis courts, 6 pickleball courts, a clubhouse that offers dining and social events, and an inviting heated and cooled junior Olympic pool. Live the Florida lifestyle you’ve been dreaming of, in the home and neighborhood that will make you feel like you’ve arrived!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Alison Stottlemyer
$999,000 (USD)
Active

Sarasota Area Single Family Home

Active

7031 Scrub Jay Drive Sarasota, FL 34241

4 Bed
3 Baths
3586 sqft
MLS# A4668056
Virtual Tour
Serenity, sophistication, and sweeping lakefront views converge in this exceptional estate, located within the prestigious gated community of Red Hawk Reserve. Set on a premium homesite and thoughtfully crafted for both elegant living and effortless entertaining, this 3,586 sq. ft. residence offers four bedrooms, three bathrooms, a dedicated office, a flexible studio or fifth bedroom, and an expansive 400+ sq. ft. bonus room. From the moment you step inside, you're welcomed by soaring ceilings, abundant natural light, and timeless architectural details that create a sense of openness and grandeur. At the heart of the home lies a gourmet kitchen, beautifully appointed with designer cabinetry, a custom wood range hood, granite countertops, under-cabinet lighting, a center island with breakfast bar, and high-end stainless steel appliances. Adjacent to the kitchen, a cozy dinette framed by a sweeping aquarium window offers the perfect setting to enjoy your morning coffee while overlooking the pool and tranquil lake. The primary suite is a private retreat, complete with serene views, dual custom walk-in closets with upgraded built-ins, and a spa-inspired en-suite bath featuring a Roman shower, soaking tub, and separate vanities. Step outside to your resort-style oasis—an expansive wrap-around lanai with brick pavers, a heated pool and spa, and lush tropical landscaping, all set against the backdrop of shimmering lake views. An oversized three-car garage offers generous built-in storage and overhead racks. At the same time, the community provides added peace of mind with a virtual guard gate, high-resolution security, and reclaimed water irrigation. Located within an A-rated school district and just minutes from the world-renowned Siesta Key Beach, this remarkable residence embodies the essence of Florida luxury living.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Skrzypkowski
$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
$995,000 (USD)
Active

Longboat Key Area Condominium

Active

5311 Gulf Of Mexico Drive 3 Longboat Key, FL 34228

2 Bed
2 Baths
1028 sqft
MLS# A4672601
Virtual Tour
Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance. Averaging six figures in annual gross income, this two-bedroom retreat is ideal for personal enjoyment, weekly rentals, or a combination of both—making it one of Longboat Key’s strongest investment opportunities.
The light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a well-appointed kitchen with granite countertops, contemporary cabinetry, modern appliances, and plumbing and electrical upgrades completed in 2006. Designed for effortless coastal living, the open layout seamlessly connects the kitchen, dining, and living areas. Floor-to-ceiling sliders lead to a private patio and screened-in lanai, both just steps from the beach, allowing indoor and outdoor spaces to flow together naturally.
The split-bedroom plan enhances privacy for owners and guests. The primary suite enjoys beautiful Gulf views, private patio access, and a peaceful setting perfect for morning coffee or sunset unwinding. A comfortable second bedroom and full bath complete the guest wing.
Beach Castle Resort is one of the few communities on Longboat Key offering daily, weekly, or monthly rental flexibility, giving owners the freedom to maximize both personal use and rental income. The community’s beach-to-bay amenities include deeded beach access, a sundeck with heated swimming pool and spa, barbecue grilling areas, a fishing pier, and a day dock for boating enthusiasts (first-come basis, no overnight docking). Lush tropical landscaping and well-maintained grounds create a relaxing boutique-resort environment.
Perfectly located on the north end of Longboat Key, the property is minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic walking and biking routes. A short drive south leads to the Longboat Key Club, upscale dining, and the attractions of St. Armands Circle. Downtown Sarasota—home to world-class theater, museums, botanical gardens, professional events, and waterfront parks—is just across the bridge.
With direct Gulf-front views, strong rental history, and an unbeatable location, this Beach Castle residence offers the best of Longboat Key’s coastal lifestyle—whether you’re seeking an investment, a getaway, or both.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$985,000 (USD)
Active

Sarasota Area Single Family Home

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3795 Eagle Hammock Drive Sarasota, FL 34240

3 Bed
3 Baths
2767 sqft
MLS# A4671537
Virtual Tour
This exquisite custom home, crafted by Tivoli Homes and built in 2014, sits gracefully behind the gates of The Hammocks—a community known for its manicured landscaping, brick-paved driveways, timeless tile roofs, and generously sized homesites. This home has customized landscaping both in front and in the back garden area. Inside, thoughtful upgrades bring warmth and elegance to every corner. Crown molding highlights the formal spaces, while tray ceilings add depth and character to the master suite, living room, and dining room. The gourmet kitchen is a true centerpiece: granite counters, a center island, rich cabinetry with soft-close features, top-tier appliances, a gas cooktop with pot filler, and a custom hood and backsplash—all coming together to create a space that’s as functional as it is beautiful. The master suite offers peaceful views of the pool and the nature preserve beyond, giving the room a sense of quiet retreat. The en-suite bath features dual granite vanities with abundant storage, a separate garden tub, a walk-in shower, and two custom walk-in closets designed to keep everything effortlessly organized. A versatile Den/Library features rich wood-look luxury vinyl planking—an ideal spot for work, reading, or overflow guest space. Two other guest bedrooms have the same luxury vinyl planking and custom closets. Three sets of glass doors open to an outdoor living area designed for year-round enjoyment. The custom saltwater heated pool and spa include a swim shelf and an awning with lighting that elevates the entertainment area, giving ample shade when needed. The outdoor kitchen—with its built-in grill and bar—anchors the extended paver lanai, creating an inviting space for gatherings large or small. Exterior painted in 2024, and the crowning touch is the air-conditioned garage with custom cabinetry. All of this is just a short drive from UTC Mall, multiple golf courses, and the area’s renowned beaches, as well as Rothenbach Park—making The Hammocks a perfect blend of serenity and convenience. There are many upgrades the seller has made to this property, feature sheet is available.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe
$975,000 (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
$950,000 (USD)
Active

Sarasota Area Land

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7676 Midnight Pass Road Sarasota, FL 34242

Bed
0 Baths
sqft
MLS# A4669790
An extraordinary opportunity awaits to create your own private waterfront oasis on world-renowned Siesta Key. Located at 7676 Midnight Pass Road, this expansive 0.43-acre cleared and level lot offers the ideal canvas for a custom coastal retreat that embodies tranquility, luxury, and the essence of island living.

Positioned along the serene waters of Heron Lagoon, the property features approximately 111 feet of peaceful, protected waterfront—perfect for designing your own dock for kayaking, paddleboarding, or simply enjoying the beautiful views of the lagoon. The setting is quiet, secluded, and immersed in natural beauty, delivering a true sense of sanctuary.

All just moments away from the dazzling white sands of Siesta Key Beach, consistently ranked the #1 beach in the United States for its powder-soft quartz sand, vibrant turquoise waters, and breathtaking sunsets. Here, you are close enough to stroll or bike to the shoreline yet tucked away in your own world of serene waterfront living.

The lot is cleared, spacious, and ready to build, with utilities already available—offering a seamless start to designing your dream coastal estate without the delays of demolition or site preparation.

This is truly a rare chance to craft your own slice of paradise on one of Florida’s most coveted barrier islands. Do not miss the opportunity to transform this exceptional property into the Siesta Key retreat you’ve always imagined.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Mairead Smialek
$950,000 (USD)
Active

Sarasota Area Single Family Home

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5557 Long Shore Loop Sarasota, FL 34238

3 Bed
2 Baths
2298 sqft
MLS# A4674783
Virtual Tour
This Stunning Home and “Amenity Rich” Gated Community checks off every box!
** FORMER MODEL ** Stunning & Spacious 2,298 sf Pool/Spa Home Features: 3 Bedrooms, 2 Baths and a 2 Car Garage and is literally ACROSS THE STREET from PICKLEBALL, CLUBHOUSE, FITNESS CENTER, RESORT POOL/SPA, BOCCE BALL & TENNIS in the highly sought-after Gated Maintenance-Free community of Sunrise Preserve at Palmer Ranch. This former Model Home features Casual & Contemporary ELEGANCE combined w/ endless Upgrades and truly epitomizes the Florida Lifestyle with PRIVACY - a Charming Pond and Mature Trees are your back yard! But it gets even better: the sellers are offering buyers the OPTION: to buy unfurnished OR to purchase Some or a Majority of the Designer Furnishings / Decor ala carte on a separate contract. Whether Full-Time or Part-Time residency is in your future, you will FALL IN LOVE w/ Sunrise Preserve AND this barely lived-in Model Home. You'll feel welcomed by a spacious entry with timeless finishes into a stunningly beautiful & modern home. Ask your realtor or the listing agent for the Summary of Upgrades & Features List. Built by Mattamy Homes, this Dayspring model has more than $240k in structural & design upgrades!! Including: high level porcelain tile flooring, high level cabinetry, tray/coffered ceilings with crown molding, 8' doors, High-End GOURMET / CHEF'S Kitchen with ALL Top-Of-The-Line KITCHENAID Appliances, stunning quartz countertops, gas cooktop, double ovens, 42' kitchen cabinets, Smart Home ready, surround sound, upgraded fixtures & ceiling fans, recessed lighting throughout, and much more! The Owner's Suite provides ample space and is well-appointed with a Large and Luxurious En-Suite Bathroom with Dual/Separate Vanities; an exquisite, oversized Shower; a private water closet AND His & Hers Walk-In Closets. But perhaps the BEST part of this home is bringing the Indoors OUT and the Outdoors IN! Situated East/West, you'll enjoy the morning Sunrise from your spacious front porch - AND Stunning Sunsets from the exceptional Caged Pool/Spa/Lanai offering the feeling of being pampered & relaxed - with a serene and private backdrop of a charming pond & mature trees, you'll enjoy nature to the fullest! FEEL CONFIDENT with ZERO storm damage: a base elevation of 21+ feet above sea level, block construction, hurricane shutters, AND the house/structure is designated to be Flood Zone X - Peace of Mind! There is NO CDD fee and Sunrise Preserve's low HOA fee provides complete community and owner landscaping AND the many Resort-Style Amenities: Clubhouse, Fitness Center, Pool, Spa, Pickleball, Tennis, Bocce Ball, Gathering Room, BBQ area, and More! The Sunrise Preserve neighborhood is also Large Pet-Friendly and is located in one of the BEST small cities: Sarasota, FL - where just part of the allure is World Class Siesta Key Beach, Numerous Outdoor & Water Activities, a wide variety of Cultural and Performing Arts & Entertainment... plenty of Shopping, Dining, Boating, Fishing, Live Music, Farmer's Markets, Golf, Kayaking - as well as Airports, Mote Marine, Benderson Rowing - and not too far for a trip to Disney World or to catch a Cruise Ship out of Tampa Bay. This Neighborhood and former Model home will stand OUT and ABOVE the rest!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Janine Kloiber