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$2,499,000
5 Beds ⋅ 6 Baths ⋅ Monticello SubDv. ⋅ 34231 Zip Code
EXCEPTIONAL CUSTOM LUXURY HOME ON COQUINA ISLAND! One-of-a-kind 5BR/5.5BA custom residence offering 4,000+ SF of luxurious and enjoyable modern coastal living on an exceptional homesite. The open, flexible floor plan features a dramatic great room with 13' ceilings, floor-to-ceiling windows, custom open staircases, and beautiful wood and tile flooring. The gourmet chef's kitchen boasts premium appliances, oversized island, double wall ovens, coffee bar, and expansive walk-in pantry. Main-level primary suite features two custom walk-in closets and luxurious ensuite bath. Multiple private decks and a spacious paver lanai overlook the heated PebbleTec saltwater pool and spillover spa. Designed for effortless entertaining, the resort-style outdoor living area includes an outdoor kitchen with marine-grade cabinetry, tropical landscaping, and professionally designed hardscape. A separate living space with private entrance includes its own great room, full kitchen, bedroom, bathroom, laundry room, and private balcony—ideal for extended family, guests, a private retreat, or other lifestyle needs. Additional highlights include a 38' wide polyaspartic garage with lift potential, three HVAC systems/zones, sound insulation, extensive structured wiring, 19 speakers, eight security cameras, indoor/outdoor Wi-Fi mesh, custom storage, private irrigation well, and LED-lit circular paver driveway. Located on desirable Coquina Island, close to Siesta Key Beach, Phillippi Mansion Park, Sarasota Memorial Hospital, downtown Sarasota, Selby Gardens, shopping, and dining. Exceptional architectural design, luxury amenities, flexible living spaces, and outstanding indoor-outdoor living—all offered below estimated replacement cost.

2110 Michele Drive, Sarasota
$5,650,000
4 Beds ⋅ 5 Baths ⋅ Aqualane Estates SubDv. ⋅ 34231 Zip Code
Some homes are built. Others are envisioned. 1516 Ridgewood is the result of an uncompromising pursuit of excellence—a California Pacific Palisades-inspired waterfront estate where timeless architecture, extraordinary craftsmanship, and Sarasota's coveted boating lifestyle converge into one remarkable residence. Completely reimagined with virtually every surface, system, and space thoughtfully transformed, this exceptional home was designed to live as beautifully as it looks. Sunlight pours through expansive impact glass, illuminating sophisticated interiors where clean architectural lines, custom finishes, and seamless indoor-outdoor living create an atmosphere of effortless elegance. Every detail reflects a commitment to quality rarely found in today's market. Anchoring the home is a spectacular chef's kitchen designed for both culinary excellence and unforgettable entertaining. An extraordinary suite of Wolf and Sub-Zero appliances—including an eight-burner gas range with griddle, built-in coffee system, Cove dishwasher, designer refrigeration, oversized pantry, and a dramatic entertaining bar—is complemented by custom cabinetry, multiple beverage centers, ice makers, and a stunning temperature-controlled glass wine room worthy of the finest private collections. The primary suite offers a tranquil retreat inspired by the world's finest luxury resorts, while beautifully redesigned guest suites provide exceptional comfort and privacy. Throughout the residence, Turkish shell stone flooring, TruStile doors, EMTEK hardware, floating custom cabinetry, Level 5 wall finishes, and designer appointments create an understated elegance that feels both warm and sophisticated. Behind the walls lies a level of engineering that is seldom seen. A state-of-the-art Josh AI automation system seamlessly integrates lighting, climate, security, audio, and mechanical systems into one intuitive platform, placing the entire home at your fingertips. Whole-home True Audio speakers, buried fiber connectivity, dedicated IT infrastructure, multiple wireless access points, and integrated security provide technology equal to the home's extraordinary design. Constructed with longevity in mind, the residence showcases impact-rated windows and doors, concrete block construction, spray foam insulation, a standing seam metal roof, elevated mechanical systems, new electrical service, new plumbing, new water and sewer infrastructure, WiFi-enabled tankless water heaters, and countless improvements that reflect an unwavering commitment to enduring quality. Outside, the boundaries between home and resort disappear. A completely reimagined pool, expansive terraces, architectural ceilings, lush tropical landscaping, dramatic landscape lighting, and a fully appointed Wolf outdoor kitchen create an extraordinary backdrop for entertaining beneath Sarasota's spectacular sunsets. For boating enthusiasts, the experience is simply unmatched. With newly dredged water access, newer dock, and no bridges to Sarasota Bay, spontaneous afternoons on the water and unforgettable Gulf sunsets become part of everyday life. More than a luxury residence, 1516 Ridgewood is a home that inspires. It is the rare combination of visionary design, uncompromising construction, intelligent technology, and an incomparable waterfront setting—created for those who believe true luxury is measured not only by beauty, but by the extraordinary way a home makes you feel.

1516 Ridgewood Lane, Sarasota
$3,100,000
3 Beds ⋅ 3 Baths ⋅ Kentwood Estates SubDv. ⋅ 34231 Zip Code
On an elevated lot in the quiet, refined community of Kentwood Estates near Oyster Bay, this modern residence exudes Zen-like sophistication. From its contemporary architecture to its park-like half-acre grounds, 1556 Eastbrook Drive offers a uniquely compelling experience. Vaulted ceilings and insightfully placed windows create an ethereal ambiance as you enter this home. Bleached oak flooring (throughout the entire home) and abundant LED lighting create a bright, inviting environment. And, with concrete block construction, impact windows and doors, and a location well above flood zone, you’ll be secure no matter what the environment. Created for entertaining and effortless daily living, the upscale kitchen provides everything a home-chef wants, such as Thermador appliance package including custom separate built-in refrigerator and freezer, 48-inch dual fuel professional range and dishwasher; built-in drawer microwave, custom cabinetry, aluminum tambour, quartz countertops, rare quartzite backsplash, two sinks with disposals, Kohler Karbon articulating faucets and reverse osmosis drinking water system. Tucked behind the kitchen is a large utility area functioning as a butler’s pantry/work zone with John Boos countertops and wine cooler. On the other side of the kitchen is a full bath that serves as the pool bath. The main living area presents a 20-foot vaulted ceiling, architectural windows, gas fireplace, built-ins with accent lighting and a wall of sliding glass that leads to the outdoor retreat and pool. This central living area, including the open kitchen and dining space, ideally separates the guest rooms from the owners’ suite. Going from the main living area into the owners’ suite, you enter a large private area that can serve as an office/den, exercise space or quiet reflection area with its five oversized windows. The suite continues with a generous sleeping area and sliding glass doors. The adjacent spa-like bath is exquisite with floor-to-ceiling tile, designer fixtures, a multi-head shower and views of the tropical foliage outside. Walk-in closets include built-in custom cabinetry and remote control hangers. On the other side of the home are two generous guest rooms and full bath. The outdoor living area provides the epitome of Florida lifestyle. Accessed from the main living area and the owners’ suite, it offers ample covered sitting areas to accompany the outdoor kitchen with an Alfresco Grill, dining area and entertaining space with cypress ceiling and cabinetry. The heated saltwater pool includes fountains, underwater lighting, and an abundance of deck space to take in the sun and fun. The professionally landscaped half-acre lot is ideal for sports, pets, gardening or simply a park-like respite in daily life. The significantly oversized, climate-controlled garage is large enough for two full-sized vehicles and a work area, and it also includes an electric car charger. Essentially a smart home, most functions can be controlled through apps on your smartphone, as audio, security, climate, lighting and more are in your hands. Additionally, the owners replaced all three HVAC systems and invested more than $100,000 in landscaping. Optimally in the desired West of Trail area, this residence is close to Red Rock Park, The Field Club (historic private waterfront club with boating facilities), South Side Village, access to Siesta Key and everything that makes Sarasota a place to call home.

1556 Eastbrook Drive, Sarasota
$749,000
4 Beds ⋅ 3 Baths ⋅ Phillippi Hi SubDv. ⋅ 34231 Zip Code
Not every buyer is looking for a cookie cutter home. If you've been searching for a property with character, modern updates, and an unbeatable Sarasota location, welcome to 4074 Redbird Circle. Perfectly positioned on nearly a third of an acre, this fully renovated 4 bedroom, 2.5 bathroom home offers the space, privacy, and personality that's becoming harder to find in Sarasota. From the moment you arrive, the horseshoe driveway, mature landscaping, and welcoming front porch set the tone for what's inside. The heart of the home is a thoughtfully designed kitchen built for gathering. The oversized quartz waterfall island comfortably seats up to eight, complemented by brand new stainless steel appliances, abundant storage, and natural gas availability for future cooking options. Just beyond, the wood burning fireplace creates a warm focal point in the living room, while the adjacent dining nook overlooks the backyard through a charming bay window. The primary suite is privately tucked away on the first floor, offering vaulted ceilings, a custom walk in closet, dual vanities, and a spacious walk in shower. Upstairs, three additional bedrooms and a full bathroom provide flexibility for family, guests, or a home office. Step outside to the large screened lanai, an ideal space for morning coffee, weekend barbecues, or relaxing after a day at the beach. The expansive backyard offers room to play, entertain, garden, or even add a future pool. A fenced side yard provides a great space for pets, while the oversized two car garage includes built in cabinets and shelving for additional storage or workshop space. Beyond the cosmetic renovation, you'll appreciate the major improvements already completed, including a new roof, newer HVAC system, updated PVC plumbing, fresh interior and exterior paint, and move in ready condition throughout. Location is where this home truly shines. Nestled among established homes near Shady Creek, you'll enjoy convenient access to boating, kayaking, and paddleboarding while being just minutes from Siesta Key Beach, Downtown Sarasota, Sarasota Memorial Hospital, Trader Joe's, CineBistro, University Town Center, golf, dining, shopping, and some of Sarasota's highest rated public and private schools. Whether you're looking for a full time residence or a Florida retreat, 4074 Redbird Circle delivers something increasingly rare: a home with character, meaningful updates, and a location that puts the very best of Sarasota right at your doorstep.

4074 Redbird Circle, Sarasota
$4,950,000
5 Beds ⋅ 6 Baths ⋅ Coral Cove SubDv. ⋅ 34231 Zip Code
Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best of Sarasota’s luxury lifestyle. Encompassing over 6,100 square feet, the residence was thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. A dramatic two-story living room, sweeping staircase, extensive custom millwork, and walls of glass create a sense of timeless elegance while framing breathtaking water views throughout the home. The gourmet kitchen serves as the heart of the residence, seamlessly connecting to multiple gathering spaces and opening effortlessly to the expansive waterfront terrace. Corner sliding glass doors dissolve the boundaries between indoors and out, revealing a resort-style infinity-edge pool, summer kitchen, covered entertaining areas, and sparkling bay views beyond. The luxurious primary suite is a private waterfront retreat featuring a separate dressing room, generous dual closets, and serene water vistas. Additional guest suites provide exceptional comfort and privacy for family and visitors alike. Designed for both recreation and relaxation, the home also features a private office/library, elevator access, media and game room with full bar, and a four-car split garage. Outside, the lifestyle continues with a private dock, boat lift, fishing pier, and immediate access to Sarasota Bay. Whether enjoying sunset cruises, waterfront dining, or simply relaxing poolside while watching dolphins and boats pass by, every day feels like a vacation. Rarely does a property combine this level of space, waterfront presence, boating access, and location. Just minutes from downtown Sarasota, St. Armands Circle, and the area’s renowned beaches, this is a home designed for those who expect the very best.

1541 Caribbean Drive, Sarasota
$269,000
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
A HIDDEN SARASOTA GEM — FULLY REMODELED, FIRST FLOOR & STEPS FROM THE POOL! If you’ve been waiting for a condo that feels fresh, modern and completely move-in ready, this may be the one. Beautifully updated from top to bottom, this light and bright 2-bedroom, 2-bath residence features a 2021 fully remodeled kitchen and bathrooms, new flooring, new A/C (2026), fresh interior paint and trim, and a soft modern coastal palette that feels right at home in Sarasota. And the location within the community is hard to beat. This first-floor residence is in the building right next to the heated pool, gazebo and outdoor grills — yet Crooked Creek feels tucked away from it all, surrounded by mature landscaping and nature. One of the community’s best-kept secrets? A private gated entrance directly into the 72-acre Red Bug Slough Preserve, where miles of walking trails, wildlife and peaceful natural surroundings are practically in your backyard. Residents also enjoy tennis/pickleball, bike storage and a community storage building with individual 5' x 3' storage lockers for condo residents. Just as important, Crooked Creek is a community that has continued to invest in itself. Recent improvements include roofs replaced in 2021, resurfaced heated pool (2025), freshly painted buildings and new carports (2024-2025), along with well-maintained grounds and community amenities. The HOA fee also includes full exterior maintenance, grounds maintenance and Wi-Fi. Nature outside your door. Sarasota at your fingertips. Nothing to renovate. Just move in and enjoy. At its new price of $269,000, this is one Sarasota hidden gem you’ll want to see in person.

3361 Cross Creek Drive Unit 3361, Sarasota
$1,597,000
4 Beds ⋅ 4 Baths ⋅ Phillippi Gardens SubDv. ⋅ 34231 Zip Code
Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.

5500 Merrimac Drive, Sarasota
$269,900
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Nestled on the second floor of Sarasota's boutique Crooked Creek community, this thoughtfully updated two-bedroom, two-bath condominium offers a rare combination of refined interiors, natural surroundings, and low-maintenance living. Since 2022, the owners have invested significantly in the home. The kitchen was fully renovated in 2023 with sleek European-style cabinetry, black granite countertops, and all-new appliances , a clean, contemporary space that anchors the open living area. Underfoot, premium engineered hardwood flooring with a 4mm wear layer (refinishable) runs through the main living and dining rooms, installed in 2022. Overhead, a designer Hubbardton Forge light fixture in the dining area and a new ceiling fan with wall switch in the living room add considered detail throughout (2024). The second bathroom received a complete refresh in 2025 with a new toilet, vanity, and flooring. Fresh paint throughout ,the living and dining rooms, kitchen, master and second baths, hallway, and master bedroom ceiling ties everything together with a crisp, move-in ready finish. The functional floor plan is further enhanced by a glass-enclosed porch, offering additional living space and a seamless connection to the outdoors. The unit enjoys a private, tranquil setting with views of mature tropical landscaping and the adjacent Red Bug Slough Preserve a natural buffer that creates a true sense of retreat while keeping you centrally located. Crooked Creek is a 78-unit community with a heated pool, tennis and pickleball courts, a clubhouse, and outdoor gathering areas. Covered assigned parking and dedicated storage are included. Shopping, dining, and area beaches are all just minutes away.

4957 Cross Creek Road Unit 4957, Sarasota
$3,500,000
4 Beds ⋅ 3 Baths ⋅ Aqualane Estates SubDv. ⋅ 34231 Zip Code
Perfectly positioned along the water, this exceptional residence offers the coveted Siesta Key waterfront lifestyle—without living on the island. Tucked away on a quiet street, this contemporary home enjoys desirable southern exposure and approximately 100 feet of canal frontage with direct boating access to Sarasota Bay. Designed for both entertaining and everyday living, the open-concept interior features soaring ceilings exceeding 14 feet and expansive walls of impact-rated pocketing glass. Open the sliders to seamlessly extend the living spaces to a covered outdoor lounge, resort-style pool and spa, and fully equipped outdoor kitchen—all overlooking the water and creating the indoor-outdoor lifestyle Sarasota is known for. Privately positioned on the east side of the home, the primary suite is a serene retreat with oversized windows and expansive glass sliders opening directly to the waterfront pool terrace. A custom walk-in closet and spa-inspired en-suite bath complete the luxurious space. On the opposite wing, two sun-filled guest bedrooms feature generous walk-in closets and share a beautifully appointed bath. A versatile bonus or media room offers additional flexibility as a fourth bedroom, complete with its own en-suite bath and walk-in closet—ideal for guests, extended family, or a private retreat. Additional features include a dedicated study or den and a fully air-conditioned split three-car garage, with thoughtfully designed spaces throughout that balance contemporary style with everyday functionality. For those drawn to life on the water, approximately 100 feet of canal frontage provides direct boating access to Sarasota Bay and the Intracoastal, with the opportunity to create a custom dock for your boat and water toys. With no HOA restrictions, the property offers exceptional flexibility to enjoy the waterfront lifestyle on your terms. Spend your days by the pool, head out by boat to explore Sarasota Bay and the Intracoastal, and return home to breathtaking sunsets over the water from your own backyard. From this private waterfront setting, you’ll also enjoy front-row views of Siesta Key’s Fourth of July fireworks—bringing some of the area’s most memorable coastal experiences right to your doorstep. Just minutes from Siesta Key Beach, Downtown Sarasota, and the area’s premier dining, shopping, and cultural destinations—including The Bay Park, Marie Selby Botanical Gardens, and the Van Wezel Performing Arts Hall—this exceptional residence brings together contemporary design, privacy, boating access, and the best of Sarasota’s coastal lifestyle.

1643 Stanford Lane, Sarasota
$26,400,000
4 Beds ⋅ 6 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Villa Meraviglia is a rare waterfront estate where architectural distinction and modern comfort come together in a home designed for an exceptional way of life. Set on 1.22 bayfront acres in Oyster Bay Estates, the residence commands 146 feet of direct frontage along the shimmering waters of Little Sarasota Bay. Here, mornings begin with light dancing across the water, afternoons unfold poolside, and evenings linger over dinner as the sun slips below the horizon. With panoramic western views and year-round sunsets, every day offers a front-row seat to the ever-changing beauty of the bay. Reimagined and completed in 2020, the estate draws inspiration from the worlds most famous waterfront villas. A striking custom gate creates a memorable sense of arrival, while two additional gold-leafed gates offer privacy and discreet access—including a private entrance to the neighboring yacht club. Inside, nearly 10,700 square feet of refined living space is complemented by more than 4,000 square feet of additional air-conditioned space devoted to leisure, entertainment, and creativity. Four beautifully appointed en-suite bedrooms offer private retreats, complemented by two stylish powder rooms for guests. Covered terraces extend from the main living areas on both levels to enjoy spectacular sunsets and sweeping bay views. The heart of the home is designed around gathering. With dual Clive Christian-inspired kitchens, every occasion, from a quiet breakfast to a celebratory dinner, unfolds with ease. Throughout the residence, Venetian plaster walls, 23-carat gold-gilded millwork, hand-painted frescoes, pecky cypress ceilings, stone-inlaid courtyards, and imported Italian materials create an atmosphere that feels timeless, distinctive, and deeply personal. Thoughtful luxuries extend throughout, from bespoke hardware, statement lighting and finishes to an elevator, whole-house generator and three-car garage. And then there are the spaces designed simply for enjoying life. Whether it is a family movie night, a spirited game of pool, or an evening gathered with friends, every space encourages connection. Outside, life naturally moves toward the water. Layered terraces create intimate settings for morning coffee, sunset cocktails, and quiet evenings beneath the stars. The resort-style pool becomes the center of days spent outdoors. The octagonal pavilion and beautifully crafted summer kitchen, with Chicago brick and a herringbone ceiling adding warmth and character, set the stage for effortless outdoor entertaining. The pool terrace is a destination in itself. Italian marble unfolds across the deck with intricate mosaics framing the water. A dramatic Medusa-inspired walkway draws you toward the private dock, where boat and jet-ski lifts make spontaneous days on the bay part of everyday life. From a morning cruise to a sunset ride across the water, the bay is always within reach. Here, luxury is something to experience. It is barefoot afternoons by the pool, dinners that stretch late into the evening, boats heading out at golden hour, and quiet mornings when the bay is perfectly still. Private and serene, yet close to The Field Club, Sarasota’s celebrated arts and dining scene, and the Gulf’s beautiful beaches, Villa Meraviglia offers a rare opportunity to live surrounded by beauty while remaining within easy reach of everything that makes Sarasota special. A remarkable home, an extraordinary setting, and a lifestyle meant to be savored.

1310 S Lake Shore Drive, Sarasota
$5,980,000
4 Beds ⋅ 7 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.

1521 S Lake Shore Drive, Sarasota