Step into history and timeless elegance at the House of Ringling, a landmark estate in Sarasota's coveted Whitfield Estates, built in 1918 for Alfred Ringling of the legendary Ringling Brothers. Spanning 4,782+/- sq. ft., this 5BR, 4.5BA masterpiece seamlessly marries Gilded Age opulence with modern luxury. A red brick walkway and expansive front lawn welcome you to this architectural treasure, where an oversized Grand Ballroom with a 21-foot ceiling, Venetian columns and a Renaissance-style coffered ceiling create an awe-inspiring focal point. Original pine floors, 12-inch baseboards and hand-poured antique glass in French windows and doors preserve the estate’s rich craftsmanship, as the reimagined chef’s kitchen is a showpiece, featuring Big Chill appliances, an 8-burner gas stove, Quartzite surfaces, a mother-of-pearl backsplash and backlit cabinets. The primary suite on the lower level offers floor-to-ceiling French doors opening to a private porch and the expansive pool deck. Upstairs, 2 ensuite bedrooms feature partial bay views. Hidden details, including a prohibition-era speakeasy/3rd bedroom at the top of the stairs and a secret room, add intrigue and charm. The home’s walls, crafted from Ringling railway car paneling, echo its storied past. Recent updates, including new plumbing, electrical, HVAC (5 units), and a new roof with extra tie-down straps, ensure modern comfort while preserving historic character. A detached 2-car garage and 2 driveways provide ample space, while the expansive Palm Beach-style courtyard invites relaxation. As one of the first Ringling Brothers homes in Sarasota, this estate offers a rare opportunity to own a living piece of history in a prime location near Sarasota Bay and downtown.

This tastefully updated and remodeled single story home is ideally located within the sought after Bird Key neighborhood. Set on a large corner lot, it features a clean, contemporary style that feels both current and easy to live in. The home offers three bedrooms, two and a half bathrooms, and a two car garage, creating a comfortable and well balanced living environment. Inside, the open concept split floor plan provides both flow and definition, with separate living and family rooms suited to modern living. The remodeled kitchen features quartz countertops and sleek contemporary cabinetry and is centrally positioned to connect the main living, dining, and family spaces.
Both living areas open through impact sliding glass doors to the lanai and pool, creating an easy transition between indoor and outdoor living. Fully opening sliders from the living and family rooms extend the space onto the pool deck, making the home particularly well suited for entertaining. The primary suite includes a spacious bedroom, walk in closet, and an updated en suite bathroom. Two additional guest bedrooms and a bathroom are located on the opposite side of the home, offering privacy for family and guests. The generously sized family room easily incorporates a small home office area. Recent improvements include a new tile roof in 2025, whole house propane generator 2025, a newer air conditioning system in 2023, and impact windows for added security and peace of mind. Bird Key offers one of Sarasota’s most desirable locations, just minutes from downtown Sarasota, St. Armands Circle, and Lido Beach. Residents also benefit from the nearby Bird Key Yacht Club, currently undergoing a full redevelopment and expected to reopen early in 2027 as a premier destination for boating, tennis, and social activities. PLEASE NOTE FRONT DOOR ENTRY IS LOCATED ON BOBWHITE WAY.

This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for strong income in $160K to $180K range annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you. Seller Financing Available.

Step into refined coastal living in this five-bedroom residence with office and bonus loft, located within the gated boating community of Harbour Walk at The Inlets. Designed by Rutenberg Homes, this Key West–inspired property blends timeless architecture with modern functionality and direct water access—creating an exceptional opportunity for boaters and those seeking an elevated Florida lifestyle.

A welcoming front porch, porte-cochère, and three-car tandem garage introduce the home’s thoughtful design. Notable features include impact glass throughout, new storm shutters, a Generac whole-house generator, water softener, and a kitchen reverse osmosis system—providing comfort and peace of mind. Glass double doors open to a dramatic foyer anchored by a handcrafted wood staircase, flanked by formal living and dining rooms.

Inside, travertine flooring, cathedral ceilings, and expansive windows and sliders fill the home with natural light. The chef’s kitchen is equipped with custom cabinetry featuring glass display panels, stainless-steel appliances, granite countertops, and a center island with seating. The adjoining family room flows seamlessly to the outdoor living area, extending the home’s livable space by more than 1,200 square feet.

Outdoor living is a true highlight, with polyaspartic flooring spanning the lanai, front entry, and garage for durability and style. The covered lanai includes a summer kitchen with built-in gas grill, ideal for entertaining. The heated pool and spa feature a swim-up table and seating, all overlooking nearly 100 feet of canal frontage. A 22,000-lb boat lift offers quick access to the Manatee River, making this property ideal for boating enthusiasts.

The first-floor primary suite serves as a private retreat, offering a sitting area, terrace access, and a spacious en-suite bath. A dedicated office with custom built-ins is also located on the main level. Upstairs, a bonus loft with morning kitchen and private balcony overlooks the pool and waterway. Four additional bedrooms provide flexible accommodations, including one with a Murphy bed, two sharing a Jack-and-Jill bath, and a fifth with a private en-suite and walk-in closet.

Ideally located near Sarasota, Bradenton, and Lakewood Ranch, this waterfront home offers convenient access to dining, shopping, and cultural attractions. Award-winning beaches including Anna Maria Island, Longboat Key, and Siesta Key are just a short drive away, along with premier golf courses and marinas—delivering the very best of Florida’s coastal lifestyle.

Discover the essence of Florida coastal living at this exceptional custom-built Key West-inspired waterfront estate, where nearly two private acres, direct bay access, and timeless craftsmanship come together on historic Terra Ceia Island. Completed in 2021, this elevated coastal residence offers an extraordinary blend of privacy, boating freedom, and panoramic views across Terra Ceia Bay. This residence commands approximately 117’ of waterfront overlooking the bay. A private dock extends through a tranquil mangrove estuary to a pier equipped with water and electricity, offering direct bay and Gulf access with no fixed bridges. Spanning nearly 3,000 square feet of thoughtfully designed living space, the elevated home embraces relaxed coastal elegance throughout. Rich pine wood flooring, custom shiplap detailing, tongue-and-groove ceilings, impact-rated windows and doors, and abundant natural light create an inviting atmosphere that complements the surrounding waterfront landscape. An elevator services each living level, while expansive covered and screened verandas capture uninterrupted water views from nearly every room. Occupying the upper living level, the open-concept great room is designed for effortless entertaining. Walls of glass frame sweeping bay vistas while seamlessly connecting the spacious living area, dining space, and gourmet kitchen. The chef's kitchen is beautifully appointed with custom cabinetry, oversized center island, stone countertops, premium appliances, dual side-by-side refrigerators, oversized professional range with pot filler, wine refrigerator, coffee bar with filtered water, walk-in pantry, and generous preparation space—creating the perfect setting for everything from casual family meals to large gatherings. The primary suite occupies its own private level and serves as a peaceful waterfront retreat. The spa-inspired bath features a freestanding soaking tub, oversized custom-tiled walk-in shower, dual vanities, designer lighting, and two spacious walk-in closets. An adjoining flex room provides exceptional versatility as a nursery, home office, fitness room, or private sitting area. A second guest bedroom, full bath, and oversized laundry room complete this level, while an additional guest suite with en-suite bath occupies the upper floor to maximize privacy. Outdoor living is equally exceptional. The resort-inspired saltwater pool is surrounded by expansive pavers, lush tropical landscaping, and multiple gathering spaces. A convenient pool bath serves the outdoor living areas, while the fully fenced grounds provide ample room for recreation, gardening, or future enhancements. Three oversized tandem garage bays with 10’ doors, 12’ ceilings, extensive storage, workspace, and room for recreational vehicles provide unmatched functionality. Additional features include a whole-house generator, metal roof, security gate, zoned HVAC systems, and exceptional craftsmanship that provides lasting peace of mind. Terra Ceia Island remains one of Florida's hidden coastal treasures. Residents can join the association, which offers access to a private waterfront park featuring a community boat ramp, fishing, pickleball, playground, and year-round neighborhood gatherings. Despite its peaceful island setting, this home enjoys exceptional convenience with quick access to I-275 and I-75, placing downtown St. Petersburg, Tampa, Bradenton, Lakewood Ranch, Sarasota, and multiple Gulf Coast beaches within easy reach.