Whitfield Estates Homes with Bay Front Water Frontage

5 Beds ⋅ 4 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

Welcome to 7418 Westmoreland Drive, an exceptional bayfront estate offering panoramic water views, privacy, and effortless coastal living in one of Sarasota’s most desirable waterfront settings. Situated on more than half an acre with 180-degree direct bay views, this elevated residence offers 5 bedrooms, 4 baths, 3,502 square feet of living space, plus more than 1,500 square feet of additional finished ground-level space ideal for entertaining, recreation, guests, or flexible lifestyle use. Completely remodeled in 2021, the home has been beautifully reimagined with a sophisticated coastal aesthetic, modern finishes, and thoughtfully designed spaces that complement its extraordinary setting. Expansive windows fill the interiors with natural light while framing captivating bay views throughout the main living areas. Generous entertaining spaces feature custom built-ins and an inviting flow equally suited for everyday living and special gatherings. At the heart of the home, the well-appointed kitchen features stone countertops, abundant cabinetry, and generous workspace opening naturally to the surrounding living areas. The primary suite is conveniently located on the main level, offering privacy and ease of living, while additional bedrooms provide gracious accommodations for family and guests. Outdoor living is where this residence truly distinguishes itself. A screened lanai, outdoor kitchen, and private pool overlooking the bay create a resort-inspired setting for alfresco dining, sunset gatherings, and year-round entertaining. Beyond the pool, the expansive backyard leads to a private dock with water and electricity and a 10,000-pound boat lift, providing direct access to Sarasota Bay and the Intracoastal waterways. Additional features include an elevator, three-car garage, metal roof, irrigation and security systems, mature tropical landscaping, and more than 1,500 square feet of finished ground-level space. With no HOA and no CDD fees, homeowners enjoy added flexibility within an established waterfront neighborhood. Located in sought-after Whitfield Estates, this remarkable property is convenient to Downtown Sarasota, Sarasota-Bradenton International Airport, world-class dining, shopping, arts and culture, and the celebrated beaches of Florida’s Gulf Coast. From mornings on the bay and afternoons beside the pool to unforgettable sunsets over the water, 7418 Westmoreland Drive offers an extraordinary opportunity to experience the very best of Sarasota’s waterfront lifestyle.

7418 Westmoreland Drive, Sarasota

$2,150,000

5 Beds ⋅ 5 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

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.

7715 Westmoreland Drive, Sarasota

$5,500,000

6 Beds ⋅ 6 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views of Sarasota Bay, a separate guest house, and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.

7524 Westmoreland Drive, Sarasota

$1,700,000

Whitfield Estates SubDv. ⋅ 34243 Zip Code

A rare opportunity to create a legacy property along the shores of Sarasota Bay. Set on over half an acre in the heart of historic Whitfield Estates, 7538 Westmoreland Drive offers one of the area’s most compelling waterfront redevelopment opportunities. Framed by breathtaking bay views and unforgettable sunsets, this expansive homesite is where vision, architecture, and lifestyle come together. Westmoreland Drive is widely regarded as one of Whitfield Estates most desirable waterfront streets, where classic Spanish-inspired residences and Old Florida charm are giving way to stunning custom-built bayfront estates. Surrounded by multi-million-dollar homes, this property presents the ideal canvas to design and build the luxury waterfront residence you’ve always imagined. The existing home is being sold for land value, allowing the next owner to unlock the full potential of this exceptional setting. With over half an acre of bayfront property, opportunities of this scale and location have become increasingly difficult to find. Perfectly positioned just minutes from IMG Academy, Sarasota-Bradenton International Airport, downtown Sarasota, world-renowned beaches, waterfront dining, and the vibrant cultural amenities that make Sarasota one of Florida’s most sought-after destinations. Whitfield Estates also offers a voluntary neighborhood association for only $40/year, providing culinary access to the Sara Bay Country Club. Whether you’re building your forever home, a family compound, or a signature waterfront estate, this is a chance to secure a premier piece of Sarasota Bay and bring your vision to life. Waterfront homesites of this caliber are few and far between. The next chapter begins here.

7538 Westmoreland Drive, Sarasota

$1,700,000

3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

A rare opportunity to create a legacy property along the shores of Sarasota Bay. Set on over half an acre in the heart of historic Whitfield Estates, 7538 Westmoreland Drive offers one of the area’s most compelling waterfront redevelopment opportunities. Framed by breathtaking bay views and unforgettable sunsets, this expansive homesite is where vision, architecture, and lifestyle come together. Westmoreland Drive is widely regarded as one of Whitfield Estates most desirable waterfront streets, where classic Spanish-inspired residences and Old Florida charm are giving way to stunning custom-built bayfront estates. Surrounded by multi-million-dollar homes, this property presents the ideal canvas to design and build the luxury waterfront residence you’ve always imagined. The existing home is being sold for land value, allowing the next owner to unlock the full potential of this exceptional setting. With over half an acre of bayfront property, opportunities of this scale and location have become increasingly difficult to find. Perfectly positioned just minutes from IMG Academy, Sarasota-Bradenton International Airport, downtown Sarasota, world-renowned beaches, waterfront dining, and the vibrant cultural amenities that make Sarasota one of Florida’s most sought-after destinations. Whitfield Estates also offers a voluntary neighborhood association for only $40/year, providing culinary access to the Sara Bay Country Club. Whether you’re building your forever home, a family compound, or a signature waterfront estate, this is a chance to secure a premier piece of Sarasota Bay and bring your vision to life. Waterfront homesites of this caliber are few and far between. The next chapter begins here.

7538 Westmoreland Drive, Sarasota

Whitfield Estates Homes with Bay Front Water Frontage

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