Palm Aire Homes with Bay View Water Frontage

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

$1,490,000

SubDv. ⋅ 34243 Zip Code

Discover a once-in-a-lifetime opportunity to own a PREMIER 1.08-ACRE BAYFRONT LOT located “WEST OF THE TRAIL” at 8258 Long Bay Blvd., Sarasota, FL — a true TROPHY PROPERTY offering UNOBSTRUCTED VIEWS OF SARASOTA BAY, priceless SUNRISES & SUNSETS, and endless possibilities to build your CUSTOM LUXURY ESTATE! This OVER 1 ACRE WATERFRONT LOT features UTILITIES AVAILABLE, a NEWER SEA WALL already in place, NO HOA FEES, and is positioned at a HIGH ELEVATION where the MAJORITY OF THE PROPERTY IS NOT LOCATED IN A FLOOD ZONE — ABSOLUTELY UNHEARD OF for BAYFRONT living! SAVE THOUSANDS IN CONSTRUCTION COSTS by building outside of the A & V flood zones while enjoying peace of mind and the ultimate Florida waterfront lifestyle. This MUST-SEE VACANT LOT wraps around the BAY with exceptional DEPTH, PRIVACY, and room to BUILD A DOCK large enough for YACHTS, BOATS, JET SKIS, KAYAKS, PADDLEBOARDS, and all your WATER TOYS. Spend your days FISHING RIGHT FROM YOUR BACKYARD, boating across Sarasota Bay, entertaining waterfront guests, or simply relaxing while taking in breathtaking water views every morning. The iconic CROSLEY MANSION and world-renowned RINGLING MUSEUM are your neighbors to the south, placing you in one of Sarasota’s most PRESTIGIOUS and CULTURALLY RICH waterfront corridors. This PRIME INVESTMENT OPPORTUNITY also allows for an ACCESSORY DWELLING UNIT (ADU) up to 80% of the primary home size — ideal for a PRIVATE GUEST RETREAT, MULTI-GENERATIONAL LIVING, or INCOME-PRODUCING RENTAL with its own address. Enjoy DEEP BAYFRONT TRANQUILITY while remaining minutes from WORLD-CLASS DINING, SHOPPING, ARTS, ENTERTAINMENT, and Sarasota’s stunning GULF BEACHES. OWNER IS MOTIVATED — opportunities like this rarely hit the market, so CONTACT US TODAY before this extraordinary piece of SARASOTA BAY PARADISE is gone!

8258 Longbay Blvd, Sarasota

$3,200,000

4 Beds ⋅ 5 Baths ⋅ Ballentine Manor Estates SubDv. ⋅ 34243 Zip Code

"The Ultimate Resilient Estate" offers rare coastal luxury, modern 2019 construction, and true peace of mind on Sarasota Bay. Why deal with the frustrations of low bridge restrictions or long, tedious idle zones of standard canal-front properties? Built to CAT 5 wind standards at a 14FT elevation, this single-level 4BR/4.5BA custom home requires no flood insurance and had no flooding in 2024. The interior features soaring ceilings, cypress details, and a primary suite with dual baths and dual walk-in closets. Enjoy 180-degree bay views, a heated pool/spa, newer seawall, and an 8’x30’ dock with a 7,500lb lift. Positioned in a zero-wake basin with immediate open-water access to the Gulf, the marine setup features seasonal flexibility: a 500FT direct high-tide summer route to the open bay, or a winter channel rated conservatively for a 20” draft that deepens by 1.5FT just 1,500FT North. Neighborhood allows weekly rentals. Optional Sara Bay CC culinary membership available

7927 Longbay Boulevard, Sarasota

$660,000

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

Experience the best of Sarasota living in this beautifully updated single-story ranch home with pool, nestled in sought-after Whitfield Estates—a Manatee County gem with a Sarasota address. Situated near Sarasota Bay, this home sits among multi-million-dollar residences and offers the perfect blend of comfort, charm, and opportunity. This 3-bedroom, 3-bath home welcomes you with bright, open living spaces filled with natural light. The primary bedroom and 2nd bedroom both feature walk-in closets and ensuite baths. The open-concept floorplan connects the living, dining, and kitchen areas—ideal for entertaining or relaxing by the cozy fireplace. A stylish kitchen bar provides extra seating and a central gathering spot. Step outside to your private Florida oasis: a heated pool with screened enclosure, surrounded by lush landscaping on a spacious 1/3-acre lot. Enjoy morning coffee on the front patio with peek-a-boo views of Sarasota Bay, or take an evening stroll to the bay and watch the sunset. Whether you’re searching for a full-time residence, seasonal retreat, or short-term rental investment, this property offers endless possibilities in one of Sarasota’s most desirable neighborhoods. This property is built of concrete block construction, has impact windows, and sits in the desirable X flood zone (flood insurance is not required). Roof is membrane material (2017). AC (2023). For an optional annual HOA fee of just $35, homeowners in Whitfield Estates may obtain a culinary membership at Sara Bay Country Club, granting full access to the clubhouse for dining and social events (golf privileges not included; membership subject to club approval). You and your guests will have plenty of entertainment and convenience options within a short drive including Sarasota Bay, IMG Academy, SRQ Airport, University Towne Center Mall, downtown Sarasota, St. Armands Circle, Lido Key and gulf beaches.

214 Gaines Avenue, Sarasota

$429,900

Whitfield Estates SubDv. ⋅ 34243 Zip Code

SEDUCTIVE SARASOTA BAY VIEWS! Have you been spending countless hours staring at your phone into the wee hours of the morning, scrolling through properties that just don’t fit the bill… not to mention driving the wheels off your car every weekend since God knows when trying to find the needle in the haystack? WE HAVE THE FIX, so put down the phone and save your gas money for more important things. Picture this… you’re sitting on the back porch of your NEW Florida Dream Home, overlooking the shimmering waters of Sarasota Bay, watching the sun dance across the horizon as seabirds glide overhead. No need to imagine being “close” to the water — this lot offers direct views of Sarasota Bay, delivering the coastal backdrop buyers dream about but rarely find. Nestled in the peaceful and coveted Downtown Sarasota suburb of Whitfield Estates, flanked by iconic landmarks such as The Ringling Museum and surrounded by historic residences that have played host to some of the most esteemed members of high society for over a century, this property represents one of the few remaining opportunities to build in such a distinguished and established setting. Whether you fancy yourself a developer looking to capitalize on the prestige of a West of the Trail address with panoramic water views, or an end-user ready to design and build a custom residence tailored to your exact vision, this lot provides the canvas. The optional HOA is only $30 annually, there are NO CDD FEES, and restrictions are minimal — giving you flexibility without sacrificing neighborhood character. For boating enthusiasts, convenient access to Sarasota Bay is available via the public boat ramp at Bahia Mar West Marina, allowing you to be on the water in minutes. For the lifestyle seeker, you’re just moments from the shops and dining of Downtown Sarasota, St. Armands Circle, and some of Florida’s most world-renowned beaches — close enough to enjoy, yet far enough to retreat into your own waterfront sanctuary. It’s commonly been said, “The value is in the land.” And in this case, the value is in the land… and the view. They aren’t making any more waterfront parcels overlooking Sarasota Bay. DO NOT ALLOW THIS OPPORTUNITY TO SAIL OFF INTO THE SUNSET WITHOUT YOU!

7510 Westmoreland Drive, Sarasota

$2,500,000

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

Rare Direct Bayfront Opportunity on Over 1 Acre – No Bridges, Deep Water Access. Bring your vision to life on this exceptional waterfront property offering over one acre directly on the bay with no bridges to open water and deep-water access. This is a rare chance to create one or multiple custom coastal retreats in a premier boating location. The home features a beautiful concrete seawall and expansive water frontage, perfect for boaters, anglers, and sunset lovers alike. The property was impacted by a hurricane, and all drywall has been removed, leaving a clean slate that’s ready for your rebuild, remodel or redesign—ideal for buyers who want to customize finishes, layout, and style to their taste. With unmatched views, generous lot size, and direct bay access, this property offers incredible upside and long-term value. Whether you’re looking to restore, reimagine, or rebuild, this is a prime waterfront canvas! Adjoining properties are also for sale at the time of this listing, if you dare to dream even larger! Don’t miss this opportunity to craft your dream home on the water. Seller Financing terms available for qualified Buyers. Unmatched location! Close to SRQ Airport, New College, Downtown Sarasota, Ringling Museum, UTC Mall, endless shopping, dining and water opportunities await you.

7322 Westmoreland Drive, Sarasota

$2,000,000

4 Beds ⋅ 5 Baths ⋅ North Isles SubDv. ⋅ 34243 Zip Code

WOW..the view! This exceptional waterfront property is offered for only the second time since 1958. Ideally positioned directly on Sarasota Bay, it features sweeping bay views. Experience the magical sunsets, then the twinkling lights of Longboat Key at night. Nature lovers can enjoy the variety of birds, manatees, and frolicking dolphins. Each day is a new show of natural beauty, and the sunsets never get old. The estate-sized 0.80-acre lot offers approximately 103 feet of direct bay frontage, providing an extraordinary setting for a custom coastal retreat, and a coveted Sarasota address within Manatee County. The existing home sustained hurricane damage, presenting a rare opportunity for a new owner to reimagine or rebuild and create their dream waterfront estate. Located on boating water with access to the Intracoastal Waterway and the Gulf of Mexico, this property is perfectly suited for boating and fishing enthusiasts. An expansive raised edge pool with paver deck, fenced yard, private well irrigation and propane gas add practical value to this unique offering. The Whitfield Estates community has a rich history and is an eclectic mix of homes from 1920’s Mediterranean architecture to modern designs. Voluntary neighborhood association membership is just $30 annually and includes access to nearby Sara Bay Country Club for culinary membership. Centrally located just minutes from downtown Sarasota’s cultural attractions, dining, shopping, IMG Academy, renowned Gulf beaches, and SRQ International Airport—only five minutes away. Waterfront opportunities of this caliber are increasingly rare. Embrace the potential, the location, and the timeless appeal of Sarasota Bay living, and make this extraordinary property your own.

7318 Westmoreland Drive, Sarasota

$2,300,000

North Isles SubDv. ⋅ 34243 Zip Code

Spectacular Sarasota Bay Front Lot! Seize this rare opportunity to build your dream home on this .76 acre estate sized lot on the breathtaking shores of Sarasota Bay. Construct your waterfront masterpiece in the highly sought-after historic Whitfield Estates neighborhood known for its mature trees and diverse architectural style homes. This cleared and buildable lot offers boatable water with direct access to the intercoastal waterway and the Gulf of Mexico. Saving time and planning, this lot is already equipped with a brand new seawall, a new boat dock and two new jet ski lifts, making it a dream location for any water enthusiast. Enjoy unobstructed sunsets and stunning evening views with the bay lit up at night, stretching straight across to Longboat Key and Sarasota. Whitfield Estates residents can enjoy an optional $35 annual fee to join the Sarasota Bay Club's culinary membership granting exclusive access to the clubhouse for dining and social events. Golf membership is available separately at the reputable SaraBay Country Club. Conveniently located just minutes from the Sarasota's pristine Gulf Coast beaches, Siesta Key and nightlife full of vibrant entertainment featuring the Ringling Museum of Art, The Asolo Theatre, Van Wezel Performing Arts Hall, world renowned IMG Academy, Sarasota Bradenton International Airport, St. Armand's Circle and downtown Sarasota's famous restaurants and boutique shopping. Don't miss this extraordinary opportunity to build your waterfront sensation in the beautiful Florida Sunshine State.

7314 Westmoreland Drive, Sarasota

Palm Aire Homes with Bay View Water Frontage

Newest Palm Aire Homes with Bay View Water Frontage