Palm Aire Homes with Bay Front 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

$89,900

1 Baths ⋅ Sarasota Cay Club Condo SubDv. ⋅ 34243 Zip Code

Top-floor unit in the waterfront condo-hotel at the Ramada by Wyndham Sarasota Waterfront, ideally positioned in a quieter area of the building away from pool, restaurant, and marina traffic. Enjoy added privacy, minimal foot traffic, and no upstairs noise to enhance increased long term appeal. Turn-key furnished with updated flooring, newer A/C-heat wall unit, and freshly painted interior. Clean, functional, and ready for immediate use, rental, or future personalization based on buyer preference Located just minutes from SRQ airport, downtown Sarasota, and Gulf beaches. Community amenities include waterfront setting, pool, on-site dining, fitness center, business center, and flexible rental options. Aggressively priced as one of the lowest in the building, providing strong value for investors or buyers seeking a low entry point into the Sarasota market.

7150 N Tamiami Trail Unit S-604, 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

$1,295,000

3 Beds ⋅ 3 Baths ⋅ North Isles SubDv. ⋅ 34243 Zip Code

On a large waterfront homesite in the North Isles neighborhood of Whitfield Estates, this property offers the kind of Florida lifestyle buyers actively seek with sailboat water basin, boat dock, two remote-control boat lifts, quick access to Sarasota Bay, a screened heated pool and spa, and room to enjoy it all on nearly half an acre. The .43-acre lot is beautifully landscaped and features a screened food garden, irrigation well, brick paver walkways and a solar PV system. Inside, the residence was solidly upgraded in 2023 and well-finished with travertine tile flooring through the main living areas and baths, luxury vinyl plank in the bedrooms, crown molding and wood shutters throughout. The layout includes three bedrooms, three baths and a flexible bonus room. Wood cabinetry with soft-close doors and drawers, along with abundant storage, adds everyday function to the home’s inviting interior. Notable features include hurricane-impact windows and doors, heated pool and spa, lightning protection, central vacuum and outdoor lights. For buyers seeking more than personal enjoyment, the property also offers a proven rental history, making it a compelling potential income investment as well as a waterfront retreat. North Isles is part of the historic Whitfield area, prized for its Old Florida character, spacious homesites and proximity to Sarasota Bay. The location is especially convenient. Just west of U.S. 41, near the airport, close to Sara Bay Golf and Country Club, and well positioned for an easy drive north into Bradenton or south to Sarasota.

121 Holly Avenue, Sarasota

$95,000

1 Baths ⋅ Sarasota Cay Club Condo SubDv. ⋅ 34243 Zip Code

Enjoy your getaway with the full hotel experience at the Ramada Inn, complete with a huge heated pool, World Famous Tiki Bar & Grill, Live music, and an arcade all just steps from your door. This adorably updated room has everything you need for a relaxing beach vacation or a comfortable extended stay. Perfect for families, business travelers, or solo guests seeking convenience and comfort. Secure parking, and Marina access with boat rentals available. Sleeps up to 5 guests, with one queen bed and one bunk bed. Great location, close to beaches, downtown Sarasota, Sarasota Airport and St Armand's Circle.

7150 N Tamiami Trail Unit S-614, Sarasota

$95,000

1 Baths ⋅ Sarasota Cay Club Condo SubDv. ⋅ 34243 Zip Code

Enjoy your getaway with the full hotel experience at the Ramada Inn, complete with a huge heated pool, World Famous Tiki Bar & Grill, Live music, and an arcade all just steps from your door. This adorably updated room has everything you need for a relaxing beach vacation or a comfortable extended stay. Perfect for families, business travelers, or solo guests seeking convenience and comfort. Secure parking, and Marina access with boat rentals available. Sleeps up to 5 guests, with one queen bed and one bunk bed. Great location, close to beaches, downtown Sarasota, Sarasota Airport and St Armand's Circle.

7150 N Tamiami Trail Unit S-612, Sarasota

$104,900

1 Beds ⋅ 1 Baths ⋅ Sarasota Cay Club Condo SubDv. ⋅ 34243 Zip Code

S-623 TURN KEY! (Everything is included in the sale!) A SECOND-FLOOR CITY VIEW: Newly renovated LVT living area floor with 3" baseboard moldings. Wonderful, fully functional new kitchenette with butcher block countertops and new overhead cabinets (with under-cabinet lighting), two tabletop burners, and a beautiful backsplash. A remote-control center mini-ceiling fan with light in the Living Room. In the bathroom, a brand-new Vanity and new lighting, along with a beautiful cabinet system, were also added. Welcome to the Sarasota Cay Club. This property is approximately 2 miles north of Sarasota-Bradenton International Airport, just minutes from great shopping, museums, art galleries, restaurants, farmers' markets, and other unique entertainment opportunities. This area is also well known for destination vacations with some of the best beaches in the country, including Holmes Beach, Coquina Beach, Lido Beach, Longboat Key Beach, and Siesta Key Beach. These privately owned condo residences are in the ‘Ramada By Wyndham Sarasota Waterfront Resort’. Each residence allows daily and short-term rentals with no minimum leasing restrictions. Enjoy staying in these units, located within a waterfront property with direct access to the Gulf. Owners can use their condo as a vacation property year-round. Enjoy the Ramada Hotel's Resort Lifestyle with amenities that include a newly remodeled onsite waterfront restaurant/tiki bar, ‘Tarpon Bay Grill and Tiki Bar’, heated waterfront pool, beach volleyball, fitness room, roaming security, community laundry, and open common areas. The monthly Condo-Hotel HOA fees include all utilities (Electric, Water, Internet, Cable, Phone, Sewer, and Trash, Exterior Maintenance, and Interior Common Areas), making your overhead expenses minimal and easy to budget. This rare income-producing investment opportunity allows you to enjoy all the amenities of beautiful Southwest Florida.

7150 N Tamiami Trail Unit S-623, Sarasota

Palm Aire Homes with Bay Front Water Frontage

Newest Palm Aire Homes with Bay Front Water Frontage