Whitfield Estates Real Estate

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

CALLING ALL BOATERS! A rare waterfront opportunity awaits in sought-after Whitfield Estates, offering five private boat slips, two equipped with 10,000-lb lifts, and deep-water sailboat access with no bridges to Sarasota Bay. Situated on just over one-third of an acre, this 3-bedroom, 2.5-bath pool home with a two-car garage offers incredible potential as a primary residence, seasonal retreat or income-producing investment. Inside, the home embraces classic Florida coastal character with terrazzo floors, a spacious galley-style kitchen with abundant cabinetry and storage, formal living and dining areas, a wood-burning fireplace, full-size laundry room and a light-filled family room overlooking the water. A Florida room provides additional living and entertaining space, while large windows throughout bring in natural light and showcase the waterfront setting. The home also features updated airport windows and a tile roof. Step outside to your screened-in pool and expansive waterfront backyard, where the possibilities truly shine. With five boat slips that can be rented for additional income, two 10,000-lb boat lifts and direct deep-water access with no bridges to the bay or Gulf, this property presents an exceptional opportunity for boating enthusiasts and investors alike. Located in Whitfield Estates, one of Sarasota’s hidden gems, residents enjoy no mandatory HOA or CDD, along with flexible rental opportunities including nightly rentals. Optional membership in the Whitfield-Ballentine Manor Association is just $40 annually and includes culinary membership privileges at SaraBay Country Club. Conveniently located minutes from Sarasota Bay, SRQ International Airport, downtown Sarasota, IMG Academy, world-famous Gulf beaches, golf, waterfront dining, shopping and entertainment. Whether you envision updating the existing home into your own coastal retreat, creating a high-demand vacation rental, or simply taking advantage of an extraordinary waterfront property with income-producing dockage, 133 Holly Avenue offers possibilities rarely found at this price point. Bring your boats and your vision, Florida waterfront living starts here.

133 Holly Avenue, Sarasota

$3,250,000

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

$549,000

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

Stunning Golf Course Pool Home with Sunset Views Welcome to your slice of Sarasota paradise! Perfectly positioned on the 18th hole of the prestigious Sara Bay Country Club, this beautifully maintained 3-bedroom, 2-bath home offers nearly 2,000 sq. ft. of comfortable living space on an oversized .42-acre lot. Enjoy two spacious living areas, ideal for entertaining or relaxing with family. The heart of the home opens seamlessly to a covered lanai and sparkling pool, where you can unwind and watch the sunset over the golf course each evening. The outdoor space is truly a highlight—peaceful, private, and designed for year-round enjoyment. Inside, you’ll find a functional split floor plan, generous natural light, and charming updates that make this home move-in ready. Whether you’re hosting guests, working from home, or simply soaking up the views, every corner of this property feels inviting and serene. Located just 5 minutes from SRQ Airport and less than 15 minutes to downtown Sarasota, this home combines Florida living with everyday convenience. Golf, dining, beaches, and cultural attractions are all right at your doorstep. This home has operated as a successful rental for its current owner, and would make for a great investment property, winter retreat, or full time residence. Don’t miss your chance to live where others vacation—schedule your private tour today!

433 Whitfield Avenue, Sarasota

$425,000

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

Welcome to this well-maintained 2-bedroom, 2-bathroom home with a versatile bonus room that can be used as an office, hobby space, or additional living area. The spacious kitchen offers plenty of cabinet and counter space, along with a dinette area and a large pantry for extra storage. The split-bedroom floor plan provides privacy, while the primary suite features a walk-in closet and en-suite bathroom. Step outside to enjoy the screened lanai and private pool, perfect for relaxing or entertaining year-round. The partially fenced backyard offers additional outdoor space and includes a storage shed. Situated on a generous ¼-acre lot with no HOA fees, this property provides flexibility and room to enjoy. Conveniently located near Sarasota-Bradenton International Airport, UTC shopping and dining, and many of Sarasota's popular attractions. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this Sarasota pool home checks all the boxes. SELLER TO REPLACE ROOF PRIOR TO CLOSING!

811 Alderwood Way, Sarasota

$599,000

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

Welcome to your own private slice of paradise in the heart of Whitfield Estates. Perfectly positioned on a beautifully landscaped corner lot, this impeccably updated 3-bedroom, 2-bath residence is being offered completely turnkey furnished, making it truly move-in or rental ready from day one. During the 2024 hurricanes that hit the Gulf Coast, this home did not flood! The home is elevated nicely and a certificate is available. It is in flood zone X. Step inside to a light filled, open concept floor plan where coastal charm meets modern design. Luxury vinyl plank flooring flows throughout the home, while the stunning chef’s kitchen features shaker cabinetry, stainless steel appliances, a farmhouse sink, gorgeous countertops, and an oversized island perfect for casual dining or gathering with family and friends. The spacious living room is anchored by a beautiful stone fireplace with custom built-in shelving, creating a warm and inviting space that’s equally suited for relaxing evenings or entertaining guests. The Florida lifestyle continues outdoors with a private screened lanai featuring an in-ground spa, while the fenced backyard offers lush tropical landscaping, peaceful sitting areas, and even a raised herb garden, your own secluded oasis for morning coffee or evening cocktails. Designed for worry-free ownership, this home has been extensively updated with a new roof, updated windows, newer A/C and electrical panel, and quality finishes throughout. Currently operating as a successful Airbnb, the property also offers excellent investment potential thanks to nightly rental allowances, making it ideal as a primary residence, seasonal getaway, or income-producing vacation rental. Located just minutes from Sarasota Bay, downtown Sarasota, SRQ Airport, IMG Academy, world-famous Gulf beaches, waterfront dining, shopping, and entertainment, you’ll enjoy the convenience of one of Sarasota’s most desirable neighborhoods. Around the corner, Sara Bay Marina offers easy access to boat slips and dry storage. While Whitfield Estates continues to be one of Sarasota’s hidden gems with no mandatory HOA or CDD fees. Residents also have the option to join the neighborhood association for just $40 annually, which includes culinary membership privileges at the Sara Bay Country Club. Whether you’re searching for a move-in-ready home, a winter retreat, or a proven investment property, 7311 Broughton Street delivers the perfect combination of style, flexibility, and effortless Florida living.

7311 Broughton Street, Sarasota

$599,000

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

Virtually Staged. Welcome to 138 Holly Avenue, nestled in the highly sought-after Whitfield Estates, where timeless charm meets modern comfort just moments from the sparkling waters of Sarasota Bay. Beautifully renovated from top to bottom, this move-in-ready residence offers 2,187 square feet of thoughtfully designed living space on over a quarter-acre, creating the perfect blend of style, functionality, and everyday luxury. From the moment you step inside, you’ll appreciate the home’s bright, open feel. Expansive sliding glass doors and oversized windows flood the interior with natural light, seamlessly connecting the indoor living spaces to the outdoors. Designer lighting, dimmer switches throughout, and elegant finishes create the perfect ambiance from sunrise to sunset, while the spacious layout offers comfortable living and effortless entertaining. The beautifully updated kitchen is equipped with stainless steel appliances, complemented by quality finishes and an inviting flow into the main living areas. Additional peace of mind comes with a brand-new roof, hurricane-impact windows and doors, and meticulous updates throughout, allowing you to simply unpack and enjoy. Step outside to your private, oversized backyard, where there’s plenty of room to entertain, garden, add a pool, or simply unwind while enjoying beautiful Florida sunsets. It’s an outdoor space designed for relaxing evenings and making lasting memories. Location truly sets this home apart. Just steps from Sarasota Bay, you’re minutes from vibrant downtown Sarasota, Sarasota-Bradenton International Airport, IMG Academy, world-renowned Gulf beaches, waterfront dining, shopping, and entertainment. Around the corner, Sara Bay Marina offers convenient boat slips and dry storage, making it easy to embrace Sarasota’s coveted boating lifestyle. Whitfield Estates remains one of Sarasota’s hidden gems, offering no mandatory HOA and no CDD fees, providing flexibility for full-time residents, seasonal homeowners, or investors alike. An optional $40 annual neighborhood association includes culinary membership privileges at the prestigious Sara Bay Country Club. Whether you’re searching for your forever home, a seasonal retreat, or a smart investment, 138 Holly Avenue offers the perfect balance of location, quality craftsmanship, modern updates, and effortless Florida living—all in one of Sarasota’s most desirable waterfront neighborhoods.

138 Holly Avenue, Sarasota

$608,000

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

Discover this one-of-a-kind Mid-Century Modern home where timeless architecture, natural elements, and tranquil design come together beautifully. This light-filled residence features an open floor plan with 3 spacious bedrooms, 3 full bathrooms, and a versatile flex space with its own private entrance, currently serving as a home office but equally suited as a guest suite, private studio, or in-law accommodations—making it ideal for multi-generational living. Expansive telescoping sliding glass doors create seamless indoor-outdoor living, opening to a fun custom-designed pool and peaceful, Zen-inspired outdoor oasis. The lush backyard offers plenty of room for gardening enthusiasts to create in their own Florida paradise, while two oversized garage bays provide ample space for vehicles, golf carts, hobbies, or additional storage. Clean architectural lines, warm organic finishes, and abundant natural light make this home truly special. Additional highlights include a brand-new roof (2025) and an exceptional location just minutes from downtown Sarasota, world-famous beaches, SRQ Airport, and directly across from the historic Sara Bay Golf & Country Club. Meticulously maintained and unlike anything else on the market, this exceptional home offers timeless style, flexible living, and an unbeatable Sarasota location. Schedule your private showing today!

618 Whitfield Avenue, 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

$555,000

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

Welcome to this charming mid-century Florida rancher nestled in the sought-after waterfront neighborhood of Whitfield Estates — one of Sarasota's most beloved and established communities. Set on a generous 0.29-acre corner lot, this 2-bedroom, 2-bathroom home offers 1,371 square feet of comfortable living space with genuine Florida character and serious income-producing potential. Whether you're searching for a personal retreat or a turnkey investment, this home delivers. Currently active on Airbnb and generating approximately $180 per night, it has already proven itself as a strong short-term rental performer — making it an exceptional opportunity for investors looking to capitalize on Sarasota's thriving tourism market. Inside, you'll find renovated bathrooms that bring a fresh, modern touch to the home's classic bones. The layout is bright and functional, with a warm, welcoming feel that guests and homeowners alike will appreciate. Step outside and enjoy everything that comes with life in Whitfield Estates — a peaceful, established neighborhood with a true sense of community, no HOA, and easy access to the very best of Sarasota. World-renowned Siesta Key Beach, the cultural richness of downtown Sarasota, St. Armands Circle shopping, and the Ringling Museum are all just minutes away. No HOA. Corner lot. Proven rental income. And all the Florida sunshine you could ask for. Offered at $570,000.

138 Pearl Avenue, Sarasota

Whitfield Estates Real Estate

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