Whitfield Estates Homes with Private Pool type

Whitfield Estates Homes with Private Pool type

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Newest Whitfield Estates Homes with Private Pool type

$620,000
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
$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
$610,000
3 Beds ⋅ 4 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
The significant price reduction on this home reflects the owner's awareness of the costs of updating the kitchen and bathrooms. They are all completely functional but could use refreshing. The neighborhood you live in is as important to your lifestyle as the home you select. Whitfield Estates is reminiscent of days gone by. Over 100 years old, it feels like a true neighborhood, with dogwalkers, joggers and smiling faces always ready with a warm and welcoming greeting. Without the constraints of an HOA there is a live and let live atmosphere. The rules and regulations are minimal, enforced by Manatee County and should be read by all prospective buyers. The voluntary neighborhood association is a mere $40.00 annually and provides you with 6 meetings a year, community events and a dining card that may be used at the Sara Bay Country Club. Perfectly positioned on a generous corner lot with a backyard that overlooks the 14th green and 15th Tee box, your privacy is assured. This property offers rare privacy and additional green space that enhances a relaxed and peaceful existence. The pavered driveway is large enough for visitors to easily park and once you step inside, you’ll immediately notice how much larger the home feels than its square footage suggests. The open plan living room has a propane fireplace and can be configured to suit your lifestyle. The dining area can host a dinner for 12 or more or can serve as a small, intimate eating area providing more space for reading and television nooks. The bright, open split floor plan and sliders create an airy, spacious ambiance that allows for indoor/outdoor living and entertaining. The home has a rambling, family friendly layout and more closets and storage space than you could ever need. There are two primary ensuite bedrooms as well as a mother-in-law suite with a private bathroom. The oversized garage and inside laundry room are in addition to the golf cart garage that leads straight out to the course. The screened lanai boasts a heated pool and covered entertainment area with a fenced dog run to the side. A shed is tucked away on the other side that can house your pool equipment and lawn tools. The roof was replaced in 2019, the electrical panel in 2016, one A/C unit in 2007 and the second in 2016. The home has been lovingly maintained and painted in subtle colors. It is move-in ready and just waiting for you to enjoy.

844 Magellan 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
$669,999
3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
Come live where everyone goes on vacation! This is a beautiful breathtaking 3 bedrooms, 2.5 bathroom, Sarasota pool home in Whitfield Estates. Some of the features include private screened pool and lanai. Huge private backyard. This home was fully updated with new appliances, Hvac was replaced in 2025, roof was replaced last year, water heater and water filter was replaced 2 years ago, new pavers on the driveway, and fully remodeled bathrooms. This home is 2 blocks away from the Sarasota bay! 17 minutes away from Lido Key beach! 10 minutes away from the airport, shopping centers and so much more. This home is currently not vacant and requires appointments to see it.

7324 Phillips Street, Sarasota
$500,000
3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
West of The Trail with endless potential in Prime Location – Nightly Rentals Allowed! Welcome to this charming 3-bedroom, 2.5-bath Pool home in the highly desirable Whitfield Estates neighborhood where opportunity meets location! Whether you’re looking for your first home, a winter escape, or an income-producing Airbnb, this property is a rare find with no CDD, no monthly HOA, and the flexibility for nightly rentals. Set on a spacious quarter-acre, fully fenced lot, the home features a large pool, perfect for soaking up the Florida sunshine. The half bath is conveniently located poolside, ideal for entertaining guests outdoors. Inside, you’ll find a thoughtful layout with a primary suite addition that includes two separate walk-in closets and a cozy sitting area. The first guest room offers impact sliding doors leading directly to the pool, while an additional family/bonus room provides extra flexibility for a game room, office, or guest space. While the home retains some original finishes, including carpet, it’s bursting with potential just waiting for your personal touch and updates. The whole house was repiped in 2020 and roof replaced 2015. AC is 2014. Located between Downtown Bradenton and Downtown Sarasota, Whitfield Estates places you minutes from Sarasota Airport, IMG Academy, St. Armand’s Circle, Anna Maria Island, Lido Key, and all the fine dining, shopping, and entertainment the Gulf Coast has to offer. Enjoy the perks of a voluntary neighborhood association with no mandatory fees. For just $30/year for access to a culinary membership at SaraBay Country Club. Boaters will love being close proximity from SaraBay Marina, offering boat slips and dry dock storage. Whether you’re dreaming of a Florida beach house, a rental investment, or a full-time residence, this home is your blank canvas in one of the area’s most sought-after communities.

139 Adair Avenue, Sarasota
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