Whitfield Estates Real Estate

1 Beds ⋅ 1 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

TURNKEY, UPDATED CONDO-HOTEL OPPORTUNITY IN SARASOTA'S WATERFRONT COMMUNITY! Enjoy resort-style living in this beautifully refreshed second-floor studio/efficiency at the Ramada by Wyndham Sarasota Waterfront. C216 has been thoughtfully updated with new flooring, fresh paint, all-new furnishings, and recessed LED ceiling lighting, creating a bright, clean and inviting space that is ready for personal enjoyment or rental use. Located in one of the community's most desirable buildings for convenient access to the resort amenities, this unit puts you close to the waterfront marina, pool, on-site dining and tiki bar. Residents and guests can enjoy a scenic waterfront setting, resort-style pool, fitness center, business center, waterfront walkways and other amenities. Flexible rental options provide added versatility, with the opportunity to use the property as a vacation retreat, personal getaway or investment property. On-site management is available, while owners also have the flexibility to manage their own rental. Currently offered as the best value among the available units in the community, C216 presents a compelling opportunity to own an updated, turnkey condo-hotel in a desirable Sarasota location. Conveniently located near shopping, dining, entertainment, beaches and Sarasota-Bradenton International Airport, this property offers an exceptional combination of amenities, flexibility, value and accessibility. Don't miss the opportunity to own at one of Sarasota's amenity-rich waterfront destinations. Schedule your private showing today!

7150 N Tamiami Trail Unit C216, 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

$529,000

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

NEW PRICE! 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

$415,000

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

$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

$540,000

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

$429,000

2 Beds ⋅ 1 Baths ⋅ Whitfield Estates SubDv. ⋅ 34207 Zip Code

Live the Florida waterfront lifestyle at an exceptional price point with this charming 1950s block bungalow on Bowlees Creek. This 2 bedroom, 1 bathroom home blends classic character with thoughtful updates, including a brand new metal roof, new HVAC system, and updated luxury vinyl flooring throughout for easy, low maintenance living. The bright, coastal inspired kitchen features white quartz countertops, a tile backsplash, and coastal style cabinetry, creating a fresh and inviting space to gather. Step outside to a peaceful screened in patio where you can relax, unwind, and take in the tropical setting overlooking the canal and spacious backyard, with plenty of room to add a pool. Spend your days enjoying the water right from your backyard. Tie off at your dock, hop on a friend’s boat, and cruise out to Sarasota Bay, or keep it simple with kayaking, paddleboarding, and soaking in the laid back waterfront lifestyle. A shell gravel drive and fresh exterior paint add to the home’s easygoing coastal charm. Conveniently located with easy access to Anna Maria Island, Siesta Key, and surrounding Gulf beaches, this property offers the perfect opportunity for a full time residence, vacation getaway, or investment in one of Florida’s most desirable coastal areas. Buyer to verify dock and water access details. PRICED UNDER RECENT APPRAISED VALUE!

704 69th Avenue W, Bradenton

$525,000

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

Welcome to West of the Trail in sought after Whitfield Estates, a beautifully remodeled home on a quarter-acre lot offering style, flexibility, and proven income potential. Whether you’re a first-time homebuyer, savvy investor, or searching for the perfect second home or vacation retreat, this property checks all the boxes. Inside, the home has been thoughtfully transformed with a fresh, elevated feel that blends comfort and character. The updated kitchen offers abundant cabinetry, brand new stainless steel appliances, creating a bright, inviting layout that flows easily into the main living spaces. Both bathrooms have been tastefully renovated, and the overall design feels crisp, cohesive, and truly move-in ready. A new roof installed in 2020 adds additional peace of mind. The spacious screened lanai overlooks a large backyard with room to relax, entertain, or enjoy the Florida sunshine. Furniture is available for purchase, offering a potential turnkey opportunity for those looking to step right into a primary residence or rental. Located just minutes from downtown Sarasota, SRQ Airport, top dining and shopping, and our world-famous Gulf beaches, this home offers convenience without sacrificing charm. An added bonus: this is an active income-producing property with future bookings already in place, making it a rare opportunity for buyers looking for immediate rental potential. And with no flood zone to worry about, it offers even more peace of mind. Whitfield Estates is loved for its tree-lined streets, bay front sunsets, and exceptional location. The neighborhood also offers a voluntary association for just $30/year, which includes culinary access to the Sara Bay Country Club. Boaters will appreciate the close proximity to SaraBay Marina with boat slips and dry storage nearby, making it easy to enjoy life on the water. With optional amenities and no mandatory HOA fees, you’ll enjoy flexibility without added restrictions. This is your chance to own a beautifully updated home in one of Sarasota’s most established neighborhoods, ideal as a primary residence, seasonal getaway, or smart investment. Schedule your private tour today!

7746 Westmoreland Drive, Sarasota

$610,000

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

The purchase of a home begins with an offer. 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 owner would love to see an offer from you that results in a contract. 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

Whitfield Estates Real Estate

Newest Listings in Whitfield Estates