Whitfield Estates Real Estate

RARE OPPORTUNITY IN WHITFIELD ESTATES! Discover one of the few remaining vacant homesites in one of Sarasota's best-kept secrets! Offered at just $189,000, this unique property presents an exceptional opportunity to create your own piece of paradise in the highly desirable Whitfield Estates neighborhood. Perfectly positioned along the picturesque Sara Bay Country Club golf course, this distinctive homesite offers beautiful golf course views from the front and a peaceful, natural waterfront setting along the rear, where a tranquil creek winds through the neighborhood. Imagine enjoying your morning coffee overlooking the greens, spending an afternoon kayaking or paddleboarding along the waterway, or simply embracing the natural beauty of Old Florida living. Surrounded by established homes, mature landscaping, and the charm that makes Whitfield Estates so special, this property offers a rare chance to build in a neighborhood where vacant land is nearly impossible to find. Whether you're envisioning a custom Florida retreat, a seasonal getaway, or an investment opportunity, the possibilities are worth exploring! Located in Whitfield Estates, one of Sarasota's hidden gems, residents enjoy NO mandatory HOA fees or CDD fees, along with flexible rental opportunities, including nightly rentals, subject to applicable regulations. Optional membership in the Whitfield Ballentine Manor Association is just $40 annually and includes culinary membership privileges at the prestigious Sara Bay Country Club, currently undergoing an exciting renovation with plans to reopen in 2027. Boating enthusiasts will appreciate nearby SaraBay Marina, offering convenient access to boat slips and dry storage. Ideally situated just minutes from Sarasota Bay, SRQ International Airport, downtown Sarasota, IMG Academy, world-famous Gulf beaches, championship golf, waterfront dining, shopping, and entertainment. Opportunities like this are few and far between! Don't miss your chance to secure one of the last remaining vacant homesites in Whitfield Estates and bring your vision of Florida living to life!

423 Magellan Drive, Palm Aire

$299,900

A4709487 MLS

New Price. Big Opportunity. Seize the Opportunity! Discover an exceptional opportunity to create your ideal Florida lifestyle on this spacious 0.26-acre homesite in the established Whitfield Estates neighborhood. Located on Westmoreland Drive, this buildable lot offers partial views of Sarasota Bay and ample space to design a custom home with a pool, outdoor entertaining areas, and lush tropical landscaping. There are two new builds: 1.) across the street, and 2.) to the south of the lot on the bay. Enjoy the freedom of no HOA restrictions, along with access to public water and sewer. Boating and outdoor enthusiasts will appreciate the nearby SaraBay Marina and county kayak launch, providing convenient access to Sarasota's beautiful waterways. Location adds to the appeal! Just minutes from Sarasota Bradenton International Airport, University Parkway, the renowned Ringling Museum of Art, and vibrant downtown Sarasota, you'll enjoy easy access to exceptional dining, shopping, cultural attractions, and Gulf Coast recreation. Offered at $299,900, this homesite presents an attractive opportunity for custom-home buyers, builders, and investors seeking a desirable Sarasota location without the premium price of direct waterfront property. Bring your vision and build the Florida lifestyle you've been dreaming of! Buyer to verify flood zone, insurance, setbacks, and all building requirements with the county.

7510 Westmoreland Drive, Palm Aire

$630,000

3 Beds ⋅ 3 Baths ⋅ TB8558285 MLS

FULLY FURNISHED COASTAL PARADISE IN SARASOTA! Discover this beautifully decorated two-story home featuring 3 bedrooms, 2.5 bathrooms, a private screened-in pool, and a two-car garage. Designed with charming beach-inspired decor, coastal furnishings, nautical accents, and relaxing ocean-inspired colors, this home offers the perfect Florida lifestyle. ALL EXISTING FURNITURE AND DECOR ARE INCLUDED IN THE SALE! Step inside to enjoy soaring ceilings, abundant natural light, spacious living and dining areas, and beautiful tile flooring. The kitchen features elegant cabinetry, stainless steel appliances, generous counter space, and a breakfast bar. Additional highlights include comfortable bedrooms, a versatile game room, and a dedicated laundry room. YOUR PRIVATE BACKYARD OASIS AWAITS! Enjoy a sparkling screened-in swimming pool, perfect for pool volleyball and basketball! Relax or entertain on the spacious covered patio and expansive paver deck, surrounded by tropical landscaping and a fully fenced backyard offering privacy. Conveniently located near Sarasota Bay, Gulf Coast beaches, shopping, dining, and Sarasota Bradenton International Airport. FULLY FURNISHED, BEAUTIFULLY DECORATED, AND READY TO ENJOY! SCHEDULE YOUR PRIVATE SHOWING TODAY!

354 Montgomery Avenue, Palm Aire

$515,000

3 Beds ⋅ 2 Baths ⋅ TB8556568 MLS

FULLY FURNISHED POOL HOME IN DESIRABLE WHITFIELD ESTATES! Welcome to your private Florida oasis! This beautifully updated 3-bedroom, 2-bathroom home sits on a spacious corner lot less than a mile from Sarasota Bay. Featuring gorgeous porcelain tile flooring throughout, vaulted ceilings, a stunning stone fireplace, and a spacious living and dining area. The kitchen offers wood cabinetry, stainless steel appliances, and a charming breakfast nook. The primary suite features a private bathroom with a walk-in shower, while the additional bedrooms feature stylish decorative accents. THE BACKYARD IS A TRUE SHOWSTOPPER! Enjoy an exceptionally long lap-style swimming pool with color-changing lights, a spacious paver deck, lush tropical landscaping, privacy fencing, and a covered patio perfect for entertaining. Additional features include a two-car garage and extended driveway. Conveniently located near Sarasota’s beautiful beaches, shopping, dining, marinas, and Sarasota Bradenton International Airport. SOLD FULLY FURNISHED, WITH ALL EXISTING INTERIOR FURNISHINGS AND CONTENTS INCLUDED AS AGREED UPON IN THE PURCHASE CONTRACT! An incredible opportunity to enjoy the Florida lifestyle!

520 Mcarthur Avenue, Palm Aire

$439,000

3 Beds ⋅ 2 Baths ⋅ A4708933 MLS

Welcome to classic Mid-Century Modern living in Whitfield Estates! Tucked west of the Trail on a quiet street lined with mature oaks, this updated home sits just moments from the Bay and about halfway between the Sarasota Bayfront and Bradenton's downtown Riverwalk, so the best of both cities is always an easy drive away. Step inside and you'll find a home that's all about the light. Walls of windows and sliding glass doors fill every room with sunshine and blur the line between indoors and out, just the way Mid-Century design was meant to be enjoyed. Arrivals feel special here. A sweeping horseshoe driveway frames the landscaped front yard and leads to a generous porte cochère, so guests can step out covered from sun and rain and roll right back out the other side. The big-ticket updates are already done: insulated double-pane windows, a new roof (2022), a rated garage door (2018), AC (approx. 2017), and a water heater (2023). The remodeled kitchen is a joy to cook in and comes with a charming coffee nook for slow mornings. Out back, the lanai is ready for your green thumb, with space to fill with potted plants, herbs, and flowers. The large yard offers room to roam and comes with a swing set already in place.

126 Holly Avenue, Palm Aire

$3,250,000

5 Beds ⋅ 4 Baths ⋅ A4703035 MLS

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, Palm Aire

$510,000

3 Beds ⋅ 2 Baths ⋅ A4702875 MLS

PRICE IMPROVED | Income-Producing Golf Course Pool Home at Sara Bay This one is already earning. Set on the 18th hole of Sara Bay Country Club, this 3-bedroom, 2-bath pool home is currently operating as a successful short-term rental, and it has performed well on annual leases too. That gives you flexibility in how you run it. With nearly 2,000 sq. ft. on an oversized .42-acre lot, it's a turnkey investment that can convey fully furnished if desired, so you can step in with income from day one. The covered lanai and sparkling pool look straight out over the fairway to the west, so sunsets are part of the daily routine. The space is private, peaceful, and usable year-round, exactly what guests book for and what you'll want when you're in town yourself. Inside, a split floor plan gives the primary suite and guest rooms their own space. Two living areas add room for hosting, working from home, or giving renters space to spread out. Natural light and thoughtful updates keep the home move-in and rent-ready. The location makes it easy to book and easy to enjoy: about 5 minutes to SRQ Airport, under 15 minutes to downtown Sarasota, and close to beaches, golf, dining, and the arts. Keep it on the short-term calendar, switch to annual tenants, or block off your own winter weeks. It's a vacation home that pays its own way. SELLER INCENTIVE: Seller is offering a 1% closing cost credit or assistance buying down your interest rate. Ask for details.

433 Whitfield Avenue, Palm Aire

$399,000

2 Beds ⋅ 2 Baths ⋅ A4702215 MLS

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.

811 Alderwood Way, Palm Aire

$5,500,000

6 Beds ⋅ 6 Baths ⋅ A4695898 MLS

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 / in-law retreat 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, Palm Aire

$1,700,000

A4696164 MLS

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, Palm Aire

$1,700,000

3 Beds ⋅ 2 Baths ⋅ A4696134 MLS

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, Palm Aire

$540,000

2 Beds ⋅ 2 Baths ⋅ A4691706 MLS

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, Palm Aire

Whitfield Estates Real Estate

Newest Listings in Whitfield Estates

How much is your home worth?

How much is your home worth?