Whitfield Estates Homes with Private Mailbox Exterior Features

Whitfield Estates Homes with Private Mailbox Exterior Features

Welcome to Whitfield Estates, a hidden gem nestled in the heart of Palm Aire, Florida, within the scenic Manatee County. This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and everyone in between.

Whitfield Estates features beautifully designed homes that exude character and warmth, with many boasting private mailbox exterior features that add a touch of individuality to each residence. Imagine coming home to a picturesque street lined with vibrant landscaping and unique architectural styles, all while enjoying the comfort of your own private mailbox—an emblem of pride and personal touch in your new home.

The community is strategically located, providing easy access to major highways, shopping centers, and recreational areas. Whether you’re looking to indulge in retail therapy at nearby boutiques, savor a meal at local eateries, or explore the beautiful parks and golf courses that Palm Aire has to offer, everything you need is just a stone’s throw away.

Whitfield Estates is not just about beautiful homes; it’s about a lifestyle. Residents enjoy a close-knit community atmosphere, where neighbors become friends and memories are made. The serene surroundings, combined with the vibrant energy of nearby attractions, create the perfect backdrop for your new life in Florida.

Discover the charm of Whitfield Estates today and explore the possibilities of calling this delightful community your home. Experience a lifestyle where comfort meets convenience, and every day feels like a vacation!

Newest Whitfield Estates Homes with Private Mailbox Exterior Features

$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
$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
$449,000
4 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
!!! Massive Price Reduction !!! ****THIS PROPERTY IS LOCATED IN AN OVERLAY DISTRICT - SO, WHILE NO HOA, MANATEE COUNTY HAS JURISDICTIONS PERTAINING TO ATTRIBUTES OF THE HOME DUE TO ITS LOCATION IN A HISTORIC DISTRICT. BOTH THE OVERLAY RESTRICTIONS AND THE GIS MAP ARE ATTACHED FOR VIEWING - ASK YOUR REALTOR FOR A COPY >> PLEASE READ THESE BEFORE SCHEDULING A SHOWING AS IT INCLUDES RESTRICTIONS SUCH AS COMMERCIAL VEHICLE PARKING, RV AND BOAT PARKING**** NO FLOOD * NO CDD * VOLUNTARY $40/YEAR ASSN PROVIDES FINE DINING ACCESS AT Sara Bay Country Club. AVIATION ENTHUSIASTS TAKE NOTE! This bright and spacious 4 bedroom, 3 bathroom + den + bonus room contemporary home sits on an oversized fenced corner lot and offers soaring ceilings, abundant natural light, and move-in-ready peace of mind. RECENT UPGRADES INCLUDE: Hurricane impact windows (2024) Solar panels (2024) Roof (2016) Hot water heater (2025) Refrigerator (2024) Dishwasher (2019) Garbage disposal (2021) Washer (2019) Dryer (2020) HVAC (2017) Irrigation pump (2023) Located in sought-after Whitfield Estates, this unique neighborhood is in Manatee County while maintaining a Sarasota address. Conveniently positioned near Sarasota-Bradenton International Airport, residents enjoy exceptional access to everything the area has to offer. Neighborhood highlights include: 5-minute Uber to the airport 5-minute drive to multiple colleges and universities 12-minute drive to downtown Sarasota 20-minute drive to the white sands of Lido Key Beach Not a golfer but love upscale dining? Whitfield Estates residents may choose to pay the optional $40/year HOA fee, granting eligibility for a culinary membership at the exclusive Sara Bay Country Club. With its size, location, and convenience, this property also presents a strong opportunity for short-term rental income, Airbnb potential, or student housing investment.

7303 Manatee Street, Sarasota
$535,000
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
$549,000
2 Beds ⋅ 1 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
West of the Trail in Whitfield Estates, this mid-century gem captures the charm and character that define classic Florida architecture. From the original terrazzo floors to the preserved kitchen design, the home reflects the clean lines and simplicity that make mid-century residences so desirable. The spacious great room with fireplace serves as the heart of the home, offering natural light and comfortable gathering space while maintaining its authentic architectural appeal. Situated on a rare double lot, the property offers exceptional flexibility and long-term potential. Expand the footprint, design a custom pool, add a detached garage, or simply enjoy the privacy and space that are increasingly rare west of the Trail. Located on sought-after Westmoreland Drive, just across from multi-million-dollar bayfront estates, this property blends historic charm with premier positioning. Residents of Whitfield Estates have the unique opportunity to enjoy dining at nearby Sara Bay Country Club. For an optional annual HOA fee of just $35, owners may obtain a culinary membership granting full access to the clubhouse for dining and social events (golf privileges not included; membership subject to club approval). Minutes to Sarasota Bay, IMG Academy, SRQ Airport, and downtown Sarasota — this is authenticity, land, and lifestyle in one of the area’s most established West of the Trail neighborhoods.

7549 Westmoreland Drive, 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
$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
Start Your Search