Whitfield, FL Homes for Sale with Pool

Deep Water Boating Paradise in Whitfield Estates!Welcome to this exceptional waterfront residence nestled in the desirable West of Trail neighborhood of Whitfield Estates. Boasting expansive, sailboat-depth water frontage with no fixed bridges to the Gulf, this property is a rare find for boating enthusiasts. The composite dock offers multiple slips—along with a 10,000 lb lift and davit.

Andrew Pepper KELLER WILLIAMS ON THE WATER S

This meticulously updated 3-bedroom, 2.5-bathroom pool home, located in the desirable Whitfield Estates, sits on over a quarter-acre lot and seamlessly blends contemporary elegance with timeless mid-century charm. Recent upgrades, including a newer roof (2021), updated windows, and a fully fenced backyard, offer a perfect balance of modern appeal and peace of mind. The home’s fresh exterior paint

Toni Zarghami KW COASTAL LIVING III

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

Ahmad Alnabout 54 REALTY LLC

BOATERS DELIGHT...If you're a boating enthusiast, this property is truly a dream come true! Whether you're planning a day on the water to get away from it all, fishing to catch the BIG one, or just enjoying the Gulf Coast's serene waterways, this location offers unmatched convenience and access. Located on Bowles Creek this fine home is just a few minutes to Sarasota Bay and the Gulf beyond (See

Richard Capps FINE PROPERTIES

Welcome to "Serenity on 7" – Where Coastal Charm Meets Everyday Relaxation.Discover the perfect blend of casual elegance, coastal living, and lasting quality in this completely remodeled retreat, located on the 7th hole of the historic Sara Bay Golf & Country Club. Situated on one of the most sought-after streets in Whitfield Estates, “Serenity on 7” offers timeless style, unmatched

Robert Halbman EXIT KING REALTY

Experience luxury living in this renovated 1926 Whitfield Estates home! Easy to show & go.Unparalleled Location: nestled under a newly trimmed historic banyan tree, this lushly landscaped home with its spacious backyard enjoys a coveted location ‘west of the trail’ and steps from Sarasota Bay, as well as close proximity to the famed and historic Alfred Ringling home.3.5 Bedrooms & 2.5

Angie Ramos COLDWELL BANKER REALTY

Prime location near Sarasota Bay and just 10 minutes to downtown! A rare opportunity to own a newer pool home with no deed restrictions. PLUS- SELLER IS OFFERING $10,000 TOWARDS BUYERS CLOSING COSTS. This versatile property offers the ultimate blend of lifestyle and income potential, zoned for nightly rentals. It's located less than 10 minutes from SRQ Airport and 15 minutes to St Armands Circle

Catie Seip EXP REALTY LLC

Welcome to Sarasota Cay Club, where every day feels like vacation and every night can add to your rental income! This 1 bedroom, 1 bath FIRST FLOOR condo-hotel unit has been COMPLETELY REMODELED and comes FULLY FURNISHED with 2 double beds, stylish finishes, and everything you need to start enjoying (or renting) immediately. With NO MINIMUM RENTAL RESTRICTIONS, you’re free to maximize income

Dan Lussier KELLER WILLIAMS ON THE WATER S

Welcome to your private oasis nestled along the pristine fairways of Sara Bay Golf Club, which boasts a rich history as one of Florida's oldest golf clubs known for its classic layouts. Experience breathtaking views from the comfort of your back yard as the lush landscape blends beautifully into the 15th hole. This 3-bedroom 2.5 bath home has been meticulously maintained and offers many luxury

Misty Jones FLORIDA DREAMS REALTY OF AMI

Endless potential in a prime location!Nestled on an oversized lot of over a quarter acre, this 3 bedroom, 2 bath pool home offers the perfect opportunity to create your ideal Florida retreat or a high performing investment property. With nightly rentals allowed, this home is a rare find for savvy investors or buyers seeking passive income potential.The home features a new roof in

Jessie Bonner SARABAY REAL ESTATE INC

West of the Trail and just steps from Sarasota Bay, this tropical retreat is your chance to own a true slice of Florida paradise.Step into your own private oasis featuring a resort-style pool, tiki hut, and outdoor kitchen, perfect for entertaining or soaking up the sunshine year-round. This 3-bedroom, 2-bath block home offers a functional layout with a 2-car garage and dedicated laundry

Jessie Bonner SARABAY REAL ESTATE INC

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

Jessie Bonner SARABAY REAL ESTATE INC

S-623 TURN KEY! (Everything is included in the sale!) A SECOND-FLOOR CITY VIEW: Newly renovated LVT living area floor with 3" baseboard moldings. Wonderful, fully functional new kitchenette with butcher block countertops and new overhead cabinets (with under-cabinet lighting), two tabletop burners, and a beautiful backsplash. A remote control center mini ceiling fan with light in the Living Room.

Ron Dawson CHARLES RUTENBERG REALTY INC

Turnkey investment opportunity or personal vacation getaway—this fully furnished, renovated 1-bedroom, 1-bath hotel-condo is located in the popular Sarasota Cay Club within the Ramada by Wyndham Sarasota Waterfront Resort. Perfect for short-term or long-term rentals, this unit has no minimum rental restrictions and comes with all utilities included in the HOA fee—electric, cable, internet, water,

Geri Vice RE/MAX HARBOR REALTY

Discover Your Sarasota Waterfront Paradise!Imagine waking up to the gentle sounds of Sarasota Bay, where your private beach meets 100 feet of pristine shoreline. This enchanting 5-bedroom, 4-full, and 2-half-bath residence masterfully combines timeless charm with modern comforts, creating the ultimate waterfront haven.For those who cherish life on the water, this property is unparalleled.

Lisa Kartz SARABAY REAL ESTATE INC

This beautifully updated first-level condo at the Sarasota Cay Club offers easy access and comes with season bookings! Featuring brand new flooring, new A/C, fresh paint and modern furnishings, this unit is located within the Ramada by Wyndham Sarasota Waterfront Resort. The condo is perfect for short-term rentals with no minimum leasing restrictions, allowing you to use it for your own

Ingrid Caruso COLDWELL BANKER REALTY

Welcome to Las Casas, a pet-friendly boutique 55+ community of just 22 detached villas, located 8 miles from downtown Sarasota and the Gulf Coast beaches. Nestled on a private cul-de-sac backing onto McArthur Park, this villa offers excellent curb appeal and a peaceful setting. Recently updated, the home features new luxury vinyl plank flooring and has been freshly painted inside and out. The

Yvette Sellyn COLDWELL BANKER REALTY

Large price reduction, Stunning Newly Renovated 5-Bedroom Home with a Swimming Pool and Oversized Three-Car Garage. This newly renovated property offers everything you need and more. With five spacious bedrooms and three full bathrooms, there's plenty of room for family and guests. The three-car garage provides ample space for vehicles, storage, and hobbies. Dive into luxury with your own private

Lee Brewer RE/MAX ALLIANCE GROUP

Under Construction. The Abaco Model is the perfect Sarasota Luxury home sporting 4,343 sf of living space and 6,273 sf under roof. Upon arrival through the 10 ft high Iron Front Doors, the Foyer provides a direct view through the house to the pool and canal at the rear of the backyard. The oversized Great Room has ample space for entertaining and includes stained cypress beams, a gas fireplace

Colton Nagler RKW BUTTON

Opportunity Knocks in Shadybrook Village!Unlock the potential of this spacious 3-bedroom, 2.5-bathroom two-story condo located in North Sarasota. Nestled in the established Shadybrook Village subdivision, this unit is ready for a full remodel—perfect for investors or buyers looking to customize their dream space from the ground up.Enjoy generous square footage across two levels, with

Frank Zeckel COLDWELL BANKER REALTY

Price improvement! Now priced more competitively, this home offers generous square footage and strong value compared to similar homes currently on the market. Located just minutes from the Gulf beaches and downtown Sarasota, this updated 3 bedroom, 2.5 bath condo offers well maintained living space with recent upgrades. A brand new roof and a newly constructed private wood deck, both completed in

Kahlan Shull PREFERRED SHORE LLC

Investor’s Dream in Prime Sarasota Location – Just One Block from the Bay. Opportunity awaits just steps from Sarasota Bay in the highly sought-after Ringling Museum district. This spacious 3-bedroom, 3 full bath, 2 half bath home with a private in-law suite is situated on a rare corner double lot, offering tremendous upside potential for investors, developers, or end users. The property already

Michelle Ward COMPASS FLORIDA LLC

OWNER FINANCING AVAILABLE!!Welcome to Shadybrook Village - and enjoy your cozy townhouse with plenty of room for family and friends! When you walk inside you are welcomed to an updated kitchen with stainless steel appliances and granite countertops. Laminate flooring covers the entire first floor; the living area is open and spacious, and the dining room sits right next to the kitchen.

Ken Anderson RE/MAX ALLIANCE GROUP