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619 Saint Andrews Drive, Sarasota
$499,000
3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
RARE FIND! Every once in a while, a property comes along that truly stands apart. This 3 Bedroom split plan home is situated on an expansive half acre lot and offers a wonderful blend of classic Florida character, thoughtful updates and the space and privacy that are increasingly difficult to find. In 2026, the HVAC, driveway and fencing were all given an upgrade and the home has tile and laminate flooring throughout. The roof was replaced in 2019 and this home has a large screened backyard patio that overlooks the beautiful in ground pool and gazebo. Enjoy sunny afternoons lounging by your private swimming pool, entertaining family and friends or simply taking in the peaceful surroundings of your spacious backyard.  The location is hard to beat, sitting just between Sarasota and Bradenton, residents enjoy easy access to the Sarasota Bradenton International Airport and both Sarasota and Bradenton's vibrant downtown areas. With its generous half-acre setting, private pool, charming surroundings and desirable location, this property presents an exceptional opportunity to enjoy the character and lifestyle that make Whitfield Estates so special. Come and discover the timeless appeal of this historic Sarasota-area neighborhood rich in character and architectural charm, this established community is known for its beautiful mature landscaping, distinctive homes, and connection to the historic Sara Bay Country Club, home to a renowned Donald Ross-designed golf course that has been part of the area’s legacy for generations. Ideally situated between Sarasota and Bradenton, Whitfield Estates offers convenient access to waterfront recreation, cultural attractions, dining, shopping and the Gulf Coast’s renowned beaches. A wonderful opportunity to experience authentic Florida living in a neighborhood with a story all its own.

619 Saint Andrews Drive, Sarasota
338 Whitfield Avenue, Sarasota
$399,000
2 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
WHERE ELEVATED VALUE MEETS UNRIVALED COASTAL LIVING - Tucked away in the historic, tranquil enclave of Whitfield Estates, this private sanctuary delivers the rare convergence of generous land, secluded serenity, and effortless connectivity. Situated moments from the legendary Donald Ross-designed Sara Bay Country Club, residents enjoy immediate access to deep-water marinas, the Sarasota-Bradenton International Airport, vibrant downtown dining, and world-class Gulf beaches—all enriched by the prestige of a Sarasota address. An optional $30 annual association fee opens the door to exclusive community events and dining privileges at historic Sara Bay, adding an exceptional social dimension to this coastal retreat. Connected to central water and sewer with no septic system, the residence offers absolute simplicity and modern reliability. Constructed of solid concrete block and resting high and dry at an approximate 20-foot elevation in Non-Flood Zone X, the single-story residence is framed by a sweeping circular drive and fully fenced grounds. Structural and mechanical investments include: AC (2019 all in one exterior unit), March 2013 dimensional shingle roof, tenting completed in 2022 by Fahey Pest Control with rebuilt overhangs, and comprehensive storm protection from April 2021 featuring double-pane PGT impact sound-reduction windows, impact sliders, and an upgraded front entry door. Critical infrastructure has been thoroughly modernized, featuring complete overhead ceiling re-plumbing to eliminate under-slab supply lines, an upgraded 200-amp electrical service panel (2017), a brand-new water heater (2022), and recently certified backflow plumbing servicing (August 2024). Inside, the home embraces classic Florida indoor-outdoor living through an open, split-floor-plan great room where pocketing glass sliders in every room—including the primary suite, living/dining/kitchen area and guest en suite—dissolve the boundary to the outdoors. The heart of the home centers on an expansive chef’s kitchen featuring an open space (remodeled in 2002), polished stone countertops, updated cabinetry, a contemporary range hood, comfortable four-person bar seating, and premium stainless steel appliances, highlighted by a built-in NewAir wine refrigerator. The thoughtfully designed layout provides two private ensuite bedrooms, a dedicated laundry space with a stacked washer and dryer, and seamless access to a full exterior pool bath complete with a walk-in shower (as part of the 2nd bedroom ensuite). An outdoor oasis is tailored for private, effortless entertaining, centered around a northwest-facing, approximately 6-foot-deep private swimming pool professionally restored in March 2020, enclosed by a newer screened cage, covered lanai, and secondary sun terrace. Complementing this Florida ranch home is an extraordinary level of ownership freedom, free from deed restrictions, HOA mandates, or CDD fees. The expansive grounds easily accommodate on-site parking for large boats, trailers, or RVs, while a highly lucrative rental policy allowing monthly leases up to 12 times per year makes this an irresistible primary residence, seasonal getaway, or high-performing portfolio addition.

338 Whitfield Avenue, Sarasota
438 Whitfield Avenue, Sarasota
$709,900
3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
TURNKEY FURNISHED, INCOME-PRODUCING SARASOTA POOL HOME! Discover an exceptional investment opportunity with this beautifully updated 3-bedroom, 2-bath residence offering 1,915 square feet of living space on an expansive .36-ACRE LOT! Currently operating as a successful vacation rental with over $72,000 in gross rental bookings for Jan-Dec 2026, this property offers an attractive opportunity for investors looking to expand their portfolio, while also serving as an ideal seasonal retreat or year-round residence. With no mandatory HOA fees or HOA rental restrictions, this home offers flexibility for its next owner. Step inside to an inviting split-bedroom floor plan featuring vinyl flooring throughout the main living areas, an updated kitchen with granite countertops, modern cabinetry, and stainless steel appliances, along with updated bathrooms and a dedicated laundry room. The spacious primary suite features a private ensuite bathroom and walk-in closet, offering a comfortable retreat. Major improvements include a new roof (2021), HVAC system (2025), impact-resistant windows, and an impact-rated garage door, providing added peace of mind and long-term value. The true highlight of this property is the incredible outdoor living space! Step outside to your own private backyard oasis featuring a heated swimming pool, a screened pool enclosure updated in 2021, and an elegant pine wood ceiling accent over the covered lanai. Enjoy outdoor dining with seating for eight, additional lounge areas, and plenty of space to relax or entertain. The fully fenced backyard sits on an oversized .36-acre lot, offering exceptional room to further enhance the outdoor experience with additional recreational amenities, games, or entertaining areas. The attached two-car garage features a 2023 mini-split A/C system and is currently utilized as a recreational and game room, providing additional versatility. Conveniently located near Downtown Sarasota, Lido Beach, Siesta Key, Anna Maria Island, Bradenton Beach, and abundant shopping, dining, golf, and entertainment options, this property offers easy access to some of the Gulf Coast's most desirable destinations. Sold completely turnkey furnished, including furniture, décor, televisions, kitchenware, linens, and outdoor furnishings, this home offers a seamless opportunity for its next owner. Whether you're seeking an established income-producing property, a Florida vacation getaway, or primary residence, this Sarasota pool home delivers an outstanding combination of location, flexibility, and lifestyle!

438 Whitfield Avenue, Sarasota
139 Adair Avenue, Sarasota
$499,000
3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
**BRAND NEW ROOF! JUST STEPS FROM SARASOTA BAY!** Discover the possibilities at 139 Adair Avenue, a spacious 3-bedroom, 2.5-bath pool home offering over 2,000 square feet of living space on a quarter-acre lot in the highly desirable Whitfield Estates neighborhood. Located just steps from Sarasota Bay, this property offers an incredible opportunity to create something truly special in one of Sarasota's most established communities. Featuring a generous floor plan, multiple flexible living spaces, and a private screened-in pool, this home offers the space and versatility today's buyers are looking for. An additional bonus room with sliding glass doors provides direct access to the pool and patio, creating a wonderful extension of the home's living and entertaining areas. The primary suite features an adjoining bonus room and additional walk-in closet, offering exciting possibilities for customization, including the potential to reconfigure the space into a fourth bedroom or private guest suite. An additional poolside bathroom space provides even more potential for future improvements. With its substantial square footage, functional layout, and desirable location, this home is a fantastic opportunity for buyers looking to bring their own vision to life. Whether you choose to enjoy the home as it is or transform it with modern updates, the possibilities are endless! Tucked away **WEST OF THE TRAIL** in Whitfield Estates, one of Sarasota's hidden gems, residents enjoy **NO MANDATORY HOA OR CDD FEES** and flexible rental possibilities, 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 Sara Bay Marina, offering convenient access to boat slips and dry storage. Ideally located just minutes from downtown Sarasota, Sarasota Bradenton International Airport, Sarasota Bay, IMG Academy, beautiful Gulf Coast beaches, championship golf, waterfront dining, shopping, and entertainment. Whether you're searching for a spacious primary residence, an investment opportunity, a winter retreat, or the perfect canvas to design your dream home, **139 Adair Avenue offers the space, location, and possibilities to make it your own.** Schedule your private showing today!

139 Adair Avenue, Sarasota
844 Magellan Drive, Sarasota
$599,000
3 Beds ⋅ 4 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
GOLF COURSE VIEWS, GENEROUS LIVING SPACE & AN OVERSIZED HALF-ACRE LOT IN WHITFIELD ESTATES! Welcome to 844 Magellan Drive, where spacious interiors, beautiful surroundings, and endless possibilities come together in one of Sarasota's most established neighborhoods. Perfectly positioned along the scenic fairways of Sara Bay Country Club, this 3-bedroom, 3.5-bath residence offers 2,479 square feet of living space, a screened-in swimming pool, a two-car garage, and a separate golf cart garage. From the moment you arrive, you'll appreciate the home's expansive footprint, mature landscaping, and inviting setting. Inside, generous room sizes and a versatile floor plan provide an abundance of space for both everyday living and entertaining. The oversized living area features beautiful wood flooring, a charming fireplace, and plenty of natural light, while the exceptionally spacious kitchen offers extensive cabinetry, generous counter space, a center island, and endless potential to create the kitchen of your dreams. The thoughtfully designed bedroom layout includes two generously sized en-suite bedrooms, offering flexibility and privacy for family members and guests alike. The primary suite features ample space, dual closets, and a private bath. Throughout the home, you'll find the kind of room sizes and storage opportunities that are increasingly difficult to find. Step outside to your own private Florida retreat! The screened-in swimming pool overlooks the lush greenery and picturesque fairways of Sara Bay Country Club, creating a peaceful backdrop for morning coffee, afternoon swims, or evening relaxation. Situated on approximately half an acre, the property also features a separately fenced side yard, ideal for pets, along with a dedicated golf cart garage for added convenience. Notable improvements include a 2019 roof, updated impact windows, a 2016 electrical panel, and two HVAC systems installed in 2016 and 2007. With its substantial square footage, generous lot size, and desirable golf course setting, this home presents an exceptional opportunity to personalize a property with tremendous potential. Tucked away in Whitfield Estates, one of Sarasota's hidden gems, residents enjoy no mandatory HOA or CDD fees and flexible rental possibilities, including short-term 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 Sara Bay Marina, offering convenient access to boat slips and dry storage. Ideally located just minutes from downtown Sarasota, Sarasota Bradenton International Airport, Sarasota Bay, IMG Academy, beautiful Gulf Coast beaches, championship golf, waterfront dining, shopping, and entertainment. Whether you're searching for room to spread out, a peaceful golf course retreat, or the opportunity to create your dream Florida home, 844 Magellan Drive offers the space, setting, and possibilities to make it your own. Schedule your private showing today!

844 Magellan Drive, Sarasota
354 Montgomery Avenue, Sarasota
$630,000
3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
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, Sarasota
520 Mcarthur Avenue, Sarasota
$515,000
3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
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, Sarasota
126 Holly Avenue, Sarasota
$429,000
3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
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, Sarasota
7418 Westmoreland Drive, 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
433 Whitfield Avenue, Sarasota
$510,000
3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
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, Sarasota
7524 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 / 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, Sarasota
7538 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
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
704 69th Avenue W, Bradenton
$389,000
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
7322 Westmoreland Drive, Sarasota
$1,999,000
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

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