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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: 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
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
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
811 Alderwood Way, Sarasota
$399,000
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.

811 Alderwood Way, 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
138 Pearl Avenue, 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
704 69th Avenue W, Bradenton
$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
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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