Whitfield Estates Homes under $500,000

Whitfield Estates Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Whitfield Estates and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest Whitfield Estates Homes under $500,000

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
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
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
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
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
Start Your Search

How much is your home worth?

Get instant property value now!