Location: Sarasota
Keyword(s): Bayshore High
Keyword(s) High School: Bayshore High
Do Not Show Listings
7322 WESTMORELAND DR, SARASOTA, FL 34243
$2,500,000164 Days on yellowkey MLS ID: A4682111
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3756 Built: 1960 Tax: $17,565 (2024)Community: Whitfield Estates Blks 14-23 & 26Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,565
Elementary School: Florine J. Abel Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Electa Arcotte Lee Magnet
Remarks: 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.
Listing is courtesy of: OVERSEAS REALTY, INC (941-366-3661)
Listing Agent: Holly Nikolich (941-345-7941)
7193 W COUNTRY CLUB DR N #237, SARASOTA, FL 34243
$242,500177 Days on yellowkey MLS ID: A4680028
REDUCED by $2,400 (1.0%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 909 Built: 1973 Tax: $842 (2025)Community: Palm-Aire Desoto Lakes Country ClubCondo
Taxes:$842
Elementary School: Kinnan Elementary
Tax Year: 2025
Middle School: Braden River Middle
Remarks: This is a must see property ~ experience 180 degree gorgeous golf course and lake views.....Beautifully updated 2nd-floor condo in the highly sought-after Palm Aire community, a Golf Community, with optional memberships. This light and bright unit features an updated kitchen, beautiful cabinets, granite countertops, newer appliances and a stylish backsplash, added bonus of IMPACT WINDOWS and sliders, newer hot water heater, newer AC unit, and no carpet! Enjoy peaceful mornings overlooking expansive views and stunning sunsets from your vantage point. Ideally located near shopping, dining, and major roadways. A must-see Palm Aire gem!
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
7715 WESTMORELAND DR, SARASOTA, FL 34243
$2,150,00040 Days on yellowkey MLS ID: A4697116
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4782 Built: 1918Monthly Fee: $3 Tax: $12,663 (2024)Community: Whitfield Estates Unit 1Spa: YesSingle Family
Taxes:$12,663
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
7745 WESTMORELAND DR, SARASOTA, FL 34243
$424,9009 Days on yellowkey MLS ID: TB8530490
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1745 Built: 1935 Tax: $4,946 (2025)Community: Whitfield Estates Unit 1Single Family
Taxes:$4,946
Remarks: Virtually Staged. Classic Sarasota character meets a fresh, modern renovation on an oversized .39-acre homesite! This beautifully updated 3-bedroom, 2-bath home offers an open, flexible floor plan designed for both everyday living and entertaining. The welcoming front porch has a relaxing feel, melting the stress away while rocking on the covered porch. Step inside to the open floor plan with plenty of natural lighting. New gorgeous flooring. A spacious kitchen features white shaker-style cabinetry, stone countertops, stainless steel appliances, a large center island and abundant storage. This space is great for entertaining! The living room can accommodate a sectional sofa and more! All bathrooms have been updated with beautiful tile work in the showers. Outside is where this property truly stands apart. The expansive fenced yard provides exceptional room to enjoy the Florida lifestyle, complete with a fire-pit gathering area, patio space and an oversized concrete parking area offering room for an RV, boat, trailer and multiple vehicles—a rare find for buyers who need space for their recreational toys. The location puts you close to some of the best of the Sarasota area. Boaters can take advantage of nearby public water access, including Ken Thompson Boat Ramp and Centennial Park, while outdoor recreation and waterfront scenery await at Bayfront Park. Shopping, dining and entertainment options are abundant at University Town Center and the iconic St. Armands Circle. Sarasota's renowned beaches, downtown cultural attractions and waterfront destinations are also within easy reach. Frequent travelers will appreciate convenient access to Sarasota Bradenton International Airport. With its updated interior, oversized lot, expansive outdoor space and exceptional parking for boats and RVs, this home offers a combination of versatility, location and Florida lifestyle that is increasingly difficult to find. Schedule your private showing today! ROOF 2022, WINDOWS 2022, AC 2020, WATER HEATER 2026, ELECTRIC PANEL 2022
Listing is courtesy of: GUARDIAN REAL ESTATE SERVICES (813-767-2582)
Listing Agent: Michael Hernandez (813-220-5610)
329 BERNARD AVE, SARASOTA, FL 34243
$750,00034 Days on yellowkey MLS ID: A4697412
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2250 Built: 1969Monthly Fee: $3 Tax: $2,055 (2025)Community: Ballentine Manor EstatesSingle Family
Taxes:$2,055
Remarks: West of the Trail and just past University Parkway, this beautifully maintained home in the private Ballentine Manor Estates offers an exceptional Sarasota lifestyle with an unbeatable location just 5 minutes from SRQ International Airport, 10 minutes to UTC Mall, downtown Sarasota, Lido Beach, St. Armands Circle, and Longboat Key, and only 15 minutes to Siesta Key Beach. Just six homes from Sarasota Bay and the Intracoastal Waterway, enjoy easy access to kayaking, stunning sunsets, and waterfront relaxation. This light-filled 4-bedroom, 3-bath residence features an open floor plan with a split-bedroom design, providing privacy for the spacious primary suite. The chef's kitchen boasts granite countertops, stainless steel appliances, and a gas stove, while the Florida room overlooks a screened 15' x 30' pool, shaded deck, and beautifully landscaped, fully fenced backyard except far N end is tropical growth with ample space for family and pets. The private fourth-bedroom suite, complete with its own entrance, living area, and kitchenette, offers excellent guest, in-law, or rental potential. Additional highlights include partial bay views from the front yard, a circular driveway with abundant parking, a large dog run, a new shed installed in 2025, and no flooding or structural damage from past hurricanes. Whether you're seeking a full-time residence, seasonal retreat, or income-producing property, this is a rare opportunity to own a private Sarasota paradise in one of the area's most desirable locations. Improvements and permits are on tax records. A bank appraisal was done in 04/25 and owner shared it was $850,000. Buyers must rely on home inspection and some furniture may be negotiable. no damage or flooding to home from 2024 hurricanes some landscaping debris and a new shed was replaced.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
426 WHITFIELD AVE, SARASOTA, FL 34243
$480,00020 Days on yellowkey MLS ID: A4697567
3 Days Off yellowkey (back on 7/16/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1811 Built: 1973Monthly Fee: $4 Tax: $1,896 (2025)Community: Whitfield EstatesSpa: NoSingle Family
Taxes:$1,896
Elementary School: Bayshore Elementary
Remarks: Nestled in the desirable Sara Bay Country Club community, this Arthur Rutenberg home offers an exceptional opportunity to make it your own. Golf membership is not required, while the voluntary HOA provides access to dining and social events at the clubhouse restaurant and lounge. Ideally located midway between Downtown Sarasota and Downtown Bradenton, and just a short walk to Sarasota Bay. Situated on an oversized 23,335-square-foot L-shaped lot, this property offers plenty of privacy and outdoor space. A large fenced backyard provides a secure area for everyone and pets, while the property extends approximately 340 feet to picturesque Bowlees Creek, creating a peaceful natural backdrop. The interior is ready for your personal updates, but many of the home's major improvements have already been completed, including a new barrel tile roof (May 2023), a new pool screen enclosure (2024), recently resurfaced pool, hurricane-impact windows and sliding glass doors (March 2018), Carrier HVAC system (June 2018), and a Generac whole-house generator (June 2019). With solid construction, an outstanding location, and significant exterior upgrades already in place, this home is ready for its next chapter.
Listing is courtesy of: WAGNER REALTY (941-756-7800)
Listing Agent: Lynda Wagner (941-518-5755)
7125 WESTMORELAND DR, SARASOTA, FL 34243
$3,525,000220 Days on yellowkey MLS ID: A4675672
REDUCED by $70,000 (1.9%) on 07/15/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4343 Built: 2025 Tax: $4,490 (2024)Community: North IslesSingle Family
Taxes:$4,490
Remarks: Virtually Staged. The Abaco Model is a stunning Sarasota luxury residence offering 4,343 square feet of refined living space and 6,273 square feet under roof, featuring four true bedrooms and six total rooms. This home is Florida Green Home Bronze Certified, reflecting thoughtful construction, energy efficiency, and sustainable building practices. Upon arrival through dramatic 10-foot iron front doors, the foyer provides a breathtaking sightline through the home to the pool and canal beyond. The oversized great room is ideal for entertaining and showcases stained cypress beams, a gas fireplace with full-height tile surround, and a 16-foot-wide by 10-foot-high pocketing sliding glass door that opens seamlessly to the outdoor living and pool area. The chef’s kitchen features an oversized island with gas cooktop, walk-in pantry, and sunlit windows above the sink for abundant natural light. The private owner’s wing includes a refined library or office adjacent to the owner’s suite, both enjoying water views. Dual oversized customized built in walk-in closets and a spa-inspired owner’s bath complete the retreat with a freestanding soaking tub, walk-in shower, private water closet, and separate his-and-her vanities. Two additional guest suites accommodate king-sized beds and feature ensuite baths and walk-in closets. A waterfront bonus room at the rear of the home also enjoys water views and is serviced by a nearby full bath that also functions as a powder bath and pool bath. Two additional flexible sleeping rooms bring the total sleeping capacity to six. The expansive outdoor living and dining area overlooks the pool and spa and includes a cozy gas fireplace, creating the perfect waterfront entertaining setting. The three-car garage leads into a walk-in laundry room with a dedicated storage closet. All windows and exterior doors feature Low-E impact glass, all interior doors are 8-foot shaker style, all interior walls include sound batt insulation, walls and ceilings have smooth finishes, and all interior floors are tiled throughout. Cabinetry is by Wood-Mode/Brookhaven. The West Indies–inspired exterior elevation features shutters, corbels, decorative brackets, and a concrete tile roof. The private dock includes a high-capacity 33,000-pound boat lift with water and power and is capable of accommodating 40–50-foot vessels with protected deep-water access and quick entry to Sarasota Bay making this property ideal for the serious boater.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Lauren Holt, Pllc (941-928-7211)
214 GAINES AVE, SARASOTA, FL 34243
$660,000111 Days on yellowkey MLS ID: A4688411
REDUCED by $20,000 (2.9%) on 05/14/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1992 Built: 1955 Tax: $6,877 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$6,877
Remarks: Experience the best of Sarasota living in this beautifully updated single-story ranch home with pool, nestled in sought-after Whitfield Estates—a Manatee County gem with a Sarasota address. Situated near Sarasota Bay, this home sits among multi-million-dollar residences and offers the perfect blend of comfort, charm, and opportunity. This 3-bedroom, 3-bath home welcomes you with bright, open living spaces filled with natural light. The primary bedroom and 2nd bedroom both feature walk-in closets and ensuite baths. The open-concept floorplan connects the living, dining, and kitchen areas—ideal for entertaining or relaxing by the cozy fireplace. A stylish kitchen bar provides extra seating and a central gathering spot. Step outside to your private Florida oasis: a heated pool with screened enclosure, surrounded by lush landscaping on a spacious 1/3-acre lot. Enjoy morning coffee on the front patio with peek-a-boo views of Sarasota Bay, or take an evening stroll to the bay and watch the sunset. Whether you’re searching for a full-time residence, seasonal retreat, or short-term rental investment, this property offers endless possibilities in one of Sarasota’s most desirable neighborhoods. This property is built of concrete block construction, has impact windows, and sits in the desirable X flood zone (flood insurance is not required). Roof is membrane material (2017). AC (2023). For an optional annual HOA fee of just $35, homeowners in Whitfield Estates may obtain a culinary membership at Sara Bay Country Club, granting full access to the clubhouse for dining and social events (golf privileges not included; membership subject to club approval). You and your guests will have plenty of entertainment and convenience options within a short drive including Sarasota Bay, IMG Academy, SRQ Airport, University Towne Center Mall, downtown Sarasota, St. Armands Circle, Lido Key and gulf beaches.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
7524 WESTMORELAND DR, SARASOTA, FL 34243
$5,500,00046 Days on yellowkey MLS ID: A4695898
Bed: 6 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 6215 Built: 2001 Tax: $15,233 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$15,233
Remarks: 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.
Listing is courtesy of: FLORIDA INTERNET REALTY LLC (941-961-4983)
Listing Agent: Steve Rider (941-504-5163)
361 SCOTT AVE, SARASOTA, FL 34243
$599,00076 Days on yellowkey MLS ID: A4692752
0 Days Off yellowkey (back on 7/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 1961Monthly Fee: $3 Tax: $6,662 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$6,662
Remarks: Under contract-accepting backup offers. Welcome to 361 Scott Avenue, a beautifully refreshed pool home in the heart of Whitfield Estates, west of the Tamiami Trail. Set on a rare double lot just minutes from Sarasota Bay, the property offers the kind of laid-back Florida living that's getting harder to find at this price. You'll step into a bright, open great room that flows right into the kitchen, where Corian counters, a center island, built-in oven, and separate cooktop make hosting easy. Original terrazzo and ceramic tile run through much of the home, paired with crown molding, textured ceilings, and fresh interior paint that warms up the mid-century bones. The primary suite has been reworked as a true retreat, with a custom-fitted walk-in closet and a fully updated granite bath. Two more bedrooms, a separate laundry, and a tucked-away dining room round out a layout that lives easy on one level. Hurricane impact windows fill the home with light while keeping things quiet inside. Out back is where this house really shines. A covered lanai opens to an 18x36 private pool, all wrapped by a fully fenced and irrigated yard with plenty of room to entertain or expand. The double lot offers privacy and flexibility you almost never see this close to the Bay. Concrete block build, recent improvements include roof (2017), HVAC (2017), and variable-speed pool pump (2017). Flood Zone X means flood insurance isn't currently required. The OPTIONAL Whitfield Estates HOA runs just $35 a year, and residents can apply for culinary membership at the historic Sara Bay Country Club. You're a quick drive to The Ringling, Asolo Repertory Theatre, New College, Ringling College of Art and Design, IMG Academy, SRQ International Airport, UTC, and downtown Sarasota. St. Armands Circle, Lido Key, and the Gulf beaches are all close at hand. A rare chance to own a true classic in one of Sarasota's most established west-of-Trail neighborhoods
Listing Agent: Jessica Dunnam (941-713-1339)
7280 ELEANOR CIR #101, SARASOTA, FL 34243
$231,000110 Days on yellowkey MLS ID: A4688357
REDUCED by $4,000 (1.7%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1064 Built: 1993 Tax: $1,570 (2025)Community: Pinehurst Sec ISpa: NoCondo
Taxes:$1,570
Remarks: Welcome to Pinehurst at Palm Aire, This immaculate ground floor end unit that shows like a model! You'll enjoy the open light and bright feeling of this Split Plan bedrooms. Large windows and sliding glass doors make this a light, bright, airy space. Enjoy the privacy of the lush preserve behind the unit while sitting on your screened in lanai, accessible from both the living room and master bedroom. The UPDATED KITCHEN offers ample cabinets and counter space featuring newer granite counter tops and a breakfast bar that opens to the great room. The OPEN CONCEPT features tile flooring throughout the unit in the great room, dining room, kitchen, bedrooms, bathrooms and laundry room. UPDATED BATHROOMS with new countertops, In addition the unit features newer ceiling fans and A/C 2017, ROOF replacement 2016 by the condominium association. The Master suite features a large walk-in closet and private master bath with walk-in shower. A large second bedroom accommodates guests well with close proximity to the second full bath featuring a newer vanity with stone counter top and full sized tub. The separate laundry room includes washer/dryer, storage area, and water heater, has tile flooring and is brightened by a window. Your one car GARAGE houses your vehicle and plenty of storage. With only a short walking distance to the community pool, tennis and great walking areas. this Pinehurst condo is also ideally located with a short drive to SRQ International Airport, RSW,PGD, TPA airports an hour away. Some of the best shopping and restaurants are just minutes away. The UTC Mall. Convenient to all the area has, downtown Sarasota or Lakewood Ranch, the Gulf beaches 20-25 mins and easy access to the interstate. You can join nearby Palm Aire Country Club, a full-service country club featuring 36 hole year-round golf, dining, tennis, pickleball, water aerobics, and various social activities and events.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
7318 WESTMORELAND DR, SARASOTA, FL 34243
$2,000,000177 Days on yellowkey MLS ID: A4680287
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4224 Built: 1958Monthly Fee: $3 Tax: $5,885 (2025)Community: North IslesSpa: NoSingle Family
Taxes:$5,885
Remarks: WOW..the view! This exceptional waterfront property is offered for only the second time since 1958. Ideally positioned directly on Sarasota Bay, it features sweeping bay views. Experience the magical sunsets, then the twinkling lights of Longboat Key at night. Nature lovers can enjoy the variety of birds, manatees, and frolicking dolphins. Each day is a new show of natural beauty, and the sunsets never get old. The estate-sized 0.80-acre lot offers approximately 103 feet of direct bay frontage, providing an extraordinary setting for a custom coastal retreat, and a coveted Sarasota address within Manatee County. The existing home sustained hurricane damage, presenting a rare opportunity for a new owner to reimagine or rebuild and create their dream waterfront estate. Located on boating water with access to the Intracoastal Waterway and the Gulf of Mexico, this property is perfectly suited for boating and fishing enthusiasts. An expansive raised edge pool with paver deck, fenced yard, private well irrigation and propane gas add practical value to this unique offering. The Whitfield Estates community has a rich history and is an eclectic mix of homes from 1920’s Mediterranean architecture to modern designs. Voluntary neighborhood association membership is just $30 annually and includes access to nearby Sara Bay Country Club for culinary membership. Centrally located just minutes from downtown Sarasota’s cultural attractions, dining, shopping, IMG Academy, renowned Gulf beaches, and SRQ International Airport—only five minutes away. Waterfront opportunities of this caliber are increasingly rare. Embrace the potential, the location, and the timeless appeal of Sarasota Bay living, and make this extraordinary property your own.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Cheryl Roberts (941-266-1450)
7746 WESTMORELAND DR, SARASOTA, FL 34243
$535,000116 Days on yellowkey MLS ID: A4688339
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1345 Built: 1959 Tax: $4,629 (2025)Community: Whitfield EstatesSingle Family
Taxes:$4,629
Remarks: 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!
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Jessie Bonner (941-356-3182)
7150 N TAMIAMI TRL #S503, SARASOTA, FL 34243
$95,00041 Days on yellowkey MLS ID: A4696866
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 348 Built: 1959Monthly Fee: $760 Tax: $1,191 (2025)Community: Sarasota Cay Club CondoCondo
Taxes:$1,191
Remarks: Great location for an investment or vacation in Sunny Florida. Onsite tiki bar and heated pool. Less than 2 miles from Sarasota Bradenton National Airport. Short drive across the beautiful Ringling Bridge to St Armands Circle and Lido Beach.
Listing is courtesy of: CONCORDIA REALTY LLC (941-404-5392)
Listing Agent: Bruce Thompson (850-573-2063)
8152 LONGBAY BLVD, SARASOTA, FL 34243
$3,250,00058 Days on yellowkey MLS ID: A4695175
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4383 Built: 2001Community: Benatovich-DitomasoSpa: NoSingle Family
Taxes:$0
Remarks: Discover timeless European elegance and exceptional gated waterfront living at this meticulously remodeled bay-front residence. This 4-bedroom, 3.5-bath home offers 4,383 square feet of refined living space on a spacious 37,800-square-foot lot with 100 feet of direct Sarasota Bay frontage. Enjoy breathtaking water views in a private, natural setting protected by mangroves, mature landscaping, and specimen plantings. The property sustained no flood damage during the 2024 storm season. Built in 2001 and fully transformed in 2016, the home features exceptional craftsmanship, handsome millwork, and thoughtful custom updates throughout. Soaring ceilings, an impressive entryway, engineered scraped maple and porcelain tile flooring, and abundant natural light create an open, inviting atmosphere ideal for both grand entertaining and relaxed everyday living. On the main floor, the home features a spacious living room with electric fireplace, a separate dining room which could double as an office, the kitchen and breakfast area, and a well-designed laundry room, plus 2 generous bedrooms that connect to a den/sitting area and a wet bar. The gourmet kitchen is a chef’s masterpiece, boasting quartz countertops, two islands, a pot filler, a large walk-in pantry, and premium appliances including a Sub-Zero refrigerator, Bosch dishwasher and gas range with custom hood, Samsung Duo-zone oven, microwave, and under-counter wine/beverage cooler. It also features solid wood custom cabinetry and a beautiful farmhouse double sink. A generous laundry room offers LG front-loading washer and dryer, solid wood cabinetry, a custom drying rack, and a built-in ironing board. The upstairs primary suite is a true retreat, complete with its own entry gallery and a private sitting room featuring a cathedral ceiling. Step out onto the large private balcony overlooking the pool, lush gardens, and sailboats on Sarasota Bay. The luxurious primary bath includes a large shower, double vanity, a separate built-in dressing table, and a spacious 13’ x 16’ his-and-her's walk-in closet with custom organization and display features. The versatile fourth bedroom functions as a garage apartment, offering a main-floor living room and kitchenette, plus a large second-floor bedroom and bath with its own private balcony—perfect for guests, a caregiver, or extended family. Outside, resort-style living awaits on the expansive covered patio overlooking a 45’ x 15’ private pool, beautiful landscaping, and panoramic Sarasota Bay views. Additional highlights include a full irrigation system with well, a 2018 standing seam metal roof, tankless water heater, updated HVAC systems, and a well-positioned outdoor kitchen with a Blaze grill. Perfectly located just three miles north of downtown Sarasota, this exceptional bay-front home is minutes from the Ringling Museum, Ringling College of Art and Design, SRQ International Airport, fine dining, cultural venues, St. Armands Circle, and the pristine Gulf Coast beaches.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Julie Klick (941-780-6001)
139 ADAIR AVE, SARASOTA, FL 34243
$500,000419 Days on yellowkey MLS ID: A4654370
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2038 Built: 1973 Tax: $6,722 (2024)Community: Whitfield Estates Blks 14-23 & 26Single Family
Taxes:$6,722
Remarks: 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.
138 PEARL AVE, SARASOTA, FL 34243
$570,00087 Days on yellowkey MLS ID: A4691706
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1371 Built: 1954 Tax: $5,242 (2024)Community: Whitfield Estates Blks 14-23 & 26Single Family
Taxes:$5,242
Remarks: 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.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jeremy Egglefield (941-809-9200)
121 HOLLY AVE, SARASOTA, FL 34243
$1,295,000128 Days on yellowkey MLS ID: A4686397
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1883 Built: 1970 Tax: $12,872 (2025)Community: North IslesSpa: YesSingle Family
Taxes:$12,872
Remarks: On a large waterfront homesite in the North Isles neighborhood of Whitfield Estates, this property offers the kind of Florida lifestyle buyers actively seek with sailboat water basin, boat dock, two remote-control boat lifts, quick access to Sarasota Bay, a screened heated pool and spa, and room to enjoy it all on nearly half an acre. The .43-acre lot is beautifully landscaped and features a screened food garden, irrigation well, brick paver walkways and a solar PV system. Inside, the residence was solidly upgraded in 2023 and well-finished with travertine tile flooring through the main living areas and baths, luxury vinyl plank in the bedrooms, crown molding and wood shutters throughout. The layout includes three bedrooms, three baths and a flexible bonus room. Wood cabinetry with soft-close doors and drawers, along with abundant storage, adds everyday function to the home’s inviting interior. Notable features include hurricane-impact windows and doors, heated pool and spa, lightning protection, central vacuum and outdoor lights. For buyers seeking more than personal enjoyment, the property also offers a proven rental history, making it a compelling potential income investment as well as a waterfront retreat. North Isles is part of the historic Whitfield area, prized for its Old Florida character, spacious homesites and proximity to Sarasota Bay. The location is especially convenient. Just west of U.S. 41, near the airport, close to Sara Bay Golf and Country Club, and well positioned for an easy drive north into Bradenton or south to Sarasota.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Andrew Tanner (941-539-0998)
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