Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
2417 PARSON LN, SARASOTA, FL 34239
$395,000129 Days on yellowkey MLS ID: A4675748
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1957Monthly Fee: $17 Tax: $5,426 (2025)Community: South GateSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,426
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Don’t miss this adorable SOUTHSIDE ELEMENTARY-zoned gem in hip South Gate! The location could not be more convenient – walk to the Crossings at Siesta Key Mall and less than a mile to the north bridge to Siesta Key itself! For those with school-age children, the close proximity to Brookside Middle School and Southside Elementary zoning are great perks. Completely updated inside with an elegant kitchen (granite, pretty backsplash, stainless appliances), chic wood-look flooring throughout, a charming fireplace, and recently renovated baths, it is move-in ready! Ideally positioned for ultimate convenience to the many amenities of Sarasota, with wonderful possibilities from a full-time or seasonal abode to a prime investment opportunity. The space inside is used really well, with nice spacious bedrooms and a split-bedroom plan, and outside you’ll enjoy a covered screened patio and HUGE fully fenced backyard! There is currently a fun fire pit and open land, so the large yard can be a blank canvas for your outdoor Florida dreams. There is plenty of space for a pool, if that is your desire, or maybe you prefer to plant an edible garden? The choice is yours and this lot can accommodate it all! An oversized 1-car garage with separated extra storage space and laundry completes the package. Easy to show, schedule your visit today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Allison Werner (941-961-3212)
1703 STARLING DR #1703, SARASOTA, FL 34231
$749,000192 Days on yellowkey MLS ID: A4668895
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2172 Built: 1993 Tax: $4,481 (2024)Community: Villas At Eagles PointCondo
Taxes:$4,481
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Remarks: Welcome to carefree living in The Landings. This beautifully remodeled townhome makes carefree living an absolute dream! Not an inch has gone untouched, showcasing modern luxury finishes. Whether you're looking to winter in Sarasota or enjoy all that The Landings Racquet Club has to offer all year long, you are sure to relish coming home. The first-floor primary bedroom is very spacious, with an equally comfortable en suite and custom walk-in closet. The large back lanai features perfect privacy. There is a loft or family room upstairs, just outside the additional two bedrooms; perfect for an office, playroom, or sitting area. The neighborhood offers a 24-hr manned security gate, a world-class tennis and pickleball facility, pool, fitness center, and clubhouse. You'll never need to leave! But when you choose to venture out, popular restaurants and shopping are just outside the gates!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Tracy Leclair (941-209-0549)
1622 29TH ST, SARASOTA, FL 34234
$199,990170 Days on yellowkey MLS ID: A4663461
0 Days Off yellowkey (back on 4/23/2026)
REDUCED by $29,910 (13.0%) on 04/16/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1146 Built: 1960 Tax: $2,645 (2024)Community: Newtown Heights First Add ToSingle Family
Taxes:$2,645
Elementary School: Brentwood Elementary
High School: Booker High
Remarks: Under contract-accepting backup offers. Price Improvement! New price, $199,990—this is your opportunity to own an affordable single-family home, 3-bedroom, 1-bath in The Newtown neighborhood of Sarasota. Whether you’re a first-time buyer, investor, or looking for a seasonal home, this is an incredible value in THE CITY OF SARASOTA! NO HOA! Affordable living and convenience. Move-in ready. Freshly painted inside and out, this home offers easy-care ceramic tile and vinyl plank flooring throughout—perfect for low-maintenance living. Enjoy peace of mind with a new A/C (2024) and a beautifully updated kitchen featuring granite countertops, under-cabinet lighting, and brand-new appliances (2025) including refrigerator with ice maker, range, microwave, and dishwasher. Step outside to a fully fenced backyard—ideal for gardening, grilling and pets. Location is everything! Just minutes from: Booker High School (Visual & Performing Arts program), Ringling College of Art and Design, The Bay Park, Sarasota Bradenton International Airport, UTC Mall, Siesta Beach and Lido Beach, Robert L. Taylor Community Complex and Payne Park. This home is perfectly positioned near the local bus stop, major roadways including US-301, offering quick access to downtown and surrounding areas. Ideal for first-time buyers, investors, or those looking to downsize. With strong rental potential and NO HOA restrictions, this property is a smart buy in a growing area. Priced to sell.. Schedule your showing today.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Gloria Waters (941-356-9386)
3751 S SCHOOL AVE #11, SARASOTA, FL 34239
$145,00063 Days on yellowkey MLS ID: A4683405
1 Days Off yellowkey (back on 4/23/2026)
REDUCED by $4,900 (3.3%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,774 (2025)Community: Sunland AptsCondo
Taxes:$1,774
Remarks: Under contract-accepting backup offers. Stunning and move-in ready, this beautifully renovated and fully furnished 2-bedroom, 2-bath condo offers effortless living in an exceptionally convenient central Sarasota location. Perfectly positioned in the heart of the city, you are just minutes from Downtown Sarasota, Sarasota Memorial Hospital, and a straight drive to Siesta Key’s world-famous beaches. Enjoy the rare combination of accessibility and everyday walkability, with popular dining, cafés, and entertainment only a short stroll away. Inside, the condo has been updated to the nines, showcasing a bright, naturally light interior and a complete 2023 renovation including a modern kitchen with quartz countertops and breakfast bar, fully renovated bathrooms, updated flooring throughout, impact (hurricane-rated) windows, and custom window treatments. Offered fully furnished and move-in ready, this residence is ideal for seasonal living, downsizing, or anyone seeking a low-maintenance Sarasota retreat. Ground-floor convenience, a quiet private setting, parking directly outside the unit, and the added benefit of not being located in a flood zone further enhance the appeal. The community pool and laundry facilities are just steps away, adding to the ease of everyday living. Located within a desirable 55+ community, this condo delivers comfort, simplicity, and exceptional lifestyle appeal. Spend your time enjoying Sarasota’s favorite attractions while living in the heart of the city — mornings on Siesta Key’s world-renowned beaches, afternoons exploring local markets and boutiques, and evenings spent dining at the area’s exceptional restaurants. The property can be rented after 1 year of ownership with 4 month lease minimums - no pets allowed. Schedule your tour today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ryan Adamson, Pa (941-713-9234)
546A BEACH RD #A544, SARASOTA, FL 34242
$1,980,000287 Days on yellowkey MLS ID: A4657651
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2611 Built: 1981 Tax: $20,998 (2024)Community: Tiffany SandsTownhouse
Taxes:$20,998
Remarks: Under contract-accepting backup offers. Gulf-front luxury townhome with private beach access on Siesta Key! Soak in the breathtaking, unobstructed views of the Gulf and iconic Siesta Beach from every level of this three-story, turnkey-furnished townhouse-style condominium. Just a short distance from the sand in the intimate, nine-residence enclave of Tiffany Sands, this rare Siesta Key offers blends relaxed beachside living with elegant design and modern comforts. Spanning 2,611 square feet, this three-bedroom, 3.5-bath residence welcomes you with an open-concept main floor that seamlessly connects the kitchen, dining and living areas—all framed by floor-to-ceiling impact-rated sliding glass doors and panoramic Gulf vistas. The living room is anchored by a cozy wood-burning fireplace and enhanced by crown molding, recessed lighting and sleek ceramic tile flooring. Go onto the expansive Gulf-front balcony, an ideal setting for alfresco dining or sunset lounging. The kitchen is stylish and functional, featuring solid-surface countertops, stainless steel appliances, modern cabinetry with pullout shelving, under-cabinet lighting and a breakfast bar for casual meals. Upstairs, the spacious Gulf-front primary suite offers postcard-worthy views, a private balcony, sitting area, double closets and a luxurious en-suite bath with jetted soaking tub, double vanity, separate shower, bidet and two skylights. Two additional guest bedrooms—flexibly configured with a retractable dividing wall—are also on the third floor along with a full guest bath and a well-equipped laundry room. The oversized ground-floor bonus room opens via sliding glass doors to a covered patio just steps from your private beach path. A full bath with walk-in shower was stylishly updated in 2024, making this level ideal for guests, a home gym or media lounge. Additional highlights include a one-car attached garage with extra storage, newer water heater (2024), HVAC (2022), roof and skylights (2017), hurricane shutters and flexibility of 30-day minimum rentals. Just .4 miles from Siesta Village’s vibrant shops and dining, and Siesta Beach Park, this exceptional home delivers the ultimate island lifestyle—whether you’re seeking a serene personal retreat, a seasonal escape or a savvy investment property.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
3410 S SCHOOL AVE, SARASOTA, FL 34239
$699,999164 Days on yellowkey MLS ID: A4671779
REDUCED by $49,001 (6.5%) on 04/21/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3229 Built: 1956Monthly Fee: $17 Tax: $5,754 (2024)Community: South GateSpa: NoSingle Family
Taxes:$5,754
Remarks: Under contract-accepting backup offers. Spacious and thoughtfully designed, this 4-bedroom, 4-bath home in South Gate offers a rare combination of size, layout, and value. Major components have already been addressed with copper wiring and PVC plumbing, providing added peace of mind. Vaulted ceilings, built-ins, and new skylights enhance the light-filled interior. The well-proportioned floor plan includes three en-suite bedrooms plus a private 600 sq. ft. upstairs suite with sitting area, kitchenette, and electric fireplace—ideal for guests, in-laws, or teens seeking separation and space. The primary suite offers a jetted soaking tub with shower, separate water closet, multiple closets, and a foyer area well suited for a desk or reading nook. The main living area flows seamlessly to the kitchen and dining spaces, while the fenced backyard offers room to play, garden, or create an ideal outdoor retreat with space to add a pool. Located within Sarasota’s highly rated school district and just minutes to Siesta Key Beach, downtown, and shopping, this home delivers comfort, functionality, and location in one compelling opportunity.
Listing Agent: Sherri Mills (941-350-7112)
3339 SHEFFIELD CIR, SARASOTA, FL 34239
$490,00045 Days on yellowkey MLS ID: TB8486256
REDUCED by $10,000 (2.0%) on 04/23/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2360 Built: 1993Monthly Fee: $8 Tax: $4,911 (2025)Community: Village Green Club EstatesSingle Family
Taxes:$4,911
Elementary School: Wilkinson Elementary
Remarks: If you have been searching for a property in Sarasota that pairs an unbeatable golf course location with the peace of mind that comes from a fully updated home, this is it. Tucked away in the desirable Village Green Estates, this 3-bedroom, 4-bathroom residence is positioned on a premier lot that offers sweeping, private panoramic views of the greens. Unlike many homes in the area, the major heavy lifting has already been completed, including new hurricane impact windows (2025), a fresh HVAC system (2024), updated plumbing (2019), and a tile roof (2018). The layout is designed for the Florida lifestyle, featuring a rear screened patio. Inside, triple pocket sliding doors disappear to merge the interior living space with the scenic outdoor backdrop. A standout feature of this floor plan is the versatile "suite-within-a-suite"—a large bonus room attached to the primary bedroom with its own full bath and private exterior entrance. Whether you need a dedicated home office, a nursery, or a guest wing, this space adapts to your needs. The location offers a rare combination of convenience and low-cost living with NO CDD fees and a remarkably low $100 annual HOA fee. You are just minutes away from the Legacy Bike Trail, UTC Mall, Downtown Sarasota, and the white sands of Siesta Key, with daily essentials like Publix and Starbucks right around the corner. This is a rare opportunity to secure a high-quality, move-in-ready home on the golf course without the high carrying costs of a typical country club.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Ana Mitchell (813-599-4669)
521 CUMMINGS ST, SARASOTA, FL 34242
$1,450,000199 Days on yellowkey MLS ID: A4667165
REDUCED by $45,000 (3.0%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2500 Built: 1983 Tax: $7,154 (2025)Community: Ocean Beach RepSingle Family
Taxes:$7,154
Remarks: One or more photo(s) has been virtually staged. Siesta Key Waterfront Retreat – Walk to the Beach & Village! Ready for immediate enjoyment this winter, this 3-bedroom, 2-bath Key West–inspired home embodies the essence of the Siesta Key lifestyle—boating from your backyard and strolling to the powdery white sands and vibrant Siesta Key Village with its renowned dining, boutiques, and nightlife. Nestled on a quiet cul-de-sac, this canal-front retreat offers 100 feet of waterfront, a covered 5,000-lb boat lift, and direct access to the Intracoastal Waterway. The expansive outdoor living area invites relaxation and entertaining with a heated pool featuring a cascading stone waterfall, covered bar & and wide open fenced area surrounded by tropical landscape creating a private island ambiance. Inside, a neutral palate, high ceilings, and open layout feels light and airy. The white kitchen features granite countertops, stainless steel appliances, dual sinks, a center cooking island, and a breakfast bar perfect for casual dining. Warmth and character is further enhanced by a marble fireplace in the main living and dining areas. The primary suite offers a peaceful retreat with an ensuite bath, dual vanities, a walk-in shower, and a charming window seat. Guests & children have their own wing with a full bath and a convenient laundry room. Enjoy peace of mind with impact windows, hurricane-rated doors, and major upgrades including a metal roof, Trex decking, Nichiha siding, and reinforced lanai. Positioned at one of the highest elevations on the street, the home has never experienced flooding. And there’s an additional ground floor BONUS…a generously sized sunlit air-conditioned play & storage room! Whether you’re searching for a seasonal escape, a full-time residence, or a property with strong vacation rental appeal, this move-in-ready home offers exceptional versatility and potential.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3360 S OSPREY AVE #201B, SARASOTA, FL 34239
$249,000167 Days on yellowkey MLS ID: A4671792
3 Days Off yellowkey (back on 4/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1969 Tax: $3,282 (2025)Community: Bermuda On OspreyCondo
Taxes:$3,282
Remarks: Under contract-accepting backup offers. One step away from Siesta Key, Sarasota Memorial and Hillview. West of the trail. Beautiful condo in Oasis on Osprey. Enjoy the community pool before you head to the beach.2 bedrooms, 2 bathrooms. large living area. Screened lanai. All tiled for easy maintenance. Granite countertop in kitchen. AC 2020.
Listing is courtesy of: INVESTUS REALTY LLC (941-538-2010)
Listing Agent: Vincent Ricaud (941-538-2010)
1429 N LAKE SHORE DR, SARASOTA, FL 34231
$5,595,000136 Days on yellowkey MLS ID: A4674740
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4545 Built: 2026 Tax: $9,862 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$9,862
Remarks: One or more photo(s) has been virtually staged. Experience luxury West-of-Trail living in Sarasota’s coveted Oyster Bay neighborhood. This newly built 2026 custom residence offers 5 bedrooms, 5 full and 2 half baths—all on one thoughtfully designed living level—featuring 4,545 sq. ft. under air and 5,689 sq. ft. total. Set on an impressive 130' x 150' corner lot (0.45 acres), the home is surrounded by a lush tropical oasis that provides exceptional privacy. A dramatic two-story foyer with 21’ ceilings and a steel-and-impact-glass entry door welcomes you inside. Engineered oak hardwood flooring, 10” baseboards, and sleek horizontal receptacles enhance the home’s modern architectural aesthetic. The expansive open-concept kitchen and great room are flooded with natural light from ten windows and four 20’ hurricane-impact glass sliders that open to the outdoor living space. The gourmet kitchen is a chef’s dream, offering an 8-seat center island, large walk-in pantry, quartz countertops, and premium appliances including a Bosch 36” natural gas/induction cooktop, 36” Thermador refrigerator column, 24” Thermador freezer column, 24” full-height Thermador wine cooler, Bosch dishwasher, and 30” Bosch oven/microwave combo. Retreat to the luxurious main suite featuring a Wetstyle tub with wood surround, marble accents, and slate and porcelain flooring. Additional highlights include level-5 smooth interior walls, 8’ solid-core and obscure-glass interior doors, a stunning 175-bottle wine room with marble wall and glass enclosure, Samsung pedestal washer & dryer, and an advanced alarm and exterior security lighting system. The outdoor living area is designed for year-round enjoyment with a summer kitchen equipped with a Blaze 42” gas grill, sink, and under-counter refrigerator. A 15’ x 28’ pool and spa with a custom waterfall feature, plus an outdoor shower, complete this private retreat. The property also offers an irrigation system and a spacious 3-car garage. An exceptional opportunity to own a brand-new, luxury single-level home in one of Sarasota’s most desirable West-of-Trail communities.
1421 N LAKE SHORE DR, SARASOTA, FL 34231
$4,695,000136 Days on yellowkey MLS ID: A4674749
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 4217 Built: 2021 Tax: $31,036 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$31,036
Remarks: Perfectly positioned on a spacious, private lot in the prestigious and highly sought-after Oyster Bay Estates community, the residence embodies exceptional design, architectural intention, and refined livability. Custom designed and built by distinguished, award-winning Platinum Coast Construction and completed in 2021, this 4-bedroom / 4 full & 2 half bath modern masterpiece was crafted with uncompromising detail and a focus on seamless indoor–outdoor living. Inside, a host of elevated finishes creates a sophisticated yet welcoming atmosphere. Level 5 flat-smooth walls, engineered oak hardwood flooring, 8' solid-core and obscure glass interior doors, 10" baseboards, floating vanities in all baths, and Quartz surfaces throughout promote a clean, modern aesthetic. A dramatic 72" glass fireplace anchors the living area, while the gourmet kitchen boasts high-performance appliances including a Thermador push-to-open column refrigerator, column freezer, 24" wine preserver, Bosch dishwasher, Bosch combo oven/microwave, and 36” induction cooktop. The striking 175-bottle wine room with stone wall adds a stunning design focal point for entertainers and collectors alike. The primary suite offers a spa-like retreat with marble finishes, a Wetstyle soaking tub, and an enclosed outdoor garden area with tropical landscaping, wood decking, and a private outdoor shower. Guest suites each feature en-suite baths and access to a serene outdoor spa-like space with lush plantings, decking, and an outdoor tub and shower—creating peaceful, private escapes separate from the main living areas. Designed for true resort-style living, the exterior features a spectacular 18' x 30' pool and spa with a custom waterfall wall, surrounded by tropical landscaping. The fully equipped outdoor kitchen includes a 42” Blaze gas grill, under-counter refrigerator, outdoor sink, and storage drawers. Additional features include hurricane-impact windows, an advanced security system, irrigation system, and a distinctive 4-car garage with wood-look paneling and a stunning mahogany double-door entry with obscure glass. Situated just moments from Siesta Key, downtown Sarasota, and within walking distance of the prestigious Field Club, Oyster Bay Estates is celebrated for its beautiful streetscapes, active social atmosphere, and proximity to the water and premier amenities. This exceptional residence offers luxurious contemporary living in one of Sarasota’s most desirable neighborhoods.
3191 LAKE PARK LN #2, SARASOTA, FL 34231
$389,00097 Days on yellowkey MLS ID: A4678896
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1738 Built: 1987 Tax: $1,047 (2025)Community: Park Place VillasSpa: NoVilla
Taxes:$1,047
Remarks: Discover comfort, style, and Florida living at its best in this beautifully maintained 2-bedroom, 2-bath villa perfectly situated in central Sarasota - just minutes from the area's pristine beaches, vibrant downtown shopping, and fine dining options. Step inside to a light and bright interior featuring soaring vaulted ceilings, skylights, and an inviting open layout that enhances the spacious feel. A new tile roof (2023) and new A/C system (2025) provide peace of mind and year-round comfort. The living area opens to a relaxing lanai with impact-resistant sliders where you can unwind while taking in the serene lake view and lush, mature landscaping. Two charming bay windows also offer picturesque water views, filling the home with natural light. The primary suite offers a tranquil retreat with stylish LVP flooring, a custom closet system, and an ensuite bathroom with multiple grab bars and zero entry shower. Whether you're seeking a seasonal getaway or a year-round residence, this lakefront villa offers the perfect blend of convenience, beauty, and low-maintenance living - all in one of Sarasota's most desirable locations.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Nancy Moore (941-313-5159)
5770 MIDNIGHT PASS RD #C601, SARASOTA, FL 34242
$1,395,000145 Days on yellowkey MLS ID: A4674063
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1337 Built: 1980 Tax: $11,117 (2024)Community: Gulf & Bay ClubSpa: YesCondo
Taxes:$11,117
Remarks: An exquisite, fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high end detailed finishes and interiors professionally crafted to perfection. This unit is in C Building with direct beach access just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and on site car wash. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Sylvia Wilk (630-863-1825)
2233 MICHELE DR, SARASOTA, FL 34231
$649,900143 Days on yellowkey MLS ID: TB8453606
Bed: 4 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 1970 Tax: $6,847 (2024)Community: Phillipe GardensSpa: NoApartment
Taxes:$6,847
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Fully remodeled Sarasota duplex for sale in highly desirable Phillippi Gardens—NO HOA and NO CDD fees—offering exceptional income potential and investment opportunity just minutes from world-famous Siesta Key Beach, consistently ranked among America's top white-sand beaches. This turnkey multifamily investment property features two spacious 2-bedroom, 1.5-bathroom units, each with an attached 1-car garage, private patio, screened lanai, and fully fenced backyard, delivering ideal privacy and separation for long-term tenants, short-term rental guests, or multigenerational family living. Both units have been thoughtfully and completely upgraded with brand-new luxury vinyl flooring, beautifully renovated kitchens featuring modern cabinetry and countertops, updated bathrooms, new stainless steel appliances including in-unit washers and dryers, all-new hurricane-impact windows and impact-rated garage doors, plus updated plumbing and electrical systems for true peace of mind. In a significant advantage for this market, the property experienced no interior flooding during the 2024 storms—a rare and valuable feature for Gulf Coast buyers. This Sarasota income-producing duplex is perfect for investors seeking strong long-term rental income, mid-term rental opportunities (buyer to verify local regulations), or a smart house-hacking strategy by living in one unit while renting the other to offset the mortgage. Ideally situated approximately 10 minutes from Siesta Key Beach, 12 minutes to Siesta Key Village, under 20 minutes to University Town Center (UTC), and conveniently close to US-41, Downtown Sarasota, waterfront dining, marinas, nightlife, championship golf, and premier shopping, this fully upgraded Phillippi Gardens duplex presents a rare opportunity to own a high-demand Sarasota multifamily investment property in one of the Gulf Coast's strongest rental markets, known for both consistent cash flow and long-term appreciation. Whether you're a seasoned investor expanding your portfolio, a first-time house-hacker, or a buyer seeking a flexible multigenerational property near the beach, this move-in-ready Sarasota duplex delivers location, upgrades, and income potential in one rare package—schedule your private showing today and secure your piece of the Siesta Key Gulf Coast lifestyle.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Mark Middleton (727-871-7653)
8897 MIDNIGHT PASS RD #105, SARASOTA, FL 34242
$515,00076 Days on yellowkey MLS ID: A4681513
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1233 Built: 1973 Tax: $5,776 (2025)Community: Sunrise Cove Sec 1Condo
Taxes:$5,776
Remarks: Luxury waterfront living on Little Sarasota Bay in the highly sought-after Sunrise Cove, located on the peaceful southern end of Siesta Key. This direct bayfront, ground-floor condo offers 2 bedrooms, 2 bathrooms, in-unit laundry, and 1,233 square feet of thoughtfully designed living space with pool and expansive water views. Residents enjoy resort-style amenities including two heated pools, boat docks, tennis and pickleball courts, kayak and bike storage, and a community center featuring a fitness facility, billiards, and ping pong. Conveniently located just minutes from Turtle Beach, local dining, and the trolley stop for easy access to Siesta Beach and Siesta Village—providing the ultimate island lifestyle with boating, shopping, and dining nearby. (No flooding from the 2024 storms.)
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
2421 PROSPECT ST, SARASOTA, FL 34239
$645,90098 Days on yellowkey MLS ID: A4677367
REDUCED by $1,600 (0.2%) on 04/23/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 972 Built: 1956 Tax: $4,592 (2025)Community: Arlington ParkSingle Family
Taxes:$4,592
Elementary School: Alta Vista Elementary
Remarks: Now Offered at a Rare Value...Welcome to 2421 Prospect Street in Arlington Park’s Tightly Held RUSTIC LODGE…This Elegantly Refined Florida Mid-Century Retreat with Modern Coastal Finishes is Rooted in Sarasota’s Golden Era…the 1950s Marked a Time When Homes Were Designed & Built with Longevity & Craftsmanship—2421 is a Beautiful Reflection of That Legacy…Approached Not as a Renovation but as a Custom Crafted Rebuild...A Design-Conscious Builder Honored the Original Vision While Elevating the Residence to Meet Today’s Expectations for Style, Comfort, and Quality…the Integrity, Proportions, and Character Remain Intact, Now Enhanced by Refined Finishes, Seamlessly Integrated Contemporary Systems, Forward-Thinking Infrastructure, and Improvements Aligned with City of Sarasota Code…Sleek, Clean & Effortlessly Cool—As Though the 1950s Walked Into 2026 with Style…Expansive New PGT Impact Windows, Sliders & Doors Bathe the Home in Light While Preserving Tranquility…Every Detail Has Been Carefully Considered, Including All New Plumbing with Cast Iron Replacement Under the Slab, All New Electrical, HVAC Ductwork, and Engineered Structural Enhancements to Create an Open Floorplan...Insulated Interior Walls in Key Areas, Blown Attic Insulation, Tankless Water Heater, Fresh Paint, White Oak Style Plank Flooring with Four-Inch Baseboards, Frameless Glass Shower Doors, Custom Walk-In Closets, and Soft-Close Cabinetry Throughout…Curated Quartz Countertops Extend Across the Gourmet Chef’s Kitchen, Catering Pantry, Dry Bar, and Bathrooms…Recently Enhanced with a Brand-New Stainless Steel LG Dishwasher & New GE Profile Refrigerator…Additional Home Features Include Glass Tile Backsplashes, Substantial Kitchen Island with Tile Accent Lighting, and Vented Range Hood…Discreetly Integrated Throughout is a Fully Automated Smart Home System Offering Complete Flexibility—Including Remote Entry Keypads, Wireless Alarm, Ring Cameras, Motion Detectors, Panic Buttons, Remote-Control Ceiling Fans, USB & USB-C Outlets, Nest Thermostat, and Digitally Controlled Irrigation—Allowing the Home to Be Fully Automated or Enjoyed Traditionally at the Owner’s Preference…A Fully Screened Lanai with Custom Tongue & Groove Ceiling Extends the Living Space Outdoors, Complemented by New Epoxy Flooring Leading to the Paver Patio with Pool, Spa & Expansion Concepts Available…The Grounds Have Been Curated with a Six-Figure Landscape & Lighting Package, Fully Fenced, Double-Gated Privacy, Mature Junipers, Lush Clusia Hedges, Olive Trees, Bird of Paradise, and Fragrant Jasmine…A Three-Bedroom, One-and-a-Half-Bath Residence in the Heart & Soul of Arlington Park—Just Blocks to Legacy Trail and Arlington Park & Aquatic Center Hosting Live Music Events Alongside Pickleball, Tennis, Basketball Courts, Playgrounds, a Dog Park, Walking Trails, and Two Pools…Blocks to Sarasota Memorial Hospital, Minutes to Downtown Sarasota, Siesta Key, Longboat Key, Anna Maria Island, UTC Mall, and a Depth of Dining & Cultural Offerings Favored by Locals…Just a Fifteen-Minute Drive to Sarasota-Bradenton International Airport…Weekly Rentals Are Allowed, Not in a Flood Zone, No Storm Damage, No HOA, and Offered Turn-Key Furnished or Thoughtfully Curated to Buyer Preferences…Passed Down Through Only Two Owners Since the 1950s, This Home Represents Stewardship, Architectural Lineage, and Forward-Thinking Living…It’s Timeless, Intentional, and Unmistakably Rare…Schedule Your Private Tour Today & Live a Fuller Life!
Listing is courtesy of: FULLER GROUP (941-961-3100)
Listing Agent: Bo Fuller (941-961-3100)
413 ISLAND CIR, SARASOTA, FL 34242
$3,299,00019 Days on yellowkey MLS ID: A4689084
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2994 Built: 2026Monthly Fee: $4 Tax: $10,496 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$10,496
Remarks: Experience the pinnacle of coastal luxury in this newly constructed masterpiece, ideally located just moments from the beach and a short walk to the vibrant shops, dining, and entertainment of Siesta Village. Situated on an oversized lot, this exceptional property offers added privacy, space, and presence rarely found in this sought-after location. Featuring 4 bedrooms, a private office, and 4.5 bathrooms, the home blends modern elegance with thoughtful design at every turn. A striking first impression begins at the grand entry, where sleek modern pivot doors set the tone for the refined finishes found throughout. Inside, soaring ceilings and expansive living spaces are filled with natural light, while oversized sliding glass doors create a seamless connection between indoor and outdoor living. The chef’s kitchen is a true centerpiece, showcasing custom flat-panel cabinetry, premium Thermador appliances, and a hidden entrance to a spacious walk-in pantry—offering both style and function. Every detail has been carefully curated, from custom built-ins in select bedrooms to the high-end finishes that create an atmosphere of refined comfort. The main living spaces open effortlessly to a private outdoor retreat featuring a resort-style pool and spa, sun shelf, and panoramic screened enclosure with elegant glass railings—perfect for entertaining or relaxing in complete privacy. Car enthusiasts and those in need of extra storage will appreciate the impressive three-car garage with 17-foot ceilings and a built-in car lift, allowing space for a fourth vehicle or additional elevated storage—an exceptional and rare amenity. Designed with both luxury and resilience in mind, this home offers peace of mind in any season. Built elevated and engineered for coastal living, it is equipped with a buried 500-gallon propane tank and a whole-house generator—providing reliable, uninterrupted power during outages. Combined with modern construction standards and durable materials, this residence delivers a level of security and preparedness rarely found in homes this close to the water. Complete with integrated smart home features including a whole-home speaker system and security cameras, this residence offers the very best of modern coastal living. More than just a home, this is a lifestyle opportunity in one of Siesta Key’s most sought-after locations—where luxury meets lasting peace of mind.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Daniel Dabrowski (847-274-2960)
404 S POLK DR, SARASOTA, FL 34236
$1,700,0006 Days on yellowkey MLS ID: A4689616
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2260 Built: 1960 Tax: $16,784 (2025)Community: Lido Beach Div B ResubSingle Family
Taxes:$16,784
Remarks: Welcome home to 404 S Polk — A Phenomenal Coastal Retreat on Lido Key-- Timeless beach charm meets modern ease in a bright, airy home that’s been loved, enjoyed, and meticulously maintained by the same family for 65 years. Impeccably renovated and extended with both families and beachgoers in mind, this 4BR/3BA residence sits on a SPRAWLING CORNER LOT with a grassy front yard and a fenced-in backyard patio and dining area perfect for grilling your fresh catch. Effortless indoor/outdoor living flows from two primary suites (one on the main floor and one upstairs) to a bright and open VAULTED CEILING entryway, a welcoming family room, casual dining area, and a separate formal dining room. IMPACT WINDOWS & SLIDERS provide relief for out-of-state owners. Sleek, updated kitchen featuring granite countertops and stainless steel appliances, alongside updated baths and a NEWER ROOF for peace of mind. An ideal setting for every lifestyle — family living, long-weekend getaways, vacation memories, or endless RENTAL OPPORTUNITIES. Prime location just STEPS from the powdery quartz-sand beaches and turquoise waters of Lido Key. The 2nd-floor balcony is your front-row seat for cool Gulf breezes, beach views, and spectacular bright orange sunsets. Parking is a premium on the beach, but this home has plenty of space with a tandem 2-car garage, and space for 3 cars in the circular driveway! A 4-minute walk to Lido Beach Pavilion: public pool, on-beach dining (including lobster roll favorites), covered seating areas, and convenient beach equipment rentals. St. Armands Circle is about half a mile away, offering restaurants, boutique shopping, live music, and entertainment. Easy access to Sarasota’s Bayfront, theaters, opera, and museums via a short drive over the John Ringling bridge.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
381 BOB WHITE DR, SARASOTA, FL 34236
$2,495,000101 Days on yellowkey MLS ID: A4678714
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3774 Built: 2003Monthly Fee: $89 Tax: $14,487 (2025)Community: Bird Key SubSpa: YesSingle Family
Taxes:$14,487
Remarks: Poised within the prestigious enclave of Bird Key, 381 Bob White Drive is an exquisitely appointed garden residence defined by understated luxury, architectural balance, and refined coastal living. The home offers four bedrooms, three-and-a-half baths, a private office and nearly 3,800 square feet of thoughtfully curated interiors, complemented by a three-car garage and exceptional curb appeal framed by manicured landscaping. Thoughtfully remodeled in 2013, with continuous renovations in 2014 and 2018, the residence showcases rich hardwood flooring throughout, beautifully updated baths, and a timeless palette of finishes that feel elevated and inviting. A paver drive and lush gardens create a gracious arrival, while the home’s flowing layout lends itself equally well to intimate daily living and polished entertaining. The primary suite, on the main level, is a serene retreat with generous proportions, walk-in closets and a spa-inspired bath with dual vanities, a soaking tub and walk-in shower. Direct access to the pool deck enhances the sense of privacy and ease. The split-bedroom design continues upstairs, where a spacious bonus room, two additional bedrooms, and a full bath provide ideal accommodations for guests or flexible living. The gourmet kitchen anchors the home with sleek countertops, custom cabinetry, a breakfast bar and thoughtfully expanded storage, including additional cabinetry and a built-in wine cooler. A sunlit breakfast nook overlooks the pool, while the formal dining room, just beyond the kitchen, offers an elegant setting for gatherings and celebrations. Outdoor living is beautifully curated with a heated pool, a well-appointed outdoor kitchen and multiple seating areas, all surrounded by mature landscaping that creates a sense of privacy and tranquility. A well-water irrigation system with upgraded sprinklers supports the home’s lush, garden-like setting. Ideally, between downtown Sarasota and St. Armands Circle, Bird Key remains one of the area’s desired addresses. Residents enjoy proximity to Bird Key Yacht Club, as well as effortless access to the beaches of Lido Key, Longboat Key and Siesta Key. 381 Bob White Drive presents a rare opportunity to enjoy elevated garden living in one of Sarasota’s iconic communities, where timeless elegance and an exceptional lifestyle converge.
Listing Agent: Louis Wery (941-232-3001)
860 S BENEVA RD, SARASOTA, FL 34232
$725,000216 Days on yellowkey MLS ID: A4665949
REDUCED by $40,000 (5.2%) on 04/22/2026
Bed: 4 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 3177 Built: 1950 Tax: $3,030 (2024)Community: Not Part Of A SubdivisionSingle Family
Taxes:$3,030
Remarks: Rare waterfront footage on over 1.4 acres of tropical landscape.This unique property includes a 2 story, 3 bedroom/ 5 bath house, a 1 bed/1 bath guest house, and a 1900 square foot detached garage. It is ideal for storage, a workshop or recreational equipment. Legacy Trail less than 2 miles away. Bring your e bike business and set up shop here. ( Subject to zoning). The property is located on Phillippi Creek , offering direct access and a unique opportunity for a kayak or paddleboard business in a highly desirable recreational area. ( Subject to zoning) While the property has experienced flooding and requires major renovations, the potential returns make it best suited for investors, builders or buyers ready to undertake a significant project.Bring your vision and tools to transform this into a standout asset in a great location. Close to resturants & shopping.Property sold AS-IS.
Listing Agent: Renee Tope (941-376-1472)
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