Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3410 S SCHOOL AVE, SARASOTA, FL 34239
$699,999167 Days on yellowkey MLS ID: A4671779
1 Days Off yellowkey (back on 4/23/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,754
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Sherri Mills (941-350-7112)
3339 SHEFFIELD CIR, SARASOTA, FL 34239
$490,00048 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
Tax Year: 2025
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
$1,450,000202 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
Elementary School: Phillippi Shores Elementary
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
$249,000170 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
$5,595,000139 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
High School: Riverview High
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.
5770 MIDNIGHT PASS RD #C601, SARASOTA, FL 34242
$1,395,000148 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
$649,900146 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
$515,00079 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
$645,900101 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
$3,299,00022 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
$1,700,0009 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
$2,495,000104 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
High School: Booker High
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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Louis Wery (941-232-3001)
860 S BENEVA RD, SARASOTA, FL 34232
$725,000219 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)
2304 RINGLING BLVD #101, SARASOTA, FL 34237
$145,000181 Days on yellowkey MLS ID: A4670262
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 552 Built: 1965Monthly Fee: $600 Tax: $1,641 (2024)Community: Garden AptsSpa: NoCondo
Taxes:$1,641
Remarks: Welcome to this charming ground floor, 1 bed 1bath condo within walking distance of all of Sarasota’s splendor! This unit is in excellent condition and boasts tile floors throughout. Newer kitchen appliances, counter tops and cabinets. The association has just updated the laundry facility with brand new washers and dryers. This home also has its own parking space and there is guest parking on site. It is perfect as a weekend get-a-way, private residence and has an excellent long-term rental history. Whether you are an investor or an empty nester, this condo is ready for occupancy!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
4301 S LOCKWOOD RIDGE RD, SARASOTA, FL 34231
$859,000159 Days on yellowkey MLS ID: A4672535
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3406 Built: 1970 Tax: $8,304 (2024)Community: Flora VillaSpa: NoSingle Family
Taxes:$8,304
Remarks: A welcoming Sarasota residence that blends spacious indoor living with a true resort-style outdoor oasis, all positioned in one of the most convenient and desirable locations in Sarasota County. Thoughtfully decorated and beautifully maintained, this home opens with a charming courtyard entrance that sets an immediate tone of warmth and sophistication. Inside, Brazilian hardwood floors flow throughout the living spaces, complementing abundant natural light and an open, flexible layout. The home offers large bedrooms and two versatile flex rooms ideal for a den, office, playroom, hobby studio, gym, storage, or an additional guest suite. Upgraded interior doors add a refined touch, while the master bedroom features a custom built-in closet system for exceptional organization. The kitchen impresses with an epoxy river kitchen-island countertop paired with a copper farmhouse sink, creating a stunning focal point for both cooking and entertaining. Additional highlights include Mexican tile accents, a generous walk-in pantry, and thoughtful design that blends character with function. Step outside to discover the crown jewel of the property: a private, resort-style lagoon pool designed for the ultimate Florida lifestyle. This expansive 20,000-gallon saltwater pool showcases a rockwall waterfall, a dolphin fountain, bench seating, and a sun shelf for lounging. With outstanding sun exposure perfect for sunbathing, the pool is surrounded by an oversized pavered patio offering abundant space for lounge seating and entertaining. A 340-sq-ft screened lanai with a ceiling fan extends the indoor living space and provides a comfortable transition to the home’s breathtaking outdoor retreat. Mature tropical landscaping creates lush privacy, enhancing the serene ambiance and delivering the feeling of a secluded paradise. Completing the outdoor experience is a tiki bar with bartop seating and built-in lighting, ideal for evening cocktails, weekend celebrations, and memorable nights under the Florida sky. The property also includes a wired utility and workshop shed, plus an irrigation system for easy landscape maintenance. Beyond its impressive features, the location elevates this home even further. Residents are less than 10 minutes from Downtown Sarasota’s world-class dining, boutique shopping, waterfront parks, and vibrant cultural arts district. The world-famous Siesta Key Beach, renowned for its powdery white quartz sand, is approximately 10 minutes away, offering effortless beach days. The upscale UTC Mall and surrounding dining and entertainment district are about 15 minutes away, while St. Armands Circle and Lido Beach are roughly 20 minutes away for oceanfront dining and luxury leisure. Everyday conveniences, including Sarasota Memorial Hospital, grocery stores, parks, boat ramps, and I-75, are all within minutes, making this home a rare combination of comfort, style, and accessibility. Beautifully updated, move-in ready, and enhanced with an outdoor living experience rarely found in this location, this property presents an exceptional opportunity to embrace the best of Sarasota living! ROOF 2020. Two of three HVACs 2023. PVC plumbing throughout.
Listing Agent: Janette Schafer (954-298-7791)
5474 RIVERBLUFF CIR #V35, SARASOTA, FL 34231
$219,900189 Days on yellowkey MLS ID: A4669393
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1971 Tax: $2,363 (2024)Community: Strathmore Riverside IVilla
Taxes:$2,363
Remarks: Welcome to Strathmore Riverside Villas, a vibrant 55+ community perfectly situated in the heart of Sarasota. This spacious two-bedroom, two-bath villa offers the ideal blend of comfort, convenience, and endless potential. Light, bright, and airy, the home features an open-concept layout with generous room sizes and an inviting flow throughout. The enclosed lanai, complete with both windows and screens, provides a wonderful year-round living space; perfect for morning coffee, relaxing afternoons, or entertaining friends. The villa also includes a one-car carport and a separate storage and laundry area, offering privacy, security, and plenty of extra space. With just a touch of personalization, this residence can truly shine. The community itself is beautifully maintained and lushly landscaped, creating a serene and welcoming atmosphere surrounded by green space. Strathmore Riverside Villas is known for its active lifestyle and warm sense of community. Residents enjoy a wealth of amenities, including a heated geothermal pool overlooking the marina, clubhouse, fitness center, library, meeting rooms, sauna, and billiards. There’s always something happening here; social events, card games, bingo nights, potlucks, concerts, dancing, and more. Boat docks are available on a first-come, first-served basis for just $1,344 per year, and the community is pet-friendly. The location couldn’t be better; just minutes from shopping, hospitals, and the world-famous Siesta Key Beach, as well as the rich cultural attractions of downtown Sarasota, including opera, ballet, symphony, and live theatre. Whether you’re looking for a full-time residence or a seasonal getaway, this villa lives like a single-family home and offers the perfect opportunity to enjoy Florida’s relaxed coastal lifestyle. Don’t wait; schedule your private tour today and discover the charm of Strathmore Riverside Villas.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000178 Days on yellowkey MLS ID: A4669078
REDUCED by $250,000 (3.0%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4705 Built: 2021Monthly Fee: $13 Tax: $68,556 (2025)Community: San Remo EstatesSpa: YesSingle Family
Taxes:$68,556
Remarks: Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal contemporary residence blends clean architectural lines with warm, natural finishes, ideal for buyers seeking newer construction, move-in-ready condition, and hurricane-resilient design in a prime location. Positioned on protected sailboat water with no fixed bridges, the property offers seamless access to Sarasota Bay and a short, unobstructed ride to the Gulf, making it perfectly suited for avid boaters. Spanning approximately 4,750 square feet under air, with nearly 3,000 additional square feet of outdoor living space, the home is designed around the indoor-outdoor lifestyle today’s luxury buyers prioritize. The open-concept layout is anchored by a chef’s kitchen featuring a sculptural marble island and Sub-Zero and Wolf appliances, flowing effortlessly into a great light-filled room with a stone fireplace, custom built-ins, and floor-to-ceiling glass sliders that open to expansive terraces. A temperature-controlled wine room with 1,800-bottle capacity adds a refined touch, while the dining space creates a striking architectural focal point. The primary suite offers true resort-style living, with private access to both a tranquil courtyard with spa and sauna and the waterfront pool terrace. Inside, a custom walk-in closet and spa-inspired bath reflect the level of finish expected in a luxury retreat. The second level features three additional bedrooms, a flexible gym or office, and a loft-style workspace, providing versatility for modern living. Outdoors, the illuminated saltwater pool with a glass wall, newly enhanced outdoor kitchen, and expansive entertaining areas create a private waterfront oasis. The deep-water dock is equipped with a 20,000-pound boat lift, dual jet ski lifts, and a floating dock, delivering a true boating lifestyle. Additional highlights include a three-car garage with a lift, epoxy flooring, and custom storage. A fully integrated smart home system, featuring programmable lighting and shades, whole-home audio, Apple TV integration, a generator, and high-speed WiFi, meets the expectations of today’s tech-forward buyer. Furniture is available separately to create a more turnkey concept. Located within San Remo Estates, the home offers a rare balance of privacy and central convenience. Just minutes from Siesta Key via the nearby North Bridge, beach access becomes part of everyday life. Set on a deep-water basin seconds from Sarasota Bay, the property provides protected docking with immediate access to open water and a short ride to the Gulf. Southside Village and Downtown Sarasota are both a quick drive away without the need to cross any bridges, offering boutique shopping, cafés, acclaimed dining, and a vibrant arts and cultural scene. Everyday conveniences, including top-rated schools, Sarasota Memorial Hospital, and key corridors like US-41 and I-75, are all within close reach. This is a location that seamlessly connects protected waterfront living with the very best of Sarasota.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
5500 MERRIMAC DR, SARASOTA, FL 34231
$1,685,00057 Days on yellowkey MLS ID: A4684914
REDUCED by $85,000 (4.8%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 1974 Tax: $6,537 (2025)Community: Phillippi Gardens 08Spa: YesSingle Family
Taxes:$6,537
Remarks: Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.
Listing Agent: Steve Abbe (941-400-3969)
6204 MIDNIGHT PASS RD #205, SARASOTA, FL 34242
$775,000111 Days on yellowkey MLS ID: A4676979
REDUCED by $4,000 (0.5%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1979Monthly Fee: $1,243 Tax: $6,173 (2025)Community: Siesta Dunes BeachCondo
Taxes:$6,173
Remarks: Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just how close you are to the beach. Enjoy peace of mind with recent upgrades, including a newer AC, newer roof, and brand-new impact windows (2025). The unit includes a covered parking space and the community provides private beach access and beach chairs, so you’re ready to enjoy the Siesta Key lifestyle from day one. With weekly rentals allowed, this property offers excellent rental potential in a highly desirable beachfront community. Whether you’re relaxing on the sand or generating income, this Siesta Dunes condo checks all the boxes for coastal living which will not disappoint.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
4817 OCEAN BLVD, SARASOTA, FL 34242
$1,949,000171 Days on yellowkey MLS ID: A4671593
1 Days Off yellowkey (back on 4/12/2026)
REDUCED by $46,000 (2.3%) on 04/07/2026
Bed: 4 Bath: 3.0 Gar: 5 Liv Area Sq Ft: 2657 Built: 1982 Tax: $8,709 (2025)Community: Lake RittwoodSpa: YesSingle Family
Taxes:$8,709
Remarks: Under contract-accepting backup offers. Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart of Siesta Key Set on a tranquil spring-fed lake just moments from Siesta Beach and the Village, this flood resilient and meticulously maintained coastal residence offers year-round enjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, it blends timeless coastal style with exceptional quality and peace of mind. Inside, an open layout showcases engineered oak hardwood floors, solid maple cabinetry, Santorini quartzite countertops, and Thermador appliances. The primary suite features serene lake views and a spa-inspired bath wrapped in Calacatta Oro tile. Outdoors, enjoy a heated saltwater pool, Hot Springs spa, and Tiki Hut with lighting, TV, and sound — perfect for entertaining. The maintenance-free backyard, astro turf lawn, and SWAT mosquito misting system ensure comfort and convenience year- round. A true standout, the air-conditioned 5-car garage with lifts, compressor, and 200mph- rated doors is a car enthusiast’s dream. With a 2019 roof, impact windows and doors, natural gas utilities, and smart home features, this home delivers effortless coastal luxury. Whether as a full-time residence or a seasonal escape, 4817 Ocean Blvd delivers a lifestyle that is uniquely Siesta Key — coastal elegance, lakefront tranquility, superior craftsmanship, and the freedom to simply lock, leave, and enjoy.
Listing Agent: Gerard Healy (941-961-2240)
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