Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
5263 AVENIDA DE CORTEZ, SARASOTA, FL 34242
$3,850,00077 Days on yellowkey MLS ID: A4678861
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2018 Tax: $21,844 (2025)Community: Sarasota BeachSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$21,844
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to a residence where inspired design meets the effortless elegance of Island living. Tucked away on the tranquil side of the Siesta Key Village, this extraordinary home places you at the heart of it all while having it all. With World-renowned beaches and the charming village just steps away… you truly can not beat the location. This 4 bedroom, 3100 sq.ft. home boasts a private boat dock, tropical backyard oasis and terraces with sunset views that never fail to inspire. The primary construction of this home was completed in 2018, with a full designer remodel in 2025. This home offers the confidence of modern construction throughout. Levels one through three are concrete block, with a two-by-six wood-frame fourth level and all exterior glass is hurricane impact rated. The home also boasts a standing-seam metal roof, a six-foot privacy wall with keypad-secured metal entry gates. A three-stop elevator services every floor, alongside a striking free-floating steel staircase framed by floor-to-ceiling glass, maintaining open sight-lines across the living spaces. Private bedrooms with en-suite bathrooms are thoughtfully positioned on levels two and four. Each floor opens to a generous covered balcony. Crowning the home is its most captivating feature: a spiral staircase leading from the fourth-floor balcony to a rooftop terrace with sweeping views of Siesta Village, Siesta Beach, Downtown Sarasota, and front-row vantage point to nightly stunning sunsets over the ocean. A comprehensive renovation brings a fresh, sophisticated vision to this home. The updates include new luxury hardwood flooring throughout, designer kitchen complete with dry-bar and a luxurious primary bathroom update. The second level serves as the home’s central gathering space, featuring an open-concept living room, dining area, and kitchen designed for both entertaining and everyday luxury. The kitchen has been elevated with brand-new custom floor to ceiling cabinetry complete with specialty lighting, premium Cambria countertops, as well as new appliances. The space is complimented by a beautifully designed dry bar and pantry for a refined, luxury finish.The high end finishes are complimented by designer furnishings and decor that convey with the sale of the home. At ground level, a two-car garage is complemented by a substantial 440-square-foot covered lanai overlooking a refreshing heated outdoor pool. The addition of an outdoor kitchen and upgraded, easily maintained, turf and stone landscape create seamless indoor-outdoor living and entertainment. Privacy is not an issue as this home boasts lush landscape and an impressive block wall enclosed yard. With Siesta’s gorgeous white sand beaches just a short walk from the home and a private boat dock just across the street enjoying the Ocean is a breeze from this property. The boat dock includes a 10,000-pound lift and space for a second lift, allowing for effortless access to the ocean via a canal. Siesta Key Village is a cherished walkable community rich with dining, boutiques, and local small businesses, including a Market, that evoke feelings of nostalgia. Yet the greatest luxury remains the timeless evening sunset strolls on the soft white sandy beaches. The Island’s effortless serenity reaffirms why Siesta Key is not merely a destination, but an exceptional place to call home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jessica Hoffman (941-400-5778)
3368 SHEFFIELD CIR, SARASOTA, FL 34239
$480,00084 Days on yellowkey MLS ID: A4679367
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1798 Built: 1969Monthly Fee: $8 Tax: $3,379 (2025)Community: Village Green Club EstatesSingle Family
Taxes:$3,379
Elementary School: Wilkinson Elementary
Remarks: Enjoy the best of Sarasota living in this centrally located, fully fenced home with impact windows, circular driveway, with an amazing private outdoor living space that is minutes from shopping, dining, and a short drive to the sugar-sand beaches of Siesta Key. Thoughtfully updated and designed for comfortable everyday living, this home offers a flexible floor plan and inviting spaces both indoors and out. Inside, the light and bright interior features a crisp, clean feel and a desirable split-bedroom, open floor plan. Modern light wood-look laminate flooring flows throughout the home. The entryway includes a convenient coat closet and the open dining and living room combination offers flexibility for entertaining and everyday living. The interior flows seamlessly from the front of the home through the family room and out to the enclosed lanai. The kitchen showcases white shaker cabinets, granite countertops, a glass subway tile backsplash, and stainless steel appliances making it both stylish and functional. The spacious primary suite features tall windows, a large walk-in closet, and an en suite bathroom that offers a shower/tub combo and a thoughtful layout with the toilet and shower separated from the vanity. The guest bedroom is generously sized, and the updated guest bathroom features tile flooring, a large stone shower with glass doors, and granite countertops. Enjoy Florida living year-round with an enclosed, multi-use lanai featuring tile flooring and expansive glass windows that add valuable living space, along with an additional screened rear patio perfect for a more open-air outdoor experience. The vinyl-fenced backyard with lush tropical landscaping completes the home’s rear outdoor oasis. With a great location and stylish updates throughout, this home is ready to be enjoyed. Come see it, feel the charm, and make it your own!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
1625 IDLE LN, SARASOTA, FL 34231
$649,000178 Days on yellowkey MLS ID: A4668964
REDUCED by $16,000 (2.4%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1450 Built: 1960 Tax: $1,562 (2024)Community: NoneSingle Family
Taxes:$1,562
High School: Riverview High
Tax Year: 2024
Remarks: Walk just one mile to the beach from this completely Renovated & Move-In Ready with ample parking for your RV or boat! Every inch of this charming home has been thoughtfully updated with brand new features and high-end finishes. From the plumbing and electrical systems to the appliances, cabinetry, bathrooms, tile flooring, windows, doors, trim, and landscaping—no detail was overlooked. The home also includes stylish furnishings and a beautifully appointed wet bar complete with a wine fridge, perfect for entertaining. The Florida/Sunroom offers flexible space and can easily be converted into a third bedroom to suit your needs. Situated on a quiet cul-de-sac with ample parking for additional vehicles, boats, or recreational toys, this property also boasts no HOA—giving you freedom and flexibility. The spacious yard provides plenty of room for outdoor enjoyment. Prime Location – West of the Trail? and Conveniently located just minutes from shopping, dining, and vibrant Downtown Sarasota, this home offers easy access to all the best of the area. Enjoy the beauty of coastal living with a short one-mile walk or bike ride to Crescent Beach and the world-renowned Siesta Key Beach, all without the congestion of island life. This home is turn key... bring your toothbrush and come enjoy all that Paradise has to offer! All measurements are estimates and are approximate. Buyer and/or Buyer agent confirm all info - seller nor agent makes no guarantees
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000208 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
Listing Agent: Suki Scollo (941-587-2289)
1632 WORRINGTON ST, SARASOTA, FL 34231
$765,000135 Days on yellowkey MLS ID: A4673616
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1547 Built: 1973 Tax: $2,729 (2024)Community: Johnson EstatesSingle Family
Taxes:$2,729
Remarks: One or more photo(s) has been virtually staged. Fantastic West of the Trail location at the secluded end of a tranquil dead-end street on a spacious and rarely available 1/3rd acre lot! As you enter, you’re welcomed by an open and bright great room where skylights and front-to-back windows flood the space with natural light and peaceful nature views. Freshly painted and move-in ready, this one-story 3 bedroom, 2 bath home offers easy, comfortable living close to beaches, downtown, top-rated schools, and everyday conveniences. A rare combination of privacy, space, and unbeatable location.
Listing is courtesy of: LIVE MODERN (941-587-8871)
Listing Agent: Mara Daniel (941-587-8871)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00023 Days on yellowkey MLS ID: A4687301
REDUCED by $100,000 (1.8%) on 04/16/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
6426 COLONIAL DR, SARASOTA, FL 34231
$540,00046 Days on yellowkey MLS ID: A4681958
REDUCED by $50,000 (8.5%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1760 Built: 1961Monthly Fee: $6 Tax: $4,668 (2025)Community: Gulf GateSingle Family
Taxes:$4,668
Elementary School: Gulf Gate Elementary
Remarks: ***PRICE REDUCTION***Welcome to this inviting residence located on a quiet street in the highly desirable Gulf Gate area of Sarasota. This well-situated home offers a comfortable blend of indoor and outdoor living with convenient access to shopping, dining, beaches, major roadways, and public transportation. With the first beach access to the sugar-white sand of Siesta Key being just 1.7 miles away. It is walking distance to several dining establishments and specialty shops unique to Gulf Gate. The interior features a functional floor plan filled with natural light, ideal for both everyday living and entertaining. The newly renovated kitchen serves as a central gathering space with updated finishes and a fresh, modern feel while flowing effortlessly into the living and dining areas. Bedrooms are well-proportioned and adaptable to a variety of lifestyle needs, featuring a mother-in-law suite with private bathroom and a separate entrance. Large fenced in backyard providing privacy, with outdoor space that offers flexibility to relax, entertain, or personalize, there is plenty of room for a pool, tiki hut and volleyball court the possibilities are endless. Whether used as a primary residence, second home, or investment opportunity, this home presents an excellent opportunity to enjoy Sarasota living.
Listing is courtesy of: PREFERRED PROPERTIES OF SARASOTA (941-951-2580)
Listing Agent: Kellie Mosier (941-264-3484)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00024 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,00095 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
Listing Agent: Harriet Stopher (404-316-8944)
2534 GROVE ST, SARASOTA, FL 34239
$2,499,000245 Days on yellowkey MLS ID: A4662120
2 Days Off yellowkey (back on 4/16/2026)
Bed: 7 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 4615 Built: 2025 Tax: $4,033 (2024)Community: South GateSpa: YesSingle Family
Taxes:$4,033
Elementary School: Southside Elementary
Remarks: Welcome to 2534 Grove Street, a new construction residence blending modern design with everyday livability in one of Sarasota’s most desirable neighborhoods. The open-concept main level features generous entertaining space with a gourmet kitchen, dining area, and living room that transitions seamlessly to the covered lanai and private courtyard-style backyard. The spacious first-floor primary suite provides convenience and privacy. Upstairs, a second lounge offers flexibility for media, office, or guests, along with additional ensuite bedrooms. Located in the Southside School district and just minutes from Downtown Sarasota, Siesta Key, and Lido Key. Brand new, move-in ready, and thoughtfully designed for the way you live.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Steven Moore (401-767-7180)
4938 COMMONWEALTH DR, SARASOTA, FL 34242
$2,900,00046 Days on yellowkey MLS ID: A4683758
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2169 Built: 1984 Tax: $12,150 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$12,150
Remarks: Experience the pinnacle of waterfront luxury on Siesta Key’s prestigious Grand Canal. This meticulously reimagined residence at 4938 Commonwealth Drive offers a rare blend of modern sophistication, structural integrity, and complete peace of mind. Extensively transformed both structurally and aesthetically, the home welcomes you into an expansive open-concept design filled with natural light. The newly expanded kitchen serves as the heart of the home, offering abundant cabinetry and storage, a double oven, generous pantry storage, striking custom beam detail, an open breakfast bar, and direct access to the wraparound decking—creating seamless indoor-outdoor living and effortless entertaining. A stylish powder room has also been thoughtfully added. New hurricane-impact windows and sliding glass doors frame the interiors, while designer flooring flows beautifully throughout both levels. Major system upgrades elevate the home’s value and efficiency, including a brand-new roof and a comprehensive solar power system with battery storage. A fresh, contemporary interior palette enhances the clean architectural lines and airy coastal feel. The lower level adds over 1,300 square feet of legal non-conforming living space with its own private entry, garage access, and elevator connection to the main living areas, leading directly to the pool deck. Redesigned for modern functionality, this space features a spacious family entertainment area, custom bar, and an additional guest suite with a walk-in closet and full bath—ideal for extended family, guests, or a private retreat. Outdoor living is equally impressive. The private backyard sanctuary showcases a heated pool and spa with a new heater and filtration system, sleek updated decking, professional landscaping, and premium artificial turf for effortless maintenance. For the boating enthusiast, the deep-water dock and boat lift provide direct access to the Intracoastal Waterway and open waters of Sarasota Bay, delivering the ultimate waterfront lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
2224 BAHIA VISTA ST #E6, SARASOTA, FL 34239
$214,50058 Days on yellowkey MLS ID: A4683095
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 982 Built: 1979 Tax: $2,936 (2025)Community: Cordova Gardens IiCondo
Taxes:$2,936
Elementary School: Alta Vista Elementary
Remarks: Seller Offers $7500 closing credit to Buyer for new (Condo Approved) patio Sliders. Stylishly updated 2 bed, 2 bath condo just minutes from vibrant downtown Sarasota! Light-filled and airy, this inviting, quiet, second floor unit offers a fantastic location near top restaurants, boutique shopping, and only a 15 minutes walk to Sarasota Memorial Hospital-ideal for snowbirds, healthcare professionals, or anyone craving convenience with a touch of tranquility. Enjoy 2 tastefully renovated bathrooms featuring light cabinetry, classic subway tile, glass shower doors, and modern fixtures. The lofted ceiling and transome windows provide light and spaciousness. The kitchen shines with stainless stell appliances, granite countertops, a new Kohler sink, and updated hardware--perfect for whipping up meals or entertaining guests. Two screened balconies let you soak in the peaceful wooded views and Florida Breezes. Additional updates include new interior doors, window treatments, upgraded electrical outlets and switches plus a clever lofted attic space in the primary bedroom--tucked behind a charming barn door for a bonus storage or a cozy reading nook. Whether you're looking for a seasonal getaway or a full-time retreat, this move-in ready condo offers the best of both worlds: City energy and a quiet escape. Come enjoy the Sarasota lifestyle you've been dreaming of!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lena Oberwetter (608-444-9009)
1773 SOUTHWOOD ST, SARASOTA, FL 34231
$600,00097 Days on yellowkey MLS ID: A4677227
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1431 Built: 1986 Tax: $4,655 (2025)Community: FlorenceSingle Family
Taxes:$4,655
Remarks: Under contract-accepting backup offers. Charming Remodeled Home in beautiful Sarasota. Welcome to this recently remodeled 3-bedroom, 2-bath home ideally located at 1773 Southwood Street in Sarasota, just moments from the natural beauty and walking trails, fishing piers and kayak launch of Phillippi Estate Park. Renovated in 2022, this residence blends modern updates with a warm, inviting coastal vibe. The bright and open interior features a stylish, updated kitchen with crisp white cabinetry, sleek countertops, stainless steel appliances, and a striking tile backsplash—perfect for everyday living and entertaining alike. Recessed lighting and thoughtful finishes throughout enhance the home’s clean, contemporary feel. The spacious layout offers three comfortable bedrooms and two updated bathrooms, providing flexibility for family, guests, or a home office. Durable flooring and neutral tones create a move-in-ready space that’s both functional and stylish. Outside, the home’s cheerful exterior color, mature landscaping, and private driveway add curb appeal and character, while the quiet neighborhood setting offers a peaceful retreat close to everything Sarasota has to offer. Conveniently located near beaches, fishing piers, dining, shopping, and downtown Sarasota, this home is an excellent opportunity to enjoy Florida living with modern comforts in a prime location. Home can not convey until April 1.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Tracey Larsen (847-533-8708)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000182 Days on yellowkey MLS ID: A4668223
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $10,871 (2025)Community: CasarinaCondo
Taxes:$10,871
Remarks: Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling to this home. A wall mounted television with Sonos audio provides family entertainment. The spacious primary bedroom with a Closet Tech designed walk-in closet opens to a large bathroom with custom cabinets, dual sinks and large walk-in shower. A third bedroom was created during the recent remodel and includes a built-in under window desk. The full-sized laundry room allows for plenty of storage. Luxury vinyl flooring was installed in 2020 in all public rooms. Impact windows were added in 2016. Electric blinds can close off the sliding glass doors to the outside view while all other windows have custom designed plantation shutters. Crown molding and solid wood doors are found throughout the unit. Casarina is an 89-unit condominium complex that sits on 200 feet of private beach and encompasses 7 acres of tropical landscaping. The complex has a clubhouse with kitchen. Spend your days enjoying the beachside pool and spa, play a game of pickleball on one of the two lighted tennis courts, or relax on the island’s famous crystal sand beach. Hop on the free trolley to enjoy the dining, shopping and entertainment at Siesta Key Village. CASARINA ALLOWS OWNERS ONE SMALL PET.
2852 CAPTIVA DR, SARASOTA, FL 34231
$559,000248 Days on yellowkey MLS ID: A4661671
REDUCED by $16,000 (2.8%) on 04/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2033 Built: 1975Monthly Fee: $4 Tax: $5,128 (2025)Community: Gulf Gate WoodsSpa: NoSingle Family
Taxes:$5,128
Remarks: NEW PRICE ON THIS BEAUTIFULLY UPDATED AND MOVE-IN READY GULF GATE POOL HOME WITH 2025 TILE ROOF! ADDITIONAL 2025/26 UPDATES INCLUDE UPGRADED ELECTRICAL SERVICE, NEW DUCTWORK, CARPET, BATHS, EXTERIOR/INTERIOR PAINT, DISHWASHER, DRIVEWAY, FENCE, LANDSCAPING AND MORE! Located in the sought-after Gulf Gate Woods community, this beautifully refreshed 3-bedroom, 2 full bathroom residence blends timeless design with modern upgrades, all nestled just minutes from world-renowned Siesta Key Beach. The bright and spacious living room welcomes you with natural light and new neutral tone plush carpet. The open-concept kitchen features a just completed raised ceiling with recessed lighting and additional 2017 improvements including stainless steel appliances, soft close cabinetry, and granite countertop, and flows seamlessly into a generous breakfast room and separate dining room too! The thoughtful split-bedroom floor plan ensures privacy, with the primary suite positioned separately from the guest bedrooms. The primary bedroom features a renovated en-suite bath with sleek subway tile shower enclosure, on-trend black fixtures, new floating vanity and modern finishes. Two additional bedrooms are located on the opposite wing and share an updated full bath with a granite topped vanity. The additional 24x10 bonus room is a great space for entertaining or relaxation, with windows out to your own private oasis which includes the sparkling pool and screened lanai. A 2023 water heater ensures energy efficiency, while the spacious interior laundry room adds everyday convenience. The prior owner replumbed the home with PVC pipes. The attached two-car garage includes abundant cabinetry, ideal for storage and organization. This home is in the X flood zone and is high and dry. Gulf Gate Woods is a well-established neighborhood known for its sidewalks, streetlights, and friendly sense of community. Zoned for A-rated schools, this prime Sarasota location places you within 10 minutes of Siesta Key Beach, downtown Sarasota, the Legacy Trail, golf courses, fitness centers, Sarasota Memorial Hospital, fine dining, UTC and the charming shops and restaurants of Gulf Gate Village. Whether you're seeking a full-time residence, seasonal getaway, or a smart investment, this home offers flexibility and would also make an excellent option for a long or short-term rental.
Listing Agent: Lenore Treiman (941-356-9642)
1921 MONTE CARLO DR #302, SARASOTA, FL 34231
$549,000308 Days on yellowkey MLS ID: A4655742
REDUCED by $26,000 (4.5%) on 04/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1720 Built: 2006 Tax: $6,041 (2025)Community: Phillippi Landings ACondo
Taxes:$6,041
Remarks: INCREDIBLE VALUE - this beautifully remodeled third-floor luxury residence with water view in the gated waterfront community of Phillippi Landings is perfectly situated West of the Trail and just minutes to the world-renowned beaches of Siesta Key. Nestled along the Phillippi Creek with direct access to Sarasota Bay and just minutes to the Philippi Farmhouse market and the Landings Shopping Center with its vast array of dining and shopping options. This 2 bedroom plus den, 2 bath condo offers the ideal blend of privacy, convenience, and resort-style living. From the moment you enter via direct elevator access to your private foyer entrance, you are welcomed by an open and airy floor plan, porcelain tile flooring, and an inviting coastal aesthetic. The beautifully updated kitchen features granite countertops, stainless appliances, and rich wood cabinetry, offering both style and function for everyday living and entertaining. Step into the spacious living area that opens to a private covered and screened balcony with peaceful water view, ideal for enjoying morning coffee or a glass of wine at sunset. The split-bedroom layout offers exceptional privacy, with two generously sized bedroom suites. The primary suite is a true retreat, offering tranquil water view, two large walk-in closets, and a spa-style bath with a jetted soaking tub, custom walk-in shower, and private water closet. A flexible bonus space off the main living area provides the perfect nook for a home office, den, reading lounge, or secondary dining area. Impact doors and windows throughout. Beautiful wood plantation shutters. Enjoy the convenience of under-building assigned parking and a private storage unit. This home is move-in ready and ideal as a primary residence, seasonal escape, or investment opportunity. Life at Phillippi Landings is exceptional - the community is 10 acres and offers a resort-style heated pool and spa, a well-equipped fitness center, clubhouse, and an expansive waterfront promenade perfect for evening strolls beneath swaying palms. For boating and nature enthusiasts, the community provides kayak launch access and private storage racks—an invitation to explore the peaceful waterways of Phillippi Creek and beyond. The lush, manicured grounds and tropical landscaping create a tranquil, private atmosphere while placing you just minutes from Southside Village, downtown Sarasota, and the vibrant shopping and dining of UTC Mall. This exceptional location, paired with a refined, low-maintenance lifestyle, offers the best of coastal Florida living.
306 ISLAND CIR, SARASOTA, FL 34242
$1,825,0002 Days on yellowkey MLS ID: A4689514
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2392 Built: 1952Monthly Fee: $4 Tax: $18,781 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$18,781
Remarks: A truly rare offering, this waterfront residence is uniquely positioned with 133 feet of water frontage on two sides, creating an unparalleled sense of privacy and serenity. Nestled on prestigious Palm Island, in the heart of Siesta Key, this property embodies the ultimate coastal lifestyle. This spacious four-bedroom, three-bathroom home is thoughtfully designed, featuring two en-suite bedrooms alongside two additional generously sized guest rooms. Expansive windows invite in natural light while framing tranquil water views throughout the home. Boating enthusiasts will appreciate the private dock and boat lift at the rear of the property, with additional capacity to add a second dock and lift along the side canal—an extraordinary advantage rarely found. Ideally located, the home offers effortless access to world-renowned Siesta Key Beach and the vibrant Siesta Key Village, placing dining, shopping, and entertainment just a leisurely stroll away. Recently renovated, the residence showcases a large resort-style pool with spa, low-maintenance tropical landscaping, and updated finishes including new appliances, cabinetry, and more—creating a move-in-ready retreat. The peaceful wrap around canal provides a private sanctuary where nature and waterfront living converge. Set on an expansive ~14,000 square foot lot, this property is also offered at a compelling value at just above land pricing, presenting a remarkable opportunity for a custom luxury estate. Building plans are available and this lot is build to suit.
3233 BENEVA RD #104, SARASOTA, FL 34232
$127,4501 Day on yellowkey MLS ID: A4690227
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1978 Tax: $1,932 (2025)Community: Village Brooke Sec 3Condo
Taxes:$1,932
Remarks: Home without the homework is yours with this condo. You'll love the beautifully groomed grounds here. You can live here affordably. Look at what the maintenance fee includes!!! All the neighbors have been so nice and helpful. Picturesque view from your lanai overlooking a picnic area and pond...or...you can bask in the sunshine poolside. Minutes to one of the best beaches in the world.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Debbie Roth (941-713-0522)
2609 WOODGATE LN #K4, SARASOTA, FL 34231
$164,9002 Days on yellowkey MLS ID: N6143915
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1982Monthly Fee: $588 Tax: $2,358 (2025)Community: Pinewood Village IxCondo
Taxes:$2,358
Remarks: You're five miles from one of the best beaches in America. You just didn't know you could afford to live this close. Ground floor, pool-facing, fully furnished 2BR/2BA in Pinewood Village. Walk out your lanai and you're at the pool. Walk out the front door and Siesta Key Beach, St. Armands Circle, Marina Jack, and downtown Sarasota are minutes away. The best-priced unit in the community — and better than anything else available right now. Ground floor instead of stairs. Tile throughout instead of carpet. Fully furnished and move-in ready the day you close. The only comparable unit in this section spent 385 days on the market and just went pending. This one won't last that long. Flood Zone X. No flood insurance required — a real financial advantage in today's Sarasota market. Outside your door, Sarasota delivers everything. Sarasota Memorial Hospital three miles away. Phillippi Estate Park around the corner. The Van Wezel, the Asolo, the Ringling, the Opera — ten minutes from your front door. The restaurants, the boutiques of St. Armands, the farmers markets, the sailing — all of it yours. Pinewood Village itself overdelivers at this price. Heated pool, fitness center, sauna, shuffleboard, full clubhouse with kitchen. HOA covers cable, water, sewer, trash, pest control, exterior maintenance and building insurance. Phillippi Shores Elementary, Brookside Middle, Riverview High. Association approval required. Sold As-Is. Seller motivated.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jeffery K. Twigg, Pa (941-412-6505)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,0002 Days on yellowkey MLS ID: A4689977
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1710 Built: 1960Monthly Fee: $17 Tax: $6,279 (2025)Community: South GateSingle Family
Taxes:$6,279
Remarks: Stunning, mid-century modern home in highly desirable South Gate with views you must see to believe! If you could have picked one of the best lots in South Gate back in the 1960’s this may have been it. The two-bedroom plus office, two bath home sits on a bluff overlooking a wide portion of Philippi Creek including a large aquatic preserve. You’ll be mesmerized by long, unobstructed views in every direction. A nature lovers delight and absolutely intoxicating. But while location is important, there are many more features in this classic home to consider. Entering through the large foyer you’ll immediately notice beautiful terrazzo floors throughout and a great room with vaulted ceilings. There’s an adjacent dining area off the kitchen and all of these spaces look out through what appears to be a “wall of glass” dedicated to the world class view of flora and fauna. The primary bedroom also has views and access to the back yard and the primary bathroom has been upgraded with a separate tub and walk in shower. The den/office can be made more private with sliding pocket doors and function as a guest bedroom. It even has a dedicated, enclosed patio and garden space. There’s an attached, oversized garage with room for your workshop and a double wide driveway with plenty of parking. While this home has been appropriately updated and improved over the years you’ll find it’s all been done with a great sensibility to the original intent, quality and “hipness” so many are learning to appreciate, again.
Listing Agent: Barbara May (404-822-9264)
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