Location: Sarasota , 34242
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1500 COVE II PL #524, SARASOTA, FL 34242
$849,900113 Days on yellowkey MLS ID: A4676444
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $8,269 (2025)Community: Midnight Cove IiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,269
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: RARE OPPORTUNITY TO OWN A 3 BEDROOM ON SIESTA KEY! With Deeded beach access and one-week rentals! Maximize your investment while enjoying this fantastic 2 level townhouse in Midnight Cove II. Enjoy the views from your screened lanai or open air balcony on the second level. This unit offers space! Great sized living and dining areas, nice large, bright kitchen with updated appliances, powder room on the main level plus 2 more full baths upstairs. In unit laundry, deeded covered parking and offering a great rental history! Ideally located for quick deeded access to Crescent Beach just across the street! Midnight Cove II is a highly desirable community offering a marina with slips available and direct access to the intracoastal. Other amenities include tennis, pickleball, basketball court, fitness center and large heated pool. In addition, there is a grill and picnic area, car wash, pet walk, canoe storage and more! The property features beautiful mature landscaping with frontage on the intracoastal with paths and seating throughout the property. Midnight Cove II offers fully funded reserves, onsite rentals and management, and a rental friendly environment to maximize your income. Milestone Report is complete. Roof was replaced in fall of 2025 as well. Offered turnkey furnished with a small list of exceptions. Great opportunity - don't miss it!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Kim Sheridan (941-313-0262)
1400 COVE II PL #631, SARASOTA, FL 34242
$660,00073 Days on yellowkey MLS ID: A4681753
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,509 (2025)Community: Midnight Cove IiCondo
Taxes:$5,509
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to the most adorable condo on world famous SIESTA KEY. Start enjoying the island lifestyle in this TURNKEY condo with GREAT WATER VIEWS and pool views! ***WEEKLY RENTALS***Very comfortable open floor plan with balcony to sip your cocktails and relax. The PRIVATE DEEDED BEACH ACCESS to the quartz sand Siesta beach in priceless. Midnight Cove offers tennis, pickleball, barbecue areas, fitness, pool, on site management, boat docks and more. Very importantly, there was no storm damage. Take the free trolley to Siesta Village or walk to the south village restaurants and shops. Downtown Sarasota and St Armand's Circle just a short drive away. An excellent opportunity for your vacation getaway or investment property.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
5507 CONTENTO DR, SARASOTA, FL 34242
$1,775,00062 Days on yellowkey MLS ID: A4683288
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSpa: NoSingle Family
Taxes:$15,484
Middle School: Sarasota Middle
Remarks: A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***
9011 MIDNIGHT PASS RD #228, SARASOTA, FL 34242
$399,0001106 Days on yellowkey MLS ID: A4566083
1 Days Off yellowkey (back on 4/21/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 783 Built: 1974 Tax: $4,116 (2022)Community: Sunrise Cove Sec 4Condo
Taxes:$4,116
Tax Year: 2022
Remarks: Under contract-accepting backup offers. The Lowest Entry Price on the Water! Investor Alert: This is the lowest-priced condo currently available in Sunrise Cove, making it the absolute best entry price for a highly desirable waterfront investment on Siesta Key. Direct Intracoastal Waterway views from your lanai, living area, and bedroom. Enjoy sunrises over Little Sarasota Bay and sunsets at Turtle Beach (deeded beach access across the street). Fully furnished 1-bedroom, 1-bathroom unit featuring an updated kitchen (stainless steel appliances) and a custom-built queen Murphy Bed for maximum sleeping capacity. Rental Income Generator: Community allows lucrative one-month rentals with convenient on-site management Unbeatable Amenities • 2 bayside heated pools • Lighted tennis and pickleball courts • Large clubhouse with fitness rooms and billiards • Boat docks available for a low yearly fee • Adjacent to Turtle's Restaurant and Ophelia's Restaurant • Free trolley stop across the street for easy access to Siesta Key Village and Public Beach. Secure your piece of Siesta Key waterfront real estate at a game-changing price!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$525,0003 Days on yellowkey MLS ID: A4690769
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $5,340 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$5,340
Remarks: Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
19 WHISPERING SANDS DR #1104, SARASOTA, FL 34242
$1,000,00089 Days on yellowkey MLS ID: A4679738
0 Days Off yellowkey (back on 4/20/2026)
REDUCED by $125,000 (11.1%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,440 Tax: $6,142 (2025)Community: Whispering SandsCondo
Taxes:$6,142
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT!! Welcome to this beautifully remodeled 11th floor GULF FRONT Whispering Sands tower residence – just one floor below the penthouse level – where sweeping, unobstructed FULL Gulf views meet breathtaking, colorful sunsets that paint the sky each evening. This light filled 2BR/2BA condo is the perfect combination of refined coastal style with effortless, comfortable living. The bright open kitchen is designed for both entertaining and everyday elegance, featuring an expansive, 8-foot breakfast bar, granite countertops, Whirlpool, GE & KitchenAid appliances, recessed lighting, and a convenient built-in corner workspace. NEW 2024 hurricane impact sliders frame your private, enclosed 24’ Gulf front balcony – the ideal space for enjoying peaceful morning coffee or sunset cocktails above the shoreline. The tranquil primary suite features a walk-in closet and beautifully remodeled ensuite bath with spacious dual vanity and glassed walk-in shower. A set of French doors with privacy shades leads to a flexible guest suite with twin Murphy beds & built-ins, easily transitioning from private office to welcoming bedroom. A second guest bath entry creates a true ensuite experience. Thoughtful upgrades in this unit include track lighting, textured ceilings, remote-controlled overhead fans, and a whole-house water filtration system. 2024 HVAC. Whispering Sands is a premiere 55+ Gulf front property on the westernmost point of Siesta Key, featuring 800’ of private quartz sand beach, 2 heated pools, clubhouse and Tower Lounge – both of which are in the initial stages of being completely remodeled – beachside Tiki Hut, gas grills, shuffleboard, canoe/kayak storage, and onsite management. You’re also ideally just around the corner from the colorful boutiques and dining options of Siesta Key Village! Don’t miss this rare opportunity to own this sophisticated Gulf front residence that captures a true resort lifestyle while remaining warm, welcoming, and wonderfully livable.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
6703 MIDNIGHT PASS RD #208, SARASOTA, FL 34242
$299,999185 Days on yellowkey MLS ID: A4669017
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 702 Built: 1974 Tax: $3,626 (2024)Community: Sea WindsCondo
Taxes:$3,626
Tax Year: 2024
Remarks: LOWEST PRICE ON SIESTA KEY FOR A ONE BR CONDO OFFERING SHORT TERM RENTALS! Siesta Key Beach is calling you…experience the allure of coastal living at the quaint Sea Winds complex, conveniently located along Midnight Pass Rd., just a short walk to the world-renowned Siesta Key beach! This prime beach investment offering the opportunity to rent with a 2-week minimum and also use for yourself. This condo has an excellent rental history with bookings in place currently and into high season 2026. Average gross rental income is $20K/year with more upside potential. This delightful 2nd floor, generously sized 1 bedroom condo sustained NO damage from storms and comes fully furnished turn key offering desirable features such as a fully updated & equipped kitchen in on trend design, updated bathroom with new granite top vanity, tub/shower with new high end glass door, tile flooring, fresh bright paint colors, room for guests with convertible sofa, inviting dining space, open floor plan, AC 5 years new, H2O heater 2 years new, well maintained and move in ready! Easy parking with your own assigned space in front of your condo, plus guest parking. The Sea Winds is a small community of 35 units with amenities designed for year-round enjoyment, including bicycle rooms, a social room, shared laundry, pet friendly, and a heated pool complete with lounge chairs, umbrellas, and convenient bathroom facilities. Community pool had a complete upgrade in summer 2025. All buildings had new roofs in 2024 and experienced no major storm damage. The vibrant South Village is nearby, offering a variety of restaurants, boutiques, lively beach bars, ice cream shops, groceries, pharmacies and rental options for everything from fishing and boating to biking and kayaking. Plus, a daily trolley service stops right in front of the Sea Winds Condominium complex, providing easy access to all of Siesta Key's attractions. See this well priced condo today that is ready to go and a great investment on the Key!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Karen Nasello (727-421-0308)
9393 MIDNIGHT PASS RD #P4, SARASOTA, FL 34242
$659,000175 Days on yellowkey MLS ID: A4669033
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1975 Tax: $7,483 (2024)Community: Pointe On Midnight PassCondo
Taxes:$7,483
Remarks: Price Reduction!! ENJOY AWE-INSPIRING SUNRISES AND SUNSETS from this stunning two bedroom, two bath PENTHOUSE condo at the southernmost end of Siesta Key. A corner unit with extra windows, enjoy water views from every room! Wake to breath-taking sunrises over Neville Preserve on Little Sarasota Bay and marvel at spectacular sunsets over the Gulf of Mexico. The largest of units offered at The Pointe, this 10th floor residence is filled with natural light through abundant windows and sliding glass doors. The large kitchen opens to the living room which features beautiful engineered hardwood flooring, crown and base molding, and ceiling beams to separate the dining and living areas. A generous screened and glassed lanai - accessible from both the living room and the primary suite - provides your front-row seat to sunrises, downtown Sarasota, and spectacular wildlife. The private primary retreat offers a large bedroom, a walk-in closet, a built-in vanity with sink, and an ensuite bath with walk-in shower, second sink and toilet. A comfortable guest bedroom and full hall bath complete the main living space. A large laundry room with ample cabinetry, a walk-in utility room off the lanai and a large ground floor assigned lock-off bin provide coveted storage space. An oversized under-building parking space convenient to the building entry completes this unit. Located at the southern tip of Siesta Key, this 5+ acre gated community is beautifully landscaped and features every amenity: heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and canoe racks and launch, a beautiful and fully equipped club house, saunas, fitness centers, an island pavilion with grills, and on-site management and maintenance. A walkway along the water surrounding the property is idyllic for scenic strolls. The Pointe is just minutes' walk to Turtle Beach and three great restaurants. This really is a must see!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
3508 LA PALOMA AVE, SARASOTA, FL 34242
$2,250,00030 Days on yellowkey MLS ID: A4686192
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3195 Built: 2004 Tax: $24,862 (2025)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$24,862
Remarks: Spacious island living awaits in this beautifully maintained 5-bedroom, 3-bath furnished home on the coveted north end of Siesta Key, just steps from beach access No. 1, Shell Rd, on Big Pass and with convenient access to the Sarasota mainland. Fully gated and walled for privacy, the property is surrounded by lush tropical landscaping and offers the ideal blend of comfort, functionality, and a weekly rental. An oversized 3-car garage and large paver driveway provide plenty of space for vehicles, beach gear, and a golf cart—perfect for enjoying the Siesta Key lifestyle. Adding to its appeal, the home is built above base flood elevation, a valuable feature on Siesta Key. Inside, the large open floor plan is designed for entertaining, with 12-foot ceilings, crown molding, arched openings, and travertine flooring. The spacious kitchen features stainless steel appliances, oak cabinetry, and a breakfast nook overlooking the backyard oasis, while a separate dining area and large living room with a gas fireplace provide plenty of space to gather. French doors off the living room open to a large terrace overlooking the backyard oasis, while a second terrace off the side of the home offers a cozy, private spot to relax. The private main-floor primary suite offers direct terrace access, two walk-in closets, an oversized bedroom, and a luxurious en-suite bath with dual vanities, soaking tub, walk-in shower, and floor-to-ceiling travertine. Two additional large bedrooms and a full bath are also located on the first floor. Upstairs, two generous guest bedrooms, a full bath, and a wet bar with a beverage fridge create an ideal retreat for visitors, while one of the bedrooms opens to a private terrace overlooking the backyard. Additional conveniences include multiple storage closets and a central vacuum system for easy maintenance. The backyard is a true tropical oasis with mature landscaping, a heated saltwater pool with fountain, paver deck, large turf area, outdoor shower, and an exceptional tiki hut bar and outdoor kitchen designed for entertaining, complete with a built-in gas grill, two bar fridges, and porcelain countertops. An additional fenced side yard provides a great space for dogs to roam. Ideally located, this property is just moments from world-renowned Siesta Key Beach and a short drive to downtown Sarasota’s celebrated restaurants, shopping, and cultural attractions. With three terraces, abundant indoor-outdoor living, strong weekly rental history, and a prime north Siesta Key location, this is an outstanding opportunity to enjoy the best of island living.
8800 MIDNIGHT PASS RD, SARASOTA, FL 34242
$3,690,00037 Days on yellowkey MLS ID: A4684841
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3676 Built: 2025Monthly Fee: $25 Tax: $8,084 (2025)Community: Tortoise EstatesSpa: YesSingle Family
Taxes:$8,084
Remarks: With gulf views, and walkable private beach access, this New Construction Modern Beach House on Siesta Key mixes a sought-after location with modern luxury. Experience the best of coastal living in this brand-new 4 bed, 4.5 bath home with walking access to Turtle Beach. With 3,676 SF of thoughtfully designed space, this home offers breathtaking 360-degree ocean views, multiple outdoor patios and terraces, and seamless indoor-outdoor flow. Feel the sea breeze in the spacious backyard, including a pool, hot tub, and outdoor kitchen. Enjoy light-toned engineered hardwood floors, a chef’s kitchen with top-tier appliances, and spacious en-suite bedrooms, including a stunning primary suite with a private terrace and spa-like bath. Additional features include a 3-car garage, and 6 covered carport spaces for recreational utility vehicles such as, jet skis, golf carts, or a boat, with easy gate access. Enjoy an elevator included layout, and high-end finishes throughout—all just minutes from Siesta Village’s shops and dining. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Whether for full-time living or a coastal getaway, this is Siesta Key luxury at its finest.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
603 TREMONT ST, SARASOTA, FL 34242
$3,690,00036 Days on yellowkey MLS ID: A4685407
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3996 Built: 2025 Tax: $7,175 (2025)Community: Waterside-Wood Siestas BaysidSingle Family
Taxes:$7,175
Remarks: Perfectly positioned in the heart of Siesta Key, this masterfully crafted New Construction estate epitomizes modern luxury and architectural brilliance. This ultimate entertainment home provides 3,996 square feet of exquisitely designed living space with 4 bedrooms, 4 full bathrooms, 1 half bath, an office, and an upstairs second living room area. From the moment you step inside, you are greeted by a breathtaking open-concept layout accentuated by soaring 20-foot ceilings, floor-to-ceiling glass windows, and sleek porcelain tile flooring, all bathed in natural light and overlooking the lushly landscaped grounds. The state-of-the-art chef’s kitchen is a masterpiece of both style and function, featuring top-of-the-line Monogram appliances, quartz countertops, custom cabinetry, walk-in butlers pantry, and wine display, seamlessly flowing into the luxurious living and dining areas. Designed for an effortless indoor-outdoor lifestyle, this home boasts multiple rooftop decks, two spacious patios, and a resort-style outdoor oasis complete with a fully equipped summer kitchen, built-in grill, pool, and hot tub spa. The primary suite is a private retreat, offering a tranquil terrace, expansive walk-in closet, and a spa-like ensuite with a soaking tub, glass-enclosed shower, and designer finishes. As you ascend the grand staircase to the upper level of the lavish property, you are greeted with a breathtaking sight of three cozy bedrooms, each with its own private ensuite bathroom and featuring private access to a rooftop deck, creating the ultimate serene escape. A second laundry room is conveniently located upstairs to service the secondary bedrooms. Elevating the home’s sophistication, additional highlights include a electric fireplace, custom walk-in closets, high-end quartz cabinetry, and a private elevator for seamless access to every level. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Just moments from world-renowned Siesta Key Beach, fine dining, and premier shopping, this extraordinary residence offers an unparalleled combination of tranquility, elegance, and modern convenience. Your dream coastal retreat awaits—contact us today for a private tour!
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
6263 MIDNIGHT PASS RD #301, SARASOTA, FL 34242
$749,90041 Days on yellowkey MLS ID: TB8486242
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2018 Built: 1981 Tax: $9,637 (2025)Community: Excelsior Beach To Bay 7Spa: YesCondo
Taxes:$9,637
Remarks: Under contract-accepting backup offers. Welcome to coastal living at its finest in the highly sought-after Gulf-to-Bay community of Excelsior Beach to Bay on world-famous Siesta Key. Perfectly positioned in Building One, this 3 bed/3 bath, spacious third-floor residence offers over 2,000 square feet of bright, open living space with partial Gulf views and a unique architectural design rarely found in condominium living. From the moment you enter, soaring vaulted ceilings and an elegant spiral staircase create a dramatic focal point while expansive living and dining areas invite both relaxation and entertaining. Large windows and sliding glass doors lead to a 19x5 enclosed lanai, the perfect spot for morning coffee, reading, or a quiet workspace surrounded by natural light and tropical scenery. The well-appointed kitchen features generous cabinetry, granite countertops, and a convenient pass-through to the living area, allowing seamless interaction with guests and family. The spacious primary suite serves as a private retreat with a large ensuite bath featuring a walk-in shower and soaking tub, while two additional bedrooms and bathrooms provide ideal accommodations for guests, family, or rental flexibility. A new HVAC system offers peace of mind and efficiency, and the residence also includes in-unit washer and dryer, assigned under-building parking, a private storage unit, and additional guest parking. Excelsior Beach to Bay is one of Siesta Key’s most desirable communities, offering a true resort-style lifestyle with private beach access just steps away across Midnight Pass Road, allowing you to walk directly to the powder-soft quartz sand of Siesta Key Beach. Residents enjoy an impressive array of amenities including two heated pools and spas, lively pickleball and tennis courts, a fitness center, fishing pier and bay front dock, library, beautifully maintained tropical grounds, and an active social atmosphere welcoming residents of all ages. With a two-week minimum rental policy, this property presents an outstanding opportunity for full-time residents, seasonal owners, or investors seeking strong rental potential in one of Florida’s most iconic beach destinations, with onsite management available. Owners may have one small pet. Located just minutes from the vibrant Siesta Key Village with its waterfront dining, boutique shopping, and entertainment, this exceptional residence offers the perfect combination of location, lifestyle, and investment opportunity in one of the Gulf Coast’s most coveted communities. Make your appointment today! Life is Short - Buy the Beach House!
Listing Agent: Mindy Smith, Pa (727-599-5534)
116 GARDEN LN, SARASOTA, FL 34242
$1,995,000167 Days on yellowkey MLS ID: A4671064
REDUCED by $155,000 (7.2%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing Agent: Gerard Healy (941-961-2240)
6157 MIDNIGHT PASS RD #E22, SARASOTA, FL 34242
$399,90055 Days on yellowkey MLS ID: A4684348
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 748 Built: 1974 Tax: $3,648 (2025)Community: Bay OaksCondo
Taxes:$3,648
Remarks: BEAUTIFUL 1 BEDROOM 1 BATH UNIT IN BAY OAKS on SIESTA KEY ** TURNKEY FURNISHED ** 1 WEEK RENTALS ALLOWED ** The waves crash, the sand is sugar-coated and the sunsets are striking on Siesta Key.. There is no better location to invest in a 2nd home or investment property. This condo is located on the 2nd floor of building E in Bay Oaks. You will love the large open kitchen and expansive design of this "Santa Fe" themed unit. Located at the end of the 2nd floor in a corner of the building, privacy and tree lined views from the patio create serenity for the owner and tenants. Boasting 750ft2 of living area, there is no wasted space with eat-in dining and wide-open family space. The master bedroom is also open & airy with an on-suite vanity and large walk-in closet, including a washer/dryer. Bay oaks is located just north of the Stickney point bridge allowing more quick escape off the island to Publix, Bealls, Starbucks and Gulf Gate shopping. The community provides a wonderful community pool and tennis court with a full-time manager on site. Beach access 12 is the best public access to the white sands of Siesta Key or catch the Trolley and enjoy and scenic ride to the public beach. Now is the time to invest in Siesta Key real estate.
Listing is courtesy of: SHIRLEY INTERNATIONAL REALTY (941-448-4872)
Listing Agent: Justin Shirley (941-448-4872)
4938 COMMONWEALTH DR, SARASOTA, FL 34242
$2,900,00052 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.
6140 MIDNIGHT PASS RD #A10, SARASOTA, FL 34242
$839,000160 Days on yellowkey MLS ID: A4671897
REDUCED by $10,900 (1.3%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1967 Tax: $7,853 (2024)Community: Horizons WestVilla
Taxes:$7,853
Remarks: Under contract-accepting backup offers. Are you looking for new? Welcome to your fully renovated, turnkey Siesta Key villa, where everything is new from top to bottom! On the Gulf side with direct beach access, this stunning two-bedroom, two-bath coastal retreat has been beautifully transformed into a modern beachside haven. Every detail has been redone with quality and style, such as new kitchen, furnishings and décor, ready for you to move right in and start living your best island life. In the sought-after Horizons West community, this villa offers the ideal blend of comfort and convenience. Enjoy two community pools (one right on the sand and one near your door), along with beach access. Whether you’re seeking a personal getaway or a high-performing investment property, this villa checks every box, and it’s part of a rental program with flexible leasing options and an on-site manager. Experience the ultimate Siesta Key lifestyle, close to Siesta Key Village, where you’ll find vibrant restaurants, boutique shops and nightly entertainment. Or head just minutes away to downtown Sarasota for arts, dining and culture. Own your piece of paradise today, new, beautiful and next to the #1 beach in the world.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
420 BEACH RD #203, SARASOTA, FL 34242
$1,249,000492 Days on yellowkey MLS ID: A4631493
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980 Tax: $10,693 (2025)Community: Siesta Gulf ViewCondo
Taxes:$10,693
Remarks: Paradise Found on Siesta Key! Wake up to Gulf breezes and end each day with a sunset over the water from this direct beachfront condo at Siesta Gulf View. This 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened and glass-enclosed balcony, accessible from the living room, kitchen, and primary suite. From here you can enjoy both the beauty of the shoreline and the natural dune vegetation that makes this second-floor perspective feel close and connected to the beach. This floor level offers an ideal balance of easy access and elevated views: take the stairs for quick trips to the beach, pool, or parking garage, or use the elevator if preferred. No long waits, no hassle, just effortless access to every amenity. The TURNKEY FURNISHED layout includes a light-filled open kitchen with eat-in nook (perfect as a dinette or office), two spacious walk-in closets, separate laundry room, and generous storage throughout. Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping nearing completion, with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Pet lovers will appreciate that up to two small pets are welcome. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate island lifestyle. Don’t miss this opportunity to claim your piece of paradise.
Listing Agent: Jennifer Russo (212-683-1173)
5950 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$599,000169 Days on yellowkey MLS ID: A4670763
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 780 Built: 1957 Tax: $5,444 (2024)Community: Siesta Beach HouseCondo
Taxes:$5,444
Remarks: Gulf-side living at its best! This cute-as-a-button 2-bedroom, 2-bath ground-floor unit has been completely remodeled from top to bottom, featuring new electrical and plumbing, impact windows and doors, stylish new flooring, beautifully updated baths, and a stunning new kitchen with quartz countertops, tile backsplash, countertop breakfast bar, and stainless-steel appliances. The primary bedroom includes an ensuite half bath, while the guest bedroom is conveniently located near the fully remodeled hall bath. Step right out your door and enjoy private beachfront access, a sparkling community pool, and outdoor seating areas with picnic tables. Assigned parking and guest spaces add convenience, while short-term rentals are allowed, offering excellent income potential and bookings already in place should you wish to keep them! Ideally located close to the Village for shops, restaurants, and entertainment, with the free trolley nearby to explore both sides of the Key. This is the perfect coastal retreat and will not disappoint!
Listing Agent: Christine Green (941-914-2463)
1253 N BASIN LN, SARASOTA, FL 34242
$3,295,000190 Days on yellowkey MLS ID: A4668457
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3464 Built: 1971Monthly Fee: $450 Tax: $42,282 (2024)Community: Siesta Properties IncSpa: YesSingle Family
Taxes:$42,282
Remarks: One or more photo(s) has been virtually staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water’s edge. At the heart of the home lies a state-of-the-art culinary haven. The chef’s kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you’ll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Louis Wery (941-232-3001)
1300 N PORTOFINO DR #S206, SARASOTA, FL 34242
$410,00086 Days on yellowkey MLS ID: A4680023
REDUCED by $15,000 (3.5%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1969 Tax: $4,437 (2025)Community: Siesta Harbor IiCondo
Taxes:$4,437
Remarks: Experience the best of waterfront living in this beautifully updated and fully furnished second-floor condo in the highly sought-after Siesta Harbor community. This TURNKEY 2-bedroom, 2-bath residence offers stunning canal and marina views and a prime location just steps from direct beach access across the street through Crescent Arms. Immaculately maintained and move-in ready, the condo features an enclosed lanai with horizontal sliding windows, tasteful furnishings, and thoughtful updates throughout for comfort and relaxation. The spacious open-concept living and dining areas flow seamlessly into a modern kitchen showcasing white cabinetry, quartz countertops, stainless steel appliances, and ample storage. The primary suite includes a walk-in closet and a stand-up shower, while the enclosed lanai provides the perfect spot to enjoy morning coffee or evening cocktails year-round, with dolphins frequently seen playing in the marina. Siesta Harbor is a vibrant 55+ waterfront boating community situated on its own canal and the main waterway of the Intracoastal Waterway. Boat slips may be available for vessels up to 30' (check with the office for availability). Residents enjoy resort-style activities, and amenities including a heated pool, outdoor jacuzzi and shower, indoor sauna, fitness room, shuffleboard court, fishing pier with seating on the ICW, and a beautifully renovated clubhouse with full kitchen, outstanding library, barbecue area with grills, and a full calendar of social activities. Additional highlights include FOB-accessed private beach access, FREE laundry on the 2nd, 3rd, and 4th floors, one designated covered carport parking space, ample guest parking, covered parking, an on-site manager, lush tropical landscaping, and a new roof (2025). Ideally located near the South Bridge, this community offers easy on-and-off access to the Key, is within short distance to restaurants and shops, and has the free Siesta Key trolley stopping right in front of the complex for easy access to Siesta Key Public Beach and Siesta Key Village. Whether you're watching boats drift by on the Intracoastal, crossing the street for unforgettable sunsets, or enjoying the active social lifestyle, this property is perfect as a vacation retreat, full-time residence, or investment opportunity. You deserve paradise!
Listing Agent: David Anthony (941-786-4282)
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