Location: Sarasota , 34242
Do Not Show Listings
5880 MIDNIGHT PASS RD #605, SARASOTA, FL 34242
$1,150,000159 Days on yellowkey MLS ID: A4683118
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $10,494 (2025)Community: CasarinaSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,494
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Imagine awakening each morning to the gentle symphony of waves caressing powder-white sand on Siesta Key, where the Gulf of Mexico stretches endlessly before you in shimmering turquoise splendor. This exquisite two-bedroom, two-bathroom condominium nestled within the prestigious Casarina community offers a lifestyle that transcends ordinary coastal living. Perched elegantly upon seven acres of lush, tropical grounds directly on world-renowned Crescent Beach, this beautifully updated residence delivers the quintessential beach sanctuary you have been dreaming of. Hurricane impact windows provide peace of mind while framing breathtaking beach and gulf views that will steal your breath daily. The thoughtfully renovated kitchen boasts stainless steel appliances, while sophisticated stone-look tile graces the lanai, creating a seamless indoor-outdoor retreat. Beyond your private haven, Casarina's resort-caliber amenities rival the finest destinations. An expansive heated pool and spa with cabana and outdoor kitchen beckons lazy afternoons, while two grilling areas invite convivial gatherings under swaying palms. A sunset beach-side deck transforms evenings into pure magic, and lighted tennis and pickle-ball courts satisfy your competitive spirit. The community thoughtfully provides an on-site management office, fitness room, and generous community center for celebrations and social events. Just moments away, the charming Siesta Key Village offers eclectic dining and boutique shopping, while Phillippi Estate Park provides serene natural escapes. Whether you envision this as your permanent paradise or a cherished seasonal retreat, this freshly repainted gem delivers beach-side living at its absolute finest. Schedule your private showing today and let the Gulf whisper your name.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Dion Souza (941-302-3881)
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,000111 Days on yellowkey MLS ID: A4689015
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,016 (2025)Community: Whispering SandsCondo
Taxes:$5,016
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
4903 COMMONWEALTH DR, SARASOTA, FL 34242
$3,250,000510 Days on yellowkey MLS ID: A4643229
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3146 Built: 2026 Tax: $5,210 (2024)Community: Siesta BeachSpa: NoSingle Family
Taxes:$5,210
Tax Year: 2024
Remarks: Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. This stunning custom residence is now nearing completion, with anticipated delivery in September 2026. Every detail has been thoughtfully curated to deliver an exceptional luxury living experience. This Coastal Contemporary residence offers 3,200 sq. ft. of interior living space and over 5,500 sq. ft. of total indoor/outdoor living, thoughtfully designed to maximize both luxury and comfort. Enjoy three spacious balconies, an outdoor kitchen, and a generous covered lanai that seamlessly blends indoor and outdoor living. Inside, the open floor plan is filled with natural light and features a stunning chef’s kitchen equipped with luxury appliances, custom cabinetry, and a walk-in pantry. The kitchen flows effortlessly into the dining area and great room, creating the perfect space for entertaining or relaxing with family. The home includes 4 bedrooms and 4 full bathrooms, providing ample space for family and guests. The expansive primary suite offers dual walk-in closets, a private balcony, and a serene retreat for homeowners. Upstairs, a versatile loft with access to a private balcony makes an ideal office or second living area. Additional highlights include an oversized 2.5-car garage, elevator access to all levels, and a full utility room for added convenience. The private backyard oasis features a beautiful pool and lush surroundings for year-round enjoyment. Located just minutes from Siesta Key’s world-famous beaches, as well as the vibrant shopping and dining options in The Village, this is a unique opportunity to personalize your dream home during this phase of construction. Don’t miss your chance to own a custom-built home in one of Sarasota’s most sought-after coastal communities. Please note: Some photos have been virtually staged for illustration purposes.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
1500 COVE II PLACE #531, SARASOTA, FL 34242
$549,90049 Days on yellowkey MLS ID: N6144663
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,256 (2025)Community: Midnight Cove IiCondo
Taxes:$5,256
Remarks: Experience the ultimate Siesta Key lifestyle in this turnkey-furnished condominium at Midnight Cove II, ideally situated on beautiful Crescent Beach. Enjoy stunning water and pool views from your private balcony while taking advantage of the community's highly sought after weekly rental program, making this an exceptional investment opportunity, vacation retreat, or personal getaway. The open floor plan creates a bright and inviting living space perfect for relaxing or entertaining. Residents and guests enjoy deeded access to the powdery crystal sands of world famous Siesta Beach, along with resort style amenities including a heated pool, tennis courts, pickleball, fitness center, barbecue area, boat docks, on-site management, and beautifully maintained grounds. Leave the car behind and hop on the trolley to Siesta Key Village or enjoy a short walk to South Village's restaurants, shops, and entertainment. Conveniently located near Sarasota and St. Armands Circle, this property offers the perfect blend of island living and mainland convenience. Whether you're looking for a beachfront escape or a proven income producing property, this is your opportunity to own a piece of paradise on Crescent Beach.
Listing is courtesy of: RE/MAX PALM REALTY OF VENICE (941-451-2025)
Listing Agent: Kimberly Eudy (941-882-2666)
1215 S PORTOFINO DR #406, SARASOTA, FL 34242
$424,90078 Days on yellowkey MLS ID: A4691798
REDUCED by $10,100 (2.3%) on 07/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968 Tax: $4,559 (2025)Community: Siesta Harbor ICondo
Taxes:$4,559
Remarks: Escape the winter chill and step into your endless summer at this meticulously maintained, fully turn-key furnished 2-bedroom, 2-bathroom condo in the desirable Siesta Harbor community on Siesta Key. This 4th-floor gem has been lovingly cared for by the owners and offers charming peek-a-boo ocean views along with direct canal frontage — perfect for morning coffee with a waterfront breeze or romantic sunset dinner. This active 55+ community delivers the true Siesta Key lifestyle with outstanding amenities: deeded beach access via Crescent Arms, a fishing pier on the Intracoastal Waterway, a heated community pool, boat docks, onsite management, and a vibrant calendar of social activities. You’re just minutes from downtown Sarasota’s top restaurants, shops, and cultural attractions.Enjoy low HOA fees, worry-free maintenance, and peace of mind knowing the property has sustained no storm damage. This turn-key condo is your opportunity to own a slice of the laid-back tropical dream on Siesta Key.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Miao Whiteside (941-263-9898)
4646 GLEASON AVE, SARASOTA, FL 34242
$1,350,000202 Days on yellowkey MLS ID: A4677470
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2927 Built: 1957 Tax: $7,816 (2025)Community: Ocean Beach RepSingle Family
Taxes:$7,816
Remarks: Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma, on our famed Siesta Key. Renovated with meticulous attention to detail, this newly updated home features an expansive, light-filled open floor plan with continuous quartzite countertops throughout. It includes two primary suites, one of which flows into its own private kitchenette overlooking the tranquil waterfront. Two lanais and a custom built hot tub and pool complete with a waterfall and color-changing lighting system ensure seamless indoor-outdoor living. Quality and craftsmanship are paramount, and every detail has been thoughtfully considered to ensure superior structural integrity, including the hurricane impact windows and elevated AC condensers. A new roof was installed in 2024, along with new mechanicals, electrical, plumbing, pool surfacing, appliances, and more. This gorgeous island paradise has been fully renovated to both preserve and highlight its architectural elegance. A prime location, this property is ideally situated minutes to the world-famous powdery sands of Siesta Key Beach, less than a mile from charming Siesta Key Village, and near the prestigious Out-of-Door Academy. A quick 5-minute drive over the North Bridge takes you to Sarasota proper and a mere 10 minutes more to the heart of dazzling downtown Sarasota and St. Armands Circle, where you can enjoy a wide selection of fine dining, shopping, and world-class cultural arts and nightlife, making it the ideal home for those seeking the ultimate Florida lifestyle. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Victor Maravi Passara (941-284-3356)
5322 CALLE DE LA SIESTA, SARASOTA, FL 34242
$4,400,000167 Days on yellowkey MLS ID: A4682172
REDUCED by $500,000 (10.2%) on 07/27/2026
Bed: 9 Bath: 0.0 Liv Area Sq Ft: 4437 Built: 1999 Tax: $22,056 (2025)Community: Sarasota BeachSpa: YesApartment
Taxes:$22,056
Remarks: 5.9% Seller Financing and Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your guests will enjoy a great pool area, sizable covered space with a grill, on site laundry, and a roof top deck. It's 1 block to both the Village and beach, guests walk everywhere. Park your car in one of the 7 newly pavered spaces and don't start it again until the vacation is over. Now for you the owner, a private office/guest check in, 2 storage areas for linens housewares etc, and a commercial laundry for turnovers. These types never trade, don't let another 20 years pass before this sells again. Cap rate and NOI is proforma
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Jason Skowronski (941-812-6090)
119 WHISPERING SANDS CIR #V36, SARASOTA, FL 34242
$495,000341 Days on yellowkey MLS ID: A4656278
REDUCED by $30,000 (5.7%) on 06/14/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1160 Built: 1968Monthly Fee: $1,351 Tax: $6,617 (2024)Community: Whispering SandsCondo
Taxes:$6,617
Remarks: One or more photo(s) has been virtually staged. BEST PRICED UPDATED VILLA WITH GARAGE ON SIESTA KEY! Don't miss this opportunity to own this lovely REMODELED VILLA just steps from the sand! This 2 bed/2 bath villa nestled in the premier GULF FRONT property of Whispering Sands is the perfect island getaway. Remodeled in 2025, this villa features all NEW vinyl plank flooring, paint, baseboards, trim, molding, and all interior doors. The bright NEW galley kitchen is a true highlight, offering stylish soft close cabinetry, granite countertops, stainless Whirlpool appliances, a side by side fridge with icemaker/dispenser, stainless farmhouse sink, and recessed and under-cabinet lighting. Both bathrooms have been refreshed with new granite counters, cabinets, vanities, and fixtures for a clean, contemporary feel. You’ll enjoy the ease of indoor-outdoor living with a tiled screened lanai – perfect for your morning coffee or evening relaxation. It could be further enclosed with windows or sliders and turned into a sunroom. This villa also features a nice skip trowel ceiling finish and plantation shutters. One car garage with NEW 2026 epoxy floor. NEW 2025 full sized Maytag WASHER & DRYER. NEW 2025 VILLA ROOF. 2025 HVAC system and 2025 water heater. Ideally located just around the corner from Whispering Sands’ two sparkling heated pools, clubhouse (currently in the beginning stages of being remodeled and which will include a fitness center and catering kitchen), NEW beachside Tiki Hut, shuffleboard, and 800' of your own private beach on the Gulf — perfect for enjoying Siesta Key’s world famous quartz sand and spectacular sunsets! When you're not luxuriating in the pool or going for a dip in the Gulf, step out of your front door and walk to shopping and dinner! Whispering Sands is situated right around the corner from the colorful boutiques and fine restaurants of Siesta Key Village. Embrace the island lifestyle! Whether as a year-round residence or a vacation retreat, this maintenance free Gulfside villa combines ease, style, comfort - and a great investment - in one of Siesta Key’s finest Gulf front properties.
611 VENICE LN, SARASOTA, FL 34242
$999,00098 Days on yellowkey MLS ID: A4686684
REDUCED by $51,000 (4.9%) on 07/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2168 Built: 1972 Tax: $9,119 (2025)Community: Siestas Bayside Waterside EastSpa: NoSingle Family
Taxes:$9,119
Remarks: Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, approximately 2,168 square feet of living space and a 2-car garage, there is room for full-time living, a vacation getaway, or a high-demand rental. Built of concrete block, this Ruth Richmond home offers peace of mind with major updates already done: brand new metal roof with warranty (April 2026), AC with warranty (August 2023), garage door (March 2025), front door (April 2025), and low-maintenance terrazzo flooring. Step inside to an inviting, well-planned layout with the primary suite on one side of the home with updated ensuite bath, and guest bedrooms on the other, offering privacy for family and visitors. The newly updated kitchen features granite countertops and modern finishes. The living room, dining area, and sunroom flow together seamlessly and overlook your private backyard oasis. Outside, enjoy your own sparkling, “sports pool” with a shallow area across the center, ideal for hosting friends for a game of pool volleyball, playing with the kiddos, or lounging. A brand-new fence with self-closing gates (April 2025) wraps the yard in privacy, creating a quiet retreat after a day at the beach. Located on world-famous Siesta Key you’re just minutes from the white quartz sand beaches, charming village shops and restaurants, boating, kayaking, and all the island lifestyle has to offer. This home combines an incredible coastal location with everyday convenience. Turn the key, drop your bags, and start living the Siesta Key lifestyle at 611 Venice Lane.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
1350 N PORTOFINO DR #107, SARASOTA, FL 34242
$334,900340 Days on yellowkey MLS ID: A4662545
REDUCED by $39,000 (10.4%) on 07/23/2026
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1969 Tax: $2,300 (2024)Community: Siesta Harbor IiSpa: NoCondo
Taxes:$2,300
Remarks: Welcome to Siesta Harbor, a highly desirable 55+ waterfront community on world-famous Siesta Key, where spectacular canal and Intracoastal Waterway views create the perfect backdrop for relaxed coastal living. Located directly across the street from deeded beach access, you'll enjoy the best of both worlds—boating from your backyard and one of America's top-rated beaches just steps away. This beautifully renovated one-bedroom, two-full-bath residence has been thoughtfully redesigned from top to bottom with exceptional attention to detail. Features include impact windows throughout, a stunning contemporary kitchen with floating cabinetry, quartz countertops, new stainless appliances, designer lighting, updated bathrooms with floating vanities, illuminated mirrors, a beautifully remodeled shower, new hot water heater, updated electrical outlets and switches, new interior doors, hardware and baseboards, smooth textured ceilings with the popcorn removed, and an HVAC system that's approximately two years old. The intelligently designed floor plan offers an abundance of storage rarely found in a one-bedroom condominium, including two bedroom closets with a walk-in closet, linen closet, hallway coat closet, pantry, and a private exterior storage room perfect for bicycles, beach chairs, fishing gear, and other coastal essentials. Boaters will appreciate the opportunity to dock a vessel up to 30 feet for approximately $1,000 annually (subject to availability and community guidelines), making it easy to explore Sarasota Bay and the Intracoastal Waterway right from home. Residents enjoy an outstanding collection of amenities including a heated waterfront pool, fishing and boat-watching pier, tandem boat docks, fitness center, recreation clubhouse, shuffleboard courts, outdoor grilling area, beautifully maintained grounds, and complimentary laundry facilities conveniently located on multiple floors. Exclusive FOB beach access through Crescent Arms makes trips to the powdery white sands of Siesta Beach effortless. The property also includes a covered carport parking space (#537) along with ample guest parking. Siesta Harbor is rental-friendly and welcomes service animals in accordance with applicable regulations. Offered at just $334,900—below competing renovated waterfront properties—this exceptional residence presents an outstanding opportunity to own a move-in-ready waterfront condominium with beach access, boating, and the incomparable Siesta Key lifestyle.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
4034 ROBERTS POINT RD, SARASOTA, FL 34242
$8,500,00039 Days on yellowkey MLS ID: A4697653
Bed: 5 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 5095 Built: 1990 Tax: $52,899 (2025)Community: Elliot M Prop Siesta KeySpa: YesSingle Family
Taxes:$52,899
Remarks: A rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
8800 MIDNIGHT PASS RD, SARASOTA, FL 34242
$3,690,00044 Days on yellowkey MLS ID: A4697104
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 sunset 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 ocean views throughout, multiple outdoor patios and terraces, rooftop deck, 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)
7345 PINE NEEDLE RD, SARASOTA, FL 34242
$2,350,00092 Days on yellowkey MLS ID: A4690626
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2977 Built: 1956Monthly Fee: $450 Tax: $10,699 (2025)Community: Sanderling ClubSingle Family
Taxes:$10,699
Remarks: Beautifully renovated 4-bedroom, 4-bath pool home tucked behind the gates of the exclusive Sanderling Club. Surrounded by a grandfathered privacy wall and lush tropical foliage, the property is just steps from your own private beach. 2023 updates include - new roof, hurricane-impact windows/sliders and plumbing. Meticulously renovated in 2025–2026 with top-of-the-line finishes throughout the entire home. Luxury vinyl plank flooring flows through the open floor plan, complemented by granite countertops and a oversized granite island with lots of storage, Samsung appliances and an open-concept layout ideal for entertaining, with abundant indoor/outdoor living space with views of the oversized sparkling pool. The primary suite is a tranquil retreat with two walk-in closets and an en-suite bath featuring a double vanity and soaking tub. A thoughtful split plan offers two additional spacious bedrooms each with en-suite baths. A fully renovated pool house/mother-in-law suite with its own full bath adds flexible living options. Located in a waterfront community, residents of the Sanderling Club have exclusive beachfront access, tennis and pickleball courts, clubhouse and 24-hour security This home blends refined luxury with coastal lifestyle and privacy.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Amy Nadell (941-539-5424)
5740 MIDNIGHT PASS RD #104F, SARASOTA, FL 34242
$1,375,000186 Days on yellowkey MLS ID: A4679012
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $9,698 (2025)Community: Gulf & Bay Club Ph6Spa: YesCondo
Taxes:$9,698
Remarks: Incredible Gulf-front first-floor residence (10’ elevation) within the amenity-rich 32-acre campus of the Gulf & Bay community on Siesta Key. This 2-bedroom, 2-bath furnished condominium is ideally positioned in the highly desirable F Building and offers direct walk-out access to the beach with unobstructed views of 800 feet of private shoreline and the expansive Gulf of Mexico. Just steps from the sand, this exceptional location delivers the ultimate Gulf & Bay lifestyle—blending convenience, privacy, and breathtaking coastal scenery. This unit did not flood during recent storms. The remodeled kitchen features abundant cabinetry, a beverage cooler, and a comfortable eat-in area with a built-in desk. The primary suite captures beautiful Gulf views and includes a walk-in closet plus an additional wall closet. The en-suite bath has been tastefully remodeled with a frameless travertine shower, dual vanities, and a dedicated makeup area. The spacious guest bedroom offers two full Murphy beds, providing flexible sleeping accommodations. Additional highlights include a new A/C system (2025), 20" x 20" tile throughout the main living areas, and smooth ceilings—no popcorn. Gulf & Bay is truly one of the best resort complexes on Siesta key featuring: 2 clubhouses, 3 heated pools, pickleball courts, tennis courts (1 HarTru), well equipped fitness center, hot tub, multiple grill areas all leading out to World Famous, gorgeous Siesta Key Beach!
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
4660 OCEAN BLVD #Q2, SARASOTA, FL 34242
$624,90089 Days on yellowkey MLS ID: A4692194
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $6,131 (2025)Community: Sea VillageSpa: NoCondo
Taxes:$6,131
Remarks: BEST PRICED GULF-FRONT CONDO ON SIESTA KEY, in terms of VIEW, CONDITION, SIZE, AMENITIES and PROXIMITY to Siesta Key Village, the #1 BEACH IN America, and DOWNTOWN SARASOTA! Not ONE, but TWO heated GULF FRONT POOLS. Brand NEW fishing dock. This lovely unit can come partially furnished if you wish (a full list of items is available) and has a BRAND-NEW A/C. MOVE IN READY! Unobstructed GULF VIEWS, forever YOURS! And it’s PET FRIENDLY! HOA covers just about everything! Bring your suitcase, your toothbrush and your bathing suit! Wake up to breathtaking Gulf views, watch as dolphins swim, and enjoy legendary Siesta Key sunsets from this beautifully maintained 2-bed, 2-bath, perfectly positioned condo in a charming Gulf front community. Floor-to-ceiling glass sliders flood the open living area and primary bedroom with natural light, leading to your private screened lanai, where uninterrupted Gulf views are yours to behold. The primary bedroom features ample closet space and an ensuite bath with separate vanity. With 1,200 ft² of living space, this second-floor residence comes with an in-unit washer/dryer, as well as a free community laundry room and storage. The second bedroom is perfect for guests and family, and the well-appointed kitchen has upgraded appliances and a pass-through to the living area. This exceptional unit has had just one owner and has been in the family since the complex was built. Sea Village is a small community located exactly 1 mile north of Siesta Key Village and 1 mile to the #1 Beach in America. Amenities include two heated gulf front pools, a newly constructed fishing pier, and designated covered parking. ALL assessments have been PAID. Monthly HOA covers Community Pool, Escrow Reserves, Insurance, Exterior Maintenance (to include the roof), Maintenance of the Grounds, as well as Water, Sewer and Trash. Renowned for its vibrant coastal lifestyle, Siesta Key Village is bustling with restaurants, cafes, shops and miles of crystalline beaches. Downtown Sarasota’s Bayfront, with its world-class shopping, dining, & cultural events is 5 miles away. Nature lovers, sports enthusiasts, and patrons of the arts have the best of Sarasota at their fingertips with outdoor activities that include waterfront dining, boating, biking, golfing, hiking & fishing nearby. With easy access to state-of-the-art medical facilities, Sarasota International Airport, and the I-75, the location of this property offers the perfect blend of serenity & convenience and offers an extraordinary opportunity to LIVE YOUR BEST LIFE, whether it be used as a private retreat for your own personal enjoyment, or a seasonal or annual rental, with excellent income potential.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Robin Leonardi (941-685-6270)
1257 S PORTOFINO DR #104, SARASOTA, FL 34242
$449,90073 Days on yellowkey MLS ID: A4692335
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1968Monthly Fee: $957 Tax: $3,326 (2025)Community: Siesta Harbor ICondo
Taxes:$3,326
Remarks: Bring your boat and dock steps from your back door.. Turnkey living in Siesta Harbor, a 55+ waterfront community, with beautiful canal water views and private beach access. This fully renovated 1-bedroom, 2-bath condo offers an open floor plan, updated kitchen and bathrooms, newer impact sliding doors, and a newer HVAC system (2021). Enjoy peaceful water views from the enclosed lanai as boats pass by. Boat slips are available for vessels up to 30’, with dockage approximately $1,000 annually (buyer to verify with Harbor Master). This property is also investment-friendly, allowing monthly rentals, and has a strong rental history (buyer to verify current rental restrictions and income). Community amenities include a heated waterfront pool, fishing pier, fitness center, clubhouse, shuffleboard, and busy social calendar. Additional features include assigned covered parking and private storage. Located just steps to beach access through Crescent Arms and close to dining, shopping, and the Siesta Key trolley. Ideal as a full-time residence, seasonal retreat, or income-producing property.
Listing Agent: Suzy Kolaz (941-726-1153)
558 VENICE LN, SARASOTA, FL 34242
$4,485,000110 Days on yellowkey MLS ID: A4689132
REDUCED by $164,900 (3.5%) on 06/16/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4132 Built: 2025Monthly Fee: $33 Tax: $4,509 (2025)Community: Siestas Bayside Waterside EastSpa: YesSingle Family
Taxes:$4,509
High School: Riverview High
Remarks: Newly completed and move-in ready, this Coastal Contemporary waterfront residence on Siesta Key by award-winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft, and elevator—perfectly blending luxury, functionality, and coastal living. The main level features white oak wood floors, soaring beamed ceilings, and a bright open-concept layout designed for both everyday living and entertaining. The gourmet kitchen and expansive great room flow seamlessly through 10’ impact-resistant sliding glass doors to the outdoor living area, showcasing tranquil views of the pool and Grand Canal. A dedicated private office, a luxurious primary suite with a spa-inspired bath, and an additional ensuite guest bedroom complete the first floor. Upstairs, a spacious loft provides an ideal secondary gathering space. The VIP suite features a private balcony overlooking the water, while the fifth bedroom offers flexibility as a media room, fitness studio, or guest retreat. A custom wet bar enhances the upper level, creating the perfect setting for entertaining. Set along the scenic canals of Siesta Key, this property offers exceptional boating opportunities with easy access to open water—ideal for enjoying the best of Florida’s waterfront lifestyle right from your backyard. The outdoor living space is designed as a private retreat, complete with a sparkling pool, spa, and peaceful water views. Quick out to the expensive Intracoastal waterways for boaters. Florida living at its finest — sunset views, alfresco dining, and cozy evenings by the outdoor fireplace. A beautiful patio and grill setup that feels like a dream come true. Located just minutes from Siesta Key Beach, this home provides quick access to world-renowned beaches, dining, and the vibrant coastal lifestyle that makes Siesta Key one of the most desirable destinations in Florida. Exceptional opportunity to own a brand-new waterfront home with boating access in one of Sarasota’s premier locations.
Listing Agent: Andrew Haddad (941-313-1218)
101 WHISPERING SANDS DR #105, SARASOTA, FL 34242
$679,000130 Days on yellowkey MLS ID: A4686924
REDUCED by $20,000 (2.9%) on 06/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $4,088 (2025)Community: Whispering Sands Sec 3Condo
Taxes:$4,088
Remarks: INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opportunity for TURNKEY FURNISHED Residence with FULL WATER VIEWS throughout all Living Areas!..... Located in the Whispering Sands Community you will be able to WALK to the adjacent Village as well as ENJOY over 800' of PRIVATE deeded "white baby powder quartz sands" Beach Access; (2) Heated Pools; clubhouse, fitness center; beachside tiki and so much more in a true "residential neighborhood" setting. Bright & Spacious Open Floor Plan; Updated Kitchen and Baths with Quartz Countertops & Backsplashes; HURRICANE IMPACT SLIDERS open into an Expansive Lanai with Multiple Living Spaces---Perfect for listening to your favorite podcast or Enjoying Majestic Sunsets with Evening Cocktails----The Ultimate in the Siesta Key Lifestyle!
Listing Agent: Mike Martino (773-619-8593)
5880 MIDNIGHT PASS RD #907, SARASOTA, FL 34242
$1,850,00063 Days on yellowkey MLS ID: A4694262
Bed: 3 Bath: 2.0 Gar: 25 Liv Area Sq Ft: 2165 Built: 1982 Tax: $16,144 (2025)Community: CasarinaCondo
Taxes:$16,144
Remarks: TOP FLOOR. TOP BEACH. TOP NOTCH. This Siesta Key condo checks ALL the hard to find boxes — THREE bedrooms. PRIVATE Beach. TOP Floor. RESORT Style Amenities. GARAGE Parking Space. NO Work Needed! Welcome to Unit 907, a beautifully refreshed top-floor residence offering generous living space, a calm coastal feel, and the easy beach lifestyle buyers are looking for. From the moment you open the door, the residence feels bright, relaxed, and beautifully pulled together with updated coastal furnishings and a soft beachside palette. Spacious living and dining areas create an easy flow for everyday enjoyment or extended stays, while the kitchen offers quartz countertops, stainless appliances, breakfast bar, and generous storage. The Master Bedroom has spectacular gulf views, ensuite with double sinks, walk-in shower, and a spacious closet. The split-bedroom floor plan with two guest bedrooms provides privacy and flexibility for guests, or home office, hobbies, and additional storage. The Casarina community has recently completed significant improvements which include a new roof, elevator updates, electrical updates, new A/C units, flood-prevention panels, new carport roofs, refreshed landscaping, new driveway and pool pavers, new grilling area, and more — assessments already paid by seller! Get ready to enjoy approximately 7 acres of tropical grounds, direct access to Siesta Key's powdery-soft, white sand beach, heated pool and spa, clubhouse, fitness room, tennis and pickleball courts, basketball, BBQ areas, onsite management, secured access, two elevators, and beautifully maintained outdoor spaces. Minutes from Siesta Key Village, dining, shopping, and downtown Sarasota. Contact me today to schedule your private tour and start living the Siesta Key lifestyle you've always dreamed of.
Listing Agent: Christa Spalding (941-529-6978)
1224 MOONMIST CIR #S-3, SARASOTA, FL 34242
$749,00092 Days on yellowkey MLS ID: A4690713
REDUCED by $40,900 (5.2%) on 05/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1949 Built: 1968 Tax: $4,925 (2025)Community: Polynesian GardensSpa: NoCondo
Taxes:$4,925
Remarks: Outstanding remodeled and updated freestanding 3/3 villa in private and beautiful Polynesian Gardens. New ceramic tile flooring throughout. Spacious with large rooms plus 259 extra square feet in glassed in lanai/Florida room which can be used as a family room. office or man cave. The updates include a new addition to the villa of approximately 330 additional square feet and a beautiful second primary suite/third bedroom with an ensuite bath and a laundry room with new washer/dryer and cabinet and closets. 3 bedrooms are split from each other. Primary bedroom has an ensuite bath with a shower and extra shelving for toiletries, large walk-in closet and a set of sliders to the Florida room. Guest bedroom is large enough for two queen size beds plus large closets. Guest bathroom is right outside of guest bedroom and has a tub/shower with updated vanity with dual sinks. Combo living/dining area with easy access to updated kitchen with pantry and cabinetry galore. New appliances. Living/dining room is large and has a coat closet. New sliding glass door adds sunshine and light and leads to the large private paved side yard and back yard. Large enough for gardening, patio furniture and a barbeque. This villa has been replumbed and the drainpipes were replaced in the entire house in 2017. The roof was replaced by the Association in 2020. New roof on the addition and transition to the existing roof in 2026 Exterior has been freshly painted. New landscaping. Installation of a new 5' high white vinyl fence in the front and rear with a gated storage space. Solar security lights on the rear fence. Many more improvements too numerous to list but available on a feature sheet. Polynesian Gardens is an active community with a clubhouse, heated swimming pool and a newly built fishing pier. Yet the location and setting of Polynesian Gardens allows its owners to enjoy a relaxed coastal lifestyle. The Siesta Breeze free trolley stops in front of the community and will take you to Siesta Village for shopping and eating out, to Turtle Beach and to world renowned Siesta Key beach, America's #1 Beach, known for its powdery white quartz sand. Close to Sarasota's downtown area and cultural centers, there are many venues for entertainment and education. Rentals are allowed and are always in demand. Own your own piece of Paradise.
Listing Agent: Stephen Clementi (912-704-2116)
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