Location: Sarasota , 34242
Do Not Show Listings
1215 S PORTOFINO DR #308, SARASOTA, FL 34242
$525,00032 Days on yellowkey MLS ID: A4686879
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1230 Built: 1968Community: Siesta Harbor ICondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: HUGE PRICE REDUCTION!!! LOWEST PRICE 2 BEDROOM 2 BATH CORNER UNIT AVAILABLE!! THIS IS YOUR OPPORTUNITY FULLY FURNISHED, BEAUTIFULLY DONE, VIEWS OF THE CANAL EVERYWHERE!, BEACH ACCESS, PLUS BOAT, DOCK ON THE MAIN INTRACOASTAL WATERWAY, WALK TO SHOPS, RESTAURANTS, EASY ON AND OFF THE KEY, JUST MOVE IN AND ENJOY YOUR LIFE! HURRICANE IMPACT WINDOWS, ENCLOSED LANAI, THIS ONE HAS IT ALL!! Dont miss this one!
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Judith Guzzi (914-490-9032)
1269 DOCKSIDE PL #115, SARASOTA, FL 34242
$825,000204 Days on yellowkey MLS ID: A4656792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1217 Built: 1982Community: Harbour TowneCondo
Remarks: This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the dock. Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo features tile flooring throughout with both HVAC and appliances that are only a couple of years old. The roof was replaced in November 2021, and the unit has a one-car garage with storage above as well as a dedicated parking space in front. In addition, this unit has one of the few private outdoor decks in the community. Harbour Towne offers fantastic amenities, including a clubhouse, heated pool, spa, and tennis/pickleball courts. Enjoy the village by day or evening for great dining, shopping and live music. A complimentary trolley runs by the complex on a regular schedule in season. This is a great place to live and play! Look no further, this is where your fun-filled life begins.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
5309 HIDDEN HARBOR RD, SARASOTA, FL 34242
$4,500,000187 Days on yellowkey MLS ID: A4668550
Bed: 6 Bath: 6.0 Liv Area Sq Ft: 6655 Built: 2007Community: Hidden HarborSingle Family
Remarks: Majestic waterfront home nestled in one of Siesta Key's most exclusive neighborhoods. Prime waterfront location with direct access to the inter-coastal (no bridges) and features a 16,000 pound vertical lift and a jet ski lift. This Waterfront home features wraparound decks on multiple levels composed of Brazilian Ipe decking, wood ceilings, a private grill area with a dramatic view up the canal and a resort like swimming pool and spa featuring a rock waterfall and paver patio to fill your sun filled afternoons. Upon entering the home, you will see the amount of detail and craftsmanship that was put into this home. Hand-scraped wood flooring, coffered tongue-n-groove ceilings, huge baseboard and crown molding throughout. Expansive windows let the natural light in and an aquarium glass wall in the kitchen/family room overlooks your lower deck, swimming pool, spa and water view. The home has well over 6000 square feet of living area with the master suite occupying the first-floor level. This home affords 6 bedrooms, 5 full baths, 2 half baths, a private office with built-in cabinetry, 2 wet bars one on each level, 2 laundries with one on each level, a Sports room/ man cave with a built-in entertainment center. Upstairs has 4 bedrooms, two of which are suites, a second family room/playroom, theater/entertainment room which connects to your second level deck. The main level of the home incorporates your kitchen, family room, pantry, wet bar, dining room, private office, master suite and laundry. The kitchen features a huge walk-in pantry with entry door, a huge center island with a granite top, Subzero refrigerator, a Wolf 6 burner/griddle stove, a Wolf warming drawer, a Wolf microwave, 2 drawer Fisher Paykel dishwasher and a second Miele dishwasher for all your entertainment needs. Each level has a wet bar with the lower level having a subzero wine refrigerator and a drink refrigerator and the upstairs level has a Fisher Paykel dishwasher, an ice-maker, microwave, and a refrigerator. For the car enthusiast you have two 2 car garages with separate drives which provides additional parking as well. This spectacular home is hard to match, and you won't be disappointed. The home has an elevation of 15 feet and also has a home generator to provide comfort and a sense of security during any power outages that may occur. Schedule an appointment to see your future home!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Livesey (941-346-7454)
4117 ROBERTS POINT CIR, SARASOTA, FL 34242
$980,000420 Days on yellowkey MLS ID: A4640938
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2168 Built: 1990Community: Roberts Point 2Single Family
Remarks: Nestled on a tranquil street, in the highly sought-after Roberts Point neighborhood of Siesta Key, this stunning elevated home offers the perfect blend of luxury, privacy, and coastal charm. Situated just moments from the world-renowned Siesta Beach and the vibrant Siesta Village, this beautifully maintained two-story residence offers the perfect combination of comfort, convenience, and Florida living. The layout features spacious living and dining areas, with plantation shutter windows that fill the home with natural light and allow for a seamless connection to the outdoors. The well-appointed kitchen includes modern appliances, ample cabinetry, and a large island, making it an ideal space for cooking and entertaining. The master suite is a private retreat, with plenty of closet space and an en-suite bathroom that offers a relaxing atmosphere. Additional bedrooms are generously sized and perfect for family or guests. Step outside to your private, nicely landscaped backyard, an ideal setting for relaxation and entertaining. Enjoy Florida’s beautiful weather on the expansive composite deck, complete with an outdoor shower—perfect for rinsing off after a day at the beach. The lush greenery and well-maintained yard create a tranquil, private oasis. This home’s prime location offers easy access to the best of Siesta Key—whether it's lounging on the soft sands of Siesta Beach, exploring the unique shops and restaurants in Siesta Village, or enjoying local parks and recreational activities. This is your chance to own a slice of paradise in one of the most coveted neighborhoods on Siesta Key. Schedule your private showing today and make this beautiful home your own!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Jim Mast (941-587-9066)
6512 MIDNIGHT PASS RD #303, SARASOTA, FL 34242
$2,190,000344 Days on yellowkey MLS ID: A4652317
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1763 Built: 2006Community: Crescent Siesta KeyCondo
Remarks: Welcome to luxurious, maintenance-free beachfront living at prestigious Crescent Siesta Key Condominiums. This 1,800-square-foot turnkey-furnished unit offers three bedrooms, two full baths, a laundry room and two large balconies, one with beach views, and the other overlooking the second-level Crescent pool/courtyard. The inviting open floor plan includes a large dining room. The kitchen is open to the dining room and living room. Poggenpohl (luxury German-made) cabinets, stainless appliances, large breakfast bar and spacious pantry/storage cabinets line the hallway. It is near south Siesta Key Bridge with shopping, entertainment and dining across the street. The Crescent is a boutique complex of only 26 units and offers direct beach access, a gulf-view pool with whirlpool hot tub, as well as a single-lane lap pool, a gourmet poolside summer kitchen and a beautifully landscaped garden terrace with poolside seating. It includes well-appointed common areas, elevators to all floors, a clubhouse, a fitness room, reserved two-car covered parking, a car charging station, on-site manager and 24-hour video surveillance with common areas secured by keypad access. It is a pet-friendly community for owners only. Investors alert! The unit is on the vacation rental program with Beachside Management, and it attracts lots of bookings. This is must-see.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Ziad Sleit (941-928-5493)
101 WHISPERING SANDS DR #107, SARASOTA, FL 34242
$495,000139 Days on yellowkey MLS ID: A4674069
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Community: Whispering SandsCondo
Remarks: One or more photo(s) has been virtually staged. Affordable GULF FRONT living! This is the BEST PRICED CONDO in Whispering Sands. Welcome to this recently updated 2 bed/2 bath, DOUBLE LANAI CORNER unit nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of private beach. The freshly painted interior features NEW luxury vinyl plank flooring, interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and new ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE beach. The clubhouse is currently undergoing complete remodeling. Upon completion in early 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
145 AVENIDA MESSINA #3, SARASOTA, FL 34242
$630,000201 Days on yellowkey MLS ID: A4667146
2 Days Off yellowkey (back on 3/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1025 Built: 1966Community: Villa NavarraCondo
Remarks: Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic tile flooring throughout. The guest bath was completely remodeled along with the primary bathroom that has been expanded for a little extra elbow room. This has a new water heater and HVAC system, new roof in 2025, all new doors, impact windows, ceiling texture and it doesn't stop there. This comes very tastefully turnkey furnished in a warm coastal theme! Relax on your screened patio and look out to palms and foliage and take in the gulf breezes. The pristine beach is 2/10 of a mile away and the SK Village is about 100 feet away with a large selection of restaurants, shopping, grocery, nightlife, and so much more! Don't miss this beautiful condo in the heart of all that Siesta Key has to offer in a very well-run complex.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
1200 EAST PEPPERTREE LANE #302, SARASOTA, FL 34242
$729,00042 Days on yellowkey MLS ID: A4685295
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1463 Built: 1975Community: Peppertree BayCondo
Remarks: PRICE IMPROVEMENT OF $20.000!! Turnkey coastal living in the desirable mid-rise tower at Peppertree Bay on Siesta Key. This sought-after split-plan residence offers bright open living spaces, exceptional privacy, and the convenience of effortless island living with resort-style Gulf-to-Bay amenities just moments from world-famous Siesta Beach. Offered fully turnkey furnished, this beautifully maintained two-bedroom, two-bath residence is ready for immediate enjoyment as a primary residence, seasonal retreat, or investment property. The split-bedroom layout provides privacy for owners and guests, while the open living and dining areas create a comfortable space for everyday living and entertaining. A feature seldom found in these units is the dedicated laundry room with a utility sink, adding both convenience and functionality. The residence also includes elevator access, covered parking, and generous storage. Peppertree Bay is one of Siesta Key’s most sought-after Gulf-to-Bay communities, offering private beach access to the powdery quartz sands of Siesta Beach, two heated pools, tennis and pickleball courts, a fitness center, clubhouse, fishing pier, and beautifully maintained tropical grounds. Ideally located just minutes from Siesta Village dining, shopping, and entertainment, this residence offers the best of relaxed island living.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Renee Nadiv (941-299-4242)
5770 MIDNIGHT PASS RD #C601, SARASOTA, FL 34242
$1,395,000139 Days on yellowkey MLS ID: A4674063
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1337 Built: 1980Community: Gulf & Bay Club Ph 3Condo
Remarks: An exquisite, fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high end detailed finishes and interiors professionally crafted to perfection. This unit is in C Building with direct beach access just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and on site car wash. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Sylvia Wilk (630-863-1825)
8779 MIDNIGHT PASS RD #502H, SARASOTA, FL 34242
$735,000130 Days on yellowkey MLS ID: A4673776
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1303 Built: 1980Community: Island Reef Ii Ph 1 2 & 3Condo
Remarks: A rare top floor opportunity in a quiet corner of Island Reef. Stunning views of Little Sarasota Bay and the Gulf from the always-shaded lanai or balcony where sunrises and sunsets are easily visible this time of year. Renovated from top to bottom, this is one of the few units with "Impact Glass" already installed in the lanai. This is a true turn-key opportunity allows you to move in immediately and start enjoying this little corner of paradise. Kitchen features granite countertops, and the unit includes an in-residence laundry. Furnished and complete with a carport! Island Reef is a serene waterfront community, and one of the few Gulf-to-Bay communities that offers many desirable amenities including a beach, boat docks (lifts allowed), two lit tennis courts, pickleball, two fitness rooms, kayak storage, a library, billiards, a game room, a clubhouse, two heated pools and gas grills. Pet friendly! Tropical gardens enhance the appeal of Island Reef and this wonderful community, conveniently located near two of Siesta Key's popular restaurants. A complimentary trolley provides access to Siesta beach, Siesta Village offering dining, shopping, ice cream, mini donuts, cute brunch spots, dancing, and live music every night of the week.
Listing Agent: Marlene Marshall (941-539-8850)
8779 MIDNIGHT PASS RD #106H, SARASOTA, FL 34242
$595,000399 Days on yellowkey MLS ID: A4644937
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1768 Built: 1980Community: Island Reef Ii Ph 1 2 & 3Condo
Remarks: This residence is being sold furnished (some items excluded). Open floor plan. (2070 Sq feet; builders floor plan), two spacious bedrooms, 2 ½ baths, office space, laundry, and large enclosed Lanai. Upgrades include new flooring, new washer and dryer, new hot water heater and new air conditioner. Enjoy picturesque Bay views to watch the sunrise and across the street you can watch sunsets on the Gulf of Mexico. This larger floor plan has full Bay views. Back Door exit gives you easy access tp BBQ area and Boat Dock. First floor allows seamless entry to the residence. Residents of Island Reef enjoy boat docks (lifts allowed), beach, two heated pools, tennis, pickleball, two fitness rooms, saunas, shuffleboard courts, billiards, library, clubhouse, social room, gas grills, bicycle and kayak storage. The carport is just a few steps from the front door. Guest Parking. Close to two of Siesta Key’s popular restaurants. Free trolley to Siesta Village. Monthly rentals (8 leases a year), pet friendly (30 lbs.), on-site management and rental program.
SARASOTA, FL 34242
$480,00094 Days on yellowkey MLS ID: A4678719
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1975Community: White Sands VillageCondo
Remarks: Welcome to the World-famous Siesta Key Beach. Come check out This well maintained 2-bedroom 2 bath move in ready condo at Whitesands Village across the street from the public beach! Looking to enjoy living the beach lifestyle in Paradise at a great price. This property offers a heated swimming pool, sauna, nice club house, grills. Pet friendly! Siesta Key offers volleyball, pickle ball, yoga on the beach nature trails as well as shopping, restaurants, live entertainment! In Paradise with absolutely gorgeous sunsets !!This unit also offers a covered parking spot. It is also totally furnished with everything you would need just bring your personal belongings. It is available to rent out to friends as well as repeat quest that come back year after year. A new AC and water heater installed in 2023. Seller is Very motivated
Listing is courtesy of: GULF SHORES REALTY & RENTALS (941-549-1845)
Listing Agent: Terry Millett (941-549-1845)
5141 SAINT ALBANS AVE, SARASOTA, FL 34242
$699,000202 Days on yellowkey MLS ID: A4666801
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1131 Built: 1986Community: Siesta BeachSingle Family
Remarks: Tucked away on a quiet, tree-lined street, this elevated Siesta Key home sits high and did not flood, offering peace of mind. Set on a nearly 10,000 sq ft lot with mature Live Oaks and tropical landscaping, this property has a lot going for it beyond just charm. It’s a classic Old Florida-style home with vaulted ceilings, warm wood interiors, and an easy, relaxed layout that fits island living perfectly. Whether you want to keep it as a cute, income-producing Airbnb with active bookings, update it over time, or take advantage of the buildable lot value, there’s real flexibility here. With no HOA or deed restrictions, you’re not boxed into one path. The main level offers open living and dining spaces, a functional kitchen with breakfast bar, and a guest bedroom with full bath. Upstairs, the loft-style primary suite gives you a private retreat with its own sitting area, bathroom, and walk-in closet. A screened porch looks out over the greenery, making it an easy spot to unwind. Recent updates include new porch sliders and custom tile shower, and the 2015 A/C keeps things comfortable year-round. There’s also room for a boat, RV, or trailer, which is hard to come by on the island. Just minutes from Siesta Village and the beach, this is one of those properties that works as a rental, a personal getaway, or a future build, with the added benefit of being priced close to land value in a highly desirable area.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Anthony Dalesandro (941-504-5371)
1350 SIESTA BAYSIDE DR #1350B, SARASOTA, FL 34242
$975,00061 Days on yellowkey MLS ID: A4683073
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 1988Community: Gulf & Bay Club BaysideCondo
Remarks: Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddle boarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
1201 E PEPPERTREE DR #234, SARASOTA, FL 34242
$799,00084 Days on yellowkey MLS ID: A4679932
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1686 Built: 1972Community: Peppertree Bay ITownhouse
Remarks: Private end-unit residence at Peppertree Bay with outdoor patio space, lush tropical landscaping, and an easy stroll to the bayside community pool from the back door. Inside, you’ll find extensive renovations and updates throughout, including new flooring, doors, fans and fixtures, walls, baseboards, and cabinetry. Major system improvements have also been completed, including waste lines, A/C, appliances and washer, dryer. Both the primary and guest baths have been updated along with a major enhancement to the kitchen. The 1st and 2nd floor lanai windows have been recently replaced—bringing in light while providing enhancing comfort and extended living space. A rare combination of privacy, thoughtful upgrades, and that classic Peppertree Bay lifestyle on Siesta Key. Must see and easy to show.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Camille Buck (941-894-4771)
5231 SIESTA COVE DR, SARASOTA, FL 34242
$1,600,00032 Days on yellowkey MLS ID: A4686013
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2557 Built: 1982Community: Siesta Cove SubSingle Family
Remarks: Tucked inside the private enclave of Siesta Cove, this beautifully updated island home offers that rare blend of privacy, space, and an easy walk to world-famous Siesta Key Beach. Set on an oversized 0.35-acre lot, the property features 3 bedrooms, 2.5 baths, and more than 2,500 square feet of bright, open living space designed for both everyday comfort and effortless entertaining. Vaulted ceilings with exposed beam detail anchor the main living area, where expansive sliders open to a screened lanai and private saltwater pool framed by mature tropical landscaping. Porcelain tile runs throughout, creating a clean, cohesive feel that fits perfectly with relaxed island living. The kitchen is thoughtfully designed with stone countertops, stainless steel appliances, generous prep space, and a built-in wine refrigerator, flowing naturally into multiple living and dining areas. Whether you’re hosting friends after a beach day or enjoying a quiet evening at home, the layout simply works. The primary suite feels tucked away and private, complete with an updated bath featuring a rain shower and elevated finishes. Two additional bedrooms offer flexibility for guests, family, or a dedicated office space. Impact windows and doors provide added peace of mind, and the home did not experience water intrusion during recent hurricanes. Additional features include a fireplace for cooler winter nights, an interior laundry room, circular driveway, and attached two-car garage. Siesta Cove is ideally positioned between Midnight Pass Road and the Intracoastal Waterway, just a short stroll to the powder-soft quartz sands of Siesta Key Beach. Here, mornings start with beach walks, afternoons are spent boating or biking the island, and evenings wind down with sunset skies and dinner in the Village. This is not just a home — it’s the kind of island living people move here for.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
4903 COMMONWEALTH DR, SARASOTA, FL 34242
$3,250,000411 Days on yellowkey MLS ID: A4643229
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3146 Built: 2026Community: Siesta BeachSingle Family
Remarks: Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. 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)
353 AVENIDA LEONA, SARASOTA, FL 34242
$1,450,00081 Days on yellowkey MLS ID: A4680536
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1730 Built: 1971Community: Siesta Manor Sec 3Single Family
Remarks: Under contract-accepting backup offers. Positioned along a quiet residential canal just moments from shops and restaurants of Siesta Village and a short distance to world-famous Siesta Beach, this extensively renovated coastal retreat offers the ideal blend of island charm, modern updates and exceptional value. Built in 1971 and thoughtfully reimagined in 2025, this three-bedroom, two-bath residence spans 1,730 square feet and showcases timeless finishes designed for effortless Florida living. From the moment you arrive, tropical landscaping and a welcoming entry set the tone. Natural light fills the expansive living space, where pocket sliding glass doors fully open to the screened lanai, creating seamless indoor-outdoor flow and picturesque views of the pool and canal beyond. The open dining area blends beautifully into the exquisitely updated kitchen, anchored by a striking 9-foot center island with counter-height seating, soft-close cabinetry, undercabinet lighting, terrazzo-inspired recycled glass countertops, designer tile backsplash and stainless-steel appliances. The serene primary suite opens directly to the lanai and features a custom walk-in closet and an elegantly appointed en-suite bath with granite-topped vanity and beautifully tiled walk-in shower. Two additional bedrooms offer walk-in closets, while the guest bath has been thoughtfully updated with quartz vanity and sleek tile finishes. Outdoor living is equally impressive, with a heated pool featuring a seating ledge and newer heater, all set within a fully fenced backyard overlooking the tranquil canal. The covered lanai includes a motorized screen, enhancing comfort and year-round enjoyment. Notable improvements include impact-rated windows and doors, luxury vinyl plank flooring throughout, updated baths, house replumbed in 2025, attic ductwork and insulation replaced, and a completely replaced and repoured seawall in 2020. An attached one-car garage with epoxy flooring and integrated storage adds functionality. Whether you’re seeking a refined island retreat, a smart investment opportunity or a boating-friendly lifestyle just minutes from the Gulf, this move-in-ready Siesta Key home presents a compelling opportunity in one of Sarasota’s desirable coastal communities. Schedule your private showing today.
Listing Agent: Mike Warm, Llc (941-525-2740)
5880 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$1,450,000102 Days on yellowkey MLS ID: A4677116
1 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1854 Built: 1982Community: CasarinaCondo
Remarks: Under contract-accepting backup offers. WHY Should I Consider Casarina? Because this is one of those RARE moments when Buyers can step into a fully modernized community on Siesta Key. It should actually be called "Casarina 2.0" since all the major decisions, major projects, and major disruptions are behind them—including the assessments! Which means today’s lucky buyer is going to enjoy modernized systems, refreshed amenities, and peace of mind from day one without any of the major inconvenience or cost. In other words: it looks and feels fresh, solid, and built for coastal living. ***OKAY, but why buy THIS condo?*** Because, if this exact condo were a few floors higher, you’d be looking at almost $2M. Instead, you’re getting THREE bedrooms, exceptional renovations, professionally decorated, and true TURNKEY furnishings for just $1.45M; making it one of, if not THE smartest value currently available in the community! This three-bedroom, two-bath residence offers an ideal second-floor location, providing the convenience of stairs or elevator access along with gorgeous tropical views. Not to mention it also comes with one of the closest, most coveted, carport parking spaces in the complex. Once inside, you'll find open concept kitchen-dining-living area, a custom built-in bar area with refrigerator and separate ice maker perfect for entertaining, three bedrooms, two bathrooms, a laundry room with additional storage, wall mounted tv’s, ceiling fans throughout, quartz and granite countertops, crown molding, sculptured wall design, plus many more architectural details. The murphy bed in the third bedroom allows it to double as an office. And if you prefer some outdoor space, the sunroom can easily be returned to a lanai with installation of sliding doors between living room and sunroom (estimate from local window/door company has already been prepared). This condo has it all and so does Casarina with over seven acres of lush tropical grounds, its own private beach and on-site management. You can enjoy a resort lifestyle with a heated pool and spa, outdoor shower, basketball, tennis and pickleball courts, clubhouse, outdoor kitchen, boardwalk, sunset deck, and endless sunsets. Just minutes from Siesta Village, the location offers an easy balance of beachfront tranquility and vibrant island life. Call now to schedule a private tour!
Listing Agent: Christa Spalding (941-529-6978)
521 CUMMINGS ST, SARASOTA, FL 34242
$1,495,000193 Days on yellowkey MLS ID: A4667165
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2500 Built: 1983Community: Ocean Beach RepSingle Family
Remarks: One or more photo(s) has been virtually staged. Siesta Key Waterfront Retreat – Walk to the Beach & Village! Ready for immediate enjoyment this winter, this 3-bedroom, 2-bath Key West–inspired home embodies the essence of the Siesta Key lifestyle—boating from your backyard and strolling to the powdery white sands and vibrant Siesta Key Village with its renowned dining, boutiques, and nightlife. Nestled on a quiet cul-de-sac, this canal-front retreat offers 100 feet of waterfront, a covered 5,000-lb boat lift, and direct access to the Intracoastal Waterway. The expansive outdoor living area invites relaxation and entertaining with a heated pool featuring a cascading stone waterfall, covered bar & and wide open fenced area surrounded by tropical landscape creating a private island ambiance. Inside, a neutral palate, high ceilings, and open layout feels light and airy. The white kitchen features granite countertops, stainless steel appliances, dual sinks, a center cooking island, and a breakfast bar perfect for casual dining. Warmth and character is further enhanced by a marble fireplace in the main living and dining areas. The primary suite offers a peaceful retreat with an ensuite bath, dual vanities, a walk-in shower, and a charming window seat. Guests & children have their own wing with a full bath and a convenient laundry room. Enjoy peace of mind with impact windows, hurricane-rated doors, and major upgrades including a metal roof, Trex decking, Nichiha siding, and reinforced lanai. Positioned at one of the highest elevations on the street, the home has never experienced flooding. And there’s an additional ground floor BONUS…a generously sized sunlit air-conditioned play & storage room! Whether you’re searching for a seasonal escape, a full-time residence, or a property with strong vacation rental appeal, this move-in-ready home offers exceptional versatility and potential.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
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