Location: Sarasota , 34242
Do Not Show Listings
157 VISTA HERMOSA CIR, SARASOTA, FL 34242
$569,000127 Days on yellowkey MLS ID: A4677280
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $3,568 (2025)Community: Vista HermosaVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,568
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Completely renovated in 2025, this 2 bedroom/2 bath, maintenance free villa is walking distance to the powdery sands of beautiful Crescent beach on Siesta Key. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy. All kitchen upgrades include new cabinets, quartz countertop, sink and all new stainless steel appliances including, microwave, refrigerator, stovetop and dishwasher. Convenient all new washer and dryer in unit! New tile flooring throughout. Amenities include a renovated clubhouse with full kitchen, heated swimming pool and outdoor grilling areas. This well-managed island retreat is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the stress free, beach lifestyle of Siesta Key!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Denise Barbato (941-400-8773)
4183 ROBERTS POINT CIR #LOT 18, SARASOTA, FL 34242
$3,400,000220 Days on yellowkey MLS ID: A4669711
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3200 Built: 2027 Tax: $11,511 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$11,511
Tax Year: 2024
Remarks: Pre-Construction. To be built. Joint-Venture opportunity partnering with investors up and down Florida's coast. Brought to you by Noah Thomas Builders — where modern luxury meets timeless coastal elegance. A masterclass in luxury homebuilding, this Noah Thomas Builders contemporary coastal home offers an exceptional blend of modern aesthetics and is built to FEMA's latest standards. Step inside this 3240 sqft home offering four bedrooms, four bathrooms, an open-concept floor plan with high ceilings and premium finishes throughout. It features all hurricane-rated windows and doors and is constructed to be as hurricane and flood-proof as possible-giving you peace of mind while living steps from the water. The kitchen boasts quartz countertops, top-tier appliances, and a spacious island perfect for entertaining. Retreat to the luxurious master suite with spa-inspired bath and expansive walk-in closets. Endless sunshine, gentle breezes, and your own private pool and spa — relax, unwind, and entertain in your personal outdoor oasis. Additional highlights include a private elevator, gas generator and wine room. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Your private escape above it all — a space built for sunsets, sea breezes, and unforgettable gatherings. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
1169 W PEPPERTREE DR #118A, SARASOTA, FL 34242
$615,00091 Days on yellowkey MLS ID: A4683913
0 Days Off yellowkey (back on 5/6/2026)
REDUCED by $34,000 (5.2%) on 05/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $4,521 (2025)Community: Peppertree Bay IiiCondo
Taxes:$4,521
Remarks: Under contract-accepting backup offers. Discover this impeccable, light-filled second-floor End unit in Peppertree Bay, offering serene views of the tranquil pond. Meticulously remodeled and lovingly maintained over 20 years, this residence exudes pride of ownership. Featuring two bedrooms and two bathrooms, the unit is complete with impact windows throughout, ensuring safety and comfort. Every square inch of this home has been tastefully enhanced, and the furnishings are included for your convenience. Enjoy the added convenience of an in-unit washer and dryer. Residents of Peppertree Bay benefit from a wealth of resort-style amenities, including a private beach with lounge chairs, two heated swimming pools, a fitness center, saunas, tennis and pickleball courts, barbecue grills, a fishing pier, and dedicated on-site management. Ideally located just a short stroll from Siesta Village’s shops and dining, and a quick drive to Sarasota’s cultural attractions, this property embodies coastal living at its best. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity with rental income potential, this exceptional beachfront property meets all your needs. Don’t miss your chance to embrace the Siesta Key lifestyle—where every day feels like a vacation.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
8764 MIDNIGHT PASS RD #A202, SARASOTA, FL 34242
$600,00033 Days on yellowkey MLS ID: A4690420
3 Days Off yellowkey (back on 5/5/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1975Monthly Fee: $1,033 Tax: $6,674 (2025)Community: Island Reef ICondo
Taxes:$6,674
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. This is the Gulf front opportunity buyers wait for. Positioned in the highly sought after A Building at Island Reef, this two bedroom, two bath beach condo offers direct Gulf front views that simply cannot be duplicated, and is currently the lowest priced Gulf front 2/2 property on Siesta Key. Held in the same family for over 30 years, the condo has been meticulously maintained and remains exceptionally clean and comfortable as it sits today. It presents a rare combination of immediate usability and the opportunity to thoughtfully update over time, allowing a new owner to create their own vision in one of the most desirable Gulf front locations on the island. From the moment you walk in, your eye is drawn straight through to the water. The view opens across the pool, the natural flow of the grounds, and out to the Gulf of Mexico, creating a sense of space, calm, and connection that defines true waterfront living. It is the kind of view that makes you pause and take it in. The layout offers a true split floor plan, providing privacy and comfort for both owners and guests. The main living areas are open and relaxed, with Gulf views from the dining area, living room, and primary bedroom. The kitchen is generously sized, with an eat in area and built in desk space that adds flexibility, while natural light fills the space and keeps it bright and inviting. The primary suite is spacious and set apart as its own retreat, complete with an en suite bath and room to unwind. The guest bedroom is positioned on the opposite side, offering separation and privacy. A full size laundry room adds a level of everyday convenience not always found in beach condos. Impact windows are currently being installed on the lanai, adding long term value, peace of mind, and enhancing the indoor outdoor experience that is so central to Gulf front living. Island Reef is known for its true Gulf to Bay lifestyle. Mornings begin with walks along the private beach at Turtle Beach, afternoons are spent kayaking toward Midnight Pass or relaxing by the Gulf side pool, and evenings are centered around sunsets that never repeat themselves. On the bay side, boats pass throughout the day, adding another layer of movement and life to the setting. The community offers bay access with dockage and lift capability, along with direct access to Sarasota Bay and the Gulf beyond. Two heated pools, including the beautifully positioned Gulf side pool, along with tennis, pickleball, and shuffleboard courts create an active yet balanced lifestyle. Residents enjoy a clubhouse, library, fitness rooms, and gathering spaces designed for both connection and relaxation. Additional features include kayak and bike storage, a fishing pier, on site management, and a well run on site rental program offering monthly rental opportunities, providing flexibility for owners who wish to offset expenses. Winding walkways connect the community through mature landscaping and open green space, while brick paver parking areas, covered parking, secure lobby entry, elevator access, and guest parking all add to the ease of ownership. Call today for your private showing. Gulf front opportunities in this building, at this price point, are rare and do not last. Video, 3D tour, and floor plan available.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
7324 POINT OF ROCKS RD, SARASOTA, FL 34242
$16,000,000428 Days on yellowkey MLS ID: A4643281
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5524 Built: 2025 Tax: $32,550 (2024)Community: White Beach Fruit Co PropSpa: YesSingle Family
Taxes:$32,550
Remarks: Newly completed Gulf-front coastal contemporary home on prestigious Siesta Key by Murray Homes. This 5BR/5BA/1HB residence offers approx. 5,500 sq. ft. of living space plus 2,600 sq. ft. of recreational non-conforming space. Features include a gourmet kitchen with large island, walk-in pantry, wine refrigerator, and built-in coffee system, opening to a spacious great room with fireplace. Smart home technology, high-end lighting, and whole-house generator. Outdoor living includes Gulf-front pool and spa with beach shelf, expansive deck, summer kitchen, fireplace, and lounge areas. Upstairs lounge with vaulted wood ceilings and beverage refrigerator, plus 4 en-suite bedrooms, many with Gulf views. Primary suite with soaking tub, oversized shower, and dual vanities. Private beach on a secluded street with panoramic Gulf views. 4-car garage plus golf cart/kayak garage
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Karen Chandler (941-544-4919)
5345 SIESTA CT, SARASOTA, FL 34242
$1,160,00083 Days on yellowkey MLS ID: A4685607
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2272 Built: 1977Monthly Fee: $45 Tax: $5,278 (2025)Community: Siesta Cove SubSingle Family
Taxes:$5,278
Remarks: Welcome to Siesta Cove on Siesta Key, just minutes from world famous Siesta Key Beach. This bright, well maintained home offers comfortable island living in one of the area’s most desirable neighborhoods. The layout provides excellent flexibility with both a living room and a separate family room, giving you plenty of space to relax or entertain guests. Oversized windows throughout the home bring in natural light and offer beautiful views of the mature tropical landscaping, creating an inviting atmosphere. Built in cabinetry and shelving add character to the living room, while the two skylights in the family room bring in beautiful natural light throughout the day. The kitchen offers granite countertops, a large island with seating, and generous cabinet storage. The cabinets are real maple with soft close drawers and doors, crown molding, and lighted glass display cabinets. Additional conveniences include under cabinet lighting and pull out drawers, making storage easy and accessible. The primary suite serves as a comfortable private retreat. It features a large walk in closet with built in organization and an en-suite bathroom with dual vanities, granite countertops, and a spacious tiled shower. After spending the day at Siesta Key Beach, you can rinse off at the outdoor shower before heading inside. Two outdoor living areas allow you to enjoy Florida’s coastal climate: a front entrance lanai and a private lanai off the family room, both ideal for morning coffee or relaxing in the evening. The side load two car garage enhances the home’s curb appeal and provides additional storage space. Several major systems have already been updated. The roof was replaced in 2020, including two skylights. The home also features PVC sewer lines, the air conditioning system was replaced in 2022, and the water heater was replaced in 2023. Best of all, the property experienced no damage during the recent storms, providing additional peace of mind for buyers. This is a wonderful opportunity to enjoy the relaxed lifestyle of Siesta Key, just minutes from the beach, dining, and everything the island has to offer.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
6713 MIDNIGHT PASS RD #4, SARASOTA, FL 34242
$330,000386 Days on yellowkey MLS ID: A4651929
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 598 Built: 1974 Tax: $4,050 (2024)Community: Casa SiestaCondo
Taxes:$4,050
Remarks: BACK ON THE MARKET, FINANCING FELL THROUGH. Looking for your piece of paradise? This fully furnished one-bedroom, one-bath unit is near Siesta Key's stunning beaches. Just bring your clothes and toothbrush. Ideal for snowbirds, investors, or those seeking island life. Conveniently located near the Village of Siesta Key's amenities. Brand new A/C May 2026.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Toni Lyon (941-928-8735)
4646 GLEASON AVE, SARASOTA, FL 34242
$1,350,000145 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)
6234 MIDNIGHT PASS RD #307, SARASOTA, FL 34242
$1,100,00032 Days on yellowkey MLS ID: A4692040
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1979 Tax: $9,703 (2025)Community: Siesta Dunes BeachCondo
Taxes:$9,703
Remarks: Siesta Key offer this Two Bedroom, Two Bath home with Full Views of the Gulf of Mexico. Turnkey furnished. Carport and storage closet. Screened lanai. Weekly rental can give you extra income. Both bedrooms have walk-in closets. Impact windows. You can enjoy the beach chairs and lounges on the famous "White Sand Beach", Gulf front circular pool that is the centerpiece of the community. On-site management. This centrally located community is near shopping and restaurants. It is a short trolley ride to Siesta Key Village.
Listing Agent: Marlene Marshall (941-539-8850)
4922 COMMONWEALTH DR, SARASOTA, FL 34242
$1,795,000249 Days on yellowkey MLS ID: A4666313
4 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2767 Built: 1995 Tax: $6,523 (2025)Community: Siesta BeachSpa: NoSingle Family
Taxes:$6,523
Remarks: Welcome your Siesta Key dream home Commonwealth Drive, a stunning custom residence located directly on the Grand Canal. This four bedroom, four bathroom home exudes island style and warmth from the moment you see it. The Key West style build has a concrete base level, hardy plank cement siding, and a standing seam metal roof. The main living areas all give way to sunny and palm-lined views of pool deck with saltwater canal in the background. The open living areas on the main level feature hardwood flooring, a gas built-in fireplace, built-in shelving, and lots of windows to enjoy the view. The primary suite features lots of space, dual walk-in and an upper level balcony with incredible views. There’s a second larger suite with sitting area to make guests feel at home, and two more bedrooms for the ultimate in flexibility. This home is truly all about the location- want to go paddleboarding or out on your kayaks? Right in the back yard. The beach is just a few blocks away and the northern Siesta Key location gives easy access to downtown Sarasota and beyond. If you’re looking for the perfect combination of space, privacy, convenience, and of course a little sand between your toes- this may be the perfect home for you. Boaters will also love this Grand Canal location, with only one large fixed bridge and easy access to Sarasota Bay. Don’t hesitate, schedule your showing of this fine home today!
Listing Agent: Drew Russell (941-993-3739)
783 BIRDSONG LN, SARASOTA, FL 34242
$999,900211 Days on yellowkey MLS ID: A4670796
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1905 Built: 1973 Tax: $11,733 (2025)Community: Siestas Bayside Waterside SouthSpa: NoSingle Family
Taxes:$11,733
Remarks: Experience Coastal Living at its finest in this turnkey-furnished, three-bedroom, two-bath retreat tucked away on a quiet cul-de-sac in a private community just minutes from the beach! This home features the ULTIMATE OUTDOOR living space with numerous updates offering the perfect blend of style, comfort, and low-maintenance lifestyle. As you step through the front door, you’re greeted by a bright open floor plan enhanced by tasteful coastal décor and tile flooring. Multiple dining and entertaining spaces flow effortlessly into the spacious family room, ideal for relaxing or hosting guests, with direct access to the stunning pavered pool area. The beautifully appointed kitchen features stainless steel appliances, abundant counter space, and a convenient breakfast bar for additional seating. Retire to the serene primary suite which offers a walk-in closet and a well-designed bath with dual sinks, and opens directly to the INCREDIBLE new 21' x 24' covered lanai—an inviting extension of your living space. This IMPRESSIVE private outdoor oasis features pavers, remote-controlled ceiling fans, sconce lighting, and a remarkable sunset overlooking the relaxing pool complete with dramatic lighting for that special ambience. Enjoy privacy and seclusion in your backyard retreat which is fully enclosed with a 7 foot vinyl fence. An outdoor shower adds convenience after a day at the beach. The exterior has been expertly refreshed with new hardiplank siding, fresh paint, and attractive stone accents. A premium landscaping package includes full irrigation, shell for low maintenance, and landscape lighting to set the perfect atmosphere. Additional upgrades elevate peace of mind and efficiency: a 2024 roof, hurricane-rated windows and doors, new pool pump, attic insulation, new garage door and opener, and a newly pavered front walkway and driveway with a charming sitting area and extra parking. This beautiful home reflects pride of ownership and detail with so many updates and most important no flooding during the storms! Ideally located close to Siesta Key Village, just one mile from world-renowned Siesta Key Beach, and near shopping, dining, and ODA school, this home is perfectly suited as a primary residence, vacation retreat, or exceptional rental opportunity!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Lori Lockhart, Pa (941-724-0595)
6006 MIDNIGHT PASS RD #48, SARASOTA, FL 34242
$405,00030 Days on yellowkey MLS ID: A4691484
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 420 Built: 1960 Tax: $2,987 (2025)Community: Casa MarSpa: NoCondo
Taxes:$2,987
Remarks: Great opportunity to own in Casa Mar on Siesta Key with strong value-add potential. Studio unit with updated lower kitchen cabinetry, quartz countertops, and stainless sink already in place. Unit is ready for buyer to install appliances and replace A/C—priced accordingly. Ideal for investors or buyers looking to customize. Premium location within the community with pool directly behind the unit and easy access to the beach path leading to Siesta Key’s world-renowned powdery quartz sand and breathtaking Gulf sunsets. Enjoy the true island lifestyle with morning walks on the beach, warm evening breezes, and some of the most spectacular sunsets on Florida’s Gulf Coast just steps away. Weekly rentals permitted—excellent income potential. Condo association includes cable, internet, water/sewer, building insurance, and exterior maintenance.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Susan Beaver, Llc (732-489-3727)
1215 S PORTOFINO DR #107, SARASOTA, FL 34242
$425,00031 Days on yellowkey MLS ID: A4692252
0 Days Off yellowkey (back on 5/3/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968 Tax: $3,442 (2025)Community: Siesta Harbor ISpa: YesCondo
Taxes:$3,442
Remarks: Under contract-accepting backup offers. WATERFRONT SIESTA HARBOR!DIRECT VIEWS OF THE CANAL, walk right out to the canal from your Lanai! BEACH ACCESS ACROSS THE STREET! Turn-Key Furnished with a Canal View! Move in ready, enclosed lanai with all furniture and furnishings included! Highly Sought after remodeled Unit on the Canal in the Dolphin Building! Close to the Resort-style Heated Swimming Pool and Spa on the wide part of the canal. This Charming condo is adorned with large windows, bathing the dwelling in warm, natural light. Combining dining and living space, this turn-key furnished condo is Spacious, light and airy with a Gorgeous updated kitchen with granite countertops! Just move right in or rent until you retire! It's ready for your enjoyment! Active 55+ community, close to the pool, clubhouse, beach access, SCAT, the trolley right outside your door! Beautifully done, tile through out, great coastal feel! TURNKEY FURNISHED! This is a great community lots of activities, fitness room, saunas, outdoor spa, heated pool, on site free laundry, pier on the main intracoastal waterway to relax and fish each day, plus boat slips as available, for a reasonable fee through the Association. The location is wonderful, easy on and off the key, walk to shops, restaurants, mini-donuts! Elevate your living experience in this ready-to-move-in, fully furnished home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota; your new home awaits!
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Judith Guzzi (914-490-9032)
6005 MIDNIGHT PASS RD #N4, SARASOTA, FL 34242
$799,999141 Days on yellowkey MLS ID: A4677763
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1966 Tax: $7,741 (2025)Community: Provincial GardensVilla
Taxes:$7,741
Remarks: Perfect Snowbird Getaway! Mid Siesta Key, highly sought after, free-standing villa with it’s own private courtyard front, side and rear. Maintenance Free condo lifestyle that feels like a single family home. Situated in Provincial Gardens on a lushly landscaped and tree canopied street of only 26 units offering old Florida charm. This updated, Turnkey Furnished 2 bedroom + Den, 2 bath offers 1400sf. Spacious owner’s suite features a private patio; wall of closets; and ensuite bath. The updated kitchen offers abundance of cabinets and counterspace & newer appliances. The open floor plan offers tile floors throughout; abundance of sliding glass doors opening to your surrounding private courtyard; Florida room; updated baths; Full Size washer/dryer utility closet; new hot water heater 2023; New roof 2023; & Storage Shed 10x6. The crown jewel of this community is the enormous Bay front park with spacious paver patio where owners and their guests enjoy exquisite sunrises and picturesque sunsets while watching the dolphins, manatees, birds and boaters play in the intracoastal waterway. In addition, there is a new seawall, day dock with canoe/kayak launch, and plenty of room to try your luck at fishing. In addition, owners enjoy deeded beach access; beach chair usage; and jr. Olympic heated pool across the street at the Aloha Kai Community. It is also comforting to note that this community sustained no water damage from any recent hurricanes. This Beach to Bay Retreat is ready as a rental or personal winter getaway for you, your family and friends. This mid-key location is an easy Breeze Bus or Froggy Hop ride to Siesta Key Village; Tennis Courts; Public Beach; Grocery; and abundance of restaurants. Don't delay; these units are rarely available and sell fast.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Linda Starcher, Pa (941-780-2396)
5880 MIDNIGHT PASS RD #906, SARASOTA, FL 34242
$1,150,000214 Days on yellowkey MLS ID: A4670194
REDUCED by $45,000 (3.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $7,217 (2024)Community: CasarinaCondo
Taxes:$7,217
Remarks: The least expensive unit in the sought-after Casarina on Siesta Key with another price reduction of $50,000! This Top-floor unit offers stunning views of Siesta Beach and all the comforts of home. The interior has been tastefully updated with modern finishes and stylish decor. The unit is being sold furnished (minus few staging items). The kitchen has newer cabinets and upgraded appliances. Enjoy the spaciousness of the living/dining combination area and be drawn to the expansiveness of the enclosed patio where you can enjoy evening sunsets. The 17-by-12-foot primary bedroom has luxury vinyl flooring and room for a small desk area. The primary bath has new vanities, mirrors and lighting. Casarina has seven acres of newly planted tropical landscaping and 200 feet of private beach. The main lobby has recently been updated. Spend your days swimming in the heated pool, soaking in the spa, playing tennis, pickleball, basketball or simply enjoying the quiet beauty of the #1 Siesta Key Beach. With covered parking, a secure lobby and an on-site manager, everything you need is right here. Enjoy being close to the shops and restaurants of Siesta Village and only minutes from downtown Sarasota’s arts, dining and world-class healthcare. This is your chance to own and live in beautiful Sarasota. Owner has paid all the present assessments for the new upgrades to the property and building.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
5302 LAS ROSAS, SARASOTA, FL 34242
$725,000307 Days on yellowkey MLS ID: A4659614
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1962Monthly Fee: $4 Tax: $3,190 (2024)Community: Sarasota BeachSingle Family
Taxes:$3,190
Remarks: Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build your dream home or use the current home as an investment or just enjoy the Island lifestyle. Current home has 2 bedrooms, 2 baths and a 2-car garage. Terrazzo floors throughout. The fenced back yard is a Tropical Paradise for taking in the soothing Gulf Breeze.
Listing Agent: Dan Miller (941-376-7442)
1050 W PEPPERTREE LN #116B, SARASOTA, FL 34242
$669,00089 Days on yellowkey MLS ID: A4684958
0 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $5,344 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$5,344
Remarks: Turnkey coastal living on Siesta Key. Beautifully renovated first-floor Gulf-side garden condominium in the highly sought-after Peppertree Bay Gulf-to-Bay community. This exceptional two-bedroom, two-bath residence has been thoughtfully updated throughout and is offered fully turnkey furnished, creating an effortless opportunity to arrive and immediately enjoy the island lifestyle. The bright end-unit layout features a rare windowed kitchen that fills the living space with natural light, a feature seldom found in comparable garden units. The residence has been extensively improved with brand-new hurricane-impact windows, new flooring throughout, and numerous major system upgrades, including a recently replaced HVAC system, hot water heater, and dishwasher, providing peace of mind and reducing future maintenance expenses for the next owner. In addition, there is expanded square footage, enhancing the overall functionality of the home. The enclosed lanai area overlooks a tranquil lagoon and fountain, offering a peaceful setting for morning coffee or evening relaxation. Additional conveniences include a private in-unit washer and dryer, a dedicated exterior storage room, and assigned parking just steps from the entrance. Peppertree Bay is one of Siesta Key’s most desirable waterfront communities, uniquely positioned Gulf-to-Bay and offering a full suite of resort-style amenities that support a true full-service coastal lifestyle. Residents enjoy private beach access with chairs, two heated swimming pools, tennis courts, pickleball courts, a fitness center, fishing pier, newly updated clubhouse, gas grills, and on-site management with rental services. Ideally located just minutes from Siesta Key Village’s restaurants, shopping, and the world-renowned quartz sand beaches, this beautifully updated residence offers a rare combination of turnkey convenience, meaningful capital improvements, expanded living space, and premier coastal location. While the current owners have chosen not to rent the property, Peppertree Bay’s on-site rental management and strong seasonal demand provide an excellent opportunity for owners who wish to generate rental income.
Listing Agent: Renee Nadiv (941-299-4242)
5855 MIDNIGHT PASS RD #227, SARASOTA, FL 34242
$499,000137 Days on yellowkey MLS ID: TB8463933
1 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1976 Tax: $4,947 (2025)Community: Harbor Towers Y & RCondo
Taxes:$4,947
Remarks: Under contract-accepting backup offers. Have you been searching for your own slice of tropical paradise on Siesta Key? Look no further than this pet-friendly, 2-bedroom, 2-bathroom residence in the perfectly located Harbor Towers Yacht & Racquet Club. This updated home feels fresh and inviting with new luxury vinyl wood-plank style flooring and brand-new hurricane impact-resistant windows for total peace of mind. Harbor Towers is a well-established community situated right in the heart of "The Key," just across the way from the world-famous Siesta Key Beach and a short distance from vibrant shopping and dining. Life here feels like a permanent vacation with access to a resort-style swimming pool, an oversized hot tub, three Har-Tru tennis courts, a fitness center, and a social room with a catering kitchen. Boaters will especially love the on-site marina, where boat slips are available on a first-come, first-served basis for a nominal monthly hook-up fee. Whether you are looking for a primary residence, a seasonal getaway, or a smart investment with a documented rental history, this hidden gem is ready for you. Come and see what makes this such a special place to live!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
925 BEACH RD #310, SARASOTA, FL 34242
$599,000274 Days on yellowkey MLS ID: TB8422646
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972Monthly Fee: $908 Tax: $5,378 (2024)Community: La SiestaCondo
Taxes:$5,378
Remarks: Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!
Listing is courtesy of: BRICK STREET REALTY (727-512-6615)
Listing Agent: Colin Mooney (727-512-6615)
618 AVENIDA DE MAYO, SARASOTA, FL 34242
$1,200,00032 Days on yellowkey MLS ID: A4692001
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2961 Built: 1948 Tax: $8,283 (2025)Community: Sarasota BeachSingle Family
Taxes:$8,283
Remarks: This Charming Old 1948 Bungalow located just 3 Blocks behind Siesta Key Village and 4 Blocks to Siesta Key Beach!! It is quite the Interesting Property! It was converted into a Triplex many moons ago. It can easily be converted back to a single family residence. Currently, there are 2 Beds and 2 Baths downstairs and 2 Beds 1 Bath upstairs. There are 3 Kitchens, 3 Liv Areas 2 down, 1 up and there is a Bonus Rm down as well as a Screened in Patio on the front West side of the Home, an Open Patio on the East Side and a Closed in Upstairs. And, there's more... At the Rear of the Property is a Cottage, perfect for a Mother In Law Suite or Rental. It is a 1/1 with a full Kitchen and Liv Area. The grounds are Etherical, as there are private little Sitting Areas for each sector and in the center of the Backyard there is a Wash House for Laundry as well as an attached Storage Shed for Gardening. There are additional Outside Storage Units for each of the apartments, again, really a cool old school house with so much to offer. Make it back into a single family or keep it the way it is and rent the house and utilize the cottage for a personal vacay spot! Questions, call me!!
Listing is courtesy of: BLAKELEY & ASSOCIATES REALTY (941-567-3100)
Listing Agent: Lisa Blakeley (941-809-1647)
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