Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
8282 BARTON FARMS BLVD, SARASOTA, FL 34240
$829,0002 Days on yellowkey MLS ID: A4689205
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2982 Built: 2006Monthly Fee: $225 Tax: $5,190 (2025)Community: Barton FarmsSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,190
Elementary School: Tatum Ridge Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Welcome to an exceptional residence in the sought after Barton Farms community, where refined design meets resort style living. This fully remodeled four bedroom, three bathroom estate with dedicated office showcases a professionally curated interior with elevated finishes and thoughtful upgrades throughout. Step inside to discover soaring ceilings, eight foot doors, oversized baseboards, and extensive crown molding that create a grand yet inviting atmosphere. The expansive floor plan features ceramic tile and authentic real hardwood floors and is anchored by a beautifully upgraded chef’s kitchen with granite countertops, premium appliances, dovetail soft closing cabinetry, and seamless flow into the main living spaces, perfect for both everyday living and entertaining. A whole home surround sound system enhances the experience throughout. Designed for both luxury and versatility, the home features a private movie theater and a custom climate controlled wine cellar with approximately 300 bottle capacity, complemented by a built in cigar humidor and its own dedicated HVAC system. A separate in law suite or bonus space offers exceptional flexibility, complete with a private entrance, bedroom, kitchenette, and living area. The primary suite is a true retreat, offering a wet bar, electric blackout shades, and elegant plantation shutters for ultimate comfort and privacy. Outdoors, enjoy a spectacular waterfront setting with panoramic screened views of a serene lake and preserve. The custom heated saltwater pool and spa measuring 32 by 23 feet features deck jets and is surrounded by sealed pavers and a new panoramic pool cage. The fully equipped tiki hut outdoor kitchen includes granite countertops, grill, cooktop, refrigerator, and sink, creating the ultimate space for entertaining Florida style. Additional highlights include a three-car garage with finished floors, 2023 HVAC systems and a 2024 natural gas water heater, whole-home gas service, a whole-house water filtration and softener system, a security system with surveillance cameras, and landscape lighting with reclaimed water irrigation. Located within a gated community offering tennis courts, clubhouse, and pool, this property also benefits from low HOA fees and no CDD. Ideally situated just minutes from Siesta Key Beach and Downtown Sarasota, this home is offered furnished, including electronics, for a truly turnkey opportunity. *Please note - Fences are NOT allowed. This is a rare offering that combines luxury, functionality, and lifestyle designed to impress the most discerning buyer.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Paul Bachmann (813-786-6242)
4228 TERN ST, SARASOTA, FL 34232
$290,000Listed 04/17/2026 2:23PM MLS ID: A4690324
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1329 Built: 1962 Tax: $1,073 (2025)Community: Sarasota SpgsSingle Family
Taxes:$1,073
Elementary School: Brentwood Elementary
Remarks: One or more photo(s) has been virtually staged. Opportunity knocks in Sarasota! This 2-bedroom, 2-bath home with a bonus room is ready for your vision and updates. Recent big-ticket improvements include a 2024 roof and 2020 A/C. Inside, you'll find ceiling fans in all rooms, crown molding in the living room, dining room, & hallway, a large kitchen with a peninsula island, and a flexible bonus-room space featuring triple glass pocket sliders for great indoor/outdoor flow. Outside, enjoy a very large, fully fenced backyard with plenty of room to add a lanai and a pool, plus a large driveway parking for 4+ vehicles. Solid concrete construction. Convenient Sarasota location near shopping, dining, and everyday essentials, and just a short drive to Siesta Beach - name the #1 beach in the U.S. and a top 5 beach worldwide in Tripadvisor's Travelers' Choice Awards: Best of the Best Beaches (2025). Sold as-is.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Alfredda Smith Hurst, Pa (941-504-5758)
2347 BENEVA TER #2251, SARASOTA, FL 34232
$229,90072 Days on yellowkey MLS ID: A4680520
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1363 Built: 1978Monthly Fee: $559 Tax: $2,941 (2025)Community: Terraces Of Forest LakesCondo
Taxes:$2,941
Elementary School: Wilkinson Elementary
Middle School: Brookside Middle
Remarks: PRICE IMPROVEMENT Seller Pays First 6 months of HOA Fee.....Move right into this UPDATED 2 BEDROOM, 2 BATH CONDO . . . FIRST FLOOR END UNIT . . . . . COVERED ASSIGNED PARKING RIGHT AT THE FRONT DOOR . . . OPEN AND BRIGHT . . . INDOOR OUTDOOR PATIO SPACE . . .SPLIT FLOOR PLAN . . . Introducing a beautifully updated 2-bedroom, 2-bath condo centrally located in Terraces of Forest Lakes off Beneva. The tasteful updates combine modern elegance with comfort and function. The newly updated contemporary kitchen with solid wood cabinets, quartz countertops, ceramic tile flooring and stainless steel appliances makes it a perfect space for cooking and entertaining. Both bathrooms have also been thoughtfully updated, enhancing the overall appeal of the home. The unit has been freshly painted, giving it a bright and inviting atmosphere throughout. Enjoy the convenience of a full-size washer and dryer right inside the home, eliminating the hassle of laundry days. AC 2013 just serviced, Hot Water Heater 5/2016. Say goodbye to dated popcorn ceilings, as this condo proudly showcases updated ceilings, stylish new ceiling fans and recessed lighting, adding a fresh and airy ambiance to the living space. The enclosed lanai offers a serene spot to unwind, providing a perfect blend of indoor and outdoor living. For your convenience, covered carport parking is steps from your front door, keeping your vehicle protected from the Florida sun and ensuring easy access to your home. Located just a short distance from downtown Sarasota, the beautiful beaches of Lido and Siesta Key, and the scenic Legacy Trail, this condo is ideally situated for those who appreciate both leisure and convenience. Don’t miss the opportunity to make this exquisite condo your own! All information provided by the seller is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
850 S TAMIAMI TRL #308, SARASOTA, FL 34236
$349,000Listed 04/17/2026 3:05PM MLS ID: A4689921
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 876 Built: 1997 Tax: $3,880 (2025)Community: Central Park Sec 2 Ph 1Spa: YesCondo
Taxes:$3,880
Elementary School: Southside Elementary
Remarks: "I'm looking for a 2-bedroom, ground-floor condo with a view of the pond and has a long lanail." It's the most common request--there is only one like that in Central Park II, and for the first time in six years, it's on the market! The seller invested $40,000 in upgrades. This condo is a bit of an anomaly in Central Park II. Come see this beautiful place with a split floor plan, upgraded bathrooms, kitchen and a guest room with built-in shelving. Turn-key ready. Central Park II is the best kept secret in Sarasota real estate. This price-point combined with this central location and level of amenities (pool, court, fitness room, kayaking, etc.) is simply not available anywhere else. It's a short walk to Main Street, the bayfront, the Legacy Trail, Sarasota Memorial Hospital and Selby Gardens. It's a 20 minute bike-ride to Lido Key and Siesta Key Beaches. Easy to rent.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Ray Collins (941-228-0091)
2660 DICK WILSON DR, SARASOTA, FL 34240
$1,349,000Listed 04/17/2026 6:20PM MLS ID: A4690365
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3166 Built: 1997Monthly Fee: $369 Tax: $6,823 (2025)Community: Laurel Oak Estates Sec 10Single Family
Taxes:$6,823
Remarks: Laurel Oak Estates- beautifully situated on a private .91-acre lot with mature landscaping, this spacious four-bedroom home with office/den offers 3,166 sq ft of comfortable living. Thoughtfully designed with custom window treatments, crown molding, and a deluxe lighting system throughout, the home blends elegance with everyday functionality. Kitchen features a large island, Corian countertops, white cabinetry & opens to the main living areas. Sliding glass doors lead to an expansive outdoor space with a large pool and spa, creating a true indoor-outdoor lifestyle. Additional highlights include impact windows, a newer tile roof, and a three-car garage providing ample storage. Located within the guard-gated community, this private property offers both security and serenity in a beautiful setting. Membership in Laurel Oak Country Club is optional. Two championship golf courses, 12 Tru-Har tennis courts, pickleball, and an active social calendar! Come live the Lifestyle!
Listing Agent: Linda Dooley (941-400-7359)
2303 LOMA LINDA ST, SARASOTA, FL 34239
$1,899,000109 Days on yellowkey MLS ID: A4676235
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2708 Built: 2025 Tax: $4,955 (2025)Community: Loma Linda ParkSpa: NoSingle Family
Taxes:$4,955
Elementary School: Alta Vista Elementary
Remarks: Fantastic $100,000 price reduction!!! In the well-established Loma Linda Park neighborhood in Sarasota, this new construction, Divald Homes custom-built two-story home offers a blend of modern design and traditional elements. The home is ideally near downtown Sarasota, Siesta Key and Sarasota Memorial Hospital, with no deed restrictions or HOA fees. The home features four bedrooms and three baths, including a spacious primary suite on the main floor. The open-concept floor plan featuring a 24-by-48-inch modern floor tile throughout, hurricane impact sliding doors and windows offers a light-filled welcoming space ideal for entertaining. The main floor includes a gourmet kitchen, dining area, living room, private den/bedroom 4, primary suite with an ensuite bath and a dedicated laundry room. The chef’s kitchen is a centerpiece, showcasing Bosch appliances, an oversized island with waterfall quartz countertop, and custom floor-to-ceiling full-overlay cabinetry in a beautiful honey-stained wood tone. The living room is highlighted by a striking tile accent wall with custom wood shelving and modern designed 42-inch linear electric fireplace. The living room opens seamlessly to the lanai, complete with an outdoor kitchen, including a gas grill, refrigerator and sink. You will also enjoy the pool with sundeck, oversized outdoor patio and a beautiful backyard with lush native plantings. A convenient pool bath offers direct access from the lanai and the private den. The dining area is elegant and inviting, featuring a statement iron chandelier and a wall of windows overlooking the backyard. Just off the kitchen, the main-floor primary suite serves as a private retreat with a luxurious en-suite bath featuring a marble stone accent wall, a large walk-in shower with seamless glass enclosure, a sculptural slipper tub, double vanity with quartz countertops, natural wood cabinetry, LED mirrors and a spacious walk-in closet with custom built-ins. The laundry room is conveniently near the oversized two-car garage with 12-foot ceilings, large windows for natural light and direct access to the side yard. Upstairs, an ornate wrought-iron and hardwood staircase leads to two additional bedrooms, a beautifully finished guest bath and a versatile flex room ideal for a game room, study or guest accommodations. This thoughtfully designed home offers refined finishes, flexible living spaces and an exceptional location, ideal for enjoying the Sarasota lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
5880 MIDNIGHT PASS RD #906, SARASOTA, FL 34242
$1,150,000168 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
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
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.
8977 MIDNIGHT PASS RD #222, SARASOTA, FL 34242
$589,900103 Days on yellowkey MLS ID: A4676582
58 Days Off yellowkey (back on 4/17/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,552 (2025)Community: Sunrise Cove Sec 3Condo
Taxes:$5,552
Remarks: Under contract-accepting backup offers. Luxury Waterfront Living Spectacular Views, Resort-Style Amenities Wake to breathtaking sunrises over Little Sarasota Bay and the Intracoastal Waterway. This fully remodeled and furnished 2-bedroom, 2-bath condo offers 1,093 square feet of refined coastal living where the views are the true centerpiece. The Residence Thoughtfully renovated in 2024, this residence blends the modern finishes with timeless coastal elegance. The open living and dining areas are bathed in natural light and perfectly positioned to capture sweeping water views, creating an inviting space for both everyday living and entertaining. Features include: 2 Bedrooms, 2 Bathrooms 1,093 Square Feet Panoramic Bay & Intracoastal Views Luxury Vinyl Flooring (2024) New Stainless-Steel Appliances (2024) New Hot Water Heater (2024) New A/C System (2025) Quartz Countertops Offered Fully Furnished with Upscale Furnishings & Accessories Move-In Ready Resort-Style Waterfront Community Enjoy an amenity-rich lifestyle designed for relaxation, wellness, and recreation: Tennis & Pickleball Courts Two Heated Pools-Including an Olympic-Size Pool with Lap Lanes Clubhouse with Pool Table and Ping Pong Fitness Center with Weight & Exercise Equipment Boat Docks Available for Lease Waterfront Setting with Direct Intracoastal Access An Unmatched Coastal Location Turtle Beach directly across the road Shuttle stop providing easy access to Siesta Beach and Siesta Village World-class beaches, boating, dining, and shopping just minutes away The Lifestyle This home is all about the views- sparkling water, passing boats, and unforgettable sunrises enjoyed from the comfort of your living space. Whether as a primary residence, seasonal retreat, or investment property, this condo delivers a luxury waterfront lifestyle with effortless ease.
Listing is courtesy of: PETER D DONAHUE LICENSED REAL ESTATE BROKER (239-206-0740)
Listing Agent: Peter Donahue (239-206-0740)
2344 BAY ST W, SARASOTA, FL 34237
$1,350,000162 Days on yellowkey MLS ID: A4671233
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1930 Built: 2026 Tax: $3,809 (2023)Community: Poms Park 3Spa: NoSingle Family
Taxes:$3,809
Tax Year: 2023
Remarks: Pre-Construction. To be built. Discover exceptional value in this brand-new, single-story 3-bedroom, 2.5-bath modern home located within Sarasota city limits, allowing for weekly rentals, perfect as a full-time residence, vacation retreat or income-producing property. Step inside to find imported Italian cabinetry, flooring and fixtures, hurricane impact windows and sleek contemporary finishes that define understated elegance and lasting quality. The open-concept layout offers seamless flow between living spaces, ideal for entertaining and everyday living. Your private outdoor oasis awaits with an in-ground pool, outdoor shower and spacious patio for relaxing or hosting guests under the Florida sun. Perfectly positioned just steps from The Legacy Trail and only minutes to downtown Sarasota, parks, shopping, dining and the area’s world-renowned beaches, this home offers the best of modern design and unbeatable convenience. Sarasota living at its finest, whether you’re investing, vacationing or settling in, this opportunity won’t last!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
2082 ORCHID ST, SARASOTA, FL 34239
$449,000Listed 04/17/2026 5:58PM MLS ID: A4690466
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1958 Tax: $3,780 (2025)Community: South GateSpa: YesSingle Family
Taxes:$3,780
Remarks: Exceptional opportunity in the heart of Sarasota! Located within city limits, this 3-bedroom, 2-bath home offers a rare advantage with legal short-term rental allowance and an established rental history, making it ideal for both investors and primary homeowners. Offered turnkey furnished, this property is truly move-in or rental ready. Immediately walking in you are greeted with the open kitchen, living room, and dining room. Perfect for entertaining and enjoy a catch up of the day at the beach. The thoughtfully designed split floor plan provides privacy for the owner’s suite and guests, while a dedicated office overlooks the expansive backyard. The large, fenced lot creates the perfect setting for entertaining, complete with an open outdoor space and private jacuzzi for relaxing Florida evenings. Positioned in a highly desirable location, this home is walkable to shopping and dining along Siesta Drive, located within the sought-after Southside School District, and just minutes to downtown Sarasota and world-renowned Siesta Key Beach. Whether you’re seeking a full-time residence, vacation home, or income-producing property, this one offers versatility, location, and lifestyle all in one.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Kari Klein (941-961-7419)
5026 CALLE MINORGA, SARASOTA, FL 34242
$990,000Listed 04/17/2026 5:10PM MLS ID: A4690532
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1954 Tax: $11,005 (2025)Community: Mira Mar ExitSingle Family
Taxes:$11,005
Remarks: RARE OPPORTUNITY IN SIESTA KEY VILLAGE! This charming cottage-style property is ideally located in the heart of Siesta Key Village, just steps from world-renowned Siesta Beach, boutique shopping, and vibrant dining. Zoned OPI (Office, Professional, Institutional), this versatile property offers endless potential for professional office use, boutique business, or residential conversion (buyer to verify). Offered TURN-KEY FURNISHED, this property is move-in or business-ready from day one—an incredible advantage for buyers seeking a seamless transition. Featuring 3 bedrooms, 1 bathroom, a full kitchen, and a spacious Florida room, the layout provides flexibility for a variety of uses. The property has been freshly painted and is move-in ready, with a metal roof approximately 8 years old. A new shell driveway offers convenient on-site parking, a rare find in the Village. Enjoy a peaceful, private setting while being right in the center of it all—ideal for professionals such as attorneys, architects, therapists, consultants, or anyone seeking a unique live/work opportunity in one of Sarasota’s most desirable locations. Don’t miss your chance to own a piece of Siesta Key Village with unmatched walkability, flexibility, and income-producing potential.
Listing Agent: Kim Donahue (941-724-2587)
2124 CLEMATIS PL, SARASOTA, FL 34239
$2,400,000302 Days on yellowkey MLS ID: A4656371
Bed: 6 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 3574 Built: 2025 Tax: $4,726 (2025)Community: South GateSpa: YesSingle Family
Taxes:$4,726
Remarks: Now presenting a stunning new construction residence in Arlington Park, built by Courtyard Modern Development, where modern design, functionality, and Sarasota luxury lifestyle come together seamlessly. This exceptional two-story home offers 6 bedrooms, 7 full bathrooms, and approximately 3,574 sq ft of living space, thoughtfully designed to deliver both elegance and comfort in every detail. The first level welcomes you with an open-concept layout featuring a spacious living room, dining area, and chef-inspired kitchen, complemented by a walk-in pantry and dedicated laundry room. The primary suite is conveniently located on the main floor, offering privacy and comfort, complete with a large primary bathroom and large walk-in closet. Builder will design a custom closet configuration to reflect the future homeowner's personal needs. An additional guest bedroom with en-suite bath is also located on this level. In addition, enjoy the convenience of a full bathroom that opens to the pool area. The second level features four generously sized bedrooms, each with its own en-suite bathroom and large closets, providing ultimate privacy and convenience for family and guests. Step outside and experience true Florida living with a private pool and spa, expansive outdoor areas including a large covered balcony overlooking the pool, a planned outdoor grill space, perfect for entertaining or relaxing year-round. You will also enjoy the beautifully and thoughtfully designed landscaped yard. Additional features include a 2-car garage and extended driveway. Zoned for the A-rated , this home is ideally located just minutes from Downtown Sarasota, Sarasota Memorial Hospital, Siesta Key Beach, and Southside Village. This is your opportunity to enjoy a home perfectly blending luxury, location, and lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Alberto Rueda Ramirez (701-314-6916)
3711 HIDDEN RIVER RD, SARASOTA, FL 34240
$750,000Listed 04/17/2026 5:14PM MLS ID: A4690484
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2164 Built: 1973 Tax: $5,521 (2025)Community: Hidden RiverSingle Family
Taxes:$5,521
Remarks: A rare opportunity to own nearly 10 acres in one of Sarasota’s most unique aviation communities, offering the ultimate blend of privacy, space, and lifestyle. With direct access to a private airstrip, this property is ideal for aviation enthusiasts seeking the convenience of keeping their aircraft just steps from home. Set on expansive, picturesque land, the property features a private hangar, allowing for seamless fly-in, fly-out access, along with a tennis court and a variety of existing structures including a barn, stable, greenhouse, and additional outbuildings—creating endless possibilities for recreation, storage, or hobby use. The existing 3-bedroom, 2-bathroom block home offers over 2,100 square feet of living space and presents a prime opportunity for a buyer to update, renovate, or reimagine the space to their vision. Being sold as-is, the home provides a strong foundation with solid construction, making it an ideal option for investors or those looking to create a custom estate without starting from scratch. Surrounded by mature trees, natural landscape, and peaceful water views, the setting feels like a private retreat while still being conveniently located to town. Whether you’re looking to restore and personalize the existing home, build your dream estate, or create a private aviation retreat, this property offers a rare combination of land, flexibility, and lifestyle in a highly sought-after location.
Listing Agent: Katie Cobb (913-744-0248)
3247 WOODMONT DR, SARASOTA, FL 34232
$400,000Listed 04/17/2026 4:36PM MLS ID: A4690534
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1186 Built: 1979 Tax: $4,642 (2025)Community: Ridgewood Estates 19Th AddSingle Family
Taxes:$4,642
Remarks: Move-in ready and thoughtfully updated, this Sarasota home offers an open floorplan designed for comfortable everyday living and easy entertaining. The interior features an updated kitchen and bathrooms, along with impact windows and doors for added peace of mind. Recent improvements include a newer roof, updated electrical panel, and new ductwork. Step outside to enjoy the new lanai (2019) overlooking a fully fenced backyard—perfect for relaxing or entertaining. Additional highlights include a large carport with an attached tool shop, providing extra storage and workspace.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Marlin Yoder (941-893-7406)
3458 ANGLIN DR, SARASOTA, FL 34242
$2,595,00056 Days on yellowkey MLS ID: A4683447
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2513 Built: 1983 Tax: $19,659 (2025)Community: Bay Island ParkSpa: NoSingle Family
Taxes:$19,659
Remarks: Welcome to Bay Island, ideally positioned on the north end of Siesta Key, where island living meets exceptional convenience. Just moments from Siesta Beach, Siesta Key Village, and downtown Sarasota’s waterfront dining and cultural offerings—with easy access on and off the island—this elevated Key West-style residence is set across a rare double lot, an uncommon offering on Siesta Key. Fully renovated in late 2019, the home features new siding, roof, electrical, plumbing, irrigation, hurricane-rated windows and French doors, and two HVAC systems. It has since been further enhanced with premium retractable invisible screens on all French doors, kitchen and bath refinements, and a whole-house water filtration system, along with additional upgrades that reflect its continued care and quality. The open-concept floor plan is filled with natural light, highlighted by vaulted ceilings, LVP flooring, and a natural gas fireplace. Multiple covered terraces extend the living space outdoors, reinforcing the home’s relaxed coastal design. The kitchen is designed for both everyday living and entertaining, centered around a large quartzite island with extensive drawer storage and pull-out shelving. A full Thermador appliance package includes a gas range, refrigerator and freezer columns, and dishwasher. Soft-close cabinetry and thoughtful storage solutions provide both function and efficiency. French doors open to an oversized covered deck overlooking mature tropical landscaping. The well-sized owner’s suite is located on the main living level and includes a walk-in closet and a private en-suite bathroom featuring a double vanity and large walk-in shower. A den on this level offers flexibility and can easily serve as a fourth bedroom or home office. Upstairs, two generously sized guest bedrooms share a newly appointed bathroom and enjoy access to a third-level terrace ideal for sunset views. Outdoor living sets this property apart. The double lot creates an expansive backyard with a recently resurfaced pool, travertine decking, and multiple covered terraces—an uncommon offering on Siesta Key. The additional lot provides flexibility for future enhancements while preserving privacy and open space.
Listing Agent: Barbara May (404-822-9264)
435 S GULFSTREAM AVE #1103, SARASOTA, FL 34236
$665,00011 Days on yellowkey MLS ID: A4688618
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1424 Built: 1972 Tax: $8,550 (2025)Community: Regency HouseSpa: NoCondo
Taxes:$8,550
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Elevated Penthouse Living With Breath Taking Views: Skip the renovations and some carrying costs?1 Year of Condo Fees will be paid by the Seller. This 11th-floor Penthouse-level gem at Regency House is officially "The One." Spanning 1,424 sq. ft. of bright, open space, this 2-bedroom, 2-bathroom residence trades dark corners for floor-to-ceiling glass that frames Sarasota Bay and the Ringling Bridge like a living gallery. The interior experience aesthetic is a clean neutral palette and move-in ready, a décor style that will easily adapt to a range of styles. The designer kitchen featuring custom cabinetry and stone surfaces flows effortlessly into an open-concept living area anchored by a custom electric fireplace, perfect for sunset hosting. Retreat to a large primary suite designed to entice you with tranquil water views, complemented by gorgeous, updated bathrooms and the convenience of a new in-unit washer and dryer. Total Maintenance-Free living: 24-hour concierge service, dedicated parking, and additional storage closet within the unit included. Enjoy a World-Class Lifestyle where you are perfectly positioned at the quiet edge of downtown Sarasota. Enjoy immediate proximity to Marina Jack and a short stroll to the boutiques of Palm Avenue, the Opera, Theatre, Whole Foods, and the botanical beauty of Selby Gardens. Whether it's a morning walk through Bayfront Park or a quick drive over the bridge to St. Armand's Circle and Lido Beach, the best of the Gulf Coast is quite literally at your doorstep. Celebrate ease of ownership and Peace of Mind; In an era where buyers are cautious about condo buildings, Regency House stands apart as a solid choice. This building has completed the Milestone Inspection / SIR Study and maintains healthy reserves. To make your transition entirely frictionless; 1 Year of Condo Fees and Special Assessment for the Upgraded Pool will be paid in full by the seller with acceptable offer.
Listing Agent: Dave Hall (646-256-6524)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,000Listed 04/17/2026 9:36AM MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Drew Jacobsen (941-253-6309)
5047 VINSON WAY, SARASOTA, FL 34232
$549,0003 Days on yellowkey MLS ID: A4689764
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 1980 Tax: $4,521 (2025)Community: Brentwood EstatesSpa: YesSingle Family
Taxes:$4,521
Remarks: Exceptional income-producing turnkey opportunity in the heart of Sarasota with a 9.8% cap rate! This versatile property at 5047 Vinson Way is ideal for both investors and owner-occupants looking to maximize returns while enjoying a primary residence. The property is thoughtfully configured into three separate units: a spacious 2-bedroom, 1-bath main residence perfect for an owner, plus two additional income-generating units—a studio and a one-bedroom—both currently operating as successful short-term rentals. The outdoor space is a true standout, featuring a brand-new pool and spa, creating a resort-style experience that significantly enhances rental appeal and guest satisfaction. Each unit offers privacy and functionality, making it ideal for Airbnb or extended stays. Whether you’re house hacking or running a full investment property, this setup delivers immediate income potential and strong cash flow. Located in a desirable Sarasota area close to shopping, dining, and world-famous beaches, this property blends lifestyle and performance seamlessly. Live in one unit, rent the others, and capitalize on a high-performing asset—opportunities like this are rare.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Mariele Hoffman (941-225-0800)
480 CLEVELAND DR, SARASOTA, FL 34236
$4,100,000149 Days on yellowkey MLS ID: A4672676
REDUCED by $400,000 (8.9%) on 04/17/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2875 Built: 1967 Tax: $47,931 (2024)Community: Lido BeachSingle Family
Taxes:$47,931
Remarks: Boater's Delight on Lido Key. Beautiful Home with 3 Bedrooms, 3.5 Baths on a Beautiful, Wide, Private, Deep Water Canal with a Dock with Electric and a Partial View of the Bay. No Bridges to the Bay. Rear of Home has a Southern Exposure with a Lovely Heated Pool and an Enchanting Covered Patio for Entertaining with Serene Water Views. Only Two Blocks from Beautiful Lido Beach. Walk to Trendy St. Armands Circle to Shop and Dine. Discover a rare Lido Key sanctuary offering direct, bridge-free boating to the Gulf of Mexico and a private waterfront pool. Perfectly positioned along the bay and sold fully furnished, this home delivers effortless luxury with immediate access to open water, serene outdoor living, and one of Sarasota’s most desirable island lifestyles. Designed to embrace its waterfront setting, the expansive living areas open seamlessly to the outdoors. Six sets of sliding glass doors frame tranquil water views and create a fluid connection to the screened-in waterfront heated pool and expansive paver deck, ideal for both entertaining and everyday relaxation. From poolside lounging to sunset evenings by the water, the outdoor spaces flow directly to the private expanded dock with lift, complete with power and water, allowing you to reach the Intracoastal and Gulf of Mexico within minutes—with no bridges to navigate. You’ll love the peacefulness of the canal right at your doorstep. Inside everything has been renovated and updated in 2025! The kitchen is both elegant and functional, featuring stainless steel appliances, a built-in microwave, floating shelves, generous cabinetry, and a thoughtfully placed pantry adjacent to the laundry room, which includes a utility sink. Porcelain tile flooring runs consistently throughout the entire home, enhancing the clean, sophisticated aesthetic and open feel of the living spaces. The private living quarters are thoughtfully arranged for comfort and flexibility. A bedroom located at the front of the home offers an ideal guest retreat, while a beautifully designed office or den welcomes you upon entry, highlighted by three bay windows that fill the space with natural light. This office/den is enclosed with French doors, making it an ideal flex space for working from home, a media room, or additional entertaining. The primary suite is a true sanctuary, complete with custom his-and-her closets and a spa-inspired bathroom featuring floor-to-ceiling tile, a glass-enclosed shower, and plantation shutters. A conveniently located half bath enhances functionality for guests and gatherings. Outside your door, enjoy the quiet, walkable streets of Lido Key, offering a peaceful residential atmosphere. Explore nearby nature trails and kayak launches, stroll to St. Armands Circle, or take a short drive over the Ringling Bridge to Downtown Sarasota for world-class cultural offerings, fine dining, and shopping. With its luxury waterfront setting, private pool, direct Gulf boating access, and full furnishings included, this Lido Key residence offers a rare opportunity to own a timeless coastal retreat where every detail supports a lifestyle of ease, elegance, and exclusivity. Schedule your private showing and experience this exceptional waterfront offering firsthand.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
1931 HIGH POINT CIR, SARASOTA, FL 34236
$1,495,000Listed 04/17/2026 1:50PM MLS ID: A4690458
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1712 Built: 1940 Tax: $13,413 (2025)Community: Hudson BayouSpa: NoSingle Family
Taxes:$13,413
Remarks: Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an oversized lot. The interior features refinished hardwood floors, double-paned windows, and an updated kitchen equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a trey ceiling and a gas fireplace, with French doors leading to a private outdoor area, perfect for the Florida lifestyle. This exterior retreat includes a saltwater pool and a professionally landscaped, fully fenced yard with irrigation supported by an irrigation well. Significant improvements offer peace of mind and long-term value, including a new standing seam metal roof (2025), a full A/C system (2022), a garage mini-split (2024), and completely replumbed with PVC. The air-conditioned two-car garage features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. The property has a great rental history.
Listing Agent: Fred Sassen (404-408-5956)
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