Location: Sarasota , 34231
Do Not Show Listings
3205 GOLDEN EAGLE LN, SARASOTA, FL 34231
$322,500166 Days on yellowkey MLS ID: A4677694
REDUCED by $2,500 (0.8%) on 06/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1268 Built: 1984Monthly Fee: $333 Tax: $2,156 (2025)Community: Eagle ChaseVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,156
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: PRICE IMPROVEMENT! Eagle Chase Villa – Sarasota. Ideally positioned in the desirable Eagle Chase community, this impeccably upgraded 2-bedroom, 2-bath villa offers 1,268 square feet of thoughtfully enhanced living space just minutes from beaches, nature, shopping, and downtown Sarasota. Located within walking distance to the 84-acre Red Bug Slough Nature Preserve and only 2.1 miles to Crescent Beach and 3 miles to Siesta Key, this home delivers the perfect blend of location, quality, and peace of mind. Inside, the residence reflects years of careful investment and pride of ownership, with over $125,000 in renovations and improvements completed since 2020. The home has undergone extensive mechanical and structural upgrades, including a near full plumbing re-pipe with the removal of old cast iron and replacement with CPVC, new electrical breakers, all-new outlets, plate covers, and modern dimmable LED lighting throughout. HVAC systems have been replaced and professionally serviced twice yearly, the roof was replaced in 2022, and impact-rated windows and doors were installed for comfort, efficiency, and storm protection. The kitchen has been beautifully updated with quartz countertops, painted cabinetry with new hardware, tile backsplash, LED under-cabinet lighting, an upgraded oven range, undermount sink, and newer appliances, creating a bright and functional space that flows effortlessly into the living areas. Both bathrooms were fully remodeled down to the studs with waterproofing, new drain lines, Moen fixtures, custom tile, rain shower heads, quartz vanities, beveled window detail in the primary bath, and LED lighting with dimmers, offering a spa-like experience. Living space was thoughtfully expanded with the creation of a stunning Florida Room, replacing the former lanai and deck. This space features impact sliding doors and windows, reinforced flooring, custom Italian tile, fresh paint, updated electrical, and a ceiling fan with remote, seamlessly blending indoor and outdoor living. New composite decking was added on a reinforced foundation along the rear of the home, with additional composite decking on the side porch, while the exterior rear stucco wall was repainted for a polished finish. Additional enhancements include plantation shutter doors throughout the hallways, bedrooms, and primary bath, refreshed interior doors and hardware, updated flooring in the primary bedroom, attic flooring for storage, and a mounted 65" Sony flat-screen TV with in-wall wiring that will convey. The home has also been meticulously maintained with comprehensive termite prevention, Sentricon bait systems, and ongoing annual inspections showing zero termite activity. Outside, the property has been transformed into a serene, park-like setting with engineered paver stone retaining walls designed to enhance drainage, extensive hardscape and landscaping improvements, indigenous Florida plantings, fruit trees, pollinator-friendly gardens, and low-maintenance decorative stone features. The location offers exceptional convenience with nearby shopping, easy access to I-75, downtown Sarasota, Venice, St. Petersburg, Tampa, and Clearwater, making this home ideal as a primary residence or refined coastal retreat. This Eagle Chase villa stands apart for its depth of upgrades, quality craftsmanship, and unmatched proximity to Sarasota’s best natural and coastal amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Susan Hill (603-479-8368)
2948 CLARK RD #121, SARASOTA, FL 34231
$155,00025 Days on yellowkey MLS ID: A4691902
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 888 Built: 1973 Tax: $2,139 (2025)Community: Trinity VillageSpa: NoCondo
Taxes:$2,139
Remarks: Welcome to Trinity Village — the best value currently available in the community! This beautifully updated 2-bedroom, 2-bath condo offers 888 SQFT of comfortable living space and stands out as the most affordable opportunity on the market in Trinity Village. Freshly painted and thoughtfully improved for today’s buyer, this move-in ready unit features new impact windows, updated ceiling fans, modern lighting, and upgraded electrical throughout for added style, comfort, and peace of mind. Previously used as a successful investment property, the condo has consistently generated between $1,500–$1,750 a month in annual rental income, making it an excellent option for both investors and owner-occupants alike. Residents of Trinity Village enjoy low HOA fees and an unbeatable location directly across the street from grocery stores, restaurants, shopping, and everyday conveniences. Plus, you’re only a short bike ride away from the world-famous Siesta Key beaches.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Kevin Bruinsma (616-308-7965)
7860 HOLIDAY DR, SARASOTA, FL 34231
$950,00059 Days on yellowkey MLS ID: A4691644
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2196 Built: 1957 Tax: $7,241 (2025)Community: Holiday HarborSingle Family
Taxes:$7,241
Remarks: Wonderfully charming street along HIDDEN HARBOR MARINA high and dry this lovely turn key home has 3 beds and 2.5 baths, a heated pool and large fenced yard.. NO HOA Country restrictions only Sarasota County restrictions. Home has many updates including a light and bright kitchen, window treatments, a king bed en-suite bath with French doors to a covered patio with plenty of lounging furniture and TV set up. This home comes turnkey furnished and has IMPACT RESISTANT, ENERGY EFFICIENT WINDOWS AND SLIDERS and a newer metal roof. You will love this HIDDEN HARBOR neighborhood with plenty of charm. Minutes to Siesta Key shopping and dining. A new shopping area to be completed by 2026 includes a new WHOLE FOODS and TRADER JOES as well as shopping and dining.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Marianne Lebar (941-650-0337)
6735 KEYSTONE DR, SARASOTA, FL 34231
$510,000130 Days on yellowkey MLS ID: TB8475997
REDUCED by $5,000 (1.0%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1659 Built: 1969 Tax: $2,026 (2025)Community: Gulf GateSingle Family
Taxes:$2,026
Elementary School: None
High School: None
Middle School: None
Remarks: Prepare to be impressed. This fully remodeled Gulf Gate gem is a rare opportunity, offering 1,659 square feet of beautifully reimagined living space where luxury meets everyday comfort. From the moment you step inside, you’re welcomed by a bright, open-concept layout designed for modern living and effortless entertaining. Expansive sliding glass doors lead to a spacious screened-in lanai, seamlessly blending indoor and outdoor living — the perfect setting for morning coffee, weekend gatherings, or relaxing evenings. The brand-new custom kitchen is truly the heart of the home, featuring two-tone solid wood cabinetry, elegant quartz countertops, a marble backsplash, and new GE stainless-steel appliances. Every finish was thoughtfully selected to create a refined yet inviting space. The primary suite offers a peaceful retreat with a walk-in closet and a spa-inspired ensuite bathroom complete with a new double vanity, designer tile shower, and upgraded fixtures as well as a dedicated recirc pump for near instant hot water. Throughout the home, new luxury vinyl plank flooring, fresh interior paint, modern lighting, ceiling fans, and new interior doors create a clean, contemporary coastal feel. Major upgrades provide peace of mind for years to come, including a new shingle roof (2026), new HVAC system (2026), new electric panel (2026), new insulation (2026), Water Heater(2026) and fully replumbed drains and supply lines. Additional highlights include a large indoor laundry room with a custom boot bench, a two-car garage, and a triple-wide driveway offering ample parking. Outside, you’ll appreciate one of the home’s most unique and practical features — a beautifully landscaped, low-maintenance front yard with no grass to mow. As one of the only homes in the neighborhood designed this way, it offers enhanced curb appeal while significantly reducing upkeep and water usage. Just moments to Siesta Key’s sugar-white sands, this Gulf Gate home offers unmatched convenience — walk to A-rated Gulf Gate Elementary, 5 min to Costco, and a dynamic redevelopment of the former Sarasota Square Mall into a vibrant new retail, dining, and residential hub. This is modern coastal living at its finest — move-in ready and designed to impress. The final image is a rendering of what the backyard could be ( at 37 foot deep and 80 feet wide ) there is plenty of room to add a pool/outdoor kitchen. Buyer’s agent to verify all MLS information including room sizes, utilities, and HOA (if applicable).
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Joseph Trupiano, Iii (813-765-6970)
2227-2229 MONTCLAIR DR #1&2, SARASOTA, FL 34231
$800,000171 Days on yellowkey MLS ID: A4677183
REDUCED by $25,000 (3.0%) on 05/06/2026
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2118 Built: 1970 Tax: $7,681 (2025)Community: Monticello Unit 1Spa: NoApartment
Taxes:$7,681
Elementary School: Phillippi Shores Elementary
Remarks: This nicely updated two-unit duplex in the desirable Phillippe Gardens community on Coquina Island offers excellent income potential in a highly sought-after location. Situated on a generous corner lot, each unit features 3 bedrooms and 2 bathrooms, including a private primary bath, along with a newer eat-in kitchen that flows seamlessly into the living room. UPDATES INCLUDE- 3 NEW BATHROOMS, NEW QUARTZ COUNTERTOPS, NEW FLOORS, NEW GARAGE DOORS. Both units include a private backyard, an attached garage, and the convenience of a large side drive with ample parking. The property is ideally located just 10 minutes from Siesta Key Beach, 12 minutes from Siesta Key Village, and less than 20 minutes from major shopping, downtown Sarasota, and top local attractions. With easy access to US-41, waterfront dining, vibrant nightlife, and award-winning Gulf beaches, this turn-key duplex is perfectly positioned for strong rental demand. Priced to sell, it presents a rare opportunity for investors seeking a ready-to-go property in an exceptional Sarasota location.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Lisa Sanders (773-398-0378)
1612 STICKNEY POINT RD #1612-1, SARASOTA, FL 34231
$274,90081 Days on yellowkey MLS ID: A4688336
0 Days Off yellowkey (back on 6/20/2026)
REDUCED by $15,000 (5.2%) on 06/11/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 872 Built: 1975Monthly Fee: $919 Tax: $2,989 (2025)Community: Castel Del MareCondo
Taxes:$2,989
Remarks: PRICE CHANGE!!! AMAZING OPPOTUNITY TO OWN THIS COMPLETED REMODELED 1 BEDROOM/1 BATH CONDO IN CASTEL DEL MARE WHICH HAS BEEN NICKNAMED THE "HIDDEN JEWEL ON THE BAY" BECAUSE OF ITS DESIRABLE LOCATION WHICH SERVES AS THE GATEWAY TO SIESTA KEY. LOCATED JUSTH SOUTH OF THE DRAWBRIDGE TO SIESTA KEY, YOU CAN WALK, BIKE OR DRIVE RIGHT OVER THE BRIGE AND BE AT THE AMAZING BEACHES, RESTAURANTS, AND SHOPPING VENUES. THIS STUNNING CONDO HAS BEEN COMPLETELY UPDATED. THE KITCHEN BOASTS AN OPEN-CONCEPT WITH GRANITE COUNTERTOPS, PENDANT AND OVER CABINET LIGHTING. A LARGE ISLAND OPENS INTO A SPACIOUS LIVING AREA WHICH FEATURES CROWN MOLDING AND WAINSCOTING. THE LANAI HAS BEEN FINISHED TO CREATE EXTRA LIVING SPACE WITH A HUGE WAL-IN CLOSET. THE MASTER BEDROOM HAS A BUILT-IN CLOSET AND A FULL WALK-IN CLOSET WITH BUILT-IN CABINET AND COUNTERTOP ALLOWING PLENTY OF EXTRA STORAGE. THE BATHROOM HAS BEEN COMPLETELY REMODELED WITH BEAUTIFUL TILED WALK-IN SHOWER. THE UNIT HAS A TANKLESS WATER HEATER (2023) AND A NEW AIR CONDITIONING SYSTEM (2021). THIS CONDO IS TURN-KEY FURNISHED SO IT A GREAT PLACE TO CALL IT A VACATION GET-A-WAY OR HOME! (LIVING ROOM FAN TO BE REPLACED)
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Linda Ren (941-928-1393)
2110 PALM TER, SARASOTA, FL 34231
$469,7777 Days on yellowkey MLS ID: A4697614
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1680 Built: 1952 Tax: $3,664 (2025)Community: Harbor OaksApartment
Taxes:$3,664
Middle School: Sarasota Middle
Remarks: Excellent opportunity to own a well-maintained duplex in a highly desirable Sarasota location just minutes from world-famous Siesta Key Beach, Downtown Sarasota, shopping, dining, and transit. This property features two separate 2-bedroom, 1-bathroom units, making it ideal for investors seeking strong rental income or owner-occupants looking to offset their mortgage with rental revenue. Both entrances have enclosed lanai areas. The front unit lanai has laundry hookups. Tile flooring throughout, large kitchens, tub with tiled shower walls. Ceiling fans in bedrooms. Fenced on back and side of building. Both units offer comfortable floor plans with central air conditioning and charming fireplaces that add character and appeal. The rear unit includes a valuable two-car carport, dedicated storage area, and laundry hookups, providing additional convenience for tenants. 2011 Metal Roof, 2021 & 2022 HVAC. Owner pays water, electric separately metered. Attractive units and setup for long-term renters. Situated on a quiet street with easy access to Sarasota's beaches, cultural attractions, restaurants, and everyday conveniences, this duplex combines location, functionality, and investment potential. Buyer to verify all measurements, rental information, and property details.
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Dane Peterson (239-357-5692)
6448 HOLLYWOOD BLVD, SARASOTA, FL 34231
$3,995,0007 Days on yellowkey MLS ID: A4697076
0 Days Off yellowkey (back on 6/19/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4055 Built: 1991 Tax: $15,348 (2025)Community: Pine Shores Estate 7Th SecSpa: YesSingle Family
Taxes:$15,348
Remarks: Under contract-accepting backup offers. Exceptional waterfront living awaits in this extensively updated three-story Intracoastal estate offering 113 feet of deep-water frontage, no fixed bridges to the Gulf, and less than one mile to world-renowned Siesta Key Beach. Designed for both luxury and lifestyle, this 4-bedroom, 4.5-bath residence encompasses 4,055 air-conditioned square feet and 6,129 total square feet of thoughtfully curated living space. A boater's dream, the property features a new 20,000-pound boat lift, 113 feet of new Trex dock, and a 7,000-pound double jet ski lift with direct access to Sarasota Bay and the Gulf of Mexico. The resort-style outdoor environment has been transformed with more than $250,000 in professional landscaping by Plant Source, featuring lush tropical gardens, bamboo privacy hedges, coconut and royal palms, premium turf, a propane fire pit, tiki torches, a sparkling pool, and multiple spaces for waterfront entertaining. A custom dual-entry metal privacy gate provides a grand and private arrival. Inside, the residence showcases engineered hardwood flooring throughout, impact-rated windows and doors, remote-controlled blinds, a whole-home water purification system, and a private elevator servicing all three levels. The recently redesigned kitchen and interior spaces were professionally reimagined by Mindy Webb Design & Blu Interiors, blending timeless coastal elegance with modern luxury. The first floor offers a three-car garage, gym, recreation room or office, and hurricane-rated sliding glass doors opening to the pool and waterfront living areas. The second floor serves as the heart of the home with expansive gathering spaces and an outdoor lounge area ideal for enjoying Sarasota's year-round sunshine. Occupying the top level, the private primary suite features a waterfront balcony with breathtaking Intracoastal and sunset views, creating the ultimate owner's retreat. Adding flexibility and value is a detached pool house complete with a new metal roof, impact windows and doors, and its own mini-split system. Comfort is ensured throughout the property with three separate air-conditioning systems serving the main residence, plus additional mini-splits in the gym and auxiliary spaces. Ideally located just over the South Siesta Key Bridge, this exceptional waterfront estate offers a rare combination of deep-water boating, designer renovations, resort-style outdoor living, and convenient access to Siesta Key Beach, dining, shopping, and all that Sarasota has to offer.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
1648 IDLE LN, SARASOTA, FL 34231
$575,000148 Days on yellowkey MLS ID: A4680338
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1388 Built: 1962 Tax: $4,744 (2025)Community: Plaza GardensSingle Family
Taxes:$4,744
Remarks: Just a half mile from the world famous Siesta Key Beach, this charming mid century ranch sits quietly tucked within a peaceful, private neighborhood on the mainland. Offering an effortless coastal lifestyle, this beautifully cared for 2 bedroom, 2 bath home features an open layout, a bright and expansive air conditioned sunroom, and a 1 car garage. It’s being offered turnkey furnished, making it an ideal choice for a full time residence, a vacation retreat, or a strong investment opportunity. With 1,388 square feet of cooled living space plus an additional 232-square foot laundry and utility room, the home feels spacious and inviting. The large glass enclosed Florida room is a standout feature, filled with natural light from oversized windows and overlooking a tranquil, thoughtfully landscaped backyard. Recent improvements include a 2023 roof, updated windows, a newer septic system and lift station, upgraded electrical service, polished terrazzo flooring throughout, and a paver driveway. The effective year built is 1997, reflecting the extensive updates. Surrounded by multi-million-dollar properties and located less than a mile from the vibrant shops and restaurants of Gulf Gate, this home offers the perfect blend of privacy, convenience, and coastal living. Watersports, dining, and the soft white sands of Siesta Key Beach are all just moments away. Come experience the lifestyle this special property offers.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mike Pilarczyk (319-321-5348)
4820 KESTRAL PARK CIR #18, SARASOTA, FL 34231
$499,00035 Days on yellowkey MLS ID: A4694438
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1570 Built: 1982 Tax: $5,710 (2025)Community: Landings Carriagehouse IiCondo
Taxes:$5,710
Remarks: Welcome to one of The Landings' best-kept secrets. Tucked inside the intimate Carriage House community, this 2-bedroom, 2-bath plus spacious den residence delivers the feel of a single-family home wrapped in the ease of maintenance-free living and its move-in ready. Inside, tile flooring flows throughout, anchoring a bright, open layout that feels larger than its footprint suggests. The updated kitchen impresses with a modern aesthetic, solid surface counters, and finishes that feel fresh and intentional, not dated. Both bathrooms have been thoughtfully remodeled, featuring solid surface counters and elegant tile enclosures. A wood-burning fireplace adds warmth and character, making this home as livable as it is lovely. The very spacious den offers the flexibility to serve as a home office, guest room, or hobby space, whatever your lifestyle calls for. An additional den space provides even more room to spread out, work, or create. Your private one-car garage sits just beyond a charming paver driveway shared with only one neighbor — a quiet, neighborly setup that feels nothing like a typical condo. When it comes to outdoor living, this home truly delivers: an expansive screened-in patio sets the stage for year-round enjoyment, while a separate open-air patio offers a sun-drenched spot to relax, garden, or simply soak in the Florida lifestyle. Peace of mind comes standard: a brand-new 2026 roof means this home is as solid as it is stylish. Offered unfurnished and ready for immediate occupancy. Residents of Carriage House II enjoy access to a beautiful pool and clubhouse, all set amid lush, manicured grounds surrounding a tranquil lake with fountains, turtles, and ducks. Membership to The Landings Racquet Club is available but not included or required — a wonderful option for those who want the full lifestyle package. The Landings' coveted location west of the Trail puts everything within easy reach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
6470 HOLLYWOOD BLVD #208, SARASOTA, FL 34231
$320,00017 Days on yellowkey MLS ID: A4696425
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 910 Built: 1978 Tax: $3,022 (2025)Community: Almeria On The BayCondo
Taxes:$3,022
Remarks: Updated waterfront condo just a short stroll to Crescent Beach and the fun and funky South Siesta Key Village! A Five-minute drive or trolley ride to the main Siesta Village. Lounge by the heated pool or pull your boat up to this nicely remodeled 2 bedroom/2 bath Almeria by the Bay unit. Located on the 2nd floor (with an elevator) , this unit boasts a coastal kitchen with a convenient breakfast bar, new luxury vinyl floors (2026), and amazing Intercoastal water views from the primary bedroom and screened lanai. Both bathrooms have been thoughtfully updated, and this unit is being offered turn-key furnished. It features a Beachy décor throughout. Fish or Kayak right from your own complex ! Monthly rentals are allowed and sought after. There's also a large, private storage area. Whether it is a forever home, vacation get-away or investment property, this is one of the most affordable move-in ready units located so close to the beach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Donna Portale (716-308-8189)
6723 AVENUE C, SARASOTA, FL 34231
$1,949,000144 Days on yellowkey MLS ID: C7521189
REDUCED by $50,000 (2.5%) on 06/19/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1851 Built: 1999 Tax: $5,412 (2025)Community: Bay View AcresSingle Family
Taxes:$5,412
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: Location, location, location! Siesta Key - Private Boat Slip - Completely Updated - NOT in a FLOOD ZONE & No Hurricane damage!! Situated on Avenue C just before the South Siesta Key Bridge, this beautifully updated home offers an unbeatable coastal lifestyle. Enjoy less than a mile walk to the world-famous Siesta Key Beach, where you can take in stunning sunsets, white sand beaches, and relaxing weekends by the water. Boaters will love the easy access to the Intracoastal, just minutes away, with approximately 15 minutes to reach the Gulf of America. The home is also within walking distance to local restaurants and beaches, while being tucked inside a peaceful bird sanctuary, offering a rare blend of convenience and natural surroundings. Inside, the home has been fully updated. Improvements completed in 2020 include a NEW ROOF, tile flooring throughout, a brand-new kitchen, and updated bathrooms. The floor plan offers three bedrooms, including a SECOND PRIMARY SUITE, three bathrooms, and an oversized two-car garage. The backyard is designed for true Florida living, featuring a large heated pool, a spacious lanai with new panoramic screening, and a PRIVATE BOAT SLIP, one of only two slips in the entire neighborhood. The pool was resurfaced with new tile in 2025, and the dock was completed in 2025 as well. This home captures the best of coastal Florida living with walkability, boating access, and thoughtful updates throughout. Enjoy the neighborhood with a short walk to popular spots including Daiquiri Deck, Siesta Key Oyster Bar, Captain Curt’s Crab & Oyster Bar, The Old Salty Dog, Abel's ice cream, Ruth’s Chris Steak House, and Carrabba’s Italian Grill. With Publix Super Market and shopping just down the road, you can enjoy peace and quiet while still being close to everything you need. Schedule your own personal tour today!
Listing is courtesy of: SELLSTATE VISION REALTY (941-336-5400)
Listing Agent: Savannah Zarris (941-807-4304)
1630 STICKNEY POINT RD #101, SARASOTA, FL 34231
$269,90094 Days on yellowkey MLS ID: A4687288
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1975 Tax: $2,758 (2025)Community: Castle Del MareCondo
Taxes:$2,758
Remarks: Fantastic opportunity to own a beautifully updated 1BR/1BA first-floor unit in highly desirable Castel Del Mare! This light and bright residence features a tiled entry and kitchen, with attractive laminate flooring throughout the remaining living areas. The spacious kitchen is equipped with white cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. The generously sized primary suite offers a private, updated en-suite bath complete with granite counters and a walk-in shower. What truly sets this unit apart is the in-unit washer and dryer—a rare convenience—along with an expansive double, oversized lanai just steps from the pool, creating the perfect space to relax and enjoy the Florida lifestyle. Castel Del Mare is a sought-after waterfront community ideally located just steps from the South Bridge to Siesta Key—offering the best of both worlds with easy access to the beach while enjoying the convenience of mainland living.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
4304 MIDLAND RD, SARASOTA, FL 34231
$340,00058 Days on yellowkey MLS ID: TB8502989
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $34,900 (9.3%) on 05/26/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1447 Built: 1952 Tax: $3,143 (2025)Community: Floral Park HomesteadsSpa: YesSingle Family
Taxes:$3,143
Elementary School: Wilkinson Elementary
Remarks: This meticulously maintained 3-bedroom residence offers the ideal blend of vintage Florida character and high-quality contemporary improvements—all in a prime Sarasota location. Metal roof (2011), new HVAC system (2023), and tankless water heater (2020). Original wall planking replaced with new Sheetrock and insulation to improve energy efficiency. New flooring installed in 2020 flows throughout the open-concept living areas. Private fenced backyard with a sparkling pool (2019) and an above-ground heated spa—perfect for year-round enjoyment. Conveniently situated near Sarasota’s most desirable destinations. Approximately 5 miles to the world-renowned Siesta Key Beach; it is also close to Lido Key Beach. Minutes to St. Armands Circle and Downtown Sarasota’s vibrant restaurant and cultural scene. Near major retailers, grocery stores, and the shops along Bee Ridge Road and Southside Village. Just around the corner from Bee Ridge Park with green space, playgrounds, and community activities.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Brenda Olivas (407-280-0208)
2227 CIRCLEWOOD DR #52, SARASOTA, FL 34231
$289,90022 Days on yellowkey MLS ID: A4696035
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1974 Tax: $1,597 (2025)Community: Woodside VillageSpa: YesVilla
Taxes:$1,597
Remarks: Recently extensively remodeled villa just minutes from Siesta Key, surrounded by mature Old Florida landscaping in a private enclave of villa-style condos, close to Gulf Gate and US41. This inviting 2-bedroom, 2-bath condominium unit in Sarasota’s desirable Gulf Gate area, blending classic Florida charm with modern comfort. The spacious layout includes a bright Florida room, rear screened porch, and a covered carport. Recent updates feature a new modern kitchen w/ stainless steel appliances, new textured/painted ceilings and walls, newer HVAC system, newer electric wiring throughout the unit, newer electric panel, and newer water heater, plus newly paved neighborhood roads. The community offers a tennis/pickleball court and a large screened-in heated swimming pool. Not in a flood zone requiring insurance, this home is available for immediate occupancy, perfect for seasonal or year-round living. Just a 5-minute drive to world-famous Siesta Key Beach and close to shopping, dining, and entertainment, it’s ideal as a permanent home, vacation retreat, or investment property.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
208 SOUTHWINDS DR, SARASOTA, FL 34231
$64,90066 Days on yellowkey MLS ID: A4690882
4 Days Off yellowkey (back on 6/19/2026)
REDUCED by $10,000 (13.4%) on 05/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 459 Built: 1966Monthly Fee: $195 Tax: $1,160 (2025)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,160
Remarks: Under contract-accepting backup offers. Welcome to an incredible opportunity in the highly desirable Southwind's 55+ co-op community, ideally located in the heart of Sarasota just minutes from the world-renowned Siesta Key Beach. Whether you’re searching for a full-time residence, seasonal getaway, or investment opportunity, this property offers exceptional value in an unbeatable location. This one-bedroom, one-bath residence features a spacious and functional layout with abundant natural light throughout. The living area flows nicely, creating a comfortable and inviting space to relax or entertain. One of the standout features is the oversized lanai; perfect for enjoying the Florida lifestyle year-round and easily serving as additional living space. The home also offers a private driveway, a dedicated laundry area located in the shed, and ample storage space. While the unit could benefit from some updating, it is priced accordingly, presenting a fantastic opportunity to customize and make it your own. With a little vision, this property has the potential to truly shine; making it especially appealing for investors or buyers looking to add value. Located in an X flood zone, this property has had no flood or water damage from recent storms, offering added peace of mind. Southwind is a vibrant and friendly community known for its active lifestyle and impressive amenities, including a heated pool, shuffleboard courts, horseshoe pits, library, and recreation hall. The community also offers guest parking along with designated areas for RV and boat storage. With low monthly fees of just $195, which include water, sewer, cable, and lawn care, it’s one of the best values in Sarasota. Conveniently located just 10 minutes to Siesta Key, 20 minutes to downtown Sarasota and UTC Mall, and close to shopping, dining, and everything South Sarasota has to offer. Affordable opportunities like this in such a prime location are rare. Priced to sell and offered as-is with the right to inspect; don’t miss your chance to make this your own slice of paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
3225 GULF WATCH CT, SARASOTA, FL 34231
$399,0008 Days on yellowkey MLS ID: TB8519650
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1216 Built: 1990Monthly Fee: $133 Tax: $3,345 (2025)Community: Gulf Gate GlenSingle Family
Taxes:$3,345
Remarks: Nestled within the desirable Gulf Gate Glen community, this location offers the perfect blend of convenience, recreation, and the laid-back Florida lifestyle that makes Sarasota so sought after. Residents enjoy being just minutes from the powder-soft sands of Siesta Key Beach, consistently ranked among the best beaches in the country. Whether you're spending the day boating on Sarasota Bay, exploring nearby waterfront parks, or taking in a breathtaking Gulf Coast sunset, this location places the very best of Sarasota right at your fingertips while remaining outside of a flood zone. Stepping inside, you'll immediately notice the soaring vaulted ceilings, abundant natural light, and luxury vinyl plank flooring that flows throughout the home. This well-designed floorplan offers 2 bedrooms, 2 bathrooms, and a spacious 2-car garage, creating the perfect balance of comfort and functionality. The kitchen features stainless steel appliances and overlooks a dining area, making everyday living and entertaining effortless. The owner's suite serves as a private retreat with a walk-in closet and an ensuite bathroom complete with dual sinks and a walk-in shower. French doors lead to the screened-in lanai, providing the ideal space to enjoy your morning coffee, unwind in the evenings, or entertain guests while enjoying Florida's year-round sunshine. One of the biggest advantages of living here is the everyday convenience. Gulf Gate Village is just around the corner, offering an eclectic mix of locally owned restaurants, coffee shops, bakeries, live music venues, and neighborhood bars that create a true sense of community. For shopping, dining, and entertainment, you're only a short drive from Downtown Sarasota, St. Armands Circle, and the countless cultural attractions that make Sarasota one of Florida's premier destinations. Outdoor enthusiasts will appreciate easy access to Legacy Trail, one of the area's most popular biking and walking trails stretching for miles throughout Sarasota County. Nearby parks, marinas, fishing spots, kayak launches, golf courses, tennis facilities, pickleball courts, and fitness centers provide endless opportunities to enjoy an active Florida lifestyle. Families will appreciate the proximity to highly regarded schools, while commuters benefit from quick access to US-41, making travel throughout Sarasota, Venice, and Lakewood Ranch simple and convenient. Sarasota Memorial Hospital, medical offices, grocery stores, and everyday necessities are all just minutes away. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional Sarasota location delivers the coastal lifestyle buyers dream about. Close to world-famous beaches, vibrant dining and entertainment, outdoor recreation, and everything that makes Florida's Gulf Coast so special, schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Bona Nedelkovska (727-238-6302)
5720 ISANDA PL, SARASOTA, FL 34231
$785,00029 Days on yellowkey MLS ID: A4695097
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1971 Built: 1967 Tax: $5,994 (2025)Community: Phillippi Gardens 03Spa: NoSingle Family
Taxes:$5,994
Remarks: Welcome to your private piece of paradise! Situated on an expansive, oversized lot featuring a massive, fully fenced side yard, this masterfully renovated 4-bedroom, 2-bathroom residence perfectly blends modern luxury with an outdoor vacation lifestyle. From the moment you step through the beautiful front entrance into the large, welcoming foyer, the quality of craftsmanship is undeniable. The entire home features seamless, high-end wood-plank tile flooring that leads you into a show-stopping chef's kitchen. the kitchen is anchored by stunning quartz countertops with a dramatic waterfall edge, pristine white cabinetry, a modern tile backsplash, premium stainless steel appliances, and a convenient breakfast bar. The spacious owner's retreat is a true "wow" factor, boasting a spa-like bathroom complete with a custom walk-in shower, a deep soaking tub, and gorgeous wood-plank accent walls. Both bathrooms throughout the home have been meticulously updated with newer vanities, quartz countertops, and contemporary plumbing fixtures. The flexible 4th bedroom easily adapts to a private home den or executive office. Step outside to your ultimate outdoor sanctuary: a massive under-roof lanai area transitions smoothly to a shimmering 14x28-foot pool, creating the perfect backdrop for Florida entertaining. Beyond the aesthetics, this home offers unparalleled mechanical peace of mind and insurance efficiency: a newer roof (2018), complete hurricane impact windows and sliders (2018), a newer A/C system with all-new ductwork (2021), and a newer water heater (2019). All new landscaping in the back with shell comes with minimum maiantance and beach style yard. Tucked away in a highly desirable South Sarasota location, you are within arm's reach of premier shopping, local dining, and just minutes away from the world-famous quartz sands of Siesta Beach. Beautifully updated and completely move-in ready, this spectacular home will not last long. Schedule your private tour today!
Listing is courtesy of: VIVE REALTY (941-600-8162)
Listing Agent: Nicole Long (941-600-8162)
2037 and 2039 Jo an Dr JO AN DR, SARASOTA, FL 34231
$619,00055 Days on yellowkey MLS ID: A4692288
REDUCED by $10,000 (1.6%) on 06/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 1988 Built: 1955 Tax: $5,534 (2024)Community: High AcresSpa: YesHalf Duplex
Taxes:$5,534
Tax Year: 2024
Remarks: Live the Florida Dream for Free – Premier Sarasota Duplex with Income Potential Why choose between a luxury home and a smart investment? At 2037 & 2039 Jo An Drive, you can have both. This meticulously maintained side-by-side duplex offers a rare opportunity to occupy a beautiful 2BR/2BA residence while the identical neighboring unit generates significant rental income to offset your costs. The Lifestyle: Enjoy your own private oasis featuring a luxurious swim spa and a massive, deep-bay garage perfect for boat storage—all just 3 miles from the world-famous Siesta Key Public Beach. The Income: With RMF-1 zoning, this property is a turnkey powerhouse. Whether you prefer stable long-term tenants or want to capitalize on the high-demand short-term rental market, the numbers work in your favor. The Location: Tucked away on a quiet street but only minutes from Southside Village, premier dining, and top-rated schools. Ideal for: The "House Hacker": Live in one side and let the other pay your mortgage. The Seasonal Resident: Live here in the winter and rent both units during the peak vacation season. The Savvy Investor: Maximize your ROI with two updated units in a prime coastal location. Don’t just buy a home—buy an asset. Contact us today for a private tour and a full rental income projection.
Listing Agent: Marcus Mumm (920-960-0413)
6139 HOLLYWOOD BLVD, SARASOTA, FL 34231
$999,90030 Days on yellowkey MLS ID: TB8512156
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 1953 Tax: $9,362 (2025)Community: Pine Shores Estate 4Th SecSpa: YesSingle Family
Taxes:$9,362
Remarks: Offered below appraised value at $999,900, this truly one-of-a-kind Sarasota property presents a rare opportunity to own a private family compound just minutes from Siesta Key and located West of the Trail in the highly desirable Pine Shores neighborhood. Set on an oversized 0.34-acre gated, fenced, and walled homesite, this exceptional property offers two separate living residences, incredible flexibility, and resort-style outdoor living — all with NO HOA and NOT located in a flood zone. This property also represents an outstanding investment opportunity with a proven rental history and strong income-producing potential, making it ideal for seasonal rentals, multigenerational living, guest accommodations, or long-term investment strategies. The beautifully maintained main residence features 3 bedrooms and 3 baths with approximately 1,685 square feet of living space and is being offered fully turnkey furnished. ROOF (3 - 4 years old), HVAC 2025, TANKLESS WATER HEATER 2025. Pride of ownership is evident from the moment you arrive, with a long paver driveway leading to a charming, gated breezeway entrance and lush, low-maintenance tropical landscaping. The main home showcases polished terrazzo flooring, crown molding, remodeled kitchen and baths, granite countertops, impact-resistant windows and doors, and a state-of-the-art water filtration system. Outdoor living is exceptional with a heated saltwater pool, spa, summer kitchen, and expansive entertaining areas designed for the ultimate Florida lifestyle. Built in 2013, the detached oversized two-car garage structure adds tremendous value and versatility. Upstairs, guests or extended family will enjoy a spacious studio apartment complete with a full kitchen, breakfast bar, custom cabinetry, hardwood flooring, upgraded lighting and fans, built-in hideaway bed, full bath, and private laundry area. The garage also includes built-in storage shelving and an additional side carport. The oversized paver driveway and side access provide abundant room for boat, RV, or recreational vehicle parking. The expansive lot also offers future flexibility with room to potentially expand, add additional structures, or create a custom luxury estate environment. Located just minutes from Siesta Key Beach, Phillippi Estate Park, shopping, dining, and Sarasota’s vibrant cultural attractions, this is a truly special property combining location, privacy, flexibility, lifestyle, and investment value in one extraordinary offering.
Listing is courtesy of: MARZUCCO REAL ESTATE (239-776-5194)
Listing Agent: Lisa Kohan (239-272-5901)
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