Location: Sarasota , 34231
Do Not Show Listings
5720 ISANDA PL, SARASOTA, FL 34231
$785,00016 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,994
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
2149 WASON RD, SARASOTA, FL 34231
$577,000121 Days on yellowkey MLS ID: A4682139
1 Days Off yellowkey (back on 6/10/2026)
REDUCED by $20,000 (3.4%) on 05/19/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1766 Built: 1956 Tax: $2,157 (2025)Community: River ForestSingle Family
Taxes:$2,157
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Classic Florida charm meets thoughtful modern updates at this prime Sarasota location! This beautifully maintained 3-bedroom, 3-bathroom home offers character, space, and an exceptional lifestyle just minutes from world-renowned Siesta Key Beach and vibrant Downtown Sarasota. Inside, you’ll find timeless original built-ins that add warmth and charm, paired with an open concept layout designed for comfortable living. The home features an UPDATED KITCHEN AND BATHROOMS with modern finishes, updated flooring throughout, and abundant natural light that enhances the inviting atmosphere. The spacious primary suite includes a great walk-in closet, providing generous storage and everyday convenience. A great bonus is one of the additional bedrooms is an ensuite! Major improvements provide peace of mind, including a 2024 METAL ROOF, NEWER WINDOWS AND DOORS, and an UPDATED SEWER LINE — offering both durability and long-term value. Step outside to exceptional outdoor living in a large, fully fenced backyard designed for both relaxation and recreation. Enjoy beautiful paver areas perfect for entertaining, a private putting green for golf enthusiasts, and a storage shed for added convenience. There is ample space to park your boat or RV, and a private well irrigation system helps maintain a lush landscape efficiently while keeping water costs down. Located near iconic Phillippi Creek, residents enjoy access to a community dock for boating, kayaking, and fishing. The optional annual HOA of $150 provides outstanding value, including landscape maintenance, pond and park upkeep, dock maintenance for boaters, a community savings fund, and social gatherings such as an annual Easter egg hunt — blending convenience with neighborhood connection. Whether you're seeking a primary residence, seasonal retreat, or investment opportunity, this property delivers location, lifestyle, and lasting quality in one of Sarasota’s most desirable areas. NO FLOOD ZONE, NO CDD FEE.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Jillian Sacco (941-445-3144)
5927 DRIFTWOOD AVE, SARASOTA, FL 34231
$575,00023 Days on yellowkey MLS ID: A4694069
REDUCED by $15,000 (2.5%) on 06/04/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1412 Built: 1969 Tax: $3,188 (2025)Community: FlorenceSpa: NoSingle Family
Taxes:$3,188
Remarks: Welcome to 5927 Driftwood Ave., Sarasota, FL 34231—a classic Florida ranch home nestled in a desirable “West of Trail” community, just one block from the Intracoastal Waterway. Set on over a quarter of an acre, this Sarasota property offers a rare combination of timeless charm and modern updates in a location central to Siesta Key’s world-famous beaches, Phillippi Estate Park, and all the shopping, dining, and entertainment Sarasota is known for. The curb appeal stands out with a covered front porch and a welcoming Florida feel. Inside, the great room features open living and dining spaces with tile floors, a chandelier with ceiling medallion, and a crown-molding accent wall. Sliding doors connect the living area to a bright home office, offering an ideal setting for relaxation or entertaining. The kitchen is designed for both style and function, featuring custom white cabinetry with generous storage, gold hardware and fixtures, gold-veined white countertops, and a dedicated coffee station. A gas range is exciting for anyone who loves to cook, and the laundry is conveniently located just off the kitchen. Enjoy an apron sink, custom floor-to-ceiling pantry, stainless steel appliances, and a peninsula bar with drop lighting. There is also direct entry to the attached two-car garage with attic storage. Out back, your private backyard oasis awaits—surrounded by palm trees and privacy fencing. The heated open-air pool and covered lounge area—equipped with double ceiling fans—create a true Sarasota retreat for dining, relaxing, or entertaining. The pool bath features artisan blue scalloped tile, a walk-in shower with dual rainfall heads, a vessel sink atop a white shaker vanity with gold fixtures, and a sculptured mirror, all in an airy, light-filled palette. Both bedrooms offer wood-tone flooring, ceiling fans, and customized closet storage. The primary suite includes a walk-in closet and a recently updated en suite bathroom with a glass-enclosed, walk-in shower and marble-topped vanity. The second bedroom features mirrored closet doors and built-in organizer shelving. Additional storage is available in the hallway closet and attic. Practical features include partially updated windows and a propane tank. With no HOA restrictions at 5927 Driftwood Ave., you’ll enjoy the flexibility to bring your boat, RV, or other recreational vehicles—offering convenience for a variety of interests. Updates have already been started, allowing for your own finishing touches over time. Built in 1969, this home reflects the enduring craftsmanship of its era while providing endless opportunities for personalization. The unbeatable location, spacious lot, and flexible amenities make this Sarasota home a fantastic choice for those seeking a full-time residence or investment in a rapidly appreciating neighborhood. Experience the best of Sarasota living at 5927 Driftwood Ave.—just blocks from the Intracoastal Waterway, minutes to Siesta Key, and close to everything that makes Sarasota, Florida, such a desirable place to call home.
Listing is courtesy of: CANDY SWICK & COMPANY (941-954-9000)
Listing Agent: Candy Swick (941-376-9000)
1521 S LAKE SHORE DR, SARASOTA, FL 34231
$5,980,000496 Days on yellowkey MLS ID: A4637673
REDUCED by $310,000 (4.9%) on 04/20/2026
Bed: 4 Bath: 6.0 Gar: 4 Liv Area Sq Ft: 4866 Built: 2025Monthly Fee: $25 Tax: $7,375 (2024)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$7,375
Tax Year: 2024
Remarks: The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.
Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)
Listing Agent: Sara Boudarga (941-321-6352)
5800 HOLLYWOOD BLVD #112, SARASOTA, FL 34231
$159,00015 Days on yellowkey MLS ID: A4695217
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 679 Built: 1976 Tax: $1,728 (2025)Community: Baywood Colony Garden AptsCondo
Taxes:$1,728
Remarks: Welcome to effortless Sarasota living at 5800 Hollywood Blvd—an inviting 1-bedroom, 1-bath condo ideally positioned for both comfort and convenience. This well-appointed residence offers a light and functional layout, perfect as a primary home, seasonal retreat, or investment opportunity—your chance to own a piece of paradise. Enjoy a relaxed coastal lifestyle just minutes from the world-renowned Siesta Key Beach, where powdery white sands and turquoise Gulf waters await. Everyday conveniences are at your doorstep, with an array of shopping, dining, and entertainment options nearby, creating the perfect balance of tranquility and accessibility. The interior offers a comfortable living space with a seamless flow, providing a welcoming environment to unwind or entertain. Whether you're enjoying a quiet morning or returning after a day at the beach, this residence delivers easy, low-maintenance living in a highly desirable location. An exceptional opportunity to own a piece of paradise in Sarasota at an attractive price point, close to everything that makes this area so sought after.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
3501 N VILLAGE CT #220, SARASOTA, FL 34231
$288,31064 Days on yellowkey MLS ID: A4688282
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1686 Built: 1978Monthly Fee: $367 Tax: $1,929 (2025)Community: Village In The PinesSpa: NoCondo
Taxes:$1,929
Elementary School: Gulf Gate Elementary
Remarks: Virtually Staged. Great location near Siesta Beach, Gulf Gate, shopping and restaurants! Come see this spacious corner lot Condominium/ 1/2 Duplex, located in Village In The Pines NORTH- a private hidden community of 2 cul-de-sac streets w/ community pool and a total of 42 extra large duplex/condominiums, all with actual attached garages, which is a very rare commodity. This 2250 sq ft villa is a 2 bd/2ba split floor plan featuring all tile, except carpeted spare bdrm and neutral paint throughout. The spacious entry features an expensive, beautiful solid brass Waterford crystal ceiling light and a large double 5 shelf closet. Remodeled kitchen w/ tray ceiling, beautiful solid wood Glendale oak cabinets w/ 12 extra large drawers, 12 double cabinets and 1 single + neutral light Silestone counter tops & 2018 all stainless hardware & appliances, stainless sink & faucet, digital 3 rack solid surface oven & stove combo w/pull out storage drawer, digital micro +fan combo. Kitchen sliders open onto a fenced pavered patio that could be extended to the length of the unit. The dining room features an expensive Hinkley solid brass chandelier w/ 2 matching side wall decor only sconces, french doors open to a 2026 remodeled outdoor atrium w/ shell drained floor, a perfect place for private sunbathing or plants or table. Living room has 2 vertical windows and steps down to the connecting Florida room w/ large picture windows & a solid metal stained glass look light and fan combo. Master bedroom features terracotta ceramic tile, stainless steel fan, 2 vertical windows, room for king bed & large furniture, PROFESSIONALLY DESIGNED WALK IN CLOSET w/ 18 shelves 8 lrg drawers, single & double hung; next to walk in is a large 5 shelf closet + en-suite bathroom w/ safety bars & handles, tiled step in shower & bench, 3 light fixtures, extra long solid wood vanity w/ marble top & lots of drawers. Other side of unit has large spare bedroom w/ 2 long vertical windows, cross wall closet & light beige carpet. Spare bath has sliding door shower/tub combo, lrg solid wood vanity w/ drawers, upscale chrome fixtures & window. Hall has 5 shelf linen closet & brass Waterford crystal ceiling light, same light in laundry room w/ washer, dryer & full wall closet + A/C handler. The door opens into 2 car garage w/ 2 lrg peg boards, lrg work bench, laundry sink tub, 28 gal water heater, moisture barrier reinforced ceiling, digital coded opener & 2 car driveway. This home highlights additional upgrades of new inside solid wood doors throughout with Baldwin brass handles & hinges, upgraded security system, 2023 new roof under warranty and 2020 repiped and replumbed entire interior. Gated community heated pool is 5 driveways east on same side of street, includes Cabana w/ bath, shower + changing facilities. Community is 55+, pet free & low fees. Located right behind Beneva Village shopping center w/ over 40 different retail, fast food, hardware, restaurants, grocery, gym, banks, etc. Bus stop just outside front gate connects to Sarasota Westfield Mall to go anywhere. Ready to move right in & enjoy the Florida lifestyle you've been waiting for. Won't last!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Yvonne Blackburn (941-350-6398)
5515 ASHTON WAY #5515, SARASOTA, FL 34231
$250,000107 Days on yellowkey MLS ID: A4683535
REDUCED by $25,000 (9.1%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1993Monthly Fee: $315 Tax: $2,155 (2025)Community: Ashton Lakes 08Condo
Taxes:$2,155
Middle School: Booker Middle
Remarks: Price Improvement!! Motivated sellers!! Bring Offers!! Location! Location! Location! Only 3.5 miles to the world-famous Siesta Key Beach. Experience the unique fine quartz sand from the Appalachian Mountains. Close to I-75, rte. 41, shopping, schools, hospitals and restaurants. This 2-bedroom 2 bath walk-up unit has high ceiling, attic space, bright and airy. Unfurnished. Assigned new carport and screened lanai with lake view. Relax on the lanai watching our flora & fauna. Ashton Lakes Community is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts & 4 pickleball courts,2 heated pools, one large with lap lane, shuffleboard, clubhouse, grilling stations, and other amenities. Our complex is connected by a foot bridge to Merchants Mart shopping center. Shops include CVS, ace hardware, liquor, Dollar store and the famous Detwiller's farm market for your shopping convenience. Come, make this slice of heaven your paradise in the sun. Roof 2020. See attachments for disclosures and updates. Welcome to Ashton Lakes...a well-kept secret location!!
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
5697 ASHTON LAKE DR #6, SARASOTA, FL 34231
$236,000175 Days on yellowkey MLS ID: A4675578
REDUCED by $9,000 (3.7%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 848 Built: 1984Monthly Fee: $315 Tax: $3,029 (2024)Community: Ashton LakesSpa: NoCondo
Taxes:$3,029
Middle School: Sarasota Middle
Remarks: Location! Location! Location! Only 3.5 miles to the World Famous Siesta Key Beach, with its fine sugary quartz sand. This much sought after 2-bedroom 2 bath unit is on the ground floor, overlooking the vast expanse of a natural spring fed lake with very pleasant view. The screened lanai faces east. Unit is bright and airy. Unit was updated in 2012 with vinyl floors, kitchen cabinets, granite counter tops and updated bathrooms. Ashton Lakes is located on 33 acres of luscious greenery, 4 lakes, 2 heated pools, one with lap lane, 2 tennis courts with 2 pickle ball courts on each, shuffleboard, clubhouse and other amenities. Close to I-75, trte.41, hospitals, schools, restaurants and shopping. We are also connected to Merchant Mart shopping center with CVS, ACE hardware, restaurants, and the famous Detwiler Farm Market. Roof 2009. Come be a part of this friendly community....
6283 GREEN VIEW CIR S #102, SARASOTA, FL 34231
$179,9004 Days on yellowkey MLS ID: D6147713
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1545 Built: 1973Monthly Fee: $656 Tax: $260,930 (2024)Community: Village In The PinesVilla
Taxes:$260,930
Remarks: Virtually Staged. Bright and Open floor plan, immaculate villa has many updates including new in 2025 roof, refrigerator, washer and dryer. Other important upgrades included are whole house re-pipe, new plumbing from the villa to outside. (no cast iron) Primary bath has been remodeled with walk in shower, updated kitchen with recent granite. Tile floors throughout all main areas, this well maintained villa is ready for a new owner who would like a wonderful carefree lifestyle in this active over 55 community with large heated pool, clubhouse with lovely new updates. Just minutes to Siesta key and its world famous white sand beaches. Plus walk to Publix and restaurants. Great south Sarasota location. Sellers will also entertain an annual rental.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Gail Cristello (941-400-8878)
3262 CROSS CREEK DR #3262, SARASOTA, FL 34231
$200,00011 Days on yellowkey MLS ID: TB8512221
3 Days Off yellowkey (back on 6/9/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1984Monthly Fee: $624 Tax: $1,327 (2025)Community: Crooked Creek Sec 6Townhouse
Taxes:$1,327
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. Virtually Staged. Embrace the ultimate Sarasota lifestyle in this 2 Bedroom, 2 Bathroom condo in the serene and very private Cross Creek community - A 78-unit community offering a heated resurfaced pool, updated poolside kitchen, gazebo with seating, gas and charcoal grills, tennis/pickleball court, community storage with individual lockers, newer roofs (2021), new carports, and recently painted buildings. The community itself is nestled among native foliage in a secluded environment with a charming wooden bridge. This 1,027 SqFt. retreat features bright, open living spaces along with a walk-in closet, in-unit laundry, and sliding doors to a covered screened lanai that overlooks tranquil creek and water views. The unit features a highly functional layout with a living/dining room combo. There is a covered carport and ample guest parking. Enjoy direct access to the gated 72 acre Red Bug Slough Preserve which is perfect for birdwatching, hiking, and walking your dog. Despite this natural oasis, you are nearby the world-famous sands of Siesta Key Beach, Gulf Gate, downtown Sarasota and all of the premier dining and shopping that it has to offer. A true nature lover’s paradise.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Conner Mcbride (813-819-3489)
2852 NASSAU ST, SARASOTA, FL 34231
$352,50063 Days on yellowkey MLS ID: A4689690
REDUCED by $7,500 (2.1%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1344 Built: 1996 Tax: $4,033 (2025)Community: Virginia Heights SubSingle Family
Taxes:$4,033
Remarks: Virtually Staged. PRICE IMPROVEMENT!! This beautifully updated two-story home offers 3 bedrooms, 2 bathrooms, and a spacious open loft across 1,344 square feet of living space. The primary bedroom is conveniently located on the first floor. The renovated kitchen features shaker-style cabinets, stainless steel appliances, and sleek quartz countertops, while both bathrooms have been tastefully updated. Luxury vinyl plank flooring runs throughout the first floor of the home and carpet on the 2nd, adding both style and durability. Enjoy the convenience of a one-car garage and relax on the private deck overlooking a peaceful preserve and running brook. Nestled on a quiet dead-end street, this home is ideally located less than 4 miles from Siesta Key Beach and close to shopping, dining, schools, hospitals, and downtown amenities.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
2822 SAFE HARBOR CIR, SARASOTA, FL 34231
$369,90022 Days on yellowkey MLS ID: A4694591
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1224 Built: 1970Monthly Fee: $6 Tax: $3,108 (2025)Community: Gulf GateSpa: NoSingle Family
Taxes:$3,108
Remarks: One or more photo(s) has been virtually staged. Lowest priced (active) home in Gulf Gate and the seller will provide a credit for a shingle roof (for the main roof) at closing or replace the main roof with a shingle roof prior to closing. Look no further for this "priced to sell" home that is available for immediate occupancy ... don't wait; just won't last! Split Plan, "Built by Richmond", Air conditioner (York 14 Seer 2.5 ton Package unit w/8kw heat kit) replaced 2019 & the plumbing replaced overhead 1995. The location is on a quiet cul-de-sac and is ideal with little traffic. Primary Bedroom Suite offers a bay window and is 20 x 11 with a walk-in-closet. Both bathrooms are large. Wonderful neighbors and the enforced deed restricted community keeps the homes nice. Membership is optional at $75 a year but the deed restrictions must be followed. Sidewalks line the neighborhood and Gulf Gate is a community of good neighbors! World renowned Siesta Key beaches are within 10 minutes and cultural downtown Sarasota is only 20 minutes away and it offers fine dining, entertainment, shopping, movie theaters, opera, Selby Gardens and more! Make this Gulf Gate Gem yours today!
Listing is courtesy of: DEBBIE HERING REALTY & ASSOC. (941-320-1070)
Listing Agent: Debbie Hering (941-320-1070)
2311 SANDRALA DR, SARASOTA, FL 34231
$875,00080 Days on yellowkey MLS ID: A4687185
REDUCED by $20,000 (2.2%) on 06/09/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1968 Built: 2024 Tax: $6,846 (2025)Community: RidgewoodSingle Family
Taxes:$6,846
Remarks: Virtually Staged. This stunning home represents a rare opportunity to acquire a newly constructed residence located inside the City of Sarasota, offers an open-concept layout 3 bedrooms, 2 and a half bathrooms, 2 car garage, featuring custom closets, high ceilings, and abundant natural light through hurricane-rated impact-resistant windows, sliders, and doors, concrete block construction, and elevated hurricane standards.The kitchen stands out with quartz countertops, soft-close cabinetry, stainless-steel appliances, flowing seamlessly into the dining area and expansive great room with perfect sightline to the enclosed patio and rear green yard. No HOA restrictions.Ideally located for effortless travel and coastal lifestyle enjoyment, this home is approximately 25 minutes from Sarasota–Bradenton International Airport, about 1 hour 10 minutes from Tampa International Airport, 20 minutes to Lido Key, and about 15 minutes to Siesta Key, unforgettable Gulf sunsets. Situated outside of a flood zone, this exceptional residence presents a rare opportunity to own a custom-built contemporary home where design, craftsmanship, location, and lifestyle converge. Easy access to Van Wezel Performing Arts Hall, top-rated schools, Southside Village, Ringling College, USF Sarasota-Manatee, and I-75. Short drive to iconic St. Armands Circle and Lido Beach.Don't miss the opportunity, schedule your showing time.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jarek Chudoba (941-400-4850)
1541 CARIBBEAN DR, SARASOTA, FL 34231
$5,500,0009 Days on yellowkey MLS ID: A4695466
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 6035 Built: 2004 Tax: $41,012 (2025)Community: Coral CoveSpa: YesSingle Family
Taxes:$41,012
Remarks: Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best of Sarasota’s luxury lifestyle. Encompassing over 6,100 square feet, the residence was thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. A dramatic two-story living room, sweeping staircase, extensive custom millwork, and walls of glass create a sense of timeless elegance while framing breathtaking water views throughout the home. The gourmet kitchen serves as the heart of the residence, seamlessly connecting to multiple gathering spaces and opening effortlessly to the expansive waterfront terrace. Corner sliding glass doors dissolve the boundaries between indoors and out, revealing a resort-style infinity-edge pool, summer kitchen, covered entertaining areas, and sparkling bay views beyond. The luxurious primary suite is a private waterfront retreat featuring a separate dressing room, generous dual closets, and serene water vistas. Additional guest suites provide exceptional comfort and privacy for family and visitors alike. Designed for both recreation and relaxation, the home also features a private office/library, elevator access, media and game room with full bar, and a four-car split garage. Outside, the lifestyle continues with a private dock, boat lift, fishing pier, and immediate access to Sarasota Bay. Whether enjoying sunset cruises, waterfront dining, or simply relaxing poolside while watching dolphins and boats pass by, every day feels like a vacation. Rarely does a property combine this level of space, waterfront presence, boating access, and location. Just minutes from downtown Sarasota, St. Armands Circle, and the area’s renowned beaches, this is a home designed for those who expect the very best.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Daria Fairchild (941-650-7207)
5420 EAGLES POINT CIR #402, SARASOTA, FL 34231
$650,00029 Days on yellowkey MLS ID: A4692894
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1715 Built: 1993Monthly Fee: $167 Tax: $5,645 (2025)Community: Eagles Point At The Landings 1Condo
Taxes:$5,645
Remarks: Perched atop the building, this exceptional penthouse offers sweeping, unobstructed views over a lush green preserve, complemented by enticing peek-a-boo glimpses of the Intracoastal Waterway. Enjoy these panoramic vistas from the living room, primary bedroom or a stunning glassed-in seating area. This unique space captures expansive scenery while inviting gentle coastal breezes, creating a seamless blend of indoor comfort and outdoor beauty. The kitchen features a cozy breakfast nook, perfect for starting your day. The spacious primary suite includes a large walk-in closet, separate vanities, a walk-in shower with a rainhead, plus a semi-private water closet. The versatile den or study is outfitted with a closet, offering flexibility, and can easily be converted into a third bedroom to suit your needs. Located behind the gates of The Landings, this maintenance-free residence is ideal as a full-time home or seasonal getaway, offering both tranquility and convenience. Just minutes from vibrant downtown Sarasota, you’ll have easy access to an array of dining, shopping and cultural attractions, while world-famous Siesta Key Beach is only a short drive away. Residents of The Landings enjoy an impressive array of amenities within this private, gated community. Take advantage of Har-Tru tennis courts, a fitness center and an active clubhouse. The junior Olympic-sized swimming pool provides a place to relax or stay active, while kayak storage and a launch area make it easy to explore the nearby Intracoastal Waterway. A scenic nature trail further enhances the community’s appeal, offering peaceful surroundings and direct access to the water. This penthouse delivers an exceptional lifestyle defined by natural beauty, comfort and convenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
2431 BISPHAM RD, SARASOTA, FL 34231
$550,00064 Days on yellowkey MLS ID: A4687726
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1966 Tax: $4,993 (2025)Community: Gulf GateSingle Family
Taxes:$4,993
Remarks: LOOKING FOR EXCEPTIONAL VAULE? THIS IS IT!!!!! This beautifully renovated home has been completely updated inside and out. Featuring brand-new tile flooring throughout, hurricane-impact windows, and a new A/C system, no detail has been overlooked. The fully updated kitchen offers wood cabinetry with soft-close doors and pull-out shelving, along with high-end appliances including a cooktop, range hood, dishwasher, refrigerator, double built-in oven, and drawer microwave. An instant hot water feature has also been added at the sink for added convenience. The primary suite includes a spacious glass walk-in shower, dual sinks, wood cabinetry, and modern lighted mirrors. The second bathroom has also been fully updated with new tile, wood cabinetry, and a lighted mirror. A permitted and completed bathroom addition provides a third full bathroom and a private suite located off the rear of the garage, featuring its own entrance—ideal for guests, an in-law suite, or flexible living space. With extensive upgrades throughout, this home offers outstanding value and is priced to sell. Schedule your private showing today!
Listing Agent: Jodi Fleming (941-993-6331)
3122 REGATTA CIR, SARASOTA, FL 34231
$685,000128 Days on yellowkey MLS ID: A4680447
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1642 Built: 1965 Tax: $5,399 (2025)Community: Gulf Gate WestSpa: NoSingle Family
Taxes:$5,399
Remarks: Gulf Gate transformation in this meticulously renovated 3-bedroom, 2-bathroom sanctuary. Situated on a quiet circle just minutes from the world-class sands of Siesta Beach, this home has been professionally redesigned from top to bottom with uncompromising attention to detail. Enjoy total peace of mind with a comprehensive list of 2022–2025 upgrades, including a new roof, HVAC and ductwork, PEX plumbing, and new sewer lines. The exterior features durable Hardie siding, fresh paint, and hurricane-impact windows and doors at the front, ensuring both efficiency and protection. Designer Interiors The heart of the home is a chef’s kitchen featuring Level 4 Cambria Quartz, solid wood shaker cabinetry, and a custom built-in banquet. Modern luxury vinyl flooring flows through the open living spaces, leading to a charming shiplap-accented living room with an electric fireplace. Both bathrooms have been fully redone with high-end vanities, fixtures, and custom tile. Private Backyard Oasis Step outside to a brand-new inground pool with a custom water feature, all framed by a new wood privacy fence. The grounds are completed by professional landscaping, new lighting, and a modern irrigation system. Fully permitted and ready for its next chapter, this "better-than-new" gem offers the luxury of a custom build in an established, sought-after Sarasota location.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Deanna Boileau Gilman (860-884-7198)
1612 STICKNEY POINT RD #1612-1, SARASOTA, FL 34231
$274,90068 Days on yellowkey MLS ID: A4688336
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 Agent: Linda Ren (941-928-1393)
1705 FIELD RD, SARASOTA, FL 34231
$2,295,000220 Days on yellowkey MLS ID: A4671008
1 Days Off yellowkey (back on 5/11/2026)
REDUCED by $204,000 (8.2%) on 05/06/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2409 Built: 2020 Tax: $9,575 (2024)Community: Oyster Bay EstatesSingle Family
Taxes:$9,575
Remarks: Under contract-accepting backup offers. Welcome to this stunning, fully reimagined residence in Oyster Bay Estates, one of Sarasota’s most coveted West of the Trail neighborhoods. Renovated down to the studs with an effective build date of 2020, this exceptional home blends timeless coastal elegance with modern sophistication, showcasing the level of craftsmanship and finish quality typically found in five million dollar plus luxury properties. Thoughtfully designed throughout, the home features wide-plank wood flooring, custom millwork, and an open-concept floor plan designed for both everyday living and effortless entertaining. The gourmet kitchen serves as the centerpiece of the home, offering designer cabinetry, quartz countertops, an oversized island, Sub-Zero and Wolf appliances, and luxury Perrin & Rowe fixtures. The residence includes four spacious bedrooms, three full bathrooms, and two half baths, each beautifully finished with premium materials and spa-inspired details. The beachy character continues with an outdoor shower. Major systems and components have all been replaced, including the electrical, plumbing, HVAC systems, roof, siding, and hurricane-impact windows and doors, including the garage door, providing both comfort and peace of mind. Located in Flood Zone X, flood insurance is not required. Privately set back from the street, the property offers a quiet, resort-like setting with lush new tropical landscaping featuring coconut palms, cabbage palms, orchid trees, pitch apple hedges, and bougainvillea to name a few. The outdoor spaces have been completely transformed with shell-finished hardscape, new patios, elegant walkways, and a private irrigation well. Offered fully furnished, this move-in-ready home is ideally located just moments from downtown Sarasota, St. Armands Circle, world-renowned beaches, shopping, dining, top-rated schools, and less than a block from the historic The Field Club. Buyer and Buyer’s Agent to verify all room dimensions.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Albert Joerger (941-685-6145)
1717 JOYCE ST, SARASOTA, FL 34231
$379,00037 Days on yellowkey MLS ID: A4691080
REDUCED by $20,000 (5.0%) on 06/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1382 Built: 1966 Tax: $3,784 (2025)Community: Tropical ShoresSingle Family
Taxes:$3,784
Remarks: Tropical Shores Community is Sarasota’s most budget-friendly boating spot with no HOA or deed restrictions! This charming 2-bedroom, 2-bath home, on a great lot, was recently painted, boasts a newer A/C system from 2022, a newer roof (2021), and septic tank replaced in 2021. It also features updated sewer lining and a stack replacement (2021). You’ll be just a short stroll from the community’s private marina and clubhouse. This affordable membership is voluntary and gives you access to the boat ramp, kayak/canoe launch, and slip rentals for easy access to the bay. Plus, you’re just a few minutes away from the nation's top beach, Siesta Key, and some great restaurants.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Babette Paige (941-587-1045)
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