Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
4957 CROSS CREEK RD #4957, SARASOTA, FL 34231
$279,000126 Days on yellowkey MLS ID: A4682348
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1981Monthly Fee: $632 Tax: $3,270 (2025)Community: Crooked Creek Sec 1Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,270
Elementary School: Wilkinson Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Nestled on the second floor of Sarasota's boutique Crooked Creek community, this thoughtfully updated two-bedroom, two-bath condominium offers a rare combination of refined interiors, natural surroundings, and low-maintenance living. Since 2022, the owners have invested significantly in the home. The kitchen was fully renovated in 2023 with sleek European-style cabinetry, black granite countertops, and all-new appliances , a clean, contemporary space that anchors the open living area. Underfoot, premium engineered hardwood flooring with a 4mm wear layer (refinishable) runs through the main living and dining rooms, installed in 2022. Overhead, a designer Hubbardton Forge light fixture in the dining area and a new ceiling fan with wall switch in the living room add considered detail throughout (2024). The second bathroom received a complete refresh in 2025 with a new toilet, vanity, and flooring. Fresh paint throughout ,the living and dining rooms, kitchen, master and second baths, hallway, and master bedroom ceiling ties everything together with a crisp, move-in ready finish. The functional floor plan is further enhanced by a glass-enclosed porch, offering additional living space and a seamless connection to the outdoors. The unit enjoys a private, tranquil setting with views of mature tropical landscaping and the adjacent Red Bug Slough Preserve a natural buffer that creates a true sense of retreat while keeping you centrally located. Crooked Creek is a 78-unit community with a heated pool, tennis and pickleball courts, a clubhouse, and outdoor gathering areas. Covered assigned parking and dedicated storage are included. Shopping, dining, and area beaches are all just minutes away.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Johnny Sokhon (941-961-4579)
1824 WEBBER ST, SARASOTA, FL 34239
$650,00057 Days on yellowkey MLS ID: A4691535
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1680 Built: 1968 Tax: $7,613 (2025)Community: Poinsettia Park 2Half Duplex
Taxes:$7,613
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment. The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a 50’ x 118’ lot ideally positioned for a stunning new custom home. Enjoy a highly sought-after location just minutes to the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and the vibrant arts, dining, and waterfront lifestyle of Downtown Sarasota. Whether you’re a builder, investor, or end user looking to create a dream home, this is a rare chance to build new in an established, high-demand area surrounded by luxury properties. Opportunities like this are becoming increasingly scarce—don’t miss your chance to capitalize on this premium location!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Carson (941-685-2879)
1394 HARBOR DR, SARASOTA, FL 34239
$7,750,000130 Days on yellowkey MLS ID: A4682309
REDUCED by $500,000 (6.1%) on 04/21/2026
Bed: 4 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5913 Built: 2004 Tax: $48,224 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$48,224
Remarks: Presenting a distinguished waterfront estate located in Sarasota’s premier bayfront community, Harbor Acres, widely regarded as the city’s most coveted neighborhood. Perfectly situated on a protected deep-water boat basin, this property offers immediate access to Sarasota Bay with the added benefit of a boat dock and lift on calm waters-ideal for larger vessels. With prized southern rear exposure, the home is bathed in natural light throughout the day, while capturing glowing sunsets across the water — a rare and highly desirable feature for waterfront living. The thoughtfully designed 4-bedroom, 6 bath floor plan offers exceptional flexibility and privacy, with distinct guest wings that function almost as private suites — ideal for hosting extended family, visiting friends, or even live-in arrangements without sacrificing personal space. The seamless flow between formal and casual living areas makes the home equally suited for elegant entertaining or relaxed everyday living. At the heart of the home, the chef’s kitchen features beautiful quartz countertops, island, abundant cabinetry, and premium appliances, opening effortlessly to the family room and outdoor living areas. A striking double-sided gas fireplace creates ambiance between key gathering spaces, enhancing both intimate evenings and larger gatherings. Enjoy the rare luxury of choosing between two primary suites. Both primary suites are serene retreats offering generous proportions, tranquil water views, and a spacious walk-in closets with custom built-ins designed for optimal organization. The spa-inspired baths provides a luxurious escape at the end of the day. Outdoor living is where this property truly shines. A fully equipped summer kitchen anchors the covered lanai, creating the perfect setting for waterfront dining and entertaining. The infinity edge pool, spa and outdoor lounge areas overlook the wide boat basin, where you can watch dolphins pass and boats glide by — all from the comfort of your own backyard.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
5560 CANNES CIR #3-106, SARASOTA, FL 34231
$579,000278 Days on yellowkey MLS ID: A4665433
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1825 Built: 2020 Tax: $3,133 (2024)Community: Phillippi LandingsSpa: YesTownhouse
Taxes:$3,133
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Beautiful luxury townhome with contemporary flair located only minutes from Siesta Key. This 3-story residence offers affordable luxury and maintenance-free living in a premier location on the shores of Phillippi Creek, where you are surrounded by 10 acres of stunning tropical foliage and landscaping. Rarely available, this is your chance to live in an open concept space with high ceilings, designer kitchen features, spectacular interior details and stylish bathroom fixtures. Upon entering this 3-bedroom, 3-bathroom home, you will fall in love with the bright, open floorplan featuring high-end finishes and an abundance of natural light. Enjoy relaxing on one of two lanais; one on the ground floor with outside access and another one upstairs with stunning views. There are stairs and a private elevator for your convenience as well as an oversized garage with plenty of room to store kayaks, golf clubs, beach chairs, fishing poles and more. The Phillippi Harbor Club Rackominium and Marina is right next door for your boating pleasures. There is also an onsite resort-style pool and kayak launch for active pursuits. Additional amenities include a clubhouse, dog park, fitness center and lighted boardwalk. You are minutes away from downtown Sarasota, fine dining, shopping, outdoor activities and the area’s famous beaches. Enjoy the best of Sarasota luxury living in the secluded, gated waterfront community of Phillippi Landings.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Michael Hays (941-376-1826)
1421 N LAKE SHORE DR, SARASOTA, FL 34231
$4,695,000193 Days on yellowkey MLS ID: A4674749
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4217 Built: 2021 Tax: $31,036 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$31,036
Remarks: Perfectly positioned on a spacious, private lot in the prestigious and highly sought-after Oyster Bay Estates community, the residence embodies exceptional design, architectural intention, and refined livability. Custom designed and built by distinguished, award-winning Platinum Coast Construction and completed in 2021, this 4-bedroom / 4 full & 2 half bath modern masterpiece was crafted with uncompromising detail and a focus on seamless indoor–outdoor living. Inside, a host of elevated finishes creates a sophisticated yet welcoming atmosphere. Level 5 flat-smooth walls, engineered oak hardwood flooring, 8' solid-core and obscure glass interior doors, 10" baseboards, floating vanities in all baths, and Quartz surfaces throughout promote a clean, modern aesthetic. A dramatic 72" glass fireplace anchors the living area, while the gourmet kitchen boasts high-performance appliances including a Thermador push-to-open column refrigerator, column freezer, 24" wine preserver, Bosch dishwasher, Bosch combo oven/microwave, and 36” induction cooktop. The striking 175-bottle wine room with stone wall adds a stunning design focal point for entertainers and collectors alike. The primary suite offers a spa-like retreat with marble finishes, a Wetstyle soaking tub, and an enclosed outdoor garden area with tropical landscaping, wood decking, and a private outdoor shower. Guest suites each feature en-suite baths and access to a serene outdoor spa-like space with lush plantings, decking, and an outdoor tub and shower—creating peaceful, private escapes separate from the main living areas. Designed for true resort-style living, the exterior features a spectacular 18' x 30' pool and spa with a custom waterfall wall, surrounded by tropical landscaping. The fully equipped outdoor kitchen includes a 42” Blaze gas grill, under-counter refrigerator, outdoor sink, and storage drawers. Additional features include hurricane-impact windows, an advanced security system, irrigation system, and a distinctive 2-car garage with wood-look paneling and a stunning mahogany double-door entry with obscure glass. Situated just moments from Siesta Key, downtown Sarasota, and within walking distance of the prestigious Field Club, Oyster Bay Estates is celebrated for its beautiful streetscapes, active social atmosphere, and proximity to the water and premier amenities. This exceptional residence offers luxurious contemporary living in one of Sarasota’s most desirable neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1185 S SHADE AVE, SARASOTA, FL 34237
$849,00093 Days on yellowkey MLS ID: N6143460
REDUCED by $25,900 (3.0%) on 04/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1956 Built: 1949 Tax: $7,776 (2025)Community: Avon HeightsSpa: NoSingle Family
Taxes:$7,776
Elementary School: Alta Vista Elementary
Remarks: Welcome to 1185 S Shade Ave, where location, style, and lifestyle come together in one exceptional property. Perfectly positioned just minutes from Downtown Sarasota, Siesta Key’s world-renowned beaches, Sarasota Memorial Hospital, top-rated schools, and Sarasota-Bradenton International Airport, this home offers true convenience in one of the area’s most sought-after corridors. Plus, enjoy peace of mind with NO HOA and located outside of a flood zone. Situated on a rare, oversized corner lot, this fully fenced property delivers privacy and curb appeal, while the backyard is built for Florida living. Enjoy a gorgeous saltwater heated pool (installed October 2021), surrounded by a travertine paver deck and low-maintenance turf yard, creating the ultimate outdoor retreat for entertaining or relaxing year-round. Inside, the home has been completely remodeled with a modern, high-end finish throughout. Features include luxury vinyl plank flooring, fresh interior paint, upgraded lighting, custom accent walls, and recessed lighting throughout. The stunning white kitchen is a true centerpiece, offering dark stainless steel appliances, soft-close cabinetry, a waterfall-edge countertop, glass tile backsplash, vent hood, ledgestone accents, and a spacious walk-in pantry. Originally built in 1949, this home was taken down to one interior wall and fully rebuilt in 2012, with all major systems and finishes updated throughout. Offering nearly 2,000 square feet, the layout is both functional and inviting. Recent updates include a brand new hot water heater and a 3-ton AC system installed in May 2022, providing added peace of mind and efficiency. The property also features an oversized 20x32 garage with a motorized screen, ideal for keeping the space cool while working, along with a covered carport for additional shaded parking. Offered fully furnished, this property is truly turnkey, making it ideal as a full-time residence, second home, or income-producing investment. Opportunities like this are rare — a fully remodeled, move-in ready home with a newer pool, updated major systems, oversized lot, NO HOA, not in a flood zone, and a prime Sarasota location, all at a compelling price point. This is one you don’t want to miss.
Listing is courtesy of: CORNERSTONE R.E OF SW FL (941-404-4620)
Listing Agent: Erik Dunigan (941-441-5253)
3360 HIGEL AVE, SARASOTA, FL 34242
$1,549,000132 Days on yellowkey MLS ID: A4682008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1960 Tax: $13,348 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$13,348
Remarks: Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.
Listing Agent: Natalie Gutwein (941-993-2660)
5369 LAKE ARROWHEAD TRL #17A, SARASOTA, FL 34231
$374,90075 Days on yellowkey MLS ID: A4689393
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1800 Built: 1983 Tax: $2,674 (2025)Community: Lake ArrowheadSpa: NoCondo
Taxes:$2,674
Elementary School: Gulf Gate Elementary
Remarks: LAKEFRONT VALUE with Stunning Views in this Luxury End Unit, that is "Low-Cost Living" in sought after Lake Arrowhead. This end unit condo offers 3 Bedrooms and 3 Bathrooms and is completely remodeled! The air conditioner and heat pump were replaced in April 2026 and the updated chef's kitchen is high-end quality with custom cabinetry, stainless appliances and quartz tops. $539/month in low HOA fees covers the roofs and includes much of your insurance cost! Rarely available, this 1,800 square foot condo offers comfortable living with high-end finishes throughout. The enclosed 3rd bedroom offers a large walk-in closet and private bathroom and it currently is used as an entertaining lounge area with incredible views of the lake and wildlife through the floor to ceiling windows! Furniture is negotiable! HOA fees include cable, pest control, exterior maintenance and lawn care. At this price, this condo is more affordable than most residential homes! Lake Arrowhead is a hidden gem in South Sarasota with lush landscaping and lakes. The Great Room with high ceilings has a large sliding glass door that opens onto the spacious, covered lanai that overlooks the lake with a very peaceful view. The Key West Clubhouses is next door and is steps away for convenience. Enjoy the heated community pool, the large community room-kitchen-library in the clubhouse and the fishing pier. This is value priced for a larger condo in Lake Arrowhead and this condo is one-of-a-kind with it's fine finishes! Management is on-site and this condo includes one carport space. This community has everything you could desire and is located next to the 72-acre Red Bug Slough Preserve that is pet friendly and has several miles of hiking trails, a playground, picnic shelters & a fishing dock. Lake Arrowhead consists of 64 condos which is conveniently located to everything, including the World Renowned Siesta Key Beaches, Legacy Trail, Costco, several fitness centers, Publix, A+ Schools, Fine Restaurants and the Gulf Gate Library. UTC Mall and cultural downtown Sarasota are within 20 minutes for opera, movie theaters, dining, Selby Gardens & more! Make this your favorite place to relax and unwind as you are surrounded by tropical landscaping and lake views from nearly every room. Come and see this amazing condo; EZ show!
Listing is courtesy of: DEBBIE HERING REALTY & ASSOC. (941-320-1070)
Listing Agent: Debbie Hering (941-320-1070)
1253 N BASIN LN, SARASOTA, FL 34242
$3,295,000251 Days on yellowkey MLS ID: A4668457
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3464 Built: 1971Monthly Fee: $450 Tax: $42,282 (2024)Community: Siesta Properties IncSpa: YesSingle Family
Taxes:$42,282
Remarks: One or more photo(s) has been virtually staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water’s edge. At the heart of the home lies a state-of-the-art culinary haven. The chef’s kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you’ll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Louis Wery (941-232-3001)
2456 MISSARA LN, SARASOTA, FL 34231
$2,350,000301 Days on yellowkey MLS ID: A4663280
0 Days Off yellowkey (back on 4/1/2026)
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3224 Built: 2022Monthly Fee: $200 Tax: $18,996 (2024)Community: ShorelineSpa: YesSingle Family
Taxes:$18,996
Remarks: One or more photo(s) has been virtually staged. Welcome to 2456 Missara Lane in beautiful Sarasota, Florida. This stunning residence offers the perfect blend of coastal living and modern comfort. Nestled in a highly desirable neighborhood, the property features Phillippi Creek water access with a private boat dock, making it ideal for boating, fishing, or simply enjoying the serene waterfront lifestyle. Best of all, the home sits in a no flood zone, providing peace of mind for years to come. Inside, you’ll find custom details throughout, from thoughtfully designed living spaces to elegant finishes that set this home apart. The heart of the home is the gourmet kitchen, equipped with stainless steel appliances, custom cabinetry, and plenty of counter space for entertaining and cooking with ease. Located just a short walk to Riverview High School, the property combines everyday convenience with exceptional amenities. Whether you’re enjoying quiet evenings by the water, hosting gatherings in the open living areas, or taking your boat out for the day, this home truly has it all. Seller is offering 5% financing (Terms Apply)!!
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
6154 MIDNIGHT PASS RD #A-3, SARASOTA, FL 34242
$619,00074 Days on yellowkey MLS ID: A4689306
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 836 Built: 1966 Tax: $4,427 (2025)Community: Casa Blanca VillasCondo
Taxes:$4,427
Remarks: Tucked along the sugar-white sands of world-renowned Siesta Key, this freestanding villa offers the rare combination of effortless ownership, strong rental potential, and immediate coastal enjoyment. With direct beach access just steps away, every day begins and ends with the Gulf as your backdrop. Thoughtfully and completely updated, the residence features easy-care terrazzo flooring, a beautifully renovated kitchen with stainless appliances and dining space, along with a refreshed full bath and convenient half bath. The screened porch invites year-round indoor-outdoor living, while an impact-rated sliding glass door enhances both comfort and peace of mind. Positioned just steps from the community pool and clubhouse, this villa is part of an active, well-managed rental community offering flexible 5–7 day minimum rentals, making it an exceptional opportunity for those seeking income potential with personal-use flexibility. On-site management simplifies ownership, whether you’re local or remote. Sold furnished, the home is ready for immediate enjoyment or rental—just bring your suitcase. Parking is conveniently located directly in front of the unit. Beyond the property, you’re ideally situated near Siesta Key’s popular dining, shopping, and parks, while still enjoying a quieter stretch of beach perfect for morning walks, sunset swims, and relaxed days on the sand. Whether you’re looking for a smart investment, a personal retreat, or the perfect blend of both—this villa delivers the Siesta Key lifestyle with ease.
Listing Agent: Ryndie Brusco (941-809-6913)
847 FREELING DR, SARASOTA, FL 34242
$3,950,00060 Days on yellowkey MLS ID: A4690268
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4034 Built: 1954 Tax: $40,498 (2025)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$40,498
Remarks: Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
4185 S SHADE AVE, SARASOTA, FL 34231
$616,000160 Days on yellowkey MLS ID: A4678362
0 Days Off yellowkey (back on 1/23/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2122 Built: 1990 Tax: $9,222 (2025)Community: Sarasota-Venice Co River SubSpa: YesSingle Family
Taxes:$9,222
Remarks: UNBELIEVABLE OPPORTUNITY! This 3-4 bedroom / 3 bathroom home is directly on Phillippi Creek with a dock and boat lift. This home sits at the very private end of a cul de sac on .5 acres of land! Enter and immediately notice the soaring 15-foot vaulted ceilings & two skylights in the living room with fireplace and handsome stonework all the way up. The rear private patio overlooks greenery. The eat-in kitchen has the same high ceilings and features a central island, quartz tops, raised-panel cabinetry, and a pantry. The 15-foot ceilings carry into the primary bedroom and there is a door out to the rear screened patio, swimming pool, and hot tub. The primary bath features a walk-in closet, dual vanities, and separate shower and soaking tub. There is a separate dining room and split guest bedroom/bath on the main floor as well. Upstairs has a third bedroom, a small bathroom, and fourth bedroom (no closet)-also perfect as an office. Come make this special home all your own with your remodeling ideas and a little TLC! --What the boater's want to know...The dock is older as is the lift. There is a sitting area at the end of the dock for sunrise. It appears to have 3-foot depth under the lift at mean-high tide and it is approximately a relaxing 35-minute boat ride to the Intracoastal Waterway passing under one bridge with approximate clearance of 9.5'. Come see this super waterfront opportunity today at an unbelievable price!
Listing Agent: Joe Cleary (941-650-8485)
6006 MIDNIGHT PASS RD #51, SARASOTA, FL 34242
$575,00076 Days on yellowkey MLS ID: P4938368
Bed: 1 Bath: 0.0 Liv Area Sq Ft: 600 Built: 1960 Tax: $3,999 (2025)Community: Casa MarSpa: NoApartment
Taxes:$3,999
Remarks: PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!
Listing is courtesy of: HUT REALTY, LLC (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
1429 N LAKE SHORE DR, SARASOTA, FL 34231
$5,595,000193 Days on yellowkey MLS ID: A4674740
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4545 Built: 2026 Tax: $9,862 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$9,862
Remarks: One or more photo(s) has been virtually staged. Experience luxury West-of-Trail living in Sarasota’s coveted Oyster Bay neighborhood. This newly built 2026 custom residence offers 5 bedrooms, 5 full and 2 half baths—all on one thoughtfully designed living level—featuring 4,545 sq. ft. under air and 5,689 sq. ft. total. Set on an impressive 130' x 150' corner lot (0.45 acres), the home is surrounded by a lush tropical oasis that provides exceptional privacy. A dramatic two-story foyer with 21’ ceilings and a steel-and-impact-glass entry door welcomes you inside. Engineered oak hardwood flooring, 10” baseboards, and sleek horizontal receptacles enhance the home’s modern architectural aesthetic. The expansive open-concept kitchen and great room are flooded with natural light from ten windows and four 20’ hurricane-impact glass sliders that open to the outdoor living space. The gourmet kitchen is a chef’s dream, offering an 8-seat center island, large walk-in pantry, quartz countertops, and premium appliances including a Bosch 36” natural gas/induction cooktop, 36” Thermador refrigerator column, 24” Thermador freezer column, 24” full-height Thermador wine cooler, Bosch dishwasher, and 30” Bosch oven/microwave combo. Retreat to the luxurious main suite featuring a Wetstyle tub with wood surround, marble accents, and slate and porcelain flooring. Additional highlights include level-5 smooth interior walls, 8’ solid-core and obscure-glass interior doors, a stunning 175-bottle wine room with marble wall and glass enclosure, Samsung pedestal washer & dryer, and an advanced alarm and exterior security lighting system. The outdoor living area is designed for year-round enjoyment with a summer kitchen equipped with a Blaze 42” gas grill, sink, and under-counter refrigerator. A 15’ x 28’ pool and spa with a custom waterfall feature, plus an outdoor shower, complete this private retreat. The property also offers an irrigation system and a spacious 3-car garage. An exceptional opportunity to own a brand-new, luxury single-level home in one of Sarasota’s most desirable West-of-Trail communities.
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000232 Days on yellowkey MLS ID: A4669078
REDUCED by $250,000 (3.0%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4705 Built: 2021Monthly Fee: $13 Tax: $68,556 (2025)Community: San Remo EstatesSpa: YesSingle Family
Taxes:$68,556
Remarks: Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal contemporary residence blends clean architectural lines with warm, natural finishes, ideal for buyers seeking newer construction, move-in-ready condition, and hurricane-resilient design in a prime location. Positioned on protected sailboat water with no fixed bridges, the property offers seamless access to Sarasota Bay and a short, unobstructed ride to the Gulf, making it perfectly suited for avid boaters. Spanning approximately 4,750 square feet under air, with nearly 3,000 additional square feet of outdoor living space, the home is designed around the indoor-outdoor lifestyle today’s luxury buyers prioritize. The open-concept layout is anchored by a chef’s kitchen featuring a sculptural marble island and Sub-Zero and Wolf appliances, flowing effortlessly into a great light-filled room with a stone fireplace, custom built-ins, and floor-to-ceiling glass sliders that open to expansive terraces. A temperature-controlled wine room with 1,800-bottle capacity adds a refined touch, while the dining space creates a striking architectural focal point. The primary suite offers true resort-style living, with private access to both a tranquil courtyard with spa and sauna and the waterfront pool terrace. Inside, a custom walk-in closet and spa-inspired bath reflect the level of finish expected in a luxury retreat. The second level features three additional bedrooms, a flexible gym or office, and a loft-style workspace, providing versatility for modern living. Outdoors, the illuminated saltwater pool with a glass wall, newly enhanced outdoor kitchen, and expansive entertaining areas create a private waterfront oasis. The deep-water dock is equipped with a 20,000-pound boat lift, dual jet ski lifts, and a floating dock, delivering a true boating lifestyle. Additional highlights include a three-car garage with a lift, epoxy flooring, and custom storage. A fully integrated smart home system, featuring programmable lighting and shades, whole-home audio, Apple TV integration, a generator, and high-speed WiFi, meets the expectations of today’s tech-forward buyer. Furniture is available separately to create a more turnkey concept. Located within San Remo Estates, the home offers a rare balance of privacy and central convenience. Just minutes from Siesta Key via the nearby North Bridge, beach access becomes part of everyday life. Set on a deep-water basin seconds from Sarasota Bay, the property provides protected docking with immediate access to open water and a short ride to the Gulf. Southside Village and Downtown Sarasota are both a quick drive away without the need to cross any bridges, offering boutique shopping, cafés, acclaimed dining, and a vibrant arts and cultural scene. Everyday conveniences, including top-rated schools, Sarasota Memorial Hospital, and key corridors like US-41 and I-75, are all within close reach. This is a location that seamlessly connects protected waterfront living with the very best of Sarasota.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
5500 MERRIMAC DR, SARASOTA, FL 34231
$1,685,000111 Days on yellowkey MLS ID: A4684914
REDUCED by $85,000 (4.8%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 1974 Tax: $6,537 (2025)Community: Phillippi Gardens 08Spa: YesSingle Family
Taxes:$6,537
Remarks: Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.
Listing Agent: Steve Abbe (941-400-3969)
1760 ARLINGTON ST, SARASOTA, FL 34239
$2,150,000313 Days on yellowkey MLS ID: A4661996
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2745 Built: 2012 Tax: $21,270 (2024)Community: Nichols Sarasota HeightsSpa: NoSingle Family
Taxes:$21,270
Remarks: One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafés, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside Elementary district, the property offers a private oasis with a sun-soaked southern-exposure backyard—ideal for all-day light on the pool and covered patio. Outdoor living shines with a heated pool featuring a sun shelf, fire pit, landscaped lawn, and inviting front and back porches designed for effortless entertaining. Inside, nearly 2,800 square feet unfolds with a wood-burning fireplace, tile and luxury vinyl plank flooring, and a flexible layout suited for today’s lifestyle including a den/office that can easily be used as a fourth bedroom. The oversized laundry/mudroom streamlines daily life, while the two-car garage with extra storage adds convenience. The spacious primary suite opens directly to the pool and features dual walk-in closets and bath with double vanities, a walk-in shower, and soaking tub. Built with quality in mind—including block construction and a durable metal roof—this home offers peace of mind and enduring value. A rare opportunity to own newer construction West of Trail with accessibility, abundant natural light, and room to live the Sarasota lifestyle to its fullest—just minutes from downtown.
Listing Agent: Katy Mcbrayer (941-400-2406)
251 SOUTHWINDS DR, SARASOTA, FL 34231
$149,500242 Days on yellowkey MLS ID: A4669553
REDUCED by $10,400 (6.5%) on 04/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 624 Built: 1963Monthly Fee: $195 Tax: $1,434 (2024)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,434
Remarks: Want to live near Siesta Key without breaking the bank? Here is your opportunity, in one of the most desirable 55+ co-op communities, South Winds! And for only $195/month for HOA fees, you get to enjoy maintenance free living in a friendly and active neighborhood with a heated pool, shuffleboard, bocce, pickleball, horseshoes, a putting green, library and recreation hall and more! The home features newly screened in lanai's on both sides, an attached storage shed and an oversized lot, one of the best in the entire community with green space in the front, a garden area in the back, and just a short distance to all amenities. The bathroom is also recently remodeled with granite counter, and a new walk in shower. AC new in 2020, and the home was re-piped in 2022. There is also a termite warranty and contract that conveys to the new owner! Here is your opportunity to live just 5 minutes to Siesta Key and 10 minutes to downtown Sarasota. Gulf Gate is also just 5 minutes away for amazing local restaurants and entertainment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Adrian Mociran (941-302-8603)
1678 STARLING DR #102, SARASOTA, FL 34231
$305,000155 Days on yellowkey MLS ID: A4678531
REDUCED by $20,000 (6.2%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1712 Built: 1989Monthly Fee: $167 Tax: $4,077 (2025)Community: Landings South Vii, The LandingsCondo
Taxes:$4,077
Remarks: One or more photo(s) has been virtually staged. Come live the Landings lifestyle. A sleek clean design awaits you in this first floor two bedroom, two bath condominium. An open plan with consistent flooring throughout and a neutral color pallet. A contemporary styled kitchen with white cabinetry, sleek black granite, white subway tile backsplash, and a stainless-steel appliance package. The primary bedroom is oversized with ample space for an office or exercise area. The ensuite bathroom has also enjoyed a makeover with travertine flooring and shower surround, dual sinks, the kitchen aesthetic has been repeated with clean white cabinetry and black granite. The guest bath has also been upgraded with new vanity, countertop, and sink. A private patio overlooking lush greenery is accessible via sliders from the eat-in kitchen and/or great room. A single car garage, opportunity for a larger pet, and immediate rental options are features of Landings South VII. Should you be looking to find a community where you can meet people-look no further than the Landings Racquet Club with eight har-tru tennis courts, heated pool and spa, exercise room, and activities for all occasions. The social calendar keeps members busy and is a great place to make friends. The Landings also has a nature Trail leading to a fishing pier/gazebo with storage area for kayaks. The Landings, a gated neighborhood located “west of the trail” is truly unique with its proximity to the revitalized Landings Shopping Center, Siesta Key, and downtown Sarasota.
Listing Agent: Judy Greene (941-350-0451)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.