Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
2572 JEFFERSON CIR, SARASOTA, FL 34239
$749,00018 Days on yellowkey MLS ID: A4693524
REDUCED by $26,000 (3.4%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1434 Built: 1972 Tax: $6,795 (2025)Community: South GateSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,795
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: This TURN-KEY sought-after CITY LIMITS gem is situated on a large 0.22 acre lot with an oversized 1 stall garage! Step inside this beach inspired, open concept beauty that is filled with natural Southern exposed light. Luxury vinyl flooring flows throughout, while the well-appointed kitchen features quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining. The French doors invite you to a private fenced backyard retreat that boasts a new heated sun-shelf pool with an expansive paver deck to lounge. Recent updates provide you with peace of mind! Accordion shutters and a new electrical service have been installed. No cast iron here! Plumbing and supply lines have been replaced! Weekly rentals are allowed so don't miss this TURN-KEY opportunity within the City Limits! This home serves as the prime gateway to a vibrant, active lifestyle with a wide array of local amenities right at your fingertips! Arlington Park's walking trails, basketball, tennis, outdoor fitness stations, and the aquatic center are all within half a mile! The beaches, downtown, arts, dining scene and highly rated schools are only minutes away – all within one of the most desirable City limit’s neighborhoods, and no HOA fees!!!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Kari Klein (941-961-7419)
2654 GRAND CAYMAN ST, SARASOTA, FL 34231
$367,0007 Days on yellowkey MLS ID: A4694859
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1959 Tax: $2,737 (2025)Community: Bahama HeightsSingle Family
Taxes:$2,737
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Remarks: One or more photo(s) has been virtually staged. Step into this move-in ready 2-bedroom, 2-bath home just minutes from world-famous Siesta Key and downtown Sarasota with no HOA restrictions! Enjoy the ultimate Florida lifestyle with top-rated schools and restaurants all within short distance, including Riverview High School and Phillippi Shores Elementary School. The open-concept living area features beautiful hand-painted ceiling details, abundant natural light, and a warm atmosphere perfect for relaxing. Major upgrades include a 50-year metal roof (2019), upgraded windows, new hot water heater (2025), upgraded kitchen and primary bathroom, and fresh interior paint (2026). High and Dry no flood insurance required! Schedule your private showing today! Move-in ready. List agent is owner.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mary Birkhold (941-266-8679)
409 N WASHINGTON DR, SARASOTA, FL 34236
$1,690,00014 Days on yellowkey MLS ID: A4693984
1 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1682 Built: 1952 Tax: $11,959 (2025)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$11,959
Remarks: What if you could own a fully renovated beach house on St. Armands Circle for the price many buyers are paying for an outdated condo… while being surrounded by $3M-$10M homes just blocks from the Gulf? Welcome to 409 N Washington Drive, an exceptionally rare opportunity to own one of the least expensive fully renovated homes to become available on St. Armands in years. Perfectly positioned just two blocks from the world-famous boutiques, restaurants, and cafés of St. Armands Circle, and only three blocks from the beautiful beaches of Lido Key, this charming single-story bungalow captures the kind of lifestyle most only experience on vacation. And here, vacation never has to end. Tucked away on one of the quietest streets on the Key, this beautifully updated 2-bed, 2-bath residence spans about 1700 SF and has been thoughtfully designed to deliver effortless coastal living with a resort-style feel. Lush tropical landscaping creates a sense of privacy rarely found this close to the beach and Circle, while multiple outdoor patios, lounging areas, and a sparkling resort-style pool invite year-round indoor-outdoor living and entertaining. Behind the charming exterior is a completely updated residence designed for effortless ownership, low-maintenance living, and maximum enjoyment. The home has undergone extensive renovations including updated PVC plumbing, updated electrical systems, hurricane-rated impact windows and doors, renovated kitchen and bathrooms, upgraded flooring, modern finishes, updated appliances, and refreshed indoor-outdoor living spaces. Every detail was intentionally curated to create a bright, inviting atmosphere that feels relaxed, elevated, and move-in ready from day one. Unlike many older island properties that become renovation projects disguised as opportunities, 409 N Washington removes the uncertainty, expense, and disruption buyers often fear when purchasing near the coast. There is no looming “what will break next?” anxiety here. The heavy lifting has already been done. For investors, this property checks nearly every box that drives premium short-term rental performance: an iconic walkable location, proximity to the beach, strong luxury rental demand, a fully furnished turnkey setup, and a proven St. Armands address that has historically outperformed many Sarasota County markets in appreciation and desirability. Offered furnished, including household goods, linens, décor, and months of future bookings in place, this is the type of property capable of generating strong occupancy with minimal downtime while also serving as a long-term appreciation play in one of Florida’s most supply-constrained markets. For lifestyle buyers, the appeal becomes even more personal. Imagine morning walks to coffee on the Circle, afternoons at Lido Beach, sunset dinners without needing a car, and evenings entertaining poolside after a day on the water. Whether used as a seasonal retreat, a lock-and-leave second home, or a full-time residence for a buyer seeking a lower-maintenance alternative to condominium living, this home delivers the rare combination of freedom, convenience, privacy, and coastal charm. In an area where many properties require extensive updating or command significantly higher prices, this home represents a rare opportunity to own a turnkey St. Armands residence with lifestyle appeal, income potential, and long-term investment strength wrapped into one exceptionally charming property.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Carlo Salerno (305-619-1803)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000335 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000130 Days on yellowkey MLS ID: A4678951
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Under contract-accepting backup offers. Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
7113 ANTIGUA PL, SARASOTA, FL 34231
$429,00020 Days on yellowkey MLS ID: A4693104
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1378 Built: 1968 Tax: $3,716 (2025)Community: Gulf GateSingle Family
Taxes:$3,716
Elementary School: Gulf Gate Elementary
Remarks: Nestled in the desirable Gulf Gate community, this meticulously maintained home features 2 bedrooms, 2 baths, and a spacious 2-car garage, making it an ideal retreat. The property boasts numerous upgrades, including new hurricane impact windows adorned with Bahama shutters and stylish awnings, ensuring both beauty and protection. Enjoy the tranquil ambiance of the peaceful koi pond, accompanied by a large screened-in lanai—perfect for outdoor gatherings or morning coffee. The fully fenced yard provides privacy and a safe space for pets and children to play. With fresh paint inside and out, the home exudes a bright and welcoming atmosphere. The newer HVAC system guarantees year-round comfort, while the pavered driveway adds to the home's charm. The raised raised flower beds will invite your gardening creativity. Location is key, and this home is just minutes away from the stunning Siesta Key Beach and all the vibrant offerings of Sarasota, from shopping to dining. This is a must-see—don’t miss your chance to own this remarkable property! Schedule your showing today!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
7366 POINT OF ROCKS RD, SARASOTA, FL 34242
$26,000,000146 Days on yellowkey MLS ID: A4673754
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 10600 Built: 2020 Tax: $115,958 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$115,958
Remarks: Rising above an enviable stretch of shoreline, this Gulf-front estate showcases timeless architecture and coastal refinement. Designed by CMSA Architects and completed in 2020, the residence features layered rooflines, sculpted stone staircases, and soaring arched windows across more than 180 feet of Gulf frontage. With 10,600 square feet of interiors and 20,982 square feet in total, the home offers a grand yet effortless indoor–outdoor lifestyle, ideal for both elevated entertaining and daily living. A sweeping motor court, mature palms, and a grand double staircase create an immediate sense of arrival. Inside, natural light and uninterrupted Gulf vistas establish a feeling of calm, scale, and sophistication from sunrise to sunset. The great room, lined with floor-to-ceiling arched windows and anchored by a carved-stone fireplace, delivers both serenity and architectural presence. The main kitchen is a triumph of craftsmanship - featuring custom Campbell cabinetry, quartz countertops, designer lighting, Sub-Zero refrigeration, a Wolf six-burner dual-oven range, and a substantial island that anchors the open flow into the living and dining spaces. A prep kitchen and workspace elevate functionality with premium appliances, expansive storage, quartz counters, and a dedicated gift-wrapping wall. The bar and wine room create a refined entertaining destination, defined by custom cabinetry and designer lighting. An iron-and-glass–enclosed, temperature-controlled wine room serves as the focal point, complemented by adjacent illuminated display shelving. Sub-Zero refrigeration, an ice maker, and a Fisher & Paykel dishwasher drawer complete the space. Outdoors, the estate unfolds across three dramatic tiers of Gulf-facing living, featuring arched loggias and a resort-style alfresco kitchen with a wraparound bar that opens seamlessly to the main living spaces. An elevated infinity-edge pool and spa appear to merge with the Gulf, while thoughtfully designed outdoor areas transition effortlessly to a manicured lawn and direct access to the crystal-clear waters at Point of Rocks—where snorkeling, dolphin sightings, and sunset walks become part of daily life. The primary suite forms a private wing, introduced by an illuminated groin-vault corridor that enhances the home’s architectural rhythm. Gulf views fill the bedroom and its terrace, while the bath offers a symmetrically designed retreat with dual vanities, full-height mirrors, multiple chandeliers, a massive double-entry shower, a stone-surround soaking tub, a Sub-Zero–equipped coffee bar, and two exceptional custom closets. Nearby, the office provides a quiet, light-filled workspace. The upper level is devoted to comfort and privacy, offering four well-appointed guest suites, a spacious family room with a wet bar, multiple terraces capturing Gulf views, an additional office, and a laundry room. The ground level is enhanced by indoor–outdoor walkways connecting multiple spaces and generous storage, reinforcing the effortless, resort-style livability. A generator, 3-stop elevator, 6-plus humidity-controlled garage spaces, floor-to-ceiling shades, linear vents, whole-house automation, and shellstone and French oak flooring complete the offering. A short, shaded, tree-lined walk places you at Siesta Key Beach, the No. 1 beach in America by TripAdvisor, offering effortless access to one of the world’s most iconic shorelines.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1800 WEBBER ST, SARASOTA, FL 34239
$4,790,00022 Days on yellowkey MLS ID: A4693157
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3262 Built: 2025 Tax: $12,950 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$12,950
Remarks: Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of Southside Village. Enjoy the convenience of a circular driveway with a custom paver design and garage space for three cars. With striking architecture, impeccable craftsmanship, and beautiful, thoughtfully curated finishings—showcasing detailed trim work and refined design throughout—this residence delivers sophistication and all-inclusive resort-style living in one of the area’s most desirable locations. Inside, soaring 18-foot vaulted ceilings and custom tray ceilings enhance the open-concept layout, while 12-foot full pocket sliders seamlessly connect indoor and outdoor living spaces. The living room is anchored by a sleek fireplace, creating a warm yet modern focal point. The chef’s kitchen is equipped with professional-grade gas appliances, a waterfall-edge quartz island, custom cabinetry, and an expansive butler’s pantry for effortless entertaining. A glass-enclosed wine display and tray ceiling details add dramatic appeal. The primary suite features 14-foot ceilings and a spa-inspired bath with a freestanding soaking tub, dual vanities, and a luxurious walk-in shower. All bedrooms include custom California Closets. A designated large office, spacious laundry room, and private gym complete the interior amenities. The home also has a full security system installed. Outdoors, the resort-style backyard showcases a heated saltwater pool and hot tub spa with elegant water features. The back patio, finished with a Brazilian hardwood ceiling, is enhanced with remote-controlled mosquito blinds with sun protection for year-round comfort, as well as a full sound system that can be app controlled. A fully equipped outdoor kitchen, fire pit, and outdoor SunBrite TV create the ultimate entertaining space, while a private putt-putt golf course adds a one-of-a-kind touch to this exceptional property. Please let us know how we can help and give us a call to set up a tour of this beautiful home. Thank you.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000273 Days on yellowkey MLS ID: A4663880
REDUCED by $50,000 (3.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $10,071 (2025)Community: TerraceCondo
Taxes:$10,071
Remarks: One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops, modern cabinetry, and stainless appliances. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mickey Kiernan (941-402-9115)
850 S TAMIAMI TRL #207, SARASOTA, FL 34236
$198,00025 Days on yellowkey MLS ID: A4692567
4 Days Off yellowkey (back on 5/26/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 576 Built: 1997 Tax: $793 (2024)Community: Central Park Sec 2 Ph 1Condo
Taxes:$793
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Discover this charming condominium located in downtown Sarasota, nestled in Central Park 2. Enjoy a range of amenities, including tennis courts, a heated pool and spa, a BBQ area, bike and kayak storage, a fitness-equipped clubhouse, a private deck, and a dock with a kayak launch for fishing and observing manatees. This ground-level unit features a cozy living room, a dining nook, a well-equipped kitchen with a bar, a full bathroom, and a washer and dryer. The unit has been remodeled with new kitchen cabinet doors, refinished countertops, updated light fixtures and fans, a new bathroom vanity, and a refinished bathtub. Relax on the screened lanai off the living room, where you can enjoy fresh air in a prime location near the Bayfront and downtown. Small dogs weighing up to 35 pounds are allowed. Schedule your showing today!
Listing is courtesy of: CENTRAL PARK REALTY CORP. (941-809-0034)
Listing Agent: Ross Bryans (941-809-0034)
4035 S SCHOOL AVE #B3, SARASOTA, FL 34231
$90,00012 Days on yellowkey MLS ID: N6144411
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 561 Built: 1972 Tax: $1,909 (2025)Community: Oakwood GardensSpa: NoCondo
Taxes:$1,909
Remarks: One or more photo(s) has been virtually staged. Discover the perfect blend of convenience, comfort, and investment potential in the heart of one of Sarasota’s best areas – just minutes from everything you love about this vibrant coastal city, with highly rated schools nearby! This charming first-floor 1-bedroom, 1-bath condo features easy-care tile flooring throughout, a relaxing pool view, and is clean, freshly updated, and truly move-in ready. Centrally located in such a prime spot for the ultimate Sarasota lifestyle, it’s within 2-3 blocks to Trader Joe’s and the newly built Bath & Racquet Residences & Club with limited public memberships to the fitness center, pool, pickleball, and tennis courts. Plus, it’s less than 2 miles to world-famous Siesta Key and a quick drive to Sarasota Memorial Hospital and downtown Sarasota. Enjoy community perks like a sparkling community pool, assigned parking plus ample guest spaces. Low-maintenance living with HOA fees covering: common area maintenance and taxes, community pool, reserve fund, cable, water/sewer, internet, pest control, and more essentials for worry-free ownership! All ages welcome – no restrictions! There is a reserved parking space (#16) and community laundry room, both are located by the community mailboxes. Fantastic rental opportunity: No waiting period to lease, with a quick rental approval required, and a 6-month minimum lease. The Reality Staged furniture and decor is available for a buyer to purchase direct from the vendors. A link to purchase the items can be made available. Don’t miss this rare opportunity to own a $90k gem in a prime location!
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
35 SANDY COVE RD #2A, SARASOTA, FL 34242
$925,000245 Days on yellowkey MLS ID: A4653716
REDUCED by $50,000 (5.1%) on 05/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1254 Built: 1970 Tax: $7,373 (2025)Community: Sandy CoveCondo
Taxes:$7,373
Remarks: Sandy Cove – Mid-Century Modern Gulf Front Paradise: Period-preserved mid-century architecture meets breathtaking Gulf front water views in this exceptional Siesta Key residence. Located in Sandy Cove, a hidden gem and distinguished 1970s development of villas and mid-rises, this fifth-floor residence offers a panoramic vista over Big Pass to Lido, Bird Key, and downtown Sarasota—a guaranteed "wow" moment. Sandy Cove Condos was designed in 1969 by Frank Folsom Smith with James Holliday and James Durden, earning a 1970 AIA Florida Award for architectural excellence. This light-filled, architecturally preserved residence is over 1,200 square feet with two bedrooms, two bathrooms, and a thoughtful split floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home. Step inside and be captivated by the spectacular living room featuring soaring vaulted ceilings that provide ample natural light and an airy, open ambiance. Enjoy breathtaking Gulf water views from your living room and kitchen sliders, which open seamlessly to your private patio. The sliders pull back to welcome Gulf breezes throughout the entire residence, connecting to several delightful porches and patios—including an additional private palm tree patio with IPE decking. A rare and highly coveted feature: this residence includes a private one-car garage. Gulf front residences in Sandy Cove rarely become available, making this a unique chance to own a piece of Siesta Key's architectural history. The home has potential to be sold furnished and is offered in as-is condition, presenting an opportunity for buyers to customize their personal vision. Ideally situated close to Siesta Key Village—just a short distance away, this truly unique location offers a natural private beach exclusive to the community, along with a fishing pier. Come see this truly "if you know, you know" treasure on Siesta Key.
4304 MIDLAND RD, SARASOTA, FL 34231
$340,00034 Days on yellowkey MLS ID: TB8502989
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)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00036 Days on yellowkey MLS ID: A4690742
REDUCED by $35,000 (5.0%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1439 Built: 1960 Tax: $6,132 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,132
Remarks: A rare offering within Sarasota’s desirable South Gate community, this meticulously restored Atomic Ranch embodies the essence of authentic Mid-Century Modern design. Revered as one of the foundational architectural styles of the 20th century, this residence has been thoughtfully preserved and elevated by discerning owners who understood the importance of honoring its original integrity. Ideally positioned in the heart of Sarasota, the home offers effortless access to world-class beaches, premier shopping and dining, top-rated schools, Sarasota Memorial Hospital, and the vibrant downtown district. The residence unfolds with a seamless, open-concept design, featuring three spacious bedrooms and two bathrooms, an inviting eat-in kitchen area, and expansive living areas designed for both comfort and entertaining. Walls of vintage sliding glass doors dissolve the boundary between indoors and out, opening to a generous pool terrace. Both covered and open-air, this creates a true indoor-outdoor lifestyle synonymous with classic Florida modernism. Authentic details remain beautifully intact, including original terrazzo flooring throughout, vintage architectural elements, and curated mid-century finishes that speak to the home’s heritage. An oversized garage, along with substantial fenced exterior space, provides flexibility for additional parking, including room for a boat or recreational vehicles. The home has been featured on Sarasota’s renowned “MOD Tour,” celebrated for its originality and preservation. As noted during the tour, the residence showcases vintage sliding glass walls, vibrant period kitchens and baths, and a fluid connection to the pool area. Carefully selected furnishings that reflect the era enhance the spirit of 1960s design. This is a truly special opportunity to own a piece of architectural history. Thoughtfully restored, exceptionally located, and ready to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
1404 KENILWORTH ST, SARASOTA, FL 34231
$5,200,000138 Days on yellowkey MLS ID: A4672697
REDUCED by $450,000 (8.0%) on 04/06/2026
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5428 Built: 2007Monthly Fee: $333 Tax: $52,740 (2024)Community: Oyster Bay LandingsSpa: YesSingle Family
Taxes:$52,740
Remarks: Privately positioned in gated Oyster Bay Landings with water views stretching down a short canal to Sarasota Bay, this stunning iconic masterpiece from world-renowned architect Guy Peterson is a breathtaking example of the Sarasota School of Architecture’s style and vision. A comfortable modernistic ambiance flows freely throughout the 5,428 sq. ft. of open living where walls of glass capture spectacular displays of the cerulean blue water and evening skies of fiery beauty. No detail has been overlooked. No expense has been spared. Architecturally striking, this 4-bedroom, 4.5-bath waterfront residence is the ultimate indulgence offering rarity, cachet and grandeur. Dock with 2 lifts is conveniently situated on a waterway unencumbered by any bridge. Floor to ceiling windows frame expansive vistas and abundant natural light complements the thoughtfully-appointed and expertly-planned space. Over 4,000 square feet of outdoor area is inviting and festive, and presents unique vantage points to deliver an exhilarating experience. Expansive terraces promote seamless indoor-outdoor living. Covered entertaining is abundant among the verdant tropical gardens and immaculately manicured grounds. Resort-style amenities including an elevator, courtyard with fire pit and heated pool/spa, and breathtaking reflecting pool with fountain. The stunning kitchen is a culinary delight and complemented by an extravagant amenities package of top-tier appliances, island with seating for 6, 20-ft. long counter for 2 desk workstations, side-by-side but separate refrigerator and freezer, 2 dishwashers, and deep walk-in pantry. The family room is equipped with built-in entertainment wall and opens to a waterfront patio with outdoor cooking center. The great room has travertine floors and cypress ceiling detail, and the office provides a desk with stone countertops and plenty of solid wood cabinetry. A 400-bottle wine room is the highlight of the gaming area with wet bar, electric shades and unique glass chandelier. On the second level are spa-inspired en-suite bedrooms with custom closet systems and elevated ceilings. A 30-ft. bridge leads to the master wing highlighted by incredible water views, sitting room with morning bar, and home gym/office. The primary bath creates an immersive experience with a 16-ft. long dressing hall with a wall of built-ins and mirrors, large walk-in specialty closet, multi-faceted shower, deep soaker Jacuzzi tub, separate bidet and laundry chute. In addition, there are two laundry areas, an elevator from ground level to the 2nd and 3rd floors, Creston music and lighting system, Generac generator, and 4-car garage. In one of Sarasota’s most coveted locations along the waterfront, this home redefines coastal living is just minutes from beaches, golf, fine dining and downtown Sarasota’s beloved arts and cultural offerings. When scheduling your exclusive tour of this amazing MODERN waterfront estate, make sure to allow plenty of time for exploring its incredible features, both inside and out. It must be seen in person to be fully appreciated. Even the most discerning buyer will fall in love!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
2989 GREENBRIAR ST, SARASOTA, FL 34237
$445,00021 Days on yellowkey MLS ID: TB8507802
2 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1237 Built: 1956 Tax: $843 (2025)Community: Greenbriar Homes 1St AddSingle Family
Taxes:$843
Elementary School: Alta Vista Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated TRUE MID CENTURY MODERN three-bedroom, two-bathroom home in Sarasota, where modern upgrades and thoughtful design come together to create a move-in-ready retreat. With a 2021 water heater, 2019 AC, and updates throughout the entire home, including brand-new luxury vinyl plank flooring, a completely renovated kitchen and bathrooms, new fixtures, and fresh landscaping, this property offers stylish living inside and out. An inviting, large front porch and new front door welcome you into a light and bright interior featuring an open floor plan. The spacious living room and dining room combination flows seamlessly into the stunning brand-new kitchen, designed with both functionality and style in mind. The kitchen features stainless steel appliances, a striking waterfall peninsula, new backsplash, and modern cabinetry, creating the perfect space for cooking, entertaining, and gathering. Both bathrooms have been fully renovated with new vanities, mirrors, lighting, and beautifully tiled showers with updated hardware. The primary suite offers double closets for ample storage and a private en-suite bathroom with a modern tiled shower, a lighted mirror, and new vanity. The additional bedrooms are nicely sized and share a fully updated bathroom with a tub/shower combination. Modern ceiling fans throughout the home add comfort, while the open layout enhances the bright, airy feel of the living spaces. Outside, enjoy a large fenced backyard with plenty of room for outdoor entertaining, gardening, or relaxing in the Florida sunshine. The home also features carport parking and additional storage space with A/C, providing flexibility for hobbies, storage, or workspace. Ideally located close to parks, dining options, and zoned schools, this home is also just 20 minutes from the vibrant shopping and dining of St. Armands Circle and the beautiful sands of Lido Key Beach. Enjoy the perfect combination of modern upgrades, comfort, and convenient Sarasota living. Schedule your showing today!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Ryan Scott (410-402-3550)
2156 ORCHID ST, SARASOTA, FL 34239
$899,000279 Days on yellowkey MLS ID: A4663262
REDUCED by $51,000 (5.4%) on 05/26/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1850 Built: 2024 Tax: $3,119 (2024)Community: South GateSpa: YesSingle Family
Taxes:$3,119
Remarks: If you’re looking for a true “wow” factor, this stunning new-construction residence delivers. This custom-designed home combines luxury finishes with thoughtful functionality. Step inside to soaring 16-foot ceilings and dramatic exposed beams in the great room, creating an impressive sense of space. The chef’s kitchen is the centerpiece, featuring a striking brown agate back-lit island, granite countertops, modern cabinetry with pullouts and utensil organizers, an eight-burner professional range with bread and baking oven, custom vent hood, and upscale appliances—perfect for entertaining. Throughout the home, you’ll find large-format tile floors, custom window treatments, and the option to purchase designer furnishings. Offering 3 spacious bedrooms and 2.5 baths, this residence blends style and comfort seamlessly. Outdoor living is just as impressive, with a brand-new modern pool and pool cage (completed August 2024), a Jacuzzi brand hot tub, and a private outdoor shower with hot and cold water. The property is professionally landscaped, freshly painted inside and out (August 2025), and boasts impact windows and doors, ensuring safety, efficiency, and some of the lowest homeowners insurance rates available. Additional highlights include a tankless gas water heater, gas and electric dryer connections, and no flood zone location. Situated on one of Sarasota’s highly coveted “Flower Streets,” this property offers rare flexibility: the City of Sarasota permits 7-night minimum rentals, and the home is not subject to Southgate deed restrictions. Just 1 mile south of Sarasota’s luxury waterfront downtown, and less than 3 miles to the world-famous Siesta Key Beach, the home is also walkable to Conner’s Steakhouse, Baker & Wife, shopping, dining, banks, and groceries—all tucked away on a quiet dead-end street.
Listing is courtesy of: CLUB REALTY (941-726-2677)
Listing Agent: Brooke O'Malley (941-726-2677)
3000 SOUTHWEST DR, SARASOTA, FL 34239
$12,750,000190 Days on yellowkey MLS ID: A4672971
REDUCED by $500,000 (3.8%) on 04/30/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 8125 Built: 2003 Tax: $109,050 (2025)Community: Cherokee ParkSpa: YesSingle Family
Taxes:$109,050
Remarks: One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional seclusion and privacy, surrounded by lush, verdant landscaping, specimen trees and mature oaks, with tranquil water views providing a serene backdrop throughout the entire home. A masterpiece by design, this architectural gem was designed by esteemed architect Clifford Scholtz and built with impeccable craftsmanship by Rich Perrone of Perrone Construction. Among the recent exterior improvements are a new roof and gutters, fresh exterior paint, new decorative landscape lighting, and a refreshed outdoor shower. Inside, thoughtfully curated modern finishes and updates seamlessly blend with classic architectural details such as columns, archways, and a mahogany-paneled office, creating interiors that feel bright, open, and timeless. New European white oak flooring flows through the main living areas, while Stark carpeting adds warmth to the staircase, select bedrooms, and the bonus room. A culinary enthusiast’s dream, the completely updated kitchen boasts Taj Mahal leathered stone countertops, White Haze dolomite backsplash, a micro cement hood, painted cabinetry, an oversized island, new sinks and faucets, a Sub-Zero fridge/freezer, and more. The charming breakfast area and adjacent family room, featuring a new micro cement fireplace with Taj Mahal hearth, are set against a backdrop of expansive windows and glass doors that capture picturesque bay views. A luxurious and peaceful retreat, the elaborate primary suite features a beautifully updated bath showcasing new vanities with Taj Mahal countertops and Brizo fixtures, plus new flooring, soaking tub, and walk-in shower. Secondary baths throughout the home have also been refreshed. Covered patios and loggias extend from the main living areas, creating ideal spaces for relaxation and enjoyment. Upstairs, the expansive gathering room impresses with its custom Perla Venata quartzite bar, freshly painted ceiling beams, large windows, and balcony access overlooking the bay, pool, and lush grounds. This is the perfect perch to enjoy large gatherings, relax at the bar, shoot pool, or have friends and family over on game day. Outside, the property unfolds as a private oasis, with a screened porch featuring Chicago brick pavers, a Wolf gas grill, Sub-Zero fridge, and refreshed finishes including a tiled backsplash, updated hardware, new sink and faucet, and refinished cabinetry. Chicago brick pavers also surround the free-form pool, creating a cohesive outdoor living environment. At the water’s edge, boaters will delight in the protected deep-water boat basin with two lifts (10,000-lb. and 16,000-lb. capacities), providing effortless maritime adventures. A detached oversized 3-car garage, connected by a covered walkway, provides ample space for storage or workshop use. Additional updates of note include updated HVAC systems, tankless water heaters, and modernized electrical throughout. A whole house generator rounds out the superlative systems. This exquisitely updated estate represents a rare offering where timeless elegance meets modern sophistication on one of Sarasota's most extraordinary waterfront settings.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
3317 PINE VALLEY DR, SARASOTA, FL 34239
$565,656275 Days on yellowkey MLS ID: A4663718
REDUCED by $9,344 (1.6%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 1964 Tax: $4,160 (2024)Community: Frst Lakes Country Club EstatesSingle Family
Taxes:$4,160
Remarks: REMODELED SPACIOUS OPEN FLOOR PLAN IN FOREST LAKES COUNTRY CLUB CLOSE TO GOLF COURSE THIS CLASSIC FEATURES A NEW KITCHEN WITH A TON OF SHAKER CABINETS AND QUARTZ COUNTER TOPS. ALL NEW STAINLESS APPLIANCES INCLUDING A KITCHENAIDE FRENCH DRAWER REFRIGERATOR.THE REMODEL INCLUDED NEW HURRICANE RATED WINDOWS THROUGHOUT AND A NEW BARREL TILE ROOF. THE INTERIOR IS FRESHLY PAINTED AND HAS ALL NEW DOORS. THE FLOORS FEATURE A MODERN WOODLIKE LAMINATE WHICH GIVES THE INTERIOR A WARM COZY FEEL. BATHROOMS WERE UPDATED WITHOUT NEW VANITIES SHOWER TILE AND STYLISH ARMITAGE AQUA FIXTURES. THE INTERIOR HAS MANY 54" CASA SALERNO CEILING FANS. HUGE FAMILY ROOM WITH FIVE PICTURES WINDOWS OVER LOOKING A SHADY BACKYARD BRINGS A TOUCH OF NATURE INSIDE.THIS EKEGANT HOME ALSO FEATURES A NEW TANKLESS HOT WATER HEATER, NEW LANDSCAPING BEDS, MYRAID OF CLOSET SPACE AND FRESHLY PAINTED EXTERIOR. THE ONLY THING MISSING IS YOU AND YOUR FRUNITURE!!
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
440 MEADOW LARK DR, SARASOTA, FL 34236
$11,300,000246 Days on yellowkey MLS ID: A4666605
1 Days Off yellowkey (back on 5/12/2026)
Bed: 4 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6880 Built: 2023Monthly Fee: $110 Tax: $82,533 (2024)Community: Bird Key SubSpa: YesSingle Family
Taxes:$82,533
Remarks: A breathtaking fusion of architectural brilliance and design sophistication, 440 Meadow Lark Drive is arguably the finest residence ever constructed in Sarasota. Envisioned by the masterful minds of architect Clifford Scholz and Voigt Brothers Construction, this custom estate is a testament to elevated living where no detail has been spared. From the moment you approach the bespoke exterior elevations, crafted to distinguish with striking individuality you realize this is not merely a home, but a work of art. Step inside to discover nearly 7,000 square feet of flawlessly curated interiors where each room tells a story. Italian oak floors, Gucci, Phillip Jeffries, and Holly Hunt wallpapers, and SAWW’s custom cabinetry set the tone for refined elegance. Every room is inspired by the glamor of Kelly Wearstler’s Hollywood Regency style and brought to life by renowned designer Christiana Engert, while the entire home functions as a smart residence, seamlessly blending intuitive technology with timeless luxury. At the heart of the home, the kitchen is both showpiece and workspace, featuring Dolomite marble counters with protective tough-skin, double dishwashers, Wolf, Sub-Zero, and Miele appliances, and a hidden pantry with display cabinetry, wine chiller, and artwork. The adjacent morning room is perfect for casual lounging, complete with custom cabinetry and a discreet TV. The living room exudes warmth with a Nero Marquina marble gas fireplace, generous seating, and captivating water views, while the dining room stuns with a one-piece luxe side table and a dramatic custom chandelier. Entertain effortlessly in the media room with surround sound, three TVs, and a custom bar. An adjacent butler’s pantry includes an additional refrigerator, washer/dryer, dishwasher, and concealed storage. The 1400+ bottle wine cellar is a masterpiece unto itself. With custom artistic designs, backlit lighting, and a commercial capacity cooling system, the one-of-a-kind space is perfect for the most discerning collector. The primary suite is a sanctuary of indulgence with hand-painted wallpaper, sweeping waterway views, and his-and-her closets with exquisite built-ins, chandelier, a marble island, and boutique-style jewelry displays. The spa bathroom features gold-leaf inspired tile, dual vanities, and indoor and outdoor showers. Ascend the single-piece staircase to the upper level, where guest suites are equally impressive with vaulted ceilings, en-suite baths, and private access to the second-floor entertainment terrace. A loft with clerestory windows, serving bar, and hidden storage provides flexibility as a guest lounge, office, or retreat. A separate-access guest suite doubles as an office or bonus room, with its own bath and dramatic architectural lines. Outdoors, resort-level amenities await. The lanai offers seamless indoor-outdoor flow through oversized sliders, a full outdoor kitchen, fireplace, and multiple seating areas beneath tongue-and-groove ceilings. Limestone pavers surround a saltwater pool and spa designed for comfort and elegance, while a 20,000 lb boat lift and 7,000 lb deck lift for kayaks or paddleboards make this an ideal waterfront escape. Stunning privacy landscaping by Michael A. Gilkey ensures serenity across the grounds. With concrete walls on both levels, an 8-inch concrete slab second floor, full-house generator, whole-house water softener, and natural gas, this estate combines enduring structure with breathtaking beauty.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Keith Redding (941-894-4216)
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