Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
465 E ROYAL FLAMINGO DR, SARASOTA, FL 34236
$4,850,0002 Days on yellowkey MLS ID: A4696960
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2846 Built: 1973 Tax: $39,161 (2025)Community: Bird Key SubSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$39,161
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Perfectly positioned on coveted Bird Key, 465 E Royal Flamingo Drive captures the essence of refined Sarasota waterfront living with an extraordinary full renovation that blends timeless coastal elegance with exceptional craftsmanship. Set along 100 feet of protected canal frontage with direct access to Sarasota Bay, this remarkable residence offers an unparalleled boating lifestyle complete with a private dock and 16,000-pound boat lift, creating the ideal setting for effortless days on the water. Encompassing 2,846 square feet of thoughtfully curated air-conditioned living space with four bedrooms and four beautifully renovated bathrooms, every detail of this home has been elevated to deliver a move-in ready luxury experience. Inside, Mirage engineered hardwood flooring flows seamlessly throughout, complemented by new interior and exterior lighting, recessed lighting, designer ceiling fans, and carefully selected finishes that create warmth and sophistication. The spectacular chef’s kitchen serves as the centerpiece of the home and features custom cabinetry with integrated lighting and soft-close doors and drawers, stunning quartzite countertops and backsplash, decorative tile accents, a custom hood, farmhouse sink, premium plumbing fixtures, separate water filtration faucet, Sub-Zero refrigeration with water and ice, wine refrigeration, and an exceptional Wolf appliance package including a six-burner gas range with grill, double convection wall ovens, and additional culinary conveniences. A beautifully appointed butler’s pantry and utility room enhance functionality with a Wolf microwave, KitchenAid ice maker, and Electrolux washer and dryer. Entertain effortlessly with a custom dry bar showcasing illuminated glass cabinetry, quartzite surfaces, and designer tile details. The great room is equally impressive, anchored by dramatic wood beam ceilings, an elegant electric fireplace, and custom built-ins with illuminated shelving that create an inviting yet elevated gathering space. The luxurious primary suite is designed as a private retreat with sliding glass doors opening to the lanai, a spacious custom walk-in closet, and a spa-inspired bath featuring a freestanding soaking tub, floating dual vanity, rain shower, niche detailing, and exquisite finishes of marble and porcelain. Outdoor living is equally exceptional with an expansive lanai finished in shell stone, tongue-and-groove ceilings, electric roll-down screens, and multiple entertaining spaces overlooking the heated saltwater pool and spa, beautifully resurfaced with glass waterline tile, a shell stone pool deck, and pergola. Additional highlights include a fully fenced and professionally landscaped yard with irrigation and landscape lighting, a new clay barrel tile roof completed in 2024, Aluminum ES impact windows and doors, natural gas service, Lennox air-conditioning, dual Rheem gas tankless water heaters, updated paint throughout, seawall enhancements with replacement panels, cap and tie-back system, and an oversized two-car garage featuring epoxy flooring, custom cabinetry, mini-split air conditioning, Tesla charger, and an exceptional level of finish rarely found. This is Bird Key waterfront living at its finest—where luxury, comfort, and effortless access to Sarasota’s world-class boating and downtown lifestyle come together in one extraordinary residence.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
3225 GULF WATCH CT, SARASOTA, FL 34231
$399,0001 Day on yellowkey MLS ID: TB8519650
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1216 Built: 1990Monthly Fee: $133 Tax: $3,345 (2025)Community: Gulf Gate GlenSingle Family
Taxes:$3,345
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Nestled within the desirable Gulf Gate Glen community, this location offers the perfect blend of convenience, recreation, and the laid-back Florida lifestyle that makes Sarasota so sought after. Residents enjoy being just minutes from the powder-soft sands of Siesta Key Beach, consistently ranked among the best beaches in the country. Whether you're spending the day boating on Sarasota Bay, exploring nearby waterfront parks, or taking in a breathtaking Gulf Coast sunset, this location places the very best of Sarasota right at your fingertips while remaining outside of a flood zone. Stepping inside, you'll immediately notice the soaring vaulted ceilings, abundant natural light, and luxury vinyl plank flooring that flows throughout the home. This well-designed floorplan offers 2 bedrooms, 2 bathrooms, and a spacious 2-car garage, creating the perfect balance of comfort and functionality. The kitchen features stainless steel appliances and overlooks a dining area, making everyday living and entertaining effortless. The owner's suite serves as a private retreat with a walk-in closet and an ensuite bathroom complete with dual sinks and a walk-in shower. French doors lead to the screened-in lanai, providing the ideal space to enjoy your morning coffee, unwind in the evenings, or entertain guests while enjoying Florida's year-round sunshine. One of the biggest advantages of living here is the everyday convenience. Gulf Gate Village is just around the corner, offering an eclectic mix of locally owned restaurants, coffee shops, bakeries, live music venues, and neighborhood bars that create a true sense of community. For shopping, dining, and entertainment, you're only a short drive from Downtown Sarasota, St. Armands Circle, and the countless cultural attractions that make Sarasota one of Florida's premier destinations. Outdoor enthusiasts will appreciate easy access to Legacy Trail, one of the area's most popular biking and walking trails stretching for miles throughout Sarasota County. Nearby parks, marinas, fishing spots, kayak launches, golf courses, tennis facilities, pickleball courts, and fitness centers provide endless opportunities to enjoy an active Florida lifestyle. Families will appreciate the proximity to highly regarded schools, while commuters benefit from quick access to US-41, making travel throughout Sarasota, Venice, and Lakewood Ranch simple and convenient. Sarasota Memorial Hospital, medical offices, grocery stores, and everyday necessities are all just minutes away. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional Sarasota location delivers the coastal lifestyle buyers dream about. Close to world-famous beaches, vibrant dining and entertainment, outdoor recreation, and everything that makes Florida's Gulf Coast so special, schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Bona Nedelkovska (727-238-6302)
9397 MIDNIGHT PASS RD #903, SARASOTA, FL 34242
$364,000Listed 06/18/2026 10:24PM MLS ID: A4696940
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 778 Built: 1975 Tax: $4,242 (2025)Community: Pointe On Midnight PassCondo
Taxes:$4,242
Elementary School: Phillippi Shores Elementary
Remarks: At the very end of Midnight Pass Road—where tranquility, water, and lifestyle take over. The Pointe is a private, gated, park-like condominium community situated on the southernmost tip of Siesta Key, where Midnight Pass Road ends and a remarkable waterfront lifestyle begins. Surrounded by water, wildlife, and natural beauty, residents regularly enjoy sightings of dolphins, manatees, pelicans, herons, egrets, and active osprey nests, while kayakers and paddle boarders quietly pass through the surrounding waterways. Set on more than five acres and surrounded by over 900 feet of seawall, The Pointe combines a private gated setting, Gazebo Island, boat slips, kayak launches, abundant wildlife, and immediate access to Sarasota Bay and the Gulf—an exceptionally rare combination of amenities and natural beauty found in very few condominium communities in Southwest Florida. Unit 903S is one of only 16 one-bedroom residences within the entire community and is currently the only available one-bedroom opportunity at The Pointe. Positioned on the 9th floor, the residence enjoys wonderful sunrise views over Little Sarasota Bay and evening sunsets toward the Gulf. During much of the year, fresh Gulf breezes flow naturally through the residence, creating the relaxed coastal lifestyle that attracts owners to Siesta Key. The residence has been thoughtfully refreshed and furnished in a clean coastal-contemporary style with designer furnishings selected through The Pamaro Shop. The presentation emphasizes light, openness, comfort, and surrounding water views while still allowing future owners the flexibility to personalize the residence according to their own tastes. The Pointe is recognized for its strong ownership structure, professional on-site management, and completion of all required post-Champlain engineering and structural requirements. Major building improvements have been completed and paid for, providing buyers with confidence in the community's long-term stewardship and financial stability. WATERFRONT LIFESTYLE & AMENITIES • Largest condominium swimming pool on Siesta Key (heated year-round)• 12-person in-ground spa• Tennis and pickleball court• Three BBQ and outdoor gathering areas, including the covered island gazebo• Boat slips available for owners• Kayak and paddle board storage racks and launch areas• Less than five minutes by boat or kayak to the Gulf via Midnight Pass• Private Gazebo Island with BBQ facilities and park benches overlooking mangrove preserves and Sarasota Bay• Multiple garden sitting areas and park benches throughout the property• Seawall features a lighted concrete waterfront walkway, ideal for morning walks, sunset strolls, fishing, wildlife viewing, and enjoying the ever-changing beauty of Sarasota Bay• The Cottage Community Center with fireplace, full kitchen, social gathering areas, and community events• On-site Property Manager, Maintenance Manager, Maintenance Technician, and fully equipped maintenance workshop. The Pointe maintains a three-month minimum rental policy, preserving a quiet, owner-oriented environment without constant short-term rental turnover. Whether enjoying morning coffee overlooking the Bay, a sunset over the Gulf, boating through Midnight Pass, or simply relaxing in one of Siesta Key's most peaceful waterfront communities, Unit 903S offers a rare opportunity to enjoy the very best of coastal Florida living.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Guia Tomelden-Dorion (845-321-5158)
6732 SARASEA CIR #104C, SARASOTA, FL 34242
$644,000149 Days on yellowkey MLS ID: A4679214
REDUCED by $5,000 (0.8%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 744 Built: 2009 Tax: $5,421 (2025)Community: Beach Club At Siesta KeyCondo
Taxes:$5,421
Remarks: Reduced over 55K! Excellent resort investment opportunity with a proven rental history at The Beach Club on Siesta Key, located just steps from the world-famous sugar-sand beach. This beautifully maintained residence looks and feels brand new, featuring a functional floor plan, deeded beach access, and a complete 2021 update with elegant sea-inspired décor, flat-screen TVs, free Wi-Fi, and a full kitchen with stainless steel appliances. Owners enjoy up to 120 days of personal use per year while benefiting from professional on-site management or the option to self-manage for added flexibility. TripAdvisor rates the property 4.5 stars with outstanding reviews. Resort amenities include a heated pool, hot tub, and complimentary beach chairs and umbrellas. Built in 2009 on stem walls, the building is elevated and sustained no storm damage. Ideally located mid-island just 1,000 feet south of the Stickney Point Bridge for easy mainland access, and within walking distance to popular restaurants, shops, marinas, rentals, and local favorites such as Captain Curt’s and Daiquiri Deck—making this a true turnkey beach getaway and income-producing investment. Ask your agent for the Rental History attached to the MLS listing too!
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Mike Winger (941-228-3390)
1415 S SCHOOL AVE, SARASOTA, FL 34239
$619,90066 Days on yellowkey MLS ID: A4687920
REDUCED by $40,000 (6.1%) on 05/12/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1126 Built: 1955 Tax: $6,276 (2025)Community: Loma Linda Park ResubSingle Family
Taxes:$6,276
Elementary School: Alta Vista Elementary
Remarks: Sarasota midtown oasis in desirable Arlington Park Neighborhood. This 3 bedroom, 1 1/2 bath, TURNKEY FURNISHED (OPTIONAL) BLOCK home situated on a secluded corner lot, immaculately maintained and updated, could be yours as a primary residence or income producing rental property (7 DAY MINIMUM RENTAL). New AC with warranty. Roof: new APOC 585 silicone coating, newer double pane insulated windows with custom shades, tankless hot water heater, updated plumbing, new stainless steel appliances, granite countertops, IKEA kitchen cabinets and closet organizers. Terrazzo floors throughout with tile in both bathrooms. Property is fully FENCED with 2 gates providing access and parking for a small boat, camper or vehicle. Screened lanai overlooks hardwood deck and tropical plant landscaped yard. The city easement (a non build lot) on the east side of the property provides additional privacy. NO FLOOD INSURANCE REQUIRED. Located 2 blocks east of Sarasota Memorial Hospital, 4 miles to Siesta Beach (#1 beach in the USA), 5 miles to Lido Beach and 1 mile to Sarasota’s downtown world class shopping and entertainment. Short walk to Southside Village, Midtown Plaza, Legacy Trail and the Arlington Park & Aquatic Center hosting Live Music Events Alongside Pickleball, Tennis, Basketball Courts, Playgrounds, a Dog Park, Walking Trails, and Two Pools. Magical must see property!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Wendy Lewis (941-993-5708)
2037 and 2039 Jo an Dr JO AN DR, SARASOTA, FL 34231
$619,00048 Days on yellowkey MLS ID: A4692288
REDUCED by $10,000 (1.6%) on 06/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 1988 Built: 1955 Tax: $5,534 (2024)Community: High AcresSpa: YesHalf Duplex
Taxes:$5,534
Tax Year: 2024
Remarks: Live the Florida Dream for Free – Premier Sarasota Duplex with Income Potential Why choose between a luxury home and a smart investment? At 2037 & 2039 Jo An Drive, you can have both. This meticulously maintained side-by-side duplex offers a rare opportunity to occupy a beautiful 2BR/2BA residence while the identical neighboring unit generates significant rental income to offset your costs. The Lifestyle: Enjoy your own private oasis featuring a luxurious swim spa and a massive, deep-bay garage perfect for boat storage—all just 3 miles from the world-famous Siesta Key Public Beach. The Income: With RMF-1 zoning, this property is a turnkey powerhouse. Whether you prefer stable long-term tenants or want to capitalize on the high-demand short-term rental market, the numbers work in your favor. The Location: Tucked away on a quiet street but only minutes from Southside Village, premier dining, and top-rated schools. Ideal for: The "House Hacker": Live in one side and let the other pay your mortgage. The Seasonal Resident: Live here in the winter and rent both units during the peak vacation season. The Savvy Investor: Maximize your ROI with two updated units in a prime coastal location. Don’t just buy a home—buy an asset. Contact us today for a private tour and a full rental income projection.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Marcus Mumm (920-960-0413)
2306 VALENCIA DR, SARASOTA, FL 34239
$1,210,00057 Days on yellowkey MLS ID: A4691100
REDUCED by $35,000 (2.8%) on 06/06/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1949 Built: 1955 Tax: $4,130 (2026)Community: South GateSingle Family
Taxes:$4,130
Tax Year: 2026
Remarks: Welcome home to the heart of Sarasota's Southgate neighborhood! This stunning, fully rebuilt residence blends modern comfort with timeless appeal. Featuring 3 bedrooms 2.5 baths, the home showcases a bright open-concept floor plan with 10 ft.ceilings creating a light and bright atmosphere throughout. The impressive kitchen features custom soft-close cabinetry, premium appliances, a dedicated bar area, and a spacious breakfast bar ideal for casual gatherings. The master bedroom has a spa inspired bathroom with generous closet space. Sliding doors throughout this lovely home invites you outdoors to your private oasis. The maintenance-free yard features a sparkling heated large pool and spa enhanced with a sunshelf. The shaded patio is perfect for relaxing and casual entertaining. Lush landscaping provides complete privacy enclosed by a full fence for your pets enjoyment too. Southgate is a well renowned sought after area located in the Southside School district, just a few minutes from Sarasota Memorial Hospital, down town area, and the beach. This amazing house could be your....."Home sweet Home"
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
2532 FRUIT TREE DR, SARASOTA, FL 34239
$2,375,00047 Days on yellowkey MLS ID: A4692314
Bed: 6 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 3931 Built: 2025 Tax: $3,561 (2024)Community: South GateSpa: YesSingle Family
Taxes:$3,561
Remarks: MOTIVATED SELLER. NEW HOME IN SOUTHGATE. Built with the perfect blend of elegance, and comfort this home has so many beautiful features for today's lifestyle and modern living. The perfect blend of elegance & comfort exudes this beautiful residence. The thoughtfully designed floor plan features a first floor open living space with soaring ceilings, lots of hurricane windows and sliding doors gives this beautiful home effortless indoor-outdoor living enjoyment and fills the home with natural light. The open concept chef inspired kitchen has plenty of custom soft-close cabinet space and drawer space. All accented with under mount lighting. The large breakfast bar is perfect for casual living and entertaining. The dining area encircled with windows overlooks the lovely landscaped yard and pool/spa. Sliding doors wrap around the house from every room to the great outdoors. The master suite includes a spacious spa inspired bathroom with soaking tub and large closet space. The elegant open staircase leads to the second floor with a gathering area and outdoor balcony in the front of the house. four additional bedrooms with bathrooms and walk in closets including a family room with sliders to an outdoor veranda overlooking the yard and pool completes the home.. There is also a laundry area located on the second floor! Masterfully planned and designed with your comfort and easy living in mind. This home is impressive, beautiful and a relaxing place to call home. Located in one of the most sought after locations in Sarasota. Close to the Sarasota Memorial Hospital, Selby Gardens, Van Wezel, Oslo, Down town restaurants and shopping. Your dream Your home....
2121 CLEMATIS CT, SARASOTA, FL 34239
$2,595,00030 Days on yellowkey MLS ID: A4692569
REDUCED by $180,000 (6.5%) on 06/18/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3881 Built: 2026 Tax: $3,632 (2024)Community: Arlington ParkSpa: YesSingle Family
Taxes:$3,632
Remarks: Not just another house but a carefully curated masterpiece by Segatto Property Solutions Inc. Come experience a blend of modern luxury, sophisticated design, and effortless Florida living in this stunning, newly completed custom residence. This move-in-ready, two-story block home offers four bedrooms and 4.5 baths plus an office, thoughtfully designed with impeccable attention to detail, soaring ceilings, and an open-concept layout ideal for everyday living and elevated entertaining. From the moment you enter, you’re greeted by 10-foot ceilings throughout, with dramatic 22-foot ceilings in the great room that create a grand, light-filled space. The office and primary suite also feature 12-foot ceilings, adding an extra layer of refinement and comfort. The designer kitchen is the heart of the home, showcasing quartz countertops, all Moen fixtures in bronze gold, and matte black, a premium KitchenAid appliance package, custom cabinetry, walk-in pantry, and an oversized island that flows seamlessly into the great room and dining areas. Expansive sliders open to the outdoor living space, delivering the ultimate indoor-outdoor lifestyle. Go outside to your fully fenced, private oasis featuring a heated saltwater pool, a fully equipped covered outdoor kitchen with grill and refrigerator, and an outdoor shower, ideal for entertaining or unwinding in total privacy. The first floor primary suite offers a spa-like retreat with luxurious finishes, generous space and a beautifully appointed bath, featuring dual shower heads, free-standing tub and an oversized walk-in closet. Upstairs, two additional en suites and a versatile loft area with a wet bar provide the ideal setting for a media room, lounge or guest retreat. Practicality meets luxury with a well-appointed first-floor laundry room featuring LG smart washer and dryer, additional built-in storage and a utility sink. Every detail of this home reflects quality craftsmanship and modern elegance, delivering the feel of a high-end model home without the wait. Ideally in Arlington Park, near shopping, dining, beaches and everything Sarasota has to offer, this exceptional home is ready for its first owners. Schedule your private showing today. Homes of this caliber, completed and move-in ready, are a rare opportunity.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Roberta Tengerdy, Pa (941-321-2292)
3215 PINE VALLEY DR, SARASOTA, FL 34239
$729,90016 Days on yellowkey MLS ID: A4695558
REDUCED by $20,000 (2.7%) on 06/18/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3299 Built: 1970 Tax: $8,106 (2025)Community: Frst Lakes Country Club EstatesSpa: NoSingle Family
Taxes:$8,106
Elementary School: Wilkinson Elementary
Remarks: Classic Estate-Style Home with Pool & Golf Course Views! Welcome to this stately 5-bedroom, 3.5-bath residence in Forest Lakes Country Club Estates, offering timeless curb appeal, generous living space and peaceful golf course views in the heart of Sarasota. Set on a spacious 0.37-acre lot, the home makes a lasting first impression with its classic brick-style exterior look, white columns, mature landscaping, circular brick driveway and ample parking, including additional driveway space along the side of the home. Inside, the grand two-story foyer showcases the home’s architectural character with a sweeping curved wood staircase, iron balusters, chandelier detail and elegant traditional design that sets the tone for the rest of the home. Thoughtfully refreshed, the home features a new shingle roof in 2026, fresh interior paint throughout and meaningful upstairs updates, including new LVP flooring throughout the upstairs hallway and bedroom areas. The main level features formal living and dining areas, a wood-burning fireplace and an oversized eat-in kitchen with solid wood cabinetry, pull-out storage, granite countertops, stainless steel appliances and a walk-in pantry. Designed for indoor-outdoor Florida living, sliding doors and a pass-through window connect the kitchen to the expansive covered lanai and large screened pool area, creating an ideal setting for relaxing, entertaining and enjoying the peaceful green views. The flexible floor plan also includes a family room, private office/study with exterior access and a downstairs bedroom suite with ensuite bath and private pool access, perfect for guests, extended family or multigenerational living. Upstairs, the refreshed living quarters provide room for everyone to spread out. The oversized primary suite extends from the front of the home to the back and features a walk-in closet, generous natural light and beautiful views of the golf course setting. The upstairs improvements continue with recently replaced custom bathroom vanities in all three upstairs bathrooms, new ceramic tile in both upstairs bathrooms, a new bathtub and a renovated upstairs shower completed in 2024. New windows were also installed in April 2026 in all upstairs bedrooms, along with two new downstairs front-facing windows. Additional highlights include a February 2025 water heater, pool cage installed in 2008 and rescreened in 2021 and a pool that was remarcited in 2017. Forest Lakes Country Club Estates is loved for its central Sarasota location, established neighborhood feel, larger lots and convenient access to some of the area’s best everyday amenities. From this location, you are close to shopping, dining, grocery stores, medical facilities, schools, parks, downtown Sarasota, Southside Village, Arlington Park, Gulf Gate, Siesta Key Beach and major roadways connecting you throughout Sarasota and Manatee counties. With its grand architecture, screened pool, updated roof, refreshed interior, golf course views, generous lot size and unbeatable central location, this classic Forest Lakes home offers space, character and the Sarasota lifestyle buyers are looking for. Schedule your private showing today!
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Ronald Pepka (941-877-1488)
62 SANDY HOOK RD S, SARASOTA, FL 34242
$2,995,000242 Days on yellowkey MLS ID: A4667491
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2658 Built: 1964Monthly Fee: $161 Tax: $8,811 (2024)Community: Sandy HookSingle Family
Taxes:$8,811
Remarks: In the coveted Sandy Hook Gulf Beach enclave of only 42 homes, this unique Mid-Century Modern home is now offered for purchase for the first time since 1983. The one-of-a-kind mid-century modern retreat rests on 1.6 acres of serene lakefront adjacent to where Big Sarasota Pass meets the Gulf of Mexico. Created by Frank Folsom Smith, a noted member of the Sarasota School of Architecture, this passively designed treasure was crafted from local cypress, oak, terra cotta and Ocala block and sits harmoniously within a lush Florida-native landscape alive with palms, cedars, and blooming wild flora. Nature lovers will delight in the lake along the southern edge of the property, home to a vibrant array of wildlife. The main residence, built in 1964 and lovingly preserved by its current owner since 1983, features timeless modernist design and abundant natural light through true north and south facing 10-foot glass sliders that welcome daylight. Meanwhile the interiors are shielded from direct sun for restful living. The guest house, added in 1987, also designed by the firm, complements the main home, together offering 5 bedrooms, 3 full bathrooms, 2 expansive great rooms, and a rare wood-burning fireplace, perfect for cozy winter evenings. Outdoors, all residents can enjoy their choice of sun-dappled terraces or shaded garden hideaways beneath more than 120 mature palms and cedars. Thoughtful upgrades ensure comfort and ease in this home's remodeled kitchen with all new appliances, new Trane HVAC systems covered by 10-year warranties, a 2025 deep-well irrigation system, and low-voltage outdoor lighting synchronized by the integrated atomic clock for effortless ambiance. Just a 150-meter stroll west through the trees leads you to Sandy Hook’s exclusive residents-only Gulf beach, a secluded paradise of sugarwhite quartz sand where sea turtles hatch annually and dolphins and manatees play offshore and sunsets paint the sky in vivid color. Conveniently located near Siesta Village’s boutiques and restaurants, and within easy reach of top-rated Sarasota County schools, The Out-of-Door Academy, and Sarasota Memorial Hospital, ranked among America’s top 50, this home offers the perfect blend of mid-century authenticity, privacy, and coastal lifestyle. This truly rare architectural offering is where Siesta Key’s natural beauty and Sarasota’s cultural soul meet the timeless artistry of mid-century design.
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE (941-921-1000)
Listing Agent: Fred Beles (941-921-1000)
6139 HOLLYWOOD BLVD, SARASOTA, FL 34231
$999,90023 Days on yellowkey MLS ID: TB8512156
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 1953 Tax: $9,362 (2025)Community: Pine Shores Estate 4Th SecSpa: YesSingle Family
Taxes:$9,362
Remarks: Offered below appraised value at $999,900, this truly one-of-a-kind Sarasota property presents a rare opportunity to own a private family compound just minutes from Siesta Key and located West of the Trail in the highly desirable Pine Shores neighborhood. Set on an oversized 0.34-acre gated, fenced, and walled homesite, this exceptional property offers two separate living residences, incredible flexibility, and resort-style outdoor living — all with NO HOA and NOT located in a flood zone. This property also represents an outstanding investment opportunity with a proven rental history and strong income-producing potential, making it ideal for seasonal rentals, multigenerational living, guest accommodations, or long-term investment strategies. The beautifully maintained main residence features 3 bedrooms and 3 baths with approximately 1,685 square feet of living space and is being offered fully turnkey furnished. ROOF (3 - 4 years old), HVAC 2025, TANKLESS WATER HEATER 2025. Pride of ownership is evident from the moment you arrive, with a long paver driveway leading to a charming, gated breezeway entrance and lush, low-maintenance tropical landscaping. The main home showcases polished terrazzo flooring, crown molding, remodeled kitchen and baths, granite countertops, impact-resistant windows and doors, and a state-of-the-art water filtration system. Outdoor living is exceptional with a heated saltwater pool, spa, summer kitchen, and expansive entertaining areas designed for the ultimate Florida lifestyle. Built in 2013, the detached oversized two-car garage structure adds tremendous value and versatility. Upstairs, guests or extended family will enjoy a spacious studio apartment complete with a full kitchen, breakfast bar, custom cabinetry, hardwood flooring, upgraded lighting and fans, built-in hideaway bed, full bath, and private laundry area. The garage also includes built-in storage shelving and an additional side carport. The oversized paver driveway and side access provide abundant room for boat, RV, or recreational vehicle parking. The expansive lot also offers future flexibility with room to potentially expand, add additional structures, or create a custom luxury estate environment. Located just minutes from Siesta Key Beach, Phillippi Estate Park, shopping, dining, and Sarasota’s vibrant cultural attractions, this is a truly special property combining location, privacy, flexibility, lifestyle, and investment value in one extraordinary offering.
Listing is courtesy of: MARZUCCO REAL ESTATE (239-776-5194)
Listing Agent: Lisa Kohan (239-272-5901)
1516 S ORANGE AVE, SARASOTA, FL 34239
$4,560,000168 Days on yellowkey MLS ID: A4676686
REDUCED by $15,000 (0.3%) on 06/10/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4224 Built: 2026 Tax: $13,597 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$13,597
Remarks: The highly-acclaimed team of professionals at Allegra Homes has yet again created a vision of luxury, elegance and simplistic functionality. A dynamic 4,224 sq. ft. open layout is rich in gorgeous details everywhere you turn. Feast your eyes on the “St. Michael,” a two-story beauty with stunning curb appeal and exciting interiors thoughtfully designed for grand-scale living. In addition to 4 bedrooms, there’s also a separate 254 sq. ft. casita ideally suited for in-laws or guests wanting to enjoy the fantastic Florida ambiance just a little longer. The extended foyer and great room feature an amazing 21-ft ceiling and invite you into a fascinating space with see-thru views out to the magnificent outdoors. Step into the heart of the home, where the great room exudes warmth and sophistication. A wood-beamed ceiling adds character and warmth, while clerestory windows flood the space with natural light, creating an inviting and airy ambiance. Triple sliders seamlessly connect the indoors to the covered poolside lanai. In the family room, a stunning stone-faced center wall serves as the focal point, flanked by built-in shelving with elegant lighting. The consummate chef will delight in the variety of accoutrements offered in this delectable space honed to perfection. A large stone-topped island easily seats 5 and the premium appliance package encompasses a 36” Wolf gas induction cooktop, a 42” Sub-Zero fridge, a Wolf oven with matching drop-down microwave, an ASKO dishwasher, a Sub-Zero wine cooler, and adequate counter and storage space including a pantry. Adding stylish flair to the dining room is a built-in buffet with full mirrored wall and wide windows overlooking the tropical pool setting. A separate dry bar with pass-thru is convenient to both the great room and kitchen for ease of serving family and friends. Overlooking the pool is a bonus room with a pool bath and wall of pocketing sliders opening wide to a covered 545 sq. ft. outdoor oasis with tongue-and-groove ceiling, nicely equipped summer kitchen, and abundant room for both dining and lounging. The pavered lanai is enclosed with ClearView screening and includes a 25’x19’ heated pool with 6 stepping pads, spill over spa, sun shelf, LED bubbler, salt conversion generator and Pebble Tec finish. The owner’s wing, with an adjacent study, may become your most prized room of the home with its drop tray ceiling, spacious seating area, soaking tub inside an exquisite large glass shower, separate dual vanities and water closet. An additional bonus room with wet bar, two bedrooms and a bath are located upstairs. Other honorable mentions include a 3-car garage with epoxy floor, tankless gas water heater, 10-ft ceilings, modern staircase with floating steps, recessed lighting, crown molding, brick paver drive and walkway, 8’ interior solid core doors, professionally landscaped, and irrigation system. Poised on over a 1/3 acre lot in prestigious Harbor Acres with a sought-after central location near the arts, entertainment, dining, shopping, beaches, boating, golf and other year-round adventures. For families with elementary school-age children, top-ranked Southside School celebrates 120 years of excellence in academic achievement. This stately new residence has been masterfully crafted inside and out, and will add a sense of pride and joy to an already perfect lifestyle.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1521 S LAKE SHORE DR, SARASOTA, FL 34231
$5,980,000502 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
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)
3443 CLARK RD #242, SARASOTA, FL 34231
$169,00070 Days on yellowkey MLS ID: A4688551
0 Days Off yellowkey (back on 6/18/2026)
REDUCED by $4,000 (2.3%) on 06/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 555 Built: 1974 Tax: $1,883 (2025)Community: SiennaCondo
Taxes:$1,883
Remarks: Under contract-accepting backup offers. Great investment opportunity! This 1 bedroom 1 bathroom 2nd floor unit comes Turn Key furnished! Long term rental has the potential net ROI over 6%. The low $365 monthly fee includes: water, sewer, trash collection, building insurance and outside maintenance including the roof and grounds. Upgrades includes: open and updated kitchen and bathroom, no carpet. Enjoy access to amenities such as swimming pool, fenced doggie park, BBQ grill and fitness center. Minutes from the famous Siesta Beach, shopping, dining, entertainment and the highway.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Julianna Kovacs (941-518-6485)
1959 WISTERIA ST, SARASOTA, FL 34239
$3,150,000119 Days on yellowkey MLS ID: A4683340
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2844 Built: 2026 Tax: $10,143 (2025)Community: Desota ParkSpa: YesSingle Family
Taxes:$10,143
Remarks: Welcome to 1959 Wisteria Street – a beautiful New Construction Single Story home, West of the Trail, that your clients will love! This just-completed modern coastal single story home is located West of the Trail in preferred Flood Zone X, offering elevated storm protection and convenient access to Southside Village, Downtown Sarasota and Siesta Key beaches. Designed and built with Majestik Homes' signature strength and style, this 3 bedroom plus office, 4 bath home blends architectural elegance with energy efficiency and storm-ready construction. You will be awestruck as you open the home’s large glass-paneled double doors and step into a spacious foyer that flows seamlessly into an expansive great room filled with natural light and a striking entertainment wall — perfect for relaxed living and stylish entertaining. Panoramic sliding glass doors open to a private backyard oasis featuring a sparkling pool and spa, and a fully appointed outdoor BBQ area designed for effortless Florida entertaining. The chef’s kitchen features high-end gas appliances, and the dining room is ideal for intimate dinners and larger gatherings alike. The Primary Suite is spacious and luxurious with its own private lanai. The spa-inspired primary bath offers both an indoor shower and a private outdoor shower for a true resort-style experience. Bedroom 3 includes an en-suite bath. Situated on a generous homesite with large side yards and enhanced privacy, the property is complemented by a circular driveway and an oversized 3-car garage — providing ample space for guests, storage, and everyday functionality. Beautifully staged and thoughtfully designed, this home showcases artwork from some of the local area’s most inspiring artists. Easy to show — you won’t want to miss this exceptional opportunity.
Listing is courtesy of: MAJESTIK REALTY, INC (941-363-6080)
Listing Agent: Michael Hankin (941-504-4337)
611 TREMONT ST, SARASOTA, FL 34242
$3,399,000155 Days on yellowkey MLS ID: A4678455
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4194 Built: 2005 Tax: $21,457 (2025)Community: Siestas BaysideSpa: YesSingle Family
Taxes:$21,457
Remarks: A spectacular offering on one of Siesta Key’s most coveted streets, this stunning canal-front residence on Tremont Street represents a truly special opportunity to own a home that seamlessly blends boating, timeless island charm, and refined coastal living. Tucked beneath mature trees in a quiet, established enclave known for its old Siesta character, the property offers private canal frontage with a lift and a short, easy boat ride to the Intracoastal Waterway, all just minutes from Siesta Village and the world-renowned white sands of Siesta Beach. Homes of this caliber and setting are seldom available and must be experienced in person to be fully appreciated. Offering 4,194 square feet under air, the thoughtfully designed floor plan is both impressive and highly livable, ideal for full time residents and seasonal owners alike. Soaring ceilings, abundant natural light, and quality craftsmanship define the interior. The main floor primary suite is complemented by additional bedrooms on the main level, providing the ease of one level living, while the second floor offers a spacious guest suite and bonus room with peaceful views of the pool and canal. Exceptional indoor-outdoor living is at the heart of the home. Multiple pocketing sliding glass doors open wide to an expansive covered and fully screened lanai, creating a seamless connection between interior and exterior spaces. The outdoor living area is generous in scale and designed for entertaining, featuring a heated pool and spa, summer kitchen, gas fireplace, and multiple areas for dining and relaxation. The large screened layout allows you to comfortably enjoy outdoor living year round, regardless of the weather. Lush tropical landscaping enhances privacy and creates a tranquil island setting, while boating enthusiasts will appreciate the private lift and convenient access to open water. Impact-rated windows and doors, a generator, and a three-car garage provide peace of mind and everyday practicality. 611 Tremont Street combines location, boating, and lifestyle in a way few homes can. If you have been waiting for an exceptional Siesta Key property in one of the island’s most desirable neighborhoods, this is one you should see in person before it sells.
Listing Agent: Mike Warm, Llc (941-525-2740)
850 S TAMIAMI TRL #801, SARASOTA, FL 34236
$325,00015 Days on yellowkey MLS ID: TB8515223
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 980 Built: 1998 Tax: $4,584 (2025)Community: Central Park Sec 2 Ph 1Condo
Taxes:$4,584
Remarks: Seller is Agent/Broker
Listing is courtesy of: BAILEY AND ASSOCIATE (951-741-5626)
Listing Agent: Katherine Bailey (951-741-5626)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000290 Days on yellowkey MLS ID: A4663880
1 Days Off yellowkey (back on 5/26/2026)
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. 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. 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)
3165 REGATTA CIR, SARASOTA, FL 34231
$459,000112 Days on yellowkey MLS ID: A4683961
REDUCED by $5,900 (1.3%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Remarks: Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Turnkey furnishing option is also available which could make for an easy second home. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
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