Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
1647 SIESTA DR, SARASOTA, FL 34239
$1,650,00022 Days on yellowkey MLS ID: A4695812
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3032 Built: 2025 Tax: $17,778 (2025)Community: BayviewSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,778
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings, natural light, and high-quality finishes throughout. The home features a modern and elegant kitchen with top-of-the-line Cafe' appliances, quartz countertops, and custom cabinetry. The primary bedroom located on the upper level can be accessed by elevator is a true sanctuary, offering a plush and peaceful retreat. It boasts vaulted ceilings, en-suite bathroom that includes a soaking tub and a separate shower that's great for unwinding after a long day. The room also features a generously sized walk-in closet with abundant space for storage and organization as well as a private terrace. On the second floor you will find three vast bedrooms, with plenty of closet space for added convenience and comfort. One of the most notable features of the second floor is the sizable sundeck and balcony, which are attached to both bedrooms. The laundry room is conveniently located on the second floor as well. The spacious bonus room offers endless possibilities, from an office, den, playroom, media center or a home gym. This home has two patios with an outdoor area with a large pool and hot tub that seamlessly blend the indoor and outdoor living with meticulously planned landscaping. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping in the area. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
1794 CUNLIFF LN, SARASOTA, FL 34239
$2,997,000108 Days on yellowkey MLS ID: A4685523
REDUCED by $98,000 (3.2%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3377 Built: 2015 Tax: $39,491 (2025)Community: Bay View Heights AddSpa: YesSingle Family
Taxes:$39,491
Remarks: Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed in natural light. Oversized 10-foot doors frame every room, while hurricane-impact sliding glass doors seamlessly connect the interior to a resort-style outdoor oasis. The expansive pool deck showcases a stunning lighted fountain spilling from the spa into the oversized pool, a rainfall pergola, and lush tropical landscaping surrounded by a six-foot privacy fence—creating the ultimate setting for both relaxation and entertaining. Built with the signature craftsmanship of Allegra Homes, the residence features exceptional custom millwork, striking feature walls, designer lighting, and distinctive ceiling details throughout. Spanning 3,582 square feet, this thoughtfully designed home offers four spacious bedrooms, three luxurious bathrooms, a private den/office with a turret ceiling, and a versatile bonus room. The gourmet kitchen—one of Allegra’s most beloved layouts—is a true culinary showpiece, appointed with Sub-Zero and Wolf professional-series stainless steel appliances, including a five-burner natural gas cooktop, a second Sub-Zero beverage refrigerator, custom luxury cabinetry, rich 3cm granite countertops, and a glass tile backsplash with hidden electrical outlets Adjacent to the kitchen, the elegant dining room features a dramatic aquarium glass window overlooking the pool and gardens, along with a built-in buffet accented by a mirrored feature wall. The home’s split floor plan provides exceptional privacy. The serene primary suite is a private retreat, offering a spa-inspired bath with a walk-through shower, dual vanities, and a private water closet. A custom walk-in closet features built-in shelving, drawers, and a hallway dressing mirror. The bedroom is highlighted by an intricate custom ceiling design, designer lighting, and private access to the pool deck. On the opposite side of the first floor, you’ll find a built-in desk alcove, a spacious laundry room, a secondary bedroom with a walk-in closet, a full hall bath, and the bonus room with disappearing sliding glass doors that open to the screened pool area. The first level features rich porcelain wood-style flooring, while the second level is comfortably carpeted and hosts the third and fourth bedrooms, along with a media closet and additional HVAC storage. Bahama shutters and custom blinds complete the bedrooms and bathrooms. Situated on a 0.28-acre elevated lot, built above the flood plain in 2015, this exceptional residence offers privacy, luxury, and an unbeatable central location. Just minutes away are Sarasota Memorial Hospital, Southside Village, and top-rated Southside Elementary, with Siesta Key Beach, downtown Sarasota, Westfield Siesta Key Mall, and St. Armands Circle only a short drive away. This remarkable property may be purchased turnkey furnished, including original artwork, bronze sculptures, designer furnishings, and custom rugs, available under a separate bill of sale. Schedule your private showing today. Proof of funds required with all offers.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Jill Berg (941-315-1199)
2915 WEBBER ST, SARASOTA, FL 34239
$399,90013 Days on yellowkey MLS ID: A4696773
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1290 Built: 1958 Tax: $2,275 (2025)Community: South GateSingle Family
Taxes:$2,275
Remarks: "This beautiful property has granite countertops, shaker cabinets, a newer kitchen and bedroom that was totally remodeled about 6 years ago. It features brand new flooring, a newer air conditioning system (approximately seven years old), attractive brick pavers, a patio, and a large fenced yard."
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Curtis Putrino (941-302-8776)
465 E ROYAL FLAMINGO DR, SARASOTA, FL 34236
$4,850,0008 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
Taxes:$39,161
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)
1516 FOX CREEK DR, SARASOTA, FL 34240
$1,799,500106 Days on yellowkey MLS ID: A4683593
REDUCED by $100,000 (5.3%) on 06/23/2026
Bed: 6 Bath: 5.5 Gar: 8 Liv Area Sq Ft: 4277 Built: 1973 Tax: $14,746 (2025)Community: Fox Creek AcresSingle Family
Taxes:$14,746
Remarks: One or more photo(s) has been virtually staged. “NEW PRICE IMPROVEMENT! A Rare Opportunity with unmatched value to Own Three Distinct Residences in One Exceptional Property.” MULTI-GENERATIONAL HOUSING OR INCOME PRODUCING OPPORTUNITY! Two separate 3BR/2BA Homes + an additional 2BR/2BA Apartment. Each of the homes enjoys its own private entrance, separate driveway and its own garage, allowing households zzzs to live side by side while maintaining independence. And that's not all....the Workshop features a Full Bath and Laundry Room. In addition, there is another Barn which could accommodate 4+ Cars. This is truly a Quintessential Multi-Generational Compound on five-plus acres in Sarasota county, located adjacent to Waterside at Lakewood Ranch! Whether accommodating extended family, long-term guests or providing a private residence for caregivers, the thoughtful layout offers exceptional versatility. At the heart of the property, a beautiful pool and expansive screened lanai create an inviting backdrop for a Florida indoor/outdoor lifestyle. This outdoor retreat is positioned so both residences could enjoy easy access, making it a natural gathering place for family and guests alike. A dedicated pool bath adds convenience for swimmers and guests, keeping the indoor living areas pristine while enhancing seamless flow between indoor comfort and outdoor enjoyment. Expanding the living possibilities, perhaps you might want to consider using part or all of this property as Airbnb. The second-level apartment offers privacy with a light and airy vibe featuring an open plan and full kitchen. The unique adjoining sunroom spanning the length of the unit would be ideal for a yoga studio, game room or added entertainment space. Unlock the potential of this versatile apartment as a guest retreat, income-producing rental, inspiring studio or private office suite. This five-plus acre homesite with NO HOA, NO CDD's, and NO DEED RESTRICTIONS gives you the freedom to tailor the property to your personality. The large detached pole barn adds tremendous utility, providing ample space for farm animals, boats, RVs, equipment, hobbies or workshop use, ideal for those who need room to store, build or play. Buy with confidence knowing this home has a whole house generator, updated plumbing with no cast iron or copper piping. The cast iron sewer pipes have been replaced with PVC and the copper potable water pipes have been replaced with CPVC. The 4Point Inspection and Wind Mit has been completed. Homeowner's Insurance only $6700 per year! Experience the balance of peaceful country living with an unbeatable location. Within minutes of restaurants, boutiques, farmers markets, parks, and year-round events at the vibrant waterfront district at Waterside Place in Lakewood Ranch and only a short drive to the stunning beaches and renowned dining and cultural attractions of dynamic Sarasota. The home is positioned in one of the areas most dynamic growth corridors, just minutes to the newest Lakewood Ranch developments along Fruitville Rd corridor ~ where premier shopping, exceptional dining and modern conveniences continue to flourish! Whether you envision a private family compound, a multi-generational retreat, an income-producing opportunity or a flexible live-work estate, this remarkable property offers the rare combination of space, freedom and location. Schedule your private showing today and experience the endless possibilities for yourself. Welcome home to 1516 Fox Creek Dr!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Trish Chandler (941-306-9533)
3443 CLARK RD #242, SARASOTA, FL 34231
$169,00076 Days on yellowkey MLS ID: A4688551
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
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: 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)
1654 STICKNEY POINT RD #54-201, SARASOTA, FL 34231
$299,00058 Days on yellowkey MLS ID: A4691665
3 Days Off yellowkey (back on 6/23/2026)
REDUCED by $11,000 (3.5%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1016 Built: 1975 Tax: $3,415 (2025)Community: Castel Del MareSpa: NoCondo
Taxes:$3,415
Remarks: Bayfront community one block to the south bridge to Siesta Key • Turnkey furnished • 3D walkthrough available Second-floor 2-bedroom, 2-bath condo in Castel Del Mare, a waterfront community on Little Sarasota Bay at the gateway to Siesta Key. Just minutes to Siesta Key Beach at a fraction of island pricing. This 1,016 sq ft turnkey furnished residence features a partially updated kitchen, living/dining combo with ceiling fans, walk-in closet, and a screened lanai with west-facing exposure. Assigned parking included. Settle into the bayside heated pool and watch boats cruise the Intracoastal Waterway, or launch a kayak from the community dock. Castel Del Mare offers two heated pools, tennis and pickleball courts, shuffleboard, fitness center, clubhouse, bayside fishing gazebo, kayak storage with launch access, and a scenic boardwalk along Little Sarasota Bay. Rental minimum 30 days, 3 rentals per year. Near public transit with easy access to Siesta Key Beach, Siesta Village dining, and the Stickney Point Bridge. Nearby dining includes Merci Café and La Dolce Vita. Publix and Detwiler's Farm Market within 1 mile. Red Bug Slough Preserve and Gulf Gate Village nearby. Includes 3D tour for virtual viewing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
2100 MCCLELLAN PKWY, SARASOTA, FL 34239
$6,000,0008 Days on yellowkey MLS ID: A4693318
Bed: 5 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 4765 Built: 2026 Tax: $14,834 (2025)Community: Mcclellan Park ResubSpa: YesSingle Family
Taxes:$14,834
Remarks: Pre-Construction. To be built. Construction in progress, and opportunity for customizations. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. This home is 4,765 square feet, with 5 bedrooms, 7 baths and 2 half baths. Inside, you'll discover an open floor plan that harmoniously blends expansive spaces with comfortable, luxurious living. The soaring, 18-foot vaulted ceilings and seamless transitions between the grand indoor living areas, multiple patios, wrap-around balconies, and lush outdoor grounds make this home ideal for intimate gatherings and larger events alike. The well-appointed kitchen features an open-concept layout, highlighted by a stunning quartz island with waterfall edges, under elegant pendant lighting. Custom cabinetry in a sleek, glossy finish complements the state-of-the-art stainless-steel appliances, which include a professional-grade gas range, double ovens, and a built-in espresso machine. A discreet entry leads to a spacious butler’s pantry, offering additional storage, a secondary sink, and a prep area - perfect for hosting large gatherings or keeping the main kitchen organized. The pantry also mirrors the kitchen’s custom cabinetry and countertops for a seamless design. Adjacent to the dining area, a glass-enclosed, temperature-controlled wine room adds both style and function, and is sure to beautifully showcase your wine collection with custom shelving and ambient lighting. The expansive primary bedroom features 14-foot vaulted ceilings and large windows that fill the room with natural light. Soft, neutral tones create a serene environment, while the en-suite bathroom offers a spa-like retreat with a freestanding soaking tub positioned beneath a large window. Dual sinks with quartz countertops and sleek fixtures provide ample space, and the frameless glass walk-in shower features multiple shower heads and exquisite tile work. For entertainment, the theater room is a dream come true, offering tiered seating with oversized leather recliners - each equipped with cup holders and personal charging stations. The ultra-high-definition projection screen spans an entire wall, ensuring an immersive viewing experience. Outside, the resort-style pool is the centerpiece of the backyard, complete with a built-in spa, waterfall, and ambient lighting. A natural stone deck, covered lanai dining area, and a fully equipped outdoor kitchen and bar provide the perfect setting for outdoor living. A cozy fire pit with seating offers a perfect gathering spot for evenings, while the lush landscaping - featuring vibrant flower beds, mature trees, and decorative water features - creates a tranquil and picturesque setting. This outdoor space seamlessly combines comfort, style, and functionality for an exceptional living experience. Positioned on a grand parcel of approximately 20,505 square feet, this home offers privacy and tranquility amidst beautifully landscaped grounds. Whether you’re seeking the excitement of downtown Sarasota or the natural beauty of the Gulf, experience the perfect blend of luxury, comfort, and convenience in this exceptional home in a fabulous location.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,00069 Days on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Elementary School: Phillippi Shores Elementary
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Drew Jacobsen (941-253-6309)
5966 MIDNIGHT PASS RD #G-67, SARASOTA, FL 34242
$2,299,00048 Days on yellowkey MLS ID: A4692674
REDUCED by $90,000 (3.8%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1396 Built: 1970 Tax: $10,966 (2025)Community: Palm Bay Club ISpa: YesCondo
Taxes:$10,966
Remarks: Own a piece of paradise at the Palm Bay Club tower, where Siesta Key sunsets and Gulf views become a part of daily life. Positioned in the waterfront tower, this airy corner residence captures a rare perspective down Siesta Key’s shoreline, where wide Gulf views, turquoise water, and the movement of the surf are visible from every room. Its unique southern orientation is one of the reasons the current owner fell in love with the property. It offers the beauty of a true Gulf-front setting without the harsh afternoon sun that many beachfront residences contend with. It is low enough to remain connected to the beach and water below, yet elevated enough to frame a panorama of the coastline. The experience from within the residence is both soothing and unforgettable. Floor-to-ceiling windows fill the unit with natural light throughout the day. Morning sunrises arrive softly through the eastern-facing windows, while the southern exposure continuously reflects the changing colors of the Gulf, beach, and sky across the living spaces. Lovingly maintained as a private coastal retreat for the owner, the residence has been thoughtfully and continually improved with an emphasis on luxurious comfort, quality, and ease of ownership. Features include custom cabinetry and generous storage, KitchenAid and Kohler appliances, Brizo fixtures, designer lighting and furnishings, top-of-the-line custom Hunter Douglas blackout blinds, hurricane-rated window protection, a private in-unit washer and dryer — a rare convenience within the building, and much more. The interiors feel refined yet relaxed, designed for extended stays, entertaining guests, or simply enjoying quiet mornings overlooking the water. While this residence has primarily been enjoyed privately, Palm Bay Club’s highly regarded in-house rental program and flexible three-day minimum rental policy provides an exceptional option for owners seeking to generate income alongside personal enjoyment. The property includes 24-hour onsite security as well as full-time management, front desk and maintenance personel 7 days/week. Many long-term staff members contribute to the welcoming and established feel that owners value so highly. The Palm Bay Club's beach resort lifestyle comes with a level of service and atmosphere that sets it apart on Siesta Key. Available beach staff will take the complimentary loungers anywhere on the private beach by ATV. Owners and guests enjoy one of the largest expanses of direct access private beach frontages on the Key, with an outdoor grill, covered pavilions, a rinse station, and additional premium beach cabana services. The Gulf side amenities also include poolside bathrooms and showers, and a fitness center that looks out to the big heated pool and tennis/pickleball courts. A brand new shuffeboard court has been added in 2026. For a different laidback vibe, residents and guests simply walk to the Bay side to lounge by the heated pool and hot tub, where they can watch the boats go by amidst the boat docks, fishing pier, and palm trees. Must see to appreciate this rare tower unit with one of the most desirable and requested orientations at this exceptionally well maintained gulf-to-bay resort condo complex. This fully furnished turnkey property is move-in ready for immediate enjoyment or future rental use.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
6338 BEECHWOOD AVE, SARASOTA, FL 34231
$500,000105 Days on yellowkey MLS ID: A4685783
REDUCED by $25,000 (4.8%) on 06/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1506 Built: 1954 Tax: $1,942 (2025)Community: Emerald HarborSingle Family
Taxes:$1,942
Remarks: Located less than a mile from the world-famous Siesta Key Beach, this charming 3-bedroom, 2-bathroom home offers the perfect blend of coastal living and everyday convenience. Situated on a spacious lot, the property features a large backyard—ideal for outdoor entertaining, gardening, or simply enjoying Florida’s beautiful weather. A separate shed in the backyard provides additional storage or workspace. Hurricane windows throughout the house as well as an updated AC. Enjoy being just minutes from shopping, restaurants, and entertainment, while still tucked away in a quiet residential setting. Take a relaxing walk or short bike ride to the beach and experience the stunning white quartz sand and breathtaking sunsets that make Siesta Key so special. Whether you’re looking for a primary residence, vacation getaway, or investment opportunity, this home offers endless potential in one of Sarasota’s most desirable locations.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
5103 WINDWARD AVE, SARASOTA, FL 34242
$3,539,000173 Days on yellowkey MLS ID: A4676707
REDUCED by $10,000 (0.3%) on 06/10/2026
Bed: 3 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3034 Built: 2026 Tax: $4,091 (2024)Community: Sara SandsSpa: YesSingle Family
Taxes:$4,091
Tax Year: 2024
Remarks: Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand beaches and charming Siesta Village easy and convenient. The free-flowing plan, offering 3,034 sq. ft. of open living, will seduce you with its inviting atmosphere wrapped in casual elegance and modern sophistication. With plenty of natural light, the great room boasts double-height ceilings adorned with rich architectural detail, an elaborate floor-to-ceiling fireplace wall, and see-through views to the expansive outdoor space and coveted canal setting. Beyond the great room’s glass doors, an entertaining lounge with wood ceiling accents, a professional grill station, and a heated pool/spa await your plans for spending cherished time with family and friends. As evening approaches, night lighting transforms the beautiful backyard and creates a timeless ambiance that encourages relaxation and reflection. A gorgeous kitchen is enhanced with an abundance of amenities including a premium Sub-Zero and Wolf appliance package, stone counters, stylized fixtures and finishes, a walk-in pantry, and adjoining laundry. The formal dining room features a built-in buffet and French doors leading to a brick paver patio, making it a wonderful spot for dining alfresco under the stars. The bonus room, with wet bar and pool bath, features two walls of glass sliders showcasing the extensive outdoors and picturesque water views. The primary suite is an oasis of serenity with an office outfitted with built-ins, a generous wardrobe for two, and an exquisite bath intended to pamper and spoil with a free-standing tub, a frameless glass shower with rain head, separate vanities with stone tops, and a water closet. Two additional en-suites offer plenty of room to unwind and rejuvenate in comfortable privacy. A brick paver drive, a 3-car garage, professional landscaping with timed irrigation, eye-catching curb appeal, and other notable customizations inside and out, complete this magnificent waterfront home. This fresh new residence, designed by the award-winning team at Allegra Homes, has been artfully designed and crafted to offer the highest quality to those who live here. An exciting opportunity to make this island paradise yours!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1404 KENILWORTH ST, SARASOTA, FL 34231
$5,200,000161 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!
1519 HARBOR DR, SARASOTA, FL 34239
$4,595,0003 Days on yellowkey MLS ID: A4695101
0 Days Off yellowkey (back on 6/22/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3970 Built: 2026 Tax: $4,181 (2025)Community: Harbor Acres Sec 2Spa: YesSingle Family
Taxes:$4,181
Remarks: Under Construction. A dynamic 3,970 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. 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 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 Clear View 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 1/3-acre lot, and irrigation system. 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.
2171 ORCHID ST, SARASOTA, FL 34239
$370,000233 Days on yellowkey MLS ID: A4670904
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1471 Built: 1952 Tax: $4,111 (2024)Community: Washington Heights/ SouthgateSingle Family
Taxes:$4,111
Remarks: FIXER UPPER WITH LOCATION, LOCATION, LOCATION, SOUTHGATE Location - 1 block North of Siesta Drive on East side of Trail. This rare dead end street has a walking trail and is very private. Area is undergoing redevelopment with many homes in area being totally renovated or torn down and new homes being built. Walk to shopping center, restaurants & Brookside school and so much more. Sought after Southside Elementary is 5 minutes away. You can be at world famous Siesta Key beach in about 10 minutes. The home has 3 bedrooms, 2 baths, a nice back yard with stately trees. Bring your creativity, vision and love of the area or bring your building plans and have the home of your dreams in the neighborhood you love. This is either a redo or rebuild.
Listing Agent: Kris Niehaus (941-376-4950)
4708 OCEAN BLVD #E4, SARASOTA, FL 34242
$2,199,00073 Days on yellowkey MLS ID: A4689440
REDUCED by $91,000 (4.0%) on 05/21/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,662 (2025)Community: Windward PassageCondo
Taxes:$16,662
Remarks: Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (608-345-7089)
6415 MIDNIGHT PASS RD #211, SARASOTA, FL 34242
$799,900189 Days on yellowkey MLS ID: A4675481
REDUCED by $50,000 (5.9%) on 06/13/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2358 Built: 1975 Tax: $7,544 (2025)Community: AnchorageSpa: NoCondo
Taxes:$7,544
Remarks: Huge opportunity to own a spacious 2,400 sq ft, 3 bedroom condo on Siesta Key with an aggressive, new price drop! Now being offered at $799,900 - an unbelievable $339.22 per square foot (vs recent SK sales average of $460 per square foot). This is a fabulous family investment with plenty of room to sleep 8 people (Note: a 4th bedroom could easily be added). This condo has brand new floor-to-ceiling high impact hurricane sliders that run the entire length of the condo and open to a full 95’ lanai for a nice open-air feeling. Allow your family to enjoy your new vacation home, then use the successful in-house rental program to make additional income for yourself. The best of both worlds! Gated-community amenities abound here: both private beach access and intracoastal access with use of free boat slips and kayak racks. One of the largest heated pools on the Key. Brand new pickleball and tennis courts. Tropical landscaping that includes areas for nice seating on the intracoastal, outdoor grilling and picnics, shuffleboard, cornhole, and basketball goal. Fitness center and party/event space. Wheel-chair accessible property. You can go from car to kitchen with no steps! This condo offers a very desirable split floorplan with the primary bedroom on one end and the other two bedrooms on the opposite end with 2 distinct heating/cooling systems. Also includes 2.5 baths with both a tub and shower option. Generous closets in each room, plus a large owner’s closet, beach closet and unique private, full storage closet in hallway next to condo. Whether you are searching for a spacious family getaway, a peaceful primary residence, and/or a high-performing rental, this rare offering delivers.
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000205 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
1240 DOLPHIN BAY WAY #401, SARASOTA, FL 34242
$1,199,000269 Days on yellowkey MLS ID: A4658380
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1998 Tax: $12,546 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,546
Remarks: Huge Price Reduction!!! Fourth-floor end unit offering breathtaking views of the intracoastal waterway, featuring three spacious bedrooms and three full ensuite baths. Newly installed luxury vinyl plank flooring graces the entire unit. The expansive glassed lanai boasts recently replaced sliding doors, complete with accordion shutters on the inner doors and impact-resistant glass on the outer ones. The kitchen has been thoughtfully opened up and reconfigured for optimal enjoyment. The living and dining areas are bright and roomy. Dolphin Bay is a sought-after, gated, pet-friendly community with only 50 units, each having its own private underbuilding garage, and well-known for its vibrant atmosphere. Amenities include three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier, and kayak access. The complex is well-maintained, with a freshly updated exterior and new elevators in 2024, set amidst beautifully landscaped grounds. Just a short stroll to the world-renowned, white crystal sands of Siesta Key beach. Condo fees at Dolphin Bay are being lowered in 2026.
Listing Agent: Ethel Lovelace (941-586-7390)
1269 DOCKSIDE PL #115, SARASOTA, FL 34242
$825,000269 Days on yellowkey MLS ID: A4656792
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $6,667 (2024)Community: Harbour TowneSpa: YesCondo
Taxes:$6,667
Remarks: This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the slip (#38). Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo features tile flooring throughout with both HVAC and appliances that are only a couple of years old. The roof was replaced in November 2021, and the unit has a one-car garage with storage above as well as a dedicated parking space in front. In addition, this unit has one of the few private outdoor decks in the community. Harbour Towne offers fantastic amenities, including a clubhouse, heated pool, spa, and tennis/pickleball courts. Enjoy the village by day or evening for great dining, shopping and live music. A complimentary trolley runs by the complex on a regular schedule in season. This is a great place to live and play! Look no further, this is where your fun-filled life begins.
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