Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000124 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.7%) on 06/11/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$25,684
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000125 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Tax Year: 2025
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
1541 FLOWER DR, SARASOTA, FL 34239
$1,870,000398 Days on yellowkey MLS ID: A4656365
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3302 Built: 1956 Tax: $7,456 (2024)Community: Harbor AcresSpa: NoSingle Family
Taxes:$7,456
Elementary School: Southside Elementary
Remarks: This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel was built in 1956 and was originally a 2/2. The original bathrooms are still in their original state and are in good condition providing a cool retro vibe. The original hardwood floors and fireplace exude warmth and sophisticated charm. The current owner purchased the home in 1989 and remodeled the kitchen and added a new wing on the house with 2 additional large bedrooms ensuite with baths. Copious amounts of storage in all 4 bedrooms and a huge laundry room with lots of closet space as well. The garage is oversize and there is a picturesque circular driveway for ample parking. There is plenty of room to put in a pool of your own design. The house was re-roofed in 2018. Some of the most beautiful homes in Sarasota are your neighbors in Harbor Acres. And Flower Drive is a special address with the highly sought after Southside Elementary School just 1-mile away, you can’t beat this property. In real estate it is all about Location, Location, Location. This home has plenty of room for the family, so, come on home!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kathleen Griffin (941-302-3979)
1669 35TH ST, SARASOTA, FL 34234
$399,90051 Days on yellowkey MLS ID: A4696081
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1782 Built: 1963 Tax: $2,470 (2025)Community: Amaryllis ParkSpa: NoSingle Family
Taxes:$2,470
Elementary School: Emma E. Booker Elementary
High School: Booker High
Remarks: Welcome to the House of Light...Lots of Windows lets the Sunshine flow throughout this Home, setting a Lovely, Peaceful Feeling and Calming Atmosphere. With a Private Front Entry, This Spacious Home has 3, possibly 4 Bedrooms, as, the Front Room has a Closet Area and maybe partitioned off into a 4th Bedroom as needed. With a Spacious Family Room with a coat closet for extra storage, this room could also be used as a Huge Dining Room. There is also an Office Area with a private side door entrance on the side of the house. Nicely Remodeled Kitchen with Stainless Steel Appliances, Granite Counters and has an Eat-In Area. Spacious Master Suite has an En Suite and both, a Spacious Walk-in Closet and a Built-In Closet for Plenty of Storage. 2 Guest Bedrooms are Spacious and a Lovely Remodeled Guest Bathroom. Hallway has a Storage Closet and a Linen Closet. There is a Carport with a Side Door Entry and a Utility-Laundry Room and a Spacious 8x10 Storage Shed in the Back Yard. This is Truly a Wonderful Family Home with a Newer Roof 4yrs, Hurricane Impact Windows 2yrs, Air Conditioner 2yrs, New Electric Water Heater. This Family Home is a True Joy to Live in....Welcome Home...
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Elaine Graczyk (941-320-9910)
1624 STICKNEY POINT RD #1624-208, SARASOTA, FL 34231
$339,00082 Days on yellowkey MLS ID: OM723810
REDUCED by $9,500 (2.7%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1016 Built: 1975 Tax: $3,939 (2025)Community: Castel Del MareSpa: NoCondo
Taxes:$3,939
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Enjoy the coastal Sarasota lifestyle just minutes from world-famous Siesta Key Beach! Located in the waterfront community of Castel Del Mare, this turnkey furnished 2-bedroom, 2-bath condo combines comfort, convenience, and scenic surroundings in one of Sarasota’s most desirable locations. Inside, the condo features over 1,000 sqft of space with an open living and dining area, laminate flooring, and direct access to the spacious glass-enclosed lanai overlooking lush greenery and the community tennis court. The updated kitchen is designed for both function and style, with solid surface counters, stainless steel appliances, generous cabinet storage, and tiled backsplash. The primary suite offers a spacious walk-in closet and private en-suite bath, while the secondary bedroom includes simple closet space and easy access to the second full bathroom. This residence is ready for immediate enjoyment as a full-time home, seasonal retreat, or investment opportunity. Castel Del Mare is a beautifully maintained intracoastal waterfront community featuring resort-style amenities including two heated pools, tennis courts, kayak storage and launch access, a club house, grilling areas, walking paths, and scenic waterfront seating areas perfect for watching sunsets over Sarasota Bay. Residents also enjoy elevator access, assigned parking, and easy access to a variety of shopping, dining, and boating opportunities. Positioned just over the south bridge to Siesta Key, this location places you moments from powder-soft Gulf beaches, waterfront restaurants, marinas, and vibrant entertainment options. Whether enjoying a day at the beach, exploring nearby nature preserves, or dining along the water, this property delivers the ideal blend of relaxation and access!
Listing is courtesy of: SHOWCASE PROPERTIES OF CENTRAL (352-351-4718)
Listing Agent: Sue Slaubaugh (941-780-3905)
5155 HIDDEN HARBOR RD, SARASOTA, FL 34242
$1,995,000185 Days on yellowkey MLS ID: G5107159
2 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2233 Built: 1973Monthly Fee: $332 Tax: $7,806 (2025)Community: Hidden HarborSpa: NoSingle Family
Taxes:$7,806
Remarks: Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded. Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating access. The home has been thoughtfully renovated with an emphasis on functionality and storage, featuring an updated kitchen, modernized bathrooms, tile flooring throughout, recessed lighting, impact-rated windows and sliders, landscape lighting, a dedicated well with irrigation system, and a heated saltwater pool. Bike to the award-winning Siesta Key Beach, dine and shop in Siesta Village, kayak from your dock to nearby mangrove tunnels, or enjoy the convenience of downtown Sarasota less than seven miles away. A rare waterfront home offering immediate enjoyment and long-term upside in a neighborhood experiencing significant luxury redevelopment.
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
3324 THORNWOOD RD #3324, SARASOTA, FL 34231
$295,000131 Days on yellowkey MLS ID: A4686421
REDUCED by $12,000 (3.9%) on 06/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1981 Tax: $4,017 (2025)Community: Crooked Creek Sec 1Condo
Taxes:$4,017
Elementary School: Wilkinson Elementary
Remarks: Welcome to this beautifully updated ground-floor condo in the quiet, wooded community of Crooked Creek—locally referred to as “the hidden gem” of Sarasota. Surrounded by the 72-acre Red Bug Slough nature preserve, with private community access, this 2-bedroom, 2-bath residence offers the perfect blend of serenity and convenience, just minutes from everything Sarasota has to offer. Crooked Creek’s original two buildings, designed by Sarasota School of Architecture Modernist master architect Tim Siebert, FAIA, are constructed of CMU with stucco and reflect the clean, timeless lines of this iconic design movement. Inside, the home showcases a contemporary coastal aesthetic filled with natural light and thoughtful design. Hardwood floors flow throughout the main living spaces, complemented by stone flooring, built-ins, detailed molding, and plantation shutters, creating a refined and cohesive look. Four sets of French doors open to a stone-floored Florida room, allowing sunlight to pour into the home while offering peaceful views of the surrounding wooded landscape. Just off the kitchen, a private patio provides an additional outdoor space ideal for morning coffee or quiet relaxation. The kitchen features a recessed ceiling, granite countertops, stainless steel appliances, and a stone backsplash—blending both style and functionality. The spacious primary suite easily accommodates a sitting area or workspace and includes a beautifully appointed ensuite bath with double vanity sinks, stone basins and backsplash, tiled walls and floors, and a soaking tub with an overhead rainfall shower. The great room offers custom built-in shelving and a cozy electric fireplace, creating a warm and inviting space for relaxing or entertaining. This home also includes a security system for added peace of mind. Residents enjoy a range of community amenities including a pool, pool house with kitchen, gazebo, grills, tennis and pickleball courts, carport, storage room, and charming pedestrian bridge—all set within a lush, park-like environment. Located in a peaceful natural environment yet just minutes from world-renowned Siesta Key Beach, as well as shopping, dining, and entertainment, this Crooked Creek condo delivers the very best of Sarasota living.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
8501 MIDNIGHT PASS RD, SARASOTA, FL 34242
$29,995,00077 Days on yellowkey MLS ID: A4692839
Bed: 6 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 12000 Built: 2024 Tax: $141,465 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$141,465
Remarks: Set across nearly three acres of pristine waterfront on Siesta Key, Crystal Waters is the most significant private estate in Sarasota—a once-in-a-generation offering that redefines luxury living on Florida’s Gulf Coast. With extraordinary scale, architectural pedigree, and 217 feet of direct Sarasota Bay frontage, this landmark property represents a level of craftsmanship, beauty, and exclusivity rarely seen in the region. Designed by renowned architectural firm Stofft Cooney Architects and custom-built by Chris Jorgensen of Florida West Builders, the Palm Beach-inspired estate encompasses 10,267 square feet with five bedrooms, six full baths, and two half baths. Surrounded by lush tropical gardens and panoramic bay views, every aspect of the property has been conceived to deliver an unparalleled waterfront lifestyle. A dual-gated arrival along a Tabby seashell drive leads to a stately façade framed by towering palms and a grand porte cochère. Beyond solid mahogany doors, a magnificent foyer welcomes guests with travertine floors inlaid with cabochon stone and a sweeping staircase featuring hand-crafted Chippendale railings. Walls of impact glass dissolve the boundary between indoors and out, filling the residence with natural light and uninterrupted views of Sarasota Bay. Refined details include a natural gas fireplace with imported limestone hearth, hand-crafted Vitali European oak flooring in a warm Milano finish, custom millwork, and a serene palette of coastal hues. The kitchen is both a showpiece and gathering place, appointed with custom Campbell cabinetry, Cristallo quartzite surfaces, a custom La Cornue range, dual islands, and walk-in and butler’s pantries. A bayfront breakfast nook and formal dining room open seamlessly to expansive waterfront terraces. Nearby, the clubroom showcases hand-painted Gracie chinoiserie panels, vaulted cypress ceilings, and a wet bar. The first-floor primary suite serves as a private sanctuary overlooking the bay, with French doors opening to the pool terrace. Custom dressing rooms and spa-inspired baths surround a striking octagonal vestibule featuring New Ravenna mosaic floors, Calacatta Matarazzo quartzite, a soaking tub, and marble-clad shower. Upstairs, guest suites, a lounge, and an exercise room provide exceptional accommodations. An Old Florida-style guest residence above a four-car garage offers Pecky Cypress-lined interiors, vaulted ceilings, a full kitchen, covered balcony, and spacious bedroom suite. The main residence is further complemented by an oversized three-car garage. Outdoors, winding pathways lead through beautifully curated grounds to a spectacular 56-foot vanishing-edge saltwater pool that appears to merge with the bay beyond. A covered waterfront pavilion with fireplace, summer kitchen, and tongue-and-groove ceiling creates an elegant setting for entertaining. A private tennis court and lighted pavilion with lounge and fireplace complete the resort-caliber amenities. Along the shoreline, a 90-foot dock extends into Little Sarasota Bay and features a floating kayak launch and a 20,000-pound lift capable of accommodating a 34-foot vessel. Crystal Waters is more than a residence—it is Sarasota’s defining waterfront estate. Unmatched in scale, setting, craftsmanship, and provenance, it stands as one of the finest private properties ever created on Florida’s Gulf Coast. Available lot for sale directly across the street enjoys beach access.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000390 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
8101 GABANNA DR, SARASOTA, FL 34231
$849,000236 Days on yellowkey MLS ID: A4673093
0 Days Off yellowkey (back on 6/7/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2106 Built: 2016Monthly Fee: $570 Tax: $6,729 (2025)Community: Esplanade By Siesta KeySingle Family
Taxes:$6,729
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to the ideally located and coveted Esplanade by Siesta Key—where convenience meets luxury living. Located just minutes from the crystal-sand beaches of Siesta Key, this comfortable, maintenance-free home sits on a large lot at the end of a quiet cul-de-sac. The Taylor Morrison–built Farnese model offers a practical and inviting layout, featuring two en-suite bedrooms, and a den that can easily serve as a third bedroom. The gourmet kitchen is a highlight, boasting a large granite island, solid wood cabinetry, a gas cooktop, and a bright breakfast nook. The spacious primary suite has bay windows overlooking the serene pond, while the primary bathroom includes neutral countertops, double sinks, and a generous walk-in shower. The den provides an ideal office, reading room, or guest retreat. From the great room, sliding glass doors lead to the expansive lanai, where you can enjoy peaceful mornings taking in pond views and local wildlife. Additional features include an outdoor kitchen, tray ceilings, a large laundry room with cabinetry, a half bath, and a two-car garage. Notable upgrades—impact windows and sliders plus a whole-house Generac generator—provide peace of mind during hurricane season. The community’s exceptional amenity center offers a state-of-the-art fitness facility, on site manager, social spaces, a resort-style pool and spa, tennis court, pickleball courts, bocce ball, and a Paw Park. Whether you prefer an active lifestyle or relaxing with friends and neighbors, Esplanade has something for everyone. Centrally located, the community offers convenient access to downtown Sarasota, shopping, dining, and the world-famous Siesta Key. This home delivers the perfect blend of comfort, convenience, and luxury—enhanced by tranquil pond views, abundant recreation, and effortless access to everything the area provides.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Tina Von Kessel (941-266-2848)
2165 SUNNYSIDE LN, SARASOTA, FL 34239
$569,00062 Days on yellowkey MLS ID: A4690142
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1022 Built: 1952 Tax: $5,683 (2025)Community: Hibiscus Park 1Spa: NoSingle Family
Taxes:$5,683
Remarks: Great Opportunity to own your own Mid Century block built cottage near Sunnyside Park, Arlington Park and Sarasota Memorial Hospital, Or build NEW on the 9681 sq ft lot.... Ready to move right in, this 2 bedroom 1 bath home ...Enjoy the great back yard. AC 2014, Roof 2019.. Hot Water Heater 2020.....Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,000103 Days on yellowkey MLS ID: A4689977
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1710 Built: 1960Monthly Fee: $17 Tax: $6,279 (2025)Community: South GateSingle Family
Taxes:$6,279
Remarks: Stunning, mid-century modern home in highly desirable South Gate with views you must see to believe! If you could have picked one of the best lots in South Gate back in the 1960’s this may have been it. The two-bedroom plus office, two bath home sits on a bluff overlooking a wide portion of Philippi Creek including a large aquatic preserve. You’ll be mesmerized by long, unobstructed views in every direction. A nature lovers delight and absolutely intoxicating. But while location is important, there are many more features in this classic home to consider. Entering through the large foyer you’ll immediately notice beautiful terrazzo floors throughout and a great room with vaulted ceilings. There’s an adjacent dining area off the kitchen and all of these spaces look out through what appears to be a “wall of glass” dedicated to the world class view of flora and fauna. The primary bedroom also has views and access to the back yard and the primary bathroom has been upgraded with a separate tub and walk in shower. The den/office can be made more private with sliding pocket doors and function as a guest bedroom. It even has a dedicated, enclosed patio and garden space. There’s an attached, oversized garage with room for your workshop and a double wide driveway with plenty of parking. While this home has been appropriately updated and improved over the years you’ll find it’s all been done with a great sensibility to the original intent, quality and “hipness” so many are learning to appreciate, again.
Listing Agent: Barbara May (404-822-9264)
1829 BOUGAINVILLEA ST, SARASOTA, FL 34239
$4,100,00052 Days on yellowkey MLS ID: A4695800
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4857 Built: 1925 Tax: $13,902 (2024)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$13,902
Remarks: Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate. From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island—ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique. Outside, the magic only continues—enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind. 1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character. Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
1035 SEASIDE DR #603, SARASOTA, FL 34242
$4,600,000251 Days on yellowkey MLS ID: A4672418
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2303 Built: 2023 Tax: $43,735 (2024)Community: Ten35 SeasideSpa: YesCondo
Taxes:$43,735
Remarks: Discover the epitome of luxury living at this stunning beachfront residence, offering an unparalleled blend of modern elegance and coastal serenity. Situated on the penthouse level overlooking the pristine quartz sand of Siesta Key’s Crescent Beach, this exclusive location promises breathtaking Gulf views, stunning sunsets, direct beach access, world class amenities and is perfect for those seeking the ultimate in sophistication and relaxation. Every inch of the 2,562 total square feet of this three bedroom, three and one half bathroom condo has been thoughtfully designed to curate comfort and convenience. The living space, adorned with fetching furnishings and charming décor, offers an open concept with seamless indoor to outdoor integration to the spacious patio and outdoor kitchen with panoramic views of the horizon and when privacy or shade is in order, utilize the advantageous motorized blinds for added comfort. The chef’s kitchen, featuring top of the line cabinetry draped in quartz countertops and state of the art appliances featuring a Wolf gas range, is a masterpiece where inspired coastal cuisine will be a pleasure to create. Preserve your prized wine collection in the attractive wine refrigerator. A true retreat, the luxurious primary suite offers mesmerizing views, a spacious walk-in closet and a spa-inspired ensuite bathroom complete with dual sinks and a glass enclosed shower with multiple shower heads. The two additional bedrooms are generously sized, each offering ample closet space and easy access to elegant ensuite guest bathrooms. From the handsome natural wood flooring to the eye-catching and dazzling light fixtures, this Siesta Key dwelling is intentional in its purpose of granting a tranquil island paradise to you, your loved ones and your furry family members as pets are welcome. For the owner with an interest in income potential, a full service on site rental manage
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
5572 SHADOW LAWN DR, SARASOTA, FL 34242
$4,795,00053 Days on yellowkey MLS ID: A4695248
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3523 Built: 2027Monthly Fee: $17 Tax: $5,171 (2026)Community: Siesta IslesSpa: YesSingle Family
Taxes:$5,171
Tax Year: 2026
Remarks: Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
2763 WOODGATE LN #208, SARASOTA, FL 34231
$245,000513 Days on yellowkey MLS ID: A4641855
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 874 Built: 1979Monthly Fee: $630 Tax: $2,362 (2024)Community: Pinewood Village IiSpa: NoCondo
Taxes:$2,362
Remarks: Attention!!!! This CONDO has a NEW 12 MONTH LEASE at a GREAT Monthly RENTAL !!!! COMPLETELY FURNISHED!!!!Condominium!! Seasonal Snow Birds!!Full-Time Residents!! Investors!!! Great Condo to live-in or rent!!!Completely updated Condo Unit 5 miles from Siesta Key Beach fully furnished. All windows and sliding glass doors updated with UV hurricane Impact Glass!!! Pinewood Village has a Large Heated Pool, Clubhouse, Fitness Center and Shuffleboard Courts. Furniture includes 2 large HD TV's, kitchen was remodeled with Granite Countertops, Stainless Appliances, Wood Cabinets. Both bathrooms have been total re-done. The master suite bedroom has Plantation shutters for privacy, upgraded fixtures in the bathroom and a walk -in closet. Condo was replumbed, new A/C in 2018, and new kitchen in 2019. Centrally located minutes from beaches, shopping and in the Sarasota School District. The low monthly maintenance fees include Cable TV, Community Pool, Insurance, Maintenance Exterior, Maintenance Grounds, Pool Maintenance, Sewer and Water, and Pest Control. Private Storage Unit and Laundry facilities on Condo Floor, elevator and assigned parking. Tenant in place ready to sign an annual Lease with new owner, if desired!!
Listing is courtesy of: EVERBEST REAL ESTATE (941-587-7311)
Listing Agent: Harvey Wasserman (941-587-7311)
3135 ALTA VISTA ST, SARASOTA, FL 34237
$419,900320 Days on yellowkey MLS ID: A4664729
2 Days Off yellowkey (back on 3/11/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1502 Built: 1956 Tax: $310 (2025)Community: Bellevue TerraceSingle Family
Taxes:$310
Elementary School: Alta Vista Elementary
Remarks: LOCATION! LOCATION! Bellevue Terrace! Fantastic opportunity to purchase this beautifully renovated 3 bedroom 3 bathroom home on a very spacious lot. This is an open, split level home with large fenced-in back yard, with room for a pool. The first floor has a large living room/dining room combo, kitchen and half bath. It includes bran new large floor tiles, new hard wood cabinets with quartz tops. All new appliances. The top level has 3 bedrooms with original hardwood floors and 2 full renovated bathrooms. The lower level has a large bonus room that lets lots of light in, and separate laundry room with new washer and dryer leading to the garage. Additional renovations include new shingle roof, electric panel and hot water heater. PVC water lines. The property also has side parking for an RV or Boat. This home is just minutes to downtown Sarasota and a very close proximity to the Lido Beach, Legacy Trail, Payne Park, Sarasota High School, Alta Vista Elementary School, & Sarasota Art Museum. This home gets extra points for its central location. Sarasota City Limits allow for great flexibility for short term rentals on Air BNB, VRBO and short term rentals. Located in the 1-week rental zone. No HOA! Close to the sun kissed beaches of Sarasota, downtown, cultural venues, Big Olaf Ice cream, Yoders Fresh Fruit and Vegetable Market, YMCA, and Locklear Park. Everything is just minutes away. Move quick. Don't miss out.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Brett Decklever (248-766-7571)
2107 PINE TER, SARASOTA, FL 34231
$725,000110 Days on yellowkey MLS ID: S5147369
REDUCED by $20,000 (2.7%) on 06/04/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2016 Built: 1959 Tax: $5,021 (2025)Community: Harbor OaksSingle Family
Taxes:$5,021
Remarks: Fully furnished with a full price... Stunning Turn-Key Dual-Unit Income Property | Fully Renovated Top to Bottom | Prime Sarasota Location This meticulously renovated single-family residence with 4 bedrooms and 3 bathrooms has been completely transformed into a modern, income-producing gem on a spacious 10,048 sq ft lot (approx. 0.23 acres). The property features extensive updates throughout, including brand-new plumbing, electrical, roof, and air conditioning systems. The interior has been beautifully refreshed with a renovated kitchen featuring granite countertops, new cabinets, and an open-concept design, along with tile flooring throughout and fully renovated bathrooms. The exterior boasts fresh stucco paint for enhanced curb appeal. The interior floor plan has been thoughtfully reconfigured to include a completely independent studio unit with its own private entrance, full kitchenette, dedicated washer and dryer, and complete autonomy — ideal for multi-generational living, guests, or maximizing rental income. Both units are beautifully furnished and move-in ready, making this a true turn-key opportunity. Each unit enjoys its own private backyard space, while the generous lot size offers plenty of room to add a pool in the backyard if desired. The property also provides ample parking for multiple vehicles. Perfect for investors or owner-occupants seeking strong short- and mid-term rental performance, this home comes with proven rental records available upon request. The thoughtful design provides privacy and functionality for both living spaces. This fully renovated property offers unbeatable central Sarasota location — just minutes to Siesta Key Beach, downtown Sarasota, and surrounded by an abundance of restaurants, shopping, and entertainment options. Whether you're looking for a low-maintenance primary residence with income potential or a high-performing investment property, this fully updated and furnished dual-unit home delivers exceptional value in one of Sarasota’s most convenient and desirable neighborhoods. Don’t miss this rare opportunity — schedule your showing today!
Listing is courtesy of: DREAMPRENEURS LLC (321-754-1738)
Listing Agent: Laura Ortenzio (321-512-2886)
1624 STICKNEY POINT RD #206, SARASOTA, FL 34231
$369,90090 Days on yellowkey MLS ID: A4691682
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1016 Built: 1975 Tax: $3,939 (2025)Community: Castel Del MareCondo
Remarks: Experience the best of Sarasota living in this beautifully furnished 2-bedroom, 2-bath condominium in the sought-after community of Castel Del Mare. Perfectly positioned at the south bridge to Siesta Key, this community offers a rare combination of waterfront ambiance and everyday convenience just minutes from world-famous Siesta Key Beach. Inside, the open-concept floor plan is bright and inviting, with generous living and dining areas designed for comfort and ease. Large sliding doors lead to a screened lanai and frame serene views of lush tropical landscaping, tennis courts and the intracoastal waterway. The updated kitchen features granite countertops, elegant wood cabinetry, tile flooring and a stylish back splash. The spacious primary suite offers a peaceful retreat with access to the screened lanai, views of the Intracoastal Waterway, an en-suite bath and walk in closet with custom built-ins. A comfortable guest bedroom and second full bath provide privacy for family and visitors. Additional features include impact rated windows and sliders, assigned parking and tasteful furnishings. Castel Del Mare is beloved for its exceptional amenities and unbeatable location. Residents enjoy two heated pools, tennis and pickleball courts, shuffleboard, kayak storage, a fishing pier, bayside gazebo, clubhouse, grilling areas, bike storage and beautifully landscaped grounds. This community offers direct access to the scenic waterfront boardwalk and is just a short stroll to restaurants, shops, marinas and boating options nearby. Whether you are seeking a full-time residence, seasonal escape or investment opportunity, this condo offers outstanding flexibility, strong lifestyle appeal and the relaxed coastal atmosphere that makes Sarasota so desirable. Enjoy sunrise walks, sunset views, dolphins along the bay, and the convenience of being close to everything Siesta Key has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Sarah Lowry (941-400-9026)
527 FREELING DR, SARASOTA, FL 34242
$5,825,000224 Days on yellowkey MLS ID: A4669657
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4310 Built: 2026 Tax: $6,458 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$6,458
Remarks: Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
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