Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
4557 WORCESTER RD, SARASOTA, FL 34231
$450,000174 Days on yellowkey MLS ID: A4675974
REDUCED by $19,000 (4.1%) on 06/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1423 Built: 1998 Tax: $4,659 (2025)Community: Flora-VillaSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,659
Elementary School: Wilkinson Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Located just minutes from the world-famous Siesta Key Beach (less then 6 miles) This newer 3-bed, 2-bath home (built 1998) sits quietly at the end of a dead-end street with no HOA and no CDD fees. The fully fenced yard is ready for pets, gardening, or future outdoor upgrades, while the location keeps you close to everything Sarasota offers—without the restrictions. Minutes from Bee Ridge Park, offering playgrounds, sports fields, shaded picnic areas, and year-round community activities for those who love to be outside. The sellers have already taken care of the big upgrades for peace of mind, including a roof replaced in 2020, a new AC in 2021, updated flooring, with no carpet, a hot water heater installed in 2024, and a brick patio and walkway added in 2024. The stove, washer, and dryer were also replaced in 2024. Lovingly maintained and move-in ready, this home blends comfort with convenience.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
850 S TAMIAMI TRL #630, SARASOTA, FL 34236
$317,500108 Days on yellowkey MLS ID: A4684292
REDUCED by $11,500 (3.5%) on 05/17/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1224 Built: 1998 Tax: $1,963 (2025)Community: Central Park Sec 2 Ph 1Condo
Taxes:$1,963
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: Beautiful townhouse in Central Park II Recently painted with laminant flooring thruout the unit, two bedrooms upstairs each with own bath a half baths located close to downtown. This pet friendly complex has swimming pool , clubhouse and tennis courts. Close to downtown and a short ride to St Armands and the beaches.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Tom Ward (941-350-2463)
7300 COVE TER, SARASOTA, FL 34231
$2,100,000142 Days on yellowkey MLS ID: A4680113
REDUCED by $250,000 (10.6%) on 06/06/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3686 Built: 2009Monthly Fee: $19 Tax: $18,405 (2025)Community: Coral CoveSpa: YesSingle Family
Taxes:$18,405
Elementary School: Gulf Gate Elementary
Remarks: Looking for waterfront living and a boating lifestyle? Look no further! This grand residence, located in Coral Cove, provides direct access to the Intracoastal waterway, yet safely tucked away and situated on an elevated lot well above flood risk. With proximity to one of the top-rated beaches in the US – Siesta Key, this refined home offers flexible and open living spaces – indoor and out. A double-door entry opens to a grand foyer and a spacious great room with a two-story volume ceiling, fireplace, and a wall of sliding glass doors showcasing the saltwater pool and tranquil water views beyond. Extensively renovated in 2009 per public records, this home features four bedrooms and four baths with marble, granite, and Egyptian limestone surfaces throughout. Two of these are full en suites with water views; either can serve as a primary suite – one on the first floor, the other above. The first-floor suite overlooks the pool, spa, and waterway and includes a marble bath accented with onyx lighting. The second floor suite showcases bamboo flooring and a custom en suite bath with stunning Caesarstone quartz walls and flooring, LED lighting inserts, recycled glass, a jetted tub, dual gray Caesarstone vanities, and built-in closets. The gourmet kitchen is appointed with custom distressed wood and cherry cabinetry, a large Victoria Regia granite island, limestone countertops, high-end appliances, and a built-in Miele coffee system. Enjoy tranquil outdoor living and beautiful sunset views from the elevated covered lanai featuring a wood plank ceiling, a summer kitchen with granite countertops, a roll-in grill, and granite tiled decking that surrounds the pool and spa. Hop on your boat from the low-maintenance composite dock with direct access to the Intracoastal Waterway and the Gulf of Mexico. As an owner of this waterfront residence you will have access to the private Coral Cove intracoastal waterfront park and boat launch with a voluntary HOA. Surrounded by tropical landscaping and exterior lighting, this beautiful residence offers luxury finishes and thoughtful design, just minutes from Siesta Key Beach, fine dining, shopping, and the cultural amenities that make Sarasota special. Come see for yourself the extraordinary value this home offers a future owner with vision!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Liz Arme (941-266-4003)
2165 SUNNYSIDE LN, SARASOTA, FL 34239
$569,00024 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)
5600 BEACH WAY DR #315, SARASOTA, FL 34242
$750,000374 Days on yellowkey MLS ID: A4655560
REDUCED by $20,000 (2.6%) on 06/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970 Tax: $7,099 (2024)Community: Beachway AptsCondo
Taxes:$7,099
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Your Florida beach escape awaits — and with a motivated seller, this is an opportunity you won't want to miss.... take a look at this condo that is steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located turn-key, furnished end unit condo is oh so unique on the top floor with views of the beautiful white sandy beach and sparkling blue Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! The rental income is excellent! This recently, completely remodeled from ceiling to floor, wall to wall, unit has 2 bedrooms, 2 bathrooms, hard flooring throughout, a sprawling island, quartz countertops, impact windows and sliders, AND has a spacious balcony, ready for you to relax and enjoy. This unit transfers with $50,000 in furnishings and furniture. This is a perfect place for you to have your dream of a beach life come to reality, with the potential of using it to generate income with monthly rentals. This amazing mid-rise condominium community offers a heated community pool, outside grills, a clubroom with a kitchen, plenty of guest parking and a laundry room on each floor. Recent improvements include newer roofs 2020, a newer elevator 2019, re-plumbed stacks 2018, refreshed landscaping 2020, and new vinyl fencing 2021. The quarterly fee includes access to the heated community pool, basic cable, water/sewer, pest control, weekend on-site maintenance person, and community insurance. Enjoy convenient access to Siesta Key Beach and to Siesta Key Village shops and restaurants with the free trolley service that stops right in front of the Beach Way community, or, walk, orrrrr take a bike cruise to many nearby shops and restaurants… You are not only buying a beach property, you are buying a lifestyle in the beautiful Southwest Florida Sun. This unit can be your own sanctuary escape and your retirement investment... Come see, come sigh and make this Siesta Key lifestyle in the Sun your own.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
1734 WISCONSIN LN, SARASOTA, FL 34239
$1,599,00056 Days on yellowkey MLS ID: A4687427
REDUCED by $51,000 (3.1%) on 05/26/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2910 Built: 2024 Tax: $20,684 (2025)Community: BayviewSingle Family
Taxes:$20,684
Remarks: Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design, energy-efficient construction, and seamless indoor-outdoor flow ideal for entertaining. Located within Sarasota city limits with 7-night minimum rental potential, this property is an outstanding opportunity for both investors and end users seeking a luxury lifestyle close to Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and Siesta Key Beach. Room for a future pool. Located within the coveted Southside school district. Seller financing available with a 5.5% interest-only loan for 2 years.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Keith Kleppinger (941-525-2937)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,00065 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
3504 BENEVA RD #206, SARASOTA, FL 34232
$179,90066 Days on yellowkey MLS ID: A4689854
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 977 Built: 1972Monthly Fee: $510 Tax: $1,980 (2025)Community: Beneva Village Sec 1Condo
Taxes:$1,980
Remarks: This is the one! Gorgeous 2-bedroom, 2-bath fully updated condo—perfect for a first-time homebuyer, second home, or investment property. The unit has been completely renovated from top to bottom, featuring a brand-new kitchen, new appliances, new luxory vinyl floor throughout, and fresh paint. Enjoy peace of mind with a new water heater and newer A/C. The location is unbeatable—just minutes from grocery stores, restaurants, Starbucks, Walgreens, gyms, and more. With easy access to I-75, the beach, and downtown Sarasota, convenience is at your doorstep. Come see it for yourself—this is where value meets quality!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Melinda Vass (407-613-4911)
3469 CLARK RD #268, SARASOTA, FL 34231
$199,90021 Days on yellowkey MLS ID: A4695325
REDUCED by $19,000 (8.7%) on 06/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1974Monthly Fee: $659 Tax: $2,487 (2025)Community: SiennaCondo
Taxes:$2,487
Remarks: Perfect condo for full-time living, seasonal getaways, or an investment opportunity at an affordable price! This charming 3-bedroom, 2-bathroom end unit is being sold turnkey furnished. Beautiful luxury vinyl and laminate flooring throughout the living/dinning area and in all bedrooms, with tile in the entryway, kitchen, and bathrooms. The kitchen offers ample storage, stunning granite countertops, wood cabinetry, and a brand new range. The dining area boasts a built-in dry bar, perfect for entertaining guests. Water heater 2022, A/C 2023, Washer 2024, NEW ROOF! The community has a heated pool, tennis courts, BBQ area and a fenced around dog run. The monthly fee includes: water, sewer, trash collection, building insurance and exterior maintenance including the roof and grounds.Conveniently located near excellent shops and restaurants, this condo is just 3 miles from Crescent Beach and only 4 miles from Siesta Key Public Beach. Sarasota downtown, the Ringling Museum, Selby Gardens, St. Armands Circle, Island Park, Marina Jack's Harbor,.... are only a short drive away.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Judit Turan (941-993-8300)
3424 TANGLEWOOD DR, SARASOTA, FL 34239
$899,00028 Days on yellowkey MLS ID: A4694194
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3147 Built: 1962Monthly Fee: $17 Tax: $8,708 (2025)Community: South GateSingle Family
Taxes:$8,708
Remarks: Welcome to this lakefront retreat with a private guest suite with direct access to Phillippi Creek located in Southgate! This is a rare opportunity to own private waterfront with access to scenic Phillippi Creek and the Intracoastal Waterway. This exceptional property combines timeless design, modern upgrades and Florida indoor-outdoor living, all with no history of hurricane water intrusion, according to the owner. From the moment you arrive, the home’s curb appeal impresses with a circular driveway, paver walkways, an additional paver parking pad, mango and avocado trees and a fully fenced setting surrounded by lush, mature landscape. Enter through stunning French doors with stained glass into a bright, tropical-inspired entry. Inside, the open-concept living space is expansive and inviting, anchored by a gas fireplace and enhanced by updated windows that fill the home with natural light. The chef’s kitchen is functional and stylish, featuring a curved stone countertop and bistro-height seating, Murano glass pendants and recessed lighting, a six-burner natural gas cooktop and stainless-steel appliances, including a Bosch dishwasher. Designed for entertaining, the outdoor living area is exceptional. Enjoy an expansive paver patio with a tranquil wall-mounted fountain and a summer kitchen with a gas grill, refrigerator, sink, single gas burner and an exterior-vented commercial-grade hood. The backyard overlooks serene views of Lake Seclusion and the dock. Watch the ducks, herons, egrets, cormorants and leaping fish. The primary suite is a private sanctuary, spacious, light-filled and surrounded by glass sliders opening to the patio with peaceful water views. Features include dual oversized walk-through closets, an elegant en suite bath with split vanities, granite countertops, a jetted soaking tub on an elevated platform and a walk-in shower with glass block detail and water closet. Further highlights in this wing are two more large bedrooms with a shared bath, walk-in shower and pedestal sink. Another standout feature of this home is the fully equipped multigenerational living suite/home office/artist studio complete with a private entrance and courtyard, separate air-conditioning system and kitchen with appliances. The suite has a living room/bedroom combo and a full bath with a new tile shower and linen closet. Connecting the guest suite with the three bedrooms and two baths is a spacious butler's pantry with a full-size refrigerator and wine chiller as well as a washer, dryer, utility sink and extensive storage. The oversized attached garage has an updated automatic door opener motor, cabinets and shelving. In the backyard are the Rinnai tankless gas water heater, a well-fed irrigation system, exterior lighting, a private outdoor shower and a small storage shed. The roof was replaced in 2022 and one of two AC units was replaced the same year. This is more than a home; it’s a private retreat offering flexibility, functionality and exceptional waterfront living plus the option of income production. It is minutes from downtown, the beach and shopping without the inconvenience of bridges or seasonal traffic. The desirable neighborhood is quiet and stable with mature trees lining the gently curving street. Remarkably, this house has had only three owners, a sign of how special it is to live there.
Listing Agent: Cindy Taliaferro (941-894-7269)
4708 OCEAN BLVD #E7, SARASOTA, FL 34242
$2,299,000269 Days on yellowkey MLS ID: A4665893
REDUCED by $51,000 (2.2%) on 05/04/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,841 (2025)Community: Windward PassageCondo
Taxes:$16,841
Remarks: Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277 square feet with miles of Gulf-front views, the residence has been thoughtfully redesigned with wide-plank European engineered oak flooring, impact-rated windows and doors, and integrated smart-home technology throughout. The chef’s kitchen is a statement in both form and function, featuring custom cabinetry, Milano Dolomite countertops, a striking Macaubas Quartzite island, and premium GE Café appliances—perfect for entertaining against a backdrop of endless blue water. The primary suite is a private retreat with direct access to a Gulf-front balcony and a spa-inspired bath complete with dual vanities, rainfall shower, and bidet. Two additional guest suites provide comfort and privacy, each finished with designer details. Additional highlights include a two-car tandem garage with hurricane-rated door, new HVAC systems, electric hurricane shutters, and an integrated sound and entertainment system. Amenities include a heated pool, guest parking, and direct walking access to the sugar-white sands and vibrant Village of Siesta Key. This residence blends timeless coastal elegance with modern luxury—an extraordinary Gulf-front retreat on one of Siesta Key’s most coveted stretches of shoreline.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Stacey King (646-734-5014)
3942 HAMILTON CLUB CIR #13, SARASOTA, FL 34242
$1,349,00014 Days on yellowkey MLS ID: A4696120
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2691 Built: 1997 Tax: $10,009 (2025)Community: Hamilton ClubSingle Family
Taxes:$10,009
Remarks: Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming arms" staircases . Very close to the Village and Beach , yet equally convenient to Downtown . This sophisticated townhome has been completly renovated with fine finishes , wood and stone prevail with architectural beauty . Soaring ceilings bring in the most elegant lighting . The kitchen with its sweeping bar of magnificent granite can accomodate a large party-open to the Great Room , it is both sleek and inviting .Premium appliances include Miele, Bosch , GE and KitchenAid .Expansive counter space , built in shelving and a variety of pantries and drawers add to the incredible functionality. The Great Room with 20 foot ceilings opens to the screened balcony with a charming view of the lagoon and pool area . The primary bedroom is enhanced by the stunning view of treetops and is all the more cozy for having its own fireplace . Impact rated windows and a metal roof combine to make this solid structure weather worthy . On the ground floor , in addition to the oversized two car gargage is a climate controlled bonus room which opens to the ground floor lanai . Boating , swimming , tennis and walking paths , within a private and peaceful environment close to everything -that is the Hamilton Club .
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Barbara Dumbaugh (941-349-3444)
3281 BENEVA RD #202, SARASOTA, FL 34232
$196,90014 Days on yellowkey MLS ID: TB8516148
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1979Monthly Fee: $438 Tax: $1,763 (2025)Community: Village Brooke Sec 3Spa: NoCondo
Taxes:$1,763
Remarks: Welcome to your beautifully updated 2-bedroom, 2-bathroom condo, offering the perfect blend of modern finishes and Florida resort-style living! Step inside to find fresh tile flooring in the kitchen and baths, luxury laminate wood floors, and brand-new carpet and pad in the bedrooms. The kitchen is a showstopper, featuring crisp shaker cabinets, solid stone countertops, a sleek subway tile backsplash, and new matching stainless steel appliances. Both bathrooms have been thoughtfully updated with new vanities and modern finishes. The spacious master suite includes a private bath and a large walk-in closet for added convenience. Enjoy relaxing mornings and breezy evenings on your oversized balcony with views of the tennis courts and lush green space. Community amenities include a sparkling pool, tennis courts, and shuffleboard courts, perfect for embracing the Florida lifestyle year-round. Additional highlights include a brand-new water heater, ceiling fans,stylish new fixtures throughout, and more — making this home move-in ready and ideal for your next chapter in the Sunshine State!
Listing is courtesy of: REALNET FLORIDA REAL ESTATE (813-288-8000)
Listing Agent: Greg Vander Wel (813-565-2998)
980 CHARLOTTE AVE, SARASOTA, FL 34237
$375,00014 Days on yellowkey MLS ID: A4696068
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 839 Built: 1962 Tax: $3,966 (2025)Community: Robin Hood WoodsSingle Family
Taxes:$3,966
Elementary School: Alta Vista Elementary
Remarks: CHARMING COTTAGE JUST 2 MILES FROM DOWNTOWN SARASOTA Nestled on a peaceful street, this well-loved cottage offers the perfect blend of comfort and convenience. Featuring numerous updates, including a NEW ROOF, screened-in lanai, water heater, and waterproof vinyl flooring, this TURNKEY home is move-in ready. The windows were replaced in 2011, and plumbing was jetted and lined under the house in 2012. This property is perfect for 1st time homeowners, Air BnB, an investor, etc. Located less than half a mile from the Legacy Trail, you can easily bike to vibrant downtown Sarasota or explore the nearby Pinecraft area, famous for its charming markets, coffee shops, and restaurants. A short drive takes you to the stunning Siesta Key and Lido Beach, known for their pristine sand and breathtaking ocean views. Whether you're seeking a peaceful retreat or a vacation home, this delightful cottage is the ideal spot in Sarasota.
Listing Agent: Anna Martin (941-539-6601)
1829 BOUGAINVILLEA ST, SARASOTA, FL 34239
$4,100,00014 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)
4001 GROVELAND AVE, SARASOTA, FL 34231
$1,500,00050 Days on yellowkey MLS ID: A4691652
Bed: 10 Bath: 0.0 Liv Area Sq Ft: 4291 Built: 1974 Tax: $13,014 (2025)Community: Grove ParkSpa: NoApartment
Taxes:$13,014
Remarks: LOCATION LOCATION LOCATION! Sarasota's hottest zip code is Presenting a strong multifamily investment opportunity just minutes from Siesta Key, this 5-unit hotel/ motel property offers current income, flexible rental options, and long-term upside in one of Sarasota’s most desirable rental markets. Located in a non-flood zone approximately 4 miles from Siesta Key Beach, the property is well positioned for long-term tenants, seasonal rentals, or potential short-term rental strategies. The building includes five 2-bedroom, 1-bath units, each offering broad tenant appeal and turnkey convenience. Long-term tenants are currently in place, while the property has the availability to hold a motel/hotel license, creating additional flexibility for future ownership and rental operations. Investor-friendly features include individually metered utilities, public water and sewer, paved parking, no required flood insurance, and reported general liability insurance of approximately $460. Recent improvements include exterior paint in 2024, remodeled kitchens in Units 2, 3, and 4 in 2024, updated bathrooms, major plumbing replacement completed in 2009 and 2010, roof replacement in 2014, blown-in roof insulation. The property also offers private amenities that help set it apart from typical multifamily options, including a heated and cooled swimming pool, screened patio room, and tropical outdoor space designed to enhance tenant or guest enjoyment. With current income, multiple rental strategy options, turnkey units, and a prime Sarasota location near Siesta Key, this property is a compelling opportunity for investors seeking cash flow, flexibility, and long-term appreciation potential. Schedule your private showing today.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
5201 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,450,000135 Days on yellowkey MLS ID: A4680975
0 Days Off yellowkey (back on 6/5/2026)
REDUCED by $45,000 (3.0%) on 04/30/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2802 Built: 2008 Tax: $6,145 (2025)Community: Sarasota BeachSpa: NoSingle Family
Taxes:$6,145
Remarks: Under contract-accepting backup offers. WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.
Listing Agent: Mary Kassen (941-900-9776)
239 HOURGLASS WAY #V7, SARASOTA, FL 34242
$640,00040 Days on yellowkey MLS ID: A4691064
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1327 Built: 1968Monthly Fee: $1,793 Tax: $5,346 (2025)Community: Whispering SandsVilla
Taxes:$5,346
Remarks: Tucked away in a peaceful, private setting overlooking the tranquil, shimmering lagoon - with its abundant fish, birds, and aquatic life - this beautifully updated 3 Bed/2 Bath villa in the premier GULF FRONT property of Whispering Sands offers the perfect blend of comfort, style and serenity. Step inside to discover a bright NEW kitchen featuring new granite countertops, stainless appliances, recessed & under cabinet lighting and an open, inviting feel ideal for everyday living and entertaining alike. Engineered wood flooring flows throughout the home, complemented by neutral paint tones, new interior doors, and thoughtfully updated baths with granite counters, new vanities and modern fixtures. A spacious screened brick paver lanai extending the full length of the residence may well be the star of the show, creating an ideal private indoor-outdoor living space to relax and enjoy the lush tropical surroundings. A private fenced brick paver patio offers an additional retreat for entertaining, dining al fresco, or simply unwinding in the Florida sunshine. Additional upgrades include a newly painted 1-car garage with new full-sized washer and dryer and new sink. The freshly painted front door, new screen door - along with a brick paver sidewalk and driveway - enhance the home’s welcoming curb appeal. Newly painted exterior in 2025. New landscaping is planned for the complex in 2026. Whispering Sands is a 55+ Gulf front property offering 800’ of PRIVATE beach, 2 heated pools, beachside Tiki Hut and grills, shuffleboard, & canoe/kayak storage. The clubhouse is currently undergoing complete remodeling and will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events. Ideally located just around the corner from the shops and restaurants of Siesta Key Village, this move-in ready property combines stylish updates, abundant outdoor living space, and a truly peaceful location to create the perfect coastal retreat!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
2516 BROWNING ST, SARASOTA, FL 34237
$1,399,000252 Days on yellowkey MLS ID: A4666531
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2746 Built: 2026 Tax: $1,990 (2023)Community: Hudson ParkSpa: NoSingle Family
Taxes:$1,990
Tax Year: 2023
Remarks: Brand-new modern two-story home, offering luxury living and exceptional investment potential in the heart of Sarasota. This thoughtfully designed residence features 5 bedrooms, 4 bathrooms, and an attached 2-car garage, with an open-concept kitchen and living space showcasing premium Italian-imported flooring, cabinetry, and designer fixtures. Large sliding doors open seamlessly to a private outdoor deck and pool, creating the perfect setting for entertaining and enjoying Florida’s indoor-outdoor lifestyle. Located within Sarasota city limits, this property qualifies for weekly rentals, making it an outstanding opportunity for a primary residence, seasonal retreat, or income-producing investment. Just minutes from Downtown Sarasota, Siesta Key Beach, and St. Armands Circle, with convenient access to world-class dining, boutique shopping, cultural attractions, and Sarasota’s award-winning Gulf beaches. Nearby parks, tennis and pickleball courts, and the Legacy Trail extension provide endless outdoor recreation. Secure a brand-new modern Sarasota home in a highly desirable location.
Listing Agent: Rinat Sikdar (941-993-9292)
1640 WALDEMERE ST, SARASOTA, FL 34239
$6,500,000103 Days on yellowkey MLS ID: A4685215
INCREASED by $50,000 (0.8%) on 06/05/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5270 Built: 2026 Tax: $8,031 (2026)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$8,031
Tax Year: 2026
Remarks: Almost finished!!! Completion 3 weeks!!! Touch-ups and Staging in process now. Modern Luxury Villa | 1640 Waldemere St Experience the pinnacle of Gulf Coast luxury in this stunning Miami-style modern villa, perfectly situated West of Trail in one of Sarasota’s most coveted neighborhoods. This architectural marvel blends high-end technology with effortless coastal living, offering a sanctuary just minutes from the vibrant pulse of Downtown Sarasota and the world-renowned sands of Siesta Key and Lido Beach. The Residence Designed for the connoisseur of fine living, this home boasts a sleek, minimalist aesthetic defined by clean lines and expansive glass. Elevated Living: Move effortlessly between floors with your private elevator. The Great Indoors/Outdoors: Massive automated glass doors disappear to create a seamless transition to the resort-style pool deck, perfect for year-round entertaining. Privacy at Your Fingertips: Equipped with cutting-edge Smart Glass technology, windows transition from transparent to opaque instantly for ultimate privacy. Space for Everything: Featuring 5 spacious bedrooms, a dedicated executive office, and a private home gym, there is no better lifestyle or utility. Tech-Forward Luxury This is a fully realized Smart Home, designed for total control and ambiance: Integrated Smart Home System: Control lighting, climate, and security from your device. Whole-Home Audio: An immersive sound system flows through every room and out to the pool deck. Modern Finishes: Premium materials and high-end fixtures throughout reflect a commitment to quality and contemporary style. The Location Located West of 41, 1640 Waldemere St places you in the heart of Sarasota’s most desirable "West of Trail" district. You are seconds away from: Sarasota Memorial Hospital and the medical district. Downtown Sarasota’s fine dining, opera, and boutiques. St. Armands Circle and local beautiful sand beaches. Live the Future of Luxury. This villa isn't just a home; it’s a statement. Call for all details…
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
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