Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3541 WILKINSON WOODS DR #40, SARASOTA, FL 34231
$289,900163 Days on yellowkey MLS ID: A4672490
REDUCED by $5,000 (1.7%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1980 Tax: $3,658 (2025)Community: Wilkinson WoodsVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,658
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. Skip the renovation stress and discover an UNBEATABLE VALUE in this updated 2-bedroom, 2-bath attached villa, offering IMPACT WINDOWS, New A/C (2026) and NEWER APPLIANCES. Bathed in natural light, this home features elegant QUARTZ COUNTERTOPS throughout, designer LED-illuminated mirrors, and sleek, durable laminate flooring. Beyond the stylish interior lies a charming paver patio—a relaxing retreat for morning coffee or sunset breezes. Located in an enclave that feels like a hidden secret in South Sarasota, you are minutes from Siesta Key’s white sands, casual and world-class dining, entertainment...but miles from the stress of a fixer-upper. Experience just how effortless Florida living can be by taking this stylish, move-in-ready villa off your screen and scheduling your in-person tour today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Elisa Gersman (941-735-0595)
5619 NEW YORK AVE, SARASOTA, FL 34231
$399,000203 Days on yellowkey MLS ID: A4664577
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1577 Built: 1959 Tax: $3,645 (2025)Community: Sun HavenSingle Family
Taxes:$3,645
Elementary School: Gulf Gate Elementary
Remarks: Welcome to 5619 New York Avenue, a charming Sarasota retreat where comfort, style, and convenience come together beautifully. Nestled in a quiet neighborhood with no HOA, this home offers the freedom to truly make it your own while being just minutes from Siesta Key Beach, Downtown Sarasota, and all the coastal lifestyle has to offer. As you arrive, refreshed tropical landscaping and a welcoming curb appeal set the tone. Step inside to find a bright, open layout designed for easy living and connection. Natural light fills every corner, reflecting off tile floors that create a clean and calming atmosphere. The kitchen opens to the living space, perfect for entertaining or relaxed family gatherings, while large sliding doors invite you to step outside and experience the home’s centerpiece, your private backyard oasis. Out back, the sparkling pool is surrounded by lush greenery, offering a peaceful escape where you can unwind, host weekend barbecues, or simply soak up the Florida sun. The fenced yard provides privacy and room for pets or gardening, creating a perfect blend of relaxation and functionality. Whether you are looking for a full time residence, a seasonal getaway, or an investment opportunity, this home captures what makes Sarasota living so desirable. You are close to the area’s top beaches, shopping, dining, and cultural attractions, yet tucked away in a neighborhood that feels like your own personal retreat. This is your chance to own a pool home in Sarasota that combines character, comfort, and location while giving you the freedom of no HOA restrictions. Experience the lifestyle you have been dreaming of at 5619 New York Avenue.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Jesse Bauer (941-465-8583)
7345 PINE NEEDLE RD, SARASOTA, FL 34242
$2,350,0002 Days on yellowkey MLS ID: A4690626
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2977 Built: 1956Monthly Fee: $450 Tax: $10,699 (2025)Community: Sanderling ClubSingle Family
Taxes:$10,699
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Remarks: Beautifully renovated 4-bedroom, 4-bath pool home tucked behind the gates of the exclusive Sanderling Club. Surrounded by a grandfathered privacy wall and lush tropical foliage, the property is just steps from your own private beach. 2023 updates include - new roof, hurricane-impact windows/sliders and plumbing. Meticulously renovated in 2025–2026 with top-of-the-line finishes throughout the entire home. Luxury vinyl plank flooring flows through the open floor plan, complemented by granite countertops and a oversized granite island with lots of storage, Samsung appliances and an open-concept layout ideal for entertaining, with abundant indoor/outdoor living space with views of the oversized sparkling pool. The primary suite is a tranquil retreat with two walk-in closets and an en-suite bath featuring a double vanity and soaking tub. A thoughtful split plan offers two additional spacious bedrooms each with en-suite baths. A fully renovated pool house/mother-in-law suite with its own full bath adds flexible living options. Located in a waterfront community, residents of the Sanderling Club have exclusive beachfront access, tennis and pickleball courts, clubhouse and 24-hour security This home blends refined luxury with coastal lifestyle and privacy.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Amy Nadell (941-539-5424)
2375 BAHIA VISTA ST, SARASOTA, FL 34239
$512,000252 Days on yellowkey MLS ID: A4662778
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1092 Built: 2022 Tax: $5,587 (2024)Community: Avon Heights 2Single Family
Taxes:$5,587
Elementary School: Alta Vista Elementary
Tax Year: 2024
Remarks: Elevate your lifestyle in this unique island-style home in the heart of Sarasota! An exceptional opportunity to experience the best of Florida living and an effortless move-in with all turnkey furnishings included, allowing you to settle in immediately. The interior is bright, optimized, and beautifully finished with luxury vinyl floors, shaker style cabinets, smooth finish doors, and smart TVs throughout, creating a modern and inviting atmosphere. The spacious living room and alcove with an antique bar cart and desk are adjacent to the dining area and a fully equipped kitchen, featuring elegant stone countertops and "smart" Samsung stainless steel appliances—ideal for entertaining guests or enjoying family meals. For your convenience, the interior laundry area includes a Samsung washer and dryer. This delightful home, built in 2022 to current building codes, ensures peace of mind with optimal construction features including impact windows, durable metal roof, and elevated stilt-on-concrete-piling construction with ample under-building carport style parking for two cars. With three bedrooms and two full baths, it comfortably sleeps eight, making this home perfect for families or groups. Located in a coveted area between vibrant downtown Sarasota and gorgeous Gulf Coast beaches, you can easily walk to Arlington Park and Aquatic Complex, head to Lido Key Beach or world-famous Siesta Key Beach with its quartz crystal sand, or simply relax in the serene, tree-lined backyard. This home is currently used as a part-time vacation home and for weekly vacation rentals. It's ideal as a full-time residence, a convenient part-time vacation home, or for continued weekly rentals, offering flexible ownership options. You will also love the close proximity to Sarasota's vibrant arts and culture scene, diverse dining venues, Sunday Farmers Market, the stunning Sarasota Bayfront and marina, and abundant recreational activities.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Dennis Kotaska, Llc (941-815-6772)
2614 CROTON AVE, SARASOTA, FL 34239
$695,0002 Days on yellowkey MLS ID: A4691649
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2110 Built: 1962 Tax: $3,703 (2025)Community: South Gate ManorSingle Family
Taxes:$3,703
Remarks: Modern Luxury Meets Mid-Century Charm in the Heart of Southgate. Prepare to be captivated by this Mid-Century Modern gem, situated on nearly a quarter-acre in one of Sarasota’s most sought-after neighborhoods. This 3-bedroom, 2-bathroom residence with a dedicated office offers a rare combination of refined design and true “big-ticket” peace of mind. Step inside over freshly restored and sealed terrazzo floors and into a sun-drenched, open floor plan. The chef’s kitchen was expertly expanded in 2025 and features crisp quartz countertops, premium Bosch appliances, and custom cabinetry. The dining area is a true conversation piece, showcasing a contemporary wood-accent wall with a seamlessly integrated jib door that reveals a brand-new, dedicated LAUNDRY SUITE (2024), complete with an abundance of custom storage and a sink. The spacious guest bathroom has been fully remodeled in 2025 and both bathrooms have high-end Kohler fixtures. Every detail throughout the home has been thoughtfully addressed, from new baseboards to freshly painted ceilings (2026). This home has an extensive list of recent upgrades: Roof: brand new in 2025, including TPO on slanted surfaces. HVAC (2023), new ductwork and new full attic insulation (2024); new water heater (2025); new electrical panel/fuse box (2024). Plumbing: All pipes professionally relined (2024); new gutters and French drains installed. The exterior transformation (2024–2025) is equally impressive. A new circular driveway and paved walkway lead to a modern, refaced façade and a striking new front door. The front yard has been thoughtfully redesigned with new landscaping and enhanced by solar-powered exterior lighting. The oversized, fenced backyard offers exceptional space for a future pool and expansive outdoor living. A brand-new screened lanai (2024) and new shed complete this private outdoor retreat. Located just minutes from Sarasota Memorial Hospital, Southside Village, and downtown Sarasota, this Southgate standout is truly move-in ready. With so many upgrades and abundant room to personalize the outdoor space, the only thing left to do is move in and enjoy the Sarasota lifestyle!!! COME AND MAKE THIS HOUSE YOUR HOME!!!
Listing Agent: Maryna Haiduk (954-732-4122)
1612 STARLING DR #101, SARASOTA, FL 34231
$324,9996 Days on yellowkey MLS ID: A4691379
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1794 Built: 1987 Tax: $4,227 (2024)Community: The Landings, Landings South IvSpa: YesCondo
Taxes:$4,227
Remarks: Nestled in the tranquil embrace of The Landings, this totally renovated ground floor coach home offers an unparalleled fusion of comfort and class and is being offered turnkey furnished for immediate enjoyment. Architecturally delightful and bathed in natural light, the residence boasts an open floor plan that spans approximately 1,794 square feet of living area. The large living room is the quintessential space for hosting gatherings, celebrating special moments, and creating unforgettable memories. With its expansive layout, the well-designed living room can accommodate a variety of activities and guests, making it the perfect hub for entertainment. The gourmet kitchen is a chef’s dream, adorned with rich custom cabinetry, a breakfast bar, and granite counters. Adjacent to the kitchen, the glass Florida room invites you to savor serene lakeside views and unwind in the beauty of your surroundings. Volume ceilings throughout the home enhance the feeling of openness and elegance. This sophisticated home features two spacious bedrooms and two full baths, providing ample space for relaxation and privacy. The elegant waterfront owner's suite is a haven of peace, complete with two walk-in closets and a contemporary bath highlighted by a stylish walk-in shower. An additional bedroom serves as a versatile virtual workspace or a welcoming guest room for family and friends. Step outside to the inviting patio, perfect for basking in the natural beauty and tranquility of The Landings. The oversized one-car garage offers ample storage space for bikes, kayaks, or canoes, completing the picture of convenience and functionality. Residents of The Landings enjoy an array of amenities designed for relaxation and recreation. The community pool, ensconced in lush Floridian foliage and bordered by a tranquil lake, is an ideal spot to unwind. The private Landings Racquet Club membership provides access to 8 Har-Tru tennis courts, a fitness center, meeting rooms, and a library. The Landings offers 24-hour security, ensuring peace of mind for its residents. The community is set in a gorgeous natural environment with direct access to Sarasota Bay, creating a perfect blend of beauty and safety. Situated in one of Sarasota’s finest and best-located communities, The Landings is surrounded by excellent schools and a plethora of dining, culture, beaches, and shopping options just a short drive away. This coach home in The Landings represents the epitome of refined living, offering a serene retreat amid natural beauty, with all the comforts and conveniences one could desire. Welcome to your new home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Stephanie Church (941-724-5448)
1654 STARLING DR #201, SARASOTA, FL 34231
$299,000849 Days on yellowkey MLS ID: A4593452
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1775 Built: 1987 Tax: $4,584 (2024)Community: Landings South V, The LandingsCondo
Taxes:$4,584
Remarks: One or more photo(s) has been virtually staged. Discover the perfect blend of space, comfort, and opportunity in this desirable three-bedroom, two-bath end-unit condominium located in the highly sought-after gated community of The Landings. Enter through the welcoming first-level foyer and ascend to the light-filled main living area, where vaulted 13-foot ceilings create an airy, open ambiance. With approximately 1,775 square feet of living space, this residence offers a well-designed split floor plan that ensures privacy while maintaining an effortless flow for everyday living and entertaining. The living and dining areas seamlessly connect to the kitchen, complete with a convenient pass-through bar—perfect for hosting gatherings or casual dining. The spacious primary suite serves as a relaxing retreat, featuring a large walk-in closet and an oversized ensuite bath with dual sinks and a spa-inspired shower. Two inviting guest bedrooms provide comfortable accommodations for family or visitors. Enjoy peaceful moments on the screened lanai, surrounded by lush natural scenery, or take advantage of the attached one-car garage for added convenience. As a resident, you’ll have access to The Landings Racquet Club, offering 8 Har-Tru tennis courts, pickleball, a heated swimming pool and spa, fitness center, meeting rooms, and a library—the perfect extension of your home and lifestyle. Set within a secure, 24-hour guard-gated community, The Landings is renowned for its scenic walking trails, lush tropical setting, and direct access to Sarasota Bay. Ideally situated near top-rated schools, world-class dining, shopping, arts, and the beautiful Gulf Coast beaches, this community embodies Sarasota living at its finest.
300 GARDEN LN, SARASOTA, FL 34242
$2,999,000237 Days on yellowkey MLS ID: A4662830
REDUCED by $200,000 (6.3%) on 04/01/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,545
Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
2927 WEBBER ST, SARASOTA, FL 34239
$575,000107 Days on yellowkey MLS ID: A4678196
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1961Monthly Fee: $17 Tax: $6,193 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,193
Elementary School: Southside Elementary
Remarks: Wonderful mid-century ranch in Southgate offering 3 spacious bedrooms, 2 bathrooms, a 2-car garage, and a heated saltwater pool. The dining room and living room both feature walls of pocket sliding doors that open to a large covered patio and screened pool area—perfect for enjoying the indoor-outdoor Florida lifestyle. Inside, restored terrazzo floors keep the home cool and timeless. The updated kitchen features stainless steel appliances, granite countertops, and a farmhouse sink. The primary suite includes a walk-in closet, and both bathrooms have been updated with marble tile and granite countertops. A convenient pool bath opens directly to the outdoor area. The heated saltwater pool was converted and upgraded in 2021 with a new pump, heater (2025), LED lighting, fountain feature, and solar cover. A fully fenced backyard and fire pit create a private outdoor setting ideal for entertaining or relaxing. Hurricane-impact windows were installed in 2021, along with extensive upgrades inside and out. The home features a newer roof (2022), A/C (2018), and new ductwork installed in 2022. There is ample space in the front of the property to add a circular driveway if desired. Optional membership is available to the South Gate Community Association, offering access to a community pool, park, and recreation facilities. Ideally located close to world-renowned beaches, downtown Sarasota, cultural attractions, outdoor trails, and highly rated schools.
Listing Agent: Fred Sassen (404-408-5956)
3700 S OSPREY AVE #219, SARASOTA, FL 34239
$209,00075 Days on yellowkey MLS ID: A4682528
REDUCED by $15,900 (7.1%) on 04/29/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 991 Built: 1979 Tax: $2,688 (2025)Community: Plaza GardensCondo
Taxes:$2,688
Remarks: West of the Trail location perfect for going to the beach or Downtown. Perfect for a winter getaway or full time living. 2nd floor unit with enclosed patio. Beautiful gardens and trees surround the property. 2 bedroom 1 bath (room for another 1/2 bath), dual sinks, on-site laundry, elevator and pets are welcome! A Washer & Dryer may be installed in the unit.One designated parking spot and guest parking available. Water and basic cable included.
Listing Agent: Kelly Anderson (941-320-6115)
4939 PEREGRINE POINT WAY, SARASOTA, FL 34231
$1,685,00092 Days on yellowkey MLS ID: A4680225
REDUCED by $114,000 (6.3%) on 04/07/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3828 Built: 2000Monthly Fee: $196 Tax: $8,043 (2025)Community: The LandingsSingle Family
Taxes:$8,043
Remarks: A Masterpiece in The Landings' Most Coveted Enclave. Presenting a rare opportunity to acquire an impeccably crafted residence on the sought-after cul-de-sac of Peregrine Point Way. Built in 2002 with meticulous attention to feng shui principles, this single-level sanctuary spans over 3,800 square feet of thoughtfully designed living space, offering the perfect blend of sophistication, flow, and modern convenience. Grand First Impressions A circular driveway sets the stage for this distinguished residence. Pass through custom wooden gates into an impressive formal Florida entry courtyard, where a striking bronze fountain creates an unforgettable "wow factor" for arriving guests. This exceptional entry experience speaks to the caliber of craftsmanship found throughout. Exquisite Interior Details Marble flooring flows gracefully throughout the main living areas, establishing an elegant foundation for refined living. The thoughtful split floor plan ensures both privacy and space, while the single-level design provides effortless flow, a rare find in the homes of this caliber. The formal living room exemplifies true feng shui design, creating a seamless visual and physical connection to the resort-style outdoor spaces beyond. An adjacent formal dining room provides the perfect setting for sophisticated entertaining, whether hosting intimate dinners or grand celebrations. Luxurious Private Quarters The expansive primary suite serves as a serene retreat, featuring a spa-inspired marble bath with a soaking tub, dual vanities, and a walk-in shower. A generously proportioned custom walk-in closet provides exceptional organization and storage. Each of the home's four bedrooms includes an ensuite bathroom, a hallmark of luxury living that ensures privacy and comfort for family and guests alike. Custom-built closets throughout reflect the meticulous attention to detail. The fourth bedroom, currently appointed as an office with custom built-in cabinetry, offers flexibility for those who work from home or desire a private study. Resort-Style Outdoor Living. Step outside to discover your private oasis. The expansive screened-in lanai extends your living space into nature, perfect for year-round entertaining in comfort. The stunning pool area features a dramatic tall tile fountain whose soothing sounds create an atmosphere of tranquility. Mature landscaping artfully balances sun and shade, while a covered seating area invites quiet contemplation or spirited conversation. This is outdoor Florida living at its finest designed for those who appreciate the art of entertaining and the beauty of serene moments alike. The Landings Lifestyle. Peregrine Point Way's naturally serene cul-de-sac location is among the most desirable in The Landings. This prestigious community offers winding tree-canopied roads, pristine lakes, nature trails, and Roberts Bay access an idyllic backdrop for an elevated lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
436 CANAL RD #A, SARASOTA, FL 34242
$1,795,00088 Days on yellowkey MLS ID: A4678784
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2756 Built: 2002 Tax: $19,424 (2025)Community: Siesta Villas 1Townhouse
Taxes:$19,424
Remarks: Superb Location. Big Family Retreat. Excellent Investment. Quiet Beach Days. The search for your ultimate beach retreat ends at 436 Canal Road. This 3-bedroom, 3 ½ bath home has all the extras you’re looking for. Your home is located just steps to world famous Siesta Key Beach. You are an easy walk, bike ride, or golf cart drive to Siesta Key Village where you will experience great food, entertainment and eclectic shopping. Enjoy fishing or dropping your kayak or paddleboard off your private community dock to explore Siesta Key by water. Or relax by the west-facing pool shared by only 4 units. At home, use your interior elevator to take you to all four floors. The oversized garage comes with a new garage door, a mini-split AC unit and plenty of room for your golf cart and beach toys. The first floor of living space has an open-plan kitchen with stainless steel appliances, a dining area and living room. There is also a balcony, laundry and half-bath on this floor. The next floor contains 3 spacious bedrooms and 2 baths. The Primary bedroom has an en-suite with dual sinks, both a garden tub and shower, and two walk-in closets. The top level had a surprise flex space that opens to the large roof top terrace with stunning views of the gulf. The flex space currently has 2 twin beds, a wet bar with under-counter sink, and a full bath with shower. Your home has a 2026 Roof, 2-AC units (2025 and 2022), and new Garage Door (2025). The property is currently being utilized as a WEEKLY rental and sleeps 8. The community is pet-friendly (owners only). Seller is grossing $100k using VRBO. Projections of $167,000+ with property manager. Come visit paradise on Siesta Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
1624 STICKNEY POINT RD #206, SARASOTA, FL 34231
$369,9001 Day 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
Taxes:$3,939
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)
1794 CUNLIFF LN, SARASOTA, FL 34239
$3,095,00052 Days on yellowkey MLS ID: A4685523
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)
757 BEACH RD #308, SARASOTA, FL 34242
$549,00031 Days on yellowkey MLS ID: TB8492005
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $46,500 (7.8%) on 04/23/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1970 Tax: $5,582 (2025)Community: Crescent RoyaleCondo
Taxes:$5,582
Remarks: Prime location directly across the street from Siesta Key Public beach has a full Gulf view that enjoys gorgeous sunrises and sunsets! Unit was completely gutted and remodeled with high end finishes, paint, and furniture in 2011. Everything is in excellent condition. This third floor unit in the highly desired Crescent Royale Condominium complex has a screened lanai, assigned covered parking space and storage locker for beach gear. Complex has large heated pool, grills with picnic area, bike parking, shuffleboard, a Clubhouse with pool table, exercise room and bathrooms. One mile to the Village restaurants and shops. This unit is sold turnkey furnished and allows weekly rentals. Use excellent on-site management or DIY on VRBO and AirBNB. Start your revenue stream from day one - ask to see our stunning rental history! Great income producer - $48,622 in 2025
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
1850 WEBBER ST, SARASOTA, FL 34239
$3,890,00034 Days on yellowkey MLS ID: A4686673
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026 Tax: $18,011 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$18,011
Remarks: One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
4689 OAK FOREST DR E #1, SARASOTA, FL 34231
$315,00058 Days on yellowkey MLS ID: A4684507
REDUCED by $15,000 (4.5%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 1984Monthly Fee: $633 Tax: $3,825 (2025)Community: Oak Forest VillasSpa: NoVilla
Taxes:$3,825
Remarks: Opportunity meets lifestyle in this beautifully maintained, furnished 3 bedroom, 2 bathroom end-unit home with a 2-car garage, situated in one of Sarasota’s most desirable communities. Move-in ready and designed for low-maintenance living, this light-filled residence offers outstanding flexibility as a primary residence, seasonal retreat, or income-producing investment property. Available furnished for immediate enjoyment, with the option to purchase unfurnished to reflect your personal style. Step inside to an inviting open-concept floor plan featuring high ceilings, wood-grain laminate flooring, abundant natural light, and expansive living and dining areas perfect for both entertaining and everyday comfort. The well-appointed kitchen boasts ample cabinetry, stainless steel appliances, generous counter space, and a versatile flex space just off the kitchen, ideal for casual dining, a home office, or bonus area tailored to your lifestyle. The spacious primary suite is a true retreat, complete with a large walk-in closet and an en-suite bath featuring a luxurious walk-in shower. Two additional bedrooms sharing a guest bathroom allow space for overnight guests, at-home office, studio or gym. Just off the back, you’ll find a fully screened lanai overlooking lush greenery, creating a peaceful private oasis, perfect for morning coffee and birdwatching or evening gatherings, with plenty of space for grilling and dining under the stars. Located nearby the clubhouse, this maintenance-free, pet-friendly community offers resort-style amenities including a heated pool and tennis courts, enhancing the relaxed Florida lifestyle. Positioned in a prime Sarasota location, you’ll be just minutes from the world-famous Siesta Key Beach, along with top-rated schools, shopping, dining, golf courses, and entertainment. Schedule your private showing today, this rare opportunity won’t last!
Listing Agent: Joey Lamielle (941-350-0016)
1731 SIESTA DR, SARASOTA, FL 34239
$2,595,0007 Days on yellowkey MLS ID: TB8500166
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3200 Built: 2026 Tax: $3,515 (2025)Community: BayviewSpa: YesSingle Family
Taxes:$3,515
Remarks: Under Construction. Brand new construction with ultra-luxury finishes, estimated for completion July 2026. This is the one. A statement home in one of Sarasota’s most desirable “West of the Trail” locations, designed with intention, elevated finishes, and a level of detail you simply don’t see every day. Be the first to live in it! Featuring 3 bedrooms, 2.5 bathrooms, plus a separate detached 1 bed, 1 bath guest house/in-law suite, this property offers flexibility, privacy, and true lifestyle living. From the moment you walk in, you’re welcomed by a stunning foyer featuring Taj Mahal quartzite and custom solid wood cabinetry, setting the tone throughout. Wide-plank oak flooring runs throughout the home, complemented by designer lighting, double recessed lighting, and curated finishes at every turn. The kitchen is a true showpiece—featuring Taj Mahal quartzite countertops, custom oak cabinetry in a soft cashmere tone, LED strip lighting, 3’ floating shelves with integrated lighting, a statement hood, oven and cooktop, refrigerator, built-in microwave island, spice rack, and a corner cabinet with a built-in lazy Susan. The island showcases sleek slat panel detailing, and the wine feature will be upgraded to a waterfall design. The living space is equally impressive, anchored by a Dimplex deluxe built-in electric fireplace with logs, framed by a custom American walnut wall unit, travertine stone, and metal detailing. The primary suite is a true retreat, featuring custom sand-grey paneling with integrated LED lighting, floating solid wood shelving with drawers, and a fully built-out walk-in closet with oak cabinetry and LED lighting. The spa-inspired primary bath showcases Taj Mahal quartzite countertops, a floating vanity with dual sinks, brushed gold fixtures, and a walk-in shower with dual shower heads including a rainfall feature. Step outside and it only gets better. The backyard is designed for true resort-style living, featuring a full infinity-edge pool with integrated jacuzzi, a fully equipped outdoor kitchen with BBQ and gazebo, perfect for entertaining. Take it to the next level—literally—with a rooftop terrace complete with a built-in bar with mini-fridge and private mini golf course, offering the perfect setting to enjoy sunsets and sweeping views of the beach and Sarasota skyline. Additional highlights include custom oak built-ins with LED lighting in the garage, designer light fixtures and wall sconces throughout, brushed gold plumbing and bathroom fixtures, Bosch appliances, Avanti wine fridge, and Samsung Bespoke washer & dryer. NO HOA. The location is unmatched!! 10 minutes to Siesta Key Beach, rated #1 beach in the US by US News, known for its white-quartz sand and turquoise water, and minutes to Turtle Beach. Just 5 minutes to Southside Village, a charming, walkable area with coffee shops, wine bars, and boutique dining, and 6 minutes to The Crossings at Siesta Key and Morton’s Gourmet Market. Downtown Sarasota is 10 minutes away, while St. Armands Circle and Lido Key Beach are approximately 15 minutes away. Sarasota Memorial Hospital is also just 5 minutes away. This home delivers the perfect balance of luxury, design, and lifestyle, complete with a private guest residence and resort-style outdoor living, making it an exceptional opportunity you don’t want to miss. All photos are renderings and virtually staged.
Listing is courtesy of: AIM WEALTH REALTY LLC (305-762-9576)
Listing Agent: Lyndsey Kaplan (813-924-4017)
8635 MIDNIGHT PASS RD #201C, SARASOTA, FL 34242
$599,99929 Days on yellowkey MLS ID: A4688472
REDUCED by $25,000 (4.0%) on 04/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1970 Tax: $5,913 (2025)Community: Bay Tree ClubCondo
Taxes:$5,913
Remarks: PRICE REDUCTION! This beautifully FULLY FURNISHED END-UNIT condo is a true gem, offering an abundance of natural light and a spacious, open layout. Featuring 2 bedrooms and 2 bathrooms, this home effortlessly blends comfort and style, making it the perfect space for both relaxation and entertaining. Step outside onto your private lanai and take in breathtaking views of serene Intracoastal waters—an ideal spot to unwind and embrace the peaceful surroundings. The primary bedroom features a walk-in closet and an en-suite bathroom for added convenience and comfort. The second bedroom is spacious, perfect for guests or family members alike. The kitchen boasts beautiful granite countertops, stainless steel appliances, and shaker cabinets with soft-close features, creating a sleek and functional cooking space. Located within a Gulf to Bay Community, this second-floor condo is just steps away from the pristine beach, which includes its own assigned storage cabana to stow your beach essentials, bikes, umbrellas, and chairs. Bay Tree community offers two heated pools, BBQ areas, kayak storage and fishing pier. For boating enthusiasts, the available boat slips provide easy access to the newly reopened Midnight Pass for all your water adventures. Fully furnished and with a STRONG rental history, this condo serves as an excellent income property—making it a fantastic choice for both vacation home seekers and investors alike. Equipped with HURRICANE IMPACT WINDOWS for added peace of mind and energy efficiency, this condo offers durability while maintaining a quiet, comfortable living environment. Additionally, the completed milestone inspection ensures transparency and confidence for the next homeowner. The monthly fees also cover a variety of essential services, including common area insurance, common area flood insurance, and an annual AC inspection and onsite Property Manager. Conveniently located near the free trolley stop, you’ll have easy access to explore Siesta Village’s restaurants, shops, and the world famous Siesta Key Beach with its white quartz sand. Don’t miss your chance to own a piece of paradise in one of Siesta Key’s most desirable locations. Whether you're seeking a vacation retreat, an investment property, or a coastal haven, this condo has it all! Schedule your showing today!
Listing Agent: Justin Piccillo (908-670-3209)
3234 RESTFUL LN, SARASOTA, FL 34231
$399,000287 Days on yellowkey MLS ID: A4658946
0 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1985 Built: 1957 Tax: $3,115 (2024)Community: Restful PinesSingle Family
Taxes:$3,115
Remarks: Under contract-accepting backup offers. NEW PRICE! MOTIVATED SELLER! Welcome to this beautifully remodeled 4-bedroom, 3-bath home located in the desirable Restful Pines neighborhood in South Sarasota’s 34231 zip code. Offering nearly 2,000 square feet of modern living space, this home features two spacious living areas, generously sized bedrooms, and a flexible layout perfect for families or entertaining. Enjoy peace of mind with a brand-new roof and air conditioning system, both installed in 2024. The home has been upgraded throughout with new windows and stylish modern doors that enhance both energy efficiency and curb appeal. The kitchen shines with sleek quartz countertops, stainless steel appliances, and a contemporary design that flows seamlessly into the main living spaces. All three bathrooms have been beautifully updated with new vanities, glass-enclosed showers, and modern tile finishes. Set on a quarter-acre lot in Flood Zone X, this home has never flooded and offers a large backyard with plenty of room to add a pool, detached garage, or storage building. Best of all, there are no HOA or CDD fees, giving you the freedom to enjoy your property without added restrictions or costs. Enjoy the convenience of walking to A+ rated Riverview High School and nearby Red Bug Slough Preserve with scenic trails and nature views. You're also just minutes from Siesta Key’s world-famous beaches, Detwiler’s Farm Market, and the vibrant Gulf Gate dining and shopping district. With a motivated seller, this move-in ready home is a fantastic opportunity in one of Sarasota’s most convenient and sought-after locations!
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
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