Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3118 KEY WAY, SARASOTA, FL 34239
$599,00040 Days on yellowkey MLS ID: A4685119
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 1961 Tax: $2,942 (2025)Community: SouthgateSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,942
Elementary School: Wilkinson Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Beautifully updated 4-bedroom, 2-bath pool home in the desirable Southgate neighborhood of Sarasota offering the ideal blend of indoor comfort and outdoor Florida living. The home features a bright open layout with expansive pocket sliding glass doors that fully open to an oversized open-air pool and patio, perfect for entertaining and relaxing. The updated kitchen includes extensive custom cabinetry with built-in pantry storage and a discreetly integrated laundry area. The home offers four spacious bedrooms and two bathrooms, including a guest bath with a soaking tub. Outside, the property features a large additional paved parking pad along with the driveway and garage, providing ample space for multiple vehicles and recreational equipment. With minimal deed restrictions, the property allows RV and boat parking, with additional space along the side of the home. The backyard also includes a custom playground area. Conveniently located just minutes from Siesta Key Beach, downtown Sarasota, shopping, dining, and parks.
Listing is courtesy of: PREMIER AGENT NETWORK (877-663-9366)
Listing Agent: Stephanie Hawkins (941-587-4337)
6836 ROXBURY DR, SARASOTA, FL 34231
$575,0008 Days on yellowkey MLS ID: A4686601
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1530 Built: 1969 Tax: $5,635 (2025)Community: Gulf GateSingle Family
Taxes:$5,635
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: A fantastic opportunity to own a home in the highly desirable Gulf Gate community. This property also offers 1% lender credit at closing. Featuring 2 bedrooms, 2 bathrooms, and a spacious one-car garage with a circular driveway, this home provides both comfort and convenience. The interior showcases an open-concept living and dining area with tile flooring throughout, creating a bright and inviting space. The kitchen has been updated with granite countertops, and both bedrooms include walk-in closets for ample storage. A versatile bonus room offers flexibility as a home office or potential third bedroom. Upgrades include a 2021 roof, updated ductwork, improved underground plumbing, a new AC system installed in 2024, and an upgraded main electrical panel to a new 200-amp panel in 2024. The property also features a newly installed sprinkler system covering the entire landscape, along with landscape lighting with a timer in the backyard, both added in 2024. Step outside to enjoy the fully renovated saltwater heated pool and screened lanai—perfect for relaxing or entertaining. Ideally located just minutes from Siesta Beach, the Legacy Trail, shopping, dining, and the neighborhood library, this home is surrounded by everyday conveniences. Gulf Gate also features sidewalks, streetlights, and is within walking distance to top-rated Gulf Gate Elementary School.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
539 AVENIDA DEL NORTE, SARASOTA, FL 34242
$5,499,00085 Days on yellowkey MLS ID: A4679096
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4195 Built: 2026 Tax: $7,935 (2025)Community: Archibald ResubSpa: YesSingle Family
Taxes:$7,935
Elementary School: Phillippi Shores Elementary
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. EXQUISITE NEW CONSTRUCTION ON SIESTA KEY: ISLAND LUXURY REDEFINED | Estimated to be substantially completed by 4/30/2026 | A rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. | SIESTA Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. | MOMENTS from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity, your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock, a true island luxury. | THIS thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate craftsmanship and fine detail, the home offers 4,195 sq ft of interior living space and an additional 3,756 sq ft of outdoor living, seamlessly blending indoor and outdoor environments. | THE chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. | TWO bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or elevator one level up to access the private primary suite featuring a truly custom bath with bespoke tile, finishes, soaking tub and spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper-level.| FLEXIBLE, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any family’s lifestyle from multi-generational living to a dynamic entertainer’s paradise. | IMAGINE a home where the luxuries of island beach life blend with a private, resort-style retreat: *Inground pool & spa for cooling off or casual lounging*Rooftop deck for sunset cocktails and starlit conversation*Private boating access just steps from your front door. | AND, when you’re ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. |THIS is more than a home, it’s an invitation to own your piece of the new Siesta Key lifestyle: elevated, effortless, and extraordinary.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Otte (941-281-5472)
5619 NEW YORK AVE, SARASOTA, FL 34231
$399,000188 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
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)
3230 VILLAGE GREEN DR #1032, SARASOTA, FL 34239
$195,00054 Days on yellowkey MLS ID: A4683197
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1419 Built: 1971 Tax: $3,030 (2025)Community: South Gate Village Green 10Condo
Taxes:$3,030
Remarks: Welcome to a classic Florida home that perfectly blends comfort, style, and functionality. With its solid construction and timeless character, the home blends classic design with the potential for modern updates, making it perfect for buyers looking to personalize their space. Spacious living areas, abundant natural light, and a functional layout create an inviting atmosphere ideal for both relaxing and entertaining. The open-concept layout creates a seamless flow between the kitchen, dining, and living areas, making it all the more inviting. Village Green is a 55+ community that has a ton of amenities. Right on the other side of the neighborhood is even an executive golf course that can meet all your golfing needs.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: James Graves (678-817-8166)
1661 S JEFFERSON AVE, SARASOTA, FL 34239
$1,250,00041 Days on yellowkey MLS ID: A4684656
0 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2490 Built: 1953 Tax: $12,131 (2025)Community: Alfred ParkSpa: YesSingle Family
Taxes:$12,131
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Live where mornings begin with coffee on the wide front porch beneath mature live oaks and evenings end with a swim in your own heated pool and spa, added by the current owner to elevate Florida living. Completely renovated down to the studs in 2021, this move-in-ready, three-bedroom, three-bath Arlington Park pool home with dedicated office, den/sunroom and bonus room blends timeless mid-century charm with modern systems and design. Major upgrades include a 2021 metal roof, newer plumbing, newer electrical wiring and panel, hurricane-rated windows, hurricane-rated garage door, LED lighting and hand-scraped engineered hardwood floors throughout, delivering both beauty and long-term peace of mind. Walls were thoughtfully opened to create bright, flowing living spaces anchored by a stunning Quartzite kitchen featuring an oversized island with seating, solid wood soft-close cabinetry, stainless KitchenAid appliances including under-counter microwave, full-height subway tile backsplash, ample pantry storage, and a built-in Quartzite-topped buffet with glass-front cabinetry and wine refrigerator in the dining area. The spacious living room and adjoining den/sunroom connect seamlessly to the private, fully fenced backyard oasis with multiple seating areas and professional landscaping. The owner’s suite offers a peaceful retreat with spa-style bath, Quartzite counters, glass-enclosed shower and private outdoor lounging deck, while two generously sized guest bedrooms, one ensuite, and two additional fully reimagined baths provide comfort and flexibility. A custom office with Quartzite and wood built-ins supports work-from-home ease, and the large bonus room is ideal for a gym, media room, or play space. Perfectly positioned on a prominent corner lot with circular driveway and side-entry two-car garage, this home is a short distance from Arlington Park and Aquatic Complex featuring a 50-meter lap pool, fitness center, indoor gymnasium, tennis and pickleball courts, basketball courts, playground, dog park and scenic walking trails, and is minutes to Downtown Sarasota’s restaurants, arts and waterfront, Southside Village shopping and dining, Sarasota Memorial Hospital and the world-famous beaches of Siesta Key. For buyers searching for a fully renovated Arlington Park pool home in Sarasota with modern upgrades, walkability and unbeatable proximity to parks, downtown and beaches, look no further.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Roberta Tengerdy, Pa (941-321-2292)
7214 CLOISTER DR #7214, SARASOTA, FL 34231
$230,000292 Days on yellowkey MLS ID: A4656943
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1983 Tax: $1,963 (2024)Community: Lakeside Club Of SarasotaCondo
Taxes:$1,963
Tax Year: 2024
Remarks: Lakeside Club of Sarasota, move-in ready! This spacious second-floor two-bedroom, two-bath condominium features vaulted ceilings and a large screened lanai overlooking a serene lagoon and preserve. The open-concept living and dining area flows seamlessly to the private outdoor spaces, creating an environment for relaxation and entertaining. Enjoy your morning coffee on the front patio and unwind in the fully enclosed back lanai with tranquil pond views and a manicured green lawn just beyond. Ideally in the desirable Gulf Gate area, just 12 minutes from the nation’s No. 1 beach, Siesta Key, this well-maintained home offers a blend of comfort and convenience. Recent updates include a new roof and skylights (2025), PGT hurricane windows on the east side, a new air conditioner with heat pump and water heater (2023), and a refrigerator replaced in 2025. The stackable washer/dryer and range are only five years old. Community amenities include tennis courts, a clubhouse, a refreshing pool and covered carport parking. You'll love the proximity to the new Gulf Gate Library, popular restaurants, shopping and everything Sarasota has to offer. Whether you're looking for a full-time residence or a winter retreat, this condominium is must-see. Schedule a showing today.
Listing Agent: Cindy Taliaferro (941-894-7269)
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,349,00049 Days on yellowkey MLS ID: A4683108
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $10,806 (2025)Community: Gulf & Bay ClubCondo
Taxes:$10,806
Remarks: Welcome to the effortless rhythm of island living at Gulf & Bay Club, one of Siesta Key’s most prestigious beachfront communities. Behind the 24-hour guard-gated entrance, this beautifully remodeled, rarely available, three-bedroom residence offers the perfect blend of comfort, privacy, and resort-style living in a setting that feels worlds away from the everyday. Positioned on the first floor as a bright end unit, the home is surrounded by windows on three sides, filling the interior with natural light and creating a relaxed coastal atmosphere throughout. The thoughtfully redesigned floor plan opens beautifully for entertaining, with elegant finishes and carefully curated upgrades that make the residence feel both sophisticated and welcoming. The kitchen was designed with gathering in mind, featuring custom cabinetry, quartz countertops, marble backsplash, and premium Bosch appliances including induction cooktop and stainless vent hood. An additional built-in entertaining area with beverage refrigeration and extra storage makes hosting friends and family effortless. Living and dining areas flow naturally to the private lanai overlooking tropical landscaping and a tranquil lagoon, just steps to one of the community’s three pools, where evenings are often spent enjoying the peaceful surroundings and the soft glow of Siesta Key sunsets. The three-bedroom layout provides exceptional flexibility, whether for hosting guests, accommodating family, or creating a quiet home office. The primary suite offers a peaceful retreat with a walk-in closet and a beautifully updated bath featuring custom cabinetry, quartz countertops, and an expanded designer-tiled shower. Extensive renovations throughout the home include raised ceilings, smooth-finish walls, luxury flooring, updated lighting and electrical systems, new ductwork, upgraded panel box, air handler, and quick-recovery water heater. Importantly, the residence did not experience water intrusion during the recent hurricanes, offering additional peace of mind. Life at Gulf & Bay Club is defined by its resort-style amenities across 32 gated beachfront acres and 800 feet of Siesta Key’s famous quartz sand beach. Residents enjoy three heated pools including a lap pool, tennis and pickleball courts, racquetball, a large fitness center, beautifully landscaped walking paths surrounding the freshwater lagoon, clubhouses for gatherings, electric vehicle charging stations, and professional on-site management — all within a secure 24-hour guard-gated community. Just beyond the gates, the vibrant charm of Siesta Key Village awaits with its locally loved restaurants, boutiques, and island nightlife, while downtown Sarasota’s renowned arts and cultural scene is only a short drive away. This is more than a residence — it is an opportunity to experience the best of beachfront living on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
2625 COLONY TER, SARASOTA, FL 34239
$2,650,00026 Days on yellowkey MLS ID: A4686022
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3634 Built: 2007 Tax: $16,973 (2025)Community: Bay View Heights AddSpa: YesSingle Family
Taxes:$16,973
Elementary School: Southside Elementary
Remarks: Upon entering this impeccably crafted residence, you are immediately greeted by a refined level of finish and thoughtful design. Rich hardwood flooring flows seamlessly throughout the main living areas, complemented by intricate custom millwork, elegant moldings, and double tray ceilings that enhance the home’s architectural character. Designed with intention, this 4-bedroom, 4-bath residence—featuring two bedrooms currently utilized as a den and one as a sitting room—along with a versatile bonus room ideal as a fifth bedroom, office, or private gym, offers effortless single-level living with an exceptional sense of space and functionality. As you enter, a formal sitting area anchored by a detailed fireplace creates an inviting first impression, complemented by an adjacent dedicated dining room and an elegant wet bar—perfect for entertaining. The kitchen is a true statement of both style and function, featuring artisan granite, two expansive islands offering generous space for cooking, gathering, casual seating, and designer backsplash detailing. A full suite of top-tier stainless steel appliances, including dual Liebherr refrigerators, an induction cooktop, and a built-in oven and microwave, is seamlessly integrated. Reverse osmosis filtration at the sink, along with a whole-house water filtration system, enhances everyday living. The spacious family room is designed for comfort, offering expansive views of the pool and lush Florida-native landscape, creating a seamless indoor-outdoor living experience. The primary suite is a luxurious private retreat, offering direct access to the pool, three spacious walk-in closets, and a spa-inspired bath adorned with exquisite custom stone finishes. The primary bathroom is thoughtfully designed with two separate vanities and generous counter space. Meticulously maintained and extensively upgraded, the home offers a level of efficiency and ease. Recent improvements include a new roof (2023), two new Lennox air conditioning systems (2023–2024), Storm Smart hurricane shutters, and hurricane-rated garage doors. A whole-home generator and multiple propane tanks provide added peace of mind, while energy-efficient heat pump systems service the pool heater, water heater, and HVAC. Outdoor living is equally impressive, with a beautifully updated pool area featuring a fully refurbished enclosure, upgraded automation system, and pool heater. An Artisan infrared grill connected to a permanent propane source creates an ideal, relaxed setting for entertaining, surrounded by Florida-friendly native landscaping and ambient landscape lighting. Additional enhancements include a drip irrigation system with a separate meter, an upgraded security system with cameras, and UniFi Wi-Fi extenders for seamless connectivity throughout the home. The three-car garage is as functional as it is polished, featuring an epoxy-coated floor, built-in cabinetry, and overhead gantry storage systems. Throughout the home, you’ll find abundant storage space with custom-built-in cabinetry thoughtfully integrated for easy everyday living. Ideally situated in the highly coveted West of Trail enclave of Bayview Heights, this custom-built home offers an exceptional lifestyle. Located on a rare dead-end street just one block from the bay, and within minutes of downtown Sarasota, Southside Village, and the area’s renowned beaches, it also lies within top-rated school districts—an unparalleled combination of privacy, convenience, and prestige.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
7145 BRIGHT CREEK DR #33, SARASOTA, FL 34231
$240,0008 Days on yellowkey MLS ID: A4689181
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1352 Built: 1981Monthly Fee: $325 Tax: $3,031 (2025)Community: Woodside South Ph 1 2 & 3Villa
Taxes:$3,031
Remarks: This charming 2-bedroom, 2-bath plus bonus room villa is nestled in the quiet and desirable Woodside South community in the Gulf Gate area of Sarasota. Ideally located just minutes from world-renowned Siesta Key Beach, with easy access to Interstate 75, and surrounded by a variety of restaurants, shopping, and premier golf courses, this home offers both convenience and a relaxed Florida lifestyle. The low maintenance fee includes water, trash, basic cable, pest control, exterior maintenance, and landscaping—making for truly easy living. This villa boasts larger square footage than many others in the community and features a spacious, light-filled living room, a kitchen with a cozy eating area, a primary suite with a full bath and walk-in closet, a second bedroom, and an additional full bathroom. A versatile den/office with a private exterior entrance adds extra flexibility for work or guests. Enjoy tile flooring throughout for a clean, modern feel. Residents also have access to a community pool and clubhouse—perfect for relaxing and socializing. Tenant's lease ends 4/30/2026.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kate Aumua (305-542-5452)
2214 MICHELE DR, SARASOTA, FL 34231
$724,90034 Days on yellowkey MLS ID: A4686063
Bed: 4 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1977 Tax: $6,622 (2025)Community: Phillippi GardensApartment
Taxes:$6,622
Remarks: Great investment opportunity with strong income potential! This well-maintained duplex features two spacious units, each offering 2 bedrooms, 2 bathrooms, and a single-car garage, each on its own water and electric meter. One unit is being sold fully furnished and is ready for immediate rental, making it easy to start generating income right away. Both units have been remodeled and offer comfortable, inviting living spaces. The flexible layout makes this property ideal for a variety of investment strategies. Live in one unit while renting the other, lease both units for maximum income, or create the perfect multi-generational living setup. The choice is yours! Recent updates provide added peace of mind, including a roof installed in 2022 and updated AC units installed in 2022 and 2024. The property also weathered the recent storms with no damage, further highlighting its durability and care. Located just minutes from world-renowned beaches, including Siesta Key Beach, this property offers easy access to golf courses, shopping, dining, and the vibrant arts and cultural scene of Sarasota. Whether you're expanding your investment portfolio or searching for a property with income-producing potential and lifestyle appeal, this duplex presents a rare opportunity in a highly desirable location. Come see, come sigh and make this property your own!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
4557 WORCESTER RD, SARASOTA, FL 34231
$479,000109 Days on yellowkey MLS ID: A4675974
REDUCED by $20,000 (4.0%) on 04/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1423 Built: 1998 Tax: $4,659 (2025)Community: Flora-VillaSingle Family
Taxes:$4,659
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. And for those who want a little extra charm, the chicken coop is negotiable.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
3441 GULFMEAD DR, SARASOTA, FL 34242
$10,500,00016 Days on yellowkey MLS ID: A4684918
Bed: 6 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 4769 Built: 2026 Tax: $16,553 (2025)Community: Gulfmead EstatesSingle Family
Taxes:$16,553
Remarks: Pre-Construction. To be built. This luxurious grand canal-front estate offers direct deep-water boating to the Gulf, out of one of the most exclusive neighborhoods on north Siesta Key. This in progress New Construction property by Pham Development is on an expansive 17,842 SF and 0.41 acre lot, with a 4,769 SF traditional-style home to be built. Enjoy two separate guests suites on top of the two 2-car garages, for a total of 4 garage spaces, both with elevator access to the above suites. The master bedroom will have water views, and the grand entry home hosts a total of 6 bedrooms, 6 baths, and 1 powder bath. This property's deep-water grand canal with no bridges is ideal for yachts and boats, with up to a 13-foot draft. A new dock and boat lift is set to be installed. Inside, expansive living spaces boast high-end finishes and top-of-the-line appliances, blending timeless elegance with modern comfort. Enjoy the water, and a large backyard perfect for entertaining, a private pool, and new lush landscaping—making this the ultimate waterfront estate for family.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
5408 EAGLES POINT CIR #102, SARASOTA, FL 34231
$559,900183 Days on yellowkey MLS ID: A4668010
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1768 Built: 1990Monthly Fee: $167 Tax: $5,416 (2024)Community: Bayview Homes ICondo
Taxes:$5,416
Remarks: Just Move In... Beautifully updated condo with amazing Views located just a minutes From Siesta Key Beach and Downtown Sarasota. Totally remodeled condo with Impact Hurricane windows and doors, all new kitchen featuring solid wood Cabinets, granite countertops and backsplash, with center island and Stainless steel appliances . Large Master suite with his and her walk-in closets ensuite master bathroom with dual sinks and massive walk-in shower. All new luxury Vinyl and porcelain flooring throughout the unit. New Hvac system 2022, Private Laundry room, Open floor plan with massive living room and dining are overlooking lake and water fountain. Private under building covered parking. The Landing is a well Maintained active community with 24 hour guard gated West of the trail featuring acres of Lush Landscaping , nature trail leading to gazebo overlooking the Intercostal waterway , fishing pier and Kayak launch. Your purchase includes membership to the Landings Racquet Club with Olympic -sized heated pool, Hot tub , Eight Har-tru tennis courts, Fitness center , Library with kitchen and on site tennis Pro shop. Seller will consider selling the condominium fully furnished on a separate sale bill. A Great Place To call Home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Gary Hoskins (941-809-7709)
1400 SIESTA DR, SARASOTA, FL 34239
$4,500,00050 Days on yellowkey MLS ID: A4678496
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 4660 Built: 1978 Tax: $22,924 (2025)Community: Acreage & UnrecSpa: YesSingle Family
Taxes:$22,924
Remarks: Welcome to 1400 Siesta Drive, where refined waterfront living becomes your everyday reality. This home is quietly tucked away behind a gated entrance, with an additional secondary gate providing exclusive access to the residence. Thoughtfully designed to embrace breathtaking, unobstructed views of Sarasota Bay, this modern residence is a showcase of light, space, and coastal elegance. Expansive floor-to-ceiling windows frame the ever-changing scenery, offering front-row views of passing boats and unforgettable sunsets from nearly every room. The primary suite is a private sanctuary, featuring a generous walk-in closet, a spa-inspired ensuite bath, and a dedicated office—each enhanced by stunning bay views. Outdoors, your personal oasis awaits with a heated pool, abundant sun-drenched lounging space, and a newly constructed dock ready for effortless boating and waterfront adventures. Ideally located near Sarasota’s world-class dining, shopping, and cultural attractions, this exceptional bayfront retreat offers the perfect balance of privacy and convenience. Offered turn-key furnished, this is a rare opportunity to step seamlessly into an elevated waterfront lifestyle.
Listing Agent: Matthew Voss (941-402-8799)
5966 MIDNIGHT PASS RD #G118, SARASOTA, FL 34242
$1,150,000134 Days on yellowkey MLS ID: A4671884
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 864 Built: 1970 Tax: $9,506 (2024)Community: Palm Bay Club ICondo
Taxes:$9,506
Remarks: Under contract-accepting backup offers. Experience breathtaking, panoramic Gulf of Mexico views from this one of a kind penthouse-level residence. Located in the coveted Gulf-Front Tower at the Palm Bay Club on Siesta Key! Sitting high above the shoreline, you'll have the opportunity to experience amazing Siesta Key Sunsets like never before! This rare opportunity features a bright, open layout with a welcoming foyer, crown molding, and tile flooring throughout. The spacious kitchen includes granite countertops, trey ceiling detail, breakfast-bar seating, and a direct backdrop of the shimmering Gulf. The utility room adds valuable convenience and storage. Resort-style amenities include private deeded beach access, beach chairs, two heated pools (including one beachside), a large hot tub, barbecue areas, bayside fishing pier, lighted tennis & pickleball courts, fitness center, complimentary WiFi, 24-hour security and more. With excellent rental potential and a 3-day minimum rental program, this residence is ideal as a high-performing investment, seasonal escape, or full-time coastal retreat. Offering the best of both worlds with flexibility to make a nice income while still enjoying it personally. The onsite rental management provides an effortless, hands-off experience. Enjoy the island lifestyle just minutes from Siesta Key Village’s boutiques and restaurants, and a short drive to Downtown Sarasota’s vibrant arts and dining scene.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Ryan Miller (941-954-6925)
5830 MIDNIGHT PASS RD #705, SARASOTA, FL 34242
$1,240,000135 Days on yellowkey MLS ID: TB8451655
0 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1285 Built: 1976 Tax: $10,763 (2024)Community: Jamaica Royale Tower IiSpa: NoCondo
Taxes:$10,763
Remarks: Under contract-accepting backup offers. Welcome to your beachfront oasis! NEXT AVAILABLE TO SHOW APRIL 4th between 10:00 and 2:00. VIDEO WALK THROUGH AVAILABLE UPON REQUEST. Discover your perfect getaway in this beautifully refreshed 7th-floor condo, offering stunning balcony views of the Gulf of Mexico. With 1,285 square feet of living space, this fully furnished property features 2 bedrooms and 2 full bathrooms—all you need to bring is your bathing suit and toothbrush! The light-filled great room seamlessly connects the kitchen, living area, and dining space, making it ideal for relaxation and entertaining. Recent upgrades include new HVAC (3/2026), elegant touches like solid surface countertops, a stylish backsplash, and pendant lighting in the kitchen, along with a freshly painted interior and new lighted ceiling fans, The primary bathroom boasts a new solid surface vanity, a backlit mirror, a glass shower door, and designer tiled flooring, just to name a few. After a day at the beach, take a refreshing dip in the pool or unwind on your spacious balcony while watching the sunset. With an onsite management team, your beach retreat promises to be both profitable and hassle-free. This condo has a robust rental history, making it a fantastic investment opportunity for vacation rentals. Residents and guests of Jamaica Royal benefit from deeded assigned parking and access to private beach chairs. Located in a prime area, you can easily explore local restaurants and enjoy live music, all just a trolley or bike ride away. Don’t miss your chance to own this incredible piece of paradise!
Listing is courtesy of: PLUMLEE GULF BEACH REALTY (727-595-7586)
Listing Agent: Beverly Schroeder (727-422-5779)
2421 PROSPECT ST, SARASOTA, FL 34239
$649,00086 Days on yellowkey MLS ID: A4677367
REDUCED by $49,500 (7.1%) on 04/07/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 972 Built: 1956 Tax: $4,592 (2025)Community: Arlington ParkSingle Family
Taxes:$4,592
Remarks: Now Offered at a Rare Value...Welcome to 2421 Prospect Street in Arlington Park’s Tightly Held RUSTIC LODGE…This Elegantly Refined Florida Mid-Century Retreat with Modern Coastal Finishes is Rooted in Sarasota’s Golden Era…the 1950s Marked a Time When Homes Were Designed & Built with Longevity & Craftsmanship—2421 is a Beautiful Reflection of That Legacy…Approached Not as a Renovation but as a Custom Crafted Rebuild...A Design-Conscious Builder Honored the Original Vision While Elevating the Residence to Meet Today’s Expectations for Style, Comfort, and Quality…the Integrity, Proportions, and Character Remain Intact, Now Enhanced by Refined Finishes, Seamlessly Integrated Contemporary Systems, Forward-Thinking Infrastructure, and Improvements Aligned with City of Sarasota Code…Sleek, Clean & Effortlessly Cool—As Though the 1950s Walked Into 2026 with Style…Expansive New PGT Impact Windows, Sliders & Doors Bathe the Home in Light While Preserving Tranquility…Every Detail Has Been Carefully Considered, Including All New Plumbing with Cast Iron Replacement Under the Slab, All New Electrical, HVAC Ductwork, and Engineered Structural Enhancements to Create an Open Floorplan...Insulated Interior Walls in Key Areas, Blown Attic Insulation, Tankless Water Heater, Fresh Paint, White Oak Style Plank Flooring with Four-Inch Baseboards, Frameless Glass Shower Doors, Custom Walk-In Closets, and Soft-Close Cabinetry Throughout…Curated Quartz Countertops Extend Across the Gourmet Chef’s Kitchen, Catering Pantry, Dry Bar, and Bathrooms…Recently Enhanced with a Brand-New Stainless Steel LG Dishwasher & New GE Profile Refrigerator…Additional Home Features Include Glass Tile Backsplashes, Substantial Kitchen Island with Tile Accent Lighting, and Vented Range Hood…Discreetly Integrated Throughout is a Fully Automated Smart Home System Offering Complete Flexibility—Including Remote Entry Keypads, Wireless Alarm, Ring Cameras, Motion Detectors, Panic Buttons, Remote-Control Ceiling Fans, USB & USB-C Outlets, Nest Thermostat, and Digitally Controlled Irrigation—Allowing the Home to Be Fully Automated or Enjoyed Traditionally at the Owner’s Preference…A Fully Screened Lanai with Custom Tongue & Groove Ceiling Extends the Living Space Outdoors, Complemented by New Epoxy Flooring Leading to the Paver Patio with Pool, Spa & Expansion Concepts Available…The Grounds Have Been Curated with a Six-Figure Landscape & Lighting Package, Fully Fenced, Double-Gated Privacy, Mature Junipers, Lush Clusia Hedges, Olive Trees, Bird of Paradise, and Fragrant Jasmine…A Three-Bedroom, One-and-a-Half-Bath Residence in the Heart & Soul of Arlington Park—Just Blocks to Legacy Trail and Arlington Park & Aquatic Center Hosting Live Music Events Alongside Pickleball, Tennis, Basketball Courts, Playgrounds, a Dog Park, Walking Trails, and Two Pools…Blocks to Sarasota Memorial Hospital, Minutes to Downtown Sarasota, Siesta Key, Longboat Key, Anna Maria Island, UTC Mall, and a Depth of Dining & Cultural Offerings Favored by Locals…Just a Fifteen-Minute Drive to Sarasota-Bradenton International Airport…Weekly Rentals Are Allowed, Not in a Flood Zone, No Storm Damage, No HOA, and Offered Turn-Key Furnished or Thoughtfully Curated to Buyer Preferences…Passed Down Through Only Two Owners Since the 1950s, This Home Represents Stewardship, Architectural Lineage, and Forward-Thinking Living…It’s Timeless, Intentional, and Unmistakably Rare…Schedule Your Private Tour Today & Live a Fuller Life!
Listing is courtesy of: FULLER GROUP (941-961-3100)
Listing Agent: Bo Fuller (941-961-3100)
4939 PEREGRINE POINT WAY, SARASOTA, FL 34231
$1,685,00077 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)
5430 EAGLES POINT CIR #104, SARASOTA, FL 34231
$400,00072 Days on yellowkey MLS ID: A4678523
REDUCED by $49,900 (11.1%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1608 Built: 1995Monthly Fee: $167 Tax: $2,733 (2025)Community: Eagles Point At The Landings 2Condo
Taxes:$2,733
Remarks: Under contract-accepting backup offers. GREAT PRICE CONDO AT THE LANDINGS, EAGLES POINT - COASTAL LIVING MEETS INCREDIBLE CONVENIENCE! Exceptional value and what a location! Welcome to this stunning property at Eagles Point, nestled within The Landings - Sarasota’s premier gated, waterfront community west of the Trail. This beautifully updated 2-bedroom, 2-bath residence with a versatile den offers the perfect blend of comfort, style, and lifestyle - perfect for full-time living or a refined coastal retreat. The den easily converts to a third bedroom, home office, or guest space to suit your needs. The newly remodeled kitchen showcases modern finishes, top-of-the-line appliances, a convenient in-unit washer and dryer, and a built-in desk or breakfast nook. NEW AC SYSTEM: 2025! Luxury vinyl plank flooring flows throughout the home, adding both elegance and durability. Step onto the screened lanai to enjoy peaceful views of a private extended terrace, protected mangroves, and spectacular Sarasota sunsets - ideal for morning coffee or evening relaxation. This residence includes secure under-building parking in a gated garage, along with private storage, bike racks, and space for kayaks and canoes. Eagles Point features secured lobby access and overlooks the Intracoastal Waterway, creating a serene and private setting surrounded by nature. Residents enjoy a nearby waterfront gazebo, perfect for watching boats and birds, as well as nature trails with kayak launch access. As a resident of The Landings, you’ll enjoy access to the Eagles Point pool and the sought-after Racquet Club, offering tennis, pickleball, a fitness center, library, meeting rooms, and a Junior Olympic–size pool - ideal for an active and social lifestyle. Centrally located in the heart of Sarasota, The Landings is just minutes from shopping, dining, downtown Sarasota, and the world-renowned Siesta Key beaches. Move-in ready with quick closing available and easy to show. No storm or flood issues. Don’t miss this unique opportunity to own an extraordinary condo in The Landings and experience the very best of Sarasota coastal living!
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Tracy Seider (941-356-2057)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.