Location: Saint Armands Div John Ringling Estates, Sarasota
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408 JACKSON DR, SARASOTA, FL 34236
$2,998,0004 Days on yellowkey MLS ID: A4687364
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2585 Built: 1955Monthly Fee: $4 Tax: $23,258 (2025)Community: Saint Armands Div John Ringling EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$23,258
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Better than new and upgraded to perfection! Steps from St. Armands Circle, this spacious and quiet 4BR/4BA home offers tranquility in its simplicity, while still walkable to a bevy of options for activities and entertainment. The fenced-in garden, pool, and covered outdoor eating area make this nearly new home a gem of all jewels. Walk to St Armands Circle in minutes, a short distance to Lido Beach, and Sarasota’s bustling downtown. Perfect for family living or entertaining on any scale. Nothing was overlooked when this home was meticulously renovated recently! Remarkable touches and style are visible in every room, from soaring tray ceilings and recessed lighting, to the seamless indoor/outdoor flow that’s created by a wall of double-paned sliders, and a shady poolside outdoor eating/grilling space. The open and light-filled Great Room effortlessly connects to a welcoming dining area and exquisite new chef’s kitchen, boasting waterfall quartz countertops and backsplash, as well as an extended breakfast bar, SS appliances, convenient pot-filler, and updated neutral sage-tone solid wood cabinets on display. The Casita with a separate (keyless) entryway would delight any overnight visitors! This private suite boasts its own mini-kitchen, bathroom, walk-in closet, and French doors leading guests directly into a hidden and relaxing pool area. Just 2 blocks to St. Armands Circle, minutes from the heart of downtown Sarasota and its Bayfront, where a sprawling cultural hub offers: theaters, Opera, museums, restaurants, boutique shopping, dining, and plenty of entertainment venues. Finally a place where you can relish in the peace and luxury of quiet comfort near St Armands Circle, while enjoying the best entertainment and activities that downtown Sarasota can share. Come see it for yourself!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
439 MADISON DR, SARASOTA, FL 34236
$5,900,000255 Days on yellowkey MLS ID: A4659293
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4036 Built: 2026 Tax: $21,020 (2024)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$21,020
Tax Year: 2024
Remarks: Under Construction. 439 Madison is emerging as a striking new statement in modern luxury a rare opportunity to secure a fully custom, architecturally refined residence while construction is underway, with time remaining to personalize and select finishes. Designed with intention and executed with uncompromising quality, this home blends clean, modern lines with warm, natural materials. The exterior is thoughtfully composed with sand-finished HardiPlank siding, impact-rated insulated windows, an 8-foot stained fiberglass entry door, tongue-and-groove wood ceilings, and professionally designed, fully irrigated landscaping that frames a paver-lined driveway and expansive lanai. At the heart of the home, indoor and outdoor living merge seamlessly. A private pool and spa with sunshelf and heater create a resort-style setting, ideal for entertaining or quiet retreat. Inside, wide-plank wood flooring flows through the living spaces, complemented by porcelain tile in all baths and custom-built closets throughout. The chef’s kitchen is both elevated and inviting — featuring custom cabinetry with dovetail joinery and soft-close doors, 42” uppers with under-cabinet LED lighting, quartz countertops, a farmhouse sink, bespoke tile backsplash, and a professional-grade stainless steel appliance suite. The owner’s suite is a sanctuary of calm, offering a spa-inspired bath with a frameless glass walk-in shower, rain and handheld shower heads, quartz-topped vanities, custom cabinetry, and designer tile extending to the ceiling in all wet areas. Each additional bath echoes this same level of thoughtful luxury. Built for performance as much as beauty, the home features a reinforced concrete slab foundation, spray-foam insulated roof deck, rigid block wall insulation, and true high-efficiency construction. Additional highlights include a fully appointed laundry room with custom cabinetry, quartz counters, and utility sink; dual insulated garage doors with openers; an epoxy-finished garage floor; and a 10-year structural warranty. 439 Madison is more than a home — it is a carefully crafted lifestyle offering sophistication, longevity, and effortless modern living. With construction underway and completion slated for 2026, this is a rare chance to shape a luxury residence tailored to your vision.
Listing is courtesy of: SARASOTA REALTY CENTER LLC (941-702-3635)
Listing Agent: Frank Golio Jr., Pllc (941-363-1075)
103 FILLMORE DR, SARASOTA, FL 34236
$2,499,00016 Days on yellowkey MLS ID: A4686381
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2908 Built: 1951 Tax: $20,246 (2025)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$20,246
Remarks: Welcome to 103 Fillmore Drive, a beautifully renovated 4-bedroom (or 3 bedroom plus den/office), 3-bath pool home located in the heart of world-famous St. Armands Circle. Just a few blocks from the white sands of Lido Beach, this exceptional property offers the perfect opportunity as a primary residence, vacation home, or income-producing investment. The home has been completely renovated and features an open, inviting layout designed for comfortable Florida living. The living area includes a cozy fireplace and flows seamlessly to the outdoor entertaining spaces. Step outside to your private backyard oasis with a sparkling pool, tropical landscaping, bar with grill,and a firepit lounge area—perfect for relaxing or entertaining under the Florida sunshine. Major improvements include a new roof installed in 2025, kitchen and baths updated and whole home beautifully remodeled. Located just moments from the renowned restaurants, boutiques, and vibrant atmosphere of St. Armands Circle and minutes to downtown Sarasota, the home offers an unbeatable island lifestyle. With estimated rental income potential of approximately $100,000 annually, this property presents a rare opportunity in one of Sarasota’s most desirable coastal communities.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tom Cail, Pa (941-780-2245)
106 N BLVD OF THE PRESIDENTS, SARASOTA, FL 34236
$1,900,000387 Days on yellowkey MLS ID: A4642792
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1999 Built: 1952 Tax: $25,393 (2024)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$25,393
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Sarasota Middle
Remarks: One or more photo(s) has been virtually staged. Exceptional investment opportunity at $1,900,000 in the heart of St. Armands Circle. Renovated coastal home on an oversized corner lot with strong rental potential in one of Sarasota’s most desirable vacation markets. Recent upgrades include impact-rated windows/doors, updated HVAC, beautifully remodeled kitchen and baths, pool pump, and water heater for true turnkey convenience. Open, light-filled floor plan with custom carpentry, detailed moldings, and coastal finishes throughout. Screened-in pool, private patio, and multiple outdoor living areas enhance guest appeal and occupancy potential. Ideally located minutes to Lido Beach, dining, shopping, and downtown Sarasota. Golf cart and pedestrian-friendly access to shops, restaurants, parks, and beach paths. Ideal for investors or dual-use ownership.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
130 N BLVD OF THE PRESIDENTS, SARASOTA, FL 34236
$3,800,00093 Days on yellowkey MLS ID: A4675644
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4335 Built: 2026 Tax: $18,800 (2024)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$18,800
High School: Booker High
Middle School: Booker Middle
Remarks: Pre-Construction. To be built. A rare new construction opportunity in one of Sarasota’s most iconic and walkable island neighborhoods. Located just steps from St. Armands Circle, this to-be-built luxury residence by Walsh Design & Build offers the chance to create a custom coastal home in the heart of one of Florida’s most sought-after destinations. The proposed residence features 4 bedrooms, 4.5 bathrooms, and approximately 4,335 square feet under air (5,650 total square feet), thoughtfully designed to embrace refined island living. Open-concept interiors, expansive living spaces, and abundant natural light create a seamless balance between sophistication and comfort, ideal for both everyday living and entertaining. Generously sized en-suite bedrooms and a private primary retreat provide flexibility for family, guests, or seasonal living. This premier location places you at the center of Sarasota’s most vibrant coastal lifestyle. World-class dining, boutique shopping, cafés, and galleries are just outside your door, while the sugar-white sands of Lido Beach are moments away by foot or bike. Downtown Sarasota’s cultural attractions, marina, and waterfront dining are a short drive over the Ringling Bridge, offering easy access to theaters, museums, and year-round events. Nearby destinations include the Sarasota Yacht Club, Longboat Key Club, and the area’s finest resorts, further enhancing the appeal of this exceptional address. Designed with Florida living in mind, the home plan allows for seamless indoor-outdoor living, with opportunities for a resort-style pool, covered lanai, and outdoor entertaining spaces. Here is your opportunity to collaborate with the builder, allowing buyers to tailor the residence to their personal vision and lifestyle. New construction opportunities of this scale and caliber in St. Armands are increasingly rare. Whether envisioned as a primary residence, seasonal retreat, or long-term investment, this offering presents a unique opportunity to build a home in a location defined by prestige, walkability, and timeless coastal charm.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kaisen Mitchell (941-726-7657)
128 FILLMORE DR, SARASOTA, FL 34236
$4,395,0008 Days on yellowkey MLS ID: A4686935
Bed: 8 Bath: 8.5 Liv Area Sq Ft: 4550 Built: 2023Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:
Tax Year:
Remarks: Discover an exceptional income-producing asset at 128 Fillmore Drive—an 8-bedroom, 8-bathroom luxury residence designed to perform at the highest level as a short-term vacation rental. Located just steps from world-renowned St. Armands Circle and minutes from the white- sands of Lido Key, this newly built, turnkey-furnished property offers the rare combination of prime location, high-capacity accommodations, and resort-style amenities that today’s travelers seek. Constructed with meticulous attention to durability and design, this home is purpose-built for both elevated living and strong rental performance. Expansive, sun-filled living areas and a coastal-contemporary aesthetic create a welcoming environment for large groups, while the gourmet chef’s kitchen—complete with custom cabinetry, quartz countertops, and premium appliances—supports effortless entertaining and extended stays. Each of the eight bedrooms features an ensuite bathroom, maximizing guest privacy and boosting rental desirability. Multiple balconies and a stunning rooftop terrace provide views of Sarasota Bay and the lush surrounding neighborhood—an unforgettable highlight for vacationers and a standout feature in rental marketing. The outdoor living experience is equally impressive, offering an oversized pool with a swim-up spa, generous patio space, and ample room for lounging or hosting gatherings. These resort-style amenities significantly enhance guest satisfaction and repeat bookings. With its unbeatable walkability to high-end shopping, fine dining, vibrant nightlife, and cultural attractions, plus immediate access to Lido Key’s turquoise waters, this property consistently checks every box for travelers seeking a luxury coastal getaway. Whether you’re expanding your portfolio or entering the short-term rental market, 128 Fillmore Drive represents a rare opportunity to acquire a high-performing asset in one of Sarasota’s most coveted destinations. This is more than a home—it’s a turnkey revenue generator in a premier vacation market.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
139 S WASHINGTON DR, SARASOTA, FL 34236
$14,950,000233 Days on yellowkey MLS ID: A4661401
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 7817 Built: 1936Community: Saint Armands Div John Ringling EstatesSingle Family
Remarks: Where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, the neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway and Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical property. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials and artisanship. Expanded from 4,000 to nearly 10,000 square feet under roof, and featuring over 7,800 square feet of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis and kayaks, and breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats and entertaining areas, all complemented by stunning garden water vistas, a central courtyard, and an elegant 65' saltwater pool and spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, and custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range and hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and a stand-alone ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, and curated artwork create an inviting, sophisticated atmosphere. Offering furniture (negotiable under separate contract), and instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance, and modern comfort on one of Sarasota’s most coveted waterfront estates. EASY TO SHOW. CASA DEL CARNEVALE IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.
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