Refine Search
Map
Sort by
$8,830,000
4 Beds ⋅ 5 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
Rarely available! This coastal contemporary masterpiece sits on 18,000 square feet of prime bayfront on St. Armands Key. Unobstructed views of Sarasota Bay create a stunning backdrop from every angle, enhancing the beauty of this custom-built home, completed in 2021. Offering 5,064 square feet of elegant living space, the residence features four bedrooms, four and a half baths, and two bonus rooms easily adaptable as extra bedrooms. Expansive decks and lush outdoor areas capture the essence of Florida living. Inside, an airy, open floor plan connects a light-filled living room, cozy sitting area with an electric fireplace, and a chef’s kitchen equipped with high-end appliances. The serene master retreat, with an expansive terrace, offers dramatic views of the pool and bay, where each sunrise unfolds like a masterpiece, inviting tranquility and inspiration. Two additional guest suites, each with private terraces, and a third suite with a built-in Murphy bed, provide ample comfort and privacy. Outside, a two-tiered stone deck, saltwater pool, firepit, and verdant landscaping are perfect for entertaining or tranquil al fresco dining. Boaters will appreciate the dock accommodating a 15,000-pound vessel, with a lower launch for kayaks and canoes. Practical conveniences include a whole-house water filtration system, three HVAC zones, a generator, elevator, security systems, and two one and a half garages with electric car chargers and epoxy-coated floors. When you're ready to venture beyond your private paradise, the chic boutiques and acclaimed restaurants of St. Armands Circle are just two blocks away. The sands of Lido Beach are just beyond, and the vibrant energy of downtown Sarasota is only a quick drive over the John Ringling Causeway. Enjoy the best life in this spectacular waterfront retreat in the heart of a community of culture and natural beauty. All offers must be accompanied by Proof of Funds.

178 N Washington Drive, Lido Key
$3,500,000
4 Beds ⋅ 5 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
Owner Will Entertain Offers. A Rare Waterfront Sanctuary on St. Armands – Unrivaled Views, Elegant Design, Exceptional Location. Perfectly positioned on 110 feet of boating water, this stunning coastal modern residence offers captivating open views of Pansy Bayou with a rooftop glimpse of the Gulf of Mexico. Just two blocks from the world-class dining and boutiques of St. Armands Circle and moments from the sugar sands of Lido Beach, this home blends architectural elegance with effortless coastal living. Floor-to-ceiling windows and soaring ceilings flood the interior with natural light, showcasing breathtaking water vistas from nearly every room. Thoughtfully designed for both everyday comfort and grand entertaining, the open-concept layout features 4 spacious bedrooms and 4 bathrooms—including a luxurious primary suite with a private sunroom/home office. The kitchen is a chef’s dream, outfitted with top-of-the-line Thermador appliances, including a professional-grade 6-burner gas range, wine cooler, and newer refrigerator. Outdoor living is equally impressive with a resort-style pool deck, lush mature landscaping, and a rooftop terrace offering unforgettable sunsets over the Gulf. Meticulously maintained and move-in ready, the home includes a new roof (2024), recently replaced seawall (2017), dual-zoned Rheem A/C systems, electric hurricane shutters, whole-home speaker system, and a secure gated entrance for ultimate privacy and peace of mind. FEMA-compliant with the main living level elevated 12.1 feet above base flood elevation, this property offers both safety and sophistication. Located directly across from a protected bird sanctuary, this peaceful retreat is a haven for nature lovers—where dolphins and manatees are frequent visitors.

360 N Washington Drive, Lido Key
$2,750,000
4 Beds ⋅ 4 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
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!

408 Jackson Drive, Lido Key
$2,500,000
3 Beds ⋅ 4 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
New Price – Now Offered Under $3 Million Some homes simply feel right the moment you arrive—and 121 N Blvd of the Presidents is one of them. Just steps from the charm and energy of St. Armands Circle and a short walk to Lido Beach, this is where everyday life begins to feel like a permanent vacation. This property has undergone a meticulous, room by room renovation; a passion project by the current owners...simply nothing more to do but enjoy. Imagine slow mornings by the heated saltwater pool, a cup of coffee in hand, surrounded by swaying palms and sunshine. Evenings are for easy strolls to dinner, sunsets on the beach, and returning to the peaceful privacy of your own tropical retreat. This updated 3-bedroom, 3-bath home offers almost 3500 sq ft of natural light-filled living, thoughtfully designed for both comfort and connection. The open layout, chef’s kitchen, and spacious primary suite with private terrace invite relaxation, while multiple outdoor spaces set the stage for gatherings with friends and family. Built for peace of mind with a whole-house generator and hurricane shutters, this home offers more than beauty—it offers security, ease, and a place to belong. Now priced under $3 million, this is your opportunity to own a timeless Sarasota escape—perfect for snowbirds or anyone ready to live where others vacation. Schedule your private showing and experience the feeling for yourself. Ask us (or your realtor) about the available video tour.

121 N Boulevard Of Presidents, Lido Key
$2,200,000
Saint Armands Division John Ringling Estates SubDv.
The first time this parcel has been available in almost 40 years! This large corner lot is only one block to the beach. It is already gated and walled, with a dock and seawall. Bring your builder and create more memories on this landmark, oversized property. Situated on a quiet canal leading into Pansy Bayou, where manatees and fish are plentiful. The waterfront location is perfect for a small motorboat and kayaking. The entry faces N. Washington and the address could be changed to reflect the N. Washington location. Recreation is endless with this waterfront canal and close to the beach location, with restaurants and shopping at your doorstep. You can have it all here!

259 John Ringling Boulevard, Lido Key
$1,631,000
2 Beds ⋅ 2 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
What if you could own a fully renovated beach house on St. Armands Circle for the price many buyers are paying for an outdated condo… while being surrounded by $3M-$10M homes just blocks from the Gulf? Welcome to 409 N Washington Drive, an exceptionally rare opportunity to own one of the least expensive fully renovated homes to become available on St. Armands in years. Perfectly positioned just two blocks from the world-famous boutiques, restaurants, and cafés of St. Armands Circle, and only three blocks from the beautiful beaches of Lido Key, this charming single-story bungalow captures the kind of lifestyle most only experience on vacation. And here, vacation never has to end. Tucked away on one of the quietest streets on the Key, this beautifully updated 2-bed, 2-bath residence spans about 1700 SF and has been thoughtfully designed to deliver effortless coastal living with a resort-style feel. Lush tropical landscaping creates a sense of privacy rarely found this close to the beach and Circle, while multiple outdoor patios, lounging areas, and a sparkling resort-style pool invite year-round indoor-outdoor living and entertaining. Behind the charming exterior is a completely updated residence designed for effortless ownership, low-maintenance living, and maximum enjoyment. The home has undergone extensive renovations including updated PVC plumbing, updated electrical systems, hurricane-rated impact windows and doors, renovated kitchen and bathrooms, upgraded flooring, modern finishes, updated appliances, and refreshed indoor-outdoor living spaces. Every detail was intentionally curated to create a bright, inviting atmosphere that feels relaxed, elevated, and move-in ready from day one. Unlike many older island properties that become renovation projects disguised as opportunities, 409 N Washington removes the uncertainty, expense, and disruption buyers often fear when purchasing near the coast. There is no looming “what will break next?” anxiety here. The heavy lifting has already been done. For investors, this property checks nearly every box that drives premium short-term rental performance: an iconic walkable location, proximity to the beach, strong luxury rental demand, a fully furnished turnkey setup, and a proven St. Armands address that has historically outperformed many Sarasota County markets in appreciation and desirability. Offered furnished, including household goods, linens, décor, and months of future bookings in place, this is the type of property capable of generating strong occupancy with minimal downtime while also serving as a long-term appreciation play in one of Florida’s most supply-constrained markets. For lifestyle buyers, the appeal becomes even more personal. Imagine morning walks to coffee on the Circle, afternoons at Lido Beach, sunset dinners without needing a car, and evenings entertaining poolside after a day on the water. Whether used as a seasonal retreat, a lock-and-leave second home, or a full-time residence for a buyer seeking a lower-maintenance alternative to condominium living, this home delivers the rare combination of freedom, convenience, privacy, and coastal charm. In an area where many properties require extensive updating or command significantly higher prices, this home represents a rare opportunity to own a turnkey St. Armands residence with lifestyle appeal, income potential, and long-term investment strength wrapped into one exceptionally charming property.

409 N Washington Drive, Lido Key
$1,600,000
Saint Armands Division John Ringling Estates SubDv.
Prime Vacant Lot in the Heart of St. Armands Circle – Rare Opportunity. Seller will entertain offering owner financing. Discover one of the most coveted pieces of real estate in Sarasota – a large 17,588 SF vacant lot perfectly positioned in the heart of St. Armand’s Circle. Surrounded by multi million dollar homes, world-class restaurants, boutique shopping, and vibrant nightlife, this location offers the ultimate Sarasota lifestyle. Lido Beach is just moments away, while the cultural attractions and waterfront beauty of downtown Sarasota are a short drive over the Ringling Bridge. Whether you envision a luxury coastal retreat or a savvy investment in one of Florida’s most sought-after areas, this rare offering is your chance to own a piece of paradise in an iconic location.

204 N Adams Drive, Lido Key
$1,600,000
2 Beds ⋅ 2 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
MOVE-IN READY WATERFRONT — MAJOR PRICE REDUCTION - Photos have Virtual Staging Walk to St. Armand's, Lido Beach & the St. Regis | 7-Day Rentals | Full Gulf Access Set on the widest stretch of Pansy Lagoon with 187' of frontage, this rare coastal gem sits on a reverse pie-shaped lot that opens to 152' deep lot, creating a private, sun-splashed backyard retreat wrapped by privacy walls. Inside, the home has been professionally remodeled to the studs—new kitchen & baths, drywall, counters, doors; new HVAC (2025); new water heater (2025); new ductwork; updated electrical; and brand-new pool equipment (2025)—so you can move right in and start living. Major structural essentials were completed in 2018: roof, windows, exterior stucco, seawall, and dock (dock installed 2018; now simply needs resetting by a marine contractor). For peace of mind, enjoy electric hurricane shutters, remote privacy screens, and hurricane-rated shades. This location is unbeatable—stroll to world-famous Lido Beach, dine and shop at St. Armand's Circle, and visit the newly opened St. Regis Resort. Launch kayaks or a boat for full Gulf access, then float in your pool while dolphins play in the lagoon. With 7-day rental eligibility, this is both an exceptional personal retreat and a high-demand income opportunity. Turnkey. Walkable. Boatable. The Sarasota waterfront lifestyle—delivered.

321 N Boulevard Of The Presidents, Lido Key
$1,335,000
3 Beds ⋅ 2 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
Virtually Staged. Charming Mid-Century Ranch on Saint Armands | Oversized Lot. Welcome to your slice of paradise on the coveted Saint Armands in Sarasota, Florida. This sturdy mid-century ranch home offers the perfect blend of timeless character and modern comfort. Situated on an oversized lot, this 3-bedroom, 2-bathroom residence provides ample space for relaxation, entertaining, or future expansion. Step inside to discover a natural light-filled floor plan with classic mid-century details and an inviting atmosphere. The generous living area with vaulted ceilings flows seamlessly, creating a warm, welcoming environment ideal for both everyday living and entertaining guests. Enjoy peace of mind with major updates already in place, including a newer roof (2021) and HVAC system (2023)—ensuring comfort and efficiency for years to come. Outside, the expansive yard offers endless possibilities—from 2 existing outdoor hot water showers to lush landscaping and outdoor dining spaces to room for a pool or garden oasis. Just a short stroll to the boutiques and dining of Saint Armands Circle and minutes to the pristine shores of Lido Beach, this home is perfectly positioned to enjoy the best of coastal Sarasota living. Don’t miss this rare opportunity to own a classic gem in one of Sarasota’s most desirable neighborhoods. Private showings available.

130 N Adams Drive, Lido Key
$1,245,000
3 Beds ⋅ 2 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
One or photo (s) have been virtually staged. Lowest priced single family home on Saint Armands. Really charming beach style cottage that has been completely updated with beautiful appointments. This 3 bedroom, two bath home is located in a superb location in the SW quadrant of the Key. Step out your front door to world class shopping, dinning and entertainment. Public beach is only one block away. Newer flat tile roof 2018. New A/C and Water heater. New GE Profile appliances. This sweet little home is ideal for a second home retreat or income property with 1 week rental minimum and no HOA fees. Surrounded by Multi Million Dollar Homes. Rebuild your new home here. The true value is in the land.

323 Madison Drive, Lido Key
$1,200,000
Saint Armands Division John Ringling Estates SubDv.
Sarasota island living on world-renowned St. Armands Circle. Walk to five-star restaurants, chic boutiques, coffee houses and ice cream shops. Stroll to Lido Beach to rejoice in year-round blue skies, Gulf breezes and Sarasota’s spectacular sunsets. Downtown Sarasota, with its eclectic mix of shopping, dining, boating, culture and the arts, is just over the iconic Ringling Bridge aboard the free Bay Runner trolley which runs from downtown to south Lido with multiple stops in between. A distinctive St. Armands Key address is now available on this .26-acre homesite, an exceptional 75-by-152-foot lot on which to build the coastal home of your dreams. To imagine the possibilities, Mark Sultana of DSDG Architects designed a three-story, contemporary home featuring a roof deck with bay view suitable for this lot. The plans, although perfect for this lot, can be modified for your specifications. The proposed home design and floor plans are available for your review. The price offered is for the lot only. St. Armands Key is home to a distinguished residential community surrounding the picturesque and world-renowned St. Armands Circle. The Circle provides year-round amenities including fine and casual dining, shopping, banking, salons, spas, art galleries and a variety of professional services. In addition, the City of Sarasota, St. Armands Residents Association and St. Armands Circle merchants sponsor seasonal events and art fairs culminating in the lighting of the 60-foot tall Christmas tree during the Holiday Night of Lights. St. Armands, Downtown Sarasota, Lido Beach– welcome to an enchanted coastal lifestyle sure to please family, friends, and especially you!

25 N Washington Drive, Lido Key
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
One of the best prices in the St Armand's Circle area, this property is priced at lot value. Featuring a 10,858 sq ft (.25 acre) lot, that is one block to the popular shops and restaurants on the renowned Circle and an easy stroll to the beach. The existing 3 bedroom 2.5 bath home did have water intrusion but could be rehabbed. No HOA restrictions and easy access to downtown Sarasota. Highly desirable neighborhood for both homeowners and vacation rental purchasers.

153 N Adams Drive, Lido Key
$1,042,000
Saint Armands Division John Ringling Estates SubDv.
Seize a rare opportunity to own and build on Sarasota’s iconic St. Armands Key. Just steps from the boutiques and dining of St. Armands Circle and the white sands of Lido Beach, this 7,657 sq. ft. homesite (RSF-2 zoning) has been fully prepped and is truly ready to go. The sellers have already invested the time and resources: demo has been permitted and completed, the lot is cleared, utilities are available, and preliminary architectural site plans are included. Adding to this turnkey advantage, FL licensed Sarasota-based Certified General Contractor, Coral Cove Construction, Inc. is aligned and ready to begin your new project, if desired. For a buyer, this removes one of the hardest hurdles in today’s market—securing a trusted GC with availability. Whether moving forward with the included coastal luxury design or creating something entirely custom, the path to construction is streamlined from day one. Surrounded by new construction homes commanding $4M–$6M+, this parcel is competitively positioned at $1.295M. For the developer, the ROI math is compelling: plans in place, CGC aligned, and seasonal demand building as feeder markets flow into Sarasota. For the retail buyer, it is a chance to create a dream home in a neighborhood where lifestyle and legacy meet—walking distance to the Circle, the beach, and the unmatched energy of Sarasota’s waterfront living. This is more than land—it’s a build-ready, shovel-ready opportunity to deliver your vision on one of Florida’s most iconic Keys.

236 N Blvd Of The Presidents, Lido Key