Lido Key Homes with Courtyard Exterior Features

Lido Key Homes with Courtyard Exterior Features

Welcome to Lido Key, a hidden gem nestled in the heart of Sarasota County, Florida. This picturesque barrier island is renowned for its stunning beaches, vibrant culture, and a laid-back lifestyle that attracts both residents and vacationers alike. With its powdery white sands and crystal-clear waters, Lido Key offers a tropical paradise where you can bask in the sun, indulge in water sports, or take leisurely strolls along the shore.

One of the standout features of homes in Lido Key is their enchanting courtyard exterior designs. These charming courtyards create a seamless blend of indoor and outdoor living, offering a private oasis for relaxation and entertainment. Imagine sipping your morning coffee surrounded by lush landscaping or hosting evening gatherings under the stars in your own secluded retreat. The courtyard space enhances the overall aesthetic of the home, providing a serene backdrop that complements the island's natural beauty.

Living in Lido Key means you’re just moments away from world-class dining, boutique shopping, and exciting recreational activities. Explore the nearby St. Armands Circle, where you can find unique shops and delectable eateries, or take a short drive to the cultural offerings of downtown Sarasota.

Whether you’re seeking a vacation home or a permanent residence, Lido Key’s charming properties with courtyard features offer a perfect blend of elegance and coastal living. Embrace the tranquility and beauty of this extraordinary island community, where every day feels like a vacation. Discover your dream home in Lido Key today!

Newest Lido Key Homes with Courtyard Exterior Features

$700,000
2 Beds ⋅ 2 Baths ⋅ Kingston Arms SubDv. ⋅ 34236 Zip Code
Whether your primary residence, second home, or investment property, this first-floor 2 bed/2 bath condo in Kingston Arms provides a walkable lifestyle second to none. This "hidden gem" is directly behind the shops, dining, and entertainment destinations found on St Armands Circle, and just a short walk to Lido Beach. Kingston Arms rarely has availability due to its amazing location. This fully renovated and turnkey furnished condo offers an open floor plan filled with light from the sliding doors opening to your private screened patio. The kitchen and 2 bathrooms have been beautifully updated with thoughtful finishes, including gorgeous new counters, cabinetry, appliances, and beautiful tiles in both showers. Custom blinds, fresh paint, modern floorboards, and large neutral tiles enhance each room. The primary suite is large enough for a king-size bed and features a walk-in closet, linen closet, and en-suite bathroom with step in shower. The guest bedroom has loads of closet space and an en-suite bath. Additional upgrades include new A/C and wi-fi thermostat, recessed LED lighting, and an interior laundry closet with full size washer/dryer. One covered parking space is included. A small pet is allowed, as are one-month rentals, up to 12 times a year.

500 S Washington Drive Unit 6A, Sarasota
$325,000
1 Baths ⋅ Pelican Gardens SubDv. ⋅ 34236 Zip Code
Welcome to 170 Roosevelt Dr. Unit #8,at Pelican Gardens a beautifully updated studio/efficiency, one-bath condo located just steps from the powdery sands of Lido Beach and the world-class shopping and dining of St. Armand's Circle. Completely remodeled in November 2024, this light and bright ground-floor unit offers a fresh, modern coastal aesthetic with new flooring, stylish fixtures, and a sleek kitchen featuring stainless steel appliances and quartz countertops. Perfect as a beachside getaway or an investment property with excellent rental potential, this turnkey condo offers the ultimate Sarasota lifestyle. Enjoy morning strolls along the Gulf, sunset views, and the convenience of being minutes from St. Armands, downtown Sarasota’s arts and cultural scene. Low HOA fees, and a well-maintained community complete the package for units 5,17,19. Whether you’re looking for a vacation getaway or a smart investment, Unit #8 is move-in ready and waiting for you.

170 Roosevelt Drive Unit 8, Sarasota
$2,399,000
4 Beds ⋅ 3 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code
Welcome to 103 Fillmore Drive, a beautifully renovated 4-bedroom (or 3 bedroom plus den/office), 3-bath pool home with an assumable flood policy 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.

103 Fillmore Drive, Sarasota
$13,950,000
5 Beds ⋅ 7 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
DIRECT GULF FRONT Modern Estate with 135 ft. of private beachfront on Lido Beach. This gated 3-story residence offers 4,751 sq. ft., with 5 bedrooms, 5 baths, 2 half baths, and unobstructed panoramic Gulf views from every level. Expansive terraces, floor-to-ceiling glass, and seamless indoor-outdoor living highlights the coastal lifestyle. Designed for flexibility, both the 2nd and 3rd floors include full living, dining, and primary suites—ideal for multigenerational living or rental income potential. The 2nd-floor lanai features automated screens, an infinity-edge pool & spa, and open sundeck. The 3rd floor offers a vast living space, wet bar, large sundeck, and a luxurious primary suite with dual sinks, soaking tub, separate water closet with bidet, and a large walk-in shower and closet. Premium features include a 3-car garage, elevator, 1,300 sq. ft. storage room, generator, Crestron Home automation, Sonos sound system, motorized shades, gas appliances, zoned A/C, and advanced security with surveillance. Just a short walk to St. Armands Circle and minutes to Downtown Sarasota, this exceptional property combines architectural excellence, privacy, and world-class beachfront living.

160 Whittier Drive, Sarasota
$2,050,000
2 Beds ⋅ 2 Baths ⋅ St Armands Division SubDv. ⋅ 34236 Zip Code
Virtually Staged. Hidden behind lush plantings is this beautifully redesigned and amazingly private two-story home boasting over 3900 sq ft of interior living space all moments away from the shops & cafes of St. Armands Circle, the beaches of Lido Key & downtown Sarasota. As you enter this hideaway of peace and tranquility you are greeted by a fountained courtyard garden through gates of aged iron. From there the interiors will call to the imagination as it evokes the visions of a bastide in Provence or a country home in the hills of Scotland. Imperfection is curated and intentional. Rooms flow easily enhanced by wide plank reclaimed wood floors, white ship lap walls framed with wood accents, reclaimed wood beams artfully placed throughout, thick roughhewn interior doors with patinaed hardware, an eclectic kitchen design with soap stone counters, side tables and oven backsplash, a double farm sink, a new 10- burner dual fuel gas range with two ovens, a Sub-Zero fridge with a glass door & four bottom draws to name just a few of the many appealing details. A grand front room leads to a beautiful staircase of wood and clay tiles with a landing at the center of the house leading you to the primary suite, encompassing the entire second floor. Here we have a library/seating room lined with bookshelves, roughhewn wide plank wood floors, a spacious bedroom with a Julliet balcony, two walk-in closets and bath with a tub, large quartz shower with horizontal subway tiles, dual shower heads & handheld and two vanities with surface mount sinks and quartz counters sitting on retrofitted antique cabinets. There is a loggia spanning the width of the house opening on to an exceptionally large backyard bursting with lush tropical foliage. The nearly 12,000 sq ft lot is 160 ft deep. Intricately laid clay tiles form multiple walkways and an extensive lounging area. Beautifully weathered custom wrought iron gates abound not only on the drive entry but also on the courtyard and on the arched window openings of the loggia. Aged clay tiles surround windows and doors, even the garage door. Custom crafted metal awnings adorn the windows. Exterior custom metal lanterns and sconces echo the same intentional aging. There are two tankless water heaters, a whole house water purifier and a well for the yard. This home will captivate you.

41 S Adams Drive, Sarasota
$1,300,000
4 Baths ⋅ Pelican Gardens SubDv. ⋅ 34236 Zip Code
Rare Income-Producing Portfolio on South Lido Key – 4 Turnkey STR Units A rare opportunity to acquire a fully operating short-term rental portfolio on South Lido Key, one of Sarasota’s most coveted coastal markets. This offering includes 4 updated studio units within a boutique beachside community just steps from two direct beach access points and a short ride to St. Armands Circle. Each unit is managed, actively listed, and consistently booked, delivering proven performance and strong guest demand year-round. These condos have a long track record as successful Airbnb rentals, with 2024 gross income averaging $38,470 per unit and portfolio-wide net income of $85804 after HOA, taxes, utilities, and cleaning expenses. This is a cash-flowing, turnkey asset in a high-barrier-to-entry vacation rental market. The property features a community pool and sliding glass access private patios for each unit, creating the indoor/outdoor lifestyle guests expect on Lido. Interiors have been updated over the years and show pride of ownership throughout. Major mechanical systems are in good condition, with recent A/C and hot water tank replacements across the portfolio for peace of mind. Unit Renovation & Mechanical Summary: • Unit 10 – Updated | AC ~2 yrs | WH < 6 yrs • Unit 11 – Updated | AC ~3 yrs | WH < 3 yrs • Unit 12 – Updated | AC ~2 yrs | WH < 3 yrs Unit 6 - Updated AC is 3 years and WH is 3 years This type of offering is rarely available — a multi-unit STR package on Lido Key with documented income history, repeat traveler base, and proven operational infrastructure already in place. Keep as a turnkey portfolio, self-manage, or explore value-add improvements and dynamic pricing to further enhance returns. 4 units. One unbeatable coastal investment. Opportunities like this do not come around often.

170 Roosevelt Drive Unit 10, Sarasota
$375,000
1 Beds ⋅ 1 Baths ⋅ Pelican Gardens SubDv. ⋅ 34236 Zip Code
Welcome to 170 Roosevelt Dr. Unit #5,at Pelican Gardens a beautifully updated studio/efficiency, one-bath condo located just steps from the powdery sands of Lido Beach and the world-class shopping and dining of St. Armand's Circle. Completely remodeled in November 2024, this light and bright ground-floor unit offers a fresh, modern coastal aesthetic with new flooring, stylish fixtures, and a sleek kitchen featuring stainless steel appliances and quartz countertops. Perfect as a beachside getaway or an investment property with excellent rental potential, this turnkey condo offers the ultimate Sarasota lifestyle. Enjoy morning strolls along the Gulf, sunset views, and the convenience of being minutes from downtown Sarasota’s arts and cultural scene. Low HOA fees, a pet-friendly policy, and a well-maintained community complete the package for units 8,17,19. Whether you’re looking for a vacation getaway or a smart investment, Unit #5 is move-in ready and waiting for you.

170 Roosevelt Drive Unit 5, Sarasota
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