Sarasota/Pinecraft Homes with Courtyard Exterior Features

Sarasota/Pinecraft Homes with Courtyard Exterior Features

Welcome to the enchanting region of Sarasota/Pinecraft, a hidden gem nestled in the heart of Central Sarasota, Florida. Known for its vibrant cultural scene, picturesque landscapes, and a warm, welcoming community, this area offers an idyllic lifestyle for those seeking a blend of relaxation and activity. With its proximity to stunning beaches, lush parks, and a plethora of dining and shopping options, Sarasota/Pinecraft is truly a paradise for both residents and visitors alike.

One of the standout features of homes in this charming locale is their exquisite courtyard exterior designs. These homes are thoughtfully crafted to create serene outdoor spaces that invite you to unwind and embrace the beauty of Florida's year-round sunshine. Imagine stepping out into your private courtyard, surrounded by lush greenery, vibrant flowers, and the soothing sounds of nature. Whether you’re sipping your morning coffee or hosting an evening gathering with friends, these courtyards provide the perfect backdrop for creating lasting memories.

Sarasota/Pinecraft is not just about beautiful homes; it’s also about a lifestyle filled with opportunities for exploration and connection. From the nearby cultural attractions, such as the Ringling Museum and the local farmer's markets, to the stunning beaches of Siesta Key and Lido Key, there’s always something to discover. The community is known for its friendly atmosphere, making it easy to forge new friendships and enjoy a sense of belonging.

If you're searching for a home that combines elegance with the charm of outdoor living, look no further than the courtyard homes in Sarasota/Pinecraft. Experience the best of Florida living in a community that truly feels like home.

Newest Sarasota/Pinecraft Homes with Courtyard Exterior Features

$1,550,000
6 Beds ⋅ 5 Baths ⋅ Long Meadow SubDv. ⋅ 34239 Zip Code
Welcome to this fully furnished, newly updated Sarasota property situated on two combined lots totaling nearly half an acre, offering the flexibility and lifestyle potential in one of the area’s most popular areas of Sarasota. This multiple six-figure producing Airbnb is located just 1.5 miles to Siesta Key and approximately 2 miles to downtown Sarasota, this property provides quick access to world-class beaches, dining, shopping, and entertainment. The main residence features an open-concept floor plan designed for comfortable living and entertaining. A separate in-law suite offers ideal accommodations for guests or extended family, while the detached pool house provides additional flexible space suitable for a game room, private retreat, or entertainment area. At the center of the property is a private courtyard with a large pool, creating a resort-style setting perfect for gatherings and outdoor enjoyment. The oversized double lot allows for ample parking and generous outdoor space, a rare find this close to the beach. Significant upgrades have been completed throughout the property, including a new roof, new A/C units, new electrical, new electrical panels, new water lines to the road, a new irrigation system, and exterior landscape lighting, offering peace of mind for future owners. Whether you are seeking a primary residence, second home, or a versatile property with multiple living areas, this Sarasota residence stands out for its location, lot size, and turnkey condition.

2069 Bougainvillea Street, Sarasota
$1,120,000
3 Beds ⋅ 3 Baths ⋅ Loma Linda Park SubDv. ⋅ 34239 Zip Code
CUSTOM-BUILT by Milano Homes in 2019, this CONTEMPORARY POOL HOME combines modern design, exceptional construction, and an unbeatable Arlington Park location and is offered TURNKEY FURNISHED. Situated on a private corner lot just blocks from Sarasota Memorial Hospital and minutes to Downtown Sarasota, Southside Village, Bayfront Park, the Legacy Trail, and Siesta Key Beach, this residence offers the ultimate Sarasota lifestyle. Inside, SOARING CEILINGS and an open-concept floor plan create a bright, airy living space designed for both everyday comfort and entertaining. The sleek EUROPEAN-STYLE KITCHEN showcases quartz countertops, glossy cabinetry, NATURAL GAS cooking, a large center island, pantry, and smart pull-out storage solutions. The spacious primary suite includes custom closet built-ins and an en suite bathroom featuring dual sinks and a walk-in shower. Enjoy seamless indoor-outdoor living with a SCREENED LANAI overlooking the PRIVATE POOL, mature landscaping, and privacy wall. A natural gas connection for grilling makes outdoor entertaining effortless year-round. Built for efficiency and peace of mind with CONCRETE BLOCK CONSTRUCTION, IMPACT WINDOWS AND SLIDERS, SMART HOME FEATURES, NATURAL GAS SERVICE, WHOLE-HOUSE GENERATOR, and an attached two-car garage. An incredible opportunity to own a newer custom-built home in sought-after Arlington Park, offering lock-and-leave convenience, contemporary style, and close proximity to Sarasota's best dining, shopping, healthcare, cultural attractions, and world-renowned beaches.

2373 Prospect Street, Sarasota
$4,100,000
4 Beds ⋅ 4 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate. From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island—ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique. Outside, the magic only continues—enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind. 1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character. Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.

1829 Bougainvillea Street, Sarasota
$176,000
2 Beds ⋅ 2 Baths ⋅ Cordova Gardens SubDv. ⋅ 34239 Zip Code
Welcome to maintenance-free living the the heart of Sarasota! This beautifully maintained 2-bedroom, 2-bath condominium offers an ideal blend of comfort, convenience and location. The spacious floor plan is light filled and has a great split bedroom floor plan and an ideal blend of comfort, convenience and location. In addition to the bright living areas, a functional kitchen and generously sized bedrooms there is a private primary suite with en suite bath. Enjoy relaxing mornings on one of 2 private lanais and take advantage of the community pool. Located just minutes from downtown and minutes to world class Siesta Key Beach and Village as well as South Side Village with many restaurants and shops as well as Sarasota Memorial Hospital. Whether you're looking for a year-round residence, seasonal retreat, or investment opportunity, this move-in ready condo is a fantastic value in a highly desireable location. New AC

2224 Bahia Vista Street Unit E6, Sarasota
$2,099,000
4 Beds ⋅ 6 Baths ⋅ Purtz Sub SubDv. ⋅ 34239 Zip Code
NEW PRICE — AN EXCEPTIONAL OPPORTUNITY IN SOUTH SARASOTA! Not every luxury home earns a name. This one does. Welcome to “ The Corner Estate ” an exceptional new construction that combines one of Arlington Park's largest corner homesites with timeless contemporary design, offering an opportunity that's becoming increasingly difficult to find in Sarasota. Positioned on an impressive 10,200-square-foot corner lot and offering nearly 3,600 square feet of thoughtfully designed living space, this residence delivers something today's luxury buyers value above all else: space, privacy, and versatility. Unlike homes that ask you to compromise, The Corner Estate was designed to adapt to every stage of life. A private elevator connects both levels, while two luxurious primary suites, one on each floor, create an ideal layout for multigenerational living, long-term guests, or homeowners who simply appreciate exceptional flexibility. The home's clean architectural lines, soaring ceilings, and expansive gathering spaces create an atmosphere that feels refined without sacrificing comfort. Whether hosting an intimate dinner, welcoming friends for the weekend, or enjoying a quiet evening at home, every space was designed to feel effortless. Outside, the experience continues. The heated saltwater pool and spa overlook a generously sized backyard, an uncommon luxury in Arlington Park, offering room to entertain, relax, or simply enjoy the privacy that only an oversized corner homesite can provide. Location is where convenience becomes lifestyle. From your front door, you're only minutes from Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, Siesta Key Beach, and some of the city's finest restaurants, boutiques, galleries, and waterfront destinations. The Corner Estate represents one of the strongest values in Arlington Park's luxury new construction market. While others compete on size or price, this home delivers the rare combination of location, design, functionality, and long-term value. Some homes are easy to compare. The Corner Estate isn't one of them. Experience it in person and discover why this is one of Arlington Park's most compelling luxury opportunities.

2010 Hyde Park Circle, Sarasota
$4,000,000
5 Beds ⋅ 4 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code
Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary design with seamless indoor-outdoor living. New roof 7/2026!!! Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this exceptional modern residence delivers a rare blend of warm contemporary design, luxury finishes, and seamless indoor-outdoor living. Perfectly scaled for the neighborhood, the open floor plan is flooded with natural light and effortlessly blurs the line between inside and out. The great room features 8-ft pocketing sliders opening to the covered lanai, anchored by a gas fireplace with illuminated floating shelves. The chef’s kitchen is a showpiece with top-of-the-line Miele appliances, solid wood cabinetry, an expansive quartz island, LED lighting, and a butler’s pantry for effortless entertaining. A separate dining room with picturesque windows offers an inviting setting for intimate gatherings, while the adjoining family room provides a relaxed space to unwind. The first-floor primary suite is a serene retreat with walls of windows overlooking lush tropical foliage and a spa-inspired bath featuring a soaking tub and glass shower. A dedicated office/flex room is conveniently located on the main level. Owners thoughtfully converted the sunroom into a 5th bedroom, offering added flexibility for guests or multigenerational living. Sleek open-riser stairs lead upstairs to two en-suite bedrooms providing privacy and comfort.

1347 Harbor Drive, Sarasota
$8,750,000
5 Beds ⋅ 5 Baths ⋅ Bay View Heights SubDv. ⋅ 34239 Zip Code
Nestled in the heart of Sarasota, Florida, "The Seathrough House" stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architectural firm Sweet Sparkman and meticulously crafted by builder Josh Wynne, this mid-century marvel redefines luxury living. From the moment you step inside, the panoramic bay views captivate the senses, seamlessly blending the indoors with the breathtaking natural beauty of the surroundings. Every room boasts expansive windows, offering an uninterrupted vista of Sarasota Bay that is nothing short of mesmerizing. This architectural masterpiece features five bedrooms and five baths, providing ample space for both relaxation and entertaining. Each room is thoughtfully designed to maximize comfort and functionality while showcasing the stunning waterfront backdrop. Situated "West of the Trail," this premier location places you just minutes away from the world-renowned Siesta Beach, downtown Sarasota, and the charming Southside Village. Whether you're strolling along the pristine shores of Siesta Key or indulging in the vibrant cultural scene of downtown, every convenience is within easy reach. For those who appreciate the finer things in life, "The Seathrough" house offers more than just luxurious living—it promises a lifestyle of unparalleled elegance and sophistication. With a shared dock featuring a 16,000 lb lift, residents can effortlessly explore the azure waters of the Gulf Coast or simply bask in the warmth of the Florida sun as they watch the gorgeous sunsets from the home or the bayfront poolpaint the sky in hues of orange and gold. "The Seathrough" house is not just a home—it's a sanctuary where every moment is infused with beauty, tranquility, and the unmistakable charm of Sarasota living at its finest.

1500 Bayview Drive, Sarasota
$209,000
2 Beds ⋅ 2 Baths ⋅ Cordova Gardens SubDv. ⋅ 34239 Zip Code
Welcome to this beautifully maintained end-unit condominium ideally situated in one of Sarasota’s most sought-after neighborhoods. Just minutes to vibrant downtown Sarasota’s arts district, offering fine dining, boutique shopping, theaters, and cultural venues. Close to the scenic Bayfront Park and Marina Jack, perfect for waterfront dining, walking trails, and watching sunsets over Sarasota Bay. Easy access to Sarasota Memorial Hospital, world-class beaches (including Siesta Key and Lido Beach), and premier golf courses. This spacious 2-bedroom, 2-bath split-plan layout offers privacy and comfort, ideal for both seasonal or year-round living. As an end unit, this home features extra privacy and natural light, enhanced by soaring vaulted Pecky Cypress ceilings and large transom windows that fill the open-concept living area with abundant light, while adding warmth and architectural character. The open floor plan includes a spacious kitchen, perfect for entertaining, and flows into the main living and dining areas. Enjoy a bonus loft perfect for a home office, guest space, or creative studio, and relax on two private, screened-in lanais—ideal for morning coffee or evening cocktails. Additional features include updated bathrooms, in-unit laundry, and plenty of storage throughout. Whether you're looking for a primary residence, seasonal retreat, or an income-producing property (with 6-month rental capability), this home offers the best of Sarasota living in an unbeatable location.

2232 Bahia Vista Street Unit A6, Sarasota
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