Sarasota/Pinecraft Homes with Private Pool type

Sarasota/Pinecraft Homes with Private Pool type

Welcome to the charming community of Sarasota/Pinecraft, a hidden gem nestled in the heart of Central Sarasota, Florida. Known for its picturesque landscapes, vibrant culture, and warm, welcoming atmosphere, this region is a haven for those seeking a perfect blend of relaxation and adventure. With its proximity to stunning beaches, lush parks, and a variety of dining and shopping options, Sarasota/Pinecraft offers an unparalleled lifestyle that caters to both families and retirees alike.

One of the standout features of homes in this delightful area is the availability of properties with private pools. Imagine stepping out into your backyard oasis, where you can soak up the Florida sun, host lively gatherings, or simply unwind in your own serene retreat. These homes provide the perfect setting for creating cherished memories with family and friends, all while enjoying the ultimate comfort and privacy.

Sarasota/Pinecraft is not just about stunning homes; it’s about a vibrant community that embraces a slower pace of life. The area is rich in cultural attractions, including art galleries, theaters, and the renowned Ringling Museum, making it an ideal location for those who appreciate the arts. Additionally, with year-round warm weather, residents can enjoy outdoor activities such as biking, golfing, and beach outings, fostering an active and engaging lifestyle.

Whether you’re looking for a cozy retreat or a spacious family home, Sarasota/Pinecraft offers a variety of real estate options that cater to every taste. Come discover the magic of this enchanting region, where your dream home with a private pool awaits!

Newest Sarasota/Pinecraft Homes with Private Pool type

2201 Webber Street, Sarasota
$1,100,000
4 Beds ⋅ 4 Baths ⋅ South Side Park SubDv. ⋅ 34239 Zip Code
INCOME TODAY. HOME TOMORROW. OPPORTUNITY ALWAYS. An incredible opportunity to own a beautifully renovated, FULLY TURNKEY Sarasota retreat offering the best of both worlds: a family-ready residence and an established income-producing investment! Located in desirable ARLINGTON PARK, this 4-bedroom, 3.5-bath home features 2,267 square feet of living space, a 2-car garage, and a private resort-style pool with heater and chiller. With approximately six years of short-term rental history, the property has generated approximately $75,000 annually while allowing the sellers to reserve 12 weeks each year for personal enjoyment. The seller reports approximately $44,000 in future bookings through the existing property management company. COMPLETELY RENOVATED in 2020, the home features an open floor plan, luxury vinyl flooring, modern finishes, and a spacious kitchen with stone countertops and a large center island. IMPACT windows and doors, a METAL roof, and TURNKEY furnishings add to its appeal and value. Step outside to your private tropical oasis featuring a heated saltwater pool, expansive paver deck, covered entertaining area, built-in grilling island, mature landscaping, and privacy fencing. Situated on a spacious corner lot, the property also offers convenient side ACCESS FROM GROVE PLACE. Enjoy a prime Sarasota location less than 10 minutes from VIBRANT DOWNTOWN SARASOTA and the WORLD-FAMOUS SIESTA KEY BEACH, with convenient access to dining, shopping, entertainment, and coastal attractions. Whether you're seeking a full-time family residence, a Florida vacation getaway, or an investment opportunity with established rental history, this versatile property offers exceptional flexibility. Move right in, enjoy your own private retreat, or continue its income-producing potential while potentially offsetting ownership costs. A beautifully updated home. An established rental history. ENDLESS POSSIBILITIES TO ENJOY THE FLORIDA LIFESTYLE ON YOUR TERMS.

2201 Webber Street, Sarasota

1805 Goldenrod Street, Sarasota
$3,790,000
5 Beds ⋅ 5 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully curated living space. Designed with a refined modern aesthetic, the home blends clean architectural lines with elevated finishes and seamless indoor-outdoor living. Upon entry, soaring 20-foot ceilings, warm designer lighting, and an expansive open-concept floor plan create an immediate sense of scale and refinement. The chef’s kitchen is appointed with premium GE Café appliances, quartz countertops, and custom cabinetry, flowing effortlessly into the main living and entertaining spaces. The residence also includes a spacious two-car garage equipped with an installed electric vehicle charger for added convenience and modern functionality. Walls of sliding glass doors open to a beautifully enhanced outdoor retreat featuring lush upgraded landscaping, a resort-style pool with a newly added waterfall feature, a fully equipped outdoor kitchen, and a covered dining area complete with remote-controlled mosquito and sun screens for year-round comfort and effortless entertaining. The primary suite serves as a private sanctuary, filled with natural light and designed for both comfort and elegance. The space features a generous walk-in closet, direct access to the outdoor living area, and a spa-inspired bath with a soaking tub and separate glass-enclosed shower. A newly installed stainless steel Bosch built-in coffee system adds an additional layer of luxury, while designer wallpaper and remote-controlled screens throughout the home provide a refined finish and enhanced comfort. Upstairs, three spacious guest suites each feature their own en-suite bathroom, creating ideal accommodations for family and visitors alike, in addition to a spacious media room designed for relaxed living and entertaining. A large rooftop terrace overlooking the pool provides an exceptional setting for relaxing or entertaining. Perfectly positioned between Siesta Key and Downtown Sarasota, this residence offers convenient access to world-class beaches, dining, shopping, and cultural attractions. Thoughtfully designed with timeless architecture, elevated finishes, and exceptional attention to detail throughout, this home delivers an elevated yet comfortable living experience for modern luxury living.

1805 Goldenrod Street, Sarasota

1800 Webber Street, Sarasota
$4,490,000
4 Beds ⋅ 6 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of Southside Village. Enjoy the convenience of a circular driveway with a custom paver design and garage space for three cars. With striking architecture, impeccable craftsmanship, and beautiful, thoughtfully curated finishings—showcasing detailed trim work and refined design throughout—this residence delivers sophistication and all-inclusive resort-style living in one of the area’s most desirable locations. Inside, soaring 18-foot vaulted ceilings and custom tray ceilings enhance the open-concept layout, while 12-foot full pocket sliders seamlessly connect indoor and outdoor living spaces. The living room is anchored by a sleek fireplace, creating a warm yet modern focal point. The chef’s kitchen is equipped with professional-grade gas appliances, a waterfall-edge quartz island, custom cabinetry, and an expansive butler’s pantry for effortless entertaining. A glass-enclosed wine display and tray ceiling details add dramatic appeal. The primary suite features 14-foot ceilings and a spa-inspired bath with a freestanding soaking tub, dual vanities, and a luxurious walk-in shower. All bedrooms include custom California Closets. A designated large office, spacious laundry room, and private gym complete the interior amenities. The home also has a full security system installed. Outdoors, the resort-style backyard showcases a heated saltwater pool and hot tub spa with elegant water features. The back patio, finished with a Brazilian hardwood ceiling, is enhanced with remote-controlled mosquito blinds with sun protection for year-round comfort, as well as a full sound system that can be app controlled. A fully equipped outdoor kitchen, fire pit, and outdoor SunBrite TV create the ultimate entertaining space, while a private putt-putt golf course adds a one-of-a-kind touch to this exceptional property. Please let us know how we can help and give us a call to set up a tour of this beautiful home. Thank you.

1800 Webber Street, Sarasota

1647 Siesta Drive, Sarasota
$1,690,000
5 Beds ⋅ 3 Baths ⋅ Bayview SubDv. ⋅ 34239 Zip Code
Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,032 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings, natural light, and high-quality finishes throughout. The home features a modern and elegant kitchen with top-of-the-line Cafe' appliances, quartz countertops, and custom cabinetry. The primary bedroom located on the upper level can be accessed by elevator is a true sanctuary, offering a plush and peaceful retreat It boasts vaulted ceilings, en-suite bathroom that includes a soaking tub and a separate shower that's great for unwinding after a long day. The room also features a generously sized walk-in closet with abundant space for storage and organization as well as a private terrace. On the second floor you will find three vast bedrooms, with plenty of closet space for added convenience and comfort One of the most notable features of the second floor is the sizable sundeck and balcony, which are attached to both bedrooms. The laundry room is conveniently located on the second floor as well. The spacious bonus room offers endless possibilities, from an office, den, playroom, media center or a home gym. This home has two patios with an outdoor area with a large pool and hot tub that seamlessly blend the indoor and outdoor living with meticulously planned landscaping. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping in the area. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need.

1647 Siesta Drive, Sarasota

1875 Oleander Street, Sarasota
$2,395,000
3 Beds ⋅ 3 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Impeccably maintained and thoughtfully designed, this custom-built John Cannon home offers an inviting blend of timeless elegance, spacious interiors, and relaxed Florida living in Sarasota’s desirable West of Trail neighborhood. Set along beautiful, tree-lined Oleander Street adjacent to Cherokee Park, this residence welcomes you with an open floor plan and soaring 14-foot ceilings that create an immediate sense of space and light. The well-appointed kitchen features solid wood cabinetry, Bosch stainless steel appliances, and a breakfast bar with seating for four—ideal for casual dining and entertaining. The inviting family room, complete with a fireplace, overlooks the pool and patio, while pocketing sliding glass doors seamlessly connect indoor and outdoor living. A professionally painted mural gives the formal dining room a rich botanical backdrop infused with tropical elegance. There is a private office with built-in cabinetry providing a comfortable, dedicated workspace The expansive primary suite is a peaceful retreat, featuring dual walk-in closets, separate vanities, dual sinks, a jetted soaking tub, and a separate shower. Two additional bedrooms provide generous closet space, with one featuring an ensuite bath. Plantation shutters throughout enhance the home’s understated elegance and tropical ambiance. Outdoors, a gorgeous, screened pool and spa are surrounded by an expansive tiled patio and outdoor kitchen have abundant space for lounging, dining, and entertaining in the Florida sunshine. Practical amenities include a spacious laundry room with a sink and built-in cabinetry, plus an oversized two-car garage with workshop cabinetry and access to a large attic for additional storage. The location is equally appealing. Enjoy a short walk to Southside Elementary School and stroll a few blocks north to the boutiques, restaurants, and Morton's Gourmet Market in Southside Village. Sarasota Memorial Hospital, Downtown Sarasota, the Bayfront, and the area’s beautiful beaches are all conveniently accessible. Experience the elegance, comfort, and exceptional location of this West of Trail residence. Schedule your private showing today.

1875 Oleander Street, Sarasota

2420 Floyd Street, Sarasota
$2,190,000
5 Beds ⋅ 5 Baths ⋅ Rustic Lodge SubDv. ⋅ 34239 Zip Code
Introducing an exquisite New Construction, 3,356 sq. ft. with 5 bedrooms and 5 full bathrooms, home in the heart of Sarasota. Pool installation is in progress, with a projected completion of October. This stunning residence offers an unparalleled combination of luxurious comfort and unbeatable location, minutes from Downtown. As you enter this dazzling property, you will be greeted by an open and spacious floor plan that features high ceilings, natural light, and high quality finishes throughout. The home features an elegant kitchen with top-of-the-line Fulgor Milano appliances, quartz countertops, and custom cabinetry. Two patios with an outdoor kitchen and additional island seamlessly blend indoor and outdoor living and lush landscaping. The master bedroom of this gorgeous home is a true sanctuary, offering a plush and peaceful retreat after a long day. With a high-ceiling and large windows to let in unrestricted natural light, providing a bright and airy feel that's perfect for relaxation. The room also features two generously sized walk-in closets. The master bathroom is equally impressive, featuring a soaking tub and a separate shower that's great for unwinding after a long day. The opulent finishes and high-end materials used throughout the space add to the lavish feel of this spectacular master suite, making it the best place to recharge and rejuvenate. The home also features several storage closets, a large laundry room, and ample storage space with room to add an elevator. As you ascend the grand staircase to the upper level of the home, you are met with a second living room area, large balcony, and three cozy bedrooms with en-suite bathrooms. This setup is perfect for families or groups of friends looking to stay together in comfort and convenience. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping. The home is also a few minutes’ walk from Arlington Park’s tennis courts and more. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need. *There is some virtual staging imagery of the upcoming pool.

2420 Floyd Street, Sarasota

1240 Hillview Drive, Sarasota
$14,950,000
4 Beds ⋅ 4 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code
Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood paneled library, formal dining with 12-foot ceilings, and a wet bar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand-new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.

1240 Hillview Drive, Sarasota

2557 Temple Street, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Rustic Lodge SubDv. ⋅ 34239 Zip Code
Privacy and charm in the heart of Arlington Park, Sarasota, this thoughtfully updated bungalow offers tranquil luxury and optimal convenience. In one of the quietest sections of Sarasota, yet only six blocks from Sarasota Memorial Healthcare, a few more to Southside Village, and mere minutes to downtown and the exciting bayfront, this location is ideal. And, with the long list of amenities offered by the Arlington Park and Recreation Center just a hundred yards away, what more could you want? This home has been lovingly and thoughtfully updated over the past three years with new roof, windows and doors, kitchen, pool re-surfacing and equipment, and more. The split floor plan features an open-concept kitchen and entertaining area with a private primary suite that opens to the freshly screened pool area and lanai. The guest room is at the front of the home and includes its own full bath. Given its location, a study or in-home office could work well here too. Connecting the center of the home to the lanai and pool area is a beautiful transitional room, used as a dining and conversation space. Even the outdoor area has much to offer with new privacy fencing, gutters and downspouts, low-maintenance landscaping and lighting, green space for pets and extra off-street parking. For those who value optimized space, quiet and convenient location, the assurance of impact-rated windows and doors, and new in everything that matters most, this is your place!

2557 Temple Street, Sarasota

2375 Datura Street, Sarasota
$895,000
3 Beds ⋅ 3 Baths ⋅ Thompson Sub SubDv. ⋅ 34239 Zip Code
WHAT IF YOUR NEXT HOME FELT LIKE A PRIVATE TROPICAL RETREAT IN THE HEART OF SARASOTA? Welcome to The Tropical Hideaway, a beautifully updated 3-bedroom, 3-bath residence offering 1,859 square feet of living space on Datura Street, one of the most desirable residential streets in Arlington Park. Combining privacy, character, and modern comfort, this home offers an exceptional Sarasota lifestyle. Step inside and discover two inviting living areas, three beautifully remodeled bathrooms, new luxury vinyl plank flooring, crown and base moldings, recessed lighting, ceiling fans, and refreshed finishes throughout. The updated kitchen features newer appliances, soft-close shaker-style cabinetry, and granite countertops. Additional improvements include a 2018 roof, updated plumbing, recently relined sewer lines, PVC water pipes, and HVAC system updates. Beyond the interiors, your private tropical escape awaits. Situated on an approximately 9,000-square-foot lot, the property showcases lush landscaping, a welcoming front lanai, a fully enclosed backyard with wood privacy fencing, and a brand-new Jacuzzi surrounded by greenery. Enjoy peaceful mornings, outdoor entertaining, and exceptional privacy beneath the Florida sky. A covered carport adds everyday convenience. NO HOA OR CDD FEES! An outstanding opportunity for a primary residence, seasonal getaway, or investment property, with potential for short-term rentals with a minimum stay of seven full days and nights. Located within the Southside Elementary School attendance zone, and just minutes from Sarasota Memorial Hospital, Southside Village, Siesta Key, Downtown Sarasota, Lido Key, shopping, dining, recreational amenities, and beautiful Gulf Coast beaches. THE TROPICAL HIDEAWAY BRINGS TOGETHER LOCATION, PRIVACY, LIFESTYLE, AND OPPORTUNITY. Some homes are meant to be seen. Others are meant to be experienced. Schedule your private showing today!

2375 Datura Street, Sarasota

2089 Arlington Street, Sarasota
$2,650,000
4 Beds ⋅ 6 Baths ⋅ La Linda Terrace SubDv. ⋅ 34239 Zip Code
Brand-new construction and move-in ready! This custom contemporary residence offers 4,231 square feet of thoughtfully designed living space on a large corner lot outside a flood zone. Constructed of concrete block on both levels, the home combines modern architecture with a warm, comfortable feel and an exceptional level of craftsmanship throughout. Inside, soaring 22-foot ceilings, walls of custom glass, and abundant natural light create a dramatic yet inviting main living area. The Italian-designed kitchen features custom cabinetry, Sub-Zero appliances, luxury built-ins, a natural stone island with seating, and a concealed secondary kitchen ideal for entertaining and catered events. The first-floor primary suite is privately positioned and includes a spa-like bath. Three additional ensuite bedrooms are generously sized, each with a private balcony, while an office offers the flexibility to serve as a fifth bedroom. A custom glass-enclosed wine room and an upstairs media lounge overlooking the main living space add both function and architectural interest. Oversized sliding doors open the interior to a resort-style outdoor setting with a custom pool and spa, covered terrace, enhanced landscaping, and architectural exterior lighting. Additional features include three independent HVAC zones, a commercial-style elevator, spray-foam insulation, and custom windows, doors, and cabinetry throughout. Situated in the sought-after neighborhood of Arlington Park, the home is near Southside Village and just minutes from the shops and restaurants of downtown Sarasota and the bayfront, as well as the world-famous beaches of Siesta Key and Lido Key. Book your private showing today!

2089 Arlington Street, Sarasota

2630 Sunnybrook Drive, Sarasota
$825,000
3 Beds ⋅ 2 Baths ⋅ South Gate SubDv. ⋅ 34239 Zip Code
Welcome to South Gate, where oak-canopied streets, a short walk to Arlington Park, and a quick drive to downtown, Sarasota Memorial Hospital, and Siesta Key make everyday life easier. This 1956 stone-front ranch delivers what buyers in this neighborhood look for and rarely find together, original mid-century character, a private heated saltwater pool, three bedrooms and two baths plus a dedicated office, and impact windows and storm shutters for peace of mind every season. From the herringbone brick paver drive to the fresh tropical landscaping, the home makes a strong first impression. Inside, original terrazzo floors run through the living areas and bedrooms, the kind of authentic 1950s detail that is increasingly hard to find. The living room centers on a painted Ocala block feature wall and a full wall of built-in cabinetry and shelving with an integrated desk, giving you real storage and a place for everything. Oversized front windows keep the room bright, and the adjoining dining room looks directly out at the pool’s rock waterfall. The kitchen is where this home earns its keep. Solid cherry cabinetry with glass-front uppers, stone counters, a stainless tile backsplash, a chimney-style hood, a built-in wall oven and microwave, and updated stainless steel appliances give a serious cook everything they need. The long curved island with a prep sink seats a crowd, so guests stay part of the conversation while you cook. Slate floors carry into a breakfast nook where French doors open to the screened lanai, making it easy to move a gathering outside. The primary suite offers two closets and an updated bath featuring a glass-enclosed walk-in shower with a built-in bench, river pebble floor, and pebble accent niche. Two guest bedrooms share a modern hall bath with a double vanity. The office sits on the opposite side of the home from the bedrooms with its own door to the pool deck, so working from home stays quiet and feels like a break, and it converts easily to a guest room when family visits. Select furnishings are available with the sale, so the home can be ready to enjoy from the day you move in. The backyard is designed for the way Sarasota is meant to be lived. Relax in the screened lanai with its natural stone wall and ceiling fan, then step out to a fully fenced yard wrapped in mature palms and tropical plantings that create genuine privacy. A freeform heated saltwater pool with stone coping and a cascading rock waterfall is ready for evening swims year round, and low-maintenance turf means your weekends go to enjoying the yard, not mowing it. A patio dining area and two-car garage round out the home. With a voluntary neighborhood association instead of a mandatory HOA, and zoning for Southside Elementary and Sarasota High School, this is a South Gate home that works for how you live now and for years ahead. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2630 Sunnybrook Drive, Sarasota

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