Sarasota/Pinecraft Homes with Pool Community Features

Sarasota/Pinecraft Homes with Pool Community Features

Welcome to the enchanting community of Sarasota, specifically the delightful neighborhood of Pinecraft, where sunshine, serenity, and a sense of community blend seamlessly. Nestled in the heart of Sarasota County, this charming area is renowned for its unique atmosphere, showcasing a rich tapestry of cultural influences and a vibrant lifestyle that appeals to residents and visitors alike.

Pinecraft is characterized by its picturesque streets lined with swaying palm trees and the warm, inviting ambiance that comes with year-round Florida sunshine. This quaint neighborhood is particularly popular among those seeking a slower pace of life, with its close-knit community feel and an array of local amenities that cater to all needs. Enjoy leisurely strolls to nearby shops, indulge in delicious dining options, or participate in community events that foster connections among neighbors.

One of the standout features of homes in Pinecraft is the abundance of properties with private pools. Imagine lounging by your own sparkling oasis, surrounded by lush landscaping, where you can unwind after a long day or entertain friends and family under the sun. These homes not only provide a refreshing escape from the Florida heat but also enhance the overall lifestyle, making it easy to host gatherings or simply enjoy quiet moments of relaxation.

With its perfect blend of community spirit, beautiful surroundings, and the allure of poolside living, Pinecraft in Sarasota is truly a hidden gem waiting to be explored. Whether you're looking for a permanent residence or a seasonal retreat, this enchanting neighborhood promises to be a place you’ll love to call home.

Newest Sarasota/Pinecraft Homes with Pool Community Features

$725,000
4 Beds ⋅ 4 Baths ⋅ Arlington Park SubDv. ⋅ 34239 Zip Code
Virtually Staged. Ideally located across the street from Arlington Park, this renovated 4-bedroom, 3.5-bath home sits on an oversized corner lot of nearly 13,000 square feet, offering exceptional space, privacy, and flexibility, with plenty of room to add a guest house, a pool, or both! Inside, new luxury vinyl flooring runs throughout the open floor plan, complementing the home’s thoughtful modern updates. The renovated chef’s kitchen features Shaker-style cabinetry with custom storage, oiled cherry butcher-block and charcoal quartz countertops, two refrigerators, two sinks, a gas range, and updated pendant and under-cabinet lighting. Each bedroom includes an en-suite bath, while an enclosed lanai off the kitchen provides additional air-conditioned living space with its own Mitsubishi mini-split system. The lanai overlooks a deep, private backyard surrounded by mature trees, tropical landscaping, flowering plants, and pond with a stone waterfall. Additional features include a newly roofed 12-by-18-foot hobby shed, a one-car garage, and a rear carport, providing flexible storage for vehicles, a boat, or recreational equipment. Just steps from the front door, Arlington Park offers swimming pools, tennis and basketball courts, playground, fitness area, walking trail, and a dog park. The home is located within the Southside Elementary school district and just minutes from Downtown Sarasota, the Bayfront, Legacy Trail, Selby Gardens, St. Armand's Circle, and Siesta Key. No HOA fees or deed restrictions. Call us today for your private showing.

2000 Craft Lane, Sarasota
$265,000
2 Beds ⋅ 2 Baths ⋅ Bermuda On Osprey SubDv. ⋅ 34239 Zip Code
Turnkey investment opportunity in a prime Sarasota location! Beautifully renovated two-bedroom, two-bath second-floor condominium in Oasis on Osprey, just minutes from Southside Village, Siesta Key, downtown Sarasota, shopping, dining and area attractions. Flexible rental policies add strong appeal for investors seeking income-producing potential, while the move-in-ready condition minimizes upfront renovation costs. The unit features new luxury plank flooring, fresh paint and a beautifully updated kitchen with granite countertops, refrigerator, M/W, dishwasher, and LG range with convection and built-in air fryer. The open great room leads to a screened-in lanai, and both spacious bedrooms offer new ceiling fans, modern double-hung windows and custom blinds. The primary suite includes a private en-suite bath and access to the screened lanai. HVAC replaced in 2024 and water heater replaced in 2025. Oasis on Osprey offers a newly renovated pool, fitness center, updated laundry facility with all new equipment, elevator access, assigned parking, guest parking and private lockable storage. An excellent opportunity for a rental property, second home or Sarasota investment with major updates already completed. Turnkey, low-maintenance and ready to potentially generate income from day one!

3360 S Osprey Avenue Unit 209B, Sarasota
$200,000
2 Beds ⋅ 2 Baths ⋅ Village Green SubDv. ⋅ 34239 Zip Code
Whether you’re looking for a year-round home or a seasonal escape, this 2-bedroom, 2-bath home in Village Green offers a spacious layout, an expansive Florida room, and a community pool just steps from your back door. Inside, the living and dining areas are open and filled with natural light, with wide sliding glass doors extending both spaces into the Florida room. The kitchen features granite countertops, extensive cabinetry, a breakfast area, and an open connection to the living and dining areas. Stretching across the rear of the home, the Florida room is lined with windows overlooking the green space, with room for a second sitting area, card table, hobby space, or a quiet place to read with your morning coffee. The primary bedroom includes an en suite bathroom, while the second bedroom and full bathroom provide comfortable space for guests or a home office. A dedicated laundry room, private covered carport, included cable, and grounds maintenance add convenience to everyday life. Outside, the community pool and surrounding green space provide even more to enjoy, whether spending an afternoon poolside, catching up with neighbors, enjoying the Florida sunshine, or taking in the view from home. Village Green is an established 55+ community close to Sarasota’s restaurants, shopping, and golf courses, with downtown Sarasota, St. Armands Circle, and the white-sand beaches of Siesta Key and Lido Key all within easy reach.

3262 Brockton Lane Unit 608, Sarasota
$239,900
2 Beds ⋅ 2 Baths ⋅ South Gate Village Green SubDv. ⋅ 34239 Zip Code
Ready to retire in Sarasota? Welcome to Village Green in South Gate—truly the heart of Sarasota. LESS THAN 10 MINUTES TO SIESTA KEY, DOWNTOWN SARASOTA, AND THE HIGHWAY, PLUS JUST 15 MINUTES TO THE AIRPORT AND UTC, this location puts you right in the center of it all while still enjoying a peaceful 55+ lifestyle. BRAND NEW HVAC (that is Heating and Cooling) put in this week! It comes with a transferable warranty. In addition an ULTRAVIOLET sensor was added to insure a mold free home. THIS HOME HAS NEVER FLOODED! It offers A NEW CERAMIC TILE ROOF with a 50 YEAR TRANSFERABLE WARRANTY on the tiles, a 35K value for the title roof plus a 10K value for the flat roof!! That is a 45K VALUE setting you up for low-maintenance living for years to come. This is ONE OF THE LARGEST VILLAS IN THE COMMUNITY, featuring a TRUE OVERSIZED LAUNDRY ROOM. NEW FLOORING throughout. Abundant STORAGE. The updated kitchen is a showstopper with STAINLESS STEEL APPLIANCES AND QUARTZ COUNTERTOPS, plus TONS OF COUNTER SPACE and a spacious layout that makes cooking and entertaining a dream. There is AN EAT-IN KITCHEN AREA PLUS A FORMAL DINING SPACE, offering flexibility for everyday living and hosting. The OPEN-CONCEPT LIVING ROOM IS FILLED WITH NATURAL LIGHT, creating a bright and welcoming feel. Just off the living area is a FLORIDA ROOM OVERLOOKING THE COMMUNITY POOL, perfect for a home office, craft room, or extra lounge space, along with A SCREENED-IN LANAI so you can enjoy the Florida sunshine bug-free. The TWO SPACIOUS BEDROOMS ARE LOCATED DOWN A SEPARATE HALLWAY FOR PRIVACY AND QUIET. A true PRIMARY SUIT with WALK In CLOSET. With TWO FULL BATHROOMS—ONE WITH A WALK-IN SHOWER AND THE OTHER WITH A TUB— you have the best of both worlds. HURRICANE-GRADE WINDOWS IN THE MAIN LIVING AREAS add peace of mind, and if you’ve been wanting a garage, THE CARPORT IS READY—JUST ADD A DOOR. Step outside and the COMMUNITY POOL IS PRACTICALLY IN YOUR BACKYARD, feeling like your own private oasis. Enjoy a LOW-MAINTENANCE LIFESTYLE WITH GROUNDS MAINTENANCE INCLUDED, a WELL-FUNDED COMMUNITY. Building INSURANCE IS INCLUDED in this HOA unlike surrounding units, a $3600 VALUE A YEAR! Along with yearly ROOF CLEANING preserving the life of your roof and reserves for private road repairs. VILLAGE GREEN GOLF CLUB JUST STEPS AWAY for the golf enthusiast. Seller is open to giving a credit for garage door upon acceptable offer. This is Sarasota 55+ living at its best—schedule your private showing today.

3286 Brunswick Lane Unit 704, Sarasota
$649,900
3 Beds ⋅ 2 Baths ⋅ South Gate SubDv. ⋅ 34239 Zip Code
LOCATION, LOCATION, LOCATION! Welcome to this charming South Gate pool home, ideally situated on a quiet street just minutes from Sarasota Memorial Hospital, Downtown Sarasota, shopping, dining, schools and world-famous Siesta Key Beach. Set on a generous quarter-acre lot, this property offers a wonderful combination of location, privacy, character and Florida outdoor living with plenty of opportunity to make it your own. The true showstopper is the private backyard tropical oasis, surrounded by lush mature landscaping and mango trees. At the heart of the outdoor space is a stunning free-form saltwater pool, renovated in 2015, surrounded by an expansive travertine pool deck perfect for relaxing, entertaining and enjoying the Florida sunshine year-round. The fully fenced backyard provides exceptional privacy and plenty of room for gatherings, gardening or simply unwinding in your own tropical retreat. Inside the home is filled with character and distinctive architectural details. A dramatic floor-to-ceiling Coral Keystone wood-burning fireplace anchors the living room, while beautifully restored terrazzo flooring flows through the living room, dining room, kitchen and hallways. All three bedrooms feature warm wood flooring. The kitchen offers solid-surface countertops, stainless steel appliances, a skylight and a charming garden window overlooking the courtyard entry and established herb garden. Additional features include thermal-pane windows, two tankless water heaters and a convenient interior laundry room. The second bathroom, added in 2017, features an interior sink and toilet and also functions as a convenient pool bath with an outdoor shower. The third bedroom currently does not have a closet but can easily be converted back, offering flexibility for use as a bedroom, home office or den. An oversized two-car garage provides excellent storage and includes a dedicated 7' x 7' workshop area. Additional improvements include a full reroof in 2017, AC replacement in 2024, new 4-inch PVC sewer piping from the home to the Air Vac tap and fresh interior paint in the living room, dining room and kitchen. With its generous lot, established tropical setting, private saltwater pool and highly desirable South Gate location, this home offers something increasingly difficult to find, a property that can be enjoyed today while still providing the opportunity to update and make it uniquely your own. Whether you're relaxing poolside beneath the mature landscaping, entertaining friends in the expansive backyard or enjoying convenient access to Sarasota's beaches, downtown and everyday amenities, 3536 Jaffa Drive is ready for its next chapter. Schedule your private showing today!

3536 Jaffa Drive, Sarasota
$249,000
2 Beds ⋅ 2 Baths ⋅ South Gate Village Green SubDv. ⋅ 34239 Zip Code
Welcome to 3289 Fairhaven Lane. Discover this stunning and serene condo that perfectly blends comfort, style and a modern, inviting atmosphere. Nestled in the heart of Bee Ridge, Sarasota, Florida this home offers a spacious layout and thoughtful upgrades for a truly enjoyable lifestyle and one floor living. This beautifully maintained property features 2 spacious bedrooms, 2 bathrooms, and 1,470 square feet of elegant living space designed for comfort and relaxation. Property Highlights: • Spacious Living: A large primary suite features a well-appointed walk-in closet, while the lovely guest room includes a bright and airy guest bathroom. • Convenience & Comfort: Laundry is conveniently located near the kitchen, and an attached one-car garage adds extra ease to daily living. • Relaxing Spaces: Enjoy your morning coffee by the gorgeous hand-tiled fireplace (electric) or unwind on the expansive lanai, featuring new flooring and incredible natural light. •Tile Roof Replaced in 2020 with transferable Warranty • Resort-Style Amenities: Step out your back door to the sparkling pool, ideal for relaxing afternoons or entertaining friends. • Fresh Updates: With brand-new flooring, appliances, and fresh paint, this home is move-in ready and boasts a modern touch. • Prime Location: Situated just 6 miles from the award-winning Siesta Key Beach, you’ll have easy access to Sarasota’s vibrant dining, shopping, and cultural attractions. Additional Note: This property has sustained no damage from recent hurricanes, ensuring peace of mind for new homeowners. Embrace the vibrant Florida Gulf Coast lifestyle in this unusually spacious and elegant residence. With its fresh updates and resort-style living, this home invites you to experience the ultimate in comfort and convenience. Live the Sarasota lifestyle. Don’t miss out on this exceptional opportunity—schedule your tour today!

3289 Fairhaven Lane Unit 112, Sarasota
$215,000
2 Beds ⋅ 2 Baths ⋅ South Gate Village Green SubDv. ⋅ 34239 Zip Code
Great DEAL NEW PRICE!! AS_IS South Gate Village Green! Here is the opportunity you have been waiting for in this attractive 55+ community. This 2BR/2BA Villa would make a perfect Winter Retreat or also could bel as a full time residence !! An A/C Florida room and office area provide an additional 350+ sq. ft.! This villa is located on a quiet cul-de-sac and overlooks the Community Pool and Green area! Very well Maintained Home. The updated kitchen which offers a closet pantry and lots of cabinets for storage as well as a Dinette. The inside laundry room is a plus and additional storage. Garage is Enclosed with Extra Storage too! Village Green is ideally situated and only minutes from all of your shopping needs, fine restaurants and nearby golf courses. The Par 3 Village Green Golf course is minutes away and great practice for your short game at a very reasonable price! Only a short drive to the downtown area and the #1 beach Siesta Key!! ((Also Available for Rent Yearly in MLS ))

3276 Brunswick Lane Unit 705, Sarasota
$380,000
2 Beds ⋅ 2 Baths ⋅ South Gate Manor SubDv. ⋅ 34239 Zip Code
Welcome to 2915 Webber Street, where comfort, flexibility, and location come together in the heart of Sarasota. This move-in-ready home features an updated kitchen with modern cabinetry, granite countertops, and a functional layout that’s perfect for everyday living and entertaining. A spacious flex room offers the ideal home office, playroom, or can be easily converted into a true third bedroom to meet your needs. Step outside to the oversized, fully fenced backyard with endless possibilities. With plenty of room for a custom pool, outdoor kitchen, or lush tropical landscaping, you can create the backyard oasis you’ve always envisioned. Ideally located just minutes from vibrant Downtown Sarasota and approximately 6 miles from world-renowned Siesta Key Beach, you’ll enjoy quick access to award-winning beaches, shopping, dining, parks, and cultural attractions while still being tucked away in an established neighborhood. Whether you’re searching for a primary residence, seasonal retreat, or investment opportunity, this centrally located home offers exceptional value, versatility, and the best of the Sarasota lifestyle.

2915 Webber Street, Sarasota
$560,000
3 Beds ⋅ 2 Baths ⋅ Arlington Park SubDv. ⋅ 34239 Zip Code
BACK ON THE MARKET DUE SOLELY TO BUYER FINANCING. Ideally just one block from Arlington Park, this thoughtfully reimagined Tropical Mid-Century Bauhaus residence captures the effortless Sarasota lifestyle so many dream about. Filled with natural light, the inviting split-bedroom floor plan offers three generously sized bedrooms, two beautifully renovated baths, luxury vinyl plank flooring throughout, and an open kitchen that naturally becomes the heart of the home, flowing seamlessly into comfortable living and entertaining spaces. Walls of windows blur the line between indoors and out, creating a bright, cheerful atmosphere that immediately feels like home. Set on an oversized homesite, the expansive backyard offers abundant space to create the resort-style pool you've always imagined while providing generous room for outdoor dining, entertaining, gardening, pets or play. A detached studio invites endless possibilities as a yoga retreat, art studio, fitness room, workshop, or private creative space. Recent updates provide added value and peace of mind, including a new roof (2024), four year old HVAC, and a full suite of Whirlpool kitchen appliances that are approximately 2½ years old. To preserve the home's clean Bauhaus architecture, the roof vents were thoughtfully relocated to the rear of the home. Offered turnkey furnished, this exceptional residence is ready for you to unpack, unwind and begin enjoying everything Sarasota has to offer from the moment you arrive. Arlington Park is one of Sarasota's treasured neighborhoods, featuring a heated lap pool, aquatic center, tennis and pickleball courts, basketball courts, playground, dog park, recreational trails, outdoor fitness areas and expansive green spaces just a short distance away. Ideally minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, Siesta Key Beach, exceptional dining, boutique shopping, and Sarasota's renowned arts and cultural attractions, you'll enjoy the ideal balance of relaxation, recreation and convenience. The neighborhood continues to flourish with underground electric utilities planned throughout the area and striking new homes completed and under construction nearby, underscoring the enduring desirability and long-term value of this sought-after location. Whether you're searching for a full-time residence, seasonal escape or investment in one of Sarasota's vibrant neighborhoods, this is a rare opportunity to own a beautifully updated architectural home on an oversized lot where timeless design, modern comfort and an exceptional lifestyle come together. Schedule your private showing today and discover why so many buyers fall in love with Arlington Park.

2719 Temple Street, Sarasota
$258,000
2 Beds ⋅ 2 Baths ⋅ Orchid Oaks SubDv. ⋅ 34239 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in the highly sought-after Orchid Oaks community. This spacious, wheelchair-accessible ground-floor residence combines comfort, convenience, and peace of mind, making it the perfect place to call home. Designed for long-term peace of mind, this home includes hurricane-impact windows, upgraded plumbing and electrical systems, a newer AC system and water heater, and the added benefit of being elevated above flood level. One of the standout features of this unit is its exceptional accessibility. The assigned carport is the very first parking space directly in front of the condo, making unloading groceries, luggage, or everyday essentials incredibly easy. With no stairs to navigate, this home offers effortless living for all. Inside, you'll find 1,365 square feet of thoughtfully updated living space featuring luxury vinyl plank flooring throughout and an open-concept floor plan filled with natural light. The remodeled kitchen boasts modern appliances, generous counter space, and abundant cabinetry, while both bathrooms have been tastefully renovated with contemporary finishes and fixtures. Enjoy your morning coffee or unwind in the evening on the screened lanai overlooking peaceful Phillippi Creek—a tranquil setting just minutes from Sarasota's renowned shopping, dining, and Gulf Coast beaches. Additional features include: Spacious primary suite with updated, spacious en-suite bathroom, Luxury vinyl plank flooring throughout, Pet friendly community with nearby dog park and Community walking paths. Condo fees include clubhouse, pool, insurance, exterior maintenance, pest control, water, sewer and trash! Located in the desirable Orchid Oaks community, this move-in-ready condo offers low-maintenance living in an ideal Sarasota location. Whether you're looking for a full-time residence or a seasonal retreat, this beautifully updated home is ready for you to move in and enjoy.

2753 Orchid Oaks Drive Unit 104, Sarasota
$159,500
2 Beds ⋅ 1 Baths ⋅ Sunland Apts SubDv. ⋅ 34239 Zip Code
Virtually Staged. GREAT LOCATION for Seasonal or Full time 55+ Residents. Just minutes from downtown Sarasota & a straight drive to Siesta Keys world-famous beaches. Interior completely remodeled, designed the Kitchen with an open layout with Quartz Countertops, custom white cabinets, & SS Appliances. Bathroom got a complete makeover. New Luxury Vinyl flooring throughout, new modern interior Doors, Fans & Lighting. Community Pool, Laundry facilities & storage space for each unit. Walk to Dining, Shopping & CMX Cinemas/Bistro. Low HOA Monthly Fee.

3755 S School Avenue Unit 54, Sarasota
$869,000
3 Beds ⋅ 3 Baths ⋅ South Gate SubDv. ⋅ 34239 Zip Code
A beautifully reimagined South Gate residence, this 3 bedroom, 3 bathroom home blends modern sophistication with timeless Sarasota charm. Set on an elevated 14,005 sq ft corner lot, the property offers exceptional privacy, mature landscaping, and an abundance of fruit-bearing trees, all supported by an irrigation system. Inside, the split floor plan provides effortless livability, complemented by a dedicated private office and an additional bonus room ideal for flexible lifestyle needs. Two of the bedrooms are ensuite, creating comfortable retreats for family or guests. The heart of the home is the gourmet kitchen, featuring 42" cabinetry, quartz countertops, stainless steel appliances, and a large picture window that fills the space with natural light. The adjoining dining area offers generous room for gatherings, while the family room with its sleek electric fireplace creates a warm, inviting atmosphere. Thoughtful upgrades continue throughout: a totally renovated interior, and an oversized two-car garage with epoxy flooring. Outside, a paver circular drive and a charming covered front porch with new Trex decking elevate curb appeal. With its expansive lot, there is ample room to add a pool and create a true Sarasota oasis. Located in the coveted South Gate community, this home offers unmatched convenience just minutes to fine dining, boutique shopping, world renowned beaches, and vibrant downtown Sarasota.

2465 Foster Lane, Sarasota
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