Osprey Homes with Rain Gutters Exterior Features

Osprey Homes with Rain Gutters Exterior Features

Welcome to Osprey, Florida, a charming gem nestled in Sarasota County, where coastal beauty meets a vibrant community spirit. This quaint town is perfectly situated between the serene Gulf of Mexico and the bustling city of Sarasota, making it a prime location for those seeking a blend of tranquility and excitement. Osprey boasts stunning waterfront views, lush parks, and a rich history that invites exploration and appreciation.

As you stroll through the picturesque neighborhoods, you’ll discover a variety of homes that embody the essence of Florida living. Many of these residences feature thoughtful exterior details, such as rain gutters, which not only enhance the aesthetic appeal but also provide practical benefits. Rain gutters are essential for protecting your home from water damage, guiding rainwater away from your foundation, and ensuring that your outdoor spaces remain beautiful and functional.

The homes in Osprey exemplify a seamless integration of style and sustainability. With options ranging from charming bungalows to luxurious waterfront estates, there’s something for everyone in this inviting community. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by lush landscaping, all while knowing that your home is equipped to handle Florida’s seasonal rains.

Osprey is not just a place to live; it’s a lifestyle. With its close proximity to stunning beaches, top-notch dining, and cultural attractions, you’ll find that every day offers new adventures. Whether you’re looking to buy your first home or seeking a serene retreat, Osprey welcomes you with open arms and endless possibilities. Come discover the magic of Osprey, where your dream home awaits!

Newest Osprey Homes with Rain Gutters Exterior Features

$2,175,000
4 Beds 4 Baths The Oaks SubDv. 34229 Zip Code
Located behind the gates of The Oaks Clubside, and just moments from the clubhouse, this 3 bedroom plus office, 4.5 bath home offers over 3,500 square feet of quiet elegance and beautifully updated living space. Set along the 4th hole of the Eagle Course, the property enjoys sweeping golf and lake views, along with the community’s signature bridge, adding a picturesque focal point to the landscape. Inside, the formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The beautifully updated kitchen has been redesigned with modern finishes and generous workspace providing both style and functionality for everyday living. It opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus there is a formal dining room and breakfast bar for flexible entertaining. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located 3rd bathroom. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. With no house on one side, this exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership. There is currently NO WAITING LIST for either Golf or Sports/Social membership.

362 Macewen Drive, Osprey

$2,199,999
4 Beds 4 Baths Southbay Yacht & Racquet Club SubDv. 34229 Zip Code
Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

154 Lookout Point Drive, Osprey

$1,100,000
4 Beds 3 Baths Rivendell The Woodlands SubDv. 34229 Zip Code
Luxury Living in Rivendell Woodlands Welcome to this exceptional 3,984-square-foot estate in the highly sought-after Rivendell Woodlands community, where luxury, comfort, and convenience come together in a spectacular lakefront and preserve setting. Built in 2003, this meticulously maintained residence offers 4 bedrooms, 3 baths, a private office/den, expansive bonus room, formal living and dining rooms, and a family room, providing abundant space for both everyday living and entertaining. The thoughtfully designed floor plan features a dedicated den on the first floor complete with a Murphy bed. The primary suite on 2nd floor features tray ceiling, custom his-and-her walk-in closets and seating area, and sliders to the covered, screened porch stretching the full length of the home with incredible water and preserve views. Plantation shutters are throughout, with remote-controlled blinds for the patio sliders. The chef's kitchen is enhanced by a reverse-osmosis water system and large wine and beverage fridge, while a whole-house water softener and dual air-conditioning systems equipped with air-scrubber filtration devices ensure maximum comfort and efficiency. Step outside to your private resort-style oasis featuring a sparkling saltwater pool overlooking tranquil lake and preserve views. The outdoor living area is an entertainer's dream, complete with a fully equipped outdoor kitchen featuring a bar height counter framing the cooking areas, dual-tap built-in kegerator, Big Green Egg, and gas grill. Enjoy year-round relaxation from the screened covered lanai or retreat to the second-floor screened balcony to take in breathtaking views. For added peace of mind, second-floor sliding doors and windows are impact-resistant as well as the first floor southeast windows and shutters for all others. Additional upgrades include a new tile roof, newer a/c’s and water heater, extended paver driveway, epoxy-coated 3-car garage, well-water irrigation system, and outdoor generator electrical connection. Ideally located within nearby Pine View School, consistently ranked among the top schools in Florida and the nation, this remarkable property offers an unparalleled lifestyle in one of Sarasota County's most desirable communities. Experience the perfect blend of elegance, functionality, and Florida outdoor living in this extraordinary Rivendell Woodlands home.

907 Eagle Isle Court, Osprey

$695,000
3 Beds 3 Baths Blackburn Point Woods SubDv. 34229 Zip Code
Ideally located to enjoy all that Sarasota, Venice and Casey Key has to offer, this superbly remodeled maintenance-free home offers more than 2,800 square feet of thoughtfully redesigned living space and lives comfortably like a private, stand-alone residence. Nestled within an intimate enclave of just 44 homes, this property offers the ultimate lock-and-leave lifestyle, with the HOA taking care of exterior building maintenance, roof and landscaping. Professionally redesigned this year, the kitchen and bathrooms are complemented by numerous upgrades throughout the home. In the main living area, a soaring cathedral ceiling with wood-plank detailing creates a warm, sophisticated focal point. The home offers two spacious primary suites, each with an ensuite bath—one on the main level for convenience and one upstairs for added privacy. A third upstairs bedroom or flex room adds versatility, while the main-level office provides an ideal space for working from home or enjoying hobbies. The generous main living area flows seamlessly into an additional spacious family room in the loft, providing plenty of room for both everyday living and entertaining. Step out to the expansive glassed-in lanai, where a peaceful preserve backdrop creates a private tropical setting framed by mature palms, bamboo, and lush Florida greenery. An attached two-car garage adds everyday convenience. Residents also enjoy access to the amenities of the adjacent Pine Run community, including a large, heated pool and clubhouse, fitness room, tennis courts, and pickleball courts. With its extensive recent updates, flexible floor plan, beautiful preserve setting, and exceptional maintenance-free lifestyle, this is a rare opportunity to enjoy relaxed Sarasota living in a truly special home.

264 Woods Point Road Unit 264, Osprey

$824,900
4 Beds 3 Baths Park Trace Estates SubDv. 34229 Zip Code
Back on the market — this is a new opportunity to own this beautiful home. The previous contract fell through, and the property has successfully passed all inspections and appraisal. It is ready for a quick and smooth closing. MODERN COASTAL MASTERPIECE | OVER $200,000 IN LUXURY UPGRADES | NEW ROOF | HEATED SALTWATER POOL | PINE VIEW SCHOOL DISTRICT.Welcome to one of Park Trace Estates’ finest fully renovated homes, where sophisticated design, exceptional craftsmanship, and the Florida lifestyle come together in perfect harmony. This spectacular 4-bedroom, 3-bath residence has been extensively remodeled with over $200,000 in premium upgrades, creating a truly move-in-ready luxury retreat. From the moment you arrive, you’ll be captivated by the home’s outstanding curb appeal, featuring professionally designed tropical landscaping, an elegant paver walkway, and a welcoming entrance that immediately sets the tone for what’s inside. Step through the front door into a breathtaking open-concept floor plan showcasing soaring ceilings with custom decorative beams, an impressive floor-to-ceiling designer stone fireplace, abundant natural light, and exquisite designer finishes throughout. Every detail has been carefully selected to create a warm, elegant, and timeless coastal living experience. The heart of the home is the stunning chef’s kitchen, completely redesigned with premium finishes, featuring Bosch stainless steel appliances, oversized quartz countertops, custom cabinetry, and an expansive island perfect for entertaining family and friends. The spacious split-bedroom floor plan offers privacy and comfort, while three beautifully remodeled designer bathrooms provide a spa-like experience with luxury finishes and exceptional attention to detail.Expansive sliding glass doors seamlessly blend indoor and outdoor living, opening to your own private resort-style courtyard featuring a heated saltwater pool and spa, creating the perfect setting for entertaining or simply enjoying Florida’s year-round sunshine. Extensive Premium Improvements Include: ? NEW $60,000 Tile Roof ? NEW High-Efficiency HVAC System (2024) ? Completely Remodeled Designer Kitchen ? Premium Bosch Stainless Steel Appliances ? Oversized Quartz Countertops & Custom Cabinetry ? NEW Luxury Vinyl Flooring Throughout ? Three Fully Remodeled Designer Bathrooms ? Custom Floor-to-Ceiling Stone Fireplace ? Decorative Custom Ceiling Beams ? Freshly Painted Interior Throughout ? Freshly Painted Exterior ? Professionally Designed Custom Accent Walls with Premium Designer Finishes ? NEWER Saltwater Pool System ? Aqua Whole-House Water Filtration System ? Water Softener ? NEW Vinyl Privacy Fence v Custom-designed green wall at the patio and at the entrance. ? Professionally Designed Tropical Landscaping (Approx. $20,000) Located in the highly desirable Park Trace Estates, this exceptional property is just minutes from world-famous Siesta Key Beach, Nokomis Beach, the award-winning Pine View School, Legacy Trail and the natural beauty of Oscar Scherer State Park. Situated in Flood Zone X, this meticulously upgraded residence offers peace of mind, luxury, and an unbeatable location. This is more than a home—it’s a lifestyle. Every room reflects quality, craftsmanship, and thoughtful design. With over $200,000 invested in premium upgrades, this exceptional property is truly one of the finest opportunities currently available in Park Trace Estates.

Osprey

$1,770,000
3 Beds 2 Baths Southbay Yacht & Racquet Club SubDv. 34229 Zip Code
Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

206 Four Knot Lane, Osprey

$3,295,000
3 Beds 5 Baths Sorrento Shores SubDv. 34229 Zip Code
**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level entails an additional nonconforming bedroom, bathroom and recreation room with access to outdoor patio. 4-Car Garage plus extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.

135 Tina Island Drive, Osprey

$798,000
3 Beds 4 Baths Blackburn Harbor SubDv. 34229 Zip Code
One or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.

6100 Jessie Harbor Drive Unit 202, Osprey

$5,999,999
4 Beds 5 Baths Southbay Yacht & Racquet Club SubDv. 34229 Zip Code
Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.

313 Lookout Point Drive, Osprey

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