Osprey Homes with Two Story Property Description

Osprey Homes with Two Story Property Description

Welcome to Osprey, Florida – a hidden gem nestled in the heart of Sarasota County. This charming coastal town seamlessly blends the allure of small-town living with the vibrant culture of nearby Sarasota. Known for its picturesque landscapes, Osprey boasts stunning waterfront views, lush parks, and a plethora of outdoor activities, making it an ideal destination for families, retirees, and anyone seeking a serene slice of paradise.

Osprey is particularly renowned for its rich history and natural beauty, featuring the breathtaking Oscar Scherer State Park, where residents can enjoy hiking, biking, and birdwatching amidst the native flora and fauna. The nearby Nokomis Beach offers sun-soaked shores and tranquil waters, perfect for a day of relaxation or water sports. With a variety of dining options, boutique shops, and cultural attractions, Osprey provides a delightful lifestyle for its residents.

When it comes to real estate, Osprey offers a diverse selection of homes, including stunning two-story properties that cater to modern living. These spacious homes often feature open floor plans, gourmet kitchens, and expansive outdoor spaces, ideal for entertaining and enjoying the beautiful Florida weather. With ample room for families to grow and thrive, two-story homes in Osprey are designed to meet the needs of today’s homeowners while providing a comfortable and inviting atmosphere.

Whether you're looking to invest in a family home or seeking a tranquil retreat, Osprey’s two-story properties are a perfect choice. Embrace the charm of this coastal town and discover your dream home in Osprey today!

Newest Osprey Homes with Two Story Property Description

$1,399,000
4 Beds 4 Baths Southbay Yacht & Racquet Club SubDv. 34229 Zip Code
Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, 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

$319,000
2 Beds 3 Baths Towns-End Shores SubDv. 34229 Zip Code
This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while the second bedroom offers flexibility for guests, an office, or additional living space. Located in flood zone X, the oversized garage offers the perfect opportunity to add to your living space or provides an abundance of storage. The private outdoor spaces are a true highlight of the home. The beautifully landscaped yard and garden create a peaceful retreat, while the private terrace provides an ideal setting for al fresco dining and entertaining. A mature specimen lemon tree serves as the star of the garden, providing fresh lemons for lemonade, cooking, or homemade limoncello. Residents also enjoy access to the community pool, adding to the relaxed, resort-like feel of the property. The location is equally appealing. Situated in Osprey, the property is conveniently located near the beaches of Casey Key, local shops, restaurants, and a variety of recreational amenities directly across the street from Oscar Scherer State Park, home to over 17 miles of trails and nearly 1400 acres of natural habitats, launch a kayak, or simply take in the peaceful surroundings along the water. The nearby Casey Key Resort offers the opportunity to enjoy its pool, facilities, and restaurant for the day, providing an additional resort-style experience close to home. Downtown Sarasota and downtown Venice are also easily accessible, offering an outstanding selection of dining, shopping, cultural attractions, and entertainment. With its private outdoor spaces, community pool, beautiful natural light, and convenient location, this exceptional townhome offers a refined yet relaxed approach to coastal Florida living. Whether enjoyed as a full-time residence or a seasonal retreat, this home offers an exceptional opportunity to embrace the Florida lifestyle.

1819 Highland Road, Osprey

$540,000
3 Beds 3 Baths Blackburn Point Marina Village SubDv. 34229 Zip Code
Virtually Staged. Welcome to Blackburn Point Marina Village, an intimate gated waterfront community of just 19 residences near Sarasota and Casey Key. This beautifully upgraded townhome delivers a relaxed coastal lifestyle with low-maintenance living—without the waterfront price tag. A bright, open floor plan features 9-foot ceilings, plantation shutters, ceiling fans, and new luxury vinyl flooring installed in 2025. The enclosed sunroom adds versatile living space for relaxing, entertaining, or enjoying the Florida sunshine. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, Craft Maid cabinetry, a KitchenAid gas range, LG refrigerator (2023), and wine refrigerator. Enjoy peace of mind with a new roof (2025), water filtration and softener system (2024), tankless water heater, motorized hurricane shutters, epoxy-finished garage floor, and a LiftMaster garage door with camera (2025). The first-floor primary suite provides a private retreat, complete with dual vanities, a soaking tub, and a walk-in shower. Ideally located near Casey Key Marina, Blackburn Point Park, and Casey Key Fish House & Tiki Bar, this home puts boating, waterfront dining, and outdoor recreation close at hand. Community amenities and water and gas service are included, making this an exceptional opportunity to enjoy the Sarasota coastal lifestyle. One or more photo(s) was virtually staged.

1140 Beachcomber Court Unit 11, 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

$1,900,000
5 Beds 8 Baths The Oaks SubDv. 34229 Zip Code
Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey

$317,000
3 Beds 2 Baths Bay Street Village & Towncenter Land Condo SubDv. 34229 Zip Code
"Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath the residence offers convenience when arriving or heading out. The open-concept layout floor plan, soaring ceilings, and split-bedroom layout create perfect privacy. Stunning chef’s kitchen, granite countertops, stainless steel appliances, and a center island with seating, walk-in pantry, and upgraded fixtures. The primary suite features a walk-in closet, a spa, a double vanity, and a walk-in shower. Two other bedrooms on the opposite side, along with a second full bathroom, gives comfort and privacy for families or guests. Relax on the screened-in lanai overlooking beautiful water views for morning coffee or evening cocktails. The Tesla charger installed in the garage is a bonus. The community is located in a prime location with quick access to US-41, I-75, Siesta Key Beach, and Nokomis Beach, Bay Street Park with its playground and dog park, and walking distance to renowned Pine View School, Walmart, and the Legacy Trail. Bay Street Village resort-style amenities include a heated pool, fitness center, and clubhouse. The monthly condo fee covering exterior maintenance, roof, water, sewer, and two gated entrances… Don’t miss this rare opportunity – call the listing agent now to schedule a private viewing.

4213 Expedition Way Unit 107, Osprey

$1,289,000
3 Beds 4 Baths The Oaks SubDv. 34229 Zip Code
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

156 Bishops Court Road, 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

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