Osprey Homes with Lake Front Water Frontage

Osprey Homes with Lake Front Water Frontage

Welcome to Osprey, Florida, a charming slice of paradise nestled in the heart of Sarasota County. Known for its picturesque landscapes and serene atmosphere, Osprey offers a delightful blend of coastal living and small-town charm. Just a stone's throw away from the stunning shores of the Gulf of Mexico, this vibrant community is perfect for those seeking a peaceful retreat while still enjoying the conveniences of modern life.

One of the most enchanting features of Osprey is its stunning homes with lakefront and waterfront properties. Imagine waking up each morning to the soothing sounds of nature, with the gentle lapping of water just outside your window. These homes not only provide breathtaking views but also offer a lifestyle rich in outdoor activities. Whether you enjoy fishing, kayaking, or simply soaking up the sun by the water's edge, Osprey's waterfront properties cater to every taste.

In addition to its natural beauty, Osprey boasts a welcoming community atmosphere, complete with local shops, delightful eateries, and recreational parks. Residents can explore the nearby Oscar Scherer State Park, where miles of hiking trails and abundant wildlife await. The proximity to Nokomis Beach adds to the allure, providing easy access to pristine sandy shores and stunning sunsets.

With a rich history, vibrant culture, and an array of outdoor adventures, Osprey is more than just a place to live; it’s a lifestyle choice. Discover the magic of Osprey and find your dream home with lakefront or waterfront access today!

Newest Osprey Homes with Lake Front Water Frontage

2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code

Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with maintenance-free grounds and an all-inclusive HOA that covers insurance, roof, exterior maintenance, landscaping, roads, pool and tennis facilities, docks/boat slips, cable TV, high-speed internet, water, trash and sewer. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and new countertop, The vaulted-ceiling living room offers tranquil lake views overlooking the bay, with many evenings capped by stunning sunsets over the Bay. STORAGE! in addition to the garage there is an interior attic! Outside, a 587 sqft courtyard with a hot tub invites outdoor relaxation and entertaining and expands the indoor-outdoor living space to 2,161 sqft Community amenities include a heated bayside swimming pool, tennis court, a fishing pier, kayak launch, and dockage for 10 boats—complete with electric and water—available to residents at NO COST. This is a very private location. Located directly on Little Sarasota Bay with no fixed bridges near MIDNIGHT PASS, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Nokomis beach is only a few miles away. Enjoy waterfront dinning at Casey Key Fish House, The Point and Deep Lagoon Oyster House. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.

780 Sarabay Road Unit 16, Osprey

3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances. The designer-level, fully customized laundry room includes soft-close custom cabinets, a laundry sink, a custom backsplash, and a stacking washer and dryer, providing exceptional storage and functionality. The primary suite offers a water view, a barn-door entry to the bath, a custom frameless glass shower enclosure with stone flooring, a linen closet, custom closet organizers, and a designer ceiling fan with light. Bedroom two also features custom closet organizers, while bedrooms two and three include custom ceiling fans. Ceiling fans are additionally installed in the great room and the lanai for enhanced comfort. Plantation shutters are installed in the entry foyer, primary bedroom, bedrooms 2 and 3, and the family room, adding style, privacy, and a cohesive look throughout the home. Additional upgrades include upgraded carpet on the stairs and in the primary bedroom, keyless front-door entry, keyless man-door entry, and an exterior garage door keypad. Quality construction provides peace of mind with hurricane-impact windows and doors, concrete block construction, a tile roof, and a paver driveway. The monthly condo fee covers water, sewer, exterior maintenance, landscaping, gated entry, a heated resort-style pool, cabana, fitness center, and clubhouse. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key, the Legacy Trail, Oscar Scherer Park, Sarasota and Venice shopping and dining, and A-rated Pine View School. Maintenance-free Florida living at its best.

173 Navigation Circle Unit 107, Osprey

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the elevator lobby. The expansive split-bedroom floor plan includes 3 bedrooms, 3 full baths, and a private den/study/office that can easily function as a 4th bedroom, providing exceptional flexibility for both everyday living and visiting guests. Filled with natural light, the spacious great room and dining areas flow seamlessly to the generous terrace with upgraded ceramic tile, where peaceful water and preserve views create a serene backdrop for relaxing or entertaining. The custom kitchen, redesigned in 2023, is both elegant and functional, featuring soapstone countertops, Bosch appliances, roll-out cabinetry, Everpure water filtration, a tray ceiling, and detailed crown molding. The primary suite is a private retreat, offering picturesque water views, a custom-designed walk-in closet, and a beautifully appointed bath with Italian tile, dual vanities, and stunning stone countertops. Custom built-ins, upgraded closet systems, and a thoughtfully designed laundry room further enhance the home's comfort and functionality. Residents of The Meridian enjoy lushly landscaped grounds, winding pathways, a community pool and spa, fitness center, and outdoor grilling area. Membership in The Oaks Club is required, providing access to one of Sarasota's most distinguished private club lifestyles, including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art wellness center, resort-style pool, multiple dining venues, a vibrant social calendar, and an elegant clubhouse. Ideally located near Historic Spanish Point, Pine View School, Siesta Key Beach, and downtown Sarasota, this exceptional residence offers a rare combination of luxury, privacy, natural beauty, and resort-inspired living.

401 N Point Road Unit 504, Osprey

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining beautiful kitchen with center island, walk-in pantry and stainless steel appliances. The primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Bay Street offers easy access to Nokomis Beach and the world-famous Siesta Key Beach. Close to shopping and restaurants.

4296 Expedition Way Unit 104, Osprey

4 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.

89 Navigation Circle, Osprey

1 Beds ⋅ 1 Baths ⋅ Windsor Lodge At The Oaks SubDv. ⋅ 34229 Zip Code

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

51 Macewen Drive Unit 12, Osprey

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

2 Beds ⋅ 2 Baths ⋅ Sorrento Shores SubDv. ⋅ 34229 Zip Code

This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.

107 Sorrento Drive, Osprey

2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code

Virtually Staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10 beautifully manicured acres, this home offers the ultimate Florida lifestyle. Enjoy resort-style amenities including a heated waterfront pool, tennis courts, kayak launch, fishing pier, and community docks with water and electric. Best of all, there are 10 free boat slips with no fixed bridges to the Gulf, making this a boater’s paradise, so bring your boat and go! This spacious two-bedroom, two-bath villa features sweeping views of Little Sarasota Bay, the Intracoastal Waterway, the community pond and pool. The open concept floor plan is enhanced by 15-foot ceilings, abundant natural light, and seamless indoor-outdoor living. Relax on the screened lanai, cool off in your heated waterfront pool and enjoy nightly sunsets that never get old. A private gated courtyard entry sets the tone for this unique home, complete with a new paved walkway and pet-friendly artificial turf, completely maintenance-free. Inside, enjoy ES Prestige impact-rated windows and sliding glass doors, all-new kitchen appliances, and an eat-in kitchen overlooking the courtyard. The primary suite offers lanai access through sliding glass doors and features two custom walk-in closets. The second bedroom also opens to the private courtyard and includes its covered lanai, perfect for guests or a home office retreat. Conveniently with quick access to Interstate 75, shopping, dining and beaches, this exceptional waterfront villa delivers boating, fishing, views and effortless Florida living in one remarkable package. A rare opportunity, this is waterfront living at its finest. Schedule your private showing today.

764 Sarabay Road Unit 8, Osprey

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