Osprey Homes with Pool Community Features

Osprey Homes with Pool Community Features

Welcome to Osprey, Florida—a hidden gem nestled in the heart of Sarasota County. With its picturesque landscapes and a vibrant community spirit, Osprey offers an idyllic setting for those seeking a tranquil yet engaging lifestyle. Just a stone's throw away from the stunning Gulf Coast beaches, this charming town boasts a unique blend of natural beauty and modern conveniences, making it the perfect place to call home.

Osprey is renowned for its rich history and cultural offerings. Explore the nearby historic Spanish Point, where you can immerse yourself in the area's heritage, or take a leisurely stroll through the lush parks and nature preserves that dot the landscape. The community is also home to an array of shopping and dining options, ensuring that residents have everything they need right at their fingertips.

For those who enjoy outdoor living, Osprey's homes with pool community features are a true highlight. Imagine soaking up the Florida sun in your own private oasis, complete with a sparkling pool surrounded by lush landscaping. These communities are designed for relaxation and enjoyment, offering amenities that encourage a vibrant social lifestyle. Whether you're hosting a barbecue with friends or enjoying a quiet evening under the stars, a home with a pool in Osprey provides the perfect backdrop for creating lasting memories.

With its combination of natural beauty, cultural richness, and fantastic community features, Osprey is more than just a place to live—it's a place to thrive. Discover your dream home in this enchanting town and experience the best that Florida has to offer!

Newest Osprey Homes with Pool Community Features

$775,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy breathtaking sunsets from your private screened-in balcony as you look out across the bay to the barrier island of Casey Key. Inside the unit, you'll find a spacious living room and dining room featuring an open floor plan. The gourmet kitchen offers KitchenAid stainless steel appliances, quartz countertops, white shaker-style cabinetry, counter seating and plenty of storage cabinets. The primary bedroom is expansive with large walk-in closets, closet organization system and direct access to the outside balcony. Both guest bedrooms have dual purpose, as they both have built-in Murphy beds, desk workstations, plantation shutters and walk-in closets. If you're looking for a condominium with extra space for a den/office/sewing room/craft room or TV media room, this is the one that offers it all. More great features are impact-resistant windows and doors, a large laundry room with built-in cabinetry, a full-size washer and dryer and utility sink. One assigned parking space with a large storage unit with a roll-down door for all your extra gear. Some of the amenities include a new fishing pier, lit pickleball courts, kayaking and kayake racks for storage, clubhouse, swimming pool, spa and tiki hut with grilling barbeque stations. The location is walkable to many restaurants, shopping and the post office. Bike the Legacy Trail or head to the beach that's just a few miles away. There's so much to do just minutes away.

260 Hidden Bay Drive Unit 402, Osprey
$630,000
4 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

1036 Oak Meadow Lane, Osprey
$595,000
3 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Discover one of Osprey's best-kept secrets-The Cottages of Rivendell. Tucked away within The Woodlands of Rivendell, offers a lifestyle that is becoming increasingly rare. Towering oak trees create a tranquil, park-like setting, while charming front porches, white picket fences, and classic Old Florida architecture give the neighborhood its unmistakable character. This beautifully maintained 3/2 home welcomes you with an expansive great room featuring an elegant tray ceiling, creating a wonderful sense of openness. Enjoy peace of mind with numerous recent updates, including a new roof (2022), HVAC system (2025), water heater (2026), exterior paint (2026), a separate AC system for the garage, and a generator for the house. Residents enjoy exclusive access to a private community pool and clubhouse, while the Association provides landscape maintenance, allowing you to embrace a carefree, low-maintenance lifestyle. What truly sets The Cottages of Rivendell apart is its warm sense of community. Neighbors know one another, friendships flourish, and life's special moments are celebrated together, making this a truly exceptional place to call home. Ideally located just a short walk from the nationally recognized Pine View School, one of Florida's top-rated schools for the gifted, and only 5.5 miles from Nokomis Beach.

547 Meadow Sweet Circle, 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
$172,000
1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a balcony, creating a seamless indoor-outdoor living experience. Master bedroom with en-suite bath, vaulted ceiling and another balcony! The updated kitchen boasts beautiful butcher block countertops and you’ll enjoy peace of mind that comes with a NEW TANKLESS HOT WATER HEATER. Pine Run is a vibrant, amenity-rich community offering tennis and pickleball courts, two swimming pools, a clubhouse with a fitness room and over 20 acres of mature trees, lush landscaping and a scenic pond with water feature. Ideally located between Sarasota and Venice, you’ll be just minutes from the beautiful beaches of Siesta Key and Nokomis Beach. Shopping, dining and everyday conveniences along with the Intracoastal Waterway and one of the area’s favorite waterfront restaurants, Casey Key Fish House & Tiki Bar are all just a walk away! Come take a look - your new lifestyle is waiting - make it your own!

701 Pine Run Drive Unit 701, Osprey
$425,000
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
$285,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has access from the dinette area. A spacious center atrium feels like a peaceful retreat. The main covered lanai off the living room and dining room is screened in with a door to the back yard. Each bedroom has it’s own small patio with privacy fence. Kitchen is nicely equipped with washer and dryer in the dinette closet area. The hallway has large almost floor to ceiling windows looking onto the center atrium for a very open feel. Pine Run is an active community nestled between mature landscaping and trees, with many activities including pickleball, tennis, kayak storage and two swimming pools! Launch your kayaks in the Blackburn Point Park and boat launch just down the road. Pine Run is conveniently located near shopping, restaurants, major roads and Casey Key Fish House and Tiki Bar. Sarasota is about 13 miles away, Venice about 7 miles. Area beaches are close at hand with Nokomis Beach just 5 miles and Siesta Key Beach is 9 miles. You are in the heart of paradise! Come see for yourself!

108 Woodland Place Unit 108, Osprey
$497,000
3 Beds ⋅ 3 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code
West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

2309 Jessie Harbor Drive Unit 2402, Osprey
$1,790,000
3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.

206 Four Knot Lane, Osprey
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey
$319,500
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
$880,000
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
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