Osprey Homes with Deed Restrictions Community Features

Osprey Homes with Deed Restrictions Community Features

Welcome to Osprey, Florida—a hidden gem nestled in the heart of Sarasota County, where coastal charm meets suburban tranquility. Known for its stunning natural beauty and rich cultural heritage, Osprey offers residents a unique blend of outdoor adventures, artistic flair, and a welcoming community atmosphere. Just a stone’s throw away from the pristine beaches of Nokomis and Siesta Key, Osprey is perfect for those who crave sun-soaked days and picturesque sunsets.

One of the standout features of Osprey is its array of homes within deed-restricted communities. These neighborhoods are designed to maintain the aesthetic appeal and value of the area, ensuring that your investment is protected. Residents enjoy beautifully landscaped surroundings, well-maintained common areas, and an active lifestyle that promotes community engagement. From social clubs to recreational facilities, these communities foster a sense of belonging among neighbors, making it easy to forge lasting friendships.

In addition to its residential charm, Osprey is rich in amenities. Explore the nearby Oscar Scherer State Park, where you can hike, bike, or kayak through lush landscapes and serene waters. Indulge in local dining options that celebrate fresh seafood and farm-to-table cuisine, or visit the historic Spanish Point to immerse yourself in the region's heritage.

Whether you’re looking for a serene retreat or an active lifestyle, Osprey’s deed-restricted communities offer the perfect blend of comfort, security, and connection. Discover your dream home in this enchanting coastal town and experience the vibrant lifestyle that Osprey has to offer!

Newest Osprey Homes with Deed Restrictions Community Features

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

A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay frontage across 0.60 acres, with water views framing nearly every principal room. The residence offers 6 bedrooms, 5.5 baths, multiple covered balconies overlooking the Bay, additional ground-level flex space and a side-entry 3-car garage. A circular brick-paver driveway, tropical landscaping and a stately columned entrance create an unforgettable arrival. The dramatic two-story foyer features architectural columns, custom millwork and a wood-clad ceiling accent. European French white oak engineered flooring flows through the main living spaces. The living and family rooms feature soaring ceilings, extensive millwork, statement lighting, carved-stone fireplaces and oversized windows framing expansive water views. An adjoining sitting area features arched windows, a wood-clad ceiling and multiple glass doors opening to the waterfront balcony. The new kitchen is appointed with ceiling-height Shaker cabinetry, champagne-bronze hardware, marble countertops and an oversized waterfall island with seating for five. A GE Monogram appliance suite includes a professional gas range with griddle, refrigerator and dishwasher. A custom range hood, dimensional tile backsplash, apron-front sink and walk-in pantry complete the space. The waterfront dining nook incorporates built-in cabinetry, a stone serving counter and beverage cooler, while the formal dining room features a tray ceiling, paneled walls and columns. A waterfront office with built-in bookshelves, fireplace and balcony access, an updated laundry room and multiple en-suite guest accommodations complete the main level. Upstairs, the landing overlooks the living spaces beneath a crystal chandelier. The primary suite offers separate sleeping and sitting areas, a carved-stone fireplace, wide water views, private balcony access and two walk-in closets with custom storage. Its spa-inspired bath includes dual furniture-style vanities, a freestanding soaking tub beneath a picture window and an oversized frameless shower with marble-look tile, rainfall and handheld fixtures. Additional bedrooms offer en-suite or nearby baths, walk-in closets, abundant natural light and water or tropical views. Multiple covered balconies overlook the newly resurfaced pool, paver terrace, manicured lawn and waterfront. The pool features a 7-foot depth, entry steps, seating or sun-shelf areas, lighting, a self-cleaning system and a new pump. A private walkway through the mangroves leads to a new 5-by-60-foot composite dock completed in 2026, equipped with electric, water and a 6,000-pound boat lift. The property also features a concrete seawall and direct boating access. The lower level provides substantial additional flexibility for recreation, fitness, media or entertaining. Further updates include a newer 2023 tile roof, new HVAC, all-new appliances and flooring, new interior doors and moldings, hurricane protection and exterior lighting. The renowned Oaks Club is one of the area’s premier member-owned clubs, featuring two championship 18-hole golf courses, a full slate of tennis and fitness facilities, and an elegant clubhouse offering fine dining and a vibrant social calendar. Ideally situated in Osprey, the property offers convenient access to Gulf beaches, the Legacy Trail, dining and shopping, with downtown Sarasota and Venice both within easy reach.

112 Osprey Point Drive, Osprey

4 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34229 Zip Code

Priced to sell! Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble backsplash, recessed lighting, an undermount sink, and newer Whirlpool appliances. A split floor plan provides privacy with spacious bedrooms, including a primary suite with lanai access, two closets (one walk-in), and a spa-like bath with soaking tub, walk-in shower, and dual quartz vanities. The screened lanai overlooks an inviting pool and spa with a private, tree-lined backdrop. Other highlights include a dedicated laundry room, 2-car garage with new door and opener, newer roof, A/C, and water heater. All improvements and system updates completed in 2020. Last year, the pool was resurfaced and the waterline tile replaced. Additional upgrades include new pool equipment, a saltwater system, and a heater. Low HOA and no CDD. Conveniently located near top-rated schools, Oscar Scherer State Park, shopping, dining, and world-class beaches including Siesta Key, Nokomis, and Venice.

583 Pine Ranch East Road, Osprey

3 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities and driving ranges. The member-owned Oaks Club features a 34,000-square-foot clubhouse with multiple dining venues, tennis courts, pickleball courts,a resort-style pool, and a 7,500-square-foot fitness center. Beyond the community gates, this location provides convenient access to Gulf Coast beaches, scenic trails including The Legacy Trail, local parks, as well as the cultural offerings of Sarasota and Venice. Schedule a private tour to explore the property and experience the distinct lifestyle of The Oaks Club.

226 Saint James Park, Osprey

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

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

2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

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

ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of Little Sarasota Bay and the Gulf immediately take center stage. Thoughtfully designed with an impressive array of upgrades, the residence features high ceilings, crown molding, hardwood and tile flooring, and a beautifully appointed kitchen with a large island and seating area, granite countertops, stainless steel appliances, solid-wood cabinetry, and ample storage. The spacious Owner’s Suite is a peaceful retreat, complete with a generous walk-in closet, custom-tiled shower, relaxing soaking tub, and dual vanities. Step outside onto the expansive balcony and enjoy a serene setting surrounded by spectacular water views, abundant wildlife, and unforgettable Gulf sunsets. Hurricane-impact windows and sliding doors provide added peace of mind. Climate-controlled storage is conveniently located on the second floor. Residents of Meridian enjoy an array of private amenities, including a heated pool and spa, fitness center, and outdoor grilling area, along with access to the exceptional amenities of The Oaks Club’s main campus. Experience elevated coastal living, spectacular views, privacy, and resort-style amenities—all from this remarkable penthouse at The Oaks. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional residence is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location.

409 N Point Road Unit 803, Osprey

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

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

299 Turquoise Lane, Osprey

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

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

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. THE ROOF WAS INSTALLED IN 2019, A/C APROX. 7-8 YEARS OLD, ELECTRIC WAS COMPLETELY INSPECTED IN 2025 BY GRAHAM ELECTRIC WITH CORRECTION MADE TO CODE., NEW APPLIACNES, EXTERIOR OF BUILDING WAS PAINTED 12/2025. 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

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