Osprey Homes with Sidewalk Exterior Features

Osprey Homes with Sidewalk Exterior Features

Welcome to Osprey, Florida—a charming gem nestled in Sarasota County, where the sun-kissed beaches meet the tranquility of suburban living. This picturesque community, which seamlessly blends the allure of coastal life with a rich tapestry of nature and culture, offers residents a unique lifestyle that is both vibrant and serene.

Osprey is renowned for its stunning waterfront views and proximity to the breathtaking Gulf of Mexico. With a variety of outdoor activities at your doorstep, including kayaking, fishing, and leisurely strolls along sandy shores, it’s no wonder that this area attracts those seeking a laid-back yet active lifestyle. The nearby Oscar Scherer State Park provides ample opportunities for hiking and wildlife observation, making it a favorite among nature enthusiasts.

One of the standout features of homes in Osprey is their charming sidewalk exterior. These inviting walkways not only enhance the aesthetic appeal of the neighborhood but also promote a sense of community and connectivity. Imagine taking evening strolls with family and friends, waving to neighbors, and enjoying the warm Florida breeze. The sidewalks create a pedestrian-friendly atmosphere, encouraging outdoor gatherings and fostering relationships among residents.

In Osprey, you’ll find a diverse selection of homes that cater to various tastes and lifestyles, from cozy bungalows to luxurious waterfront estates. Each property is designed to embrace the Florida lifestyle, with spacious layouts and outdoor living spaces perfect for entertaining or simply soaking in the sun.

Discover the enchanting community of Osprey, where your dream home awaits amidst beautiful surroundings and friendly faces. Experience the perfect blend of nature, culture, and community in this idyllic Florida paradise!

Newest Osprey Homes with Sidewalk Exterior Features

819 Golden Pond Court, Osprey
$799,000
4 Beds ⋅ 3 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Virtually Staged. Set on a private, preserve lot in Woodlands at Rivendell, this inviting home offers peaceful views and a desirable open floor plan. 4 bedrooms, 3 full bathrooms, 2-car garage with epoxy-coated flooring and roof replaced in June 2025. The grand covered entry and front porch lead into formal living and dining rooms, with neutral tile throughout the main living areas. The spacious family room features a built-in entertainment center and sliding glass doors opening to the lanai. The eat-in kitchen is appointed with maple wood cabinetry, granite countertops, tumbled marble backsplash, stainless steel appliances, farmhouse sink, under-cabinet lighting, ample pantry storage, and a breakfast bar. The primary suite features two walk-in closets and a separate bonus room overlooking the pool, ideal for a sitting area or home office. The ensuite bath offers separate vanities, soaking tub, and a walk-in shower. A split-bedroom layout provides three additional bedrooms and two full bathrooms on the opposite side of the home, offering privacy and flexibility. One bathroom serves as a convenient pool bath with direct access to the lanai. Enjoy the privacy of the secluded backyard, featuring an expanded screened lanai, heated pool and spa, and an expansive stone paver deck with plenty of room for entertaining. Additional stone paver space beyond the pool enclosure offers even more outdoor living options. Woodlands at Rivendell is a quiet, nature-filled community nestled among acres of lakes, preserves, and open spaces. Amenities include a heated community lap pool, playground, and scenic nature trails. Outdoor enthusiasts will appreciate the nearby Bay Street entrance to the Legacy Trail for biking and hiking, Oscar Scherer State Park for camping, hiking, kayaking, canoeing, and birding, and the boat and kayak launch on Blackburn Point for access to the Intracoastal Waterway. Conveniently located between Sarasota and Venice, the community is minutes from Gulf beaches, as well as shopping, dining, medical facilities, and cultural attractions. Experience the best of Florida living, surrounded by nature and close to everything you need.

819 Golden Pond Court, Osprey
250 Hidden Bay Drive Unit 301, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in January 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy-to-maintain tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area opens to a large, screened-in terrace with privacy screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, a makeup vanity and a walk-in shower. Additional features include a private den/office, an in-unit laundry room, two full baths and a powder room, and air conditioner from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with a kitchen and quartz bar, a heated pool and spa, a fitness center, a library, a tiki hut with grilling stations, pickleball and tennis courts, a kayak launch, a fishing pier, a dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey, just south of Sarasota, near area beaches, shopping and dining and only minutes from Venice.

250 Hidden Bay Drive Unit 301, Osprey
335 Park Trace Boulevard, Osprey
$739,000
3 Beds ⋅ 2 Baths ⋅ Park Trace Estates SubDv. ⋅ 34229 Zip Code
Virtually Staged. Welcome to 335 Park Trace Blvd, an exceptional residence in the sought-after Park Trace Estates of Osprey, close to Pineview Education Center and The Legacy Trail where refined interiors, custom craftsmanship, and spectacular water views come together to create an elegant Florida retreat. From the moment you enter, the home makes a statement with its open living and dining spaces, dramatic triple tray ceilings, custom woodwork, and beautifully detailed wainscoting. A custom electric fireplace serves as a striking focal point, while the private den is enhanced by custom built-in shelving and handsome bookcases—an ideal setting for a home office, library, or quiet retreat. The kitchen features a Viking gas range, a Bosch dishwasher and refrigerator, offering both style and functionality for everyday living and entertaining. Designed for an exceptional indoor-outdoor lifestyle, the home opens to an extraordinary 44' x 39' screened lanai, featuring a gas-heated saltwater pool and approximately 32' x 24' of covered outdoor living space. Whether hosting an elegant gathering or enjoying a quiet evening at home, the expansive outdoor setting provides a front-row seat to the beautiful water views. The residence offers three generously proportioned bedrooms, each complemented by plantation shutters and an updated Jack & Jill Bath. The luxurious primary suite is a private sanctuary, featuring a spacious bath with a walk-in shower, soaking tub, and large walk-in closet. Important updates provide added peace of mind, including a new flat tile roof installed in 2026, plus an updated A/C system and hot water heater, both replaced in 2022. A large two-car garage adds valuable functionality, complete with a workbench and impact-rated garage door, providing ample space for vehicles, storage, and projects. With its remarkable water views, extensive custom millwork, designer-quality details, resort-style pool and lanai, updated systems, and exceptional outdoor living space, this home is waiting for you.

335 Park Trace Boulevard, Osprey
7303 Jessie Harbor Drive Unit 7303, Osprey
$449,000
3 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey
3603 N Point Road Unit 202, Osprey
$629,400
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **A MUST SEE**

3603 N Point Road Unit 202, Osprey
1346 Thornapple Drive, Osprey
$540,000
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, Osprey
256 Sugar Mill, Osprey
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code
This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

256 Sugar Mill, Osprey
1328 Thornapple Drive, Osprey
$719,900
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Virtually Staged. **PRICE IMPROVEMENT BY $30K!** Welcome to your ultimate lakeside maintenance free sanctuary! This home is nestled in a premier community renowned for its top-rated gifted school district & the renowned high quality builder Lee Wetherington. This expanded floor plan in the Willowbend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, ceiling fans and window treatments. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-impacted, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

1328 Thornapple Drive, Osprey
5100 Jessie Harbor Drive Unit 404, Osprey
$599,000
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
1036 Oak Meadow Lane, 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
7204 Jessie Harbor Drive Unit 7204, 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
360 N Point Road, Osprey
$1,445,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey
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