Osprey/Nokomis Homes with Maintenance Amenities

Osprey/Nokomis Homes with Maintenance Amenities

Welcome to the enchanting communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. This picturesque region boasts a perfect blend of serene coastal living and vibrant community spirit, making it an ideal destination for those seeking a tranquil yet engaging lifestyle.

Osprey, known for its lush landscapes and rich history, offers residents an array of outdoor activities, including boating, fishing, and nature trails. With its close proximity to the stunning beaches of Siesta Key and Casey Key, residents can enjoy sun-soaked days by the water, while the charming shops and restaurants in the area provide a delightful taste of local culture. Nokomis, just a stone's throw away, complements this idyllic setting with its welcoming atmosphere and friendly neighborhoods, making it a perfect place for families and retirees alike.

One of the standout features of living in Osprey and Nokomis is the availability of homes with maintenance amenities. These properties allow residents to indulge in a carefree lifestyle, as the management takes care of the landscaping, pool maintenance, and other essential services. Imagine spending your weekends relaxing by the pool or exploring the natural beauty of nearby parks, all while knowing that your home is being well cared for.

Whether you're looking for a charming single-family home or a luxurious waterfront property, Osprey and Nokomis offer a diverse range of real estate options to suit every taste and budget. Embrace the enchanting lifestyle of this coastal paradise, where relaxation meets recreation in perfect harmony. Come discover your dream home in Osprey and Nokomis today!

Newest Osprey/Nokomis Homes with Maintenance Amenities

$848,600
3 Beds ⋅ 3 Baths ⋅ Bellacina By Casey Key SubDv. ⋅ 34275 Zip Code
Finally…the one you’ve been waiting for! This stunning 2021 Lazio model home offers 3 bedrooms, 3 full baths, a versatile Flex Room/Office & an expanded tandem 3-car garage. All thoughtfully enhanced with premium upgrades. Built with impact-resistant windows & sliding glass doors, this light-filled home features an open-concept floor plan with soaring 10-foot ceilings & 8-foot interior doors, creating a seamless blend of elegance, comfort & security. Easy-care tile flooring throughout & light coastal-inspired finishes create a warm & inviting atmosphere. At the heart of the home, the chef’s kitchen impresses with a natural gas range, upgraded stainless steel appliances, 42-inch solid-wood cabinetry and a large quartz island perfect for home gatherings. The adjacent dining area & expansive screened lanai provide effortless indoor-outdoor living, ideal for enjoying spectacular private views. A generous pantry, oversized breakfast bar & fabulous outdoor kitchen/bartop provide exceptional functionality for entertainment. The living spaces flow seamlessly to the extended screened lanai & custom-designed pool, featuring numerous upgraded water features that create a private outdoor retreat. The luxurious primary suite serves as a serene sanctuary, complete with an oversized walk-in closet & a spa-inspired bath featuring solid-wood cabinetry, quartz countertops, dual vanity areas & an expanded walk-in shower. Designed with both comfort & practicality in mind, this popular floor plan offers abundant storage, privately situated guest bedrooms, an enlarged laundry room & an expanded garage with plenty of room for all your Florida lifestyle essentials! Enjoy maintenance-free living in a gated, natural gas community with outstanding resort-style amenities, including a clubhouse, heated pool/spa, 24-hour fitness center, pickleball, tennis & bocce courts, fire pit, catering/outdoor kitchen & on-site property manager. Pet lovers will appreciate the 2 dedicated dog parks for your furry family members. Ideally located with easy access to Downtown Sarasota, charming Downtown Venice, world-renowned Gulf Coast beaches & private community access to the storied 20+ mile Legacy Trail, this move-in ready home exemplifies pride of ownership while offering the perfect blend of luxury, convenience & elevated coastal living. Don’t miss this exceptional opportunity!

5880 Semolino Street, Nokomis
$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. 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
$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
$154,900
1 Beds ⋅ 1 Baths ⋅ Kings Gate Club SubDv. ⋅ 34275 Zip Code
Waterfront property. This 1/1 charming home offers a peaceful, easygoing lifestyle just minutes from Florida’s Gulf Coast. Whether you're looking for a seasonal escape or a full-time residence, Turnkey, Furnished residence in the 55+ gated community of Kingsgate Park, where affordable coastal living meets convenience. Inside, the layout is light and welcoming, with comfortable furnishings and a washer and dryer included for added convenience. Simply unpack and start living the Florida lifestyle. Updated Roof, Tie-down straps, and elevated for so much more peace of mind. A convenient path leads directly to the clubhouse, making it easy to join in the fun or simply relax and enjoy the community. Residents of Kingsgate Park can be as active as they wish to with amenities that include a community pool, tennis and pickleball courts, shuffleboard, and a clubhouse featuring a fitness room, billiards, darts, card clubs, crafts, dances, dinners, movie nights, and so much more The low HOA fee includes Blue Stream TV and internet, water, sewer, trash, and grounds maintenance. Enjoy the community boat ramp to launch your boat or kayak directly into Shakett Creek which leads to the Intracoastal and Gulf of America with only 3 fixed bridges. From land, Kingsgate is located less than 5 miles to Nokomis Beach, just over 2 miles to Legacy Trail. Close to local amenities, beaches, and Tiki Bars and Live entertainment. The best game fishing in the world with off speed boat racing to spring training baseball teams as The Atlanta Braves and Tampa Rays. Just want to go to the beach or go fishing for the day. Great to do it all with whatever you can dream or do as a hobby. Local International Airports: Fort Myers, Sarasota and local Punta Gorda with Allegiant airlines direct. Many outdoor concert venues weekly. Local parks, state parks, tennis or pickle ball, to amazing golf courses. You deserve to view this property and make it your home or investment.

125 Brookshire Drive, Nokomis
$1,149,900
3 Beds ⋅ 3 Baths ⋅ Venetian Golf & River Club SubDv. ⋅ 34275 Zip Code
Enjoy long, private lake views and peaceful rising sun mornings from this highly desirable Francesca model in the Venetian Golf & River Club. Loved for its open concept and natural flow, this floor plan features tall ceilings with crown molding, Italian tile in the main living areas, an updated kitchen, and warm natural light that fills the home at daybreak. Impact windows and doors provide year round confidence, complemented by automated Storm Smart hurricane shutters at the front entry and across the entire lanai. A new roof was installed in 2025 for added peace of mind. The split layout offers 3 bedrooms, 3 full baths (including a convenient pool bath), an office/den, and a versatile flex room ideal for fitness, hobbies, or storage. The true dining room includes plantation shutters, and all bedrooms feature carpeting and ceiling fans for comfort. Outdoor living embraces the tranquil lake backdrop, where preserve views on both sides create a sense of privacy and calm. The large infinity edge pool and spa overlook shimmering water and morning wildlife activity, with a newer pump, pop up cleaners, and generous deck space perfect for quiet coffee moments or relaxed entertaining. A 3 car side load garage, oversized paver driveway, and additional parking pad provide excellent convenience and functionality. Located in the gated, amenity rich Venetian Golf & River Club, residents enjoy dining, fitness, tennis, pickleball, nature trails, and optional golf. All of this is just minutes from shopping, multiple beaches, dining, and I 75—an ideal blend of comfort, thoughtful updates, and peaceful lakefront living.

286 Pesaro Drive, Nokomis
$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
$405,000
2 Beds ⋅ 2 Baths ⋅ Vicenza SubDv. ⋅ 34275 Zip Code
Welcome to effortless Florida living in the highly sought-after community of Vicenza! Why wait months to build when this LIKE-NEW, move-in ready home is loaded with premium upgrades and perfectly positioned on a private homesite in an X Flood Zone with LOW HOA fees and no CDD fees. This home comes with a HOME WARRENTY for a worry free transition! Designed for easy living, this beautifully appointed home features: Wood-look tile throughout, Impact windows, 9-foot doors, Recessed ceilings, Upgraded cabinets, Soft-close drawers, Quartz countertops, Designer backsplash, Farmhouse sink, Under-cabinet lighting, Upgraded hardware, Utility sink, Energy-efficient foam insulation, Epoxy-coated garage floor, Gas stub-in on lanai, Extended lanai, Preserve view and countless thoughtful upgrades make this home as practical as it is beautiful. Whether you're looking for the perfect full-time residence or a low-maintenance retreat, you'll love the UNBEATABLE LOCATION—just minutes to I-75, world-class beaches, dining, shopping, golf, and all the exciting new development Sarasota County has to offer. Privacy, convenience, and like-new quality... this home truly has it all!

244 Altamura Circle, Nokomis
$525,000
2 Beds ⋅ 2 Baths ⋅ Bellacina By Casey Key SubDv. ⋅ 34275 Zip Code
MOTIVATED SELLER! FURNITURE NEGOTIABLE! Welcome to this stunning Taylor Morrison Roma model, nestled within the sought-after gated community of Bellacina by Casey Key. Offering 2 bedrooms, 2 bathrooms, and a versatile Flex/Den, this beautifully maintained home perfectly captures the very best of the Florida lifestyle — from its thoughtful interior upgrades to its world-class community amenities and unbeatable coastal location. From the moment you arrive, lush, professional landscaping and exceptional curb appeal set the tone. Inside, elegant tray ceilings, recessed lighting, and smart home features create an atmosphere of modern sophistication, while ceramic tile flows seamlessly through all main living areas. The bedrooms are appointed with warm, durable luxury vinyl flooring for added comfort. Every window is beautifully dressed — with Roman shades and window treatments throughout the home, lending a polished, cohesive look from room to room. The gourmet kitchen is a true showpiece, featuring striking white quartz countertops, white cabinetry, a gorgeous grey stone backsplash, a brand new dishwasher, and full pull-out cabinet storage — an entertainer's dream and an organizer's delight. The kitchen flows effortlessly into the main living areas, making everyday living as functional as it is beautiful. The primary suite offers a peaceful retreat, while the second bedroom features an en-suite option — a hallway door can be closed to create a completely private guest suite, ideal for visitors. The Flex/Den is a perfect space for a home office, den, hobby room, or study. Step outside to the extended lanai, complete with a remote controlled sunshade, where you'll enjoy serene pond views and the privacy of no neighbors behind — just a tranquil privacy wall framing your own lush tropical backyard retreat. For peace of mind, hurricane shutters protect the entire home. The two-car garage rounds out the package with sleek polyaspartic flooring and ample storage shelving for beach gear, tools, and everything in between. Beyond your front door, Bellacina by Casey Key delivers resort-style living at every turn. The spectacular amenity center — just a short stroll away — features a full-time Activities Director with a vibrant monthly social calendar, an elegant clubhouse with a catering kitchen and gathering room complete with a pool table, and a 24-hour fitness center. Outside, the heated resort-style pool is surrounded by private cabanas, lounge chairs, and umbrellas, complemented by an outdoor spa, two fire pits, and an outdoor grilling area perfect for gathering with neighbors and friends. Stay active with bocce ball, corn hole, four lighted pickleball courts, a Har-Tru tennis court, a playground, and scenic walking paths winding throughout the neighborhood. Two fenced dog parks and private access to the renowned Sarasota-to-Venice Legacy Trail round out an amenity package that is truly second to none. Golf carts are welcomed throughout the community, putting Nokomis Beach, nearby restaurants, shops, and local ice cream shops just a 10-minute ride away. Bellacina is also ideally positioned for exploring all that the Gulf Coast has to offer — just 5 miles from Venice Island, approximately 20 minutes from world-famous Siesta Key, and 30 minutes from downtown Sarasota and Sarasota-Bradenton International Airport. This is more than a home — it's a lifestyle. Offering the perfect blend of luxury, comfort, convenience, and coastal charm.

5749 Semolino Street, Nokomis
$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
$237,500
2 Beds ⋅ 2 Baths ⋅ Sorrento Villas SubDv. ⋅ 34275 Zip Code
Welcome to your new home in paradise. New luxury vinyl just completed 2026, fresh paint on the ceilings and walls 2025, NEW ROOF 2025, newer appliances and fixtures, one car garage and so much more. This villa is in the heart of Nokomis. Almost 1500 square feet of light, bright and airy rooms, includes two bedrooms and two baths, an open concept living and dining room, eat in kitchen as well as additional bonus space. Tranquil front and back screened porches enhance the living space. The AC was replaced in 2020, baths refreshed in 2021, garage door opener in 2023 and a whole house replumb in 2011. The community takes care of the lawn maintenance for you. Nothing left to do but move in and enjoy all the area has to offer. Close to beaches, shopping, parks and the renowned Legacy Trail. This is your chance to live the dream in warm and sunny Florida.

515 Rousseau Drive, Nokomis
$425,000
3 Beds ⋅ 2 Baths ⋅ Venice Woodlands SubDv. ⋅ 34275 Zip Code
Welcome to 184 Daylily Boulevard, a beautifully maintained home located in the highly desirable gated community of Venice Woodlands in Nokomis. Combining modern comfort, resort-style amenities, and an exceptional location, this residence offers the perfect opportunity to enjoy the best of Florida living. Step inside and discover a thoughtfully designed floor plan featuring bright, open living spaces ideal for both everyday living and entertaining. Large windows invite natural light throughout the home, creating a warm and welcoming atmosphere. Whether hosting family and friends or enjoying a quiet evening at home, this residence offers comfort, functionality, and style. Venice Woodlands is a sought-after gated community known for its beautifully landscaped surroundings and impressive amenities. Residents enjoy access to a resort-style swimming pool, fitness center, clubhouse, pickleball courts, bocce ball courts, and walking paths throughout the neighborhood. The community provides a vibrant yet peaceful lifestyle with opportunities to stay active and connected. One of the property's greatest advantages is its prime location. Just minutes away, you'll find the pristine Gulf beaches of Nokomis Beach and Venice Beach, where you can enjoy swimming, boating, fishing, paddleboarding, and spectacular sunsets. Outdoor enthusiasts will appreciate easy access to the renowned Legacy Trail, perfect for biking, walking, and jogging. Nearby attractions include historic downtown Venice, known for its charming boutiques, outdoor cafés, waterfront dining, farmers markets, and year-round community events. Golf enthusiasts will find numerous championship golf courses nearby, while nature lovers can explore Oscar Scherer State Park, Casey Key, and the area's many parks, preserves, and waterways. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers easy access to Sarasota, Venice, and all that Florida's Gulf Coast has to offer. Whether you're searching for a year-round residence, seasonal retreat, or investment opportunity, 184 Daylily Boulevard offers the perfect combination of location, lifestyle, and community amenities. Schedule your private showing today and experience the Venice Woodlands lifestyle for yourself.

184 Daylily Boulevard, Nokomis
$215,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed bedrooms, each offering ample space. Pine Run is a vibrant community that offers a variety of amenities for your enjoyment. Take a dip in one of the two community pools, perfect for cooling off on a sunny Florida day. Stay active and engage in friendly competition on the tennis courts or try your hand at pickleball. For those who enjoy the beach, you'll be delighted to discover that the condo is less than half a mile away from the Gulf of Mexico. Spend your days basking in the warm sun, strolling along the sandy shores, or indulging in water activities. Pine Run is not just a place to live, it's a lifestyle. With its picturesque surroundings, abundant amenities, and proximity to the Gulf of Mexico, this condo offers the perfect blend of tranquility and convenience.

110 Woodland Place Unit 110, Osprey
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