Osprey/Nokomis Homes with Sarasota Middle Middle School

3 Beds ⋅ 3 Baths ⋅ A4703025 MLS ⋅ 1 BLDG.

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, Osprey/Nokomis

$550,000

3 Beds ⋅ 2 Baths ⋅ A4701316 MLS

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/Nokomis

$399,000

2 Beds ⋅ 2 Baths ⋅ A4699464 MLS

Welcome to 329 Bay Vista Ave., Osprey, FL 34229—a rare opportunity to own a beautifully renovated 2-bedroom, 2-bathroom home on an expansive lot (0.47 acre!!!) with no HOA, no deed restrictions, and endless possibilities. Inside, you'll find a thoughtfully updated interior that's move-in ready, offering the perfect blend of comfort and style. Whether you're looking for a full-time residence, seasonal retreat, or investment property, this charming home provides easy, low-maintenance living in one of Osprey's most desirable locations. Situated on a generously sized homesite, this property offers the flexibility that's becoming increasingly difficult to find. Whether you've been dreaming of adding a pool, building a detached garage or workshop, parking your RV or boat, creating a garden oasis, or expanding the existing home, the space is here to bring your vision to life. Without the limitations of an association, you have the freedom to truly make this property your own. For those who love the Florida waterfront lifestyle, this location is hard to beat. Enjoy being just minutes from the Intracoastal Waterway, public boat ramps, Casey Key, Nokomis Beach, and waterfront dining, while having the added peace of mind of being outside of a flood zone. It's the best of both worlds—close to the water without the added concerns that often come with waterfront living. Conveniently located near the Legacy Trail, Oscar Scherer State Park, shopping, dining, top-rated schools, and with easy access to both Sarasota and Venice, this home combines location, flexibility, and lifestyle. Whether you're looking for your first home, a winter escape, or a property with room to grow, 329 Bay Vista Ave. delivers a unique combination of updated living, land, and freedom that's becoming increasingly rare to find. Bring your boat, your RV, your ideas, and your vision—because with this oversized lot, no HOA, and endless potential, the possibilities are truly limitless.

329 Bay Vista Avenue, Osprey/Nokomis

$238,000

2 Beds ⋅ 2 Baths ⋅ A4699074 MLS

Welcome to 404 Oxford — Maintenance-Free Living in a Prime Location This spacious villa offers the easy, low-maintenance lifestyle you've been looking for — with exterior upkeep, roof, and lawn care all handled for you. A new roof is being installed this month, and recent updates to the HVAC, hot water heater, and electrical panel mean the big-ticket items are already taken care of. Inside, you'll find a smart split floor plan with two additional flex rooms, perfect for a home office, library, or exercise space. There's no carpet throughout, an interior laundry room conveniently located just off the kitchen, and abundant closet space. The garage offers plenty of room for storage. Solid block construction adds lasting peace of mind. Step outside to quiet, walkable residential streets and frequent visits from local wildlife, all just adjacent to Oscar Scherer State Park. Ideally situated between Sarasota and Venice, you're only 10 minutes from Nokomis Beach and the Jetty, and 5 minutes from Publix, shops, and restaurants. This is not a 55+ community — a great fit for buyers of any age looking for comfort, convenience, and natural beauty right outside the door.

404 Oxford Drive Unit 404, Osprey/Nokomis

$497,000

3 Beds ⋅ 3 Baths ⋅ A4698434 MLS ⋅ Blackburn Harbor Waterfront Vi BLDG.

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/Nokomis

$237,500

2 Beds ⋅ 2 Baths ⋅ A4697128 MLS ⋅ 515 BLDG.

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, Osprey/Nokomis

$1,595,000

4 Beds ⋅ 4 Baths ⋅ A4695145 MLS

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

75 Osprey Point Drive, Osprey/Nokomis

$695,000

A4696023 MLS

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

216 Osprey Point Drive, Osprey/Nokomis

$239,900

2 Beds ⋅ 2 Baths ⋅ N6144444 MLS ⋅ 211 BLDG.

One or more photo(s) has been virtually staged. Welcome to endless sunshine, nature & Nokomis Beach, a coastal jewel in the middle of Sarasota County. This spacious second-floor corner-unit condominium offers a wonderful sense of openness with generous room sizes, split bedrooms, abundant windows throughout & excellent Outdoor Living space with two covered & screened lanais. The large 24’ x 18ft wide’ great room offers far more width & flexibility than a typical condominium floor plan. Sliding glass doors open directly to the expansive rear covered & screened lanai spanning 26 feet with amazing views of the Oscar Scherer State Park Preserve. The front covered & screened lanai is approximately 12’ x 12’ & includes a private laundry room. Both lanais have plenty of room for seating & dining areas! The primary suite includes its own private bathroom & a large walk-in closet. Both bedrooms enjoy views toward the pool area, adding to the light, cheerful, resort-style atmosphere. The kitchen offers newer appliances & a cozy breakfast nook, making this condominium equally suited for full-time living, seasonal use, or a Florida retreat. Low, affordable condo fees add to the appeal, with exterior maintenance & building/master insurance included through the association. The location is outstanding — right in Nokomis, where you can enjoy nearby shopping, grocery stores, pharmacy, dining, boutiques, Ace Hardware, & everyday conveniences. You are also super close to both bridges leading to renowned Casey Key, where waterfront dining, tiki bars, live music with dancing, boating, beaches, & the best of the coastal lifestyle await. The historic Island of Venice is just minutes away & offers something for everyone, including the popular weekly Farmers Market, art shows, boutique shopping, outdoor dining, live music, community events, & the charming walkable atmosphere that has made Venice one of Florida's most beloved coastal towns. The impressive Sarasota Memorial Hospital campus is close by, I-75 is convenient with no red light to the interstate via the expressway, & the location is well positioned for easy access to Sarasota, Tampa, Punta Gorda, & all area airports. Come live on vacation in this terrifically vibrant community & enjoy the lifestyle!

211 Rubens Drive Unit E, Osprey/Nokomis

$299,990

2 Beds ⋅ 2 Baths ⋅ A4694926 MLS ⋅ 22 BLDG.

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

4296 Expedition Way Unit 104, Osprey/Nokomis

$4,790,000

4 Beds ⋅ 6 Baths ⋅ A4694716 MLS

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

101 Osprey Point Drive, Osprey/Nokomis

$749,000

3 Beds ⋅ 2 Baths ⋅ A4690813 MLS ⋅ Building C BLDG.

Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

280 Hidden Bay Drive Unit 302, Osprey/Nokomis

Osprey/Nokomis Homes with Sarasota Middle Middle School

Newest Osprey/Nokomis Homes with Sarasota Middle Middle School