Homes For Sale in Osprey 34229 - 125 homes

Remarks: Under contract-accepting backup offers. Under contract- accepting backup offers. Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan and spacious living areas designed for comfortable everyday living and effortless indoor - outdoor flow. The private screened lanai overlooks the expansive lake and includes a pool, creating a peaceful setting to relax and enjoy Florida’s outdoor lifestyle. Many homes in the community are positioned along narrower sections of the lake, making this view especially appealing. The primary suite offers two walk-in closets, along with a bath featuring both a soaking tub and separate shower. The interior is original and presents an opportunity for a new owner to update and customize to their personal style. Recent improvements include a five year old air conditioning system and one year old water heater. Willowbend is a maintenance-free community with lawn care, landscaping, irrigation and internet included, conveniently located near the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, and Pine View School. Residents enjoy living in a beautifully established setting surrounded by lakes, preserves, and mature landscaping. Willowbend offers a community pool and spa, tennis and basketball courts and playground. This property offers strong value for its location, view, and private pool, and is ready for its next owner to make it their own.

Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)

Listing Agent: Margot Leonard (941-387-5050)

Remarks: This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Todd Currey (941-402-6000)

Remarks: Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant sunsets. Gourmet kitchen with natural gas range, stainless dishwasher and refrigerator (new 2026). The interior boasts custom features, including crown molding and elegant tray ceilings. This spacious four-bedroom, three-bath home includes a chef's kitchen outfitted with natural gas cooking, as well as a cozy eat-in area with an aquarium window that beautifully frames the pool and lake views. The owner's suite serves as a sanctuary, offering two walk-in closets and a luxurious bath complete with dual sinks, a walk-in shower, a soaker tub and a separate toilet for added privacy. Thoughtfully designed with a split floor plan, the home ensures guests enjoy ample separation from the owner's suite for optimal comfort. A full-size laundry room adds to the home’s convenience. This exceptional residence is a blank canvas for an extraordinary lifestyle, conveniently near downtown Venice and Sarasota, beautiful beaches, Pine View School and the Legacy Trail. With no CDD fees and in a preferred X flood zone, the low community fees cover ground maintenance, irrigation and access to a community pool and spa, gym, pickleball courts, as well as high-speed internet and DirecTV streaming. Embrace the lifestyle you’ve always dreamed of in this stunning Willowbend home.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Todd Currey (941-402-6000)

Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!

Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)

Listing Agent: Mariana Georgieva (941-809-0416)

Remarks: One or more photo(s) has been virtually staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. Some of the Photos are virtually staged. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.

Listing is courtesy of: EXIT KING REALTY (941-497-6060)

Listing Agent: Tim Weller (941-221-0155)

Remarks: MOTIVATED SELLER. Bring an offer! Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers 2,374 sq ft of well-appointed living space, and water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a DEEDED 40' wet slip—($125,000 value) providing immediate access to boating, fishing, and the Intracoastal Waterway. This home features high ceilings, brand new flooring throughout, an open layout, and a spacious kitchen with premium cabinetry and high-end appliances. The large living and dining areas flow seamlessly onto a covered balcony that overlooks the marina and bay—perfect for sunset views and outdoor dining. The primary suite is a true retreat with water views, balcony access, and a brand-new designer bathroom with a spa soaking tub, rain shower with bench seating, under-floor lighting, and modern double vanities. Residents enjoy a private, resort-style atmosphere with a heated bayside pool and spa, clubhouse, fitness center, sauna, billiards, BBQ grills, and a full-service marina. Ideally situated between Sarasota and Venice and minutes to Midnight Pass beach, this location offers easy access to waterfront dining at Casey Key Fish House and Deep Lagoon, nearby parks, and all the coastal conveniences of Osprey. This is a rare opportunity to own a spacious waterfront condo with refined interiors, exceptional views, two assigned parking spot, and a dedicated 40’ slip—all within a beautifully maintained, luxury marina community. New Metal Roof on all buildings Oct 2025, AC replaced in 2020, new kitchen and bathrooms in 2024, brand new luxury vinyl flooring replaced January 2026.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Kelli Eggen (941-376-9844)

Remarks: One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. There is a community pool where you can enjoy a refreshing swim or relax poolside. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)

Listing Agent: Kimberly Werla, Pa (941-979-2757)

Remarks: One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.

Listing is courtesy of: ROBERT SLACK LLC (352-229-1187)

Listing Agent: Debbie Baraona (941-350-8723)

Remarks: Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway just a few homes down the canal. A true boater’s dream, your private dock provides quick and easy access to some of the area’s most beloved waterfront destinations. Cruise north to Casey Key Fish House, or the newly reopened Midnight Pass. You could also head south toward Venice to enjoy Pop's Sunset Grill and Pelican Alley. Spend your days at Snake Island, or venture through the jetties to the open waters of the Gulf of Mexico —where the possibilities for exploration are endless. Inside, the home features a spacious and flexible floorplan with a kitchen, dining room, living room, and den, along with an indoor laundry room. Two of the three bedrooms are private ensuites, offering ideal comfort for guests or multi-generational living. The home is being offered turnkey (with select personal exclusions), making it move-in ready for immediate enjoyment or seasonal use. Step outside to your impressive 27x40 enclosed lanai with pool, creating an expansive outdoor living space perfect for entertaining or unwinding in your own private tropical setting. In addition to the 2-car garage, a large storage shed provides added convenience, and there is dedicated space to park your boat trailer right on the property—no off-site storage needed. Major updates provide peace of mind: New roof -July2025, 3rd nail installed in rafters-July 2025, Pool Heater (Electric)-December 2025, New Pool Cage (Picture frame)- January 2025, Primary bath remodeled- August 2025, Guest Bath (partial remodel)-August 2025, Interior painted-September 2025, Popcorn ceiling removed and ceiling painted-August 2025. New Septic System-2024 Sewer pipes lined-2023/2024 New water heater-2024 A/C (2018) Sorrento Shores is a hidden gem offering a voluntary HOA of just $125/year and no CDD fees, delivering a relaxed coastal lifestyle without the burden of high community costs. Whether you’re searching for a winter retreat, full-time residence, or investment opportunity, this property stands out with its rare combination of quick Intracoastal access, expansive lot size, private dock, and prime location.

Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)

Listing Agent: Phyllis Coviello (941-408-3265)

Remarks: Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Edward Bieker, Pa (941-525-6473)

Remarks: Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include 2026 irrigation valves, 2025 roof replacement, 2024 pool pump and a 2017 air conditioning system, providing peace of mind for years to come. Go onto the inviting front porch, the ideal setting for morning coffee. Enter through the elegant glass front door into a bright, open foyer filled with natural light. The spacious split floor plan seamlessly connects the great room, formal dining room, kitchen, and cafe, creating an ideal layout for everyday living and entertaining. The chef’s kitchen is beautifully updated with granite countertops, stainless steel appliances, custom wine racks, rich cabinetry, a built-in desk, pantry and breakfast bar. The adjacent cafe features a stunning aquarium window overlooking the sparkling heated pool, an ideal spot for casual meals before heading to the beach. The generous primary suite is a private retreat, offering dual walk-in closets, sliding glass doors to the lanai, and a luxurious en-suite bath complete with solid wood cabinetry, granite countertops, dual sinks, a soaking garden tub, walk-in shower, linen closet, and private water closet. On opposite side of the home, guests will enjoy their own private wing with two bedrooms and a full bath separated by a pocket door. The third bedroom features built-in cabinetry and offers wonderful flexibility, easily functioning as an additional office, study, or peaceful reading retreat. The fourth bedroom at front of the home is suited as a den, office or playroom. The spacious laundry room offers a utility sink, additional cabinetry and ample storage. Outdoor living shines in the screened lanai and beautifully updated paver pool area. The fenced area is ideal for pets, and the expansive patio provides a backdrop for relaxing or hosting gatherings. Rivendell residents enjoy low HOA fees that include lawn and shrub care, a heated community pool, playground and scenic recreational trails all with no CDD fees. The irrigation system is connected to a private well, providing an efficient and cost-effective way to maintain the lush tropical landscaping year-round. This neighborhood offers a private path to Pine View School for the Gifted and borders Oscar Scherer State Park and 200 acres of preserved land. Outdoor enthusiasts will appreciate easy access to the Legacy Trail. Ideally in south Sarasota, this serene enclave offers convenient access to pristine Gulf beaches and sits between Sarasota and Venice for exceptional dining, shopping and cultural attractions. Furnishings are available for purchase!

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)

Listing Agent: Crystal Cosby, Llc (941-882-0070)

Remarks: Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Steve Abbe (941-400-3969)

Remarks: **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a nearby golf course, offering tranquil views and peaceful surroundings. With no rear neighbors, you'll enjoy the privacy and serenity that your 1 acre+ lot affords. Have a boat or RV? This community is deed restricted but there is plenty of space to build an oversized garage to house vehicles or create a dream workshop. Inside, you'll find a timeless blend of comfort and sophistication. The spacious interior boasts high ceilings, large windows that fill the rooms with natural light, and an open floorplan that seamlessly connects the living spaces. Nestled amid lush greenery and serene surroundings, this property stands out as more than just a house—it's a haven awaiting its next resident. Designed with both comfort and elegance in mind, every detail speaks to a lifestyle where relaxation and convenience coalesce effortlessly. Step inside, and you'll discover a space that beckons you to make it your own sanctuary. Located in a quiet, upscale neighborhood with a charming, country-like feel, this home is just minutes from everything that makes Sarasota County one of Florida’s most sought-after destinations. The world-renowned Nokomis Beach and Siesta Key, are a short drive away, offering sun, surf, and sand any time you desire. Pine View School, consistently ranked among the top public schools in the nation, is only a few minutes away. Outdoor enthusiasts will love the easy access to the Legacy Trail, a scenic multi-use path perfect for biking, running, and leisurely strolls through nature preserves. Whether you're looking to settle into a peaceful primary residence or seeking a second home close to golf, beaches, and top-tier schools, this home offers the perfect balance of nature, convenience, and lifestyle. The home features 5 bedroom and 3.5 bathrooms, and an oversized 2 car garage. The open concept floorplan and expansive covered patio are perfect for entertaining. The main master suite has vaulted ceilings, sliding glass doors leading to the pool and spa, an oversized walk-in closet, and the bathroom is plumbed for a soaker tub. On the other side of the home there are 4 more bedrooms, one of which also has an en-suite bathroom. For added peace of mind, this home comes with many newer updates such as: Roof 2016, Pool heater 2024, Septic tank 2024. Both HVAC units and Pentair pool Wi-Fi controlled equipment have been updated and home has been replumbed with CPVC. Call today to schedule a showing before this home is gone! Property is in Probate.

Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)

Listing Agent: Deborah Frederick (941-544-6493)

Remarks: Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!

Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)

Listing Agent: Sharon Lewis (941-966-5400)

Remarks: Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village- 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. With new metal roof, exterior and interior paint completed in 2025, this property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Veronica Lee (609-651-0305)

Remarks: One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Toni Zarghami (941-248-2147)

Remarks: Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Natalie Gutwein (941-993-2660)

Remarks: This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pullouts and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking, or your gourmet meal preparation, a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your primary retreat vie for your attention thanks to the shimmering intracoastal front and center. Generous in size, the main retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are under the building and out of the elements, adding to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, and fishing. Boat slips are available on a first-come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path and pretty greenspace areas. Ideally close to shopping, dining, the crystal sand beaches and famed Oscar Scherer State Park, which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming, and the best part is the proximity, just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Cindy Migone (941-812-7438)

Remarks: 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.

Listing is courtesy of: GALLERY PROPERTIES INTERNATION (941-957-0833)

Listing Agent: William Fortner (941-915-4045)

Remarks: Welcome to this beautiful home in the sought-after Rivendell community. The curb appeal is evident as you drive up to this home, from the landscape and the paver driveway to the beautiful front door. As you step inside the wide foyer, your view extends out through the sliders leading out to the pool and lanai. This well-maintained updated residence combines a bright, inviting interior designed for everyday living and entertaining. Neutral colored tiles extend throughout the kitchen, breakfast nook, dining and living areas. The kitchen is to the left of the dining and living area and offers generous counter space for all your preparation and cooking needs. The primary bedroom suite is spacious with sliders to the lanai and a large walk-in closet with a deluxe custom organizer. The ensuite bathroom has both a tub and a walk-in shower with a long vanity with two sinks and a makeup area in the middle. The remaining bedrooms and bathroom are on the other side of the house offering privacy for daily life or entertaining. Enjoy outdoor living at its finest with your private, heated pool and a backyard that offers desirable privacy — perfect for relaxing or hosting guests year-round. Recent major upgrades provide peace of mind, including a new Novatik metal roof (2025) along with new fascia, soffits, and gutters. The home also features an updated HVAC system (2023) and impact windows and doors everywhere with a motorized Kevlar hurricane shutter for the lanai. Rivendell is a beautiful 400-acre community with parks, trails, and a community pool located in Osprey. It is in close proximity to Pine View School. It is between charming Venice and vibrant Sarasota, so you'll enjoy a rich array of shopping, dining, and cultural experiences. Within a few miles, you can be at the world-famous Siesta Key Beach to swim or relax on the beach. Or head south a few miles to the more secluded Nokomis Beach and North Jetty Beach. This location truly offers easy access to the best of coastal living. For outdoor enthusiasts, Legacy Trail Osprey Junction Trailhead is nearby as is Oscar Scherer State Park. Explore the natural beauty of the region at your own pace while biking or walking, taking in the lush scenery and tranquil surroundings. Don’t miss the opportunity to own this thoughtfully upgraded home in one of Osprey’s most popular communities.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-485-5421)

Listing Agent: Janet Oberholtzer (484-798-7824)