Location: Osprey
Keyword(s): Venice Senior High
Keyword(s) High School: Venice Senior High
Do Not Show Listings
3936 WAYPOINT AVE, OSPREY, FL 34229
$1,039,00014 Days on yellowkey MLS ID: A4687847
0 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2323 Built: 2016Monthly Fee: $521 Tax: $10,336 (2024)Community: BaysideSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,336
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Discover coastal-inspired living at its finest in this exquisite lakefront home nestled within **Bayside**, an exclusive Taylor Morrison-built community of just 49 meticulously landscaped, maintenance-free residences. As you step inside, your eyes are immediately drawn through the expansive great room to breathtaking water views that capture the essence of waterfront living. The great room offers generous space for both elegant entertaining and relaxed everyday enjoyment, enhanced by tray ceilings and elegant crown molding—among the many thoughtful upgrades found throughout the home. The gourmet kitchen is a standout, featuring quartz countertops, a large closet pantry, premium GE Monogram appliances, an LG refrigerator, and a spacious island with counter seating and dual sided cabinets. This space overlooks the lanai and pool, creating a seamless indoor-outdoor flow. Outside, the lanai is truly exceptional—an entertainer’s dream with a fully equipped outdoor kitchen, a cozy gas fireplace, both covered and open seating areas, and a sparkling saltwater pool and spa with gas heater. All of this is beautifully framed by a brand-new 2025 panoramic screen enclosure, offering sweeping views of the lake and abundant wildlife. The primary suite is a private retreat with stunning lake views with a luxurious bath featuring a spacious walk-in shower and a full wall vanity with dual sinks. The expansive walk-in closet includes custom built-ins for maximum storage and organization. A thoughtful split-bedroom plan ensures privacy, with Bedroom 2 offering an ensuite bath, Bedroom 3 conveniently located near the main bath, and a spacious den/office providing flexible living options. Additional practical features include a well-appointed laundry room with ample cabinetry and a garage equipped with its own split HVAC system. Bayside residents enjoy exclusive access to a private waterfront park overlooking the Intracoastal Waterway, with panoramic views of Casey Key and spectacular sunsets. This open space includes a day dock, kayak and paddleboard launch, fire pit, and generous lawn area—perfect for relaxing or gathering with friends. Located west of the trail with direct water access, this rare combination of lifestyle and location is nearly impossible to find. Homes like this don’t last long. Don’t let this one get away!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larry Brzostek (941-993-3125)
242 HIDDEN BAY DR #602, OSPREY, FL 34229
$719,00082 Days on yellowkey MLS ID: A4678883
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1932 Built: 1999 Tax: $7,518 (2025)Community: Baypointe Vista 1Condo
Taxes:$7,518
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior. The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use. The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence. The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference. Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.
Listing is courtesy of: FIRST LIGHT REAL ESTATE (941-650-2256)
Listing Agent: Cathy Rustin (941-650-2256)
353 S SHORE DR, OSPREY, FL 34229
$1,200,00014 Days on yellowkey MLS ID: A4688006
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $10 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Single Family
Taxes:$3,904
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 (2025) A/C (2018) Sewer pipes lined (2024) Water heater (2024) New pool heater (Dec 2025) 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)
437 S SHORE DR, OSPREY, FL 34229
$525,00021 Days on yellowkey MLS ID: N6143587
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1947 Built: 1976Monthly Fee: $10 Tax: $4,187 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,187
Remarks: Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about. Discover the possibilities in this home that sits on a generous 19,500 (ALMOST ½ ACRE) square foot lot, providing ample space to stretch out, play, and grow. Step outside and enjoy the expansive, enclosed over-sized lanai and host gatherings all while overlooking your own backyard paradise. Inside, multiple large sliding glass doors effortlessly blend the indoor and outdoor spaces, inviting the sunshine to fill your home. The home features three spacious bedrooms, 2 bathrooms, multiple living spaces, and 2-car attached garage. Recent updates bring peace of mind: NEW ROOF (2025) and HVAC SYSTEM (2025). Also, enjoy the IRRIGATION SYSTEM that runs off a private well to keep your lawn green. This home is also perfectly positioned to enjoy the best local amenities. You’ll find the stunning Oscar Scherer State Park just moments away, offering miles of trails for hiking and birdwatching. The famous Legacy Trail is nearby, ideal for cycling or a leisurely stroll through the scenic landscape. When you're ready to soak up the sun, Nokomis Beach is just a short drive away, perfect for sand, surf, and sunsets. And when it’s time to dine out, you’re surrounded by a variety of waterfront restaurants offering delicious meals with views to match. It’s the ultimate blend of peaceful living and easy access to everything you need for relaxation and adventure.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Dawn Barnett (317-281-8194)
365 S SHORE DR, OSPREY, FL 34229
$1,380,000104 Days on yellowkey MLS ID: N6142101
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1824 Built: 1968 Tax: $7,804 (2025)Community: Sorrento ShoresSingle Family
Taxes:$7,804
Remarks: Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined home remains unaffected by flooding AND IN FLOOD ZONE X, unfolds safely toward the water where EXPANSIVE BAY WINDOWS frame uninterrupted scenery. Step out your back door and hop on your boat for effortless days on the water in a premium location. FULLY FURNISHED! Offering 3 BEDROOMS, 2 FULL BATHROOMS, and 1,846 square feet of true Florida living, this home’s PANORAMIC VIEWS flood it with natural light and blur the line between indoors and out. PGT IMPACT WINDOWS, ELECTRONIC SHUTTERS, rich WOOD PANELING, and CROWN MOLDING lend architectural depth and timeless coastal sophistication, creating a home that feels calm, luminous, and deeply connected to its surroundings. The kitchen features QUARTZ countertops, a GRANITE COMPOSITE SINK, and UPGRADED FIXTURES. CEDAR-accented guest bedroom ceilings, CUSTOM built-in closets throughout, and NEW LIGHTING reflect thoughtful stewardship. ADDITIONAL UPGRADES include a new REVERSE OSMOSIS WATER FILTERATION SYSTEM AND WATER HEATER (2023) and AIR DUCTS (2025). Outdoor living is the centerpiece. The PRIVATE DOCK AND OUTDOOR FIRE PIT are natural extensions of the home, inviting morning coffee, sunset cocktails, and manatee sightings. Boat amenities were meticulously maintained with NEW MOTOR CAPACITORS (2023), and BOAT LIFT CABLES AND DOCK LIGHTS (2024). Lush landscaping in the GENEROUS FRONT YARD enhances curb appeal, while mature trees provide tropical PRIVACY, with plenty of room for a POOL. Homes with this DEPTH, PRIVACY, and INTRACOASTAL ACCESS are RARELY available. This is not simply a WATERFRONT HOME – it is a BOATING LIFESTYLE defined by light, movement, and an ever-changing horizon. Just a 2 minute boat ride to the Intracoastal Waterway, 25 minutes to the Gulf of Mexico and 10 minutes to Casey Key Fish House and Tiki Bar! Call for a private tour of this beauty!
Listing Agent: Lisa Asaro (941-725-8626)
479 SOUTH CREEK DR, OSPREY, FL 34229
$2,495,000135 Days on yellowkey MLS ID: N6141722
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4261 Built: 1995Monthly Fee: $150 Tax: $11,095 (2024)Community: South CreekSingle Family
Taxes:$11,095
Remarks: Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 7,000-pound boat lift and a DEDICATED KAYAK LAUNCH, creating seamless access to the Intracoastal lifestyle. Inside, five generously sized bedrooms each feature ensuite baths and large walk-in closets, with two bedrooms conveniently located on the first floor along with a dedicated office, den, or bonus room. The renovated kitchen is designed for both beauty and function with a Thermador cooktop, Jenn- Airconvection and built-in ovens, a large island, and a passthrough window for effortless outdoor entertaining. The dining area overlooks the pool and includes hurricane-impact sliding doors, a coffee or dry bar with mini-fridge, and additional custom cabinetry for storage. The living room is highlighted by soaring ceilings, transom windows, additional hurricane impact sliding glass doors, and charming shiplap ceiling details, creating a light-filled coastal ambiance. Upstairs, three additional bedrooms and a loft gathering area overlook the living space below, with the true primary suite on the second level along with two waterfront-view bedrooms, all featuring ensuite baths and generous closets, plus a second-floor laundry hookup for added convenience. A spacious three-car garage and elegant U-shaped driveway complete the home. This home has been replumbed and features new lift motors (2025). Located within a gated community offering a basketball court, day dock, playground, and low HOA fees, this property is just 5 miles to Nokomis Beach on Casey Key, 15 miles to downtown Sarasota, 6 miles to the Island of Venice, and 6 miles to Sarasota Memorial Hospital, with Oscar Scherer State Park right nearby for nature lovers and outdoor enthusiasts.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
597 OAK RIVER CT, OSPREY, FL 34229
$699,000129 Days on yellowkey MLS ID: A4673797
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2111 Built: 1994Monthly Fee: $25 Tax: $5,289 (2025)Community: Bay Oaks EstatesSingle Family
Taxes:$5,289
Remarks: Under contract-accepting backup offers. Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator, 42-inch white shaker cabinetry, wet bar, and wine cooler. The expansive living area impresses with approximately 15-foot vaulted ceilings and a dramatic 15-foot custom built-in fireplace. Both bathrooms have been luxuriously remodeled with floor-to-ceiling tile, rainfall showers with modern glass enclosures, floating vanities, upgraded shower fixtures with handheld sprayers, Kohler toilets, Bluetooth smart fans with built-in speakers, ambient lighting, and a free-standing soaking tub. The primary suite features a sleek barn door, and interior pocket doors have been updated throughout. The fourth bedroom, currently used as an office, features 12-foot ceilings and a custom Murphy bed with an integrated, tailor-made IKEA PAX closet system. Durable, stylish LVP flooring runs throughout the home. Step outside to your brand-new 36' x 12' saltwater pool and spa (completed in 2024) featuring a sun shelf, heating and cooling system, top-of-the-line Jandy equipment, variable-speed pump, and sandblasted marble decking. Pre-installed footers allow for a future pool cage if desired. Maintaining a lush, "envy-of-the-neighborhood" lawn is effortless and cost-effective thanks to the private irrigation well, which has been completely overhauled with brand-new wiring, new pipes, and new sprinkler heads. Significant structural and mechanical upgrades include a new AC system in 2018, updated CPVC plumbing, LED can lighting, and multiple hurricane-impact upgrades, including the front, pool bath, and garage side doors. The air conditioned garage has an upgraded side mount garage opener with smart video door bell, plus a premium impact-rated garage door. All openings except windows have been storm-reinforced. The property is fully enclosed with white vinyl fencing and offers an irrigation well for low-cost landscape watering. This meticulously renovated residence blends modern luxury, functionality, and exceptional craftsmanship; offering a truly move-in-ready home just moments from the highly desired Legacy Trail, perfect for biking, walking, and outdoor recreation.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
447 N SHORE DR, OSPREY, FL 34229
$515,35041 Days on yellowkey MLS ID: A4684009
REDUCED by $19,550 (3.7%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing Agent: Lauren Sisco (904-652-9387)
1016 SCHERER WAY, OSPREY, FL 34229
$950,00017 Days on yellowkey MLS ID: A4687161
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2921 Built: 2003Monthly Fee: $115 Tax: $5,442 (2025)Community: Rivendell Unit 5 The WoodlandsSingle Family
Taxes:$5,442
Remarks: Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings. The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!
Listing Agent: Rachel Tritschler (941-993-5892)
6100 JESSIE HARBOR DR #203, OSPREY, FL 34229
$699,00059 Days on yellowkey MLS ID: N6142959
0 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2630 Built: 2005 Tax: $6,713 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$6,713
Remarks: BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of only 15 residences. BEING SOLD WITH FURNITURE except for a couple of personal items. The spacious floor plan features over 2,600 square feet of well-designed living space with 3 bedrooms, 3 baths, and flexible areas ideal for a den, office, or entertaining. A welcoming foyer, breakfast area, and expansive living room all showcase stunning, eye-level water views, while the large lanai is perfectly positioned for sunsets, birdlife, dolphins, and passing boats along the Intracoastal Waterway. The chef’s kitchen is both functional and elegant, featuring exquisite granite countertops, custom cabinetry with soft-close pullouts, and ample workspace for everyday living and entertaining. Interior upgrades include tile flooring, plantation shutters, remote-controlled blinds, higher ceilings, a built-in bar, and generous closet space throughout. The primary suite serves as a private waterfront retreat with beautiful Intracoastal views, custom closets, and a spa-style bath with a walk-in shower, soaking tub, dual vanities, makeup area, and private water closet. Guest baths are thoughtfully designed for comfort and convenience. Boating enthusiasts will appreciate water access and protected dockage, with boat slips available on a first-come, first-serve basis and currently no waiting list, accommodating vessels up to approximately 39 feet. With no bridge access and only minutes to open water and the Gulf, this location is ideal for cruisers and avid boaters seeking quick, easy Intracoastal and Gulf access. Additional features include two assigned parking spaces, one in the under-building garage and one covered carport, private unit storage, EV charging capability, an interior laundry room with sink and cabinetry, newer washer and dryer, newer hot water heater, impact-rated sliders, and a new 2025 roof with no upcoming assessments. Residents enjoy resort-style amenities including a heated pool, tennis and pickleball courts, clubhouse with fitness area, kayak storage and launch, fishing, waterfront gazebo with grills, walking paths, and lush greenspace. Located directly across from Oscar Scherer State Park and near the Legacy Trail, the community offers easy access to biking, hiking, kayaking, and outdoor recreation. Perfectly positioned between Sarasota and Venice, this prime Osprey location is approximately 15 minutes to Downtown Sarasota, about 10 minutes to Historic Venice Island, and just minutes to Nokomis Beach, Venice Beach, Casey Key, and Siesta Key. Close to hospitals, medical facilities, marinas, golf, dining, and shopping, this residence offers the ideal blend of waterfront luxury, boating convenience, and low-maintenance coastal living.
Listing is courtesy of: HOMESMART (407-476-0461)
Listing Agent: Scott Swonger (941-600-3534)
3603 N POINT RD #202, OSPREY, FL 34229
$699,0001013 Days on yellowkey MLS ID: A4575407
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3147 Built: 2007Monthly Fee: $400 Tax: $4,135 (2022)Community: Meridian At The Oaks PreserveCondo
Taxes:$4,135
Tax Year: 2022
Remarks: **ELEGANT and SPACIOUS CORNER CONDO UNIT – NEARLY 3200sf – With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned Parking spaces including 1 under building, Climate-controlled storage and much more! Crown moldings, engineered hardwood floors, expansive kitchen with granite counters and stainless steel appliances are among the many beautiful appointments throughout this impressive residence. A Serene and Private Preserve setting may be enjoyed from multiple screened balconies -- with extra feature of automatic (remote controlled) hurricane shutters. NEW(er) HVAC (2021). 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. **MUST SEE**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
1801 HIGHLAND RD, OSPREY, FL 34229
$299,900211 Days on yellowkey MLS ID: N6140508
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1165 Built: 1999Monthly Fee: $150 Tax: $2,578 (2025)Community: Towns-End ShoresTownhouse
Taxes:$2,578
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)
250 HIDDEN BAY DR #302, OSPREY, FL 34229
$650,000274 Days on yellowkey MLS ID: A4657042
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1937 Built: 2017Monthly Fee: $1,558 Tax: $5,249 (2024)Community: Hidden BayCondo
Taxes:$5,249
Remarks: ANOTHER PRICE IMPROVEMENT!!!!WHAT A VIEW and the pictures don't do it justice!! SELLER IS OFFERING to prepay three (3) months of HOA dues on behalf of the buyer at closing. FULLY FURNISHED/TURNKEY UNIT! (optional of course) Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful barrier island of Casey Key. Welcome to Edgewater at Hidden Bay — a gated, 12-acre resort-style community perfectly positioned between the charm of historic Venice and the cultural vibrancy of downtown Sarasota. This impeccably maintained three-bedroom, two-bathroom plus den residence offers panoramic water views and an easy, elegant coastal lifestyle. Step inside to a bright, open-concept layout with a spacious living and dining area — perfect for entertaining or relaxing while soaking in the scenery. The gourmet kitchen is a chef’s dream, featuring stainless steel KitchenAid appliances, granite countertops, 42” real wood cabinetry, counter-height seating, and abundant storage. Coffered ceilings and 5-inch baseboards add refined architectural detail throughout. The expansive primary suite is a tranquil retreat with direct access to the balcony, dual walk-in closets, and a spa-inspired bathroom boasting dual vanities and a glass-enclosed shower. A split bedroom layout offers optimal privacy, while the full-size laundry room includes built-in cabinets and a sink for added convenience. Additional highlights include Kohler plumbing fixtures, hurricane-impact windows and doors, and an abundance of natural light throughout. Offered furnished, this home is move-in ready. Edgewater at Hidden Bay delivers exceptional amenities: a heated resort-style pool and spa, clubhouse with catering kitchen and library, fitness center, tennis and pickleball courts, kayak launch and storage, scenic boardwalk through lush mangroves, and a private fishing pier (currently being rebuilt). Enjoy unmatched access to award-winning beaches (just 6.5 miles to both Siesta Key and Nokomis Beach), Bay Street Park, Legacy Trail, Oscar Scherer State Park, shopping, dining, marinas, golf, and premier medical facilities. This is more than a home — it’s a lifestyle. Schedule your private showing today and discover the very best in waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Merryl Koven (941-526-5913)
742 HARMS DR, OSPREY, FL 34229
$515,000197 Days on yellowkey MLS ID: A4666421
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1981 Tax: $5,620 (2024)Community: Harms SubSingle Family
Taxes:$5,620
Remarks: Beautifully renovated and now offered at a newly reduced price, this turnkey property is a fantastic opportunity with motivated sellers. Set on just over half an acre along a private, tree-lined street the home is surrounded by lush tropical landscaping that creates a peaceful and secluded feel. Inside you’ll find a spacious layout with modern finishes and seamless indoor-outdoor living with a heated pool and screened lanai. The home has been fully updated and has a strong history as a successful income-producing rental. Major improvements include a full interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), HVAC (2023), and water heater, well pump, and garage door opener (2024), plus an automated pool cleaner and septic flush (2025). Ideally located between Sarasota and Venice, you’re just minutes from beaches, dining, and shopping. Oscar Scherer State Park sits directly across the street for nature trails and birdwatching, and Legacy Trail (Osprey Junction Trailhead) is only three minutes away, making this a great spot for outdoor enthusiasts. With NO HOA and plenty of space for a boat or RV, this property offers updated comfort, privacy, and flexibility perfect as a full-time home, seasonal retreat, or investment.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Tiffany Stonis (941-204-5239)
448 E MACEWEN DR, OSPREY, FL 34229
$2,100,00018 Days on yellowkey MLS ID: A4687195
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3768 Built: 1998Monthly Fee: $142 Tax: $9,639 (2025)Community: OaksSingle Family
Taxes:$9,639
Remarks: **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
252 SUN AIR CIR, OSPREY, FL 34229
$225,00054 Days on yellowkey MLS ID: A4683143
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1979Monthly Fee: $215 Tax: $1,087 (2025)Community: ArborsManufactured Home
Taxes:$1,087
Remarks: Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz countertops, a striking stone backsplash, center island, pantry, and plenty of prep and storage space. The open floor plan seamlessly connects the kitchen to the dining area and spacious family room, perfect for gatherings or relaxed everyday living. The spacious primary suite offers a walk-in closet and an updated ensuite bath complete with dual sinks in a new vanity, newer lighting and mirror, and a walk-in shower. The guest bedroom is versatile and inviting with a convenient Murphy bed, while the second bath has been tastefully updated with a tub/shower combination, new vanity lighting, and mirror. Enjoy Florida’s sunshine year-round in the bright Florida room filled with loads of windows, or unwind on the screened, enclosed lanai. Plantation shutters throughout the home. Additional highlights include a utility shed with washer and dryer, non-skid surface in lanai and driveway. Major system updates for peace of mind include a 6-year-old roof with transferable warranty, newer A/C, tankless hot water heater, 98% plywood subflooring, and cement board subfloor in the kitchen and dining room. Located in the desirable Arbors community in Osprey, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. This fully furnished, move-in ready home blends quality upgrades with relaxed Florida charm. Schedule your private showing today and start enjoying the lifestyle you deserve!
Listing Agent: Karen Geiger (941-928-8889)
234 PALM AIR DR, OSPREY, FL 34229
$120,00022 Days on yellowkey MLS ID: A4687365
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 987 Built: 1984Monthly Fee: $215 Tax: $1,338 (2025)Community: ArborsManufactured Home
Taxes:$1,338
Remarks: Welcome to The Arbors, a highly sought-after 55+ resident-owned community in Osprey known for its active lifestyle, friendly atmosphere, and prime location. This well-maintained 2 bedroom, 2 bathroom double-wide mobile home is being offered completely turn-key, with furnishings included if desired, making for an easy, move-in ready experience from day one. Inside, you’ll find a bright and inviting layout with a spacious, open-concept living and dining area that provides plenty of room for both relaxing and entertaining. The kitchen sits at the center of the home and features a functional island with seating, creating a natural gathering space and easy flow throughout the main living areas. The layout offers a seamless transition from the main living space to both bedrooms, with the primary suite positioned toward the rear of the home and featuring its own ensuite bathroom. The second bedroom and additional full bath are conveniently located nearby, making the layout practical and efficient for both everyday living and hosting guests. A spacious screened-in lanai extends your living space outdoors, perfect for enjoying the Florida lifestyle year-round. Outside, a brand new carport provides covered parking along with extra space for guests, and the attached shed includes a washer and dryer for added convenience. Located in the pet-friendly section of the community, this home is a great option for those looking to bring their furry companions. The Arbors offers an impressive array of amenities, including a heated community pool, clubhouse, library, fitness area, shuffleboard courts, kayak storage, and a grilling area. Residents enjoy a full calendar of social events, creating a vibrant and connected community atmosphere. As a resident-owned community, The Arbors is thoughtfully maintained with a strong sense of pride throughout. The low monthly fee includes water, sewer, trash, cable, internet, and lawn care, making for easy, low-maintenance living. Ideally located just off US-41, you are within walking distance to Publix and close to shopping, dining, and the beautiful Gulf beaches. Opportunities in this community are limited, making this a great chance to enjoy the best of Osprey living. **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)
180 LOOKOUT POINT DR, OSPREY, FL 34229
$2,249,900151 Days on yellowkey MLS ID: A4672222
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3236 Built: 1986Monthly Fee: $204 Tax: $8,750 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$8,750
Remarks: One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this never-lived-in five-bedroom, 3.5 bath, 3,236-square-foot home blends solid block construction with high-end design and cutting-edge technology. No detail was overlooked, including a standing seam metal roof, all new high-velocity impact windows, hurricane-rated garage doors and fully integrated Alexa features throughout. Wide-plank wood floors lead through a thoughtfully designed layout featuring custom built-ins including a kitchen desk, mudroom storage, dining room bar with wine refrigerator and living room shelving with glass doors. The kitchen is a showstopper with two large quartz islands, top-of-the-line Thermador appliances, a microwave drawer, concealed refrigerator, gas range with double ovens and a custom glass-door butler’s pantry. French doors at the entry feature Alexa-controlled electronic glass for your choice of instant privacy or transparent green views, while oversized sliders in the main living area fully retract for seamless indoor-outdoor living. The massive laundry room is a dream with two washers, two dryers, abundant storage and countertop space. Outside, enjoy a stunning new saltwater pool with cage, paver decking, and a state-of-the-art outdoor kitchen including storage and pullout drawer refrigerators, ideal for entertaining. The oversized garage offers excellent storage and the home’s elevation offers added peace of mind. Southbay is one of Sarasota County’s desirable waterfront communities with an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball, kayak storage and a seven-acre deep-water marina accommodating boats up to 55 feet. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events. Near SR 681, with easy access to downtown Sarasota, Venice, beautiful beaches and A-rated schools including Laurel Nokomis, Sarasota Middle, Venice High, Pine View and the European Academy. This is a rare opportunity to own a turnkey, top-tier home in an unmatched boating community.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
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