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A4691789 - 97 SUGAR MILL DR, OSPREY, FL 34229 3 Days on yellowkey
$1,950,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)Listing Agent: Maria Domenech (978-204-3219)
A4689967 - 4429 CONCHFISH LN, OSPREY, FL 34229 3 Days on yellowkey
$535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Beautiful residence located in The Palms of Casey Key community, offering a thoughtfully designed layout ideal for everyday living and entertaining. Offers 1% lender credit at closing. The home spans approximately 2,000+ square feet and features updated flooring throughout all bedrooms and closets, along with tile in the main living areas for durability and easy upkeep. A spacious great room anchors the interior, creating a natural gathering space for family and guests, while the private primary suite is set apart at the rear of the home and includes dual sinks, a soaking tub, walk-in shower, and generous closet space. Outdoor living is highlighted by a covered lanai overlooking a private backyard, ideal for relaxing or entertaining. Additional features include a two-car garage and a well-maintained neighborhood setting with HOA oversight and community amenities nearby. Positioned just steps from Pine View School, it also provides convenient access to US-41 and I-75, placing top-rated schools, beaches, marinas, dining, and shopping just minutes away.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)Listing Agent: Jennifer Kenna (941-253-3003)
A4692034 - 254 BURNEY RD, OSPREY, FL 34229 3 Days on yellowkey
$4,500 | Single Family Home | 5 beds | 4.5 baths | 2 gar
Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, ideal for large families or those working from home. Enjoy an open-concept layout with a modern kitchen, high-end finishes, and abundant natural light throughout. The flexible floor plan provides ample space for living, working, and entertaining. Conveniently located just minutes from Pine View School, shopping, dining, and the beautiful Gulf beaches including Siesta Key Beach. Easy access to U.S. Route 41 and I-75 makes commuting simple. Move-in ready. Don’t miss this exceptional rental opportunity!
Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)Listing Agent: Phoebe Zhang (727-458-5188)
A4692030 - 246 BURNEY RD, OSPREY, FL 34229 3 Days on yellowkey
A4691576 - 408 YACHT HARBOR DR, OSPREY, FL 34229 6 Days on yellowkey
$1,375,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Under contract-accepting backup offers. Renovated throughout, this stunning four-bedroom, four-bath residence is in one of the West Coast of Florida's premier marina communities, Southbay Yacht and Racquet Club. This sought-after waterfront community features a community-owned marina with 172 boat slips accommodating vessels up to 55 feet, all within a protected deep-water basin. Enjoy low quarterly HOA fees, $656, for a resort-style atmosphere. This home features a beautifully updated chef's kitchen with a gas cooktop, double ovens and a large island with ample seating. A spacious dining room and wet bar provide an ideal setting for gatherings, while the split bedroom floor plan offers privacy for family and guests. Recent upgrades include a newer roof, hurricane-rated windows, appliances and updated plumbing and electrical. Osprey is between Sarasota and Venice, just 20 minutes to the famous Siesta Key Beach. A quarter mile away, the Legacy Trail offers miles of scenic biking and walking paths, along with easy access to Oscar Scherer State Park. The area has an abundance of waterfront dining options and shopping just a walk or golf cart ride away. Osprey is home to Pine View School for the gifted, consistently ranked the number one school in Florida and among the top in the nation.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)Listing Agent: Thomas Netzel (941-539-0633)
N6144070 - 14021 BELLAGIO WAY #404, OSPREY, FL 34229 7 Days on yellowkey
$1,289,000 | Condo | 3 beds | 3.0 baths | 2 gar
This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Boating enthusiasts will appreciate the included 50-foot boat slip accommodating vessels 44 feet, ideal for exploring the Intracoastal Waterway and beyond. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)Listing Agent: Megan E. George, Pa (941-726-1998)
A4690387 - 562 OAK BAY DR, OSPREY, FL 34229 7 Days on yellowkey
$560,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
One or more photo(s) has been virtually staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees. The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026). Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard. The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower. The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows. The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience. A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring. At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense). Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018). This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch. Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more. This is a home you need to experience in person. Schedule your private showing today!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)Listing Agent: Julianna Burns (941-800-7653)
A4691525 - 354 PINE RUN DR, OSPREY, FL 34229 7 Days on yellowkey
$1,695 | Condo | 2 beds | 2.0 baths
This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash, and a peninsula with additional counter space. An eat-in area sits adjacent to a sliding glass door that opens to the private courtyard. The living room has wood-grain flooring, vaulted ceilings, and sliding glass doors opening to a balcony with treetop views. The dining area is open to the living room and shares the same vaulted ceiling. A hallway lined with sliding glass doors overlooks the private courtyard, filling the interior with natural light. The master bedroom has vaulted ceilings, sliding glass doors to a balcony, and a walk-in closet with built-in shelving. The master bathroom has a single vanity with a granite countertop and a tub/shower combination. The spare bedroom also features vaulted ceilings, sliding glass doors to a balcony, and custom built-in cabinetry with dresser drawers and upper storage. The spare bathroom has a pedestal sink and a walk-in shower. A laundry closet contains a stacked washer and dryer. The condo also features a private enclosed courtyard with a wood deck, accessible from both the kitchen and the hallway via sliding glass doors. Pine Run is set on over 20 acres of native Florida landscape in Osprey. Community amenities include two heated swimming pools, four tennis courts, pickleball courts, a fitness center, a clubhouse, and shell-covered walking trails that wind through the grounds. A community grilling area and fire pit overlooking a lake provide additional gathering spaces. Pine Run is located on Blackburn Point Road just west of U.S. 41, situated between Sarasota and Venice. The Legacy Bike Trail and Oscar Scherer State Park are nearby, and Blackburn Point Park with a kayak launch is close by. Casey Key and Nokomis Beach are a short drive away, and restaurants such as the Casey Key Fish House are nearby. Downtown Sarasota and downtown Venice are both easily accessible for shopping, dining, and cultural attractions. Please allow up to 30 days after lease signing for community approval before move-in. We score every application. If an application doesn't score high enough, the resident may be required to place the equivalent of two months' rent in a security deposit. Please be aware that leasing this property includes a non-optional Home Assistant Services Package that will cost an additional $39 per month. These services and their cost are separate from Tenant's monthly rent payment and all other payments described in the Lease or any separate Lease addendums. The Home Assistant Services offered are described in the Resident Welcome Packet which can be viewed on Sarasota Management's website.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING (941-377-8400)Listing Agent: Todd Roughton (941-377-8400)
A4691273 - 620 SARABAY RD, OSPREY, FL 34229 10 Days on yellowkey
$349,900 | Single Family Home | 2 beds | 1.5 baths | 1 gar
Experience relaxed coastal living in this well-located home just west of the Trail in Osprey. Situated minutes from the Intracoastal Waterway and a short drive to Nokomis Beach, this property offers a prime location with easy access to Sarasota, Venice, shopping, dining, and waterfront parks. This home features a comfortable layout with spacious living areas and abundant natural light throughout. The kitchen offers ample cabinet and counter space, ideal for everyday living and entertaining. Bedrooms are well-sized, providing flexibility for guests, a home office, or additional living space. Enjoy a private outdoor setting with room to relax and unwind, along with convenient parking and a quiet residential atmosphere. This is a great opportunity to enjoy the sought-after Osprey/Nokomis coastal corridor. Features: Prime West of the Trail location Close to beaches and Intracoastal access Spacious living areas Private outdoor space Convenient access to Sarasota & Venice
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)Listing Agent: Mike Sorensen (941-380-2900)
A4691036 - 1361 NEW FOREST LN, OSPREY, FL 34229 10 Days on yellowkey
$550,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)Listing Agent: Linh Pham (941-900-6789)
A4690672 - 113 BURNEY RD, OSPREY, FL 34229 11 Days on yellowkey
$999,500 | Single Family Home | 3 beds | 2.5 baths | 3 gar
**DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near the end of a quiet cul-de-sac, the property offers a private backyard and NO HOA fees/restrictions. Bring Your Toys! Oversized circular driveway provides ample parking for a BOAT, RV, and additional vehicles. This Impressive Residence with 2502sf of heating living space, features 3 Bedrooms plus Study/Den, 2 Full and 1 Half Baths, and a 3-car tandem garage. The Light and Bright, Open Floor Plan is enhanced by tile flooring throughout, tray ceilings, Hurricane Impact Windows and Sliding Doors, plantation shutters, etc. The expansive kitchen is designed for both everyday living and entertaining, featuring a large island, hardwood cabinetry, and premium stainless-steel appliances including Thermador, Bosch, etc. The owner’s suite offers a large, divided walk-in closet and a luxurious en-suite bath with dual vanities and a custom-tiled shower. A spacious, screened lanai provides a beautiful view of the expansive, landscaped and private backyard while showcasing a Heated/Cooled, Saltwater Pool/Spa, along with a large, covered seating area and an Outdoor Kitchen BBQ, Quartzite countertop/sink —perfect for enjoying Florida’s outdoor lifestyle. The Ideally located with easy access to US-41 (Tamiami Trail), this home is just a short drive to world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)Listing Agent: Mark Lyda (941-586-2670)
A4690942 - 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229 12 Days on yellowkey
$735,000 | Condo | 2 beds | 2.0 baths | 2 gar
Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)Listing Agent: Suki Scollo (941-587-2289)
A4690812 - 409 NORTH POINT RD #401, OSPREY, FL 34229 13 Days on yellowkey
$625,000 | Condo | 3 beds | 3.0 baths
Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)Listing Agent: Steve Abbe (941-400-3969)
A4690371 - 51 MAC EWEN DR #14, OSPREY, FL 34229 14 Days on yellowkey
$285,000 | Condo | 1 beds | 1.0 baths
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.
A4689838 - 51 MACEWEN DR #5, OSPREY, FL 34229 14 Days on yellowkey
$300,000 | Condo | 1 beds | 1.0 baths
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.
Listing is courtesy of: 342 REAL ESTATE (941-685-0509)Listing Agent: Sabine Spycher (941-685-0509)
O6400514 - 328 E BAY ST, OSPREY, FL 34229 15 Days on yellowkey
$429,900 | Single Family Home | 2 beds | 1.0 baths | 1 gar
Welcome to this beautifully updated home on a half acre lot. Presenting a modern comfort in a county-like setting. Only 10 minutes from Siesta Key Beach, 8 minutes from Nokomis Beach, within a mile from a highly sought-after Pine View Elementary School, and close to shopping and dining! Inside you will find a fully remodeled interior featuring a custom kitchen with shaker cabinets, subway tile backsplash, and quartz countertops. You will also find new Samsung Bespoke appliances including a refrigerator, range, microwave, dishwasher, washer and dryer. High-end laminate flooring throughout, an updated bathroom with new tile, modern shower with a glass enclosure, and a custom vanity with a touch to illuminate mirror. Outside enjoy a 12x24 screened in lanai, a large yard for entertaining, gardening, or just room to relax. This property has generous parking with room for a RV, boat, and multiple additional vehicles, along with a 16x10 powered shed for storage, hobbies, or workshop.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)Listing Agent: Steven Koleno (804-656-5007)
O6399774 - 759 FORDINGBRIDGE WAY, OSPREY, FL 34229 18 Days on yellowkey
$727,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
A4685559 - 61 BAYHEAD LN, OSPREY, FL 34229 19 Days on yellowkey
$1,185,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters thoughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB EQUITY MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. Buyer Bonus: Seller is offering $40,000 towards Buyer's Equity Club Membership!!! ***Most Furnishings are Available Under a Separate Contract.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)Listing Agent: Anne Thomas, Pa (941-993-7700)
A4690018 - 402 MACEWEN DR, OSPREY, FL 34229 20 Days on yellowkey
$1,750,000 | Single Family Home | 3 beds | 3.5 baths | 3 gar
Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday comfort. From the moment you enter, a sense of understated elegance unfolds—gracious formal living spaces anchored by a statement fireplace, soaring tray ceilings, intricate crown molding, and an abundance of natural light that enhances every architectural detail. The primary suite serves as a true retreat, offering impressive proportions, a substantial walk-in closet, and a spa-inspired bath designed for relaxation. Additional living spaces flow effortlessly, including a well-equipped laundry room with custom built-in workspace, ideal for modern living. Every inch of the home reflects careful attention to detail, from the finishes to the functional layout. Outdoors, the residence truly shines. The screened lanai becomes a private sanctuary, complete with a sparkling pool and spa, perfectly positioned to capture sweeping views of the 4th hole. Whether entertaining guests or enjoying quiet evenings, this space delivers an elevated indoor-outdoor lifestyle synonymous with luxury coastal living. Enhancing both comfort and peace of mind, the home is equipped with a whole-house generator, and Security Camera's outside and the oversized three-car side entrance garage and circular paver driveway provide both convenience and impressive curb appeal. Quick notes to take away: Roof - 2023 / A/C (both units) - 2024 Ownership within The Oaks grants access to an unparalleled private club experience. Residents enjoy two championship 18-hole golf courses, impeccably maintained HAR-TRU tennis courts, newly introduced pickleball facilities, and a state-of-the-art Wellness and Fitness Center exceeding 7,500 square feet. Complemented by an exceptional culinary program and a vibrant calendar of curated social events, The Oaks offers a lifestyle defined by elegance, activity, and connection. Club membership is required, within this distinguished Sarasota community.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)Listing Agent: Steven Kepecz, Pa (941-376-6411)
A4690063 - 32 SIESTA CIR W, OSPREY, FL 34229 20 Days on yellowkey
$69,000 | Mobile Home | 1 beds | 1.0 baths | 2 car
Charming and affordable 1-bedroom, 1-bath mobile home in desirable Osprey, FL! Situated on a spacious corner lot, this cozy residence offers great potential with a price that reflects the opportunity to update and make it your own. The open living room flows seamlessly into the kitchen, with space for a small dining table—perfect for casual living. The primary bedroom features a convenient built-in desk or makeup area, adding both function and charm. Durable metal siding and roofing provide peace of mind, while the extra-wide carport offers ample covered parking, complemented by additional public parking along the side lot. Enjoy Florida living outdoors with tropical palm trees welcoming you home, a large screened lanai for relaxing or entertaining, and a handy storage shed. Washer and dryer are included for added convenience. A great opportunity to own in a prime location with plenty of potential—don’t miss it! 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.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)Listing Agent: Karen Geiger (941-928-8889)
A4689837 - 238 PALM AIR DR, OSPREY, FL 34229 20 Days on yellowkey
$172,900 Reduced | Manufactured Home | 2 beds | 2.0 baths | 1 car
Under contract-accepting backup offers. Fall in love with this beautifully maintained and upgraded 2 Bedroom, 2 Bathroom home located in the highly desirable The Arbors Mobile Home Park, extremely LOW HOA FEES covers CABLE, INTERNET, WATER, SEWER, TRASH and GROUND MAINTENANCE! You will have peace of mind with IMPACT-RESISTANT WINDOWS AND SLIDING GLASS DOORS, NEW Water Heater, plus an updated electrical panel. The kitchen has been tastefully renovated with new cabinetry, countertops, farmhouse sink, pull down faucet, stunning glass subway tiled backsplash, and premium stainless steel appliances including a French door refrigerator with two drawers and a super quiet dishwasher. The living room has barn style doors that opens to a large sun-kissed enclosed tiled florida room that features a vaulted ceiling, lots of windows and an additional portable AC unit for your comfort for enjoying your morning coffee and evening cocktails. The Primary Suite features an ensuite bath with a newer high vanity, decorative lighting, new toilet, and two spacious walk-in closets. The second bedroom is a Flexible Guest Space that includes a stylish, space-saving Murphy bed and its own walk-in closet. There is plenty of extra storage in the oversized attached shed 12'x15' that includes front-loading washer/dryer and a sink plus there is also a separate 8’x10’ workshop with hurricane straps and tie downs. Entertaining friends is easy in this open style concept home with plenty of outdoor space that includes a large covered carport, a spacious screened in lanai, and a private back patio with custom pavers. Attention to detail can be seen everywhere including the outdoor low voltage lighting around the entire exterior of the home and up-lighting shining on the palms creating a wonderful ambiance. The Arbors is in a premier 55+ Co-op community, amenities include Heated pool, clubhouse, shuffleboard, billiards, fitness equipment, dog park, and a dedicated RV/Boat parking in the community. Prime Location with minutes from Nokomis Beach, Siesta Key, and Casey Key. Easy access to shopping, dining, hospitals, airports and nature parks like Oscar Scherer.
Listing is courtesy of: RE/MAX PALM (941-929-9090)Listing Agent: Susan Retzke (941-544-5558)
A4689938 - 531 LATITUDE LN, OSPREY, FL 34229 20 Days on yellowkey
$2,950 | Single Family Home | 2 beds | 2.0 baths | 2 gar
Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink. The Willowbend community features a community pool and spa, gym and pickleball. The excellent location in Osprey gives you easy access to Sarasota and Venice, including Siesta Key Beach, Nokomis Beach, shopping and dining. Also nearby are top-rated Pine View School, the Intracoastal Waterway, beaches and Legacy Trail. High-speed internet, direct TV streaming, and lawn maintenance are all included.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)Listing Agent: Alex Lane (941-960-3080)
A4689731 - 14041 BELLAGIO WAY #214, OSPREY, FL 34229 20 Days on yellowkey
$700,000 | Condo | 3 beds | 2.0 baths | 2 gar
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)
A4689582 - 4173 FRONTIER LN #4173, OSPREY, FL 34229 24 Days on yellowkey
$289,000 | Condo | 2 beds | 2.0 baths | 1 gar
Under contract-accepting backup offers. INCREDIBLE CHARM!....INCREDIBLE LOCATION!.....You will be ENAMORED by this Highly Sought After (2) Bedroom (2) Bath Heron Floor Plan with PRIVATE GARAGE in the PET FRIENDLY Gated Community, Bay Street Village. This Meticulously Maintained One Owner corner unit residence features BRIGHT SPACIOUS INTERIORS; Hurricane Impact Windows and a Generous Screened Lanai---perfect for enjoying Morning Coffee while listening to your Favorite Podcast or just relaxing with Evening Cocktails.....Meal Prep is Easy with OVER-SIZED KITCHEN ISLAND; Stainless Steel Appliances and Pantry for Extra Storage....Bay Street is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!.....Ideal as Year-Round, Vacation or Investment Property.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)Listing Agent: Mike Martino (773-619-8593)
A4689541 - 4271 EXPEDITION WAY #103, OSPREY, FL 34229 24 Days on yellowkey
$290,000 | Condo | 2 beds | 2.0 baths | 1 gar
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)
A4687822 - 1348 THORNAPPLE DR, OSPREY, FL 34229 25 Days on yellowkey
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)
A4688266 - 1527 BUOY LN, OSPREY, FL 34229 27 Days on yellowkey
$1,199,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)Listing Agent: Matthew Lewis (651-746-4100)
A4689096 - 409 N POINT RD #1001, OSPREY, FL 34229 27 Days on yellowkey
$2,750,000 | Condo | 3 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. **STUNNINGLY RENOVATED, MOVE-IN READY 10th FLOOR PENTHOUSE CORNER RESIDENCE WITH GULF AND BAY VIEWS.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional, 3029sf condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. 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**
A4688995 - 313 LOOKOUT POINT DR, OSPREY, FL 34229 27 Days on yellowkey
$5,999,999 | Single Family Home | 4 beds | 4.5 baths | 5 gar
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)
C7524397 - 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229 27 Days on yellowkey
$599,000 | Condo | 3 beds | 2.5 baths | 2 gar
Welcome home! This GULF ACCESS, WATERFRONT condo in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A CANAL—delivering unmatched PRIVACY, VAULTED ceilings, and MILLION DOLLAR WATER & SUNSET VIEWS that feel like a daily postcard. Lush tropical landscaping welcomes you to a private side entrance, while the building’s exclusive setting—just four units total—places you in one of the most desirable locations within the community. Perfectly situated at the edge of the MARINA, you are just STEPS from your BOAT, making it effortless to enjoy GULF ACCESS and endless days exploring nearby WATERWAYS, waterfront DINING, and hidden gems like Snake Island. Inside, this residence blends comfort and coastal elegance with a thoughtfully designed SPLIT FLOOR PLAN for ultimate privacy. The home features warm COASTAL decor, NEUTRAL PAINT, NEW KITCHEN APPLIANCES, GRANITE COUNTERTOPS, SOLID WOOD CABINETRY, custom light fixtures, and window treatments throughout. The open-concept living space flows seamlessly to a LARGE SCREENED LANAI overlooking the water, community park, and glowing SUNSET skies. FURNISHINGS ARE OPTIONAL. Set within a GATED, FINANCIALLY SOUND community spanning approximately 11 acres, residents enjoy an amenity-rich, resort-style lifestyle including a HEATED POOL, CLUBHOUSE, FITNESS ROOM, TENNIS & PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, BBQ GAZEBO, and scenic walking paths surrounded by lush Florida foliage. The vibrant social calendar offers something for everyone—water aerobics, monthly happy hours, bingo/game nights, pickleball club, book club, and more. Ideally located near US-41, this home offers convenient access to Nokomis Beach, Oscar Scherer State Park, the Legacy Trail, Downtown Venice, Downtown Sarasota, I-75, and Sarasota Memorial Hospital Venice Campus—placing the very best of Florida living right at your fingertips. Whether you're boating to the Gulf, enjoying sunset views from your lanai, or embracing the active waterfront lifestyle, this is truly the Florida Dream come to life. Schedule your private showing today! PLEASE CLICK ON THE VIDEO OF THE UNIT.
Listing is courtesy of: DOWNING FRYE REALTY, INC. (239-261-2244)Listing Agent: Mackenzie Davis-Mahan (941-993-3272)
A4687965 - 4226 FRONTIER LN #103, OSPREY, FL 34229 27 Days on yellowkey
$319,000 | Condo | 2 beds | 2.0 baths | 1 gar
Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)Listing Agent: Kate Kwiecinski (412-477-9720)
A4688310 - 1116 BEACHCOMBER CT #3, OSPREY, FL 34229 31 Days on yellowkey
$545,000 | Condo | 3 beds | 2.5 baths | 1 gar
LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with tile flooring and flow seamlessly into a well-appointed kitchen, complete with Corian countertops, a breakfast bar, center island, closet pantry, and stainless-steel appliances, perfect for both everyday living and entertaining. The dining area features pocketing sliders that extend the living space to the enclosed lanai, already plumbed for a full outdoor kitchen, offering the ideal indoor-outdoor Florida lifestyle. The primary suite is conveniently located on the ground floor and offers a private retreat with an ensuite bathroom featuring dual vanities, a garden tub, and a walk-in shower. Upstairs, two additional bedrooms and a full bath provide privacy and comfort for guests or family. Step outside to the patio, an ideal setting to relax and enjoy a quiet afternoon or evening cocktail in the Florida sunshine. Additional features include an oversized one-car garage with under-stair storage, a new A/C system (2025), and a new roof (2025), providing peace of mind for years to come. Residents of Blackburn Marina Village enjoy access to a heated community pool, a fully equipped outdoor kitchen, and a vibrant social calendar for those who wish to participate. Ideally located with easy access to Gulf beaches, Blackburn Point Marina, dining, and shopping, this exceptional property truly offers the best of Florida living!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)Listing Agent: Christine Green (941-914-2463)
A4688762 - 570 BLACKBURN POINT RD #40, OSPREY, FL 34229 31 Days on yellowkey
$98,000 | Dock-Rackominium
Welcome to this quality high end marine facility. Take confidence knowing that your boat is stored in this completely enclosed hurricane rated boat building. Your privately owned boat rack offers unlimited in and out splashes, outside work racks, ethanol free fuel, independent detailing contractors, a full-service shop including deli, drinks, ice, bait and other miscellaneous services. The docks have fillet tables, pump out station, fresh water hoses and electrical. This spacious slip holds a boat 32.5' in length, 10' wide and 9 feet in height. Open seven days a week, your boat can be splashed within an hour's notice. Conveniently located just minutes from midnight pass and centrally located between Venice and Sarasota. Master Association fees are included in the hoa fees.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)Listing Agent: David Babel (941-232-1614)
A4687852 - 166 EDGEWOOD DR, OSPREY, FL 34229 33 Days on yellowkey
$167,000 | Manufactured Home | 2 beds | 2.0 baths | 1 car
Under contract-accepting backup offers. Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath manufactured home offers comfort, updates, and plenty of space to relax and entertain. Step inside to a spacious living room filled with natural light, perfect for gathering with family and friends. The updated kitchen features warm wood cabinetry and a brand-new refrigerator (2025), making meal prep both stylish and functional. A separate dining area with a built-in buffet adds character and convenient storage. The primary suite provides a peaceful retreat with an ensuite bath, while the guest bedroom includes a desirable walk-in closet for added storage. Enjoy year-round sunshine in the light and bright Florida room, or unwind on the large screened lanai—ideal for enjoying Florida’s beautiful weather. Additional highlights include a storage shed with laundry, plywood underlayment replaced in 2014, and durable luxury vinyl flooring throughout. Major updates offer peace of mind with a new roof (2025), AC system (2023) and carport (2025). Located in the pet section of the community, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, 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. Come see why so many love calling The Arbors home!
A4688006 - 353 S SHORE DR, OSPREY, FL 34229 33 Days on yellowkey
$1,150,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 gar
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)
A4688291 - 449 WEBBS COVE, OSPREY, FL 34229 33 Days on yellowkey
$2,650,000 | Single Family Home | 4 beds | 3.5 baths | 3 gar
A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views. Offering 5,287 square feet of living space, the home features four bedrooms, an office, a study, and 3½ baths, with a floor plan designed for both refined entertaining and comfortable living. Travertine marble and rich hardwood floors extend beneath coffered and tray ceilings, while aquarium windows and impact glass fill the interiors with natural light and frame serene lake views. A gas fireplace anchors the living room, and surround sound enhances the main living areas, all flowing seamlessly to the screened lanai. The chef’s kitchen is appointed with Wolf and Sub-Zero appliances, an oversized island with bar seating, and a walk-through pantry. A casual dining area adjoins the kitchen, while a separate formal dining room accommodates more formal gatherings. A wet bar with a large-capacity wine refrigerator and custom cabinetry adds a sophisticated entertaining element. The primary suite offers a private sitting area and a luxurious bath with separate vanities, individual dressing areas, private water closets, and two walk-in closets with custom built-ins. Three additional bedrooms are thoughtfully positioned for family or guests, along with a spacious office, separate study, and a five-seat home theater. Outdoors, the expansive screened lanai is designed for year-round living, featuring a pool, spa, fountain, covered seating, and a full outdoor kitchen overlooking the lake and lush tropical landscaping. An elegant circular paver drive and a three-car garage with epoxy floors and extensive storage enhance both form and function. Additional highlights include a whole-home vacuum system, solid wood doors, impact windows, a cedar closet, and abundant storage throughout. Located in Flood Zone X for added peace of mind. The Oaks Country Club offers 2 championship 18 hole golf courses, Tennis, pickleball, croquet, bocce, and an abundance of social activities to stay engaged in all the club has to offer. Ideally located near downtown Sarasota, Siesta Key Beach, and renowned cultural destinations, Oaks Bayside offers a rare blend of privacy and convenience. Membership to The Oaks Club is required. A wonderful opportunity to live in one of the finest country clubs in Florida.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)Listing Agent: Rosalie Phillips (941-544-4430)
A4687664 - 135 WOODLAND PL, OSPREY, FL 34229 35 Days on yellowkey
$269,000 | Condo | 2 beds | 2.0 baths | 1 car
Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden view with four patios that includes a rear lanai enclosed with sliding vinyl windows. A unique inner atrium with aquarium style glass windows adds architectural interest and abundant natural light while maintaining privacy. The unit features easy to maintain custom tile floors on the diagonal throughout with wood floor inspired ceramic tiles in the bedrooms. Since 2023, unit updates include all new kitchen appliances, new faucets, new PEX water lines, a new water heater as well as new paint inside and out. The unit also includes a deeded carport parking space and two storage closets. Onsite resort style amenities include two heated pools (one overlooking a lagoon), two cedar saunas, a fitness room, Florida style clubhouse, walking trails, BBQ gas grill, outdoor gas fireplace, kayak storage, pickleball and tennis courts. Within a mile is the Pine View School (the only standalone public gifted school in the state), Oscar Scherer State Park, 2 kayak launches, a public boat ramp, Casey Key Fish House, Walmart and a Post Office. Easily walk to Publix, Ace Hardware, CVS, shops and restaurants or bike to the Legacy Trail and Nokomis Beach. Exceptional privacy, easy access, and a premier location make this residence an outstanding opportunity. Priced to sell!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)Listing Agent: Kim Azar-Calka (239-216-6205)
A4687368 - 434 MACEWEN DR, OSPREY, FL 34229 35 Days on yellowkey
$1,465,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.
A4687161 - 1016 SCHERER WAY, OSPREY, FL 34229 36 Days on yellowkey
$950,000 | Single Family Home | 4 beds | 3.0 baths | 3 gar
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 is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)Listing Agent: Rachel Tritschler (941-993-5892)
A4687195 - 448 E MACEWEN DR, OSPREY, FL 34229 37 Days on yellowkey
$2,100,000 | Single Family Home | 4 beds | 3.5 baths
**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**
N6143587 - 437 S SHORE DR, OSPREY, FL 34229 40 Days on yellowkey
$525,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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)
A4686927 - 642 TRENTON WAY, OSPREY, FL 34229 40 Days on yellowkey
$2,150,000 | Single Family Home | 4 beds | 4.5 baths | 4 gar
Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wall ovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options.
A4687365 - 234 PALM AIR DR, OSPREY, FL 34229 41 Days on yellowkey
$120,000 | Manufactured Home | 2 beds | 2.0 baths | 1 car
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.**
A4683382 - 230 OSPREY POINT DR, OSPREY, FL 34229 42 Days on yellowkey
$2,495,000 | Single Family Home | 3 beds | 3.5 baths
Designed by Las Casitas Architects, this Spanish-style residence, featuring 3 bedrooms, 3.5 baths, a den/study with built-in Murphy bed and a 3-car garage, sits on an oversized .59-acre preserve lot with circular drive and courtyard entry. The light-filled, open floorplan features wood and marble flooring, crown molding, tray ceilings, and custom built-ins throughout. The chef’s kitchen is a standout with solid wood cabinetry, granite countertops, a large island with prep sink, counter seating, and premium appliances including Thermador and Bosch. The expansive master suite includes multiple walk-in closets and a luxurious bath with dual vanities and a large custom-tiled shower. Guest bedrooms are generously sized and well-appointed. Enjoy exceptional Florida outdoor living on the spacious screened lanai with heated saltwater pool, outdoor kitchen, and ample covered seating—all overlooking the tranquil North Creek Coastal Preserve. This home is equipped with Control4 automation, Lutron lighting, whole-house water filtration and softener, NEW generator with 500-gallon propane tank, hurricane-impact windows and doors, and two tankless water heaters. A rare combination of quality construction, modern systems, privacy, and natural beauty—this home is truly move-in ready.
A4686928 - 393 N POINT RD #401, OSPREY, FL 34229 42 Days on yellowkey
$785,000 Reduced | Condo | 3 beds | 3.0 baths | 2 car
Offered Turn-Ker Furnished...This beautifully updated 3 bedroom, 3 bath residence with a den offers exceptional space, style, and privacy in Meridian at The Oaks Preserve. The home features a redesigned kitchen with new appliances and granite countertops, a newer A/C system, and rich wood flooring throughout. As an end unit, it enjoys abundant natural light, and the expansive screened balcony—with electric hurricane shutters—creates a private outdoor retreat with real water views, a rarity from a unit at this level! A private elevator opens directly into the residence, providing an impressive and convenient entry experience. OFFERED TURNKEY FURNISHED, additional highlights include two assigned garage parking spaces and close proximity to the Meridian residents-only pool, spa, and fitness room, making everyday living effortless. Set within The Oaks Preserve, this community delivers the best of care-free country club living. Mandatory membership in The Oaks Club unlocks an unmatched array of amenities, including two championship golf courses, 12 HAR-TRU tennis courts, pickleball courts, an award-winning tennis program, a state-of-the-art fitness center, three dining venues, and a vibrant year-round social calendar.
A4686681 - 228 SAINT JAMES PARK, OSPREY, FL 34229 45 Days on yellowkey
$1,645,000 Reduced | Single Family Home | 3 beds | 2.5 baths | 2 gar
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.
A4686669 - 3929 WAYPOINT AVE, OSPREY, FL 34229 47 Days on yellowkey
$4,500 | Single Family Home | 3 beds | 3.5 baths | 2 gar
ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor space is remarkable from the heated pool and spa with southern exposure plus a bonus outdoor kitchen with built in Gas fireplace. Tandem 3 car garage will allow for ample storage for bikes and kayaks. Bayside is a fabulous place to be with opportunity to kayak and paddle board everyday. Bayside also has sunset lovers in mind with a private dock and waterfront sitting area perfect for evening romance. Minutes away from shopping, Venice Beach, Siesta Key Beach, Nokomis Beach and Casey Key Beach. Lots of time to go biking with the new Legacy trail and Oscar Scherer Park. Unfurnished*No smoking* 1st, last & Security for move in!
A4686127 - 51 MACEWEN DR #12, OSPREY, FL 34229 52 Days on yellowkey
$2,250 Reduced | Condo | 1 beds | 1.0 baths
For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A combined bedroom/living room, new kitchenette with quartz countertop, dining nook, office/dressing room, well designed bathroom with walk-in shower, office/dressing room, and stacked washer/dryer. Lobby elevator provides access to the second floor. Windsor Lodge Residents have their own private swimming pool and club house. Centrally located and 15 minutes to Siesta Key Beach. Note: Residents of Windsor Lodge do not have access to The Oak Club amenities. Available now for an seven plus month lease at $2250 month.
Listing is courtesy of: WAGNER REALTY (941-955-1500)Listing Agent: Patrice Ivan (941-993-0823)
A4684805 - 140 SUGAR MILL DR, OSPREY, FL 34229 55 Days on yellowkey
$1,399,000 Reduced | Single Family Home | 4 beds | 4.0 baths | 2 gar
SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining - making any occasion a treat! The private primary suite is "magazine worthy" - a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan - offering privacy with three additional suites - perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage - and you'll be the envy of the neighborhood with the "thought of everything" laundry room and spacious garage. Step outside to exceptional outdoor living - designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you'll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful - it's been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks - Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay - perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you're just minutes from Sarasota's outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida's ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)Listing Agent: Monica Verinder (941-704-4040)
N6143319 - 745 FORDINGBRIDGE WAY, OSPREY, FL 34229 56 Days on yellowkey
$640,000 Reduced | Single Family Home | 4 beds | 2.0 baths | 2 gar
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)