Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
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Osprey - 91 properties found
620 SARABAY RD, OSPREY, FL 34229
$349,90010 Days on yellowkey MLS ID: A4691273
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 948 Built: 1963 Tax: $3,935 (2025)Community: Bay Acres - ResubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,935
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: 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)
113 BURNEY RD, OSPREY, FL 34229
$999,50011 Days on yellowkey MLS ID: A4690672
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2502 Built: 2020 Tax: $10,455 (2025)Community: Bel-AirSpa: YesSingle Family
Taxes:$10,455
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **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)
313 LOOKOUT POINT DR, OSPREY, FL 34229
$5,999,99927 Days on yellowkey MLS ID: A4688995
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 5337 Built: 2016Monthly Fee: $219 Tax: $20,559 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$20,559
Remarks: Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
228 SAINT JAMES PARK, OSPREY, FL 34229
$1,645,00045 Days on yellowkey MLS ID: A4686681
0 Days Off yellowkey (back on 4/22/2026)
REDUCED by $50,000 (2.9%) on 04/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2425 Built: 1997Monthly Fee: $142 Tax: $10,787 (2025)Community: OaksSpa: YesSingle Family
Taxes:$10,787
Middle School: Sarasota Middle
Remarks: Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
642 TRENTON WAY, OSPREY, FL 34229
$2,150,00040 Days on yellowkey MLS ID: A4686927
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3939 Built: 2002Monthly Fee: $142 Tax: $16,068 (2025)Community: OaksSpa: YesSingle Family
Taxes:$16,068
Remarks: 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.
76 OSPREY POINT DR, OSPREY, FL 34229
$1,545,000161 Days on yellowkey MLS ID: A4672843
REDUCED by $45,000 (2.8%) on 04/20/2026
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4364 Built: 1986Monthly Fee: $475 Tax: $13,509 (2024)Community: OaksSingle Family
Taxes:$13,509
Tax Year: 2024
Remarks: OWNER SAYS SELL! No Reasonable offer refused on this home that is already the lowest price per Square foot on the market! COMPLETELY UPDATED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available upon request. Inside, the spacious layout includes a formal dining room, formal living room, and a cozy den with gas fireplace. Crown molding, tray ceilings, plantation shutters, and custom built-ins elevate the elegance throughout. Multiple sets of French doors open to the very private pool area, filling the home with natural light and enhancing indoor–outdoor living. The chef’s kitchen has been refreshed and features a six-burner Viking gas range with grill, Viking hood, Sub-Zero refrigerator/freezer, butler’s pantry, breakfast bar, and dining nook. The primary suite boasts two walk-in closets and a recent down-to-the-studs, resort-level bathroom remodel—one that would make even the Ritz envious. One guest suite occupies the west wing, while a spacious second-level suite adds comfort and flexibility. Significant structural upgrades include NEW low-E hurricane-impact windows and skylights, roll-down hurricane shutters (front and rear), and a whole-house generator for added peace of mind. Exterior enhancements include a NEW paver driveway and pool deck, extensive landscape lighting, and a very private pool area with new built-in grill and bar. Located in one of the Gulf Coast’s premier country club communities, The Oaks offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center. Club membership is required with homeownership.
362 MACEWEN DR, OSPREY, FL 34229
$2,249,000112 Days on yellowkey MLS ID: A4676567
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4117 Built: 1998Monthly Fee: $142 Tax: $10,742 (2025)Community: The OaksSingle Family
Taxes:$10,742
Remarks: Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
328 E BAY ST, OSPREY, FL 34229
$429,90015 Days on yellowkey MLS ID: O6400514
0 Days Off yellowkey (back on 4/21/2026)
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 884 Built: 1986 Tax: $1,236 (2025)Community: Sarabay AcresSingle Family
Taxes:$1,236
Elementary School: None
High School: None
Middle School: None
Remarks: 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)
665 CRANE PRAIRIE WAY, OSPREY, FL 34229
$719,000216 Days on yellowkey MLS ID: A4666718
1 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 2003Monthly Fee: $420 Tax: $4,513 (2025)Community: Willowbend Ph 2Spa: NoSingle Family
Taxes:$4,513
Remarks: Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant sunsets. Gourmet kitchen with natural gas range, stainless dishwasher and refrigerator (new 2026). The interior boasts custom features, including crown molding and elegant tray ceilings. This spacious four-bedroom, three-bath home includes a chef's kitchen outfitted with natural gas cooking, as well as a cozy eat-in area with an aquarium window that beautifully frames the pool and lake views. The owner's suite serves as a sanctuary, offering two walk-in closets and a luxurious bath complete with dual sinks, a walk-in shower, a soaker tub and a separate toilet for added privacy. Thoughtfully designed with a split floor plan, the home ensures guests enjoy ample separation from the owner's suite for optimal comfort. A full-size laundry room adds to the home’s convenience. This exceptional residence is a blank canvas for an extraordinary lifestyle, conveniently near downtown Venice and Sarasota, beautiful beaches, Pine View School and the Legacy Trail. With no CDD fees and in a preferred X flood zone, the low community fees cover ground maintenance, irrigation and access to a community pool and spa, gym, pickleball courts, as well as high-speed internet and DirecTV streaming. Embrace the lifestyle you’ve always dreamed of in this stunning Willowbend home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
447 N SHORE DR, OSPREY, FL 34229
$515,35060 Days on yellowkey MLS ID: A4684009
REDUCED by $19,550 (3.7%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Lauren Sisco (904-652-9387)
312 YACHT HARBOR DR, OSPREY, FL 34229
$1,995,000213 Days on yellowkey MLS ID: A4667293
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2572 Built: 1978Monthly Fee: $219 Tax: $14,066 (2024)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$14,066
Remarks: One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s seven-acre deep water boat basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet, with six feet of water at mean low tide and slips for 175 resident owned boats. Even more remarkable, Southbay’s HOA fees are only $218.87 per month and marina slips remain highly affordable, including both water and electric. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated waterfront home sits on one of only two waterfront streets in the entire community and features three bedrooms, four full baths and a versatile flex space office/fourth bedroom, with many rooms capturing beautiful water views. Inside, the residence welcomes you with an elegant tray ceiling entry, porcelain plank tile flooring and expansive open living spaces filled with natural light from an abundance of impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen with breakfast area flows seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and hosting guests. The outdoor living space is equally impressive, showcasing a newly built custom pool and spa framed by a panoramic clear span pool cage, an expansive stone tiled sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite enjoys double door access to the pool and spa and features a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large format tile and two custom walk in closets with built in organization systems. Two guest suites each include private en suites, with one offering marina views and the other opening directly to the pool terrace, both with custom closets. This move in ready residence also includes a three car garage, brick paver driveway and mature tropical landscaping. Just steps away, the newly renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and features a 99 person ballroom with catering kitchen and dance floor, a community gathering room with piano and entertainment area, fitness center, card room, library and meeting room. Residents also enjoy a geothermal heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, a waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf cart friendly and offers an active social calendar with weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities. Be sure to request the 50 page digital property catalog and watch the property film for a complete look at this exceptional residence.
Listing Agent: Thomas Netzel (941-539-0633)
1348 THORNAPPLE DR, OSPREY, FL 34229
$535,00025 Days on yellowkey MLS ID: A4687822
0 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2171 Built: 2003Monthly Fee: $397 Tax: $4,051 (2025)Community: Willowbend Ph 1Spa: NoSingle Family
Taxes:$4,051
Remarks: Under contract-accepting backup offers. Under contract- accepting backup offers. Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan and spacious living areas designed for comfortable everyday living and effortless indoor - outdoor flow. The private screened lanai overlooks the expansive lake and includes a pool, creating a peaceful setting to relax and enjoy Florida’s outdoor lifestyle. Many homes in the community are positioned along narrower sections of the lake, making this view especially appealing. The primary suite offers two walk-in closets, along with a bath featuring both a soaking tub and separate shower. The interior is original and presents an opportunity for a new owner to update and customize to their personal style. Recent improvements include a five year old air conditioning system and one year old water heater. Willowbend is a maintenance-free community with lawn care, landscaping, irrigation and internet included, conveniently located near the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, and Pine View School. Residents enjoy living in a beautifully established setting surrounded by lakes, preserves, and mature landscaping. Willowbend offers a community pool and spa, tennis and basketball courts and playground. This property offers strong value for its location, view, and private pool, and is ready for its next owner to make it their own.
Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)
Listing Agent: Margot Leonard (941-387-5050)
730 SARABAY RD, OSPREY, FL 34229
$4,995,000166 Days on yellowkey MLS ID: A4672618
Bed: 4 Bath: 5.5 Gar: 7 Liv Area Sq Ft: 6308 Built: 2011 Tax: $47,200 (2024)Community: Sarabay AcresSpa: YesSingle Family
Taxes:$47,200
Remarks: One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.
Listing is courtesy of: ROBERT SLACK LLC (352-229-1187)
Listing Agent: Debbie Baraona (941-350-8723)
172 SEA ANCHOR DR, OSPREY, FL 34229
$895,000173 Days on yellowkey MLS ID: A4671745
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2283 Built: 1977Monthly Fee: $204 Tax: $8,870 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$8,870
Remarks: Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)
Listing Agent: Sharon Lewis (941-966-5400)
745 FORDINGBRIDGE WAY, OSPREY, FL 34229
$640,00056 Days on yellowkey MLS ID: N6143319
REDUCED by $10,000 (1.5%) on 04/17/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1893 Built: 2002Monthly Fee: $120 Tax: $4,308 (2025)Community: Rivendell WoodlandsSpa: NoSingle Family
Taxes:$4,308
Remarks: Welcome to this beautiful home in the sought-after Rivendell community. The curb appeal is evident as you drive up to this home, from the landscape and the paver driveway to the beautiful front door. As you step inside the wide foyer, your view extends out through the sliders leading out to the pool and lanai. This well-maintained updated residence combines a bright, inviting interior designed for everyday living and entertaining. Neutral colored tiles extend throughout the kitchen, breakfast nook, dining and living areas. The kitchen is to the left of the dining and living area and offers generous counter space for all your preparation and cooking needs. The primary bedroom suite is spacious with sliders to the lanai and a large walk-in closet with a deluxe custom organizer. The ensuite bathroom has both a tub and a walk-in shower with a long vanity with two sinks and a makeup area in the middle. The remaining bedrooms and bathroom are on the other side of the house offering privacy for daily life or entertaining. Enjoy outdoor living at its finest with your private, heated pool and a backyard that offers desirable privacy — perfect for relaxing or hosting guests year-round. Recent major upgrades provide peace of mind, including a new Novatik metal roof (2025) along with new fascia, soffits, and gutters. The home also features an updated HVAC system (2023) and impact windows and doors everywhere with a motorized Kevlar hurricane shutter for the lanai. Rivendell is a beautiful 400-acre community with parks, trails, and a community pool located in Osprey. It is in close proximity to Pine View School. It is between charming Venice and vibrant Sarasota, so you'll enjoy a rich array of shopping, dining, and cultural experiences. Within a few miles, you can be at the world-famous Siesta Key Beach to swim or relax on the beach. Or head south a few miles to the more secluded Nokomis Beach and North Jetty Beach. This location truly offers easy access to the best of coastal living. For outdoor enthusiasts, Legacy Trail Osprey Junction Trailhead is nearby as is Oscar Scherer State Park. Explore the natural beauty of the region at your own pace while biking or walking, taking in the lush scenery and tranquil surroundings. Don’t miss the opportunity to own this thoughtfully upgraded home in one of Osprey’s most popular communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-485-5421)
Listing Agent: Janet Oberholtzer (484-798-7824)
479 SOUTH CREEK DR, OSPREY, FL 34229
$2,495,000154 Days on yellowkey MLS ID: N6141722
0 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4261 Built: 1995Monthly Fee: $150 Tax: $11,095 (2024)Community: South CreekSpa: YesSingle Family
Taxes:$11,095
Remarks: Under contract-accepting backup offers. Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 7,000-pound boat lift and a DEDICATED KAYAK LAUNCH, creating seamless access to the Intracoastal lifestyle. Inside, five generously sized bedrooms each feature ensuite baths and large walk-in closets, with two bedrooms conveniently located on the first floor along with a dedicated office, den, or bonus room. The renovated kitchen is designed for both beauty and function with a Thermador cooktop, Jenn- Airconvection and built-in ovens, a large island, and a passthrough window for effortless outdoor entertaining. The dining area overlooks the pool and includes hurricane-impact sliding doors, a coffee or dry bar with mini-fridge, and additional custom cabinetry for storage. The living room is highlighted by soaring ceilings, transom windows, additional hurricane impact sliding glass doors, and charming shiplap ceiling details, creating a light-filled coastal ambiance. Upstairs, three additional bedrooms and a loft gathering area overlook the living space below, with the true primary suite on the second level along with two waterfront-view bedrooms, all featuring ensuite baths and generous closets, plus a second-floor laundry hookup for added convenience. A spacious three-car garage and elegant U-shaped driveway complete the home. This home has been replumbed and features new lift motors (2025). Located within a gated community offering a basketball court, day dock, playground, and low HOA fees, this property is just 5 miles to Nokomis Beach on Casey Key, 15 miles to downtown Sarasota, 6 miles to the Island of Venice, and 6 miles to Sarasota Memorial Hospital, with Oscar Scherer State Park right nearby for nature lovers and outdoor enthusiasts.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
1019 SCHERER WAY, OSPREY, FL 34229
$735,000121 Days on yellowkey MLS ID: N6142144
0 Days Off yellowkey (back on 1/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2498 Built: 2004Monthly Fee: $120 Tax: $6,107 (2025)Community: Rivendell The WoodlandsSpa: YesSingle Family
Taxes:$6,107
Remarks: Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window overlooking the lanai. Large living room with tray ceilings. Vaulted ceilings in the family room with a built-in as the focal point. Formal dining room with a palladium window allowing the sunlight in. Wow! describes the spacious screened lanai featuring a salt water heated in ground pool w/spa. Plenty of space for dining, entertaining and games. Backing to the preserve with additional fenced in yard area. Home is situated less than a mile from the Legacy Bike Trail, and nearby Oscar Scherer State Park, Nokomis beach, the Gulf historic downtown Venice, shopping, restaurants & schools. Freshly painted. Bright & Airy. One of the lowest HOA fees around. 3 car garage with EV charging station. Owned Tesla solar panels that keep the electric bills very low. The home checks all the boxes and a must see!
Listing is courtesy of: CENTURY 21 SCHMIDT REAL ESTATE (941-485-0021)
Listing Agent: Christine Appice (908-692-5062)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000212 Days on yellowkey MLS ID: A4667263
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4096 Built: 1969Monthly Fee: $33 Tax: $37,172 (2024)Community: Casey KeySpa: NoSingle Family
Taxes:$37,172
Remarks: Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Napolitano (941-993-0025)
120 CANDYCE DR, OSPREY, FL 34229
$650,000180 Days on yellowkey MLS ID: A4667108
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2103 Built: 1962 Tax: $10,123 (2024)Community: Sorrento ShoresSingle Family
Taxes:$10,123
Remarks: Under contract-accepting backup offers. This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation for your renovation. Whether you’re an investor looking for your next project or a buyer eager to build sweat equity in a prime waterfront community, 120 Candyce Drive delivers both value and potential in one of Sarasota County’s most sought-after coastal neighborhoods. Ideally located just minutes from Nokomis Beach, Casey Key, and popular waterfront dining, this home combines location and opportunity with no HOA restrictions. Turn this waterfront fixer-upper into your stunning Florida escape.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
1602 SOUTHBAY DR, OSPREY, FL 34229
$974,900230 Days on yellowkey MLS ID: A4665288
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2980 Built: 1986Monthly Fee: $204 Tax: $9,955 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$9,955
Remarks: Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical landscaping and stately curb appeal immediately set the tone. Step inside to a generously sized home designed for both relaxation and entertaining. Open living areas, large windows, and high ceilings create an airy, welcoming atmosphere, while the refreshed interiors offer a clean, move-in-ready feel. The updated kitchen serves as the heart of the home, providing both style and functionality for everyday living and hosting guests. The interior flows seamlessly into the private outdoor oasis, where the recently updated pool and jacuzzi invite you to enjoy endless days under the Florida sun. Whether hosting friends for a casual barbecue, unwinding with a sunset soak, or enjoying your morning coffee poolside, this space perfectly embodies Florida’s indoor-outdoor lifestyle. Positioned on a corner lot, the home offers exceptional privacy, light, and space—ideal for family gatherings or a peaceful retreat. Spacious bedrooms provide comfort for both owners and guests. A washer and dryer convey with the sale, along with a brand-new pool table, adding both convenience and entertainment value. Life in Southbay Yacht & Racquet Club is more than just owning a home—it’s embracing a lifestyle. Enjoy access to the deep-water marina with Gulf access, tennis and pickleball courts, a vibrant social calendar, fitness amenities, and waterfront strolls. Just minutes away are the pristine beaches of Siesta Key and Nokomis, along with world-class dining and boutique shopping. Here, every day truly feels like vacation.
Listing Agent: Thomas Kiessling (941-920-1678)
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