313 Lookout Point Dr,OSPREY, FL 34229
OSPREY, FL 34229
Description
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.
Details
| MLS # | A4688995 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| HOA Dues | $656 |
| Sub-Type | For-sale |
| Status | Active |
| Year | 2016 |
| Days On Site | 167 |
| Listing Provided By | MICHAEL SAUNDERS & COMPANY | Natalie Gutwein |
Features
| Bed(s) | 4 |
|---|---|
| Bath(s) | 5 Total |
| SQ Feet | 5,337 |
| Garage | 5 |
| Car Port | Yes |
| Pool | Yes |
| Story(s) | 2 |
| Zoning | RSF2 |
| Acreage | 0.41 |
| Water Front | Yes |
| Property View | Water |
Taxes
| Property | 20559 |
|---|
Area Information
| State | FL |
|---|---|
| County | Sarasota |
| City | OSPREY |
| Zip Code | 34229 |
| Area | 34229 Osprey |
| Subarea | Southbay Yacht & Racquet Club |
| Community Name | SOUTHBAY YACHT & RACQUET CLUB |
| School District | Venice Senior High |
| Elementary School | Laurel Nokomis Elementary |
| High School | Venice Senior High |
| Listing VS Median (in SOUTHBAY YACHT & RACQUET CLUB) | |
Price: $5,999,999 low | high Med: $1,399,000 sqft: 5,337 low | high Med: 3,255 $ / sqft: $1,124 low | high Med: $430 On site: 167 low | high Med: 10 | |
Market Activity 34229
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Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 21, 2026 at 12:45:47 PM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
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Learn More About This Property
| State | FL |
|---|---|
| County | Sarasota |
| City | OSPREY |
| Zip Code | 34229 |
| Area | 34229 Osprey |
| Subarea | Southbay Yacht & Racquet Club |
| Community Name | SOUTHBAY YACHT & RACQUET CLUB |
| School District | Venice Senior High |
| Elementary School | Laurel Nokomis Elementary |
| High School | Venice Senior High |
| Listing VS Median (in SOUTHBAY YACHT & RACQUET CLUB) | |
Price: $5,999,999 low | high Med: $1,399,000 sqft: 5,337 low | high Med: 3,255 $ / sqft: $1,124 low | high Med: $430 On site: 167 low | high Med: 10 | |
 | $2,199,999154 Lookout Point DrOsprey, FL 34229 |
 | $6,400,0003240 Casey Key RdNokomis, FL 34275 |
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
