New Listing
$4,590,000
 $24,640 est/mo Sourced by Back At You

275 Lookout Point Dr,OSPREY, FL 34229

OSPREY, FL 34229

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Description

Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle-a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay's boating community.

Details

MLS #A4707430
Listing TypeFor Sale
StyleHouse
HOA Dues$656
Sub-TypeFor-sale
StatusActive
Year2007
Days On Site5
Listing Provided ByMICHAEL SAUNDERS & COMPANY | Natalie Gutwein

Features

Bed(s)5
Bath(s) 5 Total
SQ Feet5,279
Garage3
PoolYes
Story(s)2
ZoningRSF2
Acreage0.38
Water FrontYes
Property ViewWater

Taxes

Property17826

Area Information

StateFL
CountySarasota
CityOSPREY
Zip Code34229
Area34229 Osprey
SubareaSouthbay Yacht & Racquet Club
Community NameSOUTHBAY YACHT & RACQUET CLUB
School DistrictVenice Senior High
Elementary SchoolLaurel Nokomis Elementary
High SchoolVenice Senior High
Listing VS Median (in SOUTHBAY YACHT & RACQUET CLUB)
Price:
$4,590,000
low | high
Med:
$1,690,000
100% of Average
sqft:
5,279
low | high
Med:
2,411
100% of Average
$ / sqft:
$869
low | high
Med:
$701
69.382658819553% of Average
On site:
5
low | high
Med:
104
4.807692307692% of Average
Sourced by Back At You

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 October 6, 2026 at 5:08:08 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

StateFL
CountySarasota
CityOSPREY
Zip Code34229
Area34229 Osprey
SubareaSouthbay Yacht & Racquet Club
Community NameSOUTHBAY YACHT & RACQUET CLUB
School DistrictVenice Senior High
Elementary SchoolLaurel Nokomis Elementary
High SchoolVenice Senior High
Listing VS Median (in SOUTHBAY YACHT & RACQUET CLUB)
Price:
$4,590,000
low | high
Med:
$1,690,000
100% of Average
sqft:
5,279
low | high
Med:
2,411
100% of Average
$ / sqft:
$869
low | high
Med:
$701
69.382658819553% of Average
On site:
5
low | high
Med:
104
4.807692307692% of Average
Sourced by Back At You
Listing Updated: October 2, 2026 at 9:32:36 AM PDT