101 Osprey Point Dr,OSPREY, FL 34229
OSPREY, FL 34229
Description
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota's prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community's most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef's kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler's pantry and sunlit breakfast nook overlooking the gardens further enhance the home's livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota's premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast's most established luxury communities.
Details
| MLS # | A4694716 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| HOA Dues | $5,700 |
| Sub-Type | For-sale |
| Status | Active |
| Year | 1985 |
| Days On Site | 111 |
| Listing Provided By | DOUGLAS ELLIMAN | Joel Schemmel |
Features
| Bed(s) | 4 |
|---|---|
| Bath(s) | 6 Total |
| SQ Feet | 5,087 |
| Garage | 3 |
| Pool | Yes |
| Story(s) | 1 |
| Zoning | RSF1 |
| Acreage | 0.93 |
| Water Front | Yes |
| Property View | Water |
Taxes
| Property | 12940 |
|---|
Area Information
| State | FL |
|---|---|
| County | Sarasota |
| City | OSPREY |
| Zip Code | 34229 |
| Area | 34229 Osprey |
| Subarea | Oaks |
| Community Name | OAKS |
| School District | Venice Senior High |
| Elementary School | Laurel Nokomis Elementary |
| High School | Venice Senior High |
| Listing VS Median (in OAKS) | |
Price: $4,790,000 low | high Med: $719,000 sqft: 5,087 low | high Med: 2,328 $ / sqft: $942 low | high Med: $309 On site: 111 low | high Med: 45 | |
Market Activity 34229
Request a showing
Request a showing
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 14, 2026 at 7:36:34 AM 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.
Contact
Learn More About This Property
| State | FL |
|---|---|
| County | Sarasota |
| City | OSPREY |
| Zip Code | 34229 |
| Area | 34229 Osprey |
| Subarea | Oaks |
| Community Name | OAKS |
| School District | Venice Senior High |
| Elementary School | Laurel Nokomis Elementary |
| High School | Venice Senior High |
| Listing VS Median (in OAKS) | |
Price: $4,790,000 low | high Med: $719,000 sqft: 5,087 low | high Med: 2,328 $ / sqft: $942 low | high Med: $309 On site: 111 low | high Med: 45 | |
 | $1,595,00075 Osprey Point DrOsprey, FL 34229 |
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.
