Description
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.
Details
| MLS # | A4695145 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| HOA Dues | $5,700 |
| Sub-Type | For-sale |
| Status | Active |
| Year | 1983 |
| Days On Site | 94 |
| Listing Provided By | COLDWELL BANKER REALTY | Steve Abbe |
Features
| Bed(s) | 4 |
|---|---|
| Bath(s) | 4 Total |
| SQ Feet | 4,001 |
| Garage | 2 |
| Pool | Yes |
| Story(s) | 1 |
| Zoning | RE1 |
| Acreage | 0.76 |
| Property View | Trees, Woods, Water |
Taxes
| Property | 14635 |
|---|
Area Information
| State | FL |
|---|---|
| County | Sarasota |
| City | OSPREY |
| Zip Code | 34229 |
| Area | 34229 Osprey |
| Subarea | The 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: $1,595,000 low | high Med: $719,000 sqft: 4,001 low | high Med: 2,328 $ / sqft: $399 low | high Med: $309 On site: 94 low | high Med: 44 | |
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 13, 2026 at 10:52:44 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 | The 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: $1,595,000 low | high Med: $719,000 sqft: 4,001 low | high Med: 2,328 $ / sqft: $399 low | high Med: $309 On site: 94 low | high Med: 44 | |
 | $2,399,00049 Osprey Point DrOsprey, FL 34229 |