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.
For sale
$1,649,000
75 Osprey Point Dr, Osprey, FL 34229
4beds
4,001sqft
Single Family Residence
Built in 1983
0.76 Acres Lot
$-- Zestimate®
$412/sqft
$950/mo HOA
What's special
Gas fireplaceExceptional privacyMajestic oak treesSparkling poolBeautifully landscaped groundsImpressive great roomSoaring vaulted ceilings
- 28 days |
- 1,868 |
- 114 |
Zillow last checked:
Listing updated:
Listed by:
Steve Abbe 941-400-3969,
COLDWELL BANKER REALTY 941-383-6411,
Shannon Rocha 941-961-8739,
COLDWELL BANKER REALTY
Source: Stellar MLS,MLS#: A4695145
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 4
Rooms
- Room types: Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Living Room, Great Room
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 224 Square Feet
- Dimensions: 14x16
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 208 Square Feet
- Dimensions: 13x16
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 121 Square Feet
- Dimensions: 11x11
Dining room
- Level: First
- Area: 1160 Square Feet
- Dimensions: 29x40
Foyer
- Level: First
- Area: 216 Square Feet
- Dimensions: 12x18
Great room
- Level: First
- Area: 990 Square Feet
- Dimensions: 22x45
Kitchen
- Level: First
- Area: 135 Square Feet
- Dimensions: 9x15
Laundry
- Level: First
- Area: 104 Square Feet
- Dimensions: 13x8
Other
- Level: First
- Area: 240 Square Feet
- Dimensions: 12x20
Heating
- Heat Pump, Zoned
Cooling
- Central Air, Zoned
Appliances
- Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Laundry: Inside, Laundry Room
Features
- Ceiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Carpet, Tile
- Windows: Blinds, Window Treatments
- Has fireplace: Yes
- Fireplace features: Gas
Interior area
- Total structure area: 5,028
- Total interior livable area: 4,001 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Circular Driveway, Garage Faces Side
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Patio
- Exterior features: Irrigation System
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Trees/Woods, Water, Pond
- Has water view: Yes
- Water view: Water,Pond
- Waterfront features: Waterfront
Lot
- Size: 0.76 Acres
- Dimensions: 260 x 130
- Features: In County, Near Golf Course
- Residential vegetation: Bamboo, Mature Landscaping, Oak Trees, Trees/Landscaped, Wooded
Details
- Additional structures: Guest House
- Additional parcels included: 0
- Parcel number: 0142050014
- Zoning: RE1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Concrete,Tile
Condition
- New construction: No
- Year built: 1983
Details
- Builder name: Bo MacEwen
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Connected
Community & HOA
Community
- Features: Dock, Waterfront, Deed Restrictions, Golf, Irrigation-Reclaimed Water
- Security: Security System, Security System Owned, Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: OAKS
HOA
- Has HOA: Yes
- Amenities included: Gated, Security, Vehicle Restrictions
- Services included: 24-Hour Guard, Common Area Taxes, Reserve Fund, Fidelity Bond, Manager, Private Road, Security
- HOA fee: $950 monthly
- HOA name: Access Management/Hope Root
- HOA phone: 813-607-2220
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $412/sqft
- Tax assessed value: $1,193,700
- Annual tax amount: $14,635
- Date on market: 6/11/2026
- Cumulative days on market: 210 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Paved
Foreclosure details
Estimated market value
Not available
Estimated sales range
Not available
$5,937/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/11/2026 | Listed for sale | $1,649,000-2.7%$412/sqft |
Source:  Stellar MLS #A4695145 Report a problem | ||
| 5/20/2026 | Listing removed | $1,695,000$424/sqft |
Source: Stellar MLS #A4672439 Report a problem | ||
| 4/14/2026 | Price change | $1,695,000-4.5%$424/sqft |
Source: Stellar MLS #A4672439 Report a problem | ||
| 1/8/2026 | Price change | $1,775,000-10.1%$444/sqft |
Source: Stellar MLS #A4672439 Report a problem | ||
| 11/19/2025 | Listed for sale | $1,975,000+19.8%$494/sqft |
Source: Stellar MLS #A4672439 Report a problem | ||
| 6/1/2025 | Listing removed | $1,649,000$412/sqft |
Source: Stellar MLS #A4628121 Report a problem | ||
| 3/24/2025 | Price change | $1,649,000-8.1%$412/sqft |
Source: Stellar MLS #A4628121 Report a problem | ||
| 2/4/2025 | Price change | $1,795,000-4.2%$449/sqft |
Source: Stellar MLS #A4628121 Report a problem | ||
| 12/29/2024 | Listed for sale | $1,874,000+10.6%$468/sqft |
Source: Stellar MLS #A4628121 Report a problem | ||
| 10/30/2024 | Listing removed | $1,695,000$424/sqft |
Source: Stellar MLS #A4611113 Report a problem | ||
| 9/19/2024 | Listed for sale | $1,695,000$424/sqft |
Source: Stellar MLS #A4611113 Report a problem | ||
| 8/29/2024 | Pending sale | $1,695,000$424/sqft |
Source: Stellar MLS #A4611113 Report a problem | ||
| 7/18/2024 | Price change | $1,695,000-5.6%$424/sqft |
Source: Stellar MLS #A4611113 Report a problem | ||
| 5/22/2024 | Listed for sale | $1,795,000$449/sqft |
Source: Stellar MLS #A4611113 Report a problem | ||
| 1/15/2024 | Listing removed | -- |
Source: Stellar MLS #A4577020 Report a problem | ||
| 12/15/2023 | Price change | $1,795,000+0.4%$449/sqft |
Source: Stellar MLS #A4577020 Report a problem | ||
| 11/17/2023 | Pending sale | $1,787,000$447/sqft |
Source: Stellar MLS #A4577020 Report a problem | ||
| 9/16/2023 | Price change | $1,787,000-5.2%$447/sqft |
Source: Stellar MLS #A4577020 Report a problem | ||
| 8/31/2023 | Price change | $1,885,000-5%$471/sqft |
Source: Stellar MLS #A4577020 Report a problem | ||
| 7/19/2023 | Listed for sale | $1,985,000-9.7%$496/sqft |
Source: Stellar MLS #A4577020 Report a problem | ||
| 6/18/2023 | Listing removed | -- |
Source: Stellar MLS #A4561774 Report a problem | ||
| 5/24/2023 | Listed for sale | $2,199,000$550/sqft |
Source: Stellar MLS #A4561774 Report a problem | ||
| 5/11/2023 | Listing removed | -- |
Source: Stellar MLS #A4561774 Report a problem | ||
| 4/11/2023 | Price change | $2,199,000-6.4%$550/sqft |
Source: Stellar MLS #A4561774 Report a problem | ||
| 2/27/2023 | Listed for sale | $2,349,000+261.4%$587/sqft |
Source: Stellar MLS #A4561774 Report a problem | ||
| 2/25/2021 | Sold | $650,000$162/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,636 +2.9% | $1,172,127 +10% |
| 2024 | $14,229 +18.2% | $1,065,570 +10% |
| 2023 | $12,038 +7.3% | $968,700 +8% |
| 2022 | $11,222 +81.6% | $896,700 +82.5% |
| 2021 | $6,178 -0.4% | $491,384 +1.4% |
| 2020 | $6,202 -17.8% | $484,600 -18.9% |
| 2019 | $7,547 | $597,847 +1.9% |
| 2018 | $7,547 +2% | $586,700 +1.1% |
| 2017 | $7,398 -19.1% | $580,100 +2.9% |
| 2016 | $9,141 | $564,000 -16% |
| 2015 | $9,141 +4.6% | $671,800 +33.2% |
| 2014 | $8,737 +18.1% | $504,500 |
| 2013 | $7,398 -4.3% | $504,500 -5.6% |
| 2012 | $7,728 +5.4% | $534,500 +4% |
| 2011 | $7,330 -12.1% | $513,800 -10.3% |
| 2010 | $8,337 -12.2% | $573,000 -12.4% |
| 2009 | $9,494 | $653,800 -8% |
| 2008 | $9,494 -3% | $710,300 -2.5% |
| 2007 | $9,783 +1.1% | $728,800 +17.2% |
| 2004 | $9,674 -8% | $622,100 -5.4% |
| 2003 | $10,517 -1.1% | $657,800 -1.7% |
| 2002 | $10,634 +17.6% | $669,200 +12.3% |
| 2001 | $9,044 +18.3% | $595,800 +20.4% |
| 2000 | $7,643 | $495,000 |
Find assessor info on the county website
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Climate risks
Neighborhood: 34229
Nearby schools
GreatSchools rating
- 8/10Laurel Nokomis SchoolGrades: PK-8Distance: 6.5 mi
- 7/10Venice Senior High SchoolGrades: 9-12Distance: 8.6 mi
Schools provided by the listing agent
- Elementary: Laurel Nokomis Elementary
- Middle: Sarasota Middle
- High: Venice Senior High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Sarasota County
- Osprey
- 34229
- 75 Osprey Point Dr
Nearby cities
Nearby zip codes
Other Osprey Topics
