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$1,649,000
$412/sqft
HOA: $5,700/seTaxes: $14,636/yr0d on market

Oaks

75 OSPREY POINT DR, OSPREY, FL, 34229

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4 Beds|4 Baths|4,001 Sq Ft|Built 1983|2 Car Garage
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🔥 Just listed — this home matches what most buyers are looking for in this area.

Acreage
Lot Size
0.76 acres
Lot Sqft
32,983 sqft
Lot Features
In County, Near Golf Course, Private
Golf Course
Feature
Near Golf Course
Community
Yes
C2C

Coast 2 Coast Home Realty

Licensed Florida Realtors

4.9· 214 reviews

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Buyer Insights

Here's what we know about this listing.

Why this home stands out

  • Updated today

Buyer Insights are informational only — always verify with your agent.

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.

City
OSPREY
Subdivision
OAKS
County
Sarasota
Zip Code
34229
Community
The Oaks

School Report Card

Source: FL Dept. of Education

ABCDF
Elementary
Middle
High
Type
Single Family Residence
Living Area
4,001 sqft
Construction
Block, Stucco
Roof
Concrete, Tile
Flooring
Carpet, Tile
Pool
Yes
HOA
$5,700 / Semi-Annually
  • Ceiling Fans(s)
  • Crown Molding
  • High Ceilings
  • Primary Bedroom Main Floor
  • Solid Wood Cabinets
  • Vaulted Ceiling(s)
  • Walk-in Closet(s)
  • Window Treatments
  • Dishwasher
  • Disposal
  • Dryer
  • Electric Water Heater
  • Exhaust Fan
  • Microwave
  • Range
  • Range Hood
  • Refrigerator
  • Washer
  • Wine Refrigerator
  • Inside
  • Laundry Room
  • Patio
  • In County
  • Near Golf Course
  • Private
  • Bb/hs Internet Available
  • Cable Connected
  • Deed Restrictions
  • Golf
  • Irrigation-reclaimed Water
  • Dock
  • Waterfront
  • Gated
  • Security
  • Vehicle Restrictions
  • Guard - 24 Hour
  • Common Area Taxes
  • Escrow Reserves Fund
  • Fidelity Bond
  • Management
  • Private Road
  • Security
  • Guest House
Bedrooms
4
Bathrooms
4
Year Built
1983
Construction
Block, Stucco
Flooring
Carpet, Tile
Roof
Concrete, Tile
Garage Spaces
2
Cooling
Central Air, Zoned
Heating
Heat Pump, Zoned
Waterfront
No
Pet Restrictions
Dogs Ok, Yes
Lot Size
0.76 acres
Senior Community
No
Building Elevator
Pet Size
Extra Large (101+ Lbs.)
# of Pets
3
Max Pet Weight
101 lbs
Tax Year
2025
Annual Tax Amount
$14,636

Association Fees

  • HOA Fee

    Access Management/Hope Root

    $5,700/ Semi-Annually

Down Payment20% — $329,800
Interest Rate6.50%
Loan Term
Est. Mortgage
$8,338
HOA Fee
$950
Est. Property Tax
$1,220
Est. Insurance
$550
Total Est. Monthly Cost$11,058

* Estimates are for illustration purposes only and do not constitute an offer of financial advice. Actual rates, payments, insurance, and taxes will vary based on credit, location, and other factors. Contact a licensed mortgage professional for a personalized quote. Homeowners insurance estimate based on Florida averages.

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