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Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1989
  • 0.4 Acre Lot
  • $5,700/yr HOA
  • Waterfront
  • 2 Car Garage
  • 362 days on Market

  • Bedrooms
    4
  • Bathrooms
    3 full · 1 half
  • Year Built
    1989
  • Stories
    1.0
  • Architectural Style
    Contemporary, Custom
  • Construction Materials
    Stucco, Block, Concrete
  • Foundation
    Slab
  • Garage Spaces
    2.0
  • Parking Features
    Attached, Workshop in Garage
  • Living Area
    3953.0
  • Interior Features
    Eat-in Kitchen, Walk-In Closet(s), Vaulted Ceiling(s), High Ceilings, Stone Counters, Built-in Features
  • Appliances
    Dishwasher, Refrigerator, Range, Range Hood
  • Flooring
    Concrete
  • Exterior Features
    Storage, Outdoor Shower
  • Patio And Porch
    Covered, Enclosed, Screened
  • Pool Features
    In Ground, Private, Salt Water
  • Security Features
    Gated Community
  • Cooling
    Central Air, Zoned
  • Heating
    Zoned, Central

  • Acres
    0.4
  • Lot Features
    Waterfront, Landscaped
  • Water Front Features
    Lake Front, Lake Privileges
  • Water Front
    Yes
  • View
    Lake, Water
  • Utilities
    Cable Available, Cable Connected, Electricity Connected, Water Connected
  • Water
    Public

  • Area
    34229 - Osprey
  • County
    Sarasota
  • City
    Osprey
  • Neighborhood
    OAKS
  • Zip Code
    34229
  • High School
    Venice Senior High
  • Middle School
    Sarasota Middle
  • Elementary School
    Laurel Nokomis Elementary

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Frequently Asked Questions

How do I schedule a tour of 49 Osprey Point Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 49 Osprey Point Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 49 Osprey Point Dr?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $2,399,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Osprey, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 49 Osprey Point Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 49 Osprey Point Dr at around $14,836. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 49 Osprey Point Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Sarasota County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 49 Osprey Point Dr?

In most cases, yes. Whether 49 Osprey Point Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Osprey's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 49 Osprey Point Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Osprey and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $2,399,000 with 3,953 sqft of space—that comes out to approximately $607 per square foot.

How long has this property been on the market?

49 Osprey Point Dr was listed on November 13, 2025, which means it's been on the market for 362 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1989, making it approximately 37 years old.

What is the lot size of this property?

49 Osprey Point Dr sits on a 0.4-acre lot, which is 17,424 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Laurel Nokomis Elementary
  • Middle: Sarasota Middle
  • High: Venice Senior High

Want to see how these schools compare? Check out our Sarasota County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 49 Osprey Point Dr?

The most recent public record shows annual property taxes for 49 Osprey Point Dr were approximately $14,206. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $5,700 paid annually.

This covers access to community features including: Clubhouse, Fitness Center, Maintenance, Tennis Court(s), Golf Course.

Is 49 Osprey Point Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: November 10, 2026 at 01:47AM | Source: Stellar MLS | MLS#: A4671762