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Overview

4 bd4 ba3,953 sqft2 car garageSingle Family
TypeSingle Family
HOA$5,700/yr
Built1989
Lot17,230 sqft
Living area3,953 sqft
Price / sqft$607
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesCeiling Fans(s)Central VaccumEat-in KitchenHigh CeilingsPrimary Bedroom Main FloorSplit BedroomStone Counters

49 Osprey Point Dr is a 1989-built home in Oaks, Osprey. Inside you'll find 4 bedrooms, 4 bathrooms, and 3,953 square feet of living space. Listed at $2,399,000 (about $607/sqft), 333 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $5,700 annually.

From the listing

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.

The essentials

Built
1989
Price / sqft
$607
On market
333 days
Annual tax
$14,206
HOA
$5,700/yr
Flood zone
X · Low risk
Lot
17,230 sqft
Type
Single Family Residence

At a glance

Single family
Built 1989
Waterfront
Lake Front
Private pool
Fiber Optic Lighting
2 car garage
Workshop in Garage
0.40 acres
Lot size

Payment

Est. monthly payment
$15,370/mo
Down payment (20%)
$479,800
Property taxes
$1,184/mo
HOA
$5,700/yr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1989
Lot
17,230 sqft
Cooling
Central Air, Zoned
Heating
Central, Zoned
Parking
Workshop in Garage
Pool
Fiber Optic Lighting, In Ground, Salt Water
Waterfront
Lake Front
Days on Market
333
Built-in Features
Ceiling Fans(s)
Central Vaccum
Eat-in Kitchen
High Ceilings
Primary Bedroom Main Floor
Split Bedroom
Stone Counters
Thermostat
Vaulted Ceiling(s)
Walk-in Closet(s)
Outdoor Shower
Sliding Doors
Storage
Clubhouse
Deed Restrictions
Fitness Center
Gated Community - Guard
Golf
Pool
Restaurant
Tennis Court(s)
Dishwasher
Range
Range Hood
Refrigerator
Elementary
Laurel Nokomis Elementary
Middle
Sarasota Middle
High
Venice Senior High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2024)
$14,206
Parcel #
0142060007

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Oaks
County
Sarasota
MLS Area
34229 - Osprey
Lot Size
17,230 sqft
LandscapedOversized Lot
HOA
$5,700/yr
The Oaks Club

Price history

Date
Event
Price
5/3/2026
Price change
Source: Stellar MLS #A4671762
$2,399,000-4.0%
$607/sqft
-
Price change
Source: Stellar MLS #A4671762
$2,500,000-3.7%
$632/sqft
11/11/2025
Listed for sale
Source: Stellar MLS #A4671762
$2,595,000
$656/sqft

Neighborhood

49 Osprey Point Dr
Osprey, FL, 34229 · 34229 - Osprey

Market insights

Offer Insights

Choose an offer strength

List price: $2,399,000
$2.28M – $2.40M
95.2% – 100% of listTops out right at the list price
80% of listList price
35 of the last 66 home closings in 34229 landed at this number or higher (53%). The median one sat 35 days before it went under contract, and this one is on day 333 after a $196,000 cut.

Sample: 66 closed home sales in 34229 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$15,370/mo
Principal & interest$12,512
Property taxes$1,184
Insurance$1,200
HOA$475
Down payment20% · $479,800
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$2,399,000

$607 per sq ft

Beds and baths

4 beds, 4 baths

Size

3,953 sq ft

Time on market

333 days

Year built

1989

Monthly payment

About $15,370/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $14,206 annual tax bill, insurance, and the $5,700/yr HOA fee.

HOA fee

$5,700/yr

Managed by The Oaks Club.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

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Brokered byMICHAEL SAUNDERS & COMPANYListing agent: Jonathan Abrams, PLLCListing data from Stellar MLS, MLS# A4671762.

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