Seller's Agent in 2025
Thomas Cail
RE/MAX
(941) 780-2245
3 in this area
52 Total Sales
3336 Old Oak Dr Sarasota, FL 34239
Southside NeighborhoodEstimated Value: $8,843,000 - $10,007,000
3
Beds
5
Baths
5,932
Sq Ft
$1,576/Sq Ft
Est. Value
Highlights
- 138 Feet of Bay Harbor Waterfront
- White Water Ocean Views
- Heated In Ground Pool
- Southside Elementary School Rated A
- Oak Trees
- Custom Home
About This Home
As of June 2025Nestled within the vibrant city of Sarasota, Florida, this exquisite estate offers an unparalleled blend of luxury, privacy, and natural beauty. Situated on a sprawling 2-acre parcel of prime bayfront land, this custom-built residence boasts panoramic views of the shimmering waters, ensuring breathtaking sunsets year-round. As you enter through the gated entrance, you are greeted by meticulously manicured grounds adorned with majestic oaks and lush, mature landscaping, creating a serene and enchanting atmosphere. The estate exudes elegance and sophistication at every turn, with attention to detail evident in every aspect of its design. The residence spans just under 6,000 square feet of thoughtfully curated living space, featuring soaring ceilings, multiple fireplaces, and an abundance of natural light. The chef's kitchen is a culinary masterpiece, equipped with top-of-the-line appliances, custom cabinetry, and ample space for entertaining. Indulge in the ultimate relaxation in the expansive primary suite, complete with a luxurious spa-like bathroom and sweeping views of the bay. Additional amenities include a home gym, perfect for maintaining an active lifestyle, attached 4 car garage and a detached carriage garage for a minimum of 6 more vehicles, providing ample space for your prized automobile collection. Whether you're hosting gatherings or enjoying quiet moments of reflection, the estate offers an array of outdoor living spaces, including a spacious patio overlooking the bay, meticulously landscaped gardens, and a heated estate-style pool. Dive into the crystal-clear waters or bask in the warm Florida sun as you take in the stunning surroundings. Conveniently located close to Southside Village, downtown Sarasota, and the world-renowned Siesta Key Beach, this estate offers the epitome of waterfront living with easy access to the area's finest dining, shopping, and entertainment destinations. Centrally located yet secluded, this is truly a rare opportunity to own a slice of paradise in Sarasota, Florida. No flooding during recent storms, high and dry!
Last Agent to Sell the Property
RE/MAX ALLIANCE GROUP Brokerage Phone: 941-954-5454 License #0586337 Listed on: 04/25/2024
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $61,824
Year Built
- Built in 2014
Lot Details
- 1.98 Acre Lot
- 138 Feet of Bay Harbor Waterfront
- East Facing Home
- Masonry wall
- Mature Landscaping
- Private Lot
- Well Sprinkler System
- Oak Trees
- Wooded Lot
- Property is zoned RSFE
Parking
- 10 Car Attached Garage
- Workshop in Garage
- Garage Door Opener
- Guest Parking
Property Views
- White Water Ocean
- Intracoastal
Home Design
- Custom Home
- Slab Foundation
- Tile Roof
- Concrete Roof
- Block Exterior
- Stucco
Interior Spaces
- 5,932 Sq Ft Home
- 1-Story Property
- Wet Bar
- Built-In Features
- Built-In Desk
- Shelving
- Bar Fridge
- Crown Molding
- Coffered Ceiling
- High Ceiling
- Electric Fireplace
- Gas Fireplace
- Window Treatments
- French Doors
- Sliding Doors
- Great Room
- Living Room with Fireplace
- Combination Dining and Living Room
- Home Office
- Library
- Bonus Room
- Storage Room
- Inside Utility
- Home Gym
- Storm Windows
Kitchen
- Eat-In Kitchen
- Breakfast Bar
- Walk-In Pantry
- Built-In Convection Oven
- Cooktop with Range Hood
- Microwave
- Ice Maker
- Dishwasher
- Wine Refrigerator
- Granite Countertops
- Solid Wood Cabinet
- Disposal
Flooring
- Wood
- Brick
- Ceramic Tile
Bedrooms and Bathrooms
- 3 Bedrooms
- Split Bedroom Floorplan
- En-Suite Bathroom
- Walk-In Closet
- Rain Shower Head
Laundry
- Laundry Room
- Dryer
- Washer
Pool
- Heated In Ground Pool
- Gunite Pool
- Saltwater Pool
Outdoor Features
- Access to Bay or Harbor
- Screened Patio
- Outdoor Fireplace
- Outdoor Kitchen
- Outdoor Storage
- Outdoor Grill
- Rain Gutters
- Rear Porch
Location
- Flood Zone Lot
Utilities
- Forced Air Zoned Heating and Cooling System
- Natural Gas Connected
- Water Filtration System
- Well
- Cable TV Available
Community Details
- No Home Owners Association
- Shoreland Woods Community
- Shoreland Woods Sub Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 4
- Assessor Parcel Number 2039060001
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Apr 25, 2024
Closed on
Jun 9, 2025
Sold by
Bought by
Seller's Agent
Thomas Cail
RE/MAX ALLIANCE GROUP
Buyer's Agent
Ryan Ackerman
COLDWELL BANKER REALTY
List Price
$9,900,000
Sold Price
$9,500,000
Premium/Discount to List
-$400,000
-4.04%
Views
282
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$289,737
Avg. Annual Appreciation
-1.49%
Purchase Details
Listed on
Jul 13, 2012
Closed on
Apr 30, 2013
Sold by
Bought by
Seller's Agent
Michelle Crabtree
PREMIER SOTHEBY'S INTERNATIONAL REALTY
Buyer's Agent
Jason Grande
RE/MAX ALLIANCE GROUP
List Price
$2,995,000
Sold Price
$2,300,000
Premium/Discount to List
-$695,000
-23.21%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
12.42%
Purchase Details
Closed on
Jan 15, 2010
Sold by
Bought by
Purchase Details
Closed on
Apr 29, 1997
Sold by
Bought by
Purchase Details
Closed on
Feb 3, 1997
Sold by
Bought by
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Home Values in the Area
Average Home Value in this Area
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $9,500,000 | None Listed On Document | ||
| $2,300,000 | Attorney | ||
| -- | Attorney | ||
| -- | Attorney | ||
| -- | Attorney | ||
| $8,000,000 | -- | ||
| -- | -- |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/09/2025 06/09/25 | Sold | $9,500,000 | -4.0% | $1,601 / Sq Ft | |
| 05/04/2025 05/04/25 | Pending | -- | -- | -- | |
| 05/03/2025 05/03/25 | For Sale | $9,900,000 | 0.0% | $1,669 / Sq Ft | |
| 03/25/2025 03/25/25 | Pending | -- | -- | -- | |
| 03/08/2025 03/08/25 | Price Changed | $9,900,000 | -23.3% | $1,669 / Sq Ft | |
| 01/08/2025 01/08/25 | Price Changed | $12,900,000 | -28.3% | $2,175 / Sq Ft | |
| 04/25/2024 04/25/24 | For Sale | $18,000,000 | +682.6% | $3,034 / Sq Ft | |
| 04/30/2013 04/30/13 | Sold | $2,300,000 | -8.0% | $390 / Sq Ft | View Prior Sale |
| 03/29/2013 03/29/13 | Pending | -- | -- | -- | |
| 03/01/2013 03/01/13 | Price Changed | $2,499,900 | -9.1% | $424 / Sq Ft | |
| 12/13/2012 12/13/12 | Price Changed | $2,749,000 | -8.2% | $466 / Sq Ft | |
| 07/13/2012 07/13/12 | For Sale | $2,995,000 | -- | $508 / Sq Ft |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $62,202 | $7,421,400 | $4,613,000 | $2,808,400 |
| 2024 | $61,824 | $4,298,373 | -- | -- |
| 2023 | $61,824 | $4,173,178 | $0 | $0 |
| 2022 | $54,347 | $3,639,299 | $0 | $0 |
| 2021 | $54,804 | $3,533,300 | $2,102,400 | $1,430,900 |
| 2020 | $56,492 | $3,547,138 | $0 | $0 |
| 2019 | $55,047 | $3,467,388 | $0 | $0 |
| 2018 | $54,188 | $3,402,736 | $0 | $0 |
| 2017 | $53,589 | $3,332,748 | $0 | $0 |
| 2016 | $53,621 | $3,264,200 | $2,108,200 | $1,156,000 |
| 2015 | $54,552 | $3,359,500 | $2,291,000 | $1,068,500 |
| 2014 | $25,347 | $1,863,700 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Thomas Cail
-
Jason Grande
Seller Co-Listing Agent in 2025
Jason Grande
RE/MAX
(941) 954-5454
3 in this area
43 Total Sales
-
Ryan Ackerman
Buyer's Agent in 2025
Ryan Ackerman
COLDWELL BANKER REALTY
(305) 205-7700
4 in this area
148 Total Sales
-
Michelle Crabtree
Seller's Agent in 2013
Michelle Crabtree
PREMIER SOTHEBY'S INTERNATIONAL REALTY
(941) 724-4663
31 Total Sales
-
Kim Ogilvie
Seller Co-Listing Agent in 2013
Kim Ogilvie
Michael Saunders
(941) 376-1717
7 in this area
117 Total Sales
Map
Source: Stellar MLS
MLS Number: A4608565
APN: 2039-06-0001
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Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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