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$1,950,000
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Property Description
A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks, setting an unforgettable first impression of timeless elegance and privacy. Wrapped in a freshly painted pecky cypress facade and crowned by a newer standing-seam metal roof, the residence honors classic Florida design while embracing today's luxury standards. Inside, a welcoming foyer unfolds into an airy, open-concept living space anchored by rich natural wood floors and impeccable finishes throughout. A dramatic dual-sided stone fireplace creates a striking focal point between the living and dining areas, while a sophisticated dry bar sets the stage for effortless entertaining. A private office-thoughtfully positioned away from the main living areas-offers flexibility as a refined workspace or guest retreat, complete with an adjacent half bath. At the heart of the home, the chef's kitchen is nothing short of spectacular, featuring premium stainless steel appliances, a natural gas range, custom cabinetry, designer backsplash, and an oversized marble island that commands attention. A built-in coffee bar adds a touch of indulgence, while French doors invite the outdoors in. Step into a resort-inspired sanctuary where a heated saltwater pool and spa shimmer beneath a newly installed panoramic screen enclosure. Entertain with ease in the fully equipped summer kitchen, complete with stainless gas grill, vent hood, and prep station, or gather around the gas fire pit for evenings under the palms. A newly updated outdoor shower with hot and cold water enhances the spa-like ambiance, while the expansive, lushly landscaped yard offers exceptional privacy and room to relax, play, or unwind. The primary suite is a true retreat, featuring three generous closets, a cozy fireplace, and French doors opening directly to the lanai for seamless indoor-outdoor living. The spa-inspired en-suite bath showcases luxurious finishes, custom vanities, and a walk-in shower designed for pure relaxation. Additional highlights include a spacious laundry room, oversized two-car garage, and curated architectural lighting that bathes the estate in a warm, elegant glow at dusk. Perfectly located just minutes from the Siesta Key North Bridge and the boutiques and dining of Southside Village, this property offers the rare balance of serene seclusion and coastal convenience. Situated outside of a flood zone-with flood insurance optional-this estate represents both luxury and peace of mind.
Full Property Details
Full Property Details for 3331 Old Oak Dr
General
- Price: $1,950,000
- Taxes: $18,715 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4675449
- Updated: 2/18/2026
- Added to Site: 101 day(s) ago
Rental Information
- Min. Lease: 2 Weeks
Interior
- Number of Rooms: 8
- Interior Features: Ceiling Fan(s), Dry Bar, Living Room/Dining Room Combo, Open Floorplan, Skylight(s), Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Electric, Gas, Living Room, Master Bedroom
- Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Salt Water
- Spa: Yes
- Spa Description: Heated
Exterior
- Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters
- Deck/Patio: Deck, Enclosed, Patio, Porch, Screened
- Porch/Patio/Deck: Deck, Enclosed, Patio, Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Boat, Driveway, Garage Door Opener, Guest, Oversized, Workshop in Garage
Location
- Area: 34239 - Sarasota/Pinecraft
- County: Sarasota
- Development Name: 34239 - Sarasota/Pinecraft
- Subdivision: SHORELAND WOODS SUB
- Driving Directions: spring creek to old oak. home is on the left.
- Direction Faces: West
Community
- Community Name: 34239 - Sarasota/Pinecraft
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric, Natural Gas, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Natural Gas Available, Public, Sprinkler Well
Structural Information
- Architectural Info: Florida
- Architectural Style: Florida
- Exterior Const.: Wood Frame
- Roof: Metal
- Stories/Levels: One
- Square Feet: 2,483
- Sq. Ft. Source: Public Records
- Year Built: 1950
Additional Structures
- Other Structures: Other, Outdoor Kitchen
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.36
- Lot Size (Sq. Ft.): 15,557
- Lot Size: 15557
- Street/Road Desc.: Paved
- Fencing (Description): Fenced
Financial Considerations
- Tax Amount: $18,715
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PORTION OF LOT 34, BEING DESC AS, COM AT NW COR OF SAID LOT 34 TH S-12-25-W 14.28 FT FOR POB TH CONT S-12-25-W 130 FT TO SW COR OF SAID LOT TH N-89-00-E 135.01 FT TO SE COR OF SAID LOT TH
- Flood Zone Info: X500
- APN: 2039070057
- Property ID: 2039070057
Listed by Compass Florida Llc
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Schools
Schools serving 3331 Old Oak Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 0.5 mi |
Brookside Middle School 3636 South Shade Avenue, Sarasota, FL 34239 | 6-8 | 0.9 mi |
Sarasota High School 2155 Bahia Vista Street, Sarasota, FL 34239 | 9-12 | 1.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 3331 Old Oak Dr
Date
Details
Price
Change
Source
2/18/2026
Price Reduced
$1,950,000
-2.26%
MLS
12/29/2025
Listed
$1,995,000
7.84%
MLS
2/21/2024
Sold
$1,850,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 3331 Old Oak Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,813
42%
$1,264,200
40%
2024
$13,225
3%
$901,828
3%
2023
$12,861
2%
$875,561
6%
2021
$12,588
—
$825,300
-3%
2022
$12,576
—
$850,059
16%
2021
$12,588
6%
$732,000
2%
2019
$11,845
-12%
$720,900
-12%
2018
$13,414
-4%
$817,100
-5%
2017
$14,027
9%
$857,000
12%
2016
$12,881
90%
$763,100
82%
2015
$6,776
—
$420,160
1%
2014
$6,767
—
$416,825
2%
2013
$6,751
—
$410,665
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 3331 Old Oak Dr
3331 Old Oak Drive, Sarasota, FL 34239 (MLS# A4675449) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 3331 Old Oak Drive is currently listed for $1,950,000 and was received on December 29, 2025. Want to learn more about 3331 Old Oak Drive? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

