3331 Old Oak Drive, FL
Stellar MLS

$1,895,000

3331 Old Oak Drive

Sarasota, FL 34239

Listing updated: June 1, 2026 at 10:28 AM ET

Active
4
Beds
4
Baths
2,483
Sq Ft
0.36
Acres
1950
Built
Private poolFireplace$763/sqft
Single Family Residence

Property type

1950

Year built

15,557 sqft

Lot size

$763

Price / sq ft

No HOA

HOA dues

117

Days on market

2

Garage spaces

X500

Flood zone

About this home

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 façade 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.

Estimated monthly payment

Principal & interest$9,582
Property taxes$1,560
Home insurance (est.)$869

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history117 days on market

  1. Status: Active
    Feb 18, 2026
  2. Listed$1,995,000
    Dec 29, 2025
  3. Price reduced$1,895,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
117
Subdivision
Shoreland Woods Sub
County
Sarasota
Year built
1950
Living area
2,483 sq ft
Price/sq ft
$763
Building area
3,453 sq ft (Public Records)
Lot size
15,557 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X500 (12115C0141F)
Garage
2 spaces
Pool
Private pool
Annual taxes
$18,715 (2025)
Parcel #
2039070057
Zoning
RSF2
MLS #
A4675449

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Interior Details

Bedrooms
4
Full bathrooms
3
Half bathrooms
1
Flooring
Wood
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
Interior features
Ceiling Fans(s), Dry Bar, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
West
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric, Natural Gas, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Boat, Driveway, Garage Door Opener, Guest, Oversized, Workshop in Garage

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
2 Weeks
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Please contact the city of Sarasota to verify any and all lease restrictions.

Exterior & Construction

Exterior features
French Doors, Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters
Construction materials
Frame
Roof
Metal
Foundation
Crawlspace
Pool
Private pool
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Natural Gas Available, Public, Sprinkler Well

Room Details

RoomLevelDimensions
Primary BedroomFirst18x27
Primary BathroomFirst
Living RoomFirst14x18
KitchenFirst10x21
Dining RoomFirst13x13
OfficeFirst16x10
Bedroom 3First10x11
Bedroom 2First14x12

Listing Details

Listing date
2025-12-29
On market date
2025-12-29
Original list price
$1,995,000
Occupant type
Owner
MLS area
34239 - Sarasota/Pinecraft
Listing AOR
Sarasota - Manatee
Status changed
2026-02-18
Tax 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 risk

Moderate riskFEMA Zone X500Panel 12115C0141F

Moderate-risk area (0.2% annual-chance / “500-year” floodplain). Flood insurance is recommended but usually not required.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

spring creek to old oak. home is on the left.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is 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.

Based on information submitted to the MLS GRID as of June 1, 2026 at 10:28 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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