
$1,895,000
3331 Old Oak Drive
Sarasota, FL 34239
Listing updated: June 1, 2026 at 10:28 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
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
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
- Status: ActiveFeb 18, 2026
- Listed$1,995,000Dec 29, 2025
- 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
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 18x27 |
| Primary Bathroom | First | |
| Living Room | First | 14x18 |
| Kitchen | First | 10x21 |
| Dining Room | First | 13x13 |
| Office | First | 16x10 |
| Bedroom 3 | First | 10x11 |
| Bedroom 2 | First | 14x12 |
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-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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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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