3348 OLD OAK DRIVE, Sarasota, FL 34239

• 4 beds |
• 4 baths |
• 3,668 sqft

Property Description

Architecturally distinctive and exceptionally private, this furnished Mid-Century Modern residence is available for annual lease in one of Sarasota’s most sought-after West of the Trail locations. Ideally positioned near Siesta Key Beach, Siesta Village, and the shopping and dining of Southside Village, this home offers a rare combination of space, privacy, and proximity to everyday conveniences. Designed to embrace natural light and indoor-outdoor living, the home spans approximately 3,668 square feet and features four bedrooms, including a loft-style bedroom, along with multiple flexible living spaces. Soaring ceilings, expansive walls of glass, and dramatic cypress detailing throughout create a warm yet modern aesthetic that feels both timeless and livable. The main living areas flow effortlessly, anchored by a striking wood-burning fireplace and an open kitchen designed for gathering and entertaining. Multiple patios and outdoor sitting areas extend the living space into the beautifully landscaped grounds, offering a sense of tranquility and separation while remaining close to Sarasota’s most desirable destinations. The upstairs primary retreat provides a private sanctuary with a spacious bedroom, spa-inspired bath, and a dedicated laundry area. 2 additional upstairs bedrooms offer comfortable accommodations for guests or household members with a Jack & Jill bathroom. On the main level, a guest suite and a versatile bonus room provide ideal space for a home office, media room, or fitness area. Set on a large, private yard with bay views, the property features a heated indoor lap pool, allowing for year-round enjoyment regardless of season. A two-car garage with electric vehicle charging station adds modern convenience, and pets may be considered on a case-by-case basis with owner approval. Located West of the Trail and just minutes from Siesta Key Beach, Siesta Village, downtown Sarasota, Sarasota Memorial Hospital, marinas, and top local amenities, this home delivers the perfect balance of privacy, space, and accessibility. An exceptional opportunity for those seeking a long-term luxury rental in a premier Sarasota location.

Listing Status:

Active

Date Added:

December 27, 2025 at 06:00AM

Listing Office:

LOYD ROBBINS & CO. LLC : 941-957-9300

Listing Agent:

Ali Marks : 941-321-5147

MLS ID:

A4675245

Interior

• General: Ceiling Fans(s)Eat-in KitchenHigh CeilingsOpen FloorplanSolid Surface CountersSplit BedroomStone CountersThermostatWalk-In Closet(s)
• Rooms: Den/Library/Office
• Appliances: Built-In OvenDishwasherDisposalDryerExhaust FanFreezerMicrowaveRangeRange HoodRefrigeratorWasher
• Laundry: InsideLaundry RoomUpper Level
• Flooring: BambooTile
• A/C: Central Air
• Heating: Central
• Fireplace: Living RoomPrimary BedroomWood BurningFireplace

Exterior

• General: CourtyardPrivate MailboxSliding DoorsStorage
• Other Structures: PorchRear PorchScreenedPatio
• Pool: Child Safety FenceGuniteHeatedIn GroundIndoorLap
• Parking: Electric Vehicle Charging Station(s)Garage Door Opener

Construction

• General: Two

Location

• Road/Access: GravelPaved
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: 2039110038
• View: Trees/Woods

Utilities

• Utilities: Cable AvailableElectricity ConnectedPublicSewer ConnectedSprinkler WellWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS

This listing courtesy of Ali Marks, LOYD ROBBINS & CO. LLC