$12,500/month
Off-Market Date: 01/23/20263348 Old Oak Drive Sarasota, FL 34239
Pending MLS# A4675245
4 beds 4 baths 3,668 sq ft Single Family
Details for 3348 Old Oak Drive
MLS# A4675245
Description for 3348 Old Oak Drive, Sarasota, FL, 34239
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 Information
Property Type: Rental, Single Family Residence
Status: Pending
Bedrooms: 4
Bathrooms: 4
Lot Size: 0.52 Acres
Square Feet: 3,668 sq ft
Year Built: 1977
Garage: Yes
Stories: 2 Story
Date Available: 12/29/2025
Construction Display: New Construction
Subdivision: Shoreland Woods Sub
County: Sarasota
Construction Status: New Construction
School Information
Elementary: Southside Elementary
Middle: Booker Middle
High: Sarasota High
Room Information
Main Floor
Bedroom 2: 14x7
Living Room: 22x22
Kitchen: 17x14
Upper Floor
Primary Bathroom: 22x25
Primary Bedroom: 16x22
Bathrooms
Full Baths: 4
Additonal Room Information
Laundry: Laundry Room, Upper Level, Inside
Interior Features
Appliances: Built-In Oven, Range Hood, Microwave, Range, Refrigerator, Washer, Dishwasher, Disposal, Dryer, Freezer, Exhaust Fan
Flooring: Bamboo,Tile
Fireplaces: Wood Burning, Living Room, Primary Bedroom
Additional Interior Features: Eat-In Kitchen, Walk-In Closet(s), High Ceilings, Split Bedrooms, Ceiling Fan(s), Solid Surface Counters, Stone Counters, Open Floorplan
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Electricity Connected,Municipal Utilities,Sewer Connected,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: Garage Door Opener, Garage, Electric Vehicle Charging Station(s)
Pool: Heated, Indoor, Other, In Ground, Gunite, Lap
Lot View: Bay,Trees/Woods,Water
Additional Exterior/Lot Features: Courtyard, Storage, Screened, Open, Patio, Porch, Rear Porch
Community Features
Security Deposit: 12500
Driving Directions
From Tamiami Trail take Siesta Drive west and turn right onto Old Oak Street, the house is on the left.
Financial Considerations
Tenant Pays: Gas
Owner Pays: Grounds Care,Internet,Pool Maintenance,Sewer,Trash Collection,Water
Tax/Property ID: 2039110038
A broker reciprocity listing courtesy: LOYD ROBBINS & CO. LLC
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Sales History & Tax Summary for 3348 Old Oak Drive
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 3348 Old Oak Drive
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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