Landlord's Agent in 2026
Ali Marks
LOYD ROBBINS & CO. LLC
(941) 321-5147
1 in this area
56 Total Sales
3348 Old Oak Dr Sarasota, FL 34239
Southside NeighborhoodEstimated Value: $1,555,000 - $2,804,000
4
Beds
4
Baths
3,668
Sq Ft
$531/Sq Ft
Est. Value
Highlights
- Heated Indoor Pool
- Full Bay or Harbor Views
- Open Floorplan
- Southside Elementary School Rated A
- 0.52 Acre Lot
- Fireplace in Primary Bedroom
About This Home
As of February 2026Architecturally 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.
Last Agent to Rent the Property
LOYD ROBBINS & CO. LLC Brokerage Phone: 941-957-9300 License #3560076 Listed on: 12/27/2025
Last Renter's Agent
LOYD ROBBINS & CO. LLC Brokerage Phone: 941-957-9300 License #3560076 Listed on: 12/27/2025
Home Details
Home Type
- Single Family
Year Built
- Built in 1977
Lot Details
- 22,436 Sq Ft Lot
- East Facing Home
- Well Sprinkler System
Parking
- 2 Car Attached Garage
- Electric Vehicle Home Charger
- Garage Door Opener
Property Views
- Full Bay or Harbor
- Woods
Interior Spaces
- 3,668 Sq Ft Home
- 2-Story Property
- Open Floorplan
- Furnished
- Built-In Desk
- High Ceiling
- Ceiling Fan
- Wood Burning Fireplace
- Sliding Doors
- Living Room with Fireplace
- Den
Kitchen
- Eat-In Kitchen
- Built-In Oven
- Range with Range Hood
- Recirculated Exhaust Fan
- Microwave
- Freezer
- Dishwasher
- Stone Countertops
- Disposal
Flooring
- Bamboo
- Ceramic Tile
- Travertine
Bedrooms and Bathrooms
- 4 Bedrooms
- Fireplace in Primary Bedroom
- Split Bedroom Floorplan
- En-Suite Bathroom
- Walk-In Closet
- 4 Full Bathrooms
- Makeup or Vanity Space
- Bathtub With Separate Shower Stall
- Shower
- Garden Bath
Laundry
- Laundry Room
- Laundry on upper level
- Dryer
- Washer
Pool
- Heated Indoor Pool
- Heated Lap Pool
- Heated In Ground Pool
- Gunite Pool
- Child Gate Fence
Outdoor Features
- Courtyard
- Screened Patio
- Outdoor Storage
- Private Mailbox
- Rear Porch
Schools
- Southside Elementary School
- Booker Middle School
- Sarasota High School
Utilities
- Central Heating and Cooling System
- Vented Exhaust Fan
- Thermostat
- Cable TV Available
Community Details
- No Home Owners Association
- Shoreland Woods Community
- Shoreland Woods Sub Subdivision
Listing and Financial Details
- Residential Lease
- Security Deposit $12,500
- Property Available on 12/29/25
- Tenant pays for gas
- The owner pays for grounds care, internet, pool maintenance, sewer, trash collection, water
- 12-Month Minimum Lease Term
- Available 2/16/26
- $150 Application Fee
- 1 to 2-Year Minimum Lease Term
- Assessor Parcel Number 2039110038
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Closed on
Apr 20, 2021
Sold by
Bought by
Current Estimated Value
Purchase Details
Closed on
Dec 30, 2002
Sold by
Bought by
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$675,000
Interest Rate
0.0616%
Mortgage Type
New Conventional
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Home Values in the Area
Average Home Value in this Area
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $5,900 | None Available | ||
| $675,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $240,000 | ||
| Previous Owner | $675,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 02/16/2026 02/16/26 | Rented | $12,000 | -4.0% | -- |
| 01/23/2026 01/23/26 | Under Contract | -- | -- | -- |
| 12/27/2025 12/27/25 | For Rent | $12,500 | -- | -- |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $16,898 | $1,196,800 | ||
| 2024 | $17,279 | $1,088,000 | $748,700 | $339,300 |
| 2023 | $17,279 | $1,113,900 | $703,000 | $410,900 |
| 2022 | $16,226 | $1,038,700 | $639,600 | $399,100 |
| 2021 | $11,163 | $679,600 | $470,800 | $208,800 |
| 2020 | $9,333 | $586,422 | $0 | $0 |
| 2019 | $9,128 | $573,238 | $0 | $0 |
| 2018 | $8,981 | $562,550 | $0 | $0 |
| 2017 | $8,879 | $550,979 | $0 | $0 |
| 2016 | $8,883 | $842,000 | $461,800 | $380,200 |
| 2015 | $9,010 | $726,800 | $374,400 | $352,400 |
| 2014 | $8,887 | $518,321 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Ali Marks
-
Freya Robbins
Landlord's Co-Listing Agent in 2026
Freya Robbins
LOYD ROBBINS & CO. LLC
(941) 321-5142
1 in this area
50 Total Sales
Map
Source: Stellar MLS
MLS Number: A4675245
APN: 2039-11-0038
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Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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