A private garden retreat in one of Sarasota’s most coveted West of Trail locations. * * Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a captivating Sarasota bungalow where privacy, character, and effortless coastal living come together. From the moment you arrive, the home unfolds through a collection of intimate, inviting spaces. A charming front patio beneath a mature, vine-covered pergola offers a welcoming setting for morning coffee or an evening glass of wine. Winding garden paths and established tropical foliage create the feeling of a secluded sanctuary. The outdoor living experience continues around the heated pool, surrounded by greenery for exceptional privacy. A hot-and-cold outdoor shower adds resort-style convenience—ideal after a relaxing afternoon poolside or a day at nearby Siesta Key Beach. Multiple outdoor gathering areas invite you to follow the sun, unwind in a quiet garden corner, or entertain beneath the Florida sky. Inside, the three-bedroom, two-bath residence is filled with warmth and personality. Vaulted ceilings enhance the sense of openness, while a wood-burning fireplace creates an unexpected and inviting focal point. French doors connect the interior living spaces to the gardens and pool, creating a seamless flow between indoor and outdoor living. The home’s distinctive character is matched by its exceptional West of Trail location. Just over the North Bridge from Siesta Key, you are minutes from its renowned beaches while remaining conveniently close to Southside Village, Sarasota Memorial Hospital, downtown Sarasota, dining, shopping, arts, and entertainment. 3424 Old Oak Drive offers something increasingly difficult to find: an established tropical setting, mature gardens, exceptional privacy, and authentic Sarasota charm. In a location that keeps the best of the city and coast within easy reach.
Shoreland Woods, located between U.S. 41 (Tamiami Trail) and Sarasota Bay, is a residential and coastal Sarasota neighborhood with leafy streets and bay-breeze calm. The neighborhood’s character concentrates around the Ringling Causeway and Bayfront Drive, where joggers, cyclists, and waterfront views set the daily rhythm. Mid-century ranch homes and newer rebuilds sit behind mature trees, with short blocks that lead toward the water. Nearby cultural pillars such as The Ringling, Asolo Repertory Theatre, and the Sarasota Opera shape an arts-forward backdrop. Evenings often orbit around St. Armands Circle’s independent boutiques and cafes, while Bayfront Park frames the shoreline with open lawns and paths.
Provided by Walk Score and Local Logic
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Ceiling fans
Vaulted ceilings
Skylight(s)
Wood-burning fireplace in the living room
Family room
Bedrooms
3 bedrooms
Bathrooms
2 full bathrooms
Kitchen
Dishwasher
Disposal
Microwave
Range
Range hood
Refrigerator
Laundry & utility
Washer and dryer (inside laundry)
Utility connections for water and electricity
Flooring
Tile
Vinyl
Heating & cooling
Central heating
Central air conditioning
Exterior features
Patio
French doors
Sliding doors
Outdoor shower
Wood fencing
Mature landscaping
Shed(s)
Heated in-ground pool with spa and screen enclosure
Home design
Single-family residence
One story
South-facing
Parking
Circular driveway
Driveway
Attached garage (1-car)
Construction
Frame construction
Shingle roof
Slab foundation
Built with public records living area of 1,368 (units reported)
Utilities
Public water
Public sewer
Electricity connected
Cable available
Water connected
HOA & community
No association approval required
Pets allowed
Other
Property type: Residential (Single Family Residence)
Property condition: Completed
Zoning: RSF2
Lot dimensions approximately 114 x 85 x 113 x 87 on ~0.22 acre (paved, public maintained road)
Direction faces: South
Unfurnished
No home warranty
Electricity and solar
View estimated energy costs and solar savings for this home
Charming and stylish, here is the perfect year round home, vacation escape or investment property. Former owners used this as a rental property and generated $50,000 in income. Surrounded by lush gardens and outdoor living space which is completely fenced, you will be delighted by your private, heated pool where you can truly enjoy the Florida lifestyle. The updated home is inviting and comfortable and features vaulted ceilings, lots of natural light, French doors, PGT windows, a wood burning fireplace and extra flexible space that would work well as a home office or extra space for visitors to stay. Best of all is the location. West of the Trail and just over the North Bridge to Siesta Key, you are right near Southside Village, Sarasota Memorial Hospital, Southside Elementary School and conveniently close to downtown. This is one of the most desirable neighborhoods in Sarasota, and here is the opportunity you have been waiting for. Furniture is available under separate contract.
Stellar MLS as Distributed by MLS Grid #A4482741
Nov 17, 2020
Listing Removed
—
Nov 8, 2020
Listed
*
Stellar MLS as Distributed by MLS Grid #A4152916
Jul 18, 2016
Sold
$550,000
$402/sq ft
Jun 22, 2016
Pending
—
May 6, 2016
Contingent
—
Apr 28, 2016
Listed
$579,000
$423/sq ft
Stellar MLS as Distributed by MLS Grid #A3957219
Oct 30, 2012
Sold
$280,000
$205/sq ft
Mar 9, 2012
Listed
$300,000
$219/sq ft
Public Records
Oct 5, 1999
Sold
$141,400
$103/sq ft
Public Records
Nov 1, 1991
Sold
$121,000
$88/sq ft
Public Records
May 9, 1988
Sold
$100,000
$73/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$11,280 (+6.8%)
$520,700 + $253,100
$773,800
2024
$10,562 (+2.7%)
2023
$10,284 (+2.2%)
2022
$10,061 (+68.6%)
$464,500 + $234,700
$699,200
2021
$5,966 (−1.1%)
2020
$6,032 (+2.7%)
2019
$5,872 (−10.9%)
$275,000 + $121,300
$396,300
2018
$6,590 (−0.3%)
$294,300 + $145,900
$440,200
2017
$6,610 (+2.6%)
$284,800 + $151,400
$436,200
2016
$6,443 (+9.7%)
$307,900 + $112,100
$420,000
2015
$5,875 (+15.0%)
2014
$5,107 (+26.6%)
2013
$4,034 (+65.1%)
2012
$2,444
Public record
Public record
Zoning
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
9,773 Sq. Ft.
Year renovated
2008
Finished Sq. Ft.
1,368
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,368
Year built
1953
Style
Single Family Residential
County
Sarasota County
APN
2039110034
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 10, 2026.
RSF-2
Residential Single Family 2 District
The intent and purpose of the Residential Single Family RSF districts is to preserve land for housing and provide housing opportunities for individual households. The regulations are intended to create, maintain and promote the development and redevelopment of these neighborhoods while preserving their existing residential character. The regulations preserve the character of neighborhoods by providing six different densities and development standards. These zones allow some non-household living uses but not to such an extent as to sacrifice the overall image and character of the neighborhood. The regulations promote desirable residential areas by addressing aesthetically pleasing environments, safety, privacy, and recreational opportunities. The site development standards allow flexibility of development while maintaining compatibility within the city's various neighborhoods. In addition, the regulations provide clarity to property owners, developers, and neighbors about the limits of what is allowed.
Permitted uses
Include but are not limited to:
Housing-Group
Housing-Single unit
Park & open space
Climate risks
8/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
10/10 Heat Factor
7 days above 107° expected this year, 25 days in 30 years
10/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Sarasota, FL • 34239
Average low and high temperatures (°F)
69
51
73
57
79
62
84
67
86
74
89
76
91
78
90
78
90
76
85
70
80
63
75
58
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
96/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 26% for direct sun exposure in Sarasota. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.7 hrs
7.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 3424 Old Oak Dr
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $390,000 and $1,825,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $390K to $1.8M.