3424 OLD OAK DRIVE, SARASOTA, FL, 34239
Active51 days on marketListed Aug 20, 2026MLS #A4702989
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About this home
3424 OLD OAK DRIVE
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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,368
Sqft
0.22 ac
Lot size
1
Garage
1953
Year built
One
Levels
$760
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$7,058 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$7,058/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+52.6%
$/sqft vs Sarasota actives
$760 vs $364
Days on market
51 vs 85 typical
Where $760/sqft sits among the 400 Sarasota actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Shoreland Woods
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Shoreland Woods — neighborhood snapshot
Population
472
Median age
59
Median income
$101,818
Median home value
$1,484,400
Avg household
2
Households w/ children
41%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$475K → $493K
Sarasota median sold, yr/yr
95.2%
Sale-to-list ratio (12 mo)
189 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 73% above the SARASOTA 34239 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 3424 OLD OAK DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’26$1,265,000
1780 SPRING CREEK DRIVE · same community
3 bd · 2 ba · 1,595 sqft · $793/sqft · 164 DOM
Sold · Apr ’26$598,990
2040 PALM TERRACE
4 bd · 2 ba · 1,362 sqft · $440/sqft · 81 DOM
Sold · Dec ’25$352,000
2108 LEE LANE
2 bd · 2 ba · 1,393 sqft · $253/sqft · 200 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Cindy Fernandez
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 3424 OLD OAK DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 3424 OLD OAK DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Cindy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
3424 OLD OAK DRIVE FAQs
What would the monthly payment be for 3424 OLD OAK DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $7,058/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 3424 OLD OAK DRIVE?+
The most recent tax bill on record (2025) was $10,828. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 3424 OLD OAK DRIVE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Sarasota?+
At $1,039,000, this home is listed about 89% above the Sarasota median of $550,000. The market section on this page shows how the area is trending.
Which schools are assigned to 3424 OLD OAK DRIVE?+
Southside Elementary School (elementary), Brookside Middle School (middle), Sarasota High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$1,039,000 runs 73% above the SARASOTA 34239 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Southside Elementary School, Brookside Middle School, Sarasota High School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of EXP REALTY LLC · Lise Wosick. MLS #A4702989.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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