David Ramirez
$1,895,000$1,995,0004 bd3.5 ba2,483 sqft$763 /sqft$12,656 /mo all-in ↓

3331 OLD OAK DRIVE, SARASOTA, FL, 34239

Active206 days on marketListed Dec 29, 2025MLS #A4675449

Reduced $100KPrivate poolSingle Family ResidenceSHORELAND WOODS SUB

About this home

3331 OLD OAK DRIVE

A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks, setting an unforgettable first impression of timeless elegance and privacy. Wrapped in a freshly painted pecky cypress façade and crowned by a newer standing-seam metal roof, the residence honors classic Florida design while embracing today’s luxury standards. Inside, a welcoming foyer unfolds into an airy, open-concept living space anchored by rich natural wood floors and impeccable finishes throughout. A dramatic dual-sided stone fireplace creates a striking focal point between the living and dining areas, while a sophisticated dry bar sets the stage for effortless entertaining. A private office—thoughtfully positioned away from the main living areas—offers flexibility as a refined workspace or guest retreat, complete with an adjacent half bath. At the heart of the home, the chef’s kitchen is nothing short of spectacular, featuring premium stainless steel appliances, a natural gas range, custom cabinetry, designer backsplash, and an oversized marble island that commands attention. A built-in coffee bar adds a touch of indulgence, while French doors invite the outdoors in. Step into a resort-inspired sanctuary where a heated saltwater pool and spa shimmer beneath a newly installed panoramic screen enclosure. Entertain with ease in the fully equipped summer kitchen, complete with stainless gas grill, vent hood, and prep station, or gather around the gas fire pit for evenings under the palms. A newly updated outdoor shower with hot and cold water enhances the spa-like ambiance, while the expansive, lushly landscaped yard offers exceptional privacy and room to relax, play, or unwind. The primary suite is a true retreat, featuring three generous closets, a cozy fireplace, and French doors opening directly to the lanai for seamless indoor-outdoor living. The spa-inspired en-suite bath showcases luxurious finishes, custom vanities, and a walk-in shower designed for pure relaxation. Additional highlights include a spacious laundry room, oversized two-car garage, and curated architectural lighting that bathes the estate in a warm, elegant glow at dusk. Perfectly located just minutes from the Siesta Key North Bridge and the boutiques and dining of Southside Village, this property offers the rare balance of serene seclusion and coastal convenience. Situated outside of a flood zone—with flood insurance optional—this estate represents both luxury and peace of mind.

Facts & features

The home at a glance

4

Bedrooms

3.5

Bathrooms

2,483

Sqft

0.36 ac

Lot size

2

Garage

1950

Year built

One

Levels

$763

Per sqft

Private poolFireplaceTrees/Woods view

Inside

FlooringHardwood
AppliancesBar Fridge · Built-In Oven · Dishwasher · Disposal · Dryer · Microwave · Range · Refrigerator · Washer
InteriorCeiling Fan(s) · Dry Bar · Living Room/Dining Room Combo · Open Floorplan · Skylight(s) · Solid Surface Counters · Solid Wood Cabinets · Split Bedroom · Walk-In Closet(s)
LaundryInside · Laundry Room
CoolingCentral Air · Zoned
HeatingCentral · Electric · Natural Gas · Zoned

Outside & construction

RoofMetal
ConstructionWood Frame
FoundationCrawlspace
ViewTrees/Woods
FacesWest
ParkingBoat · Driveway · Garage Door Opener · Guest · Oversized · Workshop in Garage
ExteriorFrench Doors · Irrigation System · Lighting · Outdoor Kitchen · Outdoor Shower · Rain Gutters

Community & fees

Taxes (2025)$18,715/yr

Utilities & systems

UtilitiesBB/HS Internet Available · Natural Gas Available · Public · Sprinkler Well
WaterPublic

The numbers

What it really costs

Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.

$12,656 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$10,225
PMI (est., until 20% equity)$711
Property tax — 2025 actual bill$1,560
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $189,500Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $189,500
Interest rate6.00%
Loan term

Estimated payment

$12,656/mo

Principal & interest$10,225
PMI (est., until 20% equity)$711
Property taxes (actual bill)$1,560
Est. insurance$160

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.

List $1.9M
$1.3MedgeAI estimate $1,411,850 · range $1.4M$1.6M$2.0M

vs edgeAI estimate

+34.2%

$/sqft vs Sarasota actives

$763 vs $328

Days on market

206 vs 58 typical

Where $763/sqft sits among the 400 Sarasota actives

227
67
29 · this home
26
19
32
$149–384$384–618$618–853$853–1088$1088–1322$1322+

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

Map of 3331 OLD OAK DRIVE inside its neighborhood boundary

Drive times from this address

Downtown Tampa68 min

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

ElementarySouthside Elementary School★★★★★
MiddleBrookside Middle School★★★★★
HighSarasota High School★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Sarasota market

Seller’s marketBalanced6.0 months of inventoryBuyer’s market

$470K$470K

Sarasota median sold, yr/yr

95.1%

Sale-to-list ratio (12 mo)

147 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 192% above the SARASOTA 34239 median. See the full Sarasota market guide →

Paper trail

This home's history

CurrentPrice reduced to $1,895,000 $100K
Dec 29, 2025Listed at $1,995,000 · 206 days on market since
1950Built · SHORELAND WOODS SUB

Reality check

What actually sold near 3331 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.

1672 SHORELAND DRIVESold · Apr ’26

$950,000

1672 SHORELAND DRIVE · same community

3 bd · 2 ba · 2,266 sqft · $419/sqft · 51 DOM

2246 FIESTA DRIVESold · Sep ’25

$875,000

2246 FIESTA DRIVE

4 bd · 3.5 ba · 2,471 sqft · $354/sqft · 229 DOM

4665 PINE HARRIER DRIVESold · Aug ’25

$1,150,000

4665 PINE HARRIER DRIVE

3 bd · 2.5 ba · 2,499 sqft · $460/sqft · 29 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.

David Ramirez

Your agent

David Ramirez

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 3331 OLD OAK DRIVE — start here.

Andrew Acosta

Your lender

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Pre-approval, rates, and the real monthly number for 3331 OLD OAK DRIVE — before you fall in love.

See it in person

Schedule a tour

Pick a day that works — this goes straight to David's phone and CRM.

Goes straight to David’s phone and CRM.

Straight answers

3331 OLD OAK DRIVE FAQs

What would the monthly payment be for 3331 OLD OAK DRIVE?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $12,656/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 3331 OLD OAK DRIVE?+

The most recent tax bill on record (2025) was $18,715. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.

How does the price compare to other homes in Sarasota?+

At $1,895,000, this home is listed about 232% above the Sarasota median of $570,000. The market section on this page shows how the area is trending.

Which schools are assigned to 3331 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

Five things that matter here

01Positioned at the premium end

$1,895,000 runs 192% above the SARASOTA 34239 median — but at 2,483 sqft it's also 48% larger than the typical Sarasota listing.

02Your own pool

A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.

03Time on market is leverage

206 days on market against a Sarasota median of 58 — sellers in this position are usually ready to negotiate.

04Strong assigned schools

Southside Elementary School, Brookside Middle School, Sarasota High School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.

05The price has already moved

Listed at $1,995,000, now $1,895,000 — a $100K cut. The full history is in the market section below.

Listing courtesy of COMPASS FLORIDA LLC · Adnan Dedic. MLS #A4675449.

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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