3249 SAILING PIER AVENUE, WINTER GARDEN, FL, 34787
Active1 days on marketListed Nov 6, 2026MLS #G5119939
About this home
3249 SAILING PIER AVENUE
Virtually Staged. WELCOME HOME to the highly sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE in Winter Garden! Featuring $125,000 IN UPGRADES AND IMPROVEMENTS, this beautifully maintained home offers 4 BR, 3.5 BA, 2,964 SFT, a 2-car garage, and an exceptional floor plan! Impressive curb appeal begins with an upgraded stone elevation, designer glass and wrought-iron front door, extended paver driveway, and freshly painted exterior (2025). Inside, a spacious formal living room with French doors makes an ideal home office or den, while the OPEN-CONCEPT GREAT ROOM flows seamlessly into the beautifully appointed kitchen featuring white cabinetry, matte black hardware, QUARTZ COUNTERTOPS, and generous entertaining space. Extensive upgrades include HIGH-END PORCELAIN TILE FLOORING throughout the downstairs and bathrooms, upgraded wood stair treads with wrought-iron balusters, plantation shutters, and quartz countertops throughout. The spacious FIRST-FLOOR PRIMARY SUITE features a stylish barn door leading to a luxurious bath with soaking tub, oversized glass-enclosed shower, dual vanities, and a large walk-in closet with custom built-ins. A convenient half bath and laundry room with extensive cabinetry and sink complete the first floor. Upstairs offers a LARGE BONUS ROOM with luxury vinyl plank flooring, a spacious SECOND ENSUITE BEDROOM with private full bath, and two additional bedrooms sharing a full hallway bath. Additional improvements include upgraded carpeting, custom cabinetry and storage, enhanced lighting and electrical features, professionally coated garage floor, and an EXTENDED 10' x 26' SCREENED LANAI perfect for relaxing or entertaining. Residents enjoy RESORT-STYLE AMENITIES including a clubhouse, fitness center, zero-entry pool, splash pad, playground, walking trails, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE for kayaking, canoeing, and fishing. LOW HOA OF JUST $152/MONTH AND NO CDD FEE! Ideally located minutes from SR 429, Downtown Winter Garden, Winter Garden Village, Clermont, shopping, dining, entertainment, and major Central Florida highways. This exceptional home combines extensive upgrades, flexible living spaces, and an outstanding location in one of Winter Garden's most desirable gated communities. Schedule your private showing today!
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
2,964
Sqft
0.14 ac
Lot size
2
Garage
2020
Year built
Two
Levels
$228
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 and the real association fee — not generic estimates.
$5,187 /mo · 10% down Conventional, 30-yr fixed at 7.5%
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
$5,187/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.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
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
+12.7%
Days on market
1 vs 54 typical
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 Winter Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
WINTER GARDEN 34787 — neighborhood snapshot
Population
101,441
Median age
37.2
Median income
$120,365
Median home value
$539,500
Avg household
3.05
Households w/ children
14,635
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$582K → $566K
Winter Garden median sold, yr/yr
97.7%
Sale-to-list ratio (12 mo)
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 37% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
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
Nicholas Giaccone
Director of Agent Success · CENTURY 21 Edge
Tours, negotiation, and every question about 3249 SAILING PIER AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 3249 SAILING PIER AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Nicholas's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
3249 SAILING PIER AVENUE FAQs
What would the monthly payment be for 3249 SAILING PIER AVENUE?+
With 10% down on a 30-year Conventional loan at 7.5%, the all-in payment lands around $5,187/mo — principal and interest, the actual property-tax bill, the $152/mo association fee 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.
How much are the HOA fees at 3249 SAILING PIER AVENUE?+
The association fee works out to $152 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 3249 SAILING PIER AVENUE?+
The most recent tax bill on record (2025) was $4,489. 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 3249 SAILING PIER AVENUE?+
The listing reports pets: Number Limit, 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 Winter Garden?+
At $675,000, this home is listed about 13% above the Winter Garden median of $595,000. The market section on this page shows how the area is trending.
Which schools are assigned to 3249 SAILING PIER AVENUE?+
Water Spring Elementary (elementary), Horizon High School (high), Water Spring Middle School (middle) — Orange 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
$675,000 runs 37% above the WINTER GARDEN 34787 median — but at 2,964 sqft it's also 39% larger than the typical Winter Garden listing.
02Fresh on the market
Only 1 day on market in a Winter Garden market that averages 54 — if it fits, move quickly.
03Strong assigned schools
Water Spring Elementary, Horizon High School, Water Spring Middle School — Horizon High School rates 4 of 5. Always verify assignments with the district.
Listing courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY · Brandie Mathison-Klein. MLS #G5119939.
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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