14827 MASTHEAD LANDING CIRCLE, WINTER GARDEN, FL, 34787
Active3 days on marketListed Aug 3, 2026MLS #O6429897
About this home
14827 MASTHEAD LANDING CIRCLE
Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,648
Sqft
0.13 ac
Lot size
2
Garage
2005
Year built
Two
Levels
$232
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.
$4,341 /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
$4,341/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
−3.9%
$/sqft vs Winter Garden actives
$232 vs $261
Days on market
3 vs 38 typical
Where $232/sqft sits among the 400 Winter Garden 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 Stoneybrook West
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Stoneybrook West — neighborhood snapshot
Population
3,360
Median age
46
Median income
$126,768
Median home value
$394,860
Avg household
3
Households w/ children
533
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
$585K → $611K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
171 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 15% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 14827 MASTHEAD LANDING CIRCLE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$690,000
2149 BLACK LAKE BOULEVARD · same community
4 bd · 3 ba · 2,709 sqft · $255/sqft · 65 DOM
Sold · Sep ’25$530,000
13224 FOX GLOVE STREET · same community
4 bd · 2 ba · 2,535 sqft · $209/sqft · 18 DOM
Sold · Oct ’25$548,000
1319 CASTLEPORT ROAD · same community
4 bd · 2 ba · 2,518 sqft · $218/sqft · 80 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
Steeve Cadeau
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 14827 MASTHEAD LANDING CIRCLE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14827 MASTHEAD LANDING CIRCLE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Steeve's phone and CRM.
Straight answers
14827 MASTHEAD LANDING CIRCLE FAQs
What would the monthly payment be for 14827 MASTHEAD LANDING CIRCLE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,341/mo — principal and interest, the actual property-tax bill, the $243/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 14827 MASTHEAD LANDING CIRCLE?+
The association fee works out to $243 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 14827 MASTHEAD LANDING CIRCLE?+
The most recent tax bill on record (2025) was $4,671. 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 14827 MASTHEAD LANDING CIRCLE?+
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 Winter Garden?+
At $615,000, this home is listed about 4% above the Winter Garden median of $590,000. The market section on this page shows how the area is trending.
Which schools are assigned to 14827 MASTHEAD LANDING CIRCLE?+
Whispering Oak Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$615,000 runs 15% above the WINTER GARDEN 34787 median — but at 2,648 sqft it's also 22% larger than the typical Winter Garden listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Fresh on the market
Only 3 days on market in a Winter Garden market that averages 38 — if it fits, move quickly.
04Strong assigned schools
Whispering Oak Elementary, Sunridge Middle, West Orange High — Whispering Oak Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY · Tennille Biggers. MLS #O6429897.
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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