14975 WINTER STAY DRIVE, WINTER GARDEN, FL, 34787
Active Under Contract34 days on marketListed Sep 8, 2026MLS #O6437980
About this home
14975 WINTER STAY DRIVE
Under contract-accepting backup offers. Welcome to 14975 Winter Stay Drive, where the work has already been done and the upgrades go far beyond builder basics. Thoughtfully improved inside and out, this Horizon West home pairs a warm, finished feel with the kind of practical upgrades you will appreciate for years to come. At the heart of the home, the kitchen features KitchenAid appliances installed in 2024. LVP flooring was added in 2025 and flows throughout the bedrooms. Plantation shutters, installed in 2026, add a polished finishing touch. Even the laundry room has been elevated with built-in cabinetry, granite countertops and additional storage. Outside is where this home really sets itself apart. The custom gunite pool, completed in 2024, features a swim shelf, heater AND chiller, upgraded screen enclosure and child safety fence, making it just as enjoyable in the heat of summer as it is on a cool Florida evening. The covered lanai was transformed into an outdoor living space with a fireplace, TV accent wall and recessed lighting, creating a true extension of the home for entertaining or relaxing year-round. The upgrades continue behind the scenes with a fully paid 15kW solar system, generator back-feed hookup, French drains along the east-facing gutters and downspouts, and overhead garage storage racks. Located in Winter Garden's sought-after Horizon West area, this is a home that has been intentionally upgraded, carefully maintained and designed to be lived in. Skip the projects and start enjoying the pool, the outdoor living space and everything this home has to offer from day one.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,662
Sqft
0.17 ac
Lot size
3
Garage
2019
Year built
One
Levels
$289
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.
$5,571 /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
$5,571/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
−8.2%
$/sqft vs Winter Garden actives
$289 vs $257
Days on market
34 vs 66 typical
Where $289/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 Hamlin
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Hamlin — neighborhood snapshot
Population
3,047
Median age
38
Median income
$178,486
Median home value
$603,785
Avg household
3
Households w/ children
429
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)
214 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 56% 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 14975 WINTER STAY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$830,000
14831 WINTER STAY DRIVE · same community
5 bd · 3 ba · 2,662 sqft · $312/sqft · 3 DOM
Sold · Apr ’26$535,000
9203 CUT SHOT DRIVE · same community
5 bd · 3.5 ba · 2,461 sqft · $217/sqft · 20 DOM
Sold · Sep ’25$520,000
7524 SUMMERLAKE GROVES STREET · same community
5 bd · 3 ba · 2,461 sqft · $211/sqft · 55 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
Shawn Headley
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 14975 WINTER STAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14975 WINTER STAY DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
14975 WINTER STAY DRIVE FAQs
What would the monthly payment be for 14975 WINTER STAY DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,571/mo — principal and interest, the actual property-tax bill, the $157/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 14975 WINTER STAY DRIVE?+
The association fee works out to $157 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 14975 WINTER STAY DRIVE?+
The most recent tax bill on record (2025) was $9,729. 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 14975 WINTER STAY 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 Winter Garden?+
At $770,000, this home is listed about 32% above the Winter Garden median of $584,900. The market section on this page shows how the area is trending.
Which schools are assigned to 14975 WINTER STAY DRIVE?+
Hamlin Middle (middle), Hamlin Elementary (elementary), Horizon High School (high) — 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
$770,000 runs 56% above the WINTER GARDEN 34787 median — but at 2,662 sqft it's also 26% larger than the typical Winter Garden listing.
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
Hamlin Middle, Hamlin Elementary, Horizon High School — Hamlin Middle rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of REAL BROKER, LLC · Ken Pozek. MLS #O6437980.
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.
Never miss a listing
New Winter Garden homes, in your inbox
Like 14975 WINTER STAY DRIVE but not quite? A daily digest of every new listing in Winter Garden — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Shawn to ping you on any price or status change →