1808 WESTERN TRAILWAY DRIVE, WINTER GARDEN, FL, 34787
Active29 days on marketListed Jul 7, 2026MLS #S5152973
About this home
1808 WESTERN TRAILWAY DRIVE
Fresh New Price! If you’ve been waiting for the right home at the right price, this is it! Make your move before the new school year begins and enjoy everything this wonderful family-friendly community has to offer. This gem is a beautifully maintained 3-bedroom, 2-bath home, offering over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter seating, and seamless flow into the living and dining areas—perfect for everyday living and entertaining. Step outside to your private backyard featuring maintenance-free turf, providing a lush, green outdoor space you can enjoy year-round without the upkeep. Residents also enjoy access to the community pool, scenic walking trails, and direct access to the West Orange Trail, with beautiful Lake Apopka just a couple of blocks away. Best of all, you’ll enjoy all these incredible amenities while benefiting from a LOW HOA FEE! Whether you’re purchasing your first home, growing your family, or right-sizing after the kids have moved out, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Hull Island is a welcoming, family-oriented community for all ages, conveniently located near charming downtown Winter Garden, shopping, dining, parks, and major roadways. Don’t miss your opportunity to make this move-in-ready home your own!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,860
Sqft
0.14 ac
Lot size
2
Garage
2019
Year built
One
Levels
$317
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.
$4,423 /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
$4,423/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
+20%
$/sqft vs Winter Garden actives
$317 vs $261
Days on market
29 vs 37 typical
Where $317/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 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
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
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)
172 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 10% 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 1808 WESTERN TRAILWAY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$635,000
1382 FOLTZ LOOP · same community
4 bd · 3 ba · 2,268 sqft · $280/sqft · 69 DOM
Sold · Mar ’26$649,000
2169 BAY LINE ROAD · same community
4 bd · 3 ba · 2,274 sqft · $285/sqft · 14 DOM
Sold · Jun ’26$1,730,000
1216 HULL ISLAND DRIVE · same community
5 bd · 4.5 ba · 4,224 sqft · $410/sqft · 8 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1808 WESTERN TRAILWAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1808 WESTERN TRAILWAY 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.
Straight answers
1808 WESTERN TRAILWAY DRIVE FAQs
What would the monthly payment be for 1808 WESTERN TRAILWAY DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,423/mo — principal and interest, the actual property-tax bill, the $165/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 1808 WESTERN TRAILWAY DRIVE?+
The association fee works out to $165 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1808 WESTERN TRAILWAY DRIVE?+
The most recent tax bill on record (2025) was $8,389. 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 1808 WESTERN TRAILWAY DRIVE?+
The listing reports pets: Breed Restrictions, 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 $589,000, this home is priced right at the Winter Garden median.
Which schools are assigned to 1808 WESTERN TRAILWAY DRIVE?+
Sunridge 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
Three things that matter here
01Positioned at the premium end
$589,000 runs 10% above the WINTER GARDEN 34787 median.
02Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $599,000, now $589,000 — a $10K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of FLORIDA IN MOTION REALTY INC · Susan Koptieff. MLS #S5152973.
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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