434 VALLEY VIEW DRIVE, WINTER GARDEN, FL, 34787
Active18 days on marketListed Jul 16, 2026MLS #O6425087
About this home
434 VALLEY VIEW DRIVE
Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
2,765
Sqft
0.33 ac
Lot size
2
Garage
2000
Year built
Two
Levels
$344
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.
$6,066 /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
$6,066/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
+34.7%
$/sqft vs Winter Garden actives
$344 vs $260
Days on market
18 vs 31 typical
Where $344/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 Courtlea Oaks
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Courtlea Oaks — neighborhood snapshot
Population
361
Median age
50
Median income
$54,242
Median home value
$266,700
Avg household
3
Households w/ children
32%
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 → $628K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
163 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 79% 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 434 VALLEY VIEW DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$950,000
403 COURTLEA CREEK DRIVE · same community
5 bd · 3 ba · 2,886 sqft · $329/sqft · 41 DOM
Sold · Nov ’25$1,000,000
436 VALLEY VIEW DRIVE · same community
3 bd · 3.5 ba · 3,130 sqft · $319/sqft · 59 DOM
Sold · Jul ’26$1,225,000
705 GARDEN WEST TERRACE
4 bd · 3 ba · 2,698 sqft · $454/sqft · 49 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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 434 VALLEY VIEW DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 434 VALLEY VIEW DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
434 VALLEY VIEW DRIVE FAQs
What would the monthly payment be for 434 VALLEY VIEW DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,066/mo — principal and interest, the actual property-tax bill, the $83/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 434 VALLEY VIEW DRIVE?+
The association fee works out to $83 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 434 VALLEY VIEW DRIVE?+
The most recent tax bill on record (2025) was $4,087. 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 434 VALLEY VIEW 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 $950,000, this home is listed about 61% above the Winter Garden median of $589,945. The market section on this page shows how the area is trending.
Which schools are assigned to 434 VALLEY VIEW DRIVE?+
Dillard Street Elementary (elementary), Lakeview 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
$950,000 runs 79% above the WINTER GARDEN 34787 median — but at 2,765 sqft it's also 27% 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
Dillard Street Elementary, Lakeview Middle, West Orange High — West Orange High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of LAKESIDE REALTY WINDERMERE INC · Jennifer Coon. MLS #O6425087.
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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