14050 FAIRWAY WILLOW LANE, WINTER GARDEN, FL, 34787
Active144 days on marketListed Mar 24, 2026MLS #O6392994
About this home
14050 FAIRWAY WILLOW LANE
Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
2,027
Sqft
0.66 ac
Lot size
2
Garage
1989
Year built
One
Levels
$353
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.
$5,019 /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
$5,019/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
+37.4%
$/sqft vs Winter Garden actives
$353 vs $259
Days on market
144 vs 40 typical
Where $353/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 Woodbridge On The Green
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Woodbridge On The Green — neighborhood snapshot
Population
132
Median age
37
Median income
$120,592
Median home value
$589,400
Avg household
3
Households w/ children
43%
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 → $630K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
195 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 35% 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 14050 FAIRWAY WILLOW LANE
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$450,000
4018 WILLOW BAY DRIVE · same community
3 bd · 2 ba · 2,075 sqft · $217/sqft · 12 DOM
Sold · Dec ’25$660,000
14014 FAIRWAY WILLOW LANE · same community
3 bd · 2 ba · 1,892 sqft · $349/sqft · 62 DOM
Sold · May ’26$600,000
4136 WILLOW BAY DRIVE · same community
3 bd · 2 ba · 2,472 sqft · $243/sqft · 16 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
Kat Bonelli
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 14050 FAIRWAY WILLOW LANE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14050 FAIRWAY WILLOW LANE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Kat's phone and CRM.
Straight answers
14050 FAIRWAY WILLOW LANE FAQs
What would the monthly payment be for 14050 FAIRWAY WILLOW LANE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,019/mo — principal and interest, the actual property-tax bill, the $322/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 14050 FAIRWAY WILLOW LANE?+
The association fee works out to $322 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 14050 FAIRWAY WILLOW LANE?+
The most recent tax bill on record (2025) was $4,924. 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 14050 FAIRWAY WILLOW LANE?+
The listing reports pets: Cats OK, Dogs OK. 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 $714,999, this home is listed about 22% above the Winter Garden median of $585,000. The market section on this page shows how the area is trending.
Which schools are assigned to 14050 FAIRWAY WILLOW LANE?+
Keenes Crossing Elementary (elementary), Windermere High (high), Bridgewater Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$714,999 runs 35% above the WINTER GARDEN 34787 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
144 days on market against a Winter Garden median of 40 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Keenes Crossing Elementary, Windermere High, Bridgewater Middle — Keenes Crossing Elementary rates 5 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $795,000, now $714,999 — a $80K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of LAKEFIELD REALTY GROUP LLC · Drew Ross. MLS #O6392994.
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 14050 FAIRWAY WILLOW LANE 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 Kat to ping you on any price or status change →