744 CORNWALL ROAD, WINTER PARK, FL, 32792
Active356 days on marketListed Aug 1, 2025MLS #O6332168
About this home
744 CORNWALL ROAD
Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today! Also listed for rent
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
1,968
Sqft
0.23 ac
Lot size
2
Garage
1968
Year built
One
Levels
$343
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 — not generic estimates.
$4,502 /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
$4,502/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
−2.1%
Days on market
356 vs 34 typical
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 Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
WINTER PARK 32792 — neighborhood snapshot
Population
52,794
Median age
34.7
Median income
$66,176
Median home value
$343,500
Avg household
2.34
Households w/ children
5,372
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 Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 111% above the WINTER PARK 32792 median. See the full Winter Park market guide →
Paper trail
This home's history
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
John Carpenter
CFO/Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 744 CORNWALL ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 744 CORNWALL ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from John's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
744 CORNWALL ROAD FAQs
What would the monthly payment be for 744 CORNWALL ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,502/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 744 CORNWALL ROAD?+
The most recent tax bill on record (2024) was $5,359. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $675,000, this home is listed about 8% above the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 744 CORNWALL ROAD?+
Lakemont Elementary (elementary), Winter Park High (high), Maitland Middle (middle) — 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
$675,000 runs 111% above the WINTER PARK 32792 median.
02Time on market is leverage
356 days on market against a Winter Park median of 34 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Lakemont Elementary, Winter Park High, Maitland Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $750,000, now $675,000 — a $75K cut. The full history is in the market section below.
Listing courtesy of VERSALIS REALTY POWERED BY SELLSTATE · Tammy Cuddy. MLS #O6332168.
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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