2803 RIDDLE DRIVE, WINTER PARK, FL, 32789
Active13 days on marketListed Jul 10, 2026MLS #O6423829
Come see it
Upcoming open house
Sun, Jul 26
1:00 PM – 2:00 PM
About this home
2803 RIDDLE DRIVE
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,709
Sqft
0.25 ac
Lot size
2
Garage
1955
Year built
One
Levels
$333
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.
$3,983 /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
$3,983/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
+20.1%
$/sqft vs Winter Park actives
$333 vs $345
Days on market
13 vs 34 typical
Where $333/sqft sits among the 313 Winter Park 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 Fairbanks Shores
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Fairbanks Shores — neighborhood snapshot
Population
281
Median age
47
Median income
$75,484
Median home value
$272,208
Avg household
2
Households w/ children
26%
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)
143 of 313
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 33% below the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 2803 RIDDLE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$420,000
1357 FAIRVIEW STREET
3 bd · 2 ba · 1,740 sqft · $241/sqft · 5 DOM
Sold · Jan ’26$399,000
1604 ROOSEVELT AVENUE
4 bd · 2 ba · 1,664 sqft · $240/sqft · 212 DOM
Sold · May ’26$510,000
2913 CARROLL PLACE
3 bd · 2 ba · 1,654 sqft · $308/sqft · 159 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 2803 RIDDLE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2803 RIDDLE 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
2803 RIDDLE DRIVE FAQs
What would the monthly payment be for 2803 RIDDLE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $3,983/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 2803 RIDDLE DRIVE?+
The most recent tax bill on record (2025) was $6,477. 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 2803 RIDDLE 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 Park?+
At $569,000, this home is listed about 9% below the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2803 RIDDLE DRIVE?+
Killarney Elementary (elementary), Edgewater High (high), College Park Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the WINTER PARK 32789 market on paper
$569,000 is 33% below the WINTER PARK 32789 median of $849,950, and at $333/sqft it sits under the Winter Park average of $425.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03The price has already moved
Listed at $589,000, now $569,000 — a $20K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of CORCORAN PREMIER REALTY · Allie George. MLS #O6423829.
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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