1333 S DENNING DRIVE, WINTER PARK, FL, 32789
Pending4 days on marketListed Aug 12, 2026MLS #O6431370
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Sun, Aug 16
1:00 PM – 4:00 PM
Call 321-277-8271 with questions.
About this home
1333 S DENNING DRIVE
Winter Park 32789 - Affordable single-family home across from beautiful Mead Botanical Gardens – or a great parcel to build your new abode. Lot size 60’ x 125’ (.17 acre) on sewer. Perhaps a rental investment property – Rollins College campus is less than 1 mile away. This charming and solid 2 bed, 1 bath block home with carport offers a NEW ROOF (2026) and fresh paint inside and out with original hardwood parquet floors. It even has double pane windows to help keep the heat out and the cool in (AC 2018). The front living room leads to the kitchen (freshly painted wood cabinets), which opens to a bright and sunny eating area (an additional 140 sq ft not accounted for in property records) with a handy inside laundry closet (washer/dryer included). The two bedrooms have ceiling fans and a shared hall bathroom (tub/shower combo) which completes the inside spaces. Out back you’ll find a covered patio and the spacious and grassy fenced-in backyard. This fantastic location in sought after 32789 is just a block away from the entrance to Winter Park’s 55-acre Mead Botanical Gardens, 2 blocks from the Winter Park Tennis Center, the new Seven Oaks Park, and a short bike ride to Foxtail Coffee, Rollins College, and famed Park Ave shops and restaurants (1 mile away). Come call this your new home, rental investment, or buildable parcel for your new construction abode.
Facts & features
The home at a glance
2
Bedrooms
1
Bathrooms
702
Sqft
0.17 ac
Lot size
1950
Year built
One
Levels
$426
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.
$2,347 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$2,347/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
−17.1%
$/sqft vs Winter Park actives
$426 vs $343
Days on market
4 vs 41 typical
Where $426/sqft sits among the 325 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 Mead Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Mead Garden — neighborhood snapshot
Population
767
Median age
48
Median income
$88,672
Median home value
$626,400
Avg household
2
Households w/ children
47%
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
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
150 of 325
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 63% 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 1333 S DENNING DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$300,000
1313 S DENNING DRIVE · same community
3 bd · 2 ba · 1,700 sqft · $176/sqft · 0 DOM
Sold · Feb ’26$435,000
1629 DAUPHIN LANE
2 bd · 1 ba · 725 sqft · $600/sqft · 2 DOM
Sold · Apr ’26$184,300
225 E NEW HAMPSHIRE STREET UNIT 21
2 bd · 1 ba · 594 sqft · $310/sqft · 105 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
Yumiko Sugawara
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1333 S DENNING DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1333 S DENNING DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Yumiko's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1333 S DENNING DRIVE FAQs
What would the monthly payment be for 1333 S DENNING DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,347/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 1333 S DENNING DRIVE?+
The most recent tax bill on record (2025) was $3,532. 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 $299,000, this home is listed about 48% below the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1333 S DENNING DRIVE?+
Audubon Park School (elementary), Winter Park High (high) — 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
$299,000 is 63% below the WINTER PARK 32789 median of $815,000, and at $426/sqft it sits under the Winter Park average of $431.
02Fresh on the market
Only 4 days on market in a Winter Park market that averages 41 — if it fits, move quickly.
03Strong assigned schools
Audubon Park School, Winter Park High — Audubon Park School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS WINTER PARK · Steven Ritz. MLS #O6431370.
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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