
860 N DENNING DRIVE, WINTER PARK, FL, 32789
Active57 days on marketListed Jun 1, 2026MLS #O6412589
About this home
860 N DENNING DRIVE
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,411
Sqft
0.14 ac
Lot size
1954
Year built
One
Levels
$496
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.
$4,582 /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
$4,582/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.
$/sqft vs Winter Park actives
$496 vs $343
Days on market
57 vs 34 typical
Where $496/sqft sits among the 316 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 Magnolia Gardens
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Magnolia Gardens — neighborhood snapshot
Population
109
Median age
44
Median income
$39,440
Median home value
$483,600
Avg household
2
Households w/ children
10%
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)
149 of 316
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 18% 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 860 N 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 · Apr ’26$372,400
770 CARVER STREET · same community
4 bd · 1.5 ba · 1,248 sqft · $298/sqft · 12 DOM
Sold · Jan ’26$409,000
900 CARVER STREET · same community
3 bd · 2 ba · 1,794 sqft · $228/sqft · 10 DOM
Sold · Feb ’26$610,000
1451 CAVENDISH ROAD
3 bd · 2 ba · 1,437 sqft · $424/sqft · 78 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 860 N DENNING DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 860 N DENNING DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
860 N DENNING DRIVE FAQs
What would the monthly payment be for 860 N DENNING DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,582/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 860 N DENNING DRIVE?+
The most recent tax bill on record (2025) was $4,595. 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 $699,900, this home is listed about 12% 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 860 N DENNING DRIVE?+
Lakemont Elementary (elementary), Maitland Middle (middle), 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
$699,900 is 18% below the WINTER PARK 32789 median of $849,450.
02Strong assigned schools
Lakemont Elementary, Maitland Middle, Winter Park High — Winter Park High rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $749,900, now $699,900 — a $50K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of OUTLET REALTY · LaDarrius Sanders. MLS #O6412589.
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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