229 ALEXANDER PLACE, WINTER PARK, FL, 32789
Active11 days on marketListed Jul 13, 2026MLS #O6412911
About this home
229 ALEXANDER PLACE
Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.
Facts & features
The home at a glance
4
Bedrooms
5
Bathrooms
4,431
Sqft
0.27 ac
Lot size
3
Garage
2011
Year built
Two
Levels
$959
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.
$27,746 /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
$27,746/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
$959 vs $343
Days on market
11 vs 34 typical
Where $959/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 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 32789 — neighborhood snapshot
Population
26,884
Median age
44.4
Median income
$100,213
Median home value
$695,000
Avg household
2.13
Households w/ children
2,125
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 400% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 229 ALEXANDER PLACE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$3,400,000
1208 NOTTINGHAM STREET
5 bd · 5.5 ba · 4,387 sqft · $775/sqft · 3 DOM
Sold · Jul ’25$3,222,222
1400 NOTTINGHAM STREET
5 bd · 5.5 ba · 4,369 sqft · $738/sqft · 59 DOM
Sold · Nov ’25$2,325,000
1268 PRESERVE POINT DRIVE
4 bd · 4 ba · 4,315 sqft · $539/sqft · 2 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 229 ALEXANDER PLACE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 229 ALEXANDER PLACE — 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
229 ALEXANDER PLACE FAQs
What would the monthly payment be for 229 ALEXANDER PLACE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $27,746/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 229 ALEXANDER PLACE?+
The most recent tax bill on record (2025) was $36,713. 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 $4,250,000, this home is listed about 578% 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 229 ALEXANDER PLACE?+
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
01Positioned at the premium end
$4,250,000 runs 400% above the WINTER PARK 32789 median — but at 4,431 sqft it's also nearly 2 times the size of the typical Winter Park listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Lakemont Elementary, Maitland Middle, Winter Park High — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COMPASS FLORIDA LLC · Brandon Geers. MLS #O6412911.
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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