
1571 WOODLAND AVENUE, WINTER PARK, FL, 32789
Active72 days on marketListed May 29, 2026MLS #O6411706
About this home
1571 WOODLAND AVENUE
Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.
Facts & features
The home at a glance
5
Bedrooms
7
Bathrooms
7,397
Sqft
0.38 ac
Lot size
3
Garage
2007
Year built
Three Or More
Levels
$811
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.
$37,372 /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
$37,372/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
$811 vs $343
Days on market
72 vs 44 typical
Where $811/sqft sits among the 318 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
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
145 of 318
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 674% 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 1571 WOODLAND AVENUE
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$4,800,000
641 BONITA DRIVE · same community
5 bd · 5 ba · 6,699 sqft · $717/sqft · 0 DOM
Sold · Jul ’26$4,950,000
1660 PALMER AVENUE · same community
5 bd · 6.5 ba · 5,636 sqft · $878/sqft · 422 DOM
Sold · Jul ’26$2,650,000
1630 LASBURY AVENUE · same community
5 bd · 4 ba · 4,917 sqft · $539/sqft · 49 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 1571 WOODLAND AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1571 WOODLAND AVENUE — 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
1571 WOODLAND AVENUE FAQs
What would the monthly payment be for 1571 WOODLAND AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $37,372/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 1571 WOODLAND AVENUE?+
The most recent tax bill on record (2025) was $31,040. 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 $6,000,000, this home is listed about 902% above the Winter Park median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1571 WOODLAND AVENUE?+
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
$6,000,000 runs 674% above the WINTER PARK 32789 median — but at 7,397 sqft it's also nearly 4 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 CHARLES RUTENBERG REALTY ORLANDO · Vonda Fields. MLS #O6411706.
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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