1761 LEGION DRIVE, WINTER PARK, FL, 32789
Active47 days on marketListed Aug 26, 2026MLS #O6435967
About this home
1761 LEGION DRIVE
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was thoughtfully reimagined by renowned designer Ted Maines, resulting in a sophisticated yet timeless aesthetic throughout. Perfectly positioned on a prime oversized corner lot, this remarkable residence blends transitional architecture with modern elegance. Expansive sliding glass doors fill the open-concept living spaces with natural light while creating a seamless connection between the indoors and outdoors. The main living area flows effortlessly from the formal living room and spacious dining area into the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and premium Sub-Zero and Wolf appliances. A refined yet inviting family room with a fireplace provides the perfect setting for everyday living and entertaining. The private first-floor primary suite offers direct access to the lanai and heated saltwater pool and is complemented by a spa-inspired bath with a steam shower and custom his-and-her walk-in closets. A secondary ground-floor bedroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, a spacious loft with a custom dry bar leads to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a whole-house generator supported by a 250-gallon buried propane tank, new pool solar equipment, a newly added semi-circular driveway that enhances both curb appeal and functionality, two newer A/C units, and a new 2026 A/C system featuring re-engineered, high-efficiency ductwork designed to provide optimal climate control throughout the home. The outdoor living space is equally impressive, featuring a heated saltwater pool and spa with a cascading waterfall, elegant stone decking, an outdoor shower, ambient lighting, and a covered summer kitchen—perfect for year-round entertaining. A rare three-car garage completes this exceptional property. All of this is just moments from the shops, dining, parks, and unmistakable charm of downtown Winter Park
Facts & features
The home at a glance
5
Bedrooms
5.5
Bathrooms
4,949
Sqft
0.42 ac
Lot size
3
Garage
2017
Year built
Two
Levels
$660
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.
$20,904 /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
$20,904/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
+19.4%
$/sqft vs Winter Park actives
$660 vs $343
Days on market
47 vs 58 typical
Where $660/sqft sits among the 339 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 Green Oaks
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Green Oaks — neighborhood snapshot
Population
206
Median age
50
Median income
$169,125
Median home value
$1,052,600
Avg household
3
Households w/ children
20%
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 → $530K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
162 of 339
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 321% 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 1761 LEGION DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$5,410,000
2025 SUMMERLAND AVENUE · same community
5 bd · 4.5 ba · 4,432 sqft · $1,221/sqft · 0 DOM
Sold · Jul ’26$2,150,000
800 JUANITA RAEL · same community
5 bd · 4 ba · 4,021 sqft · $535/sqft · 56 DOM
Sold · Sep ’26$3,925,000
1417 WILLIAMS DRIVE
5 bd · 5.5 ba · 4,891 sqft · $802/sqft · 6 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
Pedro Ribeiro Gloria
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1761 LEGION DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1761 LEGION DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Pedro's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1761 LEGION DRIVE FAQs
What would the monthly payment be for 1761 LEGION DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $20,904/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 1761 LEGION DRIVE?+
The most recent tax bill on record (2025) was $22,817. 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 $3,265,000, this home is listed about 445% 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 1761 LEGION DRIVE?+
Dommerich 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
$3,265,000 runs 321% above the WINTER PARK 32789 median — but at 4,949 sqft it's also nearly 3 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
Dommerich Elementary, Maitland Middle, Winter Park High — Dommerich Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Harry Pool, III. MLS #O6435967.
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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