433 GILBERT ROAD, WINTER PARK, FL, 32792
Active1 days on marketListed Jul 27, 2026MLS #O6428430
Come see it
Upcoming open house
Sat, Aug 1
12:00 PM – 2:00 PM
About this home
433 GILBERT ROAD
Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,770
Sqft
0.21 ac
Lot size
2
Garage
1965
Year built
One
Levels
$381
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.
$4,391 /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
$4,391/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
+13.6%
$/sqft vs WINTER PARK PINES
$381 vs $349
Days on market
1 vs 34 typical
Where $381/sqft sits among the 8 homes for sale in WINTER PARK PINES
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 32792 — neighborhood snapshot
Population
52,794
Median age
34.7
Median income
$66,176
Median home value
$343,500
Avg household
2.34
Households w/ children
5,372
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)
5 of 8
WINTER PARK PINES have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 105% above the WINTER PARK 32792 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 433 GILBERT ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$656,402
402 SAINT DUNSTAN WAY · same community
3 bd · 2 ba · 1,779 sqft · $369/sqft · 0 DOM
Sold · Apr ’26$629,000
513 CORNWALL ROAD · same community
3 bd · 2 ba · 1,735 sqft · $363/sqft · 39 DOM
Sold · Jul ’26$588,000
2756 SHERIFF WAY · same community
3 bd · 2 ba · 1,812 sqft · $325/sqft · 25 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
Lacie Springstead
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 433 GILBERT ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 433 GILBERT ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Lacie's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
433 GILBERT ROAD FAQs
What would the monthly payment be for 433 GILBERT ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,391/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 433 GILBERT ROAD?+
The most recent tax bill on record (2025) was $4,032. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 433 GILBERT ROAD?+
The listing reports pets: Cats OK, Dogs OK, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $675,000, this home is listed about 8% 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 433 GILBERT ROAD?+
Lakemont Elementary (elementary), Winter Park High (high), Maitland Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$675,000 runs 105% above the WINTER PARK 32792 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 1 day on market in a Winter Park market that averages 34 — if it fits, move quickly.
04Strong assigned schools
Lakemont Elementary, Winter Park High, Maitland Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS WINTER PARK · Amy Turner. MLS #O6428430.
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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